US20090189522A1 - Aromatic amine derivative and organic electroluminescence device employing the same - Google Patents

Aromatic amine derivative and organic electroluminescence device employing the same Download PDF

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US20090189522A1
US20090189522A1 US12/368,486 US36848609A US2009189522A1 US 20090189522 A1 US20090189522 A1 US 20090189522A1 US 36848609 A US36848609 A US 36848609A US 2009189522 A1 US2009189522 A1 US 2009189522A1
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Masakazu Funahashi
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Idernitsu Kosan Co Ltd
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Definitions

  • the present invention relates to an aromatic amine derivative and an organic electroluminescence device using the derivative and, more particularly, to an organic electroluminescence device having long lifetime, an enhanced efficiency of light emission and emitting highly pure blue light; and to an aromatic amine derivative realizing the organic electroluminescence device.
  • Organic electroluminescence (“electroluminescence” will be occasionally referred to as “EL”, hereinafter) devices which utilize organic substances are expected to be useful for application as an inexpensive full color display device of the solid light emission type having a great size and various developments on the organic EL devices are being conducted.
  • an organic EL device has a construction comprising a light emitting layer and a pair of electrodes sandwiching the light emitting layer.
  • the light emission of the organic EL device is a phenomenon in which, when an electric field is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light emitting layer to form an excited state, and energy generated when the excited state returns to the ground state is emitted as light.
  • Patent Literature 1 there is disclosed such a technique using a single monoanthracene compound as an organic light-emitting material (refer to Patent Literature 1 below).
  • a luminance obtained by using the material is as low as 1650 cd/m 2 , for example, at a current density of 165 mA/cm 2 , and an efficiency of light emission thereof is very low, i.e., only 1 cd/A, which is practically unusable.
  • Patent Literature 2 there is disclosed a technique using a single bisanthracene compound as an organic light emitting material.
  • an efficiency of light emission obtained by using the material is also as low as about 1 to 3 cd/A.
  • Patent Literature 4 a technique of employing mono- or bis-anthracene compound and a distyryl compound as an organic light emitting medium layer is disclosed (refer to Patent Literature 4 below).
  • a conjugated structure of the styryl compound lengthened wave length of a light emission spectrum and deteriorated the purity of color.
  • Patent Literature 5 discloses a blue luminescence device with the use of diaminochrysene derivatives. However, despite the superiority in light emission efficiency, because the device is not sufficient in its lifetime, further improvement was required.
  • An object of the present invention is to provide organic EL devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic EL devices.
  • the object of the present invention can be achieved by using aromatic amine derivatives represented by a following general formula (1) or (2) in which an amino group is bonded to a substituted chrysene structure.
  • the present invention has been accomplished on the basis of the above finding.
  • the present invention provides an aromatic amine derivative represented by the following general formula (1) or general formula (2):
  • a 1 to A 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 560 ring
  • a, b, c and d each independently represents an integer of 0 to 5, when a, b, c or d each is 2 or greater, A 1 to A 4 may be the same with or different from each other, and may bond each other to form a saturated or unsaturated ring; and further, a couple of A 1 and A 2 , and a couple of A 3 and A 4 may bond each other to form a saturated or unsaturated ring; R 1 to R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20
  • a 5 to A 8 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms;
  • R 5 to R 5 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms; and a couple of R 5 and R 6 , and a couple of R 7 and R 8 may bond each other to form a saturated or unsaturated ring.
  • the present invention provides an organic EL device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layers comprises the aromatic amine derivative singly or as its mixture component.
  • the organic EL device employing the aromatic amine derivative of the present invention reveals practically sufficient luminance even under low applied voltage, exhibits an enhanced efficiency of light emission, and is resistant to degrade even after a long time usage demonstrating a prolonged lifetime.
  • FIG. 1 is a chart showing a result of 1 H-NMR measurement about Compound (4) obtained in Synthesis Example 1;
  • FIG. 2 is a chart showing a result of 1 H-NMR measurement about Compound (9) obtained in Synthesis Example 2;
  • FIG. 3 is a chart showing a result of 1 H-NMR measurement about Compound (20) obtained in Synthesis Example 3;
  • FIG. 4 is a chart showing a result of 1 H-NMR measurement about Compound (23) obtained in Synthesis Example 4;
  • FIG. 5 is a chart showing a result of 1 H-NMR measurement about Compound (25) obtained in Synthesis Example 5;
  • FIG. 6 is a chart showing a result of 1 H-NMR measurement about Compound (39) obtained in Synthesis Example 6;
  • FIG. 7 is a chart showing a result of 1 H-NMR measurement about Compound (57) obtained in Synthesis Example 7;
  • FIG. 8 is a chart showing a result of 1 H-NMR measurement about Compound (95) obtained in Synthesis Example 8;
  • FIG. 9 is a chart showing a result of 1 H-NMR measurement about Compound (D-973) obtained in Synthesis Example 9;
  • FIG. 10 is a chart showing a result of 1 H-NMR measurement about Compound (D-974) obtained in Synthesis Example 10;
  • FIG. 11 is a chart showing a result of 1 H-NMR measurement about Compound (D-998) obtained in Synthesis Example 11;
  • FIG. 12 is a chart showing a result of 1 H-NMR measurement about Compound (D-1000) obtained in Synthesis Example 12;
  • the present invention provides an aromatic amine derivative represented by a following general formula (1) or a general formula (2):
  • a 1 to A 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 (preferably 1 to 6) carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted
  • Examples of the substituted or unsubstituted alkyl group represented by A 1 to A 4 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc.
  • Examples of the substituted or unsubstituted aryl group represented by A 1 to A 4 include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group, etc.
  • Examples of the substituted or unsubstituted aralkyl group represented by A 1 to A 4 include benzyl group, ⁇ , ⁇ -methylphenylbenzyl group, triphenylmethyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisoprop
  • Examples of the cycloalkyl group represented by A 1 to A 4 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc.
  • Examples of the alkoxy group represented by A 1 to A 4 include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, various pentyloxy groups, various hexyloxy groups, etc.
  • Examples of the aryloxy group represented by A 1 to A 4 include phenoxy group, tolyloxy group, naphthyloxy group, etc.
  • Examples of the arylamino group represented by A 1 to A 4 include diphenylamino group, ditolylamino group, isopropyldiphenylamino group, t-butyldiphenylamino group, diisopropyldiphenylamino group, di-t-butyldiphenylamino group, dinaphthylamino group, naphthylphenylamino group, etc.
  • Examples of the alkylamino group represented by A 1 to A 4 include dimethylamino group, diethylamino group, dihexylamino group, etc.
  • heterocyclic group represented by A 1 to A 4 examples include moieties of imidazole, benzimidazole, pyrrole, furan, thiophene, benzothiophene, oxadiazoline, indoline, carbazole, pyridine, quinoline, isoquinoline, benzoquinone, pyrazoline, imidazolidine, piperidine, etc.
  • Examples of the substituted or unsubstituted silyl group represented by A 1 to A 4 include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, methyldiphenylsilyl group, dimethylphenylsilyl group, triphenylsilyl group), etc.
  • Examples of the halogen atom represented by A 1 to A 4 include fluorine atom, chlorine atom, bromine atom, etc.
  • a, b, c and d each independently represents an integer of 0 to 5, preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • a 1 to A 4 may be the same with or different from each other, and may bond each other to form a saturated or unsaturated ring; and further, a couple of A 1 and A 2 , and a couple of A 3 and A 4 may bond each other to form a saturated or unsaturated ring;
  • Examples of the ring include cycloalkane having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, etc.; cycloalkene having 4 to 12 carbon atoms such as cyclobutene, cyclopentene, cyclohexene, cyclo heptene, cyclo octene, etc.; cycloalkadiene having 6 to 12 carbon atoms such as cyclohexa diene, cyclohepta diene, cyclo octadiene, etc.; aromatic ring having 6 to 50 carbon atoms such as benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, acenaphthylene, etc.; and the like.
  • R 1 to R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group (preferably a primary or a secondary alkyl group) having 1 to 50 (preferably 1 to 0.20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 (preferably 1 to 10) carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 50 (preferably 3 to
  • substituted or unsubstituted alkyl group aryl group, aralkyl group, cycloalkyl group, arylamino group, alkylamino group, heterocyclic group, silyl group and the saturated or unsaturated ring represented by R 1 to R 4 are the same as those exemplified as A 1 to A 4 above.
  • alkyl group represented by R 2 and R 4 are primary or secondary.
  • examples of the substituent for A 1 to A 4 and R 1 to R 4 include a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted arylthio group having.
  • 5 to 50 preferably 5 to 20 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 (preferably 1 to 20) carbon atoms, amino group, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, etc.
  • R 1 and/or R 3 independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 1 and R 3 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 1 to R 4 each independently represents a hydrogen atom, a substituted or unsubstituted arylamino group having 5 to 20 ring, carbon atoms; a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms or a substituted or unsubstituted silyl group having 0.3 to 50 carbon atoms.
  • R 1 and/or R 3 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a s-butyl group, a t-butyl group or a cyclohexyl group.
  • R 2 and/or R 4 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a s-butyl group, a t-butyl group or a cyclohexyl group.
  • a 5 to R 8 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms;
  • R 5 to R 8 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 (preferably 1 to 10) carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms; a couple of R 5
  • the aromatic amine derivative of the present invention since the aryl group (in particular, a benzene ring), the alkyl group, the cycloalkyl group or the heterocyclic group is connected to a diaminocrysene structure as a light emission center, an association between the compounds is prevented, resulting in a prolonged lifetime thereof. Moreover, because coupling a bulky substituent to the chrysene backbone structure increases a steric repulsion against the amine structure, the lifetime prolongs further.
  • the aryl group in particular, a benzene ring
  • the aromatic amine derivatives have a strong fluorescence in a solid state, and are excellent in an electric field light emission, which leads to a fluorescent quantum efficiency as high as 0.3 or more.
  • the aromatic amine derivatives of the present invention exhibit not only excellent capabilities of injecting and transporting holes from the metal electrode or organic thin film layers, but also excellent capabilities of injecting and transporting electrons from the metal electrode or organic thin film layers and, therefore, are usefully employable as light emitting materials, particularly doping materials for organic EL devices.
  • the aromatic amine derivatives of the present invention may be used together with other hole transporting materials, electron transporting materials or doping materials.
  • the organic EL device of the present invention comprises one or plural organic thin film layers sandwiched between an anode and a cathode.
  • a light emitting layer as the organic thin film layer is sandwiched between the anode and cathode.
  • the light emitting layer contains the light emitting material and may further contain a hole injecting material and an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material.
  • the aromatic amine derivatives of the present invention have an enhanced light emitting property and excellent hole injecting capability and hole transporting capability as well as excellent electron injecting capability and electron transporting capability and, therefore, can be employed as a light emitting material or a doping material in the light emitting layer.
  • the light emitting layer contains the aromatic amine derivative of the present invention in an amount of preferably 0.1 to 20% by weight and more preferably 1 to 10% by weight.
  • the aromatic amine derivatives of the present invention exhibit not only an extremely high fluorescent quantum efficiency but also high hole transporting capability and electron transporting capability, and further are capable of forming a uniform thin film, so that the light emitting layer may be formed from the aromatic amine derivatives only.
  • the organic thin film layers preferably include an organic layer containing the aromatic amine derivative of the present invention as an essential component which is provided between the anode and the light emitting layer.
  • an organic layer may be a hole injecting layer, a hole transporting layer, etc.
  • aromatic amine derivative of the present invention is employed as a doping material
  • at least one kind selected from the group consisting of anthracene derivatives of a following general formula (3), anthracene derivatives of a following general formula (4) and pyrene derivatives of a following general formula (5) is employed as a host material.
  • X 1 and X 2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to
  • Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms; at least one of Ar 1 or Ar 2 represents a substituted or unsubstituted aryl group with a condensed ring and having 10 to 50 ring carbon atoms; and m represents an integer of 1 to 3.
  • m is 2 or greater, a group within the above parentheses: [ ] may be the same with or different from each other.
  • X 1 to X 3 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50
  • Ar 1 represents a substituted or unsubstituted aryl group with a condensed ring and having 10 to 50 ring carbon atoms and Ar 3 represents a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms; n represents an integer of 1 to 3. When n is 2 or greater, a group within the above parentheses: [ ] may be the same with or different from each other.
  • anthracene derivative represented by the general formulae (3) and (4) will be illustrated below, though not particularly limited thereto.
  • Ar 5 and Ar 6 each represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
  • Examples of the organic EL device of a multilayer type include those having multilayer structures such as (an anode/a hole injecting layer/a light emitting layer/a cathode), (an anode/a light emitting layer/an electron injecting layer/a cathode) and (an anode/a hole injecting layer/a light emitting layer/an electron injecting layer/a cathode).
  • the multilayers may also optionally contain, in addition to the aromatic amine derivatives of the present invention, conventionally known materials such as light emitting materials, doping materials, hole injecting materials and electron injecting materials according to requirements.
  • conventionally known materials such as light emitting materials, doping materials, hole injecting materials and electron injecting materials according to requirements.
  • the organic EL device having such a multilayer structure can be prevented from suffering from deterioration in luminance and lifetime due to quenching.
  • the light emitting materials, doping materials, hole injecting materials and electron injecting materials may be used in combination with each other.
  • the use of the doping materials enables the resultant device to be improved in luminance of light emission and efficiency of light emission, and further emit a red color light or a blue color light.
  • the hole injecting layer, the light emitting layer and the electron injecting layer may respectively have a multilayer structure including two or more layers.
  • a layer injecting holes from the electrode is called as a hole injecting layer
  • a layer for accepting the holes from the hole injecting layer and transporting the holes to the light emitting layer is called as a hole transporting layer.
  • a layer injecting electrons the electrode is called as an electron injecting layer
  • a layer transporting for accepting the electrons from the electron injecting layer and transporting the electrons to the light emitting layer is called as an electron transporting layer.
  • Those respective layers may be selectively used according to various factors such as energy level of the materials used, heat resistance, and adhesion to the organic thin film layers or the metal electrodes.
  • Examples of the host material or the doping material besides the foregoing general formulae (3) to (5) employable for the light emitting layer together with the aromatic amine derivative of the present invention include condensed mass aromatic compound such as naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenyl cyclopentadiene, fluorene, spiro fluorene, 9,10-diphenylanthracene, 9,10-bis(phenyl-ethynyl)anthracene, 1,4-bis(9′-ethynyl anthracenyl)benzene and those derivatives; organometallic complex such as tris(8-quinolinolat)aluminium, bis-(2-methyl-8-quinolinolat)-4-(
  • the hole injecting material is preferably made of compounds which have a good hole transporting capability as well as excellent capabilities of accepting holes injected from the anode and injecting the holes into the light emitting layer or light emitting material, prevent excited particles produced in the light emitting layer from moving into the electron injecting layer or electron injecting material, and exhibit an excellent capability of forming a thin film.
  • the hole injecting material include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazole thione, pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acyl hydrazone, polyaryl alkanes, stilbene, butadiene, benzidine-type triphenyl amine, styryl amine-type triphenyl amine, diamine-type triphenyl amine and derivatives thereof, as well as polyvinyl carbazoles, polysilanes, and high molecular materials such as electro-conductive polymers, though not particularly limited thereto.
  • hole injecting materials usable in the organic EL device of the present invention are aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • aromatic tertiary amine derivatives include triphenyl amine, tritolyl amine, tolyldiphenyl amine, N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-phenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N,N′-(methylphenyl)-N,N′-(4-n-butylphenyl)-phenanthrene-9,10-diamine, N,N-bis(4-di-4-tolylaminophenyl, N
  • phthalocyanine (Pc) derivatives include phthalocyanine derivatives such as H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPc—O—GaPc, as well as naphthalocyanine derivatives, though not particularly limited thereto.
  • phthalocyanine derivatives such as H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPc—O
  • the organic EL device of the present invention between the light emitting layer and the anode, there is preferably formed a layer such as the above hole transporting layer or hole injecting layer containing those aromatic tertiary amine derivatives and/or phthalocyanine derivatives.
  • the electron injecting material is preferably made of compounds which have a good electron transporting capability as well as excellent capabilities of accepting electrons injected from the cathode and injecting the electrons into the light emitting layer or light emitting material, prevent excited particles produced in the light emitting layer from moving into the hole injecting layer, and exhibit an excellent capability of forming a thin film.
  • Specific examples of the electron injecting material include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrane dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, though not particularly limited thereto.
  • an electron accepting substance and an electron donating substance may be added to the hole injecting material and the electron injecting material, respectively, for enhanced sensitization thereof.
  • more effective electron injecting materials are metal complex compounds and five-member ring derivatives having a nitrogen atom.
  • metal complex compounds include 8-hydroxyquinolinatolithium, bis(8-hydroxy(quinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato) m anganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato)gallium, though not particularly limited thereto.
  • the five-member ring derivatives having a nitrogen atom are preferably derivatives of oxazole, thiazole, oxadiazole, thiadiazole or triazole.
  • Specific examples of the nitrogen-containing five-member ring derivatives include 2,5-bis(1-phenyl)-1,3,4-oxazole, dimethyl POPOP, 2,5-bis(1-phenyl)-1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole, 2-(4′-tert-butylphenyl)-5-(4′′-biphenyl)-1,3,4-oxadiazole, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole, 1,4-bis[2-(5-phenyloxadiazolyl)]benzene, 1,4-bis[2-(5-phenyloxadiazolyl)-4-tert-butylbenzene], 2-(4′-
  • the light emitting layer may also optionally contain, in addition to the aromatic amine derivatives represented by the general formula (1), at least one material selected from the group consisting of light emitting materials, doping materials, hole injecting materials and electron injecting materials.
  • the organic EL device of the present invention may be further provided with a protective layer on a surface thereof, or the whole part thereof may be protected with silicone oil, resins, etc., in order to enhance stability thereof against temperature, humidity, atmosphere, etc.
  • the anode of the organic EL device according to the present invention may be suitably made of an electro-conductive material having a work function more than 4 eV.
  • the electro-conductive material for the anode include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium and alloys thereof, metal oxides such as tin oxide and indium oxide which are used for ITO substrates or NESA substrates, and organic electro-conductive resins such as polythiophene and polypyrrole.
  • the cathode of the organic EL device according to the present invention may be suitably made of an electro-conductive material having a work function of 4 eV or less.
  • Examples of the electro-conductive material for the cathode include magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride and alloys thereof, though not particularly limited thereto.
  • Typical examples of the alloys include alloys of magnesium and silver, alloys of magnesium and indium, and alloys of lithium and aluminum, though not particularly limited thereto.
  • the ratio between the constituting metals in the alloys may be controlled and appropriately determined depending upon temperature of vapor deposition sources, atmosphere, vacuum degree, etc.
  • the anode and cathode may be constituted of two or more layers, if required.
  • At least one surface of the organic EL device of the present invention preferably exhibits a sufficient transparency in a wavelength range of light emitted therefrom in order to enhance an efficiency of light emission thereof.
  • the substrate for the device is also preferably transparent.
  • the transparent electrode is formed using the above electro-conductive material by vapor deposition method, sputtering method, etc., so as to ensure a desirable transparency thereof.
  • the electrode disposed on a light emitting surface of the device preferably has a light transmittance of 10% or greater.
  • the substrate is not particularly limited as long as it suitably has a good mechanical and thermal strength as well as a good transparency. Examples of the substrate include glass substrates and transparent resin films.
  • the transparent resin films include films made of polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylons, polyether ether ketones, polysulfones, polyether sulfones, tetrafluoroethylene-perfluoroalkylvinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride, polyesters, polycarbonates, polyurethanes, polyimides, polyether imides and polypropylene.
  • the respective layers of the organic EL device of the present invention may be formed by either a dry film-forming process such as vacuum deposition, sputtering, plasma and ion-plating, or a wet film-forming process such as spin-coating, dipping and flow-coating.
  • the thickness of the respective layers is not particularly limited, but should be adjusted to an appropriate range. When the thickness is too large, a large electric voltage must be applied to the device in order to achieve a predetermined light output, resulting in a poor efficiency of light emission. On the other hand, when the thickness is too small, pinholes tend to be formed in the layers, thereby failing to obtain a sufficient luminance of light emission even upon applying an electric field thereto.
  • the suitable thickness of the respective layers is usually in the range of from 5 nm to 10 ⁇ m and preferably from 10 nm to 0.2 ⁇ m.
  • materials constituting the respective layers are dissolved or dispersed in a suitable solvent such as ethanol, chloroform, tetrahydrofuran and dioxane to form a thin film thereof.
  • a suitable solvent such as ethanol, chloroform, tetrahydrofuran and dioxane.
  • the solvent used for forming the respective layers is not particularly limited.
  • suitable resins or additives may be added to the respective organic thin film layers for the purposes of improving a film-forming property, preventing formation of pinholes in the resultant film, etc.
  • the resins usable for the above purposes include insulating resins such as polystyrene, polycarbonates, polyarylates, polyesters, polyamides, polyurethanes, polysulfones, polymethyl methacrylate, polymethyl acrylate and celluloses as well as copolymers thereof, photoconductive resins such as poly-N-vinyl carbazole and polysilanes, and electro-conductive resins such as polythiophene and polypyrrole.
  • the additives include antioxidants, ultraviolet absorbers and plasticizers.
  • the organic EL device of the present invention is suitably applied to, for example, planar light-emitting members such as a wall-hanging type television flat panel displays or so, light sources for copiers, printers, back light for liquid crystal displays and, measuring instruments, display panels, marker light, etc.
  • planar light-emitting members such as a wall-hanging type television flat panel displays or so
  • the material of the present invention can be used not only for organic EL devices but also in other applications such as electronic photographic members, photoelectric converter elements, solar cells, image sensors, etc.
  • trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol), dichloro (diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5% by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into a three neck flask with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to ⁇ 20° C.
  • trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol), dichloro (diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5% by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into three necked-flask equipped with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to ⁇ 20° C.
  • 2-bromo-6-isopropylnaphthalene in an amount of 9.4 g (38 mmol), desiccated ether in an amount of 100 milliliter and desiccated toluene in an amount of 50 milliliter were placed into a three necked-flask equipped with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to ⁇ 40° C. After slowly dripping n-butyllithium in an amount of 25 milliliter (40 mmol, 1.58M (n-hexane)) into the flask, the resultant solution was stirred at a temperature of ⁇ 20° C. for 2 hours.
  • 2-hydroxy-5-isopropylbenzaldehyde in an amount of 4.4 g (27 mmol), trifluoromethane sulfonic acid anhydride in an amount of 11.2 g (40 mmol), pyridine in an amount of 6 milliliter (80 mmol) and dichloromethane in an amount of 100 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for 2 hours.
  • 6,12-dibromochrysene in, an amount of 3.8 g (10 mmol), N-methylaniline in an amount of 2.7 g (25 mmol, palladium acetate in an amount of 0.03 g (1.6% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night.
  • a 120 nm-thick transparent electrode made of indium oxide was formed on a glass substrate having a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm.
  • the glass substrate with the transparent electrode was cleaned by irradiation of Ultra Violet ray and ozone.
  • the thus cleaned glass substrate with the transparent electrode was mounted to a vacuum vapor deposition apparatus.
  • N′,N′′-bis[4-(diphenylamino)phenyl]-N′,N′′-diphenylbiphenyl-4,4′-diamine was vapor-deposited to form a hole injecting layer having a thickness of 60 nm
  • N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-bendizine was vapor deposited on the hole injecting layer to form a hole transporting layer having a thickness of 20 nm.
  • 10,10′-bis[1,1′,4′,1′′]terphenyl-2-yl-9,9′-bianthracenyl and the above Compound (9) were simultaneously vapor deposited at a weight ratio of 40:2 on the hole transporting layer to form a light emitting layer having a thickness of 40 nm.
  • tris(8-hydroxyquinolinato)aluminum was vapor-deposited on the light emitting layer to form an electron injecting layer having a thickness of 10 nm. Then, tris(8-hydroxyquinolinato)aluminum and lithium was vapor-deposited at a weight ratio of 10:0.3 on the electron injecting layer to form a layer having a thickness of 10 nm, and further aluminum was vapor-deposited thereon to form an aluminum layer having a thickness of 150 nm. The aluminum layer functioned as a cathode. Thus, an organic EL device was fabricated.
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that Compound (9) was replaced with Compound (23).
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that 10,10′-bis[1,1′,4′,1′]terphenyl-2-yl-9,9′-bianthracenyl was replaced with 10-(3-(naphthalen-1-yl)phenyl)-9-(naphthalen-2-yl)anthracene.
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (23) for the doping material.
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (25) for the doping material.
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (10) for the doping material.
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that Compound (9) was replaced with 6,12-bis(4-isopropylphenyl-p-tolylamino)chrysene.
  • the organic EL device using the aromatic amine derivative according to the present invention can exhibit a practically sufficient luminance of light emission even upon applying a low voltage thereto, and has an enhanced efficiency of light emission and the device is free from deterioration in properties even after being used for a long period of time and, therefore, has a long lifetime. Resultantly, the EL device is useful as a flat panel light emitting member for a wall-hanging type television or as a light source of backlight and the like for display devices.

Abstract

A specified aromatic amine derivative having a chrysene structure. An organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layer comprises the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic electroluminescence devices are provided.

Description

    TECHNICAL FIELD
  • The present invention relates to an aromatic amine derivative and an organic electroluminescence device using the derivative and, more particularly, to an organic electroluminescence device having long lifetime, an enhanced efficiency of light emission and emitting highly pure blue light; and to an aromatic amine derivative realizing the organic electroluminescence device.
    • BACKGROUND ART
  • Organic electroluminescence (“electroluminescence” will be occasionally referred to as “EL”, hereinafter) devices which utilize organic substances are expected to be useful for application as an inexpensive full color display device of the solid light emission type having a great size and various developments on the organic EL devices are being conducted. In general, an organic EL device has a construction comprising a light emitting layer and a pair of electrodes sandwiching the light emitting layer. The light emission of the organic EL device is a phenomenon in which, when an electric field is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light emitting layer to form an excited state, and energy generated when the excited state returns to the ground state is emitted as light.
  • As compared with an inorganic light emitting diode, conventional organic EL devices requires high driving voltage and only exhibited low luminance or low efficiency of light emission. Moreover, characteristic degradation of the conventional organic EL devices was also extravagant and as a result, they were not practically used. Although recent organic EL devices are improved step by steps, it has been still demanded to develop organic EL devices with favorable efficiency of light emission and having long lifetime.
  • For example, there is disclosed such a technique using a single monoanthracene compound as an organic light-emitting material (refer to Patent Literature 1 below). However, in this technique, a luminance obtained by using the material is as low as 1650 cd/m2, for example, at a current density of 165 mA/cm2, and an efficiency of light emission thereof is very low, i.e., only 1 cd/A, which is practically unusable. Also, there is disclosed a technique using a single bisanthracene compound as an organic light emitting material (refer to Patent Literature 2 below). However, in this technique, an efficiency of light emission obtained by using the material is also as low as about 1 to 3 cd/A. Therefore, further improvement of the technique has bee demanded for rendering it practically usable. Further, there is disclosed a technique using a distyryl compound and adding styrylamine or so as organic light emitting material (refer to Patent Literature 3 below). However, the device described therein fails to show a sufficiently long lifetime and, therefore, further improvement has been demanded.
  • Furthermore, a technique of employing mono- or bis-anthracene compound and a distyryl compound as an organic light emitting medium layer is disclosed (refer to Patent Literature 4 below). However in these technologies, a conjugated structure of the styryl compound lengthened wave length of a light emission spectrum and deteriorated the purity of color.
  • Still further, Patent Literature 5 below discloses a blue luminescence device with the use of diaminochrysene derivatives. However, despite the superiority in light emission efficiency, because the device is not sufficient in its lifetime, further improvement was required.
      • Patent Literature 1: Japanese Unexamined Patent Application Laid-Open No. Hei 11-3782A
      • Patent Literature 2: Japanese Unexamined Patent Application Laid-Open No. Hei 8 (1996)-012600
      • Patent Literature 3: International Patent Application Published under PCT No. WO 00/06402
      • Patent Literature 4: Japanese Unexamined Patent Application Laid-Open No. 2001-284050
      • Patent Literature 5: International Application Published under PCT No. WO 04/04088
    DISCLOSURE OF THE INVENTION
  • The present invention has been made to overcome the above problems. An object of the present invention is to provide organic EL devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic EL devices.
  • As a result of extensive researches for developing aromatic amine derivatives having the above suitable properties and organic EL devices using the aromatic amine derivatives, the inventors have found that the object of the present invention can be achieved by using aromatic amine derivatives represented by a following general formula (1) or (2) in which an amino group is bonded to a substituted chrysene structure. The present invention has been accomplished on the basis of the above finding.
  • Namely, the present invention provides an aromatic amine derivative represented by the following general formula (1) or general formula (2):
  • Figure US20090189522A1-20090730-C00001
  • In the general formula (1), A1 to A4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 560 ring carbon atoms, a substituted or unsubstituted silyl group having 3 to 50 carbon atoms or a halogen atom;
  • a, b, c and d each independently represents an integer of 0 to 5, when a, b, c or d each is 2 or greater, A1 to A4 may be the same with or different from each other, and may bond each other to form a saturated or unsaturated ring; and further, a couple of A1 and A2, and a couple of A3 and A4 may bond each other to form a saturated or unsaturated ring;
    R1 to R4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms or a substituted or unsubstituted silyl group having 3 to 50 carbon atoms; a couple of R1 and R2, and a couple of R3 and R4 may bond each other to form a saturated or unsaturated ring.
  • However, a case where all of R1 to R4 in the general formula (1) are hydrogen atoms is excluded.
  • Figure US20090189522A1-20090730-C00002
  • In the general formula (2), A5 to A8 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms;
  • R5 to R5 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms; and a couple of R5 and R6, and a couple of R7 and R8 may bond each other to form a saturated or unsaturated ring.
  • Further, the present invention provides an organic EL device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layers comprises the aromatic amine derivative singly or as its mixture component.
  • The organic EL device employing the aromatic amine derivative of the present invention reveals practically sufficient luminance even under low applied voltage, exhibits an enhanced efficiency of light emission, and is resistant to degrade even after a long time usage demonstrating a prolonged lifetime.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a chart showing a result of 1H-NMR measurement about Compound (4) obtained in Synthesis Example 1;
  • FIG. 2 is a chart showing a result of 1H-NMR measurement about Compound (9) obtained in Synthesis Example 2;
  • FIG. 3 is a chart showing a result of 1H-NMR measurement about Compound (20) obtained in Synthesis Example 3;
  • FIG. 4 is a chart showing a result of 1H-NMR measurement about Compound (23) obtained in Synthesis Example 4;
  • FIG. 5 is a chart showing a result of 1H-NMR measurement about Compound (25) obtained in Synthesis Example 5;
  • FIG. 6 is a chart showing a result of 1H-NMR measurement about Compound (39) obtained in Synthesis Example 6;
  • FIG. 7 is a chart showing a result of 1H-NMR measurement about Compound (57) obtained in Synthesis Example 7;
  • FIG. 8 is a chart showing a result of 1H-NMR measurement about Compound (95) obtained in Synthesis Example 8;
  • FIG. 9 is a chart showing a result of 1H-NMR measurement about Compound (D-973) obtained in Synthesis Example 9;
  • FIG. 10 is a chart showing a result of 1H-NMR measurement about Compound (D-974) obtained in Synthesis Example 10;
  • FIG. 11 is a chart showing a result of 1H-NMR measurement about Compound (D-998) obtained in Synthesis Example 11; and
  • FIG. 12 is a chart showing a result of 1H-NMR measurement about Compound (D-1000) obtained in Synthesis Example 12;
    •  THE PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
  • The present invention provides an aromatic amine derivative represented by a following general formula (1) or a general formula (2):
  • Figure US20090189522A1-20090730-C00003
  • Figure US20090189522A1-20090730-C00004
  • First, the aromatic amine derivative represented by the general formula (1) will be explained below.
  • In the general formula (1), A1 to A4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 (preferably 1 to 6) carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 (preferably 1 to 6) carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms, a substituted or unsubstituted silyl group having 3 to 50 (preferably 3 to 20) carbon atoms or a halogen atom.
  • Examples of the substituted or unsubstituted alkyl group represented by A1 to A4 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc.
  • Examples of the substituted or unsubstituted aryl group represented by A1 to A4 include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group, etc.
  • Examples of the substituted or unsubstituted aralkyl group represented by A1 to A4 include benzyl group, α,α-methylphenylbenzyl group, triphenylmethyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, -naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group; α-phenoxybenzyl group, α-benzyloxy benzyl group, α,α-ditrifluoromethylbenzyl group, 1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group, etc.
  • Examples of the cycloalkyl group represented by A1 to A4 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Examples of the alkoxy group represented by A1 to A4 include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, various pentyloxy groups, various hexyloxy groups, etc.
  • Examples of the aryloxy group represented by A1 to A4 include phenoxy group, tolyloxy group, naphthyloxy group, etc.
  • Examples of the arylamino group represented by A1 to A4 include diphenylamino group, ditolylamino group, isopropyldiphenylamino group, t-butyldiphenylamino group, diisopropyldiphenylamino group, di-t-butyldiphenylamino group, dinaphthylamino group, naphthylphenylamino group, etc.
  • Examples of the alkylamino group represented by A1 to A4 include dimethylamino group, diethylamino group, dihexylamino group, etc.
  • Examples of the heterocyclic group represented by A1 to A4 include moieties of imidazole, benzimidazole, pyrrole, furan, thiophene, benzothiophene, oxadiazoline, indoline, carbazole, pyridine, quinoline, isoquinoline, benzoquinone, pyrazoline, imidazolidine, piperidine, etc.
  • Examples of the substituted or unsubstituted silyl group represented by A1 to A4 include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, methyldiphenylsilyl group, dimethylphenylsilyl group, triphenylsilyl group), etc.
  • Examples of the halogen atom represented by A1 to A4 include fluorine atom, chlorine atom, bromine atom, etc.
  • In the general formula (1), a, b, c and d each independently represents an integer of 0 to 5, preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • When a, b, c or d each is 2 or greater, A1 to A4 may be the same with or different from each other, and may bond each other to form a saturated or unsaturated ring; and further, a couple of A1 and A2, and a couple of A3 and A4 may bond each other to form a saturated or unsaturated ring;
  • Examples of the ring include cycloalkane having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, etc.; cycloalkene having 4 to 12 carbon atoms such as cyclobutene, cyclopentene, cyclohexene, cyclo heptene, cyclo octene, etc.; cycloalkadiene having 6 to 12 carbon atoms such as cyclohexa diene, cyclohepta diene, cyclo octadiene, etc.; aromatic ring having 6 to 50 carbon atoms such as benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, acenaphthylene, etc.; and the like.
  • In the general formula (1), R1 to R4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group (preferably a primary or a secondary alkyl group) having 1 to 50 (preferably 1 to 0.20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 (preferably 5 to 18) ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 (preferably 1 to 10) carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms, a substituted or unsubstituted silyl group having 3 to 50 (preferably 3 to 20) carbon atoms; a couple of R1 and R2, and a couple of R3 and R4 may bond each other to form a saturated or unsaturated ring.
  • Specific examples of the substituted or unsubstituted alkyl group, aryl group, aralkyl group, cycloalkyl group, arylamino group, alkylamino group, heterocyclic group, silyl group and the saturated or unsaturated ring represented by R1 to R4 are the same as those exemplified as A1 to A4 above.
  • It is particularly preferable that the alkyl group represented by R2 and R4 are primary or secondary.
  • Further, examples of the substituent for A1 to A4 and R1 to R4 include a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted arylthio group having. 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 (preferably 1 to 20) carbon atoms, amino group, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, etc.
  • However, a case where all of R1 to R4 in the general formula (1) are hydrogen atoms is excluded.
  • Further in the general formula (1), it is preferable that R1 and/or R3 independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. It is preferable that R1 and R3 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • Still further in the general formula (1), it is preferable that R1 to R4 each independently represents a hydrogen atom, a substituted or unsubstituted arylamino group having 5 to 20 ring, carbon atoms; a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms or a substituted or unsubstituted silyl group having 0.3 to 50 carbon atoms.
  • Further, it is preferable that R1 and/or R3 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a s-butyl group, a t-butyl group or a cyclohexyl group.
  • Furthermore, it is preferable that R2 and/or R4 represents a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a s-butyl group, a t-butyl group or a cyclohexyl group.
  • Next, the aromatic amine derivative represented by the general formula (2) will be explained below.
  • Figure US20090189522A1-20090730-C00005
  • In the general formula (2), A5 to R8 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms;
  • In the general formula (2), R5 to R8 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 (preferably 1 to 20) carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 (preferably 5 to 20) ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 (preferably 5 to 12) ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 (preferably 1 to 10) carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20) ring carbon atoms; a couple of R5 and R6, and a couple of R7 and R8 may bond each other to form a saturated or unsaturated ring.
  • Specific examples of the groups represented by A5 to A8 and R5 to R8 in the general formula (2), specific examples of those substituent and specific examples of those saturated or unsaturated ring are the same as those exemplified as A1 to A4 and R1 to R4 in the foregoing general formula (1). Specific examples of the aromatic amine derivatives represented by the general formula (1) or the general formula (2) will be illustrated below, though not particularly limited thereto. Meanwhile, in the following compounds, Me represents a methyl group.
  • Figure US20090189522A1-20090730-C00006
    Figure US20090189522A1-20090730-C00007
    Figure US20090189522A1-20090730-C00008
    Figure US20090189522A1-20090730-C00009
    Figure US20090189522A1-20090730-C00010
    Figure US20090189522A1-20090730-C00011
    Figure US20090189522A1-20090730-C00012
    Figure US20090189522A1-20090730-C00013
    Figure US20090189522A1-20090730-C00014
    Figure US20090189522A1-20090730-C00015
    Figure US20090189522A1-20090730-C00016
    Figure US20090189522A1-20090730-C00017
    Figure US20090189522A1-20090730-C00018
    Figure US20090189522A1-20090730-C00019
    Figure US20090189522A1-20090730-C00020
    Figure US20090189522A1-20090730-C00021
    Figure US20090189522A1-20090730-C00022
    Figure US20090189522A1-20090730-C00023
    Figure US20090189522A1-20090730-C00024
    Figure US20090189522A1-20090730-C00025
    Figure US20090189522A1-20090730-C00026
    Figure US20090189522A1-20090730-C00027
    Figure US20090189522A1-20090730-C00028
  • TABLE 1
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00029
    Figure US20090189522A1-20090730-C00030
    Figure US20090189522A1-20090730-C00031
    Figure US20090189522A1-20090730-C00032
    D-1 Methyl H H H
    Figure US20090189522A1-20090730-C00033
    Figure US20090189522A1-20090730-C00034
    Figure US20090189522A1-20090730-C00035
    Figure US20090189522A1-20090730-C00036
    D-2 Methyl H H H
    Figure US20090189522A1-20090730-C00037
    Figure US20090189522A1-20090730-C00038
    Figure US20090189522A1-20090730-C00039
    Figure US20090189522A1-20090730-C00040
    D-3 Methyl H H H
    Figure US20090189522A1-20090730-C00041
    Figure US20090189522A1-20090730-C00042
    Figure US20090189522A1-20090730-C00043
    Figure US20090189522A1-20090730-C00044
    D-4 Methyl H H H
    Figure US20090189522A1-20090730-C00045
    Figure US20090189522A1-20090730-C00046
    Figure US20090189522A1-20090730-C00047
    Figure US20090189522A1-20090730-C00048
    D-5 Methyl H H H
    Figure US20090189522A1-20090730-C00049
    Figure US20090189522A1-20090730-C00050
    Figure US20090189522A1-20090730-C00051
    Figure US20090189522A1-20090730-C00052
    D-6 Methyl H H H
    Figure US20090189522A1-20090730-C00053
    Figure US20090189522A1-20090730-C00054
    Figure US20090189522A1-20090730-C00055
    Figure US20090189522A1-20090730-C00056
    D-7 Methyl H H H
    Figure US20090189522A1-20090730-C00057
    Figure US20090189522A1-20090730-C00058
    Figure US20090189522A1-20090730-C00059
    Figure US20090189522A1-20090730-C00060
    D-8 Methyl H H H
    Figure US20090189522A1-20090730-C00061
    Figure US20090189522A1-20090730-C00062
    Figure US20090189522A1-20090730-C00063
    Figure US20090189522A1-20090730-C00064
    D-9 Methyl H H H
    Figure US20090189522A1-20090730-C00065
    Figure US20090189522A1-20090730-C00066
    Figure US20090189522A1-20090730-C00067
    Figure US20090189522A1-20090730-C00068
    D-10 Methyl H H H
    Figure US20090189522A1-20090730-C00069
    Figure US20090189522A1-20090730-C00070
    Figure US20090189522A1-20090730-C00071
    Figure US20090189522A1-20090730-C00072
    D-11 Methyl H H H
    Figure US20090189522A1-20090730-C00073
    Figure US20090189522A1-20090730-C00074
    Figure US20090189522A1-20090730-C00075
    Figure US20090189522A1-20090730-C00076
    D-12 Methyl H H H
    Figure US20090189522A1-20090730-C00077
    Figure US20090189522A1-20090730-C00078
    Figure US20090189522A1-20090730-C00079
    Figure US20090189522A1-20090730-C00080
  • TABLE 2
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00081
    Figure US20090189522A1-20090730-C00082
    Figure US20090189522A1-20090730-C00083
    Figure US20090189522A1-20090730-C00084
    D-13 Methyl H H H
    Figure US20090189522A1-20090730-C00085
    Figure US20090189522A1-20090730-C00086
    Figure US20090189522A1-20090730-C00087
    Figure US20090189522A1-20090730-C00088
    D-14 Methyl H H H
    Figure US20090189522A1-20090730-C00089
    Figure US20090189522A1-20090730-C00090
    Figure US20090189522A1-20090730-C00091
    Figure US20090189522A1-20090730-C00092
    D-15 Methyl H H H
    Figure US20090189522A1-20090730-C00093
    Figure US20090189522A1-20090730-C00094
    Figure US20090189522A1-20090730-C00095
    Figure US20090189522A1-20090730-C00096
    D-16 Methyl H H H
    Figure US20090189522A1-20090730-C00097
    Figure US20090189522A1-20090730-C00098
    Figure US20090189522A1-20090730-C00099
    Figure US20090189522A1-20090730-C00100
    D-17 Methyl H H H
    Figure US20090189522A1-20090730-C00101
    Figure US20090189522A1-20090730-C00102
    Figure US20090189522A1-20090730-C00103
    Figure US20090189522A1-20090730-C00104
    D-18 Methyl H H H
    Figure US20090189522A1-20090730-C00105
    Figure US20090189522A1-20090730-C00106
    Figure US20090189522A1-20090730-C00107
    Figure US20090189522A1-20090730-C00108
    D-19 Methyl H H H
    Figure US20090189522A1-20090730-C00109
    Figure US20090189522A1-20090730-C00110
    Figure US20090189522A1-20090730-C00111
    Figure US20090189522A1-20090730-C00112
    D-20 Methyl H H H
    Figure US20090189522A1-20090730-C00113
    Figure US20090189522A1-20090730-C00114
    Figure US20090189522A1-20090730-C00115
    Figure US20090189522A1-20090730-C00116
    D-21 Methyl H H H
    Figure US20090189522A1-20090730-C00117
    Figure US20090189522A1-20090730-C00118
    Figure US20090189522A1-20090730-C00119
    Figure US20090189522A1-20090730-C00120
    D-22 Methyl H H H
    Figure US20090189522A1-20090730-C00121
    Figure US20090189522A1-20090730-C00122
    Figure US20090189522A1-20090730-C00123
    Figure US20090189522A1-20090730-C00124
    D-23 Methyl H H H
    Figure US20090189522A1-20090730-C00125
    Figure US20090189522A1-20090730-C00126
    Figure US20090189522A1-20090730-C00127
    Figure US20090189522A1-20090730-C00128
    D-24 Methyl H H H
    Figure US20090189522A1-20090730-C00129
    Figure US20090189522A1-20090730-C00130
    Figure US20090189522A1-20090730-C00131
    Figure US20090189522A1-20090730-C00132
  • TABLE 3
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00133
    Figure US20090189522A1-20090730-C00134
    Figure US20090189522A1-20090730-C00135
    Figure US20090189522A1-20090730-C00136
    D-25 Methyl H H H
    Figure US20090189522A1-20090730-C00137
    Figure US20090189522A1-20090730-C00138
    Figure US20090189522A1-20090730-C00139
    Figure US20090189522A1-20090730-C00140
    D-26 Methyl H H H
    Figure US20090189522A1-20090730-C00141
    Figure US20090189522A1-20090730-C00142
    Figure US20090189522A1-20090730-C00143
    Figure US20090189522A1-20090730-C00144
    D-27 Methyl H H H
    Figure US20090189522A1-20090730-C00145
    Figure US20090189522A1-20090730-C00146
    Figure US20090189522A1-20090730-C00147
    Figure US20090189522A1-20090730-C00148
    D-28 Methyl H H H
    Figure US20090189522A1-20090730-C00149
    Figure US20090189522A1-20090730-C00150
    Figure US20090189522A1-20090730-C00151
    Figure US20090189522A1-20090730-C00152
    D-29 Methyl H H H
    Figure US20090189522A1-20090730-C00153
    Figure US20090189522A1-20090730-C00154
    Figure US20090189522A1-20090730-C00155
    Figure US20090189522A1-20090730-C00156
    D-30 Methyl H H H
    Figure US20090189522A1-20090730-C00157
    Figure US20090189522A1-20090730-C00158
    Figure US20090189522A1-20090730-C00159
    Figure US20090189522A1-20090730-C00160
    D-31 Methyl H H H
    Figure US20090189522A1-20090730-C00161
    Figure US20090189522A1-20090730-C00162
    Figure US20090189522A1-20090730-C00163
    Figure US20090189522A1-20090730-C00164
    D-32 Methyl H H H
    Figure US20090189522A1-20090730-C00165
    Figure US20090189522A1-20090730-C00166
    Figure US20090189522A1-20090730-C00167
    Figure US20090189522A1-20090730-C00168
    D-33 Methyl H H H
    Figure US20090189522A1-20090730-C00169
    Figure US20090189522A1-20090730-C00170
    Figure US20090189522A1-20090730-C00171
    Figure US20090189522A1-20090730-C00172
    D-34 Methyl H H H
    Figure US20090189522A1-20090730-C00173
    Figure US20090189522A1-20090730-C00174
    Figure US20090189522A1-20090730-C00175
    Figure US20090189522A1-20090730-C00176
    D-35 Methyl H H H
    Figure US20090189522A1-20090730-C00177
    Figure US20090189522A1-20090730-C00178
    Figure US20090189522A1-20090730-C00179
    Figure US20090189522A1-20090730-C00180
    D-36 Methyl H H H
    Figure US20090189522A1-20090730-C00181
    Figure US20090189522A1-20090730-C00182
    Figure US20090189522A1-20090730-C00183
    Figure US20090189522A1-20090730-C00184
  • TABLE 4
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00185
    Figure US20090189522A1-20090730-C00186
    Figure US20090189522A1-20090730-C00187
    Figure US20090189522A1-20090730-C00188
    D-37 Methyl H H H
    Figure US20090189522A1-20090730-C00189
    Figure US20090189522A1-20090730-C00190
    Figure US20090189522A1-20090730-C00191
    Figure US20090189522A1-20090730-C00192
    D-38 Methyl H H H
    Figure US20090189522A1-20090730-C00193
    Figure US20090189522A1-20090730-C00194
    Figure US20090189522A1-20090730-C00195
    Figure US20090189522A1-20090730-C00196
    D-39 Methyl H H H
    Figure US20090189522A1-20090730-C00197
    Figure US20090189522A1-20090730-C00198
    Figure US20090189522A1-20090730-C00199
    Figure US20090189522A1-20090730-C00200
    D-40 Methyl H H H
    Figure US20090189522A1-20090730-C00201
    Figure US20090189522A1-20090730-C00202
    Figure US20090189522A1-20090730-C00203
    Figure US20090189522A1-20090730-C00204
    D-41 Methyl H H H
    Figure US20090189522A1-20090730-C00205
    Figure US20090189522A1-20090730-C00206
    Figure US20090189522A1-20090730-C00207
    Figure US20090189522A1-20090730-C00208
    D-42 Methyl H H H
    Figure US20090189522A1-20090730-C00209
    Figure US20090189522A1-20090730-C00210
    Figure US20090189522A1-20090730-C00211
    Figure US20090189522A1-20090730-C00212
    D-43 Methyl H H H
    Figure US20090189522A1-20090730-C00213
    Figure US20090189522A1-20090730-C00214
    Figure US20090189522A1-20090730-C00215
    Figure US20090189522A1-20090730-C00216
    D-44 Methyl H H H
    Figure US20090189522A1-20090730-C00217
    Figure US20090189522A1-20090730-C00218
    Figure US20090189522A1-20090730-C00219
    Figure US20090189522A1-20090730-C00220
    D-45 Methyl H H H
    Figure US20090189522A1-20090730-C00221
    Figure US20090189522A1-20090730-C00222
    Figure US20090189522A1-20090730-C00223
    Figure US20090189522A1-20090730-C00224
    D-46 Methyl H H H
    Figure US20090189522A1-20090730-C00225
    Figure US20090189522A1-20090730-C00226
    Figure US20090189522A1-20090730-C00227
    Figure US20090189522A1-20090730-C00228
    D-47 Methyl H H H
    Figure US20090189522A1-20090730-C00229
    Figure US20090189522A1-20090730-C00230
    Figure US20090189522A1-20090730-C00231
    Figure US20090189522A1-20090730-C00232
    D-48 Methyl H H H
    Figure US20090189522A1-20090730-C00233
    Figure US20090189522A1-20090730-C00234
    Figure US20090189522A1-20090730-C00235
    Figure US20090189522A1-20090730-C00236
  • TABLE 5
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00237
    Figure US20090189522A1-20090730-C00238
    Figure US20090189522A1-20090730-C00239
    Figure US20090189522A1-20090730-C00240
    D-49 Isopropyl H H H
    Figure US20090189522A1-20090730-C00241
    Figure US20090189522A1-20090730-C00242
    Figure US20090189522A1-20090730-C00243
    Figure US20090189522A1-20090730-C00244
    D-50 Isopropyl H H H
    Figure US20090189522A1-20090730-C00245
    Figure US20090189522A1-20090730-C00246
    Figure US20090189522A1-20090730-C00247
    Figure US20090189522A1-20090730-C00248
    D-51 Isopropyl H H H
    Figure US20090189522A1-20090730-C00249
    Figure US20090189522A1-20090730-C00250
    Figure US20090189522A1-20090730-C00251
    Figure US20090189522A1-20090730-C00252
    D-52 Isopropyl H H H
    Figure US20090189522A1-20090730-C00253
    Figure US20090189522A1-20090730-C00254
    Figure US20090189522A1-20090730-C00255
    Figure US20090189522A1-20090730-C00256
    D-53 Isopropyl H H H
    Figure US20090189522A1-20090730-C00257
    Figure US20090189522A1-20090730-C00258
    Figure US20090189522A1-20090730-C00259
    Figure US20090189522A1-20090730-C00260
    D-54 Isopropyl H H H
    Figure US20090189522A1-20090730-C00261
    Figure US20090189522A1-20090730-C00262
    Figure US20090189522A1-20090730-C00263
    Figure US20090189522A1-20090730-C00264
    D-55 Isopropyl H H H
    Figure US20090189522A1-20090730-C00265
    Figure US20090189522A1-20090730-C00266
    Figure US20090189522A1-20090730-C00267
    Figure US20090189522A1-20090730-C00268
    D-56 Isopropyl H H H
    Figure US20090189522A1-20090730-C00269
    Figure US20090189522A1-20090730-C00270
    Figure US20090189522A1-20090730-C00271
    Figure US20090189522A1-20090730-C00272
    D-57 Isopropyl H H H
    Figure US20090189522A1-20090730-C00273
    Figure US20090189522A1-20090730-C00274
    Figure US20090189522A1-20090730-C00275
    Figure US20090189522A1-20090730-C00276
    D-58 Isopropyl H H H
    Figure US20090189522A1-20090730-C00277
    Figure US20090189522A1-20090730-C00278
    Figure US20090189522A1-20090730-C00279
    Figure US20090189522A1-20090730-C00280
    D-59 Isopropyl H H H
    Figure US20090189522A1-20090730-C00281
    Figure US20090189522A1-20090730-C00282
    Figure US20090189522A1-20090730-C00283
    Figure US20090189522A1-20090730-C00284
    D-60 Isopropyl H H H
    Figure US20090189522A1-20090730-C00285
    Figure US20090189522A1-20090730-C00286
    Figure US20090189522A1-20090730-C00287
    Figure US20090189522A1-20090730-C00288
  • TABLE 6
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00289
    Figure US20090189522A1-20090730-C00290
    Figure US20090189522A1-20090730-C00291
    Figure US20090189522A1-20090730-C00292
    D-61 Isopropyl H H H
    Figure US20090189522A1-20090730-C00293
    Figure US20090189522A1-20090730-C00294
    Figure US20090189522A1-20090730-C00295
    Figure US20090189522A1-20090730-C00296
    D-62 Isopropyl H H H
    Figure US20090189522A1-20090730-C00297
    Figure US20090189522A1-20090730-C00298
    Figure US20090189522A1-20090730-C00299
    Figure US20090189522A1-20090730-C00300
    D-63 Isopropyl H H H
    Figure US20090189522A1-20090730-C00301
    Figure US20090189522A1-20090730-C00302
    Figure US20090189522A1-20090730-C00303
    Figure US20090189522A1-20090730-C00304
    D-64 Isopropyl H H H
    Figure US20090189522A1-20090730-C00305
    Figure US20090189522A1-20090730-C00306
    Figure US20090189522A1-20090730-C00307
    Figure US20090189522A1-20090730-C00308
    D-65 Isopropyl H H H
    Figure US20090189522A1-20090730-C00309
    Figure US20090189522A1-20090730-C00310
    Figure US20090189522A1-20090730-C00311
    Figure US20090189522A1-20090730-C00312
    D-66 Isopropyl H H H
    Figure US20090189522A1-20090730-C00313
    Figure US20090189522A1-20090730-C00314
    Figure US20090189522A1-20090730-C00315
    Figure US20090189522A1-20090730-C00316
    D-67 Isopropyl H H H
    Figure US20090189522A1-20090730-C00317
    Figure US20090189522A1-20090730-C00318
    Figure US20090189522A1-20090730-C00319
    Figure US20090189522A1-20090730-C00320
    D-68 Isopropyl H H H
    Figure US20090189522A1-20090730-C00321
    Figure US20090189522A1-20090730-C00322
    Figure US20090189522A1-20090730-C00323
    Figure US20090189522A1-20090730-C00324
    D-69 Isopropyl H H H
    Figure US20090189522A1-20090730-C00325
    Figure US20090189522A1-20090730-C00326
    Figure US20090189522A1-20090730-C00327
    Figure US20090189522A1-20090730-C00328
    D-70 Isopropyl H H H
    Figure US20090189522A1-20090730-C00329
    Figure US20090189522A1-20090730-C00330
    Figure US20090189522A1-20090730-C00331
    Figure US20090189522A1-20090730-C00332
    D-71 Isopropyl H H H
    Figure US20090189522A1-20090730-C00333
    Figure US20090189522A1-20090730-C00334
    Figure US20090189522A1-20090730-C00335
    Figure US20090189522A1-20090730-C00336
    D-72 Isopropyl H H H
    Figure US20090189522A1-20090730-C00337
    Figure US20090189522A1-20090730-C00338
    Figure US20090189522A1-20090730-C00339
    Figure US20090189522A1-20090730-C00340
  • TABLE 7
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00341
    Figure US20090189522A1-20090730-C00342
    Figure US20090189522A1-20090730-C00343
    Figure US20090189522A1-20090730-C00344
    D-73 Isopropyl H H H
    Figure US20090189522A1-20090730-C00345
    Figure US20090189522A1-20090730-C00346
    Figure US20090189522A1-20090730-C00347
    Figure US20090189522A1-20090730-C00348
    D-74 Isopropyl H H H
    Figure US20090189522A1-20090730-C00349
    Figure US20090189522A1-20090730-C00350
    Figure US20090189522A1-20090730-C00351
    Figure US20090189522A1-20090730-C00352
    D-75 Isopropyl H H H
    Figure US20090189522A1-20090730-C00353
    Figure US20090189522A1-20090730-C00354
    Figure US20090189522A1-20090730-C00355
    Figure US20090189522A1-20090730-C00356
    D-76 Isopropyl H H H
    Figure US20090189522A1-20090730-C00357
    Figure US20090189522A1-20090730-C00358
    Figure US20090189522A1-20090730-C00359
    Figure US20090189522A1-20090730-C00360
    D-77 Isopropyl H H H
    Figure US20090189522A1-20090730-C00361
    Figure US20090189522A1-20090730-C00362
    Figure US20090189522A1-20090730-C00363
    Figure US20090189522A1-20090730-C00364
    D-78 Isopropyl H H H
    Figure US20090189522A1-20090730-C00365
    Figure US20090189522A1-20090730-C00366
    Figure US20090189522A1-20090730-C00367
    Figure US20090189522A1-20090730-C00368
    D-79 Isopropyl H H H
    Figure US20090189522A1-20090730-C00369
    Figure US20090189522A1-20090730-C00370
    Figure US20090189522A1-20090730-C00371
    Figure US20090189522A1-20090730-C00372
    D-80 Isopropyl H H H
    Figure US20090189522A1-20090730-C00373
    Figure US20090189522A1-20090730-C00374
    Figure US20090189522A1-20090730-C00375
    Figure US20090189522A1-20090730-C00376
    D-81 Isopropyl H H H
    Figure US20090189522A1-20090730-C00377
    Figure US20090189522A1-20090730-C00378
    Figure US20090189522A1-20090730-C00379
    Figure US20090189522A1-20090730-C00380
    D-82 Isopropyl H H H
    Figure US20090189522A1-20090730-C00381
    Figure US20090189522A1-20090730-C00382
    Figure US20090189522A1-20090730-C00383
    Figure US20090189522A1-20090730-C00384
    D-83 Isopropyl H H H
    Figure US20090189522A1-20090730-C00385
    Figure US20090189522A1-20090730-C00386
    Figure US20090189522A1-20090730-C00387
    Figure US20090189522A1-20090730-C00388
    D-84 Isopropyl H H H
    Figure US20090189522A1-20090730-C00389
    Figure US20090189522A1-20090730-C00390
    Figure US20090189522A1-20090730-C00391
    Figure US20090189522A1-20090730-C00392
  • TABLE 8
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00393
    Figure US20090189522A1-20090730-C00394
    Figure US20090189522A1-20090730-C00395
    Figure US20090189522A1-20090730-C00396
    D-85 Isopropyl H H H
    Figure US20090189522A1-20090730-C00397
    Figure US20090189522A1-20090730-C00398
    Figure US20090189522A1-20090730-C00399
    Figure US20090189522A1-20090730-C00400
    D-86 Isopropyl H H H
    Figure US20090189522A1-20090730-C00401
    Figure US20090189522A1-20090730-C00402
    Figure US20090189522A1-20090730-C00403
    Figure US20090189522A1-20090730-C00404
    D-87 Isopropyl H H H
    Figure US20090189522A1-20090730-C00405
    Figure US20090189522A1-20090730-C00406
    Figure US20090189522A1-20090730-C00407
    Figure US20090189522A1-20090730-C00408
    D-88 Isopropyl H H H
    Figure US20090189522A1-20090730-C00409
    Figure US20090189522A1-20090730-C00410
    Figure US20090189522A1-20090730-C00411
    Figure US20090189522A1-20090730-C00412
    D-89 Isopropyl H H H
    Figure US20090189522A1-20090730-C00413
    Figure US20090189522A1-20090730-C00414
    Figure US20090189522A1-20090730-C00415
    Figure US20090189522A1-20090730-C00416
    D-90 Isopropyl H H H
    Figure US20090189522A1-20090730-C00417
    Figure US20090189522A1-20090730-C00418
    Figure US20090189522A1-20090730-C00419
    Figure US20090189522A1-20090730-C00420
    D-91 Isopropyl H H H
    Figure US20090189522A1-20090730-C00421
    Figure US20090189522A1-20090730-C00422
    Figure US20090189522A1-20090730-C00423
    Figure US20090189522A1-20090730-C00424
    D-92 Isopropyl H H H
    Figure US20090189522A1-20090730-C00425
    Figure US20090189522A1-20090730-C00426
    Figure US20090189522A1-20090730-C00427
    Figure US20090189522A1-20090730-C00428
    D-93 Isopropyl H H H
    Figure US20090189522A1-20090730-C00429
    Figure US20090189522A1-20090730-C00430
    Figure US20090189522A1-20090730-C00431
    Figure US20090189522A1-20090730-C00432
    D-94 Isopropyl H H H
    Figure US20090189522A1-20090730-C00433
    Figure US20090189522A1-20090730-C00434
    Figure US20090189522A1-20090730-C00435
    Figure US20090189522A1-20090730-C00436
    D-95 Isopropyl H H H
    Figure US20090189522A1-20090730-C00437
    Figure US20090189522A1-20090730-C00438
    Figure US20090189522A1-20090730-C00439
    Figure US20090189522A1-20090730-C00440
    D-96 Isopropyl H H H
    Figure US20090189522A1-20090730-C00441
    Figure US20090189522A1-20090730-C00442
    Figure US20090189522A1-20090730-C00443
    Figure US20090189522A1-20090730-C00444
  • TABLE 9
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00445
    Figure US20090189522A1-20090730-C00446
    Figure US20090189522A1-20090730-C00447
    Figure US20090189522A1-20090730-C00448
    D-97 t-butyl H H H
    Figure US20090189522A1-20090730-C00449
    Figure US20090189522A1-20090730-C00450
    Figure US20090189522A1-20090730-C00451
    Figure US20090189522A1-20090730-C00452
    D-98 t-butyl H H H
    Figure US20090189522A1-20090730-C00453
    Figure US20090189522A1-20090730-C00454
    Figure US20090189522A1-20090730-C00455
    Figure US20090189522A1-20090730-C00456
    D-99 t-butyl H H H
    Figure US20090189522A1-20090730-C00457
    Figure US20090189522A1-20090730-C00458
    Figure US20090189522A1-20090730-C00459
    Figure US20090189522A1-20090730-C00460
    D-100 t-butyl H H H
    Figure US20090189522A1-20090730-C00461
    Figure US20090189522A1-20090730-C00462
    Figure US20090189522A1-20090730-C00463
    Figure US20090189522A1-20090730-C00464
    D-101 t-butyl H H H
    Figure US20090189522A1-20090730-C00465
    Figure US20090189522A1-20090730-C00466
    Figure US20090189522A1-20090730-C00467
    Figure US20090189522A1-20090730-C00468
    D-102 t-butyl H H H
    Figure US20090189522A1-20090730-C00469
    Figure US20090189522A1-20090730-C00470
    Figure US20090189522A1-20090730-C00471
    Figure US20090189522A1-20090730-C00472
    D-103 t-butyl H H H
    Figure US20090189522A1-20090730-C00473
    Figure US20090189522A1-20090730-C00474
    Figure US20090189522A1-20090730-C00475
    Figure US20090189522A1-20090730-C00476
    D-104 t-butyl H H H
    Figure US20090189522A1-20090730-C00477
    Figure US20090189522A1-20090730-C00478
    Figure US20090189522A1-20090730-C00479
    Figure US20090189522A1-20090730-C00480
    D-105 t-butyl H H H
    Figure US20090189522A1-20090730-C00481
    Figure US20090189522A1-20090730-C00482
    Figure US20090189522A1-20090730-C00483
    Figure US20090189522A1-20090730-C00484
    D-106 t-butyl H H H
    Figure US20090189522A1-20090730-C00485
    Figure US20090189522A1-20090730-C00486
    Figure US20090189522A1-20090730-C00487
    Figure US20090189522A1-20090730-C00488
    D-107 t-butyl H H H
    Figure US20090189522A1-20090730-C00489
    Figure US20090189522A1-20090730-C00490
    Figure US20090189522A1-20090730-C00491
    Figure US20090189522A1-20090730-C00492
    D-108 t-butyl H H H
    Figure US20090189522A1-20090730-C00493
    Figure US20090189522A1-20090730-C00494
    Figure US20090189522A1-20090730-C00495
    Figure US20090189522A1-20090730-C00496
  • TABLE 10
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00497
    Figure US20090189522A1-20090730-C00498
    Figure US20090189522A1-20090730-C00499
    Figure US20090189522A1-20090730-C00500
    D-109 t-butyl H H H
    Figure US20090189522A1-20090730-C00501
    Figure US20090189522A1-20090730-C00502
    Figure US20090189522A1-20090730-C00503
    Figure US20090189522A1-20090730-C00504
    D-110 t-butyl H H H
    Figure US20090189522A1-20090730-C00505
    Figure US20090189522A1-20090730-C00506
    Figure US20090189522A1-20090730-C00507
    Figure US20090189522A1-20090730-C00508
    D-111 t-butyl H H H
    Figure US20090189522A1-20090730-C00509
    Figure US20090189522A1-20090730-C00510
    Figure US20090189522A1-20090730-C00511
    Figure US20090189522A1-20090730-C00512
    D-112 t-butyl H H H
    Figure US20090189522A1-20090730-C00513
    Figure US20090189522A1-20090730-C00514
    Figure US20090189522A1-20090730-C00515
    Figure US20090189522A1-20090730-C00516
    D-113 t-butyl H H H
    Figure US20090189522A1-20090730-C00517
    Figure US20090189522A1-20090730-C00518
    Figure US20090189522A1-20090730-C00519
    Figure US20090189522A1-20090730-C00520
    D-114 t-butyl H H H
    Figure US20090189522A1-20090730-C00521
    Figure US20090189522A1-20090730-C00522
    Figure US20090189522A1-20090730-C00523
    Figure US20090189522A1-20090730-C00524
    D-115 t-butyl H H H
    Figure US20090189522A1-20090730-C00525
    Figure US20090189522A1-20090730-C00526
    Figure US20090189522A1-20090730-C00527
    Figure US20090189522A1-20090730-C00528
    D-116 t-butyl H H H
    Figure US20090189522A1-20090730-C00529
    Figure US20090189522A1-20090730-C00530
    Figure US20090189522A1-20090730-C00531
    Figure US20090189522A1-20090730-C00532
    D-117 t-butyl H H H
    Figure US20090189522A1-20090730-C00533
    Figure US20090189522A1-20090730-C00534
    Figure US20090189522A1-20090730-C00535
    Figure US20090189522A1-20090730-C00536
    D-118 t-butyl H H H
    Figure US20090189522A1-20090730-C00537
    Figure US20090189522A1-20090730-C00538
    Figure US20090189522A1-20090730-C00539
    Figure US20090189522A1-20090730-C00540
    D-119 t-butyl H H H
    Figure US20090189522A1-20090730-C00541
    Figure US20090189522A1-20090730-C00542
    Figure US20090189522A1-20090730-C00543
    Figure US20090189522A1-20090730-C00544
    D-120 t-butyl H H H
    Figure US20090189522A1-20090730-C00545
    Figure US20090189522A1-20090730-C00546
    Figure US20090189522A1-20090730-C00547
    Figure US20090189522A1-20090730-C00548
  • TABLE 11
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00549
    Figure US20090189522A1-20090730-C00550
    Figure US20090189522A1-20090730-C00551
    Figure US20090189522A1-20090730-C00552
    D-121 t-butyl H H H
    Figure US20090189522A1-20090730-C00553
    Figure US20090189522A1-20090730-C00554
    Figure US20090189522A1-20090730-C00555
    Figure US20090189522A1-20090730-C00556
    D-122 t-butyl H H H
    Figure US20090189522A1-20090730-C00557
    Figure US20090189522A1-20090730-C00558
    Figure US20090189522A1-20090730-C00559
    Figure US20090189522A1-20090730-C00560
    D-123 t-butyl H H H
    Figure US20090189522A1-20090730-C00561
    Figure US20090189522A1-20090730-C00562
    Figure US20090189522A1-20090730-C00563
    Figure US20090189522A1-20090730-C00564
    D-124 t-butyl H H H
    Figure US20090189522A1-20090730-C00565
    Figure US20090189522A1-20090730-C00566
    Figure US20090189522A1-20090730-C00567
    Figure US20090189522A1-20090730-C00568
    D-125 t-butyl H H H
    Figure US20090189522A1-20090730-C00569
    Figure US20090189522A1-20090730-C00570
    Figure US20090189522A1-20090730-C00571
    Figure US20090189522A1-20090730-C00572
    D-126 t-butyl H H H
    Figure US20090189522A1-20090730-C00573
    Figure US20090189522A1-20090730-C00574
    Figure US20090189522A1-20090730-C00575
    Figure US20090189522A1-20090730-C00576
    D-127 t-butyl H H H
    Figure US20090189522A1-20090730-C00577
    Figure US20090189522A1-20090730-C00578
    Figure US20090189522A1-20090730-C00579
    Figure US20090189522A1-20090730-C00580
    D-128 t-butyl H H H
    Figure US20090189522A1-20090730-C00581
    Figure US20090189522A1-20090730-C00582
    Figure US20090189522A1-20090730-C00583
    Figure US20090189522A1-20090730-C00584
    D-129 t-butyl H H H
    Figure US20090189522A1-20090730-C00585
    Figure US20090189522A1-20090730-C00586
    Figure US20090189522A1-20090730-C00587
    Figure US20090189522A1-20090730-C00588
    D-130 t-butyl H H H
    Figure US20090189522A1-20090730-C00589
    Figure US20090189522A1-20090730-C00590
    Figure US20090189522A1-20090730-C00591
    Figure US20090189522A1-20090730-C00592
    D-131 t-butyl H H H
    Figure US20090189522A1-20090730-C00593
    Figure US20090189522A1-20090730-C00594
    Figure US20090189522A1-20090730-C00595
    Figure US20090189522A1-20090730-C00596
    D-132 t-butyl H H H
    Figure US20090189522A1-20090730-C00597
    Figure US20090189522A1-20090730-C00598
    Figure US20090189522A1-20090730-C00599
    Figure US20090189522A1-20090730-C00600
  • TABLE 12
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00601
    Figure US20090189522A1-20090730-C00602
    Figure US20090189522A1-20090730-C00603
    Figure US20090189522A1-20090730-C00604
    D-133 t-butyl H H H
    Figure US20090189522A1-20090730-C00605
    Figure US20090189522A1-20090730-C00606
    Figure US20090189522A1-20090730-C00607
    Figure US20090189522A1-20090730-C00608
    D-134 t-butyl H H H
    Figure US20090189522A1-20090730-C00609
    Figure US20090189522A1-20090730-C00610
    Figure US20090189522A1-20090730-C00611
    Figure US20090189522A1-20090730-C00612
    D-135 t-butyl H H H
    Figure US20090189522A1-20090730-C00613
    Figure US20090189522A1-20090730-C00614
    Figure US20090189522A1-20090730-C00615
    Figure US20090189522A1-20090730-C00616
    D-136 t-butyl H H H
    Figure US20090189522A1-20090730-C00617
    Figure US20090189522A1-20090730-C00618
    Figure US20090189522A1-20090730-C00619
    Figure US20090189522A1-20090730-C00620
    D-137 t-butyl H H H
    Figure US20090189522A1-20090730-C00621
    Figure US20090189522A1-20090730-C00622
    Figure US20090189522A1-20090730-C00623
    Figure US20090189522A1-20090730-C00624
    D-138 t-butyl H H H
    Figure US20090189522A1-20090730-C00625
    Figure US20090189522A1-20090730-C00626
    Figure US20090189522A1-20090730-C00627
    Figure US20090189522A1-20090730-C00628
    D-139 t-butyl H H H
    Figure US20090189522A1-20090730-C00629
    Figure US20090189522A1-20090730-C00630
    Figure US20090189522A1-20090730-C00631
    Figure US20090189522A1-20090730-C00632
    D-140 t-butyl H H H
    Figure US20090189522A1-20090730-C00633
    Figure US20090189522A1-20090730-C00634
    Figure US20090189522A1-20090730-C00635
    Figure US20090189522A1-20090730-C00636
    D-141 t-butyl H H H
    Figure US20090189522A1-20090730-C00637
    Figure US20090189522A1-20090730-C00638
    Figure US20090189522A1-20090730-C00639
    Figure US20090189522A1-20090730-C00640
    D-142 t-butyl H H H
    Figure US20090189522A1-20090730-C00641
    Figure US20090189522A1-20090730-C00642
    Figure US20090189522A1-20090730-C00643
    Figure US20090189522A1-20090730-C00644
    D-143 t-butyl H H H
    Figure US20090189522A1-20090730-C00645
    Figure US20090189522A1-20090730-C00646
    Figure US20090189522A1-20090730-C00647
    Figure US20090189522A1-20090730-C00648
    D-144 t-butyl H H H
    Figure US20090189522A1-20090730-C00649
    Figure US20090189522A1-20090730-C00650
    Figure US20090189522A1-20090730-C00651
    Figure US20090189522A1-20090730-C00652
  • TABLE 13
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00653
    Figure US20090189522A1-20090730-C00654
    Figure US20090189522A1-20090730-C00655
    Figure US20090189522A1-20090730-C00656
    D-145 Phenyl H H H
    Figure US20090189522A1-20090730-C00657
    Figure US20090189522A1-20090730-C00658
    Figure US20090189522A1-20090730-C00659
    Figure US20090189522A1-20090730-C00660
    D-146 Phenyl H H H
    Figure US20090189522A1-20090730-C00661
    Figure US20090189522A1-20090730-C00662
    Figure US20090189522A1-20090730-C00663
    Figure US20090189522A1-20090730-C00664
    D-147 Phenyl H H H
    Figure US20090189522A1-20090730-C00665
    Figure US20090189522A1-20090730-C00666
    Figure US20090189522A1-20090730-C00667
    Figure US20090189522A1-20090730-C00668
    D-148 Phenyl H H H
    Figure US20090189522A1-20090730-C00669
    Figure US20090189522A1-20090730-C00670
    Figure US20090189522A1-20090730-C00671
    Figure US20090189522A1-20090730-C00672
    D-149 Phenyl H H H
    Figure US20090189522A1-20090730-C00673
    Figure US20090189522A1-20090730-C00674
    Figure US20090189522A1-20090730-C00675
    Figure US20090189522A1-20090730-C00676
    D-150 Phenyl H H H
    Figure US20090189522A1-20090730-C00677
    Figure US20090189522A1-20090730-C00678
    Figure US20090189522A1-20090730-C00679
    Figure US20090189522A1-20090730-C00680
    D-151 Phenyl H H H
    Figure US20090189522A1-20090730-C00681
    Figure US20090189522A1-20090730-C00682
    Figure US20090189522A1-20090730-C00683
    Figure US20090189522A1-20090730-C00684
    D-152 Phenyl H H H
    Figure US20090189522A1-20090730-C00685
    Figure US20090189522A1-20090730-C00686
    Figure US20090189522A1-20090730-C00687
    Figure US20090189522A1-20090730-C00688
    D-153 Phenyl H H H
    Figure US20090189522A1-20090730-C00689
    Figure US20090189522A1-20090730-C00690
    Figure US20090189522A1-20090730-C00691
    Figure US20090189522A1-20090730-C00692
    D-154 Phenyl H H H
    Figure US20090189522A1-20090730-C00693
    Figure US20090189522A1-20090730-C00694
    Figure US20090189522A1-20090730-C00695
    Figure US20090189522A1-20090730-C00696
    D-155 Phenyl H H H
    Figure US20090189522A1-20090730-C00697
    Figure US20090189522A1-20090730-C00698
    Figure US20090189522A1-20090730-C00699
    Figure US20090189522A1-20090730-C00700
    D-156 Phenyl H H H
    Figure US20090189522A1-20090730-C00701
    Figure US20090189522A1-20090730-C00702
    Figure US20090189522A1-20090730-C00703
    Figure US20090189522A1-20090730-C00704
  • TABLE 14
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00705
    Figure US20090189522A1-20090730-C00706
    Figure US20090189522A1-20090730-C00707
    Figure US20090189522A1-20090730-C00708
    D-157 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00709
    Figure US20090189522A1-20090730-C00710
    Figure US20090189522A1-20090730-C00711
    Figure US20090189522A1-20090730-C00712
    D-158 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00713
    Figure US20090189522A1-20090730-C00714
    Figure US20090189522A1-20090730-C00715
    Figure US20090189522A1-20090730-C00716
    D-159 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00717
    Figure US20090189522A1-20090730-C00718
    Figure US20090189522A1-20090730-C00719
    Figure US20090189522A1-20090730-C00720
    D-160 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00721
    Figure US20090189522A1-20090730-C00722
    Figure US20090189522A1-20090730-C00723
    Figure US20090189522A1-20090730-C00724
    D-161 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00725
    Figure US20090189522A1-20090730-C00726
    Figure US20090189522A1-20090730-C00727
    Figure US20090189522A1-20090730-C00728
    D-162 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00729
    Figure US20090189522A1-20090730-C00730
    Figure US20090189522A1-20090730-C00731
    Figure US20090189522A1-20090730-C00732
    D-163 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00733
    Figure US20090189522A1-20090730-C00734
    Figure US20090189522A1-20090730-C00735
    Figure US20090189522A1-20090730-C00736
    D-164 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00737
    Figure US20090189522A1-20090730-C00738
    Figure US20090189522A1-20090730-C00739
    Figure US20090189522A1-20090730-C00740
    D-165 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00741
    Figure US20090189522A1-20090730-C00742
    Figure US20090189522A1-20090730-C00743
    Figure US20090189522A1-20090730-C00744
    D-166 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00745
    Figure US20090189522A1-20090730-C00746
    Figure US20090189522A1-20090730-C00747
    Figure US20090189522A1-20090730-C00748
    D-167 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00749
    Figure US20090189522A1-20090730-C00750
    Figure US20090189522A1-20090730-C00751
    Figure US20090189522A1-20090730-C00752
    D-168 1-naphtyl H H H
    Figure US20090189522A1-20090730-C00753
    Figure US20090189522A1-20090730-C00754
    Figure US20090189522A1-20090730-C00755
    Figure US20090189522A1-20090730-C00756
  • TABLE 15
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00757
    Figure US20090189522A1-20090730-C00758
    Figure US20090189522A1-20090730-C00759
    Figure US20090189522A1-20090730-C00760
    D-169 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00761
    Figure US20090189522A1-20090730-C00762
    Figure US20090189522A1-20090730-C00763
    Figure US20090189522A1-20090730-C00764
    D-170 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00765
    Figure US20090189522A1-20090730-C00766
    Figure US20090189522A1-20090730-C00767
    Figure US20090189522A1-20090730-C00768
    D-171 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00769
    Figure US20090189522A1-20090730-C00770
    Figure US20090189522A1-20090730-C00771
    Figure US20090189522A1-20090730-C00772
    D-172 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00773
    Figure US20090189522A1-20090730-C00774
    Figure US20090189522A1-20090730-C00775
    Figure US20090189522A1-20090730-C00776
    D-173 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00777
    Figure US20090189522A1-20090730-C00778
    Figure US20090189522A1-20090730-C00779
    Figure US20090189522A1-20090730-C00780
    D-174 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00781
    Figure US20090189522A1-20090730-C00782
    Figure US20090189522A1-20090730-C00783
    Figure US20090189522A1-20090730-C00784
    D-175 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00785
    Figure US20090189522A1-20090730-C00786
    Figure US20090189522A1-20090730-C00787
    Figure US20090189522A1-20090730-C00788
    D-176 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00789
    Figure US20090189522A1-20090730-C00790
    Figure US20090189522A1-20090730-C00791
    Figure US20090189522A1-20090730-C00792
    D-177 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00793
    Figure US20090189522A1-20090730-C00794
    Figure US20090189522A1-20090730-C00795
    Figure US20090189522A1-20090730-C00796
    D-178 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00797
    Figure US20090189522A1-20090730-C00798
    Figure US20090189522A1-20090730-C00799
    Figure US20090189522A1-20090730-C00800
    D-179 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00801
    Figure US20090189522A1-20090730-C00802
    Figure US20090189522A1-20090730-C00803
    Figure US20090189522A1-20090730-C00804
    D-180 2-naphtyl H H H
    Figure US20090189522A1-20090730-C00805
    Figure US20090189522A1-20090730-C00806
    Figure US20090189522A1-20090730-C00807
    Figure US20090189522A1-20090730-C00808
  • TABLE 16
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00809
    Figure US20090189522A1-20090730-C00810
    Figure US20090189522A1-20090730-C00811
    Figure US20090189522A1-20090730-C00812
    D-181 Cyano H H H
    Figure US20090189522A1-20090730-C00813
    Figure US20090189522A1-20090730-C00814
    Figure US20090189522A1-20090730-C00815
    Figure US20090189522A1-20090730-C00816
    D-182 Cyano H H H
    Figure US20090189522A1-20090730-C00817
    Figure US20090189522A1-20090730-C00818
    Figure US20090189522A1-20090730-C00819
    Figure US20090189522A1-20090730-C00820
    D-183 Di- methyl- amino H H H
    Figure US20090189522A1-20090730-C00821
    Figure US20090189522A1-20090730-C00822
    Figure US20090189522A1-20090730-C00823
    Figure US20090189522A1-20090730-C00824
    D-184 Di- methyl- amino H H H
    Figure US20090189522A1-20090730-C00825
    Figure US20090189522A1-20090730-C00826
    Figure US20090189522A1-20090730-C00827
    Figure US20090189522A1-20090730-C00828
    D-185 Di- methyl- amino H H H
    Figure US20090189522A1-20090730-C00829
    Figure US20090189522A1-20090730-C00830
    Figure US20090189522A1-20090730-C00831
    Figure US20090189522A1-20090730-C00832
    D-186 2-methyl phenyl H H H
    Figure US20090189522A1-20090730-C00833
    Figure US20090189522A1-20090730-C00834
    Figure US20090189522A1-20090730-C00835
    Figure US20090189522A1-20090730-C00836
    D-187 2-methyl phenyl H H H
    Figure US20090189522A1-20090730-C00837
    Figure US20090189522A1-20090730-C00838
    Figure US20090189522A1-20090730-C00839
    Figure US20090189522A1-20090730-C00840
    D-188 2-methyl phenyl H H H
    Figure US20090189522A1-20090730-C00841
    Figure US20090189522A1-20090730-C00842
    Figure US20090189522A1-20090730-C00843
    Figure US20090189522A1-20090730-C00844
    D-189 2-biphenyl H H H
    Figure US20090189522A1-20090730-C00845
    Figure US20090189522A1-20090730-C00846
    Figure US20090189522A1-20090730-C00847
    Figure US20090189522A1-20090730-C00848
    D-190 2-biphenyl H H H
    Figure US20090189522A1-20090730-C00849
    Figure US20090189522A1-20090730-C00850
    Figure US20090189522A1-20090730-C00851
    Figure US20090189522A1-20090730-C00852
    D-191 2-biphenyl H H H
    Figure US20090189522A1-20090730-C00853
    Figure US20090189522A1-20090730-C00854
    Figure US20090189522A1-20090730-C00855
    Figure US20090189522A1-20090730-C00856
    D-192 2-biphenyl H H H
    Figure US20090189522A1-20090730-C00857
    Figure US20090189522A1-20090730-C00858
    Figure US20090189522A1-20090730-C00859
    Figure US20090189522A1-20090730-C00860
  • TABLE 17
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00861
    Figure US20090189522A1-20090730-C00862
    Figure US20090189522A1-20090730-C00863
    Figure US20090189522A1-20090730-C00864
    D-193 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00865
    Figure US20090189522A1-20090730-C00866
    Figure US20090189522A1-20090730-C00867
    Figure US20090189522A1-20090730-C00868
    D-194 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00869
    Figure US20090189522A1-20090730-C00870
    Figure US20090189522A1-20090730-C00871
    Figure US20090189522A1-20090730-C00872
    D-195 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00873
    Figure US20090189522A1-20090730-C00874
    Figure US20090189522A1-20090730-C00875
    Figure US20090189522A1-20090730-C00876
    D-196 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00877
    Figure US20090189522A1-20090730-C00878
    Figure US20090189522A1-20090730-C00879
    Figure US20090189522A1-20090730-C00880
    D-197 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00881
    Figure US20090189522A1-20090730-C00882
    Figure US20090189522A1-20090730-C00883
    Figure US20090189522A1-20090730-C00884
    D-198 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00885
    Figure US20090189522A1-20090730-C00886
    Figure US20090189522A1-20090730-C00887
    Figure US20090189522A1-20090730-C00888
    D-199 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00889
    Figure US20090189522A1-20090730-C00890
    Figure US20090189522A1-20090730-C00891
    Figure US20090189522A1-20090730-C00892
    D-200 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00893
    Figure US20090189522A1-20090730-C00894
    Figure US20090189522A1-20090730-C00895
    Figure US20090189522A1-20090730-C00896
    D-200 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00897
    Figure US20090189522A1-20090730-C00898
    Figure US20090189522A1-20090730-C00899
    Figure US20090189522A1-20090730-C00900
    D-201 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00901
    Figure US20090189522A1-20090730-C00902
    Figure US20090189522A1-20090730-C00903
    Figure US20090189522A1-20090730-C00904
    D-202 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00905
    Figure US20090189522A1-20090730-C00906
    Figure US20090189522A1-20090730-C00907
    Figure US20090189522A1-20090730-C00908
    D-203 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00909
    Figure US20090189522A1-20090730-C00910
    Figure US20090189522A1-20090730-C00911
    Figure US20090189522A1-20090730-C00912
    D-204 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00913
    Figure US20090189522A1-20090730-C00914
    Figure US20090189522A1-20090730-C00915
    Figure US20090189522A1-20090730-C00916
  • TABLE 18
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00917
    Figure US20090189522A1-20090730-C00918
    Figure US20090189522A1-20090730-C00919
    Figure US20090189522A1-20090730-C00920
    D-205 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00921
    Figure US20090189522A1-20090730-C00922
    Figure US20090189522A1-20090730-C00923
    Figure US20090189522A1-20090730-C00924
    D-206 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00925
    Figure US20090189522A1-20090730-C00926
    Figure US20090189522A1-20090730-C00927
    Figure US20090189522A1-20090730-C00928
    D-207 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00929
    Figure US20090189522A1-20090730-C00930
    Figure US20090189522A1-20090730-C00931
    Figure US20090189522A1-20090730-C00932
    D-208 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00933
    Figure US20090189522A1-20090730-C00934
    Figure US20090189522A1-20090730-C00935
    Figure US20090189522A1-20090730-C00936
    D-209 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00937
    Figure US20090189522A1-20090730-C00938
    Figure US20090189522A1-20090730-C00939
    Figure US20090189522A1-20090730-C00940
    D-210 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00941
    Figure US20090189522A1-20090730-C00942
    Figure US20090189522A1-20090730-C00943
    Figure US20090189522A1-20090730-C00944
    D-211 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00945
    Figure US20090189522A1-20090730-C00946
    Figure US20090189522A1-20090730-C00947
    Figure US20090189522A1-20090730-C00948
    D-212 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00949
    Figure US20090189522A1-20090730-C00950
    Figure US20090189522A1-20090730-C00951
    Figure US20090189522A1-20090730-C00952
    D-213 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00953
    Figure US20090189522A1-20090730-C00954
    Figure US20090189522A1-20090730-C00955
    Figure US20090189522A1-20090730-C00956
    D-214 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00957
    Figure US20090189522A1-20090730-C00958
    Figure US20090189522A1-20090730-C00959
    Figure US20090189522A1-20090730-C00960
    D-215 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00961
    Figure US20090189522A1-20090730-C00962
    Figure US20090189522A1-20090730-C00963
    Figure US20090189522A1-20090730-C00964
    D-216 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00965
    Figure US20090189522A1-20090730-C00966
    Figure US20090189522A1-20090730-C00967
    Figure US20090189522A1-20090730-C00968
  • TABLE 19
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C00969
    Figure US20090189522A1-20090730-C00970
    D-217 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00971
    Figure US20090189522A1-20090730-C00972
    D-218 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00973
    Figure US20090189522A1-20090730-C00974
    D-219 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00975
    Figure US20090189522A1-20090730-C00976
    D-220 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00977
    Figure US20090189522A1-20090730-C00978
    D-221 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00979
    Figure US20090189522A1-20090730-C00980
    D-222 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00981
    Figure US20090189522A1-20090730-C00982
    D-223 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00983
    Figure US20090189522A1-20090730-C00984
    D-224 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00985
    Figure US20090189522A1-20090730-C00986
    D-225 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00987
    Figure US20090189522A1-20090730-C00988
    D-226 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00989
    Figure US20090189522A1-20090730-C00990
    D-227 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00991
    Figure US20090189522A1-20090730-C00992
    D-228 Methyl Methyl H H
    Figure US20090189522A1-20090730-C00993
    Figure US20090189522A1-20090730-C00994
    Figure US20090189522A1-20090730-C00995
    Figure US20090189522A1-20090730-C00996
    D-217
    Figure US20090189522A1-20090730-C00997
    Figure US20090189522A1-20090730-C00998
    D-218
    Figure US20090189522A1-20090730-C00999
    Figure US20090189522A1-20090730-C01000
    D-219
    Figure US20090189522A1-20090730-C01001
    Figure US20090189522A1-20090730-C01002
    D-220
    Figure US20090189522A1-20090730-C01003
    Figure US20090189522A1-20090730-C01004
    D-221
    Figure US20090189522A1-20090730-C01005
    Figure US20090189522A1-20090730-C01006
    D-222
    Figure US20090189522A1-20090730-C01007
    Figure US20090189522A1-20090730-C01008
    D-223
    Figure US20090189522A1-20090730-C01009
    Figure US20090189522A1-20090730-C01010
    D-224
    Figure US20090189522A1-20090730-C01011
    Figure US20090189522A1-20090730-C01012
    D-225
    Figure US20090189522A1-20090730-C01013
    Figure US20090189522A1-20090730-C01014
    D-226
    Figure US20090189522A1-20090730-C01015
    Figure US20090189522A1-20090730-C01016
    D-227
    Figure US20090189522A1-20090730-C01017
    Figure US20090189522A1-20090730-C01018
    D-228
    Figure US20090189522A1-20090730-C01019
    Figure US20090189522A1-20090730-C01020
  • TABLE 20
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01021
    Figure US20090189522A1-20090730-C01022
    D-229 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01023
    Figure US20090189522A1-20090730-C01024
    D-230 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01025
    Figure US20090189522A1-20090730-C01026
    D-231 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01027
    Figure US20090189522A1-20090730-C01028
    D-232 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01029
    Figure US20090189522A1-20090730-C01030
    D-233 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01031
    Figure US20090189522A1-20090730-C01032
    D-234 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01033
    Figure US20090189522A1-20090730-C01034
    D-235 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01035
    Figure US20090189522A1-20090730-C01036
    D-236 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01037
    Figure US20090189522A1-20090730-C01038
    D-237 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01039
    Figure US20090189522A1-20090730-C01040
    D-238 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01041
    Figure US20090189522A1-20090730-C01042
    D-239 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01043
    Figure US20090189522A1-20090730-C01044
    D-240 Methyl Methyl H H
    Figure US20090189522A1-20090730-C01045
    Figure US20090189522A1-20090730-C01046
    Figure US20090189522A1-20090730-C01047
    Figure US20090189522A1-20090730-C01048
    D-229
    Figure US20090189522A1-20090730-C01049
    Figure US20090189522A1-20090730-C01050
    D-230
    Figure US20090189522A1-20090730-C01051
    Figure US20090189522A1-20090730-C01052
    D-231
    Figure US20090189522A1-20090730-C01053
    Figure US20090189522A1-20090730-C01054
    D-232
    Figure US20090189522A1-20090730-C01055
    Figure US20090189522A1-20090730-C01056
    D-233
    Figure US20090189522A1-20090730-C01057
    Figure US20090189522A1-20090730-C01058
    D-234
    Figure US20090189522A1-20090730-C01059
    Figure US20090189522A1-20090730-C01060
    D-235
    Figure US20090189522A1-20090730-C01061
    Figure US20090189522A1-20090730-C01062
    D-236
    Figure US20090189522A1-20090730-C01063
    Figure US20090189522A1-20090730-C01064
    D-237
    Figure US20090189522A1-20090730-C01065
    Figure US20090189522A1-20090730-C01066
    D-238
    Figure US20090189522A1-20090730-C01067
    Figure US20090189522A1-20090730-C01068
    D-239
    Figure US20090189522A1-20090730-C01069
    Figure US20090189522A1-20090730-C01070
    D-240
    Figure US20090189522A1-20090730-C01071
    Figure US20090189522A1-20090730-C01072
  • TABLE 21
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01073
    Figure US20090189522A1-20090730-C01074
    Figure US20090189522A1-20090730-C01075
    Figure US20090189522A1-20090730-C01076
    D-241 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01077
    Figure US20090189522A1-20090730-C01078
    Figure US20090189522A1-20090730-C01079
    Figure US20090189522A1-20090730-C01080
    D-242 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01081
    Figure US20090189522A1-20090730-C01082
    Figure US20090189522A1-20090730-C01083
    Figure US20090189522A1-20090730-C01084
    D-243 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01085
    Figure US20090189522A1-20090730-C01086
    Figure US20090189522A1-20090730-C01087
    Figure US20090189522A1-20090730-C01088
    D-244 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01089
    Figure US20090189522A1-20090730-C01090
    Figure US20090189522A1-20090730-C01091
    Figure US20090189522A1-20090730-C01092
    D-245 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01093
    Figure US20090189522A1-20090730-C01094
    Figure US20090189522A1-20090730-C01095
    Figure US20090189522A1-20090730-C01096
    D-246 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01097
    Figure US20090189522A1-20090730-C01098
    Figure US20090189522A1-20090730-C01099
    Figure US20090189522A1-20090730-C01100
    D-247 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01101
    Figure US20090189522A1-20090730-C01102
    Figure US20090189522A1-20090730-C01103
    Figure US20090189522A1-20090730-C01104
    D-248 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01105
    Figure US20090189522A1-20090730-C01106
    Figure US20090189522A1-20090730-C01107
    Figure US20090189522A1-20090730-C01108
    D-249 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01109
    Figure US20090189522A1-20090730-C01110
    Figure US20090189522A1-20090730-C01111
    Figure US20090189522A1-20090730-C01112
    D-250 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01113
    Figure US20090189522A1-20090730-C01114
    Figure US20090189522A1-20090730-C01115
    Figure US20090189522A1-20090730-C01116
    D-251 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01117
    Figure US20090189522A1-20090730-C01118
    Figure US20090189522A1-20090730-C01119
    Figure US20090189522A1-20090730-C01120
    D-252 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01121
    Figure US20090189522A1-20090730-C01122
    Figure US20090189522A1-20090730-C01123
    Figure US20090189522A1-20090730-C01124
  • TABLE 22
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01125
    Figure US20090189522A1-20090730-C01126
    D-253 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01127
    Figure US20090189522A1-20090730-C01128
    D-254 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01129
    Figure US20090189522A1-20090730-C01130
    D-255 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01131
    Figure US20090189522A1-20090730-C01132
    D-256 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01133
    Figure US20090189522A1-20090730-C01134
    D-257 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01135
    Figure US20090189522A1-20090730-C01136
    D-258 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01137
    Figure US20090189522A1-20090730-C01138
    D-259 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01139
    Figure US20090189522A1-20090730-C01140
    D-260 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01141
    Figure US20090189522A1-20090730-C01142
    D-261 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01143
    Figure US20090189522A1-20090730-C01144
    D-262 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01145
    Figure US20090189522A1-20090730-C01146
    D-263 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01147
    Figure US20090189522A1-20090730-C01148
    D-264 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01149
    Figure US20090189522A1-20090730-C01150
    Figure US20090189522A1-20090730-C01151
    Figure US20090189522A1-20090730-C01152
    D-253
    Figure US20090189522A1-20090730-C01153
    Figure US20090189522A1-20090730-C01154
    D-254
    Figure US20090189522A1-20090730-C01155
    Figure US20090189522A1-20090730-C01156
    D-255
    Figure US20090189522A1-20090730-C01157
    Figure US20090189522A1-20090730-C01158
    D-256
    Figure US20090189522A1-20090730-C01159
    Figure US20090189522A1-20090730-C01160
    D-257
    Figure US20090189522A1-20090730-C01161
    Figure US20090189522A1-20090730-C01162
    D-258
    Figure US20090189522A1-20090730-C01163
    Figure US20090189522A1-20090730-C01164
    D-259
    Figure US20090189522A1-20090730-C01165
    Figure US20090189522A1-20090730-C01166
    D-260
    Figure US20090189522A1-20090730-C01167
    Figure US20090189522A1-20090730-C01168
    D-261
    Figure US20090189522A1-20090730-C01169
    Figure US20090189522A1-20090730-C01170
    D-262
    Figure US20090189522A1-20090730-C01171
    Figure US20090189522A1-20090730-C01172
    D-263
    Figure US20090189522A1-20090730-C01173
    Figure US20090189522A1-20090730-C01174
    D-264
    Figure US20090189522A1-20090730-C01175
    Figure US20090189522A1-20090730-C01176
  • TABLE 23
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01177
    Figure US20090189522A1-20090730-C01178
    D-253 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01179
    Figure US20090189522A1-20090730-C01180
    D-254 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01181
    Figure US20090189522A1-20090730-C01182
    D-255 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01183
    Figure US20090189522A1-20090730-C01184
    D-256 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01185
    Figure US20090189522A1-20090730-C01186
    D-257 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01187
    Figure US20090189522A1-20090730-C01188
    D-258 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01189
    Figure US20090189522A1-20090730-C01190
    D-259 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01191
    Figure US20090189522A1-20090730-C01192
    D-260 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01193
    Figure US20090189522A1-20090730-C01194
    D-261 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01195
    Figure US20090189522A1-20090730-C01196
    D-262 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01197
    Figure US20090189522A1-20090730-C01198
    D-263 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01199
    Figure US20090189522A1-20090730-C01200
    D-264 Methyl Methyl Methyl Methyl
    Figure US20090189522A1-20090730-C01201
    Figure US20090189522A1-20090730-C01202
    Figure US20090189522A1-20090730-C01203
    Figure US20090189522A1-20090730-C01204
    D-253
    Figure US20090189522A1-20090730-C01205
    Figure US20090189522A1-20090730-C01206
    D-254
    Figure US20090189522A1-20090730-C01207
    Figure US20090189522A1-20090730-C01208
    D-255
    Figure US20090189522A1-20090730-C01209
    Figure US20090189522A1-20090730-C01210
    D-256
    Figure US20090189522A1-20090730-C01211
    Figure US20090189522A1-20090730-C01212
    D-257
    Figure US20090189522A1-20090730-C01213
    Figure US20090189522A1-20090730-C01214
    D-258
    Figure US20090189522A1-20090730-C01215
    Figure US20090189522A1-20090730-C01216
    D-259
    Figure US20090189522A1-20090730-C01217
    Figure US20090189522A1-20090730-C01218
    D-260
    Figure US20090189522A1-20090730-C01219
    Figure US20090189522A1-20090730-C01220
    D-261
    Figure US20090189522A1-20090730-C01221
    Figure US20090189522A1-20090730-C01222
    D-262
    Figure US20090189522A1-20090730-C01223
    Figure US20090189522A1-20090730-C01224
    D-263
    Figure US20090189522A1-20090730-C01225
    Figure US20090189522A1-20090730-C01226
    D-264
    Figure US20090189522A1-20090730-C01227
    Figure US20090189522A1-20090730-C01228
  • TABLE 24
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01229
    Figure US20090189522A1-20090730-C01230
    Figure US20090189522A1-20090730-C01231
    Figure US20090189522A1-20090730-C01232
    D-277 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01233
    Figure US20090189522A1-20090730-C01234
    Figure US20090189522A1-20090730-C01235
    Figure US20090189522A1-20090730-C01236
    D-278 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01237
    Figure US20090189522A1-20090730-C01238
    Figure US20090189522A1-20090730-C01239
    Figure US20090189522A1-20090730-C01240
    D-279 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01241
    Figure US20090189522A1-20090730-C01242
    Figure US20090189522A1-20090730-C01243
    Figure US20090189522A1-20090730-C01244
    D-280 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01245
    Figure US20090189522A1-20090730-C01246
    Figure US20090189522A1-20090730-C01247
    Figure US20090189522A1-20090730-C01248
    D-281 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01249
    Figure US20090189522A1-20090730-C01250
    Figure US20090189522A1-20090730-C01251
    Figure US20090189522A1-20090730-C01252
    D-282 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01253
    Figure US20090189522A1-20090730-C01254
    Figure US20090189522A1-20090730-C01255
    Figure US20090189522A1-20090730-C01256
    D-283 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01257
    Figure US20090189522A1-20090730-C01258
    Figure US20090189522A1-20090730-C01259
    Figure US20090189522A1-20090730-C01260
    D-284 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01261
    Figure US20090189522A1-20090730-C01262
    Figure US20090189522A1-20090730-C01263
    Figure US20090189522A1-20090730-C01264
    D-285 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01265
    Figure US20090189522A1-20090730-C01266
    Figure US20090189522A1-20090730-C01267
    Figure US20090189522A1-20090730-C01268
    D-286 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01269
    Figure US20090189522A1-20090730-C01270
    Figure US20090189522A1-20090730-C01271
    Figure US20090189522A1-20090730-C01272
    D-287 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01273
    Figure US20090189522A1-20090730-C01274
    Figure US20090189522A1-20090730-C01275
    Figure US20090189522A1-20090730-C01276
    D-288 Diphenyl Amino H H H
    Figure US20090189522A1-20090730-C01277
    Figure US20090189522A1-20090730-C01278
    Figure US20090189522A1-20090730-C01279
    Figure US20090189522A1-20090730-C01280
  • TABLE 25
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01281
    Figure US20090189522A1-20090730-C01282
    Figure US20090189522A1-20090730-C01283
    Figure US20090189522A1-20090730-C01284
    D-289 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01285
    Figure US20090189522A1-20090730-C01286
    Figure US20090189522A1-20090730-C01287
    Figure US20090189522A1-20090730-C01288
    D-290 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01289
    Figure US20090189522A1-20090730-C01290
    Figure US20090189522A1-20090730-C01291
    Figure US20090189522A1-20090730-C01292
    D-291 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01293
    Figure US20090189522A1-20090730-C01294
    Figure US20090189522A1-20090730-C01295
    Figure US20090189522A1-20090730-C01296
    D-292 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01297
    Figure US20090189522A1-20090730-C01298
    Figure US20090189522A1-20090730-C01299
    Figure US20090189522A1-20090730-C01300
    D-293 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01301
    Figure US20090189522A1-20090730-C01302
    Figure US20090189522A1-20090730-C01303
    Figure US20090189522A1-20090730-C01304
    D-294 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01305
    Figure US20090189522A1-20090730-C01306
    Figure US20090189522A1-20090730-C01307
    Figure US20090189522A1-20090730-C01308
    D-295 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01309
    Figure US20090189522A1-20090730-C01310
    Figure US20090189522A1-20090730-C01311
    Figure US20090189522A1-20090730-C01312
    D-296 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01313
    Figure US20090189522A1-20090730-C01314
    Figure US20090189522A1-20090730-C01315
    Figure US20090189522A1-20090730-C01316
    D-297 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01317
    Figure US20090189522A1-20090730-C01318
    Figure US20090189522A1-20090730-C01319
    Figure US20090189522A1-20090730-C01320
    D-298 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01321
    Figure US20090189522A1-20090730-C01322
    Figure US20090189522A1-20090730-C01323
    Figure US20090189522A1-20090730-C01324
    D-299 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01325
    Figure US20090189522A1-20090730-C01326
    Figure US20090189522A1-20090730-C01327
    Figure US20090189522A1-20090730-C01328
    D-300 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01329
    Figure US20090189522A1-20090730-C01330
    Figure US20090189522A1-20090730-C01331
    Figure US20090189522A1-20090730-C01332
  • TABLE 26
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01333
    Figure US20090189522A1-20090730-C01334
    Figure US20090189522A1-20090730-C01335
    Figure US20090189522A1-20090730-C01336
    D-301 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01337
    Figure US20090189522A1-20090730-C01338
    Figure US20090189522A1-20090730-C01339
    Figure US20090189522A1-20090730-C01340
    D-302 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01341
    Figure US20090189522A1-20090730-C01342
    Figure US20090189522A1-20090730-C01343
    Figure US20090189522A1-20090730-C01344
    D-303 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01345
    Figure US20090189522A1-20090730-C01346
    Figure US20090189522A1-20090730-C01347
    Figure US20090189522A1-20090730-C01348
    D-304 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01349
    Figure US20090189522A1-20090730-C01350
    Figure US20090189522A1-20090730-C01351
    Figure US20090189522A1-20090730-C01352
    D-305 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01353
    Figure US20090189522A1-20090730-C01354
    Figure US20090189522A1-20090730-C01355
    Figure US20090189522A1-20090730-C01356
    D-306 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01357
    Figure US20090189522A1-20090730-C01358
    Figure US20090189522A1-20090730-C01359
    Figure US20090189522A1-20090730-C01360
    D-307 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01361
    Figure US20090189522A1-20090730-C01362
    Figure US20090189522A1-20090730-C01363
    Figure US20090189522A1-20090730-C01364
    D-308 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01365
    Figure US20090189522A1-20090730-C01366
    Figure US20090189522A1-20090730-C01367
    Figure US20090189522A1-20090730-C01368
    D-309 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01369
    Figure US20090189522A1-20090730-C01370
    Figure US20090189522A1-20090730-C01371
    Figure US20090189522A1-20090730-C01372
    D-310 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01373
    Figure US20090189522A1-20090730-C01374
    Figure US20090189522A1-20090730-C01375
    Figure US20090189522A1-20090730-C01376
    D-311 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01377
    Figure US20090189522A1-20090730-C01378
    Figure US20090189522A1-20090730-C01379
    Figure US20090189522A1-20090730-C01380
    D-312 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01381
    Figure US20090189522A1-20090730-C01382
    Figure US20090189522A1-20090730-C01383
    Figure US20090189522A1-20090730-C01384
  • TABLE 27
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01385
    Figure US20090189522A1-20090730-C01386
    Figure US20090189522A1-20090730-C01387
    Figure US20090189522A1-20090730-C01388
    D-313 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01389
    Figure US20090189522A1-20090730-C01390
    Figure US20090189522A1-20090730-C01391
    Figure US20090189522A1-20090730-C01392
    D-314 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01393
    Figure US20090189522A1-20090730-C01394
    Figure US20090189522A1-20090730-C01395
    Figure US20090189522A1-20090730-C01396
    D-315 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01397
    Figure US20090189522A1-20090730-C01398
    Figure US20090189522A1-20090730-C01399
    Figure US20090189522A1-20090730-C01400
    D-316 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01401
    Figure US20090189522A1-20090730-C01402
    Figure US20090189522A1-20090730-C01403
    Figure US20090189522A1-20090730-C01404
    D-317 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01405
    Figure US20090189522A1-20090730-C01406
    Figure US20090189522A1-20090730-C01407
    Figure US20090189522A1-20090730-C01408
    D-318 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01409
    Figure US20090189522A1-20090730-C01410
    Figure US20090189522A1-20090730-C01411
    Figure US20090189522A1-20090730-C01412
    D-319 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01413
    Figure US20090189522A1-20090730-C01414
    Figure US20090189522A1-20090730-C01415
    Figure US20090189522A1-20090730-C01416
    D-320 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01417
    Figure US20090189522A1-20090730-C01418
    Figure US20090189522A1-20090730-C01419
    Figure US20090189522A1-20090730-C01420
    D-321 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01421
    Figure US20090189522A1-20090730-C01422
    Figure US20090189522A1-20090730-C01423
    Figure US20090189522A1-20090730-C01424
    D-322 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01425
    Figure US20090189522A1-20090730-C01426
    Figure US20090189522A1-20090730-C01427
    Figure US20090189522A1-20090730-C01428
    D-323 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01429
    Figure US20090189522A1-20090730-C01430
    Figure US20090189522A1-20090730-C01431
    Figure US20090189522A1-20090730-C01432
    D-324 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01433
    Figure US20090189522A1-20090730-C01434
    Figure US20090189522A1-20090730-C01435
    Figure US20090189522A1-20090730-C01436
  • TABLE 28
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01437
    Figure US20090189522A1-20090730-C01438
    Figure US20090189522A1-20090730-C01439
    Figure US20090189522A1-20090730-C01440
    D-325 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01441
    Figure US20090189522A1-20090730-C01442
    Figure US20090189522A1-20090730-C01443
    Figure US20090189522A1-20090730-C01444
    D-326 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01445
    Figure US20090189522A1-20090730-C01446
    Figure US20090189522A1-20090730-C01447
    Figure US20090189522A1-20090730-C01448
    D-327 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01449
    Figure US20090189522A1-20090730-C01450
    Figure US20090189522A1-20090730-C01451
    Figure US20090189522A1-20090730-C01452
    D-328 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01453
    Figure US20090189522A1-20090730-C01454
    Figure US20090189522A1-20090730-C01455
    Figure US20090189522A1-20090730-C01456
    D-329 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01457
    Figure US20090189522A1-20090730-C01458
    Figure US20090189522A1-20090730-C01459
    Figure US20090189522A1-20090730-C01460
    D-330 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01461
    Figure US20090189522A1-20090730-C01462
    Figure US20090189522A1-20090730-C01463
    Figure US20090189522A1-20090730-C01464
    D-331 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01465
    Figure US20090189522A1-20090730-C01466
    Figure US20090189522A1-20090730-C01467
    Figure US20090189522A1-20090730-C01468
    D-332 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01469
    Figure US20090189522A1-20090730-C01470
    Figure US20090189522A1-20090730-C01471
    Figure US20090189522A1-20090730-C01472
    D-333 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01473
    Figure US20090189522A1-20090730-C01474
    Figure US20090189522A1-20090730-C01475
    Figure US20090189522A1-20090730-C01476
    D-334 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01477
    Figure US20090189522A1-20090730-C01478
    Figure US20090189522A1-20090730-C01479
    Figure US20090189522A1-20090730-C01480
    D-335 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01481
    Figure US20090189522A1-20090730-C01482
    Figure US20090189522A1-20090730-C01483
    Figure US20090189522A1-20090730-C01484
    D-336 Methyl H Methyl H
    Figure US20090189522A1-20090730-C01485
    Figure US20090189522A1-20090730-C01486
    Figure US20090189522A1-20090730-C01487
    Figure US20090189522A1-20090730-C01488
  • TABLE 29
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01489
    Figure US20090189522A1-20090730-C01490
    Figure US20090189522A1-20090730-C01491
    Figure US20090189522A1-20090730-C01492
    D-337 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01493
    Figure US20090189522A1-20090730-C01494
    Figure US20090189522A1-20090730-C01495
    Figure US20090189522A1-20090730-C01496
    D-338 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01497
    Figure US20090189522A1-20090730-C01498
    Figure US20090189522A1-20090730-C01499
    Figure US20090189522A1-20090730-C01500
    D-339 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01501
    Figure US20090189522A1-20090730-C01502
    Figure US20090189522A1-20090730-C01503
    Figure US20090189522A1-20090730-C01504
    D-340 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01505
    Figure US20090189522A1-20090730-C01506
    Figure US20090189522A1-20090730-C01507
    Figure US20090189522A1-20090730-C01508
    D-341 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01509
    Figure US20090189522A1-20090730-C01510
    Figure US20090189522A1-20090730-C01511
    Figure US20090189522A1-20090730-C01512
    D-342 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01513
    Figure US20090189522A1-20090730-C01514
    Figure US20090189522A1-20090730-C01515
    Figure US20090189522A1-20090730-C01516
    D-343 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01517
    Figure US20090189522A1-20090730-C01518
    Figure US20090189522A1-20090730-C01519
    Figure US20090189522A1-20090730-C01520
    D-344 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01521
    Figure US20090189522A1-20090730-C01522
    Figure US20090189522A1-20090730-C01523
    Figure US20090189522A1-20090730-C01524
    D-345 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01525
    Figure US20090189522A1-20090730-C01526
    Figure US20090189522A1-20090730-C01527
    Figure US20090189522A1-20090730-C01528
    D-346 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01529
    Figure US20090189522A1-20090730-C01530
    Figure US20090189522A1-20090730-C01531
    Figure US20090189522A1-20090730-C01532
    D-347 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01533
    Figure US20090189522A1-20090730-C01534
    Figure US20090189522A1-20090730-C01535
    Figure US20090189522A1-20090730-C01536
    D-348 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01537
    Figure US20090189522A1-20090730-C01538
    Figure US20090189522A1-20090730-C01539
    Figure US20090189522A1-20090730-C01540
  • TABLE 30
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01541
    Figure US20090189522A1-20090730-C01542
    Figure US20090189522A1-20090730-C01543
    Figure US20090189522A1-20090730-C01544
    D-349 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01545
    Figure US20090189522A1-20090730-C01546
    Figure US20090189522A1-20090730-C01547
    Figure US20090189522A1-20090730-C01548
    D-350 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01549
    Figure US20090189522A1-20090730-C01550
    Figure US20090189522A1-20090730-C01551
    Figure US20090189522A1-20090730-C01552
    D-351 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01553
    Figure US20090189522A1-20090730-C01554
    Figure US20090189522A1-20090730-C01555
    Figure US20090189522A1-20090730-C01556
    D-352 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01557
    Figure US20090189522A1-20090730-C01558
    Figure US20090189522A1-20090730-C01559
    Figure US20090189522A1-20090730-C01560
    D-353 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01561
    Figure US20090189522A1-20090730-C01562
    Figure US20090189522A1-20090730-C01563
    Figure US20090189522A1-20090730-C01564
    D-354 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01565
    Figure US20090189522A1-20090730-C01566
    Figure US20090189522A1-20090730-C01567
    Figure US20090189522A1-20090730-C01568
    D-355 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01569
    Figure US20090189522A1-20090730-C01570
    Figure US20090189522A1-20090730-C01571
    Figure US20090189522A1-20090730-C01572
    D-356 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01573
    Figure US20090189522A1-20090730-C01574
    Figure US20090189522A1-20090730-C01575
    Figure US20090189522A1-20090730-C01576
    D-357 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01577
    Figure US20090189522A1-20090730-C01578
    Figure US20090189522A1-20090730-C01579
    Figure US20090189522A1-20090730-C01580
    D-358 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01581
    Figure US20090189522A1-20090730-C01582
    Figure US20090189522A1-20090730-C01583
    Figure US20090189522A1-20090730-C01584
    D-359 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01585
    Figure US20090189522A1-20090730-C01586
    Figure US20090189522A1-20090730-C01587
    Figure US20090189522A1-20090730-C01588
    D-360 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01589
    Figure US20090189522A1-20090730-C01590
    Figure US20090189522A1-20090730-C01591
    Figure US20090189522A1-20090730-C01592
  • TABLE 31
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01593
    Figure US20090189522A1-20090730-C01594
    Figure US20090189522A1-20090730-C01595
    Figure US20090189522A1-20090730-C01596
    D-361 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01597
    Figure US20090189522A1-20090730-C01598
    Figure US20090189522A1-20090730-C01599
    Figure US20090189522A1-20090730-C01600
    D-362 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01601
    Figure US20090189522A1-20090730-C01602
    Figure US20090189522A1-20090730-C01603
    Figure US20090189522A1-20090730-C01604
    D-363 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01605
    Figure US20090189522A1-20090730-C01606
    Figure US20090189522A1-20090730-C01607
    Figure US20090189522A1-20090730-C01608
    D-364 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01609
    Figure US20090189522A1-20090730-C01610
    Figure US20090189522A1-20090730-C01611
    Figure US20090189522A1-20090730-C01612
    D-365 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01613
    Figure US20090189522A1-20090730-C01614
    Figure US20090189522A1-20090730-C01615
    Figure US20090189522A1-20090730-C01616
    D-366 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01617
    Figure US20090189522A1-20090730-C01618
    Figure US20090189522A1-20090730-C01619
    Figure US20090189522A1-20090730-C01620
    D-367 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01621
    Figure US20090189522A1-20090730-C01622
    Figure US20090189522A1-20090730-C01623
    Figure US20090189522A1-20090730-C01624
    D-368 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01625
    Figure US20090189522A1-20090730-C01626
    Figure US20090189522A1-20090730-C01627
    Figure US20090189522A1-20090730-C01628
    D-369 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01629
    Figure US20090189522A1-20090730-C01630
    Figure US20090189522A1-20090730-C01631
    Figure US20090189522A1-20090730-C01632
    D-370 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01633
    Figure US20090189522A1-20090730-C01634
    Figure US20090189522A1-20090730-C01635
    Figure US20090189522A1-20090730-C01636
    D-371 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01637
    Figure US20090189522A1-20090730-C01638
    Figure US20090189522A1-20090730-C01639
    Figure US20090189522A1-20090730-C01640
    D-372 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01641
    Figure US20090189522A1-20090730-C01642
    Figure US20090189522A1-20090730-C01643
    Figure US20090189522A1-20090730-C01644
  • TABLE 32
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01645
    Figure US20090189522A1-20090730-C01646
    Figure US20090189522A1-20090730-C01647
    Figure US20090189522A1-20090730-C01648
    D-373 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01649
    Figure US20090189522A1-20090730-C01650
    Figure US20090189522A1-20090730-C01651
    Figure US20090189522A1-20090730-C01652
    D-374 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01653
    Figure US20090189522A1-20090730-C01654
    Figure US20090189522A1-20090730-C01655
    Figure US20090189522A1-20090730-C01656
    D-375 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01657
    Figure US20090189522A1-20090730-C01658
    Figure US20090189522A1-20090730-C01659
    Figure US20090189522A1-20090730-C01660
    D-376 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01661
    Figure US20090189522A1-20090730-C01662
    Figure US20090189522A1-20090730-C01663
    Figure US20090189522A1-20090730-C01664
    D-377 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01665
    Figure US20090189522A1-20090730-C01666
    Figure US20090189522A1-20090730-C01667
    Figure US20090189522A1-20090730-C01668
    D-378 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01669
    Figure US20090189522A1-20090730-C01670
    Figure US20090189522A1-20090730-C01671
    Figure US20090189522A1-20090730-C01672
    D-379 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01673
    Figure US20090189522A1-20090730-C01674
    Figure US20090189522A1-20090730-C01675
    Figure US20090189522A1-20090730-C01676
    D-380 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01677
    Figure US20090189522A1-20090730-C01678
    Figure US20090189522A1-20090730-C01679
    Figure US20090189522A1-20090730-C01680
    D-381 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01681
    Figure US20090189522A1-20090730-C01682
    Figure US20090189522A1-20090730-C01683
    Figure US20090189522A1-20090730-C01684
    D-382 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01685
    Figure US20090189522A1-20090730-C01686
    Figure US20090189522A1-20090730-C01687
    Figure US20090189522A1-20090730-C01688
    D-383 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01689
    Figure US20090189522A1-20090730-C01690
    Figure US20090189522A1-20090730-C01691
    Figure US20090189522A1-20090730-C01692
    D-384 Isopropyl H Isopropyl H
    Figure US20090189522A1-20090730-C01693
    Figure US20090189522A1-20090730-C01694
    Figure US20090189522A1-20090730-C01695
    Figure US20090189522A1-20090730-C01696
  • TABLE 33
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01697
    Figure US20090189522A1-20090730-C01698
    Figure US20090189522A1-20090730-C01699
    Figure US20090189522A1-20090730-C01700
    D-385 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01701
    Figure US20090189522A1-20090730-C01702
    Figure US20090189522A1-20090730-C01703
    Figure US20090189522A1-20090730-C01704
    D-386 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01705
    Figure US20090189522A1-20090730-C01706
    Figure US20090189522A1-20090730-C01707
    Figure US20090189522A1-20090730-C01708
    D-387 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01709
    Figure US20090189522A1-20090730-C01710
    Figure US20090189522A1-20090730-C01711
    Figure US20090189522A1-20090730-C01712
    D-388 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01713
    Figure US20090189522A1-20090730-C01714
    Figure US20090189522A1-20090730-C01715
    Figure US20090189522A1-20090730-C01716
    D-389 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01717
    Figure US20090189522A1-20090730-C01718
    Figure US20090189522A1-20090730-C01719
    Figure US20090189522A1-20090730-C01720
    D-390 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01721
    Figure US20090189522A1-20090730-C01722
    Figure US20090189522A1-20090730-C01723
    Figure US20090189522A1-20090730-C01724
    D-391 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01725
    Figure US20090189522A1-20090730-C01726
    Figure US20090189522A1-20090730-C01727
    Figure US20090189522A1-20090730-C01728
    D-392 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01729
    Figure US20090189522A1-20090730-C01730
    Figure US20090189522A1-20090730-C01731
    Figure US20090189522A1-20090730-C01732
    D-393 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01733
    Figure US20090189522A1-20090730-C01734
    Figure US20090189522A1-20090730-C01735
    Figure US20090189522A1-20090730-C01736
    D-394 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01737
    Figure US20090189522A1-20090730-C01738
    Figure US20090189522A1-20090730-C01739
    Figure US20090189522A1-20090730-C01740
    D-395 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01741
    Figure US20090189522A1-20090730-C01742
    Figure US20090189522A1-20090730-C01743
    Figure US20090189522A1-20090730-C01744
    D-396 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01745
    Figure US20090189522A1-20090730-C01746
    Figure US20090189522A1-20090730-C01747
    Figure US20090189522A1-20090730-C01748
  • TABLE 34
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01749
    Figure US20090189522A1-20090730-C01750
    Figure US20090189522A1-20090730-C01751
    Figure US20090189522A1-20090730-C01752
    D-397 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01753
    Figure US20090189522A1-20090730-C01754
    Figure US20090189522A1-20090730-C01755
    Figure US20090189522A1-20090730-C01756
    D-398 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01757
    Figure US20090189522A1-20090730-C01758
    Figure US20090189522A1-20090730-C01759
    Figure US20090189522A1-20090730-C01760
    D-399 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01761
    Figure US20090189522A1-20090730-C01762
    Figure US20090189522A1-20090730-C01763
    Figure US20090189522A1-20090730-C01764
    D-400 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01765
    Figure US20090189522A1-20090730-C01766
    Figure US20090189522A1-20090730-C01767
    Figure US20090189522A1-20090730-C01768
    D-401 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01769
    Figure US20090189522A1-20090730-C01770
    Figure US20090189522A1-20090730-C01771
    Figure US20090189522A1-20090730-C01772
    D-402 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01773
    Figure US20090189522A1-20090730-C01774
    Figure US20090189522A1-20090730-C01775
    Figure US20090189522A1-20090730-C01776
    D-403 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01777
    Figure US20090189522A1-20090730-C01778
    Figure US20090189522A1-20090730-C01779
    Figure US20090189522A1-20090730-C01780
    D-404 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01781
    Figure US20090189522A1-20090730-C01782
    Figure US20090189522A1-20090730-C01783
    Figure US20090189522A1-20090730-C01784
    D-404 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01785
    Figure US20090189522A1-20090730-C01786
    Figure US20090189522A1-20090730-C01787
    Figure US20090189522A1-20090730-C01788
    D-405 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01789
    Figure US20090189522A1-20090730-C01790
    Figure US20090189522A1-20090730-C01791
    Figure US20090189522A1-20090730-C01792
    D-406 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01793
    Figure US20090189522A1-20090730-C01794
    Figure US20090189522A1-20090730-C01795
    Figure US20090189522A1-20090730-C01796
    D-407 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01797
    Figure US20090189522A1-20090730-C01798
    Figure US20090189522A1-20090730-C01799
    Figure US20090189522A1-20090730-C01800
    D-408 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01801
    Figure US20090189522A1-20090730-C01802
    Figure US20090189522A1-20090730-C01803
    Figure US20090189522A1-20090730-C01804
  • TABLE 35
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01805
    Figure US20090189522A1-20090730-C01806
    Figure US20090189522A1-20090730-C01807
    Figure US20090189522A1-20090730-C01808
    D-409 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01809
    Figure US20090189522A1-20090730-C01810
    Figure US20090189522A1-20090730-C01811
    Figure US20090189522A1-20090730-C01812
    D-410 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01813
    Figure US20090189522A1-20090730-C01814
    Figure US20090189522A1-20090730-C01815
    Figure US20090189522A1-20090730-C01816
    D-411 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01817
    Figure US20090189522A1-20090730-C01818
    Figure US20090189522A1-20090730-C01819
    Figure US20090189522A1-20090730-C01820
    D-412 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01821
    Figure US20090189522A1-20090730-C01822
    Figure US20090189522A1-20090730-C01823
    Figure US20090189522A1-20090730-C01824
    D-413 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01825
    Figure US20090189522A1-20090730-C01826
    Figure US20090189522A1-20090730-C01827
    Figure US20090189522A1-20090730-C01828
    D-414 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01829
    Figure US20090189522A1-20090730-C01830
    Figure US20090189522A1-20090730-C01831
    Figure US20090189522A1-20090730-C01832
    D-415 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01833
    Figure US20090189522A1-20090730-C01834
    Figure US20090189522A1-20090730-C01835
    Figure US20090189522A1-20090730-C01836
    D-416 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01837
    Figure US20090189522A1-20090730-C01838
    Figure US20090189522A1-20090730-C01839
    Figure US20090189522A1-20090730-C01840
    D-417 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01841
    Figure US20090189522A1-20090730-C01842
    Figure US20090189522A1-20090730-C01843
    Figure US20090189522A1-20090730-C01844
    D-418 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01845
    Figure US20090189522A1-20090730-C01846
    Figure US20090189522A1-20090730-C01847
    Figure US20090189522A1-20090730-C01848
    D-419 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01849
    Figure US20090189522A1-20090730-C01850
    Figure US20090189522A1-20090730-C01851
    Figure US20090189522A1-20090730-C01852
    D-420 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01853
    Figure US20090189522A1-20090730-C01854
    Figure US20090189522A1-20090730-C01855
    Figure US20090189522A1-20090730-C01856
  • TABLE 36
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01857
    Figure US20090189522A1-20090730-C01858
    Figure US20090189522A1-20090730-C01859
    Figure US20090189522A1-20090730-C01860
    D-421 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01861
    Figure US20090189522A1-20090730-C01862
    Figure US20090189522A1-20090730-C01863
    Figure US20090189522A1-20090730-C01864
    D-422 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01865
    Figure US20090189522A1-20090730-C01866
    Figure US20090189522A1-20090730-C01867
    Figure US20090189522A1-20090730-C01868
    D-423 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01869
    Figure US20090189522A1-20090730-C01870
    Figure US20090189522A1-20090730-C01871
    Figure US20090189522A1-20090730-C01872
    D-424 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01873
    Figure US20090189522A1-20090730-C01874
    Figure US20090189522A1-20090730-C01875
    Figure US20090189522A1-20090730-C01876
    D-425 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01877
    Figure US20090189522A1-20090730-C01878
    Figure US20090189522A1-20090730-C01879
    Figure US20090189522A1-20090730-C01880
    D-426 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01881
    Figure US20090189522A1-20090730-C01882
    Figure US20090189522A1-20090730-C01883
    Figure US20090189522A1-20090730-C01884
    D-427 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01885
    Figure US20090189522A1-20090730-C01886
    Figure US20090189522A1-20090730-C01887
    Figure US20090189522A1-20090730-C01888
    D-428 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01889
    Figure US20090189522A1-20090730-C01890
    Figure US20090189522A1-20090730-C01891
    Figure US20090189522A1-20090730-C01892
    D-429 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01893
    Figure US20090189522A1-20090730-C01894
    Figure US20090189522A1-20090730-C01895
    Figure US20090189522A1-20090730-C01896
    D-430 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01897
    Figure US20090189522A1-20090730-C01898
    Figure US20090189522A1-20090730-C01899
    Figure US20090189522A1-20090730-C01900
    D-431 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01901
    Figure US20090189522A1-20090730-C01902
    Figure US20090189522A1-20090730-C01903
    Figure US20090189522A1-20090730-C01904
    D-432 t-Butyl H t-Butyl H
    Figure US20090189522A1-20090730-C01905
    Figure US20090189522A1-20090730-C01906
    Figure US20090189522A1-20090730-C01907
    Figure US20090189522A1-20090730-C01908
  • TABLE 37
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01909
    Figure US20090189522A1-20090730-C01910
    Figure US20090189522A1-20090730-C01911
    Figure US20090189522A1-20090730-C01912
    D-433 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01913
    Figure US20090189522A1-20090730-C01914
    Figure US20090189522A1-20090730-C01915
    Figure US20090189522A1-20090730-C01916
    D-434 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01917
    Figure US20090189522A1-20090730-C01918
    Figure US20090189522A1-20090730-C01919
    Figure US20090189522A1-20090730-C01920
    D-435 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01921
    Figure US20090189522A1-20090730-C01922
    Figure US20090189522A1-20090730-C01923
    Figure US20090189522A1-20090730-C01924
    D-436 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01925
    Figure US20090189522A1-20090730-C01926
    Figure US20090189522A1-20090730-C01927
    Figure US20090189522A1-20090730-C01928
    D-437 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01929
    Figure US20090189522A1-20090730-C01930
    Figure US20090189522A1-20090730-C01931
    Figure US20090189522A1-20090730-C01932
    D-438 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01933
    Figure US20090189522A1-20090730-C01934
    Figure US20090189522A1-20090730-C01935
    Figure US20090189522A1-20090730-C01936
    D-439 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01937
    Figure US20090189522A1-20090730-C01938
    Figure US20090189522A1-20090730-C01939
    Figure US20090189522A1-20090730-C01940
    D-440 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01941
    Figure US20090189522A1-20090730-C01942
    Figure US20090189522A1-20090730-C01943
    Figure US20090189522A1-20090730-C01944
    D-441 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01945
    Figure US20090189522A1-20090730-C01946
    Figure US20090189522A1-20090730-C01947
    Figure US20090189522A1-20090730-C01948
    D-442 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01949
    Figure US20090189522A1-20090730-C01950
    Figure US20090189522A1-20090730-C01951
    Figure US20090189522A1-20090730-C01952
    D-443 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01953
    Figure US20090189522A1-20090730-C01954
    Figure US20090189522A1-20090730-C01955
    Figure US20090189522A1-20090730-C01956
    D-444 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01957
    Figure US20090189522A1-20090730-C01958
    Figure US20090189522A1-20090730-C01959
    Figure US20090189522A1-20090730-C01960
  • TABLE 38
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C01961
    Figure US20090189522A1-20090730-C01962
    Figure US20090189522A1-20090730-C01963
    Figure US20090189522A1-20090730-C01964
    D-445 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01965
    Figure US20090189522A1-20090730-C01966
    Figure US20090189522A1-20090730-C01967
    Figure US20090189522A1-20090730-C01968
    D-446 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01969
    Figure US20090189522A1-20090730-C01970
    Figure US20090189522A1-20090730-C01971
    Figure US20090189522A1-20090730-C01972
    D-447 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01973
    Figure US20090189522A1-20090730-C01974
    Figure US20090189522A1-20090730-C01975
    Figure US20090189522A1-20090730-C01976
    D-448 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01977
    Figure US20090189522A1-20090730-C01978
    Figure US20090189522A1-20090730-C01979
    Figure US20090189522A1-20090730-C01980
    D-449 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01981
    Figure US20090189522A1-20090730-C01982
    Figure US20090189522A1-20090730-C01983
    Figure US20090189522A1-20090730-C01984
    D-450 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01985
    Figure US20090189522A1-20090730-C01986
    Figure US20090189522A1-20090730-C01987
    Figure US20090189522A1-20090730-C01988
    D-451 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01989
    Figure US20090189522A1-20090730-C01990
    Figure US20090189522A1-20090730-C01991
    Figure US20090189522A1-20090730-C01992
    D-452 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01993
    Figure US20090189522A1-20090730-C01994
    Figure US20090189522A1-20090730-C01995
    Figure US20090189522A1-20090730-C01996
    D-453 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C01997
    Figure US20090189522A1-20090730-C01998
    Figure US20090189522A1-20090730-C01999
    Figure US20090189522A1-20090730-C02000
    D-454 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02001
    Figure US20090189522A1-20090730-C02002
    Figure US20090189522A1-20090730-C02003
    Figure US20090189522A1-20090730-C02004
    D-455 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02005
    Figure US20090189522A1-20090730-C02006
    Figure US20090189522A1-20090730-C02007
    Figure US20090189522A1-20090730-C02008
    D-456 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02009
    Figure US20090189522A1-20090730-C02010
    Figure US20090189522A1-20090730-C02011
    Figure US20090189522A1-20090730-C02012
  • TABLE 39
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02013
    Figure US20090189522A1-20090730-C02014
    D-457 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02015
    Figure US20090189522A1-20090730-C02016
    D-458 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02017
    Figure US20090189522A1-20090730-C02018
    D-459 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02019
    Figure US20090189522A1-20090730-C02020
    D-460 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02021
    Figure US20090189522A1-20090730-C02022
    D-461 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02023
    Figure US20090189522A1-20090730-C02024
    D-462 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02025
    Figure US20090189522A1-20090730-C02026
    D-463 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02027
    Figure US20090189522A1-20090730-C02028
    D-464 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02029
    Figure US20090189522A1-20090730-C02030
    D-465 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02031
    Figure US20090189522A1-20090730-C02032
    D-466 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02033
    Figure US20090189522A1-20090730-C02034
    D-467 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02035
    Figure US20090189522A1-20090730-C02036
    D-468 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02037
    Figure US20090189522A1-20090730-C02038
    Figure US20090189522A1-20090730-C02039
    Figure US20090189522A1-20090730-C02040
    D-457
    Figure US20090189522A1-20090730-C02041
    Figure US20090189522A1-20090730-C02042
    D-458
    Figure US20090189522A1-20090730-C02043
    Figure US20090189522A1-20090730-C02044
    D-459
    Figure US20090189522A1-20090730-C02045
    Figure US20090189522A1-20090730-C02046
    D-460
    Figure US20090189522A1-20090730-C02047
    Figure US20090189522A1-20090730-C02048
    D-461
    Figure US20090189522A1-20090730-C02049
    Figure US20090189522A1-20090730-C02050
    D-462
    Figure US20090189522A1-20090730-C02051
    Figure US20090189522A1-20090730-C02052
    D-463
    Figure US20090189522A1-20090730-C02053
    Figure US20090189522A1-20090730-C02054
    D-464
    Figure US20090189522A1-20090730-C02055
    Figure US20090189522A1-20090730-C02056
    D-465
    Figure US20090189522A1-20090730-C02057
    Figure US20090189522A1-20090730-C02058
    D-466
    Figure US20090189522A1-20090730-C02059
    Figure US20090189522A1-20090730-C02060
    D-467
    Figure US20090189522A1-20090730-C02061
    Figure US20090189522A1-20090730-C02062
    D-468
    Figure US20090189522A1-20090730-C02063
    Figure US20090189522A1-20090730-C02064
  • TABLE 40
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02065
    Figure US20090189522A1-20090730-C02066
    D-469 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02067
    Figure US20090189522A1-20090730-C02068
    D-470 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02069
    Figure US20090189522A1-20090730-C02070
    D-471 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02071
    Figure US20090189522A1-20090730-C02072
    D-472 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02073
    Figure US20090189522A1-20090730-C02074
    D-473 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02075
    Figure US20090189522A1-20090730-C02076
    D-474 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02077
    Figure US20090189522A1-20090730-C02078
    D-475 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02079
    Figure US20090189522A1-20090730-C02080
    D-476 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02081
    Figure US20090189522A1-20090730-C02082
    D-477 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02083
    Figure US20090189522A1-20090730-C02084
    D-478 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02085
    Figure US20090189522A1-20090730-C02086
    D-479 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02087
    Figure US20090189522A1-20090730-C02088
    D-480 Phenyl H Phenyl H
    Figure US20090189522A1-20090730-C02089
    Figure US20090189522A1-20090730-C02090
    Figure US20090189522A1-20090730-C02091
    Figure US20090189522A1-20090730-C02092
    D-469
    Figure US20090189522A1-20090730-C02093
    Figure US20090189522A1-20090730-C02094
    D-470
    Figure US20090189522A1-20090730-C02095
    Figure US20090189522A1-20090730-C02096
    D-471
    Figure US20090189522A1-20090730-C02097
    Figure US20090189522A1-20090730-C02098
    D-472
    Figure US20090189522A1-20090730-C02099
    Figure US20090189522A1-20090730-C02100
    D-473
    Figure US20090189522A1-20090730-C02101
    Figure US20090189522A1-20090730-C02102
    D-474
    Figure US20090189522A1-20090730-C02103
    Figure US20090189522A1-20090730-C02104
    D-475
    Figure US20090189522A1-20090730-C02105
    Figure US20090189522A1-20090730-C02106
    D-476
    Figure US20090189522A1-20090730-C02107
    Figure US20090189522A1-20090730-C02108
    D-477
    Figure US20090189522A1-20090730-C02109
    Figure US20090189522A1-20090730-C02110
    D-478
    Figure US20090189522A1-20090730-C02111
    Figure US20090189522A1-20090730-C02112
    D-479
    Figure US20090189522A1-20090730-C02113
    Figure US20090189522A1-20090730-C02114
    D-480
    Figure US20090189522A1-20090730-C02115
    Figure US20090189522A1-20090730-C02116
  • TABLE 41
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C02117
    Figure US20090189522A1-20090730-C02118
    Figure US20090189522A1-20090730-C02119
    Figure US20090189522A1-20090730-C02120
    D-481 H Methyl H H
    Figure US20090189522A1-20090730-C02121
    Figure US20090189522A1-20090730-C02122
    Figure US20090189522A1-20090730-C02123
    Figure US20090189522A1-20090730-C02124
    D-482 H Methyl H H
    Figure US20090189522A1-20090730-C02125
    Figure US20090189522A1-20090730-C02126
    Figure US20090189522A1-20090730-C02127
    Figure US20090189522A1-20090730-C02128
    D-483 H Methyl H H
    Figure US20090189522A1-20090730-C02129
    Figure US20090189522A1-20090730-C02130
    Figure US20090189522A1-20090730-C02131
    Figure US20090189522A1-20090730-C02132
    D-484 H Methyl H H
    Figure US20090189522A1-20090730-C02133
    Figure US20090189522A1-20090730-C02134
    Figure US20090189522A1-20090730-C02135
    Figure US20090189522A1-20090730-C02136
    D-485 H Methyl H H
    Figure US20090189522A1-20090730-C02137
    Figure US20090189522A1-20090730-C02138
    Figure US20090189522A1-20090730-C02139
    Figure US20090189522A1-20090730-C02140
    D-486 H Methyl H H
    Figure US20090189522A1-20090730-C02141
    Figure US20090189522A1-20090730-C02142
    Figure US20090189522A1-20090730-C02143
    Figure US20090189522A1-20090730-C02144
    D-487 H Methyl H H
    Figure US20090189522A1-20090730-C02145
    Figure US20090189522A1-20090730-C02146
    Figure US20090189522A1-20090730-C02147
    Figure US20090189522A1-20090730-C02148
    D-488 H Methyl H H
    Figure US20090189522A1-20090730-C02149
    Figure US20090189522A1-20090730-C02150
    Figure US20090189522A1-20090730-C02151
    Figure US20090189522A1-20090730-C02152
    D-489 H Methyl H H
    Figure US20090189522A1-20090730-C02153
    Figure US20090189522A1-20090730-C02154
    Figure US20090189522A1-20090730-C02155
    Figure US20090189522A1-20090730-C02156
    D-490 H Methyl H H
    Figure US20090189522A1-20090730-C02157
    Figure US20090189522A1-20090730-C02158
    Figure US20090189522A1-20090730-C02159
    Figure US20090189522A1-20090730-C02160
    D-491 H Methyl H H
    Figure US20090189522A1-20090730-C02161
    Figure US20090189522A1-20090730-C02162
    Figure US20090189522A1-20090730-C02163
    Figure US20090189522A1-20090730-C02164
    D-492 H Methyl H H
    Figure US20090189522A1-20090730-C02165
    Figure US20090189522A1-20090730-C02166
    Figure US20090189522A1-20090730-C02167
    Figure US20090189522A1-20090730-C02168
  • TABLE 42
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02169
    Figure US20090189522A1-20090730-C02170
    D-493 H Methyl H H
    Figure US20090189522A1-20090730-C02171
    Figure US20090189522A1-20090730-C02172
    D-494 H Methyl H H
    Figure US20090189522A1-20090730-C02173
    Figure US20090189522A1-20090730-C02174
    D-495 H Methyl H H
    Figure US20090189522A1-20090730-C02175
    Figure US20090189522A1-20090730-C02176
    D-496 H Methyl H H
    Figure US20090189522A1-20090730-C02177
    Figure US20090189522A1-20090730-C02178
    D-497 H Methyl H H
    Figure US20090189522A1-20090730-C02179
    Figure US20090189522A1-20090730-C02180
    D-498 H Methyl H H
    Figure US20090189522A1-20090730-C02181
    Figure US20090189522A1-20090730-C02182
    D-499 H Methyl H H
    Figure US20090189522A1-20090730-C02183
    Figure US20090189522A1-20090730-C02184
    D-500 H Methyl H H
    Figure US20090189522A1-20090730-C02185
    Figure US20090189522A1-20090730-C02186
    D-501 H Methyl H H
    Figure US20090189522A1-20090730-C02187
    Figure US20090189522A1-20090730-C02188
    D-502 H Methyl H H
    Figure US20090189522A1-20090730-C02189
    Figure US20090189522A1-20090730-C02190
    D-503 H Methyl H H
    Figure US20090189522A1-20090730-C02191
    Figure US20090189522A1-20090730-C02192
    D-504 H Methyl H H
    Figure US20090189522A1-20090730-C02193
    Figure US20090189522A1-20090730-C02194
    Figure US20090189522A1-20090730-C02195
    Figure US20090189522A1-20090730-C02196
    D-493
    Figure US20090189522A1-20090730-C02197
    Figure US20090189522A1-20090730-C02198
    D-494
    Figure US20090189522A1-20090730-C02199
    Figure US20090189522A1-20090730-C02200
    D-495
    Figure US20090189522A1-20090730-C02201
    Figure US20090189522A1-20090730-C02202
    D-496
    Figure US20090189522A1-20090730-C02203
    Figure US20090189522A1-20090730-C02204
    D-497
    Figure US20090189522A1-20090730-C02205
    Figure US20090189522A1-20090730-C02206
    D-498
    Figure US20090189522A1-20090730-C02207
    Figure US20090189522A1-20090730-C02208
    D-499
    Figure US20090189522A1-20090730-C02209
    Figure US20090189522A1-20090730-C02210
    D-500
    Figure US20090189522A1-20090730-C02211
    Figure US20090189522A1-20090730-C02212
    D-501
    Figure US20090189522A1-20090730-C02213
    Figure US20090189522A1-20090730-C02214
    D-502
    Figure US20090189522A1-20090730-C02215
    Figure US20090189522A1-20090730-C02216
    D-503
    Figure US20090189522A1-20090730-C02217
    Figure US20090189522A1-20090730-C02218
    D-504
    Figure US20090189522A1-20090730-C02219
    Figure US20090189522A1-20090730-C02220
  • TABLE 43
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02221
    Figure US20090189522A1-20090730-C02222
    D-505 H Methyl H H
    Figure US20090189522A1-20090730-C02223
    Figure US20090189522A1-20090730-C02224
    D-506 H Methyl H H
    Figure US20090189522A1-20090730-C02225
    Figure US20090189522A1-20090730-C02226
    D-507 H Methyl H H
    Figure US20090189522A1-20090730-C02227
    Figure US20090189522A1-20090730-C02228
    D-508 H Methyl H H
    Figure US20090189522A1-20090730-C02229
    Figure US20090189522A1-20090730-C02230
    D-509 H Methyl H H
    Figure US20090189522A1-20090730-C02231
    Figure US20090189522A1-20090730-C02232
    D-510 H Methyl H H
    Figure US20090189522A1-20090730-C02233
    Figure US20090189522A1-20090730-C02234
    D-511 H Methyl H H
    Figure US20090189522A1-20090730-C02235
    Figure US20090189522A1-20090730-C02236
    D-512 H Methyl H H
    Figure US20090189522A1-20090730-C02237
    Figure US20090189522A1-20090730-C02238
    D-513 H Methyl H H
    Figure US20090189522A1-20090730-C02239
    Figure US20090189522A1-20090730-C02240
    D-514 H Methyl H H
    Figure US20090189522A1-20090730-C02241
    Figure US20090189522A1-20090730-C02242
    D-515 H Methyl H H
    Figure US20090189522A1-20090730-C02243
    Figure US20090189522A1-20090730-C02244
    D-516 H Methyl H H
    Figure US20090189522A1-20090730-C02245
    Figure US20090189522A1-20090730-C02246
    Figure US20090189522A1-20090730-C02247
    Figure US20090189522A1-20090730-C02248
    D-505
    Figure US20090189522A1-20090730-C02249
    Figure US20090189522A1-20090730-C02250
    D-506
    Figure US20090189522A1-20090730-C02251
    Figure US20090189522A1-20090730-C02252
    D-507
    Figure US20090189522A1-20090730-C02253
    Figure US20090189522A1-20090730-C02254
    D-508
    Figure US20090189522A1-20090730-C02255
    Figure US20090189522A1-20090730-C02256
    D-509
    Figure US20090189522A1-20090730-C02257
    Figure US20090189522A1-20090730-C02258
    D-510
    Figure US20090189522A1-20090730-C02259
    Figure US20090189522A1-20090730-C02260
    D-511
    Figure US20090189522A1-20090730-C02261
    Figure US20090189522A1-20090730-C02262
    D-512
    Figure US20090189522A1-20090730-C02263
    Figure US20090189522A1-20090730-C02264
    D-513
    Figure US20090189522A1-20090730-C02265
    Figure US20090189522A1-20090730-C02266
    D-514
    Figure US20090189522A1-20090730-C02267
    Figure US20090189522A1-20090730-C02268
    D-515
    Figure US20090189522A1-20090730-C02269
    Figure US20090189522A1-20090730-C02270
    D-516
    Figure US20090189522A1-20090730-C02271
    Figure US20090189522A1-20090730-C02272
  • TABLE 44
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02273
    Figure US20090189522A1-20090730-C02274
    D-517 H Methyl H H
    Figure US20090189522A1-20090730-C02275
    Figure US20090189522A1-20090730-C02276
    D-518 H Methyl H H
    Figure US20090189522A1-20090730-C02277
    Figure US20090189522A1-20090730-C02278
    D-519 H Methyl H H
    Figure US20090189522A1-20090730-C02279
    Figure US20090189522A1-20090730-C02280
    D-520 H Methyl H H
    Figure US20090189522A1-20090730-C02281
    Figure US20090189522A1-20090730-C02282
    D-521 H Methyl H H
    Figure US20090189522A1-20090730-C02283
    Figure US20090189522A1-20090730-C02284
    D-522 H Methyl H H
    Figure US20090189522A1-20090730-C02285
    Figure US20090189522A1-20090730-C02286
    D-523 H Methyl H H
    Figure US20090189522A1-20090730-C02287
    Figure US20090189522A1-20090730-C02288
    D-524 H Methyl H H
    Figure US20090189522A1-20090730-C02289
    Figure US20090189522A1-20090730-C02290
    D-525 H Methyl H H
    Figure US20090189522A1-20090730-C02291
    Figure US20090189522A1-20090730-C02292
    D-526 H Methyl H H
    Figure US20090189522A1-20090730-C02293
    Figure US20090189522A1-20090730-C02294
    D-527 H Methyl H H
    Figure US20090189522A1-20090730-C02295
    Figure US20090189522A1-20090730-C02296
    D-528 H Methyl H H
    Figure US20090189522A1-20090730-C02297
    Figure US20090189522A1-20090730-C02298
    Figure US20090189522A1-20090730-C02299
    Figure US20090189522A1-20090730-C02300
    D-517
    Figure US20090189522A1-20090730-C02301
    Figure US20090189522A1-20090730-C02302
    D-518
    Figure US20090189522A1-20090730-C02303
    Figure US20090189522A1-20090730-C02304
    D-519
    Figure US20090189522A1-20090730-C02305
    Figure US20090189522A1-20090730-C02306
    D-520
    Figure US20090189522A1-20090730-C02307
    Figure US20090189522A1-20090730-C02308
    D-521
    Figure US20090189522A1-20090730-C02309
    Figure US20090189522A1-20090730-C02310
    D-522
    Figure US20090189522A1-20090730-C02311
    Figure US20090189522A1-20090730-C02312
    D-523
    Figure US20090189522A1-20090730-C02313
    Figure US20090189522A1-20090730-C02314
    D-524
    Figure US20090189522A1-20090730-C02315
    Figure US20090189522A1-20090730-C02316
    D-525
    Figure US20090189522A1-20090730-C02317
    Figure US20090189522A1-20090730-C02318
    D-526
    Figure US20090189522A1-20090730-C02319
    Figure US20090189522A1-20090730-C02320
    D-527
    Figure US20090189522A1-20090730-C02321
    Figure US20090189522A1-20090730-C02322
    D-528
    Figure US20090189522A1-20090730-C02323
    Figure US20090189522A1-20090730-C02324
  • TABLE 45
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C02325
    Figure US20090189522A1-20090730-C02326
    Figure US20090189522A1-20090730-C02327
    Figure US20090189522A1-20090730-C02328
    D-529 H Isopropyl H H
    Figure US20090189522A1-20090730-C02329
    Figure US20090189522A1-20090730-C02330
    Figure US20090189522A1-20090730-C02331
    Figure US20090189522A1-20090730-C02332
    D-530 H Isopropyl H H
    Figure US20090189522A1-20090730-C02333
    Figure US20090189522A1-20090730-C02334
    Figure US20090189522A1-20090730-C02335
    Figure US20090189522A1-20090730-C02336
    D-531 H Isopropyl H H
    Figure US20090189522A1-20090730-C02337
    Figure US20090189522A1-20090730-C02338
    Figure US20090189522A1-20090730-C02339
    Figure US20090189522A1-20090730-C02340
    D-532 H Isopropyl H H
    Figure US20090189522A1-20090730-C02341
    Figure US20090189522A1-20090730-C02342
    Figure US20090189522A1-20090730-C02343
    Figure US20090189522A1-20090730-C02344
    D-533 H Isopropyl H H
    Figure US20090189522A1-20090730-C02345
    Figure US20090189522A1-20090730-C02346
    Figure US20090189522A1-20090730-C02347
    Figure US20090189522A1-20090730-C02348
    D-534 H Isopropyl H H
    Figure US20090189522A1-20090730-C02349
    Figure US20090189522A1-20090730-C02350
    Figure US20090189522A1-20090730-C02351
    Figure US20090189522A1-20090730-C02352
    D-535 H Isopropyl H H
    Figure US20090189522A1-20090730-C02353
    Figure US20090189522A1-20090730-C02354
    Figure US20090189522A1-20090730-C02355
    Figure US20090189522A1-20090730-C02356
    D-536 H Isopropyl H H
    Figure US20090189522A1-20090730-C02357
    Figure US20090189522A1-20090730-C02358
    Figure US20090189522A1-20090730-C02359
    Figure US20090189522A1-20090730-C02360
    D-537 H Isopropyl H H
    Figure US20090189522A1-20090730-C02361
    Figure US20090189522A1-20090730-C02362
    Figure US20090189522A1-20090730-C02363
    Figure US20090189522A1-20090730-C02364
    D-538 H Isopropyl H H
    Figure US20090189522A1-20090730-C02365
    Figure US20090189522A1-20090730-C02366
    Figure US20090189522A1-20090730-C02367
    Figure US20090189522A1-20090730-C02368
    D-539 H Isopropyl H H
    Figure US20090189522A1-20090730-C02369
    Figure US20090189522A1-20090730-C02370
    Figure US20090189522A1-20090730-C02371
    Figure US20090189522A1-20090730-C02372
    D-540 H Isopropyl H H
    Figure US20090189522A1-20090730-C02373
    Figure US20090189522A1-20090730-C02374
    Figure US20090189522A1-20090730-C02375
    Figure US20090189522A1-20090730-C02376
  • TABLE 46
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02377
    Figure US20090189522A1-20090730-C02378
    D-541 H Isopropyl H H
    Figure US20090189522A1-20090730-C02379
    Figure US20090189522A1-20090730-C02380
    D-542 H Isopropyl H H
    Figure US20090189522A1-20090730-C02381
    Figure US20090189522A1-20090730-C02382
    D-543 H Isopropyl H H
    Figure US20090189522A1-20090730-C02383
    Figure US20090189522A1-20090730-C02384
    D-544 H Isopropyl H H
    Figure US20090189522A1-20090730-C02385
    Figure US20090189522A1-20090730-C02386
    D-545 H Isopropyl H H
    Figure US20090189522A1-20090730-C02387
    Figure US20090189522A1-20090730-C02388
    D-546 H Isopropyl H H
    Figure US20090189522A1-20090730-C02389
    Figure US20090189522A1-20090730-C02390
    D-547 H Isopropyl H H
    Figure US20090189522A1-20090730-C02391
    Figure US20090189522A1-20090730-C02392
    D-548 H Isopropyl H H
    Figure US20090189522A1-20090730-C02393
    Figure US20090189522A1-20090730-C02394
    D-549 H Isopropyl H H
    Figure US20090189522A1-20090730-C02395
    Figure US20090189522A1-20090730-C02396
    D-550 H Isopropyl H H
    Figure US20090189522A1-20090730-C02397
    Figure US20090189522A1-20090730-C02398
    D-551 H Isopropyl H H
    Figure US20090189522A1-20090730-C02399
    Figure US20090189522A1-20090730-C02400
    D-552 H Isopropyl H H
    Figure US20090189522A1-20090730-C02401
    Figure US20090189522A1-20090730-C02402
    Figure US20090189522A1-20090730-C02403
    Figure US20090189522A1-20090730-C02404
    D-541
    Figure US20090189522A1-20090730-C02405
    Figure US20090189522A1-20090730-C02406
    D-542
    Figure US20090189522A1-20090730-C02407
    Figure US20090189522A1-20090730-C02408
    D-543
    Figure US20090189522A1-20090730-C02409
    Figure US20090189522A1-20090730-C02410
    D-544
    Figure US20090189522A1-20090730-C02411
    Figure US20090189522A1-20090730-C02412
    D-545
    Figure US20090189522A1-20090730-C02413
    Figure US20090189522A1-20090730-C02414
    D-546
    Figure US20090189522A1-20090730-C02415
    Figure US20090189522A1-20090730-C02416
    D-547
    Figure US20090189522A1-20090730-C02417
    Figure US20090189522A1-20090730-C02418
    D-548
    Figure US20090189522A1-20090730-C02419
    Figure US20090189522A1-20090730-C02420
    D-549
    Figure US20090189522A1-20090730-C02421
    Figure US20090189522A1-20090730-C02422
    D-550
    Figure US20090189522A1-20090730-C02423
    Figure US20090189522A1-20090730-C02424
    D-551
    Figure US20090189522A1-20090730-C02425
    Figure US20090189522A1-20090730-C02426
    D-552
    Figure US20090189522A1-20090730-C02427
    Figure US20090189522A1-20090730-C02428
  • TABLE 47
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02429
    Figure US20090189522A1-20090730-C02430
    D-553 H Isopropyl H H
    Figure US20090189522A1-20090730-C02431
    Figure US20090189522A1-20090730-C02432
    D-554 H Isopropyl H H
    Figure US20090189522A1-20090730-C02433
    Figure US20090189522A1-20090730-C02434
    D-555 H Isopropyl H H
    Figure US20090189522A1-20090730-C02435
    Figure US20090189522A1-20090730-C02436
    D-556 H Isopropyl H H
    Figure US20090189522A1-20090730-C02437
    Figure US20090189522A1-20090730-C02438
    D-557 H Isopropyl H H
    Figure US20090189522A1-20090730-C02439
    Figure US20090189522A1-20090730-C02440
    D-558 H Isopropyl H H
    Figure US20090189522A1-20090730-C02441
    Figure US20090189522A1-20090730-C02442
    D-559 H Isopropyl H H
    Figure US20090189522A1-20090730-C02443
    Figure US20090189522A1-20090730-C02444
    D-560 H Isopropyl H H
    Figure US20090189522A1-20090730-C02445
    Figure US20090189522A1-20090730-C02446
    D-561 H Isopropyl H H
    Figure US20090189522A1-20090730-C02447
    Figure US20090189522A1-20090730-C02448
    D-562 H Isopropyl H H
    Figure US20090189522A1-20090730-C02449
    Figure US20090189522A1-20090730-C02450
    D-563 H Isopropyl H H
    Figure US20090189522A1-20090730-C02451
    Figure US20090189522A1-20090730-C02452
    D-564 H Isopropyl H H
    Figure US20090189522A1-20090730-C02453
    Figure US20090189522A1-20090730-C02454
    Figure US20090189522A1-20090730-C02455
    Figure US20090189522A1-20090730-C02456
    D-553
    Figure US20090189522A1-20090730-C02457
    Figure US20090189522A1-20090730-C02458
    D-554
    Figure US20090189522A1-20090730-C02459
    Figure US20090189522A1-20090730-C02460
    D-555
    Figure US20090189522A1-20090730-C02461
    Figure US20090189522A1-20090730-C02462
    D-556
    Figure US20090189522A1-20090730-C02463
    Figure US20090189522A1-20090730-C02464
    D-557
    Figure US20090189522A1-20090730-C02465
    Figure US20090189522A1-20090730-C02466
    D-558
    Figure US20090189522A1-20090730-C02467
    Figure US20090189522A1-20090730-C02468
    D-559
    Figure US20090189522A1-20090730-C02469
    Figure US20090189522A1-20090730-C02470
    D-560
    Figure US20090189522A1-20090730-C02471
    Figure US20090189522A1-20090730-C02472
    D-561
    Figure US20090189522A1-20090730-C02473
    Figure US20090189522A1-20090730-C02474
    D-562
    Figure US20090189522A1-20090730-C02475
    Figure US20090189522A1-20090730-C02476
    D-563
    Figure US20090189522A1-20090730-C02477
    Figure US20090189522A1-20090730-C02478
    D-564
    Figure US20090189522A1-20090730-C02479
    Figure US20090189522A1-20090730-C02480
  • TABLE 48
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02481
    Figure US20090189522A1-20090730-C02482
    D-565 H Isopropyl H H
    Figure US20090189522A1-20090730-C02483
    Figure US20090189522A1-20090730-C02484
    D-566 H Isopropyl H H
    Figure US20090189522A1-20090730-C02485
    Figure US20090189522A1-20090730-C02486
    D-567 H Isopropyl H H
    Figure US20090189522A1-20090730-C02487
    Figure US20090189522A1-20090730-C02488
    D-568 H Isopropyl H H
    Figure US20090189522A1-20090730-C02489
    Figure US20090189522A1-20090730-C02490
    D-569 H Isopropyl H H
    Figure US20090189522A1-20090730-C02491
    Figure US20090189522A1-20090730-C02492
    D-570 H Isopropyl H H
    Figure US20090189522A1-20090730-C02493
    Figure US20090189522A1-20090730-C02494
    D-571 H Isopropyl H H
    Figure US20090189522A1-20090730-C02495
    Figure US20090189522A1-20090730-C02496
    D-572 H Isopropyl H H
    Figure US20090189522A1-20090730-C02497
    Figure US20090189522A1-20090730-C02498
    D-573 H Isopropyl H H
    Figure US20090189522A1-20090730-C02499
    Figure US20090189522A1-20090730-C02500
    D-574 H Isopropyl H H
    Figure US20090189522A1-20090730-C02501
    Figure US20090189522A1-20090730-C02502
    D-575 H Isopropyl H H
    Figure US20090189522A1-20090730-C02503
    Figure US20090189522A1-20090730-C02504
    D-576 H Isopropyl H H
    Figure US20090189522A1-20090730-C02505
    Figure US20090189522A1-20090730-C02506
    Figure US20090189522A1-20090730-C02507
    Figure US20090189522A1-20090730-C02508
    D-565
    Figure US20090189522A1-20090730-C02509
    Figure US20090189522A1-20090730-C02510
    D-566
    Figure US20090189522A1-20090730-C02511
    Figure US20090189522A1-20090730-C02512
    D-567
    Figure US20090189522A1-20090730-C02513
    Figure US20090189522A1-20090730-C02514
    D-568
    Figure US20090189522A1-20090730-C02515
    Figure US20090189522A1-20090730-C02516
    D-569
    Figure US20090189522A1-20090730-C02517
    Figure US20090189522A1-20090730-C02518
    D-570
    Figure US20090189522A1-20090730-C02519
    Figure US20090189522A1-20090730-C02520
    D-571
    Figure US20090189522A1-20090730-C02521
    Figure US20090189522A1-20090730-C02522
    D-572
    Figure US20090189522A1-20090730-C02523
    Figure US20090189522A1-20090730-C02524
    D-573
    Figure US20090189522A1-20090730-C02525
    Figure US20090189522A1-20090730-C02526
    D-574
    Figure US20090189522A1-20090730-C02527
    Figure US20090189522A1-20090730-C02528
    D-575
    Figure US20090189522A1-20090730-C02529
    Figure US20090189522A1-20090730-C02530
    D-576
    Figure US20090189522A1-20090730-C02531
    Figure US20090189522A1-20090730-C02532
  • TABLE 49
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C02533
    Figure US20090189522A1-20090730-C02534
    Figure US20090189522A1-20090730-C02535
    Figure US20090189522A1-20090730-C02536
    D-577 H t-butyl H H
    Figure US20090189522A1-20090730-C02537
    Figure US20090189522A1-20090730-C02538
    Figure US20090189522A1-20090730-C02539
    Figure US20090189522A1-20090730-C02540
    D-578 H t-butyl H H
    Figure US20090189522A1-20090730-C02541
    Figure US20090189522A1-20090730-C02542
    Figure US20090189522A1-20090730-C02543
    Figure US20090189522A1-20090730-C02544
    D-579 H t-butyl H H
    Figure US20090189522A1-20090730-C02545
    Figure US20090189522A1-20090730-C02546
    Figure US20090189522A1-20090730-C02547
    Figure US20090189522A1-20090730-C02548
    D-580 H t-butyl H H
    Figure US20090189522A1-20090730-C02549
    Figure US20090189522A1-20090730-C02550
    Figure US20090189522A1-20090730-C02551
    Figure US20090189522A1-20090730-C02552
    D-581 H t-butyl H H
    Figure US20090189522A1-20090730-C02553
    Figure US20090189522A1-20090730-C02554
    Figure US20090189522A1-20090730-C02555
    Figure US20090189522A1-20090730-C02556
    D-582 H t-butyl H H
    Figure US20090189522A1-20090730-C02557
    Figure US20090189522A1-20090730-C02558
    Figure US20090189522A1-20090730-C02559
    Figure US20090189522A1-20090730-C02560
    D-583 H t-butyl H H
    Figure US20090189522A1-20090730-C02561
    Figure US20090189522A1-20090730-C02562
    Figure US20090189522A1-20090730-C02563
    Figure US20090189522A1-20090730-C02564
    D-584 H t-butyl H H
    Figure US20090189522A1-20090730-C02565
    Figure US20090189522A1-20090730-C02566
    Figure US20090189522A1-20090730-C02567
    Figure US20090189522A1-20090730-C02568
    D-585 H t-butyl H H
    Figure US20090189522A1-20090730-C02569
    Figure US20090189522A1-20090730-C02570
    Figure US20090189522A1-20090730-C02571
    Figure US20090189522A1-20090730-C02572
    D-586 H t-butyl H H
    Figure US20090189522A1-20090730-C02573
    Figure US20090189522A1-20090730-C02574
    Figure US20090189522A1-20090730-C02575
    Figure US20090189522A1-20090730-C02576
    D-587 H t-butyl H H
    Figure US20090189522A1-20090730-C02577
    Figure US20090189522A1-20090730-C02578
    Figure US20090189522A1-20090730-C02579
    Figure US20090189522A1-20090730-C02580
    D-588 H t-butyl H H
    Figure US20090189522A1-20090730-C02581
    Figure US20090189522A1-20090730-C02582
    Figure US20090189522A1-20090730-C02583
    Figure US20090189522A1-20090730-C02584
  • TABLE 50
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02585
    Figure US20090189522A1-20090730-C02586
    D-589 H t-butyl H H
    Figure US20090189522A1-20090730-C02587
    Figure US20090189522A1-20090730-C02588
    D-590 H t-butyl H H
    Figure US20090189522A1-20090730-C02589
    Figure US20090189522A1-20090730-C02590
    D-591 H t-butyl H H
    Figure US20090189522A1-20090730-C02591
    Figure US20090189522A1-20090730-C02592
    D-592 H t-butyl H H
    Figure US20090189522A1-20090730-C02593
    Figure US20090189522A1-20090730-C02594
    D-593 H t-butyl H H
    Figure US20090189522A1-20090730-C02595
    Figure US20090189522A1-20090730-C02596
    D-594 H t-butyl H H
    Figure US20090189522A1-20090730-C02597
    Figure US20090189522A1-20090730-C02598
    D-595 H t-butyl H H
    Figure US20090189522A1-20090730-C02599
    Figure US20090189522A1-20090730-C02600
    D-596 H t-butyl H H
    Figure US20090189522A1-20090730-C02601
    Figure US20090189522A1-20090730-C02602
    D-597 H t-butyl H H
    Figure US20090189522A1-20090730-C02603
    Figure US20090189522A1-20090730-C02604
    D-598 H t-butyl H H
    Figure US20090189522A1-20090730-C02605
    Figure US20090189522A1-20090730-C02606
    D-599 H t-butyl H H
    Figure US20090189522A1-20090730-C02607
    Figure US20090189522A1-20090730-C02608
    D-600 H t-butyl H H
    Figure US20090189522A1-20090730-C02609
    Figure US20090189522A1-20090730-C02610
    Figure US20090189522A1-20090730-C02611
    Figure US20090189522A1-20090730-C02612
    D-589
    Figure US20090189522A1-20090730-C02613
    Figure US20090189522A1-20090730-C02614
    D-590
    Figure US20090189522A1-20090730-C02615
    Figure US20090189522A1-20090730-C02616
    D-591
    Figure US20090189522A1-20090730-C02617
    Figure US20090189522A1-20090730-C02618
    D-592
    Figure US20090189522A1-20090730-C02619
    Figure US20090189522A1-20090730-C02620
    D-593
    Figure US20090189522A1-20090730-C02621
    Figure US20090189522A1-20090730-C02622
    D-594
    Figure US20090189522A1-20090730-C02623
    Figure US20090189522A1-20090730-C02624
    D-595
    Figure US20090189522A1-20090730-C02625
    Figure US20090189522A1-20090730-C02626
    D-596
    Figure US20090189522A1-20090730-C02627
    Figure US20090189522A1-20090730-C02628
    D-597
    Figure US20090189522A1-20090730-C02629
    Figure US20090189522A1-20090730-C02630
    D-598
    Figure US20090189522A1-20090730-C02631
    Figure US20090189522A1-20090730-C02632
    D-599
    Figure US20090189522A1-20090730-C02633
    Figure US20090189522A1-20090730-C02634
    D-600
    Figure US20090189522A1-20090730-C02635
    Figure US20090189522A1-20090730-C02636
  • TABLE 51
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02637
    Figure US20090189522A1-20090730-C02638
    D-601 H t-butyl H H
    Figure US20090189522A1-20090730-C02639
    Figure US20090189522A1-20090730-C02640
    D-602 H t-butyl H H
    Figure US20090189522A1-20090730-C02641
    Figure US20090189522A1-20090730-C02642
    D-603 H t-butyl H H
    Figure US20090189522A1-20090730-C02643
    Figure US20090189522A1-20090730-C02644
    D-604 H t-butyl H H
    Figure US20090189522A1-20090730-C02645
    Figure US20090189522A1-20090730-C02646
    D-605 H t-butyl H H
    Figure US20090189522A1-20090730-C02647
    Figure US20090189522A1-20090730-C02648
    D-606 H t-butyl H H
    Figure US20090189522A1-20090730-C02649
    Figure US20090189522A1-20090730-C02650
    D-607 H t-butyl H H
    Figure US20090189522A1-20090730-C02651
    Figure US20090189522A1-20090730-C02652
    D-608 H t-butyl H H
    Figure US20090189522A1-20090730-C02653
    Figure US20090189522A1-20090730-C02654
    D-609 H t-butyl H H
    Figure US20090189522A1-20090730-C02655
    Figure US20090189522A1-20090730-C02656
    D-610 H t-butyl H H
    Figure US20090189522A1-20090730-C02657
    Figure US20090189522A1-20090730-C02658
    D-611 H t-butyl H H
    Figure US20090189522A1-20090730-C02659
    Figure US20090189522A1-20090730-C02660
    D-612 H t-butyl H H
    Figure US20090189522A1-20090730-C02661
    Figure US20090189522A1-20090730-C02662
    Figure US20090189522A1-20090730-C02663
    Figure US20090189522A1-20090730-C02664
    D-601
    Figure US20090189522A1-20090730-C02665
    Figure US20090189522A1-20090730-C02666
    D-602
    Figure US20090189522A1-20090730-C02667
    Figure US20090189522A1-20090730-C02668
    D-603
    Figure US20090189522A1-20090730-C02669
    Figure US20090189522A1-20090730-C02670
    D-604
    Figure US20090189522A1-20090730-C02671
    Figure US20090189522A1-20090730-C02672
    D-605
    Figure US20090189522A1-20090730-C02673
    Figure US20090189522A1-20090730-C02674
    D-606
    Figure US20090189522A1-20090730-C02675
    Figure US20090189522A1-20090730-C02676
    D-607
    Figure US20090189522A1-20090730-C02677
    Figure US20090189522A1-20090730-C02678
    D-608
    Figure US20090189522A1-20090730-C02679
    Figure US20090189522A1-20090730-C02680
    D-609
    Figure US20090189522A1-20090730-C02681
    Figure US20090189522A1-20090730-C02682
    D-610
    Figure US20090189522A1-20090730-C02683
    Figure US20090189522A1-20090730-C02684
    D-611
    Figure US20090189522A1-20090730-C02685
    Figure US20090189522A1-20090730-C02686
    D-612
    Figure US20090189522A1-20090730-C02687
    Figure US20090189522A1-20090730-C02688
  • TABLE 52
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02689
    Figure US20090189522A1-20090730-C02690
    D-613 H t-butyl H H
    Figure US20090189522A1-20090730-C02691
    Figure US20090189522A1-20090730-C02692
    D-614 H t-butyl H H
    Figure US20090189522A1-20090730-C02693
    Figure US20090189522A1-20090730-C02694
    D-615 H t-butyl H H
    Figure US20090189522A1-20090730-C02695
    Figure US20090189522A1-20090730-C02696
    D-616 H t-butyl H H
    Figure US20090189522A1-20090730-C02697
    Figure US20090189522A1-20090730-C02698
    D-617 H t-butyl H H
    Figure US20090189522A1-20090730-C02699
    Figure US20090189522A1-20090730-C02700
    D-618 H t-butyl H H
    Figure US20090189522A1-20090730-C02701
    Figure US20090189522A1-20090730-C02702
    D-619 H t-butyl H H
    Figure US20090189522A1-20090730-C02703
    Figure US20090189522A1-20090730-C02704
    D-620 H t-butyl H H
    Figure US20090189522A1-20090730-C02705
    Figure US20090189522A1-20090730-C02706
    D-621 H t-butyl H H
    Figure US20090189522A1-20090730-C02707
    Figure US20090189522A1-20090730-C02708
    D-622 H t-butyl H H
    Figure US20090189522A1-20090730-C02709
    Figure US20090189522A1-20090730-C02710
    D-623 H t-butyl H H
    Figure US20090189522A1-20090730-C02711
    Figure US20090189522A1-20090730-C02712
    D-624 H t-butyl H H
    Figure US20090189522A1-20090730-C02713
    Figure US20090189522A1-20090730-C02714
    Figure US20090189522A1-20090730-C02715
    Figure US20090189522A1-20090730-C02716
    D-613
    Figure US20090189522A1-20090730-C02717
    Figure US20090189522A1-20090730-C02718
    D-614
    Figure US20090189522A1-20090730-C02719
    Figure US20090189522A1-20090730-C02720
    D-615
    Figure US20090189522A1-20090730-C02721
    Figure US20090189522A1-20090730-C02722
    D-616
    Figure US20090189522A1-20090730-C02723
    Figure US20090189522A1-20090730-C02724
    D-617
    Figure US20090189522A1-20090730-C02725
    Figure US20090189522A1-20090730-C02726
    D-618
    Figure US20090189522A1-20090730-C02727
    Figure US20090189522A1-20090730-C02728
    D-619
    Figure US20090189522A1-20090730-C02729
    Figure US20090189522A1-20090730-C02730
    D-620
    Figure US20090189522A1-20090730-C02731
    Figure US20090189522A1-20090730-C02732
    D-621
    Figure US20090189522A1-20090730-C02733
    Figure US20090189522A1-20090730-C02734
    D-622
    Figure US20090189522A1-20090730-C02735
    Figure US20090189522A1-20090730-C02736
    D-623
    Figure US20090189522A1-20090730-C02737
    Figure US20090189522A1-20090730-C02738
    D-624
    Figure US20090189522A1-20090730-C02739
    Figure US20090189522A1-20090730-C02740
  • TABLE 53
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C02741
    Figure US20090189522A1-20090730-C02742
    Figure US20090189522A1-20090730-C02743
    Figure US20090189522A1-20090730-C02744
    D-625 H Phenyl H H
    Figure US20090189522A1-20090730-C02745
    Figure US20090189522A1-20090730-C02746
    Figure US20090189522A1-20090730-C02747
    Figure US20090189522A1-20090730-C02748
    D-626 H Phenyl H H
    Figure US20090189522A1-20090730-C02749
    Figure US20090189522A1-20090730-C02750
    Figure US20090189522A1-20090730-C02751
    Figure US20090189522A1-20090730-C02752
    D-627 H Phenyl H H
    Figure US20090189522A1-20090730-C02753
    Figure US20090189522A1-20090730-C02754
    Figure US20090189522A1-20090730-C02755
    Figure US20090189522A1-20090730-C02756
    D-628 H Phenyl H H
    Figure US20090189522A1-20090730-C02757
    Figure US20090189522A1-20090730-C02758
    Figure US20090189522A1-20090730-C02759
    Figure US20090189522A1-20090730-C02760
    D-629 H Phenyl H H
    Figure US20090189522A1-20090730-C02761
    Figure US20090189522A1-20090730-C02762
    Figure US20090189522A1-20090730-C02763
    Figure US20090189522A1-20090730-C02764
    D-630 H Phenyl H H
    Figure US20090189522A1-20090730-C02765
    Figure US20090189522A1-20090730-C02766
    Figure US20090189522A1-20090730-C02767
    Figure US20090189522A1-20090730-C02768
    D-631 H Phenyl H H
    Figure US20090189522A1-20090730-C02769
    Figure US20090189522A1-20090730-C02770
    Figure US20090189522A1-20090730-C02771
    Figure US20090189522A1-20090730-C02772
    D-632 H Phenyl H H
    Figure US20090189522A1-20090730-C02773
    Figure US20090189522A1-20090730-C02774
    Figure US20090189522A1-20090730-C02775
    Figure US20090189522A1-20090730-C02776
    D-633 H Phenyl H H
    Figure US20090189522A1-20090730-C02777
    Figure US20090189522A1-20090730-C02778
    Figure US20090189522A1-20090730-C02779
    Figure US20090189522A1-20090730-C02780
    D-634 H Phenyl H H
    Figure US20090189522A1-20090730-C02781
    Figure US20090189522A1-20090730-C02782
    Figure US20090189522A1-20090730-C02783
    Figure US20090189522A1-20090730-C02784
    D-635 H Phenyl H H
    Figure US20090189522A1-20090730-C02785
    Figure US20090189522A1-20090730-C02786
    Figure US20090189522A1-20090730-C02787
    Figure US20090189522A1-20090730-C02788
    D-636 H Phenyl H H
    Figure US20090189522A1-20090730-C02789
    Figure US20090189522A1-20090730-C02790
    Figure US20090189522A1-20090730-C02791
    Figure US20090189522A1-20090730-C02792
  • TABLE 54
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02793
    Figure US20090189522A1-20090730-C02794
    D-637 H Phenyl H H
    Figure US20090189522A1-20090730-C02795
    Figure US20090189522A1-20090730-C02796
    D-638 H Phenyl H H
    Figure US20090189522A1-20090730-C02797
    Figure US20090189522A1-20090730-C02798
    D-639 H Phenyl H H
    Figure US20090189522A1-20090730-C02799
    Figure US20090189522A1-20090730-C02800
    D-640 H Phenyl H H
    Figure US20090189522A1-20090730-C02801
    Figure US20090189522A1-20090730-C02802
    D-641 H Phenyl H H
    Figure US20090189522A1-20090730-C02803
    Figure US20090189522A1-20090730-C02804
    D-642 H Phenyl H H
    Figure US20090189522A1-20090730-C02805
    Figure US20090189522A1-20090730-C02806
    D-643 H Phenyl H H
    Figure US20090189522A1-20090730-C02807
    Figure US20090189522A1-20090730-C02808
    D-644 H Phenyl H H
    Figure US20090189522A1-20090730-C02809
    Figure US20090189522A1-20090730-C02810
    D-645 H Phenyl H H
    Figure US20090189522A1-20090730-C02811
    Figure US20090189522A1-20090730-C02812
    D-646 H Phenyl H H
    Figure US20090189522A1-20090730-C02813
    Figure US20090189522A1-20090730-C02814
    D-647 H Phenyl H H
    Figure US20090189522A1-20090730-C02815
    Figure US20090189522A1-20090730-C02816
    D-648 H Phenyl H H
    Figure US20090189522A1-20090730-C02817
    Figure US20090189522A1-20090730-C02818
    Figure US20090189522A1-20090730-C02819
    Figure US20090189522A1-20090730-C02820
    D-637
    Figure US20090189522A1-20090730-C02821
    Figure US20090189522A1-20090730-C02822
    D-638
    Figure US20090189522A1-20090730-C02823
    Figure US20090189522A1-20090730-C02824
    D-639
    Figure US20090189522A1-20090730-C02825
    Figure US20090189522A1-20090730-C02826
    D-640
    Figure US20090189522A1-20090730-C02827
    Figure US20090189522A1-20090730-C02828
    D-641
    Figure US20090189522A1-20090730-C02829
    Figure US20090189522A1-20090730-C02830
    D-642
    Figure US20090189522A1-20090730-C02831
    Figure US20090189522A1-20090730-C02832
    D-643
    Figure US20090189522A1-20090730-C02833
    Figure US20090189522A1-20090730-C02834
    D-644
    Figure US20090189522A1-20090730-C02835
    Figure US20090189522A1-20090730-C02836
    D-645
    Figure US20090189522A1-20090730-C02837
    Figure US20090189522A1-20090730-C02838
    D-646
    Figure US20090189522A1-20090730-C02839
    Figure US20090189522A1-20090730-C02840
    D-647
    Figure US20090189522A1-20090730-C02841
    Figure US20090189522A1-20090730-C02842
    D-648
    Figure US20090189522A1-20090730-C02843
    Figure US20090189522A1-20090730-C02844
  • TABLE 55
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02845
    Figure US20090189522A1-20090730-C02846
    D-649 H Phenyl H H
    Figure US20090189522A1-20090730-C02847
    Figure US20090189522A1-20090730-C02848
    D-650 H Phenyl H H
    Figure US20090189522A1-20090730-C02849
    Figure US20090189522A1-20090730-C02850
    D-651 H Phenyl H H
    Figure US20090189522A1-20090730-C02851
    Figure US20090189522A1-20090730-C02852
    D-652 H Phenyl H H
    Figure US20090189522A1-20090730-C02853
    Figure US20090189522A1-20090730-C02854
    D-653 H Phenyl H H
    Figure US20090189522A1-20090730-C02855
    Figure US20090189522A1-20090730-C02856
    D-654 H Phenyl H H
    Figure US20090189522A1-20090730-C02857
    Figure US20090189522A1-20090730-C02858
    D-655 H Phenyl H H
    Figure US20090189522A1-20090730-C02859
    Figure US20090189522A1-20090730-C02860
    D-656 H Phenyl H H
    Figure US20090189522A1-20090730-C02861
    Figure US20090189522A1-20090730-C02862
    D-657 H Phenyl H H
    Figure US20090189522A1-20090730-C02863
    Figure US20090189522A1-20090730-C02864
    D-658 H Phenyl H H
    Figure US20090189522A1-20090730-C02865
    Figure US20090189522A1-20090730-C02866
    D-659 H Phenyl H H
    Figure US20090189522A1-20090730-C02867
    Figure US20090189522A1-20090730-C02868
    D-660 H Phenyl H H
    Figure US20090189522A1-20090730-C02869
    Figure US20090189522A1-20090730-C02870
    Figure US20090189522A1-20090730-C02871
    Figure US20090189522A1-20090730-C02872
    D-649
    Figure US20090189522A1-20090730-C02873
    Figure US20090189522A1-20090730-C02874
    D-650
    Figure US20090189522A1-20090730-C02875
    Figure US20090189522A1-20090730-C02876
    D-651
    Figure US20090189522A1-20090730-C02877
    Figure US20090189522A1-20090730-C02878
    D-652
    Figure US20090189522A1-20090730-C02879
    Figure US20090189522A1-20090730-C02880
    D-653
    Figure US20090189522A1-20090730-C02881
    Figure US20090189522A1-20090730-C02882
    D-654
    Figure US20090189522A1-20090730-C02883
    Figure US20090189522A1-20090730-C02884
    D-655
    Figure US20090189522A1-20090730-C02885
    Figure US20090189522A1-20090730-C02886
    D-656
    Figure US20090189522A1-20090730-C02887
    Figure US20090189522A1-20090730-C02888
    D-657
    Figure US20090189522A1-20090730-C02889
    Figure US20090189522A1-20090730-C02890
    D-658
    Figure US20090189522A1-20090730-C02891
    Figure US20090189522A1-20090730-C02892
    D-659
    Figure US20090189522A1-20090730-C02893
    Figure US20090189522A1-20090730-C02894
    D-660
    Figure US20090189522A1-20090730-C02895
    Figure US20090189522A1-20090730-C02896
  • TABLE 56
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C02897
    Figure US20090189522A1-20090730-C02898
    D-661 H Phenyl H H
    Figure US20090189522A1-20090730-C02899
    Figure US20090189522A1-20090730-C02900
    D-662 H Phenyl H H
    Figure US20090189522A1-20090730-C02901
    Figure US20090189522A1-20090730-C02902
    D-663 H Phenyl H H
    Figure US20090189522A1-20090730-C02903
    Figure US20090189522A1-20090730-C02904
    D-664 H Phenyl H H
    Figure US20090189522A1-20090730-C02905
    Figure US20090189522A1-20090730-C02906
    D-665 H Phenyl H H
    Figure US20090189522A1-20090730-C02907
    Figure US20090189522A1-20090730-C02908
    D-666 H Phenyl H H
    Figure US20090189522A1-20090730-C02909
    Figure US20090189522A1-20090730-C02910
    D-667 H Phenyl H H
    Figure US20090189522A1-20090730-C02911
    Figure US20090189522A1-20090730-C02912
    D-668 H Phenyl H H
    Figure US20090189522A1-20090730-C02913
    Figure US20090189522A1-20090730-C02914
    D-669 H Phenyl H H
    Figure US20090189522A1-20090730-C02915
    Figure US20090189522A1-20090730-C02916
    D-670 H Phenyl H H
    Figure US20090189522A1-20090730-C02917
    Figure US20090189522A1-20090730-C02918
    D-671 H Phenyl H H
    Figure US20090189522A1-20090730-C02919
    Figure US20090189522A1-20090730-C02920
    D-672 H Phenyl H H
    Figure US20090189522A1-20090730-C02921
    Figure US20090189522A1-20090730-C02922
    Figure US20090189522A1-20090730-C02923
    Figure US20090189522A1-20090730-C02924
    D-661
    Figure US20090189522A1-20090730-C02925
    Figure US20090189522A1-20090730-C02926
    D-662
    Figure US20090189522A1-20090730-C02927
    Figure US20090189522A1-20090730-C02928
    D-663
    Figure US20090189522A1-20090730-C02929
    Figure US20090189522A1-20090730-C02930
    D-664
    Figure US20090189522A1-20090730-C02931
    Figure US20090189522A1-20090730-C02932
    D-665
    Figure US20090189522A1-20090730-C02933
    Figure US20090189522A1-20090730-C02934
    D-666
    Figure US20090189522A1-20090730-C02935
    Figure US20090189522A1-20090730-C02936
    D-667
    Figure US20090189522A1-20090730-C02937
    Figure US20090189522A1-20090730-C02938
    D-668
    Figure US20090189522A1-20090730-C02939
    Figure US20090189522A1-20090730-C02940
    D-669
    Figure US20090189522A1-20090730-C02941
    Figure US20090189522A1-20090730-C02942
    D-670
    Figure US20090189522A1-20090730-C02943
    Figure US20090189522A1-20090730-C02944
    D-671
    Figure US20090189522A1-20090730-C02945
    Figure US20090189522A1-20090730-C02946
    D-672
    Figure US20090189522A1-20090730-C02947
    Figure US20090189522A1-20090730-C02948
  • TABLE 57
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C02949
    Figure US20090189522A1-20090730-C02950
    Figure US20090189522A1-20090730-C02951
    Figure US20090189522A1-20090730-C02952
    D-673 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02953
    Figure US20090189522A1-20090730-C02954
    Figure US20090189522A1-20090730-C02955
    Figure US20090189522A1-20090730-C02956
    D-674 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02957
    Figure US20090189522A1-20090730-C02958
    Figure US20090189522A1-20090730-C02959
    Figure US20090189522A1-20090730-C02960
    D-675 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02961
    Figure US20090189522A1-20090730-C02962
    Figure US20090189522A1-20090730-C02963
    Figure US20090189522A1-20090730-C02964
    D-676 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02965
    Figure US20090189522A1-20090730-C02966
    Figure US20090189522A1-20090730-C02967
    Figure US20090189522A1-20090730-C02968
    D-677 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02969
    Figure US20090189522A1-20090730-C02970
    Figure US20090189522A1-20090730-C02971
    Figure US20090189522A1-20090730-C02972
    D-678 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02973
    Figure US20090189522A1-20090730-C02974
    Figure US20090189522A1-20090730-C02975
    Figure US20090189522A1-20090730-C02976
    D-679 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02977
    Figure US20090189522A1-20090730-C02978
    Figure US20090189522A1-20090730-C02979
    Figure US20090189522A1-20090730-C02980
    D-680 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02981
    Figure US20090189522A1-20090730-C02982
    Figure US20090189522A1-20090730-C02983
    Figure US20090189522A1-20090730-C02984
    D-681 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02985
    Figure US20090189522A1-20090730-C02986
    Figure US20090189522A1-20090730-C02987
    Figure US20090189522A1-20090730-C02988
    D-682 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02989
    Figure US20090189522A1-20090730-C02990
    Figure US20090189522A1-20090730-C02991
    Figure US20090189522A1-20090730-C02992
    D-683 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02993
    Figure US20090189522A1-20090730-C02994
    Figure US20090189522A1-20090730-C02995
    Figure US20090189522A1-20090730-C02996
    D-684 H Methyl H Methyl
    Figure US20090189522A1-20090730-C02997
    Figure US20090189522A1-20090730-C02998
    Figure US20090189522A1-20090730-C02999
    Figure US20090189522A1-20090730-C03000
  • TABLE 58
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03001
    Figure US20090189522A1-20090730-C03002
    Figure US20090189522A1-20090730-C03003
    Figure US20090189522A1-20090730-C03004
    D-685 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03005
    Figure US20090189522A1-20090730-C03006
    Figure US20090189522A1-20090730-C03007
    Figure US20090189522A1-20090730-C03008
    D-686 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03009
    Figure US20090189522A1-20090730-C03010
    Figure US20090189522A1-20090730-C03011
    Figure US20090189522A1-20090730-C03012
    D-687 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03013
    Figure US20090189522A1-20090730-C03014
    Figure US20090189522A1-20090730-C03015
    Figure US20090189522A1-20090730-C03016
    D-688 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03017
    Figure US20090189522A1-20090730-C03018
    Figure US20090189522A1-20090730-C03019
    Figure US20090189522A1-20090730-C03020
    D-689 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03021
    Figure US20090189522A1-20090730-C03022
    Figure US20090189522A1-20090730-C03023
    Figure US20090189522A1-20090730-C03024
    D-690 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03025
    Figure US20090189522A1-20090730-C03026
    Figure US20090189522A1-20090730-C03027
    Figure US20090189522A1-20090730-C03028
    D-691 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03029
    Figure US20090189522A1-20090730-C03030
    Figure US20090189522A1-20090730-C03031
    Figure US20090189522A1-20090730-C03032
    D-692 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03033
    Figure US20090189522A1-20090730-C03034
    Figure US20090189522A1-20090730-C03035
    Figure US20090189522A1-20090730-C03036
    D-693 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03037
    Figure US20090189522A1-20090730-C03038
    Figure US20090189522A1-20090730-C03039
    Figure US20090189522A1-20090730-C03040
    D-694 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03041
    Figure US20090189522A1-20090730-C03042
    Figure US20090189522A1-20090730-C03043
    Figure US20090189522A1-20090730-C03044
    D-695 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03045
    Figure US20090189522A1-20090730-C03046
    Figure US20090189522A1-20090730-C03047
    Figure US20090189522A1-20090730-C03048
    D-696 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03049
    Figure US20090189522A1-20090730-C03050
    Figure US20090189522A1-20090730-C03051
    Figure US20090189522A1-20090730-C03052
  • TABLE 59
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03053
    Figure US20090189522A1-20090730-C03054
    D-697 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03055
    Figure US20090189522A1-20090730-C03056
    D-698 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03057
    Figure US20090189522A1-20090730-C03058
    D-699 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03059
    Figure US20090189522A1-20090730-C03060
    D-700 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03061
    Figure US20090189522A1-20090730-C03062
    D-701 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03063
    Figure US20090189522A1-20090730-C03064
    D-702 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03065
    Figure US20090189522A1-20090730-C03066
    D-703 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03067
    Figure US20090189522A1-20090730-C03068
    D-704 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03069
    Figure US20090189522A1-20090730-C03070
    D-705 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03071
    Figure US20090189522A1-20090730-C03072
    D-706 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03073
    Figure US20090189522A1-20090730-C03074
    D-707 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03075
    Figure US20090189522A1-20090730-C03076
    D-708 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03077
    Figure US20090189522A1-20090730-C03078
    Figure US20090189522A1-20090730-C03079
    Figure US20090189522A1-20090730-C03080
    D-697
    Figure US20090189522A1-20090730-C03081
    Figure US20090189522A1-20090730-C03082
    D-698
    Figure US20090189522A1-20090730-C03083
    Figure US20090189522A1-20090730-C03084
    D-699
    Figure US20090189522A1-20090730-C03085
    Figure US20090189522A1-20090730-C03086
    D-700
    Figure US20090189522A1-20090730-C03087
    Figure US20090189522A1-20090730-C03088
    D-701
    Figure US20090189522A1-20090730-C03089
    Figure US20090189522A1-20090730-C03090
    D-702
    Figure US20090189522A1-20090730-C03091
    Figure US20090189522A1-20090730-C03092
    D-703
    Figure US20090189522A1-20090730-C03093
    Figure US20090189522A1-20090730-C03094
    D-704
    Figure US20090189522A1-20090730-C03095
    Figure US20090189522A1-20090730-C03096
    D-705
    Figure US20090189522A1-20090730-C03097
    Figure US20090189522A1-20090730-C03098
    D-706
    Figure US20090189522A1-20090730-C03099
    Figure US20090189522A1-20090730-C03100
    D-707
    Figure US20090189522A1-20090730-C03101
    Figure US20090189522A1-20090730-C03102
    D-708
    Figure US20090189522A1-20090730-C03103
    Figure US20090189522A1-20090730-C03104
  • TABLE 60
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03105
    Figure US20090189522A1-20090730-C03106
    D-709 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03107
    Figure US20090189522A1-20090730-C03108
    D-710 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03109
    Figure US20090189522A1-20090730-C03110
    D-711 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03111
    Figure US20090189522A1-20090730-C03112
    D-712 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03113
    Figure US20090189522A1-20090730-C03114
    D-713 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03115
    Figure US20090189522A1-20090730-C03116
    D-714 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03117
    Figure US20090189522A1-20090730-C03118
    D-715 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03119
    Figure US20090189522A1-20090730-C03120
    D-716 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03121
    Figure US20090189522A1-20090730-C03122
    D-717 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03123
    Figure US20090189522A1-20090730-C03124
    D-718 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03125
    Figure US20090189522A1-20090730-C03126
    D-719 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03127
    Figure US20090189522A1-20090730-C03128
    D-720 H Methyl H Methyl
    Figure US20090189522A1-20090730-C03129
    Figure US20090189522A1-20090730-C03130
    Figure US20090189522A1-20090730-C03131
    Figure US20090189522A1-20090730-C03132
    D-709
    Figure US20090189522A1-20090730-C03133
    Figure US20090189522A1-20090730-C03134
    D-710
    Figure US20090189522A1-20090730-C03135
    Figure US20090189522A1-20090730-C03136
    D-711
    Figure US20090189522A1-20090730-C03137
    Figure US20090189522A1-20090730-C03138
    D-712
    Figure US20090189522A1-20090730-C03139
    Figure US20090189522A1-20090730-C03140
    D-713
    Figure US20090189522A1-20090730-C03141
    Figure US20090189522A1-20090730-C03142
    D-714
    Figure US20090189522A1-20090730-C03143
    Figure US20090189522A1-20090730-C03144
    D-715
    Figure US20090189522A1-20090730-C03145
    Figure US20090189522A1-20090730-C03146
    D-716
    Figure US20090189522A1-20090730-C03147
    Figure US20090189522A1-20090730-C03148
    D-717
    Figure US20090189522A1-20090730-C03149
    Figure US20090189522A1-20090730-C03150
    D-718
    Figure US20090189522A1-20090730-C03151
    Figure US20090189522A1-20090730-C03152
    D-719
    Figure US20090189522A1-20090730-C03153
    Figure US20090189522A1-20090730-C03154
    D-720
    Figure US20090189522A1-20090730-C03155
    Figure US20090189522A1-20090730-C03156
  • TABLE 61
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03157
    Figure US20090189522A1-20090730-C03158
    D-721 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03159
    Figure US20090189522A1-20090730-C03160
    D-722 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03161
    Figure US20090189522A1-20090730-C03162
    D-723 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03163
    Figure US20090189522A1-20090730-C03164
    D-724 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03165
    Figure US20090189522A1-20090730-C03166
    D-725 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03167
    Figure US20090189522A1-20090730-C03168
    D-726 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03169
    Figure US20090189522A1-20090730-C03170
    D-727 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03171
    Figure US20090189522A1-20090730-C03172
    D-728 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03173
    Figure US20090189522A1-20090730-C03174
    D-729 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03175
    Figure US20090189522A1-20090730-C03176
    D-730 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03177
    Figure US20090189522A1-20090730-C03178
    D-731 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03179
    Figure US20090189522A1-20090730-C03180
    D-732 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03181
    Figure US20090189522A1-20090730-C03182
    Figure US20090189522A1-20090730-C03183
    Figure US20090189522A1-20090730-C03184
    D-721
    Figure US20090189522A1-20090730-C03185
    Figure US20090189522A1-20090730-C03186
    D-722
    Figure US20090189522A1-20090730-C03187
    Figure US20090189522A1-20090730-C03188
    D-723
    Figure US20090189522A1-20090730-C03189
    Figure US20090189522A1-20090730-C03190
    D-724
    Figure US20090189522A1-20090730-C03191
    Figure US20090189522A1-20090730-C03192
    D-725
    Figure US20090189522A1-20090730-C03193
    Figure US20090189522A1-20090730-C03194
    D-726
    Figure US20090189522A1-20090730-C03195
    Figure US20090189522A1-20090730-C03196
    D-727
    Figure US20090189522A1-20090730-C03197
    Figure US20090189522A1-20090730-C03198
    D-728
    Figure US20090189522A1-20090730-C03199
    Figure US20090189522A1-20090730-C03200
    D-729
    Figure US20090189522A1-20090730-C03201
    Figure US20090189522A1-20090730-C03202
    D-730
    Figure US20090189522A1-20090730-C03203
    Figure US20090189522A1-20090730-C03204
    D-731
    Figure US20090189522A1-20090730-C03205
    Figure US20090189522A1-20090730-C03206
    D-732
    Figure US20090189522A1-20090730-C03207
    Figure US20090189522A1-20090730-C03208
  • TABLE 62
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03209
    Figure US20090189522A1-20090730-C03210
    D-733 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03211
    Figure US20090189522A1-20090730-C03212
    D-734 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03213
    Figure US20090189522A1-20090730-C03214
    D-735 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03215
    Figure US20090189522A1-20090730-C03216
    D-736 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03217
    Figure US20090189522A1-20090730-C03218
    D-737 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03219
    Figure US20090189522A1-20090730-C03220
    D-738 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03221
    Figure US20090189522A1-20090730-C03222
    D-739 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03223
    Figure US20090189522A1-20090730-C03224
    D-740 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03225
    Figure US20090189522A1-20090730-C03226
    D-741 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03227
    Figure US20090189522A1-20090730-C03228
    D-742 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03229
    Figure US20090189522A1-20090730-C03230
    D-743 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03231
    Figure US20090189522A1-20090730-C03232
    D-744 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03233
    Figure US20090189522A1-20090730-C03234
    Figure US20090189522A1-20090730-C03235
    Figure US20090189522A1-20090730-C03236
    D-733
    Figure US20090189522A1-20090730-C03237
    Figure US20090189522A1-20090730-C03238
    D-734
    Figure US20090189522A1-20090730-C03239
    Figure US20090189522A1-20090730-C03240
    D-735
    Figure US20090189522A1-20090730-C03241
    Figure US20090189522A1-20090730-C03242
    D-736
    Figure US20090189522A1-20090730-C03243
    Figure US20090189522A1-20090730-C03244
    D-737
    Figure US20090189522A1-20090730-C03245
    Figure US20090189522A1-20090730-C03246
    D-738
    Figure US20090189522A1-20090730-C03247
    Figure US20090189522A1-20090730-C03248
    D-739
    Figure US20090189522A1-20090730-C03249
    Figure US20090189522A1-20090730-C03250
    D-740
    Figure US20090189522A1-20090730-C03251
    Figure US20090189522A1-20090730-C03252
    D-741
    Figure US20090189522A1-20090730-C03253
    Figure US20090189522A1-20090730-C03254
    D-742
    Figure US20090189522A1-20090730-C03255
    Figure US20090189522A1-20090730-C03256
    D-743
    Figure US20090189522A1-20090730-C03257
    Figure US20090189522A1-20090730-C03258
    D-744
    Figure US20090189522A1-20090730-C03259
    Figure US20090189522A1-20090730-C03260
  • TABLE 63
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03261
    Figure US20090189522A1-20090730-C03262
    D-745 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03263
    Figure US20090189522A1-20090730-C03264
    D-746 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03265
    Figure US20090189522A1-20090730-C03266
    D-747 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03267
    Figure US20090189522A1-20090730-C03268
    D-748 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03269
    Figure US20090189522A1-20090730-C03270
    D-749 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03271
    Figure US20090189522A1-20090730-C03272
    D-750 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03273
    Figure US20090189522A1-20090730-C03274
    D-751 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03275
    Figure US20090189522A1-20090730-C03276
    D-752 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03277
    Figure US20090189522A1-20090730-C03278
    D-753 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03279
    Figure US20090189522A1-20090730-C03280
    D-754 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03281
    Figure US20090189522A1-20090730-C03282
    D-755 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03283
    Figure US20090189522A1-20090730-C03284
    D-756 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03285
    Figure US20090189522A1-20090730-C03286
    Figure US20090189522A1-20090730-C03287
    Figure US20090189522A1-20090730-C03288
    D-745
    Figure US20090189522A1-20090730-C03289
    Figure US20090189522A1-20090730-C03290
    D-746
    Figure US20090189522A1-20090730-C03291
    Figure US20090189522A1-20090730-C03292
    D-747
    Figure US20090189522A1-20090730-C03293
    Figure US20090189522A1-20090730-C03294
    D-748
    Figure US20090189522A1-20090730-C03295
    Figure US20090189522A1-20090730-C03296
    D-749
    Figure US20090189522A1-20090730-C03297
    Figure US20090189522A1-20090730-C03298
    D-750
    Figure US20090189522A1-20090730-C03299
    Figure US20090189522A1-20090730-C03300
    D-751
    Figure US20090189522A1-20090730-C03301
    Figure US20090189522A1-20090730-C03302
    D-752
    Figure US20090189522A1-20090730-C03303
    Figure US20090189522A1-20090730-C03304
    D-753
    Figure US20090189522A1-20090730-C03305
    Figure US20090189522A1-20090730-C03306
    D-754
    Figure US20090189522A1-20090730-C03307
    Figure US20090189522A1-20090730-C03308
    D-755
    Figure US20090189522A1-20090730-C03309
    Figure US20090189522A1-20090730-C03310
    D-756
    Figure US20090189522A1-20090730-C03311
    Figure US20090189522A1-20090730-C03312
  • TABLE 64
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C03313
    Figure US20090189522A1-20090730-C03314
    D-757 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03315
    Figure US20090189522A1-20090730-C03316
    D-758 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03317
    Figure US20090189522A1-20090730-C03318
    D-759 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03319
    Figure US20090189522A1-20090730-C03320
    D-760 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03321
    Figure US20090189522A1-20090730-C03322
    D-761 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03323
    Figure US20090189522A1-20090730-C03324
    D-762 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03325
    Figure US20090189522A1-20090730-C03326
    D-763 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03327
    Figure US20090189522A1-20090730-C03328
    D-764 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03329
    Figure US20090189522A1-20090730-C03330
    D-765 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03331
    Figure US20090189522A1-20090730-C03332
    D-766 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03333
    Figure US20090189522A1-20090730-C03334
    D-767 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03335
    Figure US20090189522A1-20090730-C03336
    D-768 H Isopropyl H Isopropyl
    Figure US20090189522A1-20090730-C03337
    Figure US20090189522A1-20090730-C03338
    Figure US20090189522A1-20090730-C03339
    Figure US20090189522A1-20090730-C03340
    D-757
    Figure US20090189522A1-20090730-C03341
    Figure US20090189522A1-20090730-C03342
    D-758
    Figure US20090189522A1-20090730-C03343
    Figure US20090189522A1-20090730-C03344
    D-759
    Figure US20090189522A1-20090730-C03345
    Figure US20090189522A1-20090730-C03346
    D-760
    Figure US20090189522A1-20090730-C03347
    Figure US20090189522A1-20090730-C03348
    D-761
    Figure US20090189522A1-20090730-C03349
    Figure US20090189522A1-20090730-C03350
    D-762
    Figure US20090189522A1-20090730-C03351
    Figure US20090189522A1-20090730-C03352
    D-763
    Figure US20090189522A1-20090730-C03353
    Figure US20090189522A1-20090730-C03354
    D-764
    Figure US20090189522A1-20090730-C03355
    Figure US20090189522A1-20090730-C03356
    D-765
    Figure US20090189522A1-20090730-C03357
    Figure US20090189522A1-20090730-C03358
    D-766
    Figure US20090189522A1-20090730-C03359
    Figure US20090189522A1-20090730-C03360
    D-767
    Figure US20090189522A1-20090730-C03361
    Figure US20090189522A1-20090730-C03362
    D-768
    Figure US20090189522A1-20090730-C03363
    Figure US20090189522A1-20090730-C03364
  • TABLE 65
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03365
    Figure US20090189522A1-20090730-C03366
    Figure US20090189522A1-20090730-C03367
    Figure US20090189522A1-20090730-C03368
    D-769 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03369
    Figure US20090189522A1-20090730-C03370
    Figure US20090189522A1-20090730-C03371
    Figure US20090189522A1-20090730-C03372
    D-770 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03373
    Figure US20090189522A1-20090730-C03374
    Figure US20090189522A1-20090730-C03375
    Figure US20090189522A1-20090730-C03376
    D-771 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03377
    Figure US20090189522A1-20090730-C03378
    Figure US20090189522A1-20090730-C03379
    Figure US20090189522A1-20090730-C03380
    D-772 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03381
    Figure US20090189522A1-20090730-C03382
    Figure US20090189522A1-20090730-C03383
    Figure US20090189522A1-20090730-C03384
    D-773 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03385
    Figure US20090189522A1-20090730-C03386
    Figure US20090189522A1-20090730-C03387
    Figure US20090189522A1-20090730-C03388
    D-774 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03389
    Figure US20090189522A1-20090730-C03390
    Figure US20090189522A1-20090730-C03391
    Figure US20090189522A1-20090730-C03392
    D-775 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03393
    Figure US20090189522A1-20090730-C03394
    Figure US20090189522A1-20090730-C03395
    Figure US20090189522A1-20090730-C03396
    D-776 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03397
    Figure US20090189522A1-20090730-C03398
    Figure US20090189522A1-20090730-C03399
    Figure US20090189522A1-20090730-C03400
    D-777 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03401
    Figure US20090189522A1-20090730-C03402
    Figure US20090189522A1-20090730-C03403
    Figure US20090189522A1-20090730-C03404
    D-778 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03405
    Figure US20090189522A1-20090730-C03406
    Figure US20090189522A1-20090730-C03407
    Figure US20090189522A1-20090730-C03408
    D-779 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03409
    Figure US20090189522A1-20090730-C03410
    Figure US20090189522A1-20090730-C03411
    Figure US20090189522A1-20090730-C03412
    D-780 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03413
    Figure US20090189522A1-20090730-C03414
    Figure US20090189522A1-20090730-C03415
    Figure US20090189522A1-20090730-C03416
  • TABLE 66
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03417
    Figure US20090189522A1-20090730-C03418
    Figure US20090189522A1-20090730-C03419
    Figure US20090189522A1-20090730-C03420
    D-781 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03421
    Figure US20090189522A1-20090730-C03422
    Figure US20090189522A1-20090730-C03423
    Figure US20090189522A1-20090730-C03424
    D-782 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03425
    Figure US20090189522A1-20090730-C03426
    Figure US20090189522A1-20090730-C03427
    Figure US20090189522A1-20090730-C03428
    D-783 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03429
    Figure US20090189522A1-20090730-C03430
    Figure US20090189522A1-20090730-C03431
    Figure US20090189522A1-20090730-C03432
    D-784 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03433
    Figure US20090189522A1-20090730-C03434
    Figure US20090189522A1-20090730-C03435
    Figure US20090189522A1-20090730-C03436
    D-785 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03437
    Figure US20090189522A1-20090730-C03438
    Figure US20090189522A1-20090730-C03439
    Figure US20090189522A1-20090730-C03440
    D-786 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03441
    Figure US20090189522A1-20090730-C03442
    Figure US20090189522A1-20090730-C03443
    Figure US20090189522A1-20090730-C03444
    D-787 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03445
    Figure US20090189522A1-20090730-C03446
    Figure US20090189522A1-20090730-C03447
    Figure US20090189522A1-20090730-C03448
    D-788 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03449
    Figure US20090189522A1-20090730-C03450
    Figure US20090189522A1-20090730-C03451
    Figure US20090189522A1-20090730-C03452
    D-789 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03453
    Figure US20090189522A1-20090730-C03454
    Figure US20090189522A1-20090730-C03455
    Figure US20090189522A1-20090730-C03456
    D-790 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03457
    Figure US20090189522A1-20090730-C03458
    Figure US20090189522A1-20090730-C03459
    Figure US20090189522A1-20090730-C03460
    D-791 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03461
    Figure US20090189522A1-20090730-C03462
    Figure US20090189522A1-20090730-C03463
    Figure US20090189522A1-20090730-C03464
    D-792 Cyclohexyl H H H
    Figure US20090189522A1-20090730-C03465
    Figure US20090189522A1-20090730-C03466
    Figure US20090189522A1-20090730-C03467
    Figure US20090189522A1-20090730-C03468
  • TABLE 67
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03469
    Figure US20090189522A1-20090730-C03470
    Figure US20090189522A1-20090730-C03471
    Figure US20090189522A1-20090730-C03472
    D-793 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03473
    Figure US20090189522A1-20090730-C03474
    Figure US20090189522A1-20090730-C03475
    Figure US20090189522A1-20090730-C03476
    D-794 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03477
    Figure US20090189522A1-20090730-C03478
    Figure US20090189522A1-20090730-C03479
    Figure US20090189522A1-20090730-C03480
    D-795 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03481
    Figure US20090189522A1-20090730-C03482
    Figure US20090189522A1-20090730-C03483
    Figure US20090189522A1-20090730-C03484
    D-796 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03485
    Figure US20090189522A1-20090730-C03486
    Figure US20090189522A1-20090730-C03487
    Figure US20090189522A1-20090730-C03488
    D-797 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03489
    Figure US20090189522A1-20090730-C03490
    Figure US20090189522A1-20090730-C03491
    Figure US20090189522A1-20090730-C03492
    D-798 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03493
    Figure US20090189522A1-20090730-C03494
    Figure US20090189522A1-20090730-C03495
    Figure US20090189522A1-20090730-C03496
    D-799 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03497
    Figure US20090189522A1-20090730-C03498
    Figure US20090189522A1-20090730-C03499
    Figure US20090189522A1-20090730-C03500
    D-800 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03501
    Figure US20090189522A1-20090730-C03502
    Figure US20090189522A1-20090730-C03503
    Figure US20090189522A1-20090730-C03504
    D-801 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03505
    Figure US20090189522A1-20090730-C03506
    Figure US20090189522A1-20090730-C03507
    Figure US20090189522A1-20090730-C03508
    D-802 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03509
    Figure US20090189522A1-20090730-C03510
    Figure US20090189522A1-20090730-C03511
    Figure US20090189522A1-20090730-C03512
    D-803 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03513
    Figure US20090189522A1-20090730-C03514
    Figure US20090189522A1-20090730-C03515
    Figure US20090189522A1-20090730-C03516
    D-804 Cyctohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03517
    Figure US20090189522A1-20090730-C03518
    Figure US20090189522A1-20090730-C03519
    Figure US20090189522A1-20090730-C03520
  • TABLE 68
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03521
    Figure US20090189522A1-20090730-C03522
    Figure US20090189522A1-20090730-C03523
    Figure US20090189522A1-20090730-C03524
    D-805 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03525
    Figure US20090189522A1-20090730-C03526
    Figure US20090189522A1-20090730-C03527
    Figure US20090189522A1-20090730-C03528
    D-806 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03529
    Figure US20090189522A1-20090730-C03530
    Figure US20090189522A1-20090730-C03531
    Figure US20090189522A1-20090730-C03532
    D-807 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03533
    Figure US20090189522A1-20090730-C03534
    Figure US20090189522A1-20090730-C03535
    Figure US20090189522A1-20090730-C03536
    D-808 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03537
    Figure US20090189522A1-20090730-C03538
    Figure US20090189522A1-20090730-C03539
    Figure US20090189522A1-20090730-C03540
    D-809 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03541
    Figure US20090189522A1-20090730-C03542
    Figure US20090189522A1-20090730-C03543
    Figure US20090189522A1-20090730-C03544
    D-810 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03545
    Figure US20090189522A1-20090730-C03546
    Figure US20090189522A1-20090730-C03547
    Figure US20090189522A1-20090730-C03548
    D-811 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03549
    Figure US20090189522A1-20090730-C03550
    Figure US20090189522A1-20090730-C03551
    Figure US20090189522A1-20090730-C03552
    D-812 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03553
    Figure US20090189522A1-20090730-C03554
    Figure US20090189522A1-20090730-C03555
    Figure US20090189522A1-20090730-C03556
    D-813 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03557
    Figure US20090189522A1-20090730-C03558
    Figure US20090189522A1-20090730-C03559
    Figure US20090189522A1-20090730-C03560
    D-814 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03561
    Figure US20090189522A1-20090730-C03562
    Figure US20090189522A1-20090730-C03563
    Figure US20090189522A1-20090730-C03564
    D-815 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03565
    Figure US20090189522A1-20090730-C03566
    Figure US20090189522A1-20090730-C03567
    Figure US20090189522A1-20090730-C03568
    D-816 Cyclohexyl H Cyclohexyl H
    Figure US20090189522A1-20090730-C03569
    Figure US20090189522A1-20090730-C03570
    Figure US20090189522A1-20090730-C03571
    Figure US20090189522A1-20090730-C03572
  • TABLE 69
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03573
    Figure US20090189522A1-20090730-C03574
    Figure US20090189522A1-20090730-C03575
    Figure US20090189522A1-20090730-C03576
    D-817 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03577
    Figure US20090189522A1-20090730-C03578
    Figure US20090189522A1-20090730-C03579
    Figure US20090189522A1-20090730-C03580
    D-818 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03581
    Figure US20090189522A1-20090730-C03582
    Figure US20090189522A1-20090730-C03583
    Figure US20090189522A1-20090730-C03584
    D-819 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03585
    Figure US20090189522A1-20090730-C03586
    Figure US20090189522A1-20090730-C03587
    Figure US20090189522A1-20090730-C03588
    D-820 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03589
    Figure US20090189522A1-20090730-C03590
    Figure US20090189522A1-20090730-C03591
    Figure US20090189522A1-20090730-C03592
    D-821 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03593
    Figure US20090189522A1-20090730-C03594
    Figure US20090189522A1-20090730-C03595
    Figure US20090189522A1-20090730-C03596
    D-822 4-t- butylphernyl H H H
    Figure US20090189522A1-20090730-C03597
    Figure US20090189522A1-20090730-C03598
    Figure US20090189522A1-20090730-C03599
    Figure US20090189522A1-20090730-C03600
    D-823 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03601
    Figure US20090189522A1-20090730-C03602
    Figure US20090189522A1-20090730-C03603
    Figure US20090189522A1-20090730-C03604
    D-824 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03605
    Figure US20090189522A1-20090730-C03606
    Figure US20090189522A1-20090730-C03607
    Figure US20090189522A1-20090730-C03608
    D-825 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03609
    Figure US20090189522A1-20090730-C03610
    Figure US20090189522A1-20090730-C03611
    Figure US20090189522A1-20090730-C03612
    D-826 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03613
    Figure US20090189522A1-20090730-C03614
    Figure US20090189522A1-20090730-C03615
    Figure US20090189522A1-20090730-C03616
    D-827 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03617
    Figure US20090189522A1-20090730-C03618
    Figure US20090189522A1-20090730-C03619
    Figure US20090189522A1-20090730-C03620
    D-828 4- trimethyl silylphenyl H H H
    Figure US20090189522A1-20090730-C03621
    Figure US20090189522A1-20090730-C03622
    Figure US20090189522A1-20090730-C03623
    Figure US20090189522A1-20090730-C03624
  • TABLE 70
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03625
    Figure US20090189522A1-20090730-C03626
    Figure US20090189522A1-20090730-C03627
    Figure US20090189522A1-20090730-C03628
    D-829 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03629
    Figure US20090189522A1-20090730-C03630
    Figure US20090189522A1-20090730-C03631
    Figure US20090189522A1-20090730-C03632
    D-830 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03633
    Figure US20090189522A1-20090730-C03634
    Figure US20090189522A1-20090730-C03635
    Figure US20090189522A1-20090730-C03636
    D-831 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03637
    Figure US20090189522A1-20090730-C03638
    Figure US20090189522A1-20090730-C03639
    Figure US20090189522A1-20090730-C03640
    D-832 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03641
    Figure US20090189522A1-20090730-C03642
    Figure US20090189522A1-20090730-C03643
    Figure US20090189522A1-20090730-C03644
    D-833 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03645
    Figure US20090189522A1-20090730-C03646
    Figure US20090189522A1-20090730-C03647
    Figure US20090189522A1-20090730-C03648
    D-834 4-cyano phenyl H H H
    Figure US20090189522A1-20090730-C03649
    Figure US20090189522A1-20090730-C03650
    Figure US20090189522A1-20090730-C03651
    Figure US20090189522A1-20090730-C03652
    D-835 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03653
    Figure US20090189522A1-20090730-C03654
    Figure US20090189522A1-20090730-C03655
    Figure US20090189522A1-20090730-C03656
    D-836 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03657
    Figure US20090189522A1-20090730-C03658
    Figure US20090189522A1-20090730-C03659
    Figure US20090189522A1-20090730-C03660
    D-837 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03661
    Figure US20090189522A1-20090730-C03662
    Figure US20090189522A1-20090730-C03663
    Figure US20090189522A1-20090730-C03664
    D-838 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03665
    Figure US20090189522A1-20090730-C03666
    Figure US20090189522A1-20090730-C03667
    Figure US20090189522A1-20090730-C03668
    D-839 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03669
    Figure US20090189522A1-20090730-C03670
    Figure US20090189522A1-20090730-C03671
    Figure US20090189522A1-20090730-C03672
    D-840 4-trifluoro methylphenyl H H H
    Figure US20090189522A1-20090730-C03673
    Figure US20090189522A1-20090730-C03674
    Figure US20090189522A1-20090730-C03675
    Figure US20090189522A1-20090730-C03676
  • TABLE 71
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03677
    Figure US20090189522A1-20090730-C03678
    Figure US20090189522A1-20090730-C03679
    Figure US20090189522A1-20090730-C03680
    D-841 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03681
    Figure US20090189522A1-20090730-C03682
    Figure US20090189522A1-20090730-C03683
    Figure US20090189522A1-20090730-C03684
    D-842 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03685
    Figure US20090189522A1-20090730-C03686
    Figure US20090189522A1-20090730-C03687
    Figure US20090189522A1-20090730-C03688
    D-843 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03689
    Figure US20090189522A1-20090730-C03690
    Figure US20090189522A1-20090730-C03691
    Figure US20090189522A1-20090730-C03692
    D-844 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03693
    Figure US20090189522A1-20090730-C03694
    Figure US20090189522A1-20090730-C03695
    Figure US20090189522A1-20090730-C03696
    D-845 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03697
    Figure US20090189522A1-20090730-C03698
    Figure US20090189522A1-20090730-C03699
    Figure US20090189522A1-20090730-C03700
    D-846 2-quinolyl H H H
    Figure US20090189522A1-20090730-C03701
    Figure US20090189522A1-20090730-C03702
    Figure US20090189522A1-20090730-C03703
    Figure US20090189522A1-20090730-C03704
    D-847 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03705
    Figure US20090189522A1-20090730-C03706
    Figure US20090189522A1-20090730-C03707
    Figure US20090189522A1-20090730-C03708
    D-848 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03709
    Figure US20090189522A1-20090730-C03710
    Figure US20090189522A1-20090730-C03711
    Figure US20090189522A1-20090730-C03712
    D-849 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03713
    Figure US20090189522A1-20090730-C03714
    Figure US20090189522A1-20090730-C03715
    Figure US20090189522A1-20090730-C03716
    D-850 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03717
    Figure US20090189522A1-20090730-C03718
    Figure US20090189522A1-20090730-C03719
    Figure US20090189522A1-20090730-C03720
    D-851 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03721
    Figure US20090189522A1-20090730-C03722
    Figure US20090189522A1-20090730-C03723
    Figure US20090189522A1-20090730-C03724
    D-852 3-iso quinolyl H H H
    Figure US20090189522A1-20090730-C03725
    Figure US20090189522A1-20090730-C03726
    Figure US20090189522A1-20090730-C03727
    Figure US20090189522A1-20090730-C03728
  • TABLE 72
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03729
    Figure US20090189522A1-20090730-C03730
    Figure US20090189522A1-20090730-C03731
    Figure US20090189522A1-20090730-C03732
    D-853 1- adamanthyl H H H
    Figure US20090189522A1-20090730-C03733
    Figure US20090189522A1-20090730-C03734
    Figure US20090189522A1-20090730-C03735
    Figure US20090189522A1-20090730-C03736
    D-854 1- adamanthyl H H H
    Figure US20090189522A1-20090730-C03737
    Figure US20090189522A1-20090730-C03738
    Figure US20090189522A1-20090730-C03739
    Figure US20090189522A1-20090730-C03740
    D-855 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03741
    Figure US20090189522A1-20090730-C03742
    Figure US20090189522A1-20090730-C03743
    Figure US20090189522A1-20090730-C03744
    D-856 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03745
    Figure US20090189522A1-20090730-C03746
    Figure US20090189522A1-20090730-C03747
    Figure US20090189522A1-20090730-C03748
    D-857 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03749
    Figure US20090189522A1-20090730-C03750
    Figure US20090189522A1-20090730-C03751
    Figure US20090189522A1-20090730-C03752
    D-858 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03753
    Figure US20090189522A1-20090730-C03754
    Figure US20090189522A1-20090730-C03755
    Figure US20090189522A1-20090730-C03756
    D-859 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03757
    Figure US20090189522A1-20090730-C03758
    Figure US20090189522A1-20090730-C03759
    Figure US20090189522A1-20090730-C03760
    D-860 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03761
    Figure US20090189522A1-20090730-C03762
    Figure US20090189522A1-20090730-C03763
    Figure US20090189522A1-20090730-C03764
    D-861 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03765
    Figure US20090189522A1-20090730-C03766
    Figure US20090189522A1-20090730-C03767
    Figure US20090189522A1-20090730-C03768
    D-862 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03769
    Figure US20090189522A1-20090730-C03770
    Figure US20090189522A1-20090730-C03771
    Figure US20090189522A1-20090730-C03772
    D-863 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03773
    Figure US20090189522A1-20090730-C03774
    Figure US20090189522A1-20090730-C03775
    Figure US20090189522A1-20090730-C03776
    D-864 1- pyrenyl H H H
    Figure US20090189522A1-20090730-C03777
    Figure US20090189522A1-20090730-C03778
    Figure US20090189522A1-20090730-C03779
    Figure US20090189522A1-20090730-C03780
  • TABLE 73
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03781
    Figure US20090189522A1-20090730-C03782
    Figure US20090189522A1-20090730-C03783
    Figure US20090189522A1-20090730-C03784
    D-865 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03785
    Figure US20090189522A1-20090730-C03786
    Figure US20090189522A1-20090730-C03787
    Figure US20090189522A1-20090730-C03788
    D-866 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03789
    Figure US20090189522A1-20090730-C03790
    Figure US20090189522A1-20090730-C03791
    Figure US20090189522A1-20090730-C03792
    D-867 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03793
    Figure US20090189522A1-20090730-C03794
    Figure US20090189522A1-20090730-C03795
    Figure US20090189522A1-20090730-C03796
    D-868 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03797
    Figure US20090189522A1-20090730-C03798
    Figure US20090189522A1-20090730-C03799
    Figure US20090189522A1-20090730-C03800
    D-869 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03801
    Figure US20090189522A1-20090730-C03802
    Figure US20090189522A1-20090730-C03803
    Figure US20090189522A1-20090730-C03804
    D-870 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03805
    Figure US20090189522A1-20090730-C03806
    Figure US20090189522A1-20090730-C03807
    Figure US20090189522A1-20090730-C03808
    D-871 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03809
    Figure US20090189522A1-20090730-C03810
    Figure US20090189522A1-20090730-C03811
    Figure US20090189522A1-20090730-C03812
    D-872 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03813
    Figure US20090189522A1-20090730-C03814
    Figure US20090189522A1-20090730-C03815
    Figure US20090189522A1-20090730-C03816
    D-873 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03817
    Figure US20090189522A1-20090730-C03818
    Figure US20090189522A1-20090730-C03819
    Figure US20090189522A1-20090730-C03820
    D-874 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03821
    Figure US20090189522A1-20090730-C03822
    Figure US20090189522A1-20090730-C03823
    Figure US20090189522A1-20090730-C03824
    D-875 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03825
    Figure US20090189522A1-20090730-C03826
    Figure US20090189522A1-20090730-C03827
    Figure US20090189522A1-20090730-C03828
    D-876 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03829
    Figure US20090189522A1-20090730-C03830
    Figure US20090189522A1-20090730-C03831
    Figure US20090189522A1-20090730-C03832
  • TABLE 74
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03833
    Figure US20090189522A1-20090730-C03834
    Figure US20090189522A1-20090730-C03835
    Figure US20090189522A1-20090730-C03836
    D-877 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03837
    Figure US20090189522A1-20090730-C03838
    Figure US20090189522A1-20090730-C03839
    Figure US20090189522A1-20090730-C03840
    D-878 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03841
    Figure US20090189522A1-20090730-C03842
    Figure US20090189522A1-20090730-C03843
    Figure US20090189522A1-20090730-C03844
    D-879 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03845
    Figure US20090189522A1-20090730-C03846
    Figure US20090189522A1-20090730-C03847
    Figure US20090189522A1-20090730-C03848
    D-880 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03849
    Figure US20090189522A1-20090730-C03850
    Figure US20090189522A1-20090730-C03851
    Figure US20090189522A1-20090730-C03852
    D-881 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03853
    Figure US20090189522A1-20090730-C03854
    Figure US20090189522A1-20090730-C03855
    Figure US20090189522A1-20090730-C03856
    D-882 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03857
    Figure US20090189522A1-20090730-C03858
    Figure US20090189522A1-20090730-C03859
    Figure US20090189522A1-20090730-C03860
    D-883 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03861
    Figure US20090189522A1-20090730-C03862
    Figure US20090189522A1-20090730-C03863
    Figure US20090189522A1-20090730-C03864
    D-884 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03865
    Figure US20090189522A1-20090730-C03866
    Figure US20090189522A1-20090730-C03867
    Figure US20090189522A1-20090730-C03868
    D-885 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03869
    Figure US20090189522A1-20090730-C03870
    Figure US20090189522A1-20090730-C03871
    Figure US20090189522A1-20090730-C03872
    D-886 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03873
    Figure US20090189522A1-20090730-C03874
    Figure US20090189522A1-20090730-C03875
    Figure US20090189522A1-20090730-C03876
    D-887 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03877
    Figure US20090189522A1-20090730-C03878
    Figure US20090189522A1-20090730-C03879
    Figure US20090189522A1-20090730-C03880
    D-888 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03881
    Figure US20090189522A1-20090730-C03882
    Figure US20090189522A1-20090730-C03883
    Figure US20090189522A1-20090730-C03884
  • TABLE 75
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03885
    Figure US20090189522A1-20090730-C03886
    Figure US20090189522A1-20090730-C03887
    Figure US20090189522A1-20090730-C03888
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03889
    Figure US20090189522A1-20090730-C03890
    Figure US20090189522A1-20090730-C03891
    Figure US20090189522A1-20090730-C03892
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03893
    Figure US20090189522A1-20090730-C03894
    Figure US20090189522A1-20090730-C03895
    Figure US20090189522A1-20090730-C03896
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03897
    Figure US20090189522A1-20090730-C03898
    Figure US20090189522A1-20090730-C03899
    Figure US20090189522A1-20090730-C03900
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03901
    Figure US20090189522A1-20090730-C03902
    Figure US20090189522A1-20090730-C03903
    Figure US20090189522A1-20090730-C03904
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03905
    Figure US20090189522A1-20090730-C03906
    Figure US20090189522A1-20090730-C03907
    Figure US20090189522A1-20090730-C03908
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03909
    Figure US20090189522A1-20090730-C03910
    Figure US20090189522A1-20090730-C03911
    Figure US20090189522A1-20090730-C03912
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03913
    Figure US20090189522A1-20090730-C03914
    Figure US20090189522A1-20090730-C03915
    Figure US20090189522A1-20090730-C03916
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03917
    Figure US20090189522A1-20090730-C03918
    Figure US20090189522A1-20090730-C03919
    Figure US20090189522A1-20090730-C03920
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03921
    Figure US20090189522A1-20090730-C03922
    Figure US20090189522A1-20090730-C03923
    Figure US20090189522A1-20090730-C03924
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03925
    Figure US20090189522A1-20090730-C03926
    Figure US20090189522A1-20090730-C03927
    Figure US20090189522A1-20090730-C03928
    H Cyolohexyl H H
    Figure US20090189522A1-20090730-C03929
    Figure US20090189522A1-20090730-C03930
    Figure US20090189522A1-20090730-C03931
    Figure US20090189522A1-20090730-C03932
    H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03933
    Figure US20090189522A1-20090730-C03934
    Figure US20090189522A1-20090730-C03935
    Figure US20090189522A1-20090730-C03936
  • TABLE 76
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03937
    Figure US20090189522A1-20090730-C03938
    Figure US20090189522A1-20090730-C03939
    Figure US20090189522A1-20090730-C03940
    D-901 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03941
    Figure US20090189522A1-20090730-C03942
    Figure US20090189522A1-20090730-C03943
    Figure US20090189522A1-20090730-C03944
    D-902 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03945
    Figure US20090189522A1-20090730-C03946
    Figure US20090189522A1-20090730-C03947
    Figure US20090189522A1-20090730-C03948
    D-903 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03949
    Figure US20090189522A1-20090730-C03950
    Figure US20090189522A1-20090730-C03951
    Figure US20090189522A1-20090730-C03952
    D-904 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03953
    Figure US20090189522A1-20090730-C03954
    Figure US20090189522A1-20090730-C03955
    Figure US20090189522A1-20090730-C03956
    D-905 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03957
    Figure US20090189522A1-20090730-C03958
    Figure US20090189522A1-20090730-C03959
    Figure US20090189522A1-20090730-C03960
    D-906 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03961
    Figure US20090189522A1-20090730-C03962
    Figure US20090189522A1-20090730-C03963
    Figure US20090189522A1-20090730-C03964
    D-907 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03965
    Figure US20090189522A1-20090730-C03966
    Figure US20090189522A1-20090730-C03967
    Figure US20090189522A1-20090730-C03968
    D-908 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03969
    Figure US20090189522A1-20090730-C03970
    Figure US20090189522A1-20090730-C03971
    Figure US20090189522A1-20090730-C03972
    D-909 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03973
    Figure US20090189522A1-20090730-C03974
    Figure US20090189522A1-20090730-C03975
    Figure US20090189522A1-20090730-C03976
    D-910 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03977
    Figure US20090189522A1-20090730-C03978
    Figure US20090189522A1-20090730-C03979
    Figure US20090189522A1-20090730-C03980
    D-911 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03981
    Figure US20090189522A1-20090730-C03982
    Figure US20090189522A1-20090730-C03983
    Figure US20090189522A1-20090730-C03984
    D-912 H Cyclohexyl H H
    Figure US20090189522A1-20090730-C03985
    Figure US20090189522A1-20090730-C03986
    Figure US20090189522A1-20090730-C03987
    Figure US20090189522A1-20090730-C03988
  • TABLE 77
    R1 R2 R3 R4
    Figure US20090189522A1-20090730-C03989
    Figure US20090189522A1-20090730-C03990
    Figure US20090189522A1-20090730-C03991
    Figure US20090189522A1-20090730-C03992
    D-913 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C03993
    Figure US20090189522A1-20090730-C03994
    Figure US20090189522A1-20090730-C03995
    Figure US20090189522A1-20090730-C03996
    D-914 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C03997
    Figure US20090189522A1-20090730-C03998
    Figure US20090189522A1-20090730-C03999
    Figure US20090189522A1-20090730-C04000
    D-915 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04001
    Figure US20090189522A1-20090730-C04002
    Figure US20090189522A1-20090730-C04003
    Figure US20090189522A1-20090730-C04004
    D-916 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04005
    Figure US20090189522A1-20090730-C04006
    Figure US20090189522A1-20090730-C04007
    Figure US20090189522A1-20090730-C04008
    D-917 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04009
    Figure US20090189522A1-20090730-C04010
    Figure US20090189522A1-20090730-C04011
    Figure US20090189522A1-20090730-C04012
    D-918 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04013
    Figure US20090189522A1-20090730-C04014
    Figure US20090189522A1-20090730-C04015
    Figure US20090189522A1-20090730-C04016
    D-919 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04017
    Figure US20090189522A1-20090730-C04018
    Figure US20090189522A1-20090730-C04019
    Figure US20090189522A1-20090730-C04020
    D-920 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04021
    Figure US20090189522A1-20090730-C04022
    Figure US20090189522A1-20090730-C04023
    Figure US20090189522A1-20090730-C04024
    D-921 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04025
    Figure US20090189522A1-20090730-C04026
    Figure US20090189522A1-20090730-C04027
    Figure US20090189522A1-20090730-C04028
    D-922 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04029
    Figure US20090189522A1-20090730-C04030
    Figure US20090189522A1-20090730-C04031
    Figure US20090189522A1-20090730-C04032
    D-923 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04033
    Figure US20090189522A1-20090730-C04034
    Figure US20090189522A1-20090730-C04035
    Figure US20090189522A1-20090730-C04036
    D-924 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04037
    Figure US20090189522A1-20090730-C04038
    Figure US20090189522A1-20090730-C04039
    Figure US20090189522A1-20090730-C04040
  • TABLE 78
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C04041
    Figure US20090189522A1-20090730-C04042
    D-925 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04043
    Figure US20090189522A1-20090730-C04044
    D-926 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04045
    Figure US20090189522A1-20090730-C04046
    D-927 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04047
    Figure US20090189522A1-20090730-C04048
    D-928 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04049
    Figure US20090189522A1-20090730-C04050
    D-929 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04051
    Figure US20090189522A1-20090730-C04052
    D-930 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04053
    Figure US20090189522A1-20090730-C04054
    D-931 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04055
    Figure US20090189522A1-20090730-C04056
    D-932 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04057
    Figure US20090189522A1-20090730-C04058
    D-933 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04059
    Figure US20090189522A1-20090730-C04060
    D-934 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04061
    Figure US20090189522A1-20090730-C04062
    D-935 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04063
    Figure US20090189522A1-20090730-C04064
    D-936 Methyl H Isopropyl H
    Figure US20090189522A1-20090730-C04065
    Figure US20090189522A1-20090730-C04066
    Figure US20090189522A1-20090730-C04067
    Figure US20090189522A1-20090730-C04068
    D-925
    Figure US20090189522A1-20090730-C04069
    Figure US20090189522A1-20090730-C04070
    D-926
    Figure US20090189522A1-20090730-C04071
    Figure US20090189522A1-20090730-C04072
    D-927
    Figure US20090189522A1-20090730-C04073
    Figure US20090189522A1-20090730-C04074
    D-928
    Figure US20090189522A1-20090730-C04075
    Figure US20090189522A1-20090730-C04076
    D-929
    Figure US20090189522A1-20090730-C04077
    Figure US20090189522A1-20090730-C04078
    D-930
    Figure US20090189522A1-20090730-C04079
    Figure US20090189522A1-20090730-C04080
    D-931
    Figure US20090189522A1-20090730-C04081
    Figure US20090189522A1-20090730-C04082
    D-932
    Figure US20090189522A1-20090730-C04083
    Figure US20090189522A1-20090730-C04084
    D-933
    Figure US20090189522A1-20090730-C04085
    Figure US20090189522A1-20090730-C04086
    D-934
    Figure US20090189522A1-20090730-C04087
    Figure US20090189522A1-20090730-C04088
    D-935
    Figure US20090189522A1-20090730-C04089
    Figure US20090189522A1-20090730-C04090
    D-936
    Figure US20090189522A1-20090730-C04091
    Figure US20090189522A1-20090730-C04092
  • TABLE 79
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C04093
    Figure US20090189522A1-20090730-C04094
    D-937 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04095
    Figure US20090189522A1-20090730-C04096
    D-938 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04097
    Figure US20090189522A1-20090730-C04098
    D-939 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04099
    Figure US20090189522A1-20090730-C04100
    D-940 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04101
    Figure US20090189522A1-20090730-C04102
    D-941 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04103
    Figure US20090189522A1-20090730-C04104
    D-942 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04105
    Figure US20090189522A1-20090730-C04106
    D-943 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04107
    Figure US20090189522A1-20090730-C04108
    D-944 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04109
    Figure US20090189522A1-20090730-C04110
    D-945 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04111
    Figure US20090189522A1-20090730-C04112
    D-946 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04113
    Figure US20090189522A1-20090730-C04114
    D-947 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04115
    Figure US20090189522A1-20090730-C04116
    D-948 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04117
    Figure US20090189522A1-20090730-C04118
    Figure US20090189522A1-20090730-C04119
    Figure US20090189522A1-20090730-C04120
    D-937
    Figure US20090189522A1-20090730-C04121
    Figure US20090189522A1-20090730-C04122
    D-938
    Figure US20090189522A1-20090730-C04123
    Figure US20090189522A1-20090730-C04124
    D-939
    Figure US20090189522A1-20090730-C04125
    Figure US20090189522A1-20090730-C04126
    D-940
    Figure US20090189522A1-20090730-C04127
    Figure US20090189522A1-20090730-C04128
    D-941
    Figure US20090189522A1-20090730-C04129
    Figure US20090189522A1-20090730-C04130
    D-942
    Figure US20090189522A1-20090730-C04131
    Figure US20090189522A1-20090730-C04132
    D-943
    Figure US20090189522A1-20090730-C04133
    Figure US20090189522A1-20090730-C04134
    D-944
    Figure US20090189522A1-20090730-C04135
    Figure US20090189522A1-20090730-C04136
    D-945
    Figure US20090189522A1-20090730-C04137
    Figure US20090189522A1-20090730-C04138
    D-946
    Figure US20090189522A1-20090730-C04139
    Figure US20090189522A1-20090730-C04140
    D-947
    Figure US20090189522A1-20090730-C04141
    Figure US20090189522A1-20090730-C04142
    D-948
    Figure US20090189522A1-20090730-C04143
    Figure US20090189522A1-20090730-C04144
  • TABLE 80
          R1       R2       R3       R4
    Figure US20090189522A1-20090730-C04145
    Figure US20090189522A1-20090730-C04146
    D-949 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04147
    Figure US20090189522A1-20090730-C04148
    D-950 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04149
    Figure US20090189522A1-20090730-C04150
    D-951 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04151
    Figure US20090189522A1-20090730-C04152
    D-952 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04153
    Figure US20090189522A1-20090730-C04154
    D-953 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04155
    Figure US20090189522A1-20090730-C04156
    D-954 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04157
    Figure US20090189522A1-20090730-C04158
    D-955 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04159
    Figure US20090189522A1-20090730-C04160
    D-956 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04161
    Figure US20090189522A1-20090730-C04162
    D-957 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04163
    Figure US20090189522A1-20090730-C04164
    D-958 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04165
    Figure US20090189522A1-20090730-C04166
    D-959 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04167
    Figure US20090189522A1-20090730-C04168
    D-960 t-bytyl H Isopropyl H
    Figure US20090189522A1-20090730-C04169
    Figure US20090189522A1-20090730-C04170
    Figure US20090189522A1-20090730-C04171
    Figure US20090189522A1-20090730-C04172
    D-949
    Figure US20090189522A1-20090730-C04173
    Figure US20090189522A1-20090730-C04174
    D-950
    Figure US20090189522A1-20090730-C04175
    Figure US20090189522A1-20090730-C04176
    D-951
    Figure US20090189522A1-20090730-C04177
    Figure US20090189522A1-20090730-C04178
    D-952
    Figure US20090189522A1-20090730-C04179
    Figure US20090189522A1-20090730-C04180
    D-953
    Figure US20090189522A1-20090730-C04181
    Figure US20090189522A1-20090730-C04182
    D-954
    Figure US20090189522A1-20090730-C04183
    Figure US20090189522A1-20090730-C04184
    D-955
    Figure US20090189522A1-20090730-C04185
    Figure US20090189522A1-20090730-C04186
    D-956
    Figure US20090189522A1-20090730-C04187
    Figure US20090189522A1-20090730-C04188
    D-957
    Figure US20090189522A1-20090730-C04189
    Figure US20090189522A1-20090730-C04190
    D-958
    Figure US20090189522A1-20090730-C04191
    Figure US20090189522A1-20090730-C04192
    D-959
    Figure US20090189522A1-20090730-C04193
    Figure US20090189522A1-20090730-C04194
    D-960
    Figure US20090189522A1-20090730-C04195
    Figure US20090189522A1-20090730-C04196
  • TABLE 81
    No R5 R6 R7 R8 A5
    D-961 —H —H —H —H —Me
    D-962 —H —H —H —H —Me
    D-963 —H —H —H —H
    Figure US20090189522A1-20090730-C04197
    D-964 —H —H —H —H
    Figure US20090189522A1-20090730-C04198
    D-965 —H —H —H —H
    Figure US20090189522A1-20090730-C04199
    D-966 —Me —H —Me —H
    Figure US20090189522A1-20090730-C04200
    D-967 —Me —Me —Me —Me
    Figure US20090189522A1-20090730-C04201
    D-968
    Figure US20090189522A1-20090730-C04202
         		—H
    Figure US20090189522A1-20090730-C04203
         		—H —Me
    D-969 —H —Me —H —Me
    Figure US20090189522A1-20090730-C04204
    D-970
    Figure US20090189522A1-20090730-C04205
         		—H
    Figure US20090189522A1-20090730-C04206
         		—H
    Figure US20090189522A1-20090730-C04207
    No A6 A7 A8
    D-961 —Me —Me —Me
    D-962
    Figure US20090189522A1-20090730-C04208
         		—Me —Me
    D-963
    Figure US20090189522A1-20090730-C04209
    Figure US20090189522A1-20090730-C04210
    Figure US20090189522A1-20090730-C04211
    D-964 —Me
    Figure US20090189522A1-20090730-C04212
         		—Me
    D-965
    Figure US20090189522A1-20090730-C04213
    Figure US20090189522A1-20090730-C04214
    Figure US20090189522A1-20090730-C04215
    D-966
    Figure US20090189522A1-20090730-C04216
    Figure US20090189522A1-20090730-C04217
    Figure US20090189522A1-20090730-C04218
    D-967
    Figure US20090189522A1-20090730-C04219
    Figure US20090189522A1-20090730-C04220
    Figure US20090189522A1-20090730-C04221
    D-968
    Figure US20090189522A1-20090730-C04222
         		—Me
    Figure US20090189522A1-20090730-C04223
    D-969
    Figure US20090189522A1-20090730-C04224
    Figure US20090189522A1-20090730-C04225
    Figure US20090189522A1-20090730-C04226
    D-970
    Figure US20090189522A1-20090730-C04227
    Figure US20090189522A1-20090730-C04228
    Figure US20090189522A1-20090730-C04229
  • TABLE 82
    No R5 R6 R7 R8 A5 A6
    D-971 —H —H —H —H —Me
    Figure US20090189522A1-20090730-C04230
    D-972 —H —H —H —H
    Figure US20090189522A1-20090730-C04231
    Figure US20090189522A1-20090730-C04232
    D-973 —H —H —H —H —Me
    Figure US20090189522A1-20090730-C04233
    D-974 —H —H —H —H
    Figure US20090189522A1-20090730-C04234
    Figure US20090189522A1-20090730-C04235
    D-975 —H —H —H —H
    Figure US20090189522A1-20090730-C04236
    Figure US20090189522A1-20090730-C04237
    D-976 —H —H —H —H
    Figure US20090189522A1-20090730-C04238
    Figure US20090189522A1-20090730-C04239
    D-977 —H —H —H —H
    Figure US20090189522A1-20090730-C04240
    Figure US20090189522A1-20090730-C04241
    D-978 —Me —H —Me —H —Me
    Figure US20090189522A1-20090730-C04242
    D-979 —Me —Me —Me —Me
    Figure US20090189522A1-20090730-C04243
    Figure US20090189522A1-20090730-C04244
    D-980 —Me —H —Me —H
    Figure US20090189522A1-20090730-C04245
    Figure US20090189522A1-20090730-C04246
    No A7 A8
    D-971 —Me
    Figure US20090189522A1-20090730-C04247
    D-972
    Figure US20090189522A1-20090730-C04248
    Figure US20090189522A1-20090730-C04249
    D-973 —Me
    Figure US20090189522A1-20090730-C04250
    D-974
    Figure US20090189522A1-20090730-C04251
    Figure US20090189522A1-20090730-C04252
    D-975
    Figure US20090189522A1-20090730-C04253
    Figure US20090189522A1-20090730-C04254
    D-976
    Figure US20090189522A1-20090730-C04255
    Figure US20090189522A1-20090730-C04256
    D-977
    Figure US20090189522A1-20090730-C04257
    Figure US20090189522A1-20090730-C04258
    D-978 —Me
    Figure US20090189522A1-20090730-C04259
    D-979
    Figure US20090189522A1-20090730-C04260
    Figure US20090189522A1-20090730-C04261
    D-980
    Figure US20090189522A1-20090730-C04262
    Figure US20090189522A1-20090730-C04263
  • TABLE 83
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-981 —H —H —H —H —Me
    Figure US20090189522A1-20090730-C04264
         		—Me
    Figure US20090189522A1-20090730-C04265
    D-982 —H —H —H —H
    Figure US20090189522A1-20090730-C04266
    Figure US20090189522A1-20090730-C04267
    Figure US20090189522A1-20090730-C04268
    Figure US20090189522A1-20090730-C04269
    D-983 —H —H —H —H —Me
    Figure US20090189522A1-20090730-C04270
         		—Me
    Figure US20090189522A1-20090730-C04271
    D-984 —H —H —H —H
    Figure US20090189522A1-20090730-C04272
    Figure US20090189522A1-20090730-C04273
    Figure US20090189522A1-20090730-C04274
    Figure US20090189522A1-20090730-C04275
    D-985 —H —H —H —H
    Figure US20090189522A1-20090730-C04276
    Figure US20090189522A1-20090730-C04277
    Figure US20090189522A1-20090730-C04278
    Figure US20090189522A1-20090730-C04279
    D-986 —H —H —H —H
    Figure US20090189522A1-20090730-C04280
    Figure US20090189522A1-20090730-C04281
    Figure US20090189522A1-20090730-C04282
    Figure US20090189522A1-20090730-C04283
    D-987 —H —H —H —H
    Figure US20090189522A1-20090730-C04284
    Figure US20090189522A1-20090730-C04285
    Figure US20090189522A1-20090730-C04286
    Figure US20090189522A1-20090730-C04287
    D-988 —Me —H —Me —H —Me
    Figure US20090189522A1-20090730-C04288
         		—Me
    Figure US20090189522A1-20090730-C04289
    D-989 —H —H —H —H
    Figure US20090189522A1-20090730-C04290
    Figure US20090189522A1-20090730-C04291
    Figure US20090189522A1-20090730-C04292
    Figure US20090189522A1-20090730-C04293
    D-990 —H —H —H —H
    Figure US20090189522A1-20090730-C04294
    Figure US20090189522A1-20090730-C04295
    Figure US20090189522A1-20090730-C04296
    Figure US20090189522A1-20090730-C04297
  • TABLE 84
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-991 —H —H —H —H
    Figure US20090189522A1-20090730-C04298
    Figure US20090189522A1-20090730-C04299
    Figure US20090189522A1-20090730-C04300
    Figure US20090189522A1-20090730-C04301
    D-992 —H —H —H —H
    Figure US20090189522A1-20090730-C04302
    Figure US20090189522A1-20090730-C04303
    Figure US20090189522A1-20090730-C04304
    Figure US20090189522A1-20090730-C04305
    D-993 —H —H —H —H
    Figure US20090189522A1-20090730-C04306
    Figure US20090189522A1-20090730-C04307
    Figure US20090189522A1-20090730-C04308
    Figure US20090189522A1-20090730-C04309
    D-994 —H —H —H —H
    Figure US20090189522A1-20090730-C04310
    Figure US20090189522A1-20090730-C04311
    Figure US20090189522A1-20090730-C04312
    Figure US20090189522A1-20090730-C04313
    D-995 —H —H —H —H
    Figure US20090189522A1-20090730-C04314
    Figure US20090189522A1-20090730-C04315
    Figure US20090189522A1-20090730-C04316
    Figure US20090189522A1-20090730-C04317
    D-996 —H —H —H —H
    Figure US20090189522A1-20090730-C04318
    Figure US20090189522A1-20090730-C04319
    Figure US20090189522A1-20090730-C04320
    Figure US20090189522A1-20090730-C04321
    D-997 —H —H —H —H
    Figure US20090189522A1-20090730-C04322
    Figure US20090189522A1-20090730-C04323
    Figure US20090189522A1-20090730-C04324
    Figure US20090189522A1-20090730-C04325
    D-998 —H —H —H —H
    Figure US20090189522A1-20090730-C04326
    Figure US20090189522A1-20090730-C04327
    Figure US20090189522A1-20090730-C04328
    Figure US20090189522A1-20090730-C04329
    D-999 —H —H —H —H
    Figure US20090189522A1-20090730-C04330
    Figure US20090189522A1-20090730-C04331
    Figure US20090189522A1-20090730-C04332
    Figure US20090189522A1-20090730-C04333
    D-1000 —Me —H —H —H
    Figure US20090189522A1-20090730-C04334
    Figure US20090189522A1-20090730-C04335
    Figure US20090189522A1-20090730-C04336
    Figure US20090189522A1-20090730-C04337
  • TABLE 85
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-1001 —H —H —H —H
    Figure US20090189522A1-20090730-C04338
    Figure US20090189522A1-20090730-C04339
    Figure US20090189522A1-20090730-C04340
    Figure US20090189522A1-20090730-C04341
    D-1002 —H —H —H —H
    Figure US20090189522A1-20090730-C04342
    Figure US20090189522A1-20090730-C04343
    Figure US20090189522A1-20090730-C04344
    Figure US20090189522A1-20090730-C04345
    D-1003 —H —H —H —H
    Figure US20090189522A1-20090730-C04346
    Figure US20090189522A1-20090730-C04347
    Figure US20090189522A1-20090730-C04348
    Figure US20090189522A1-20090730-C04349
    D-1004 —H —H —H —H
    Figure US20090189522A1-20090730-C04350
    Figure US20090189522A1-20090730-C04351
    Figure US20090189522A1-20090730-C04352
    Figure US20090189522A1-20090730-C04353
    D-1005 —H —H —H —H
    Figure US20090189522A1-20090730-C04354
    Figure US20090189522A1-20090730-C04355
    Figure US20090189522A1-20090730-C04356
    Figure US20090189522A1-20090730-C04357
    D-1006 —H —H —H —H
    Figure US20090189522A1-20090730-C04358
    Figure US20090189522A1-20090730-C04359
    Figure US20090189522A1-20090730-C04360
    Figure US20090189522A1-20090730-C04361
    D-1007 —H —H —H —H
    Figure US20090189522A1-20090730-C04362
    Figure US20090189522A1-20090730-C04363
    Figure US20090189522A1-20090730-C04364
    Figure US20090189522A1-20090730-C04365
    D-1008 —H —H —H —H
    Figure US20090189522A1-20090730-C04366
    Figure US20090189522A1-20090730-C04367
    Figure US20090189522A1-20090730-C04368
    Figure US20090189522A1-20090730-C04369
    D-1009 —H —H —H —H
    Figure US20090189522A1-20090730-C04370
    Figure US20090189522A1-20090730-C04371
    Figure US20090189522A1-20090730-C04372
    Figure US20090189522A1-20090730-C04373
    D-1010 —Me —H —Me —H
    Figure US20090189522A1-20090730-C04374
    Figure US20090189522A1-20090730-C04375
    Figure US20090189522A1-20090730-C04376
    Figure US20090189522A1-20090730-C04377
  • TABLE 86
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-1011 —H —H —H —H
    Figure US20090189522A1-20090730-C04378
    Figure US20090189522A1-20090730-C04379
    Figure US20090189522A1-20090730-C04380
    Figure US20090189522A1-20090730-C04381
    D-1012 —H —H —H —H
    Figure US20090189522A1-20090730-C04382
    Figure US20090189522A1-20090730-C04383
    Figure US20090189522A1-20090730-C04384
    Figure US20090189522A1-20090730-C04385
    D-1013 —H —H —H —H
    Figure US20090189522A1-20090730-C04386
    Figure US20090189522A1-20090730-C04387
    Figure US20090189522A1-20090730-C04388
    Figure US20090189522A1-20090730-C04389
    D-1014 —H —H —H —H
    Figure US20090189522A1-20090730-C04390
    Figure US20090189522A1-20090730-C04391
    Figure US20090189522A1-20090730-C04392
    Figure US20090189522A1-20090730-C04393
    D-1015 —H —H —H —H
    Figure US20090189522A1-20090730-C04394
    Figure US20090189522A1-20090730-C04395
    Figure US20090189522A1-20090730-C04396
    Figure US20090189522A1-20090730-C04397
    D-1016 —H —H —H —H
    Figure US20090189522A1-20090730-C04398
    Figure US20090189522A1-20090730-C04399
    Figure US20090189522A1-20090730-C04400
    Figure US20090189522A1-20090730-C04401
    D-1017 —H —H —H —H
    Figure US20090189522A1-20090730-C04402
    Figure US20090189522A1-20090730-C04403
    Figure US20090189522A1-20090730-C04404
    Figure US20090189522A1-20090730-C04405
    D-1018 —H —H —H —H
    Figure US20090189522A1-20090730-C04406
    Figure US20090189522A1-20090730-C04407
    Figure US20090189522A1-20090730-C04408
    Figure US20090189522A1-20090730-C04409
    D-1019 —H —H —H —H
    Figure US20090189522A1-20090730-C04410
    Figure US20090189522A1-20090730-C04411
    Figure US20090189522A1-20090730-C04412
    Figure US20090189522A1-20090730-C04413
    D-1020 —Me —H —Me —H
    Figure US20090189522A1-20090730-C04414
    Figure US20090189522A1-20090730-C04415
    Figure US20090189522A1-20090730-C04416
    Figure US20090189522A1-20090730-C04417
  • TABLE 87
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-1021 —H —H —H —H
    Figure US20090189522A1-20090730-C04418
    Figure US20090189522A1-20090730-C04419
    Figure US20090189522A1-20090730-C04420
    Figure US20090189522A1-20090730-C04421
    D-1022 —H —H —H —H
    Figure US20090189522A1-20090730-C04422
    Figure US20090189522A1-20090730-C04423
    Figure US20090189522A1-20090730-C04424
    Figure US20090189522A1-20090730-C04425
    D-1023 —H —H —H —H
    Figure US20090189522A1-20090730-C04426
    Figure US20090189522A1-20090730-C04427
    Figure US20090189522A1-20090730-C04428
    Figure US20090189522A1-20090730-C04429
    D-1024 —H —H —H —H
    Figure US20090189522A1-20090730-C04430
    Figure US20090189522A1-20090730-C04431
    Figure US20090189522A1-20090730-C04432
    Figure US20090189522A1-20090730-C04433
    D-1025 —H —H —H —H
    Figure US20090189522A1-20090730-C04434
    Figure US20090189522A1-20090730-C04435
    Figure US20090189522A1-20090730-C04436
    Figure US20090189522A1-20090730-C04437
    D-1026 —H —H —H —H
    Figure US20090189522A1-20090730-C04438
    Figure US20090189522A1-20090730-C04439
    Figure US20090189522A1-20090730-C04440
    Figure US20090189522A1-20090730-C04441
    D-1027 —H —H —H —H
    Figure US20090189522A1-20090730-C04442
    Figure US20090189522A1-20090730-C04443
    Figure US20090189522A1-20090730-C04444
    Figure US20090189522A1-20090730-C04445
    D-1028 Me —H Me —H
    Figure US20090189522A1-20090730-C04446
    Figure US20090189522A1-20090730-C04447
    Figure US20090189522A1-20090730-C04448
    Figure US20090189522A1-20090730-C04449
    D-1029 —H —H —H —H
    Figure US20090189522A1-20090730-C04450
    Figure US20090189522A1-20090730-C04451
    Figure US20090189522A1-20090730-C04452
    Figure US20090189522A1-20090730-C04453
    D-1030 —H —H —H —H
    Figure US20090189522A1-20090730-C04454
    Figure US20090189522A1-20090730-C04455
    Figure US20090189522A1-20090730-C04456
    Figure US20090189522A1-20090730-C04457
  • TABLE 88
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-1031 —H —H —H —H
    Figure US20090189522A1-20090730-C04458
    Figure US20090189522A1-20090730-C04459
    Figure US20090189522A1-20090730-C04460
    Figure US20090189522A1-20090730-C04461
    D-1032 —H —H —H —H
    Figure US20090189522A1-20090730-C04462
    Figure US20090189522A1-20090730-C04463
    Figure US20090189522A1-20090730-C04464
    Figure US20090189522A1-20090730-C04465
    D-1033 —H —H —H —H
    Figure US20090189522A1-20090730-C04466
    Figure US20090189522A1-20090730-C04467
    Figure US20090189522A1-20090730-C04468
    Figure US20090189522A1-20090730-C04469
    D-1034 —H —H —H —H
    Figure US20090189522A1-20090730-C04470
    Figure US20090189522A1-20090730-C04471
    Figure US20090189522A1-20090730-C04472
    Figure US20090189522A1-20090730-C04473
    D-1035 —H —H —H —H
    Figure US20090189522A1-20090730-C04474
    Figure US20090189522A1-20090730-C04475
    Figure US20090189522A1-20090730-C04476
    Figure US20090189522A1-20090730-C04477
    D-1036 —H —H —H —H
    Figure US20090189522A1-20090730-C04478
    Figure US20090189522A1-20090730-C04479
    Figure US20090189522A1-20090730-C04480
    Figure US20090189522A1-20090730-C04481
    D-1037 —H —H —H —H
    Figure US20090189522A1-20090730-C04482
    Figure US20090189522A1-20090730-C04483
    Figure US20090189522A1-20090730-C04484
    Figure US20090189522A1-20090730-C04485
    D-1038 —H —H —H —H
    Figure US20090189522A1-20090730-C04486
    Figure US20090189522A1-20090730-C04487
    Figure US20090189522A1-20090730-C04488
    Figure US20090189522A1-20090730-C04489
    D-1039 —H —H —H —H
    Figure US20090189522A1-20090730-C04490
    Figure US20090189522A1-20090730-C04491
    Figure US20090189522A1-20090730-C04492
    Figure US20090189522A1-20090730-C04493
    D-1040 —Me —H —Me —H
    Figure US20090189522A1-20090730-C04494
    Figure US20090189522A1-20090730-C04495
    Figure US20090189522A1-20090730-C04496
    Figure US20090189522A1-20090730-C04497
  • TABLE 89
    No R5 R6 R7 R8 A5 A6 A7 A8
    D-1041 —H —H —H —H
    Figure US20090189522A1-20090730-C04498
    Figure US20090189522A1-20090730-C04499
    Figure US20090189522A1-20090730-C04500
    Figure US20090189522A1-20090730-C04501
    D-1042 —H —H —H —H
    Figure US20090189522A1-20090730-C04502
    Figure US20090189522A1-20090730-C04503
    Figure US20090189522A1-20090730-C04504
    Figure US20090189522A1-20090730-C04505
    D-1043 —H —H —H —H
    Figure US20090189522A1-20090730-C04506
    Figure US20090189522A1-20090730-C04507
    Figure US20090189522A1-20090730-C04508
    Figure US20090189522A1-20090730-C04509
    D-1044 —H —H —H —H
    Figure US20090189522A1-20090730-C04510
    Figure US20090189522A1-20090730-C04511
    Figure US20090189522A1-20090730-C04512
    Figure US20090189522A1-20090730-C04513
    D-1045 —H —H —H —H
    Figure US20090189522A1-20090730-C04514
    Figure US20090189522A1-20090730-C04515
    Figure US20090189522A1-20090730-C04516
    Figure US20090189522A1-20090730-C04517
    D-1046 —H —H —H —H
    Figure US20090189522A1-20090730-C04518
    Figure US20090189522A1-20090730-C04519
    Figure US20090189522A1-20090730-C04520
    Figure US20090189522A1-20090730-C04521
    D-1047 —H —H —H —H
    Figure US20090189522A1-20090730-C04522
    Figure US20090189522A1-20090730-C04523
    Figure US20090189522A1-20090730-C04524
    Figure US20090189522A1-20090730-C04525
    D-1048 Me —H Me —H
    Figure US20090189522A1-20090730-C04526
    Figure US20090189522A1-20090730-C04527
    Figure US20090189522A1-20090730-C04528
    Figure US20090189522A1-20090730-C04529
    D-1049 —H —H —H —H
    Figure US20090189522A1-20090730-C04530
    Figure US20090189522A1-20090730-C04531
    Figure US20090189522A1-20090730-C04532
    Figure US20090189522A1-20090730-C04533
    D-1050 —H —H —H —H
    Figure US20090189522A1-20090730-C04534
    Figure US20090189522A1-20090730-C04535
    Figure US20090189522A1-20090730-C04536
    Figure US20090189522A1-20090730-C04537
  • In the aromatic amine derivative of the present invention, since the aryl group (in particular, a benzene ring), the alkyl group, the cycloalkyl group or the heterocyclic group is connected to a diaminocrysene structure as a light emission center, an association between the compounds is prevented, resulting in a prolonged lifetime thereof. Moreover, because coupling a bulky substituent to the chrysene backbone structure increases a steric repulsion against the amine structure, the lifetime prolongs further.
  • Further, the aromatic amine derivatives have a strong fluorescence in a solid state, and are excellent in an electric field light emission, which leads to a fluorescent quantum efficiency as high as 0.3 or more. In addition, the aromatic amine derivatives of the present invention exhibit not only excellent capabilities of injecting and transporting holes from the metal electrode or organic thin film layers, but also excellent capabilities of injecting and transporting electrons from the metal electrode or organic thin film layers and, therefore, are usefully employable as light emitting materials, particularly doping materials for organic EL devices. Besides, the aromatic amine derivatives of the present invention may be used together with other hole transporting materials, electron transporting materials or doping materials.
  • The organic EL device of the present invention comprises one or plural organic thin film layers sandwiched between an anode and a cathode. In the case of one layer type, a light emitting layer as the organic thin film layer is sandwiched between the anode and cathode. The light emitting layer contains the light emitting material and may further contain a hole injecting material and an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. The aromatic amine derivatives of the present invention have an enhanced light emitting property and excellent hole injecting capability and hole transporting capability as well as excellent electron injecting capability and electron transporting capability and, therefore, can be employed as a light emitting material or a doping material in the light emitting layer.
  • In the organic EL device of the present invention, the light emitting layer contains the aromatic amine derivative of the present invention in an amount of preferably 0.1 to 20% by weight and more preferably 1 to 10% by weight. Further, the aromatic amine derivatives of the present invention exhibit not only an extremely high fluorescent quantum efficiency but also high hole transporting capability and electron transporting capability, and further are capable of forming a uniform thin film, so that the light emitting layer may be formed from the aromatic amine derivatives only.
  • On the other hand, in the case where the organic EL device of the present invention comprises two or more organic thin film layers having at least the light emitting layer which are sandwiched between the cathode and anode, the organic thin film layers preferably include an organic layer containing the aromatic amine derivative of the present invention as an essential component which is provided between the anode and the light emitting layer. Such an organic layer may be a hole injecting layer, a hole transporting layer, etc.
  • Further, in a case where the aromatic amine derivative of the present invention is employed as a doping material, it is preferable that at least one kind selected from the group consisting of anthracene derivatives of a following general formula (3), anthracene derivatives of a following general formula (4) and pyrene derivatives of a following general formula (5) is employed as a host material.
  • Figure US20090189522A1-20090730-C04538
  • In the general formula (3), X1 and X2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms or a halogen atom; e and f each independently represents an integer of 0 to 4; when e or f is 2 or greater, X1 and X2 may be the same with or different from each other.
  • Ar1 and Ar2 each independently represents a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms; at least one of Ar1 or Ar2 represents a substituted or unsubstituted aryl group with a condensed ring and having 10 to 50 ring carbon atoms; and m represents an integer of 1 to 3. When m is 2 or greater, a group within the above parentheses: [ ] may be the same with or different from each other.
  • Specific examples and substituents of the X1, X2, Ar1 and Ar2 are the same as those explained about the foregoing general formula (1).
  • Figure US20090189522A1-20090730-C04539
  • In the general formula (4), X1 to X3 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms or a halogen atom; e, f, and g each independently represents an integer of 0 to 4. When e, f, or g is 2 or greater, X1, X2 and X3 may be the same with or different from each other.
  • Ar1 represents a substituted or unsubstituted aryl group with a condensed ring and having 10 to 50 ring carbon atoms and Ar3 represents a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms; n represents an integer of 1 to 3. When n is 2 or greater, a group within the above parentheses: [ ] may be the same with or different from each other.
  • Specific examples and substituents of the X1 to X3, Ar1 and Ar3 are the same as those explained about the foregoing general formula (1).
  • Specific examples of anthracene derivative represented by the general formulae (3) and (4) will be illustrated below, though not particularly limited thereto.
  • Figure US20090189522A1-20090730-C04540
    Figure US20090189522A1-20090730-C04541
    Figure US20090189522A1-20090730-C04542
    Figure US20090189522A1-20090730-C04543
    Figure US20090189522A1-20090730-C04544
    Figure US20090189522A1-20090730-C04545
    Figure US20090189522A1-20090730-C04546
  • In the general formula (5), Ar5 and Ar6 each represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
  • L1 and L2 each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted dibenzosilolylene group;
    s represents an integer of 0 to 2, p represents an integer of 1 to 4, q represents an integer of 0 to 2 and r represents an integer of 0 to 4; and
    L1 or Ar5 bonds to any one of 1 to 5 position of pyrene, also L2 or Ar6 bonds to any one of 6 to 10 position thereof,
    however, when p+r is an even number, Ar5, Ar6, L1 and L2 satisfy a following requirement (1) or a requirement (2):
    (1) Ar5·Ar6 and/or L1·L2 (wherein ≠ means that each group has a different structure)
    (2) when Ar5=Ar6, and L1=L2
    (2-1) s≠q and/or p≠r, or
    (2-2) when s=q, and p=r,
    (2-2-1) both L1 and L2 or pyrene each bond respectively to different positions of Ar5 and Ar6, or
    (2-2-2) both L1 and L2 or pyrene each bonds respectively to the same position of Ar5 and Ar6, excluding a case where both L1 and L2 or both Ar5 and Ar6 bond to 1 and 6 positions thereof, or 2 and 7 positions thereof.
  • Specific examples and substituents of the Ar5, Ar6, L1 and L2 are the same as those explained about the foregoing general formula (1).
  • Specific examples of the pyrene derivative represented by the general formula (5) will be illustrated below, though not particularly limited thereto.
  • Figure US20090189522A1-20090730-C04547
    Figure US20090189522A1-20090730-C04548
    Figure US20090189522A1-20090730-C04549
    Figure US20090189522A1-20090730-C04550
    Figure US20090189522A1-20090730-C04551
  • Examples of the organic EL device of a multilayer type include those having multilayer structures such as (an anode/a hole injecting layer/a light emitting layer/a cathode), (an anode/a light emitting layer/an electron injecting layer/a cathode) and (an anode/a hole injecting layer/a light emitting layer/an electron injecting layer/a cathode).
  • The multilayers may also optionally contain, in addition to the aromatic amine derivatives of the present invention, conventionally known materials such as light emitting materials, doping materials, hole injecting materials and electron injecting materials according to requirements. The organic EL device having such a multilayer structure can be prevented from suffering from deterioration in luminance and lifetime due to quenching. If required, the light emitting materials, doping materials, hole injecting materials and electron injecting materials may be used in combination with each other. The use of the doping materials enables the resultant device to be improved in luminance of light emission and efficiency of light emission, and further emit a red color light or a blue color light. Further, in the organic EL device of the present invention, the hole injecting layer, the light emitting layer and the electron injecting layer may respectively have a multilayer structure including two or more layers. In these cases, a layer injecting holes from the electrode is called as a hole injecting layer, and a layer for accepting the holes from the hole injecting layer and transporting the holes to the light emitting layer is called as a hole transporting layer. Also, a layer injecting electrons the electrode is called as an electron injecting layer, and a layer transporting for accepting the electrons from the electron injecting layer and transporting the electrons to the light emitting layer is called as an electron transporting layer. Those respective layers may be selectively used according to various factors such as energy level of the materials used, heat resistance, and adhesion to the organic thin film layers or the metal electrodes.
  • Examples of the host material or the doping material besides the foregoing general formulae (3) to (5) employable for the light emitting layer together with the aromatic amine derivative of the present invention include condensed mass aromatic compound such as naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenyl cyclopentadiene, fluorene, spiro fluorene, 9,10-diphenylanthracene, 9,10-bis(phenyl-ethynyl)anthracene, 1,4-bis(9′-ethynyl anthracenyl)benzene and those derivatives; organometallic complex such as tris(8-quinolinolat)aluminium, bis-(2-methyl-8-quinolinolat)-4-(phenylphenolinat) aluminum, etc.; triarylamine derivative, styryl amine derivative, stilbene derivative, coumarine derivative, pyran derivative, oxazone derivative, benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamate ester derivative, diketo pyrrolopyrrole derivative, acridone derivative, quinacridon derivative, etc.; though not particularly limited thereto.
  • The hole injecting material is preferably made of compounds which have a good hole transporting capability as well as excellent capabilities of accepting holes injected from the anode and injecting the holes into the light emitting layer or light emitting material, prevent excited particles produced in the light emitting layer from moving into the electron injecting layer or electron injecting material, and exhibit an excellent capability of forming a thin film. Specific examples of the hole injecting material include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazole thione, pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acyl hydrazone, polyaryl alkanes, stilbene, butadiene, benzidine-type triphenyl amine, styryl amine-type triphenyl amine, diamine-type triphenyl amine and derivatives thereof, as well as polyvinyl carbazoles, polysilanes, and high molecular materials such as electro-conductive polymers, though not particularly limited thereto.
  • Among those hole injecting materials usable in the organic EL device of the present invention, more effective hole injecting materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • Specific examples of the aromatic tertiary amine derivatives include triphenyl amine, tritolyl amine, tolyldiphenyl amine, N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-phenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N,N′-(methylphenyl)-N,N′-(4-n-butylphenyl)-phenanthrene-9,10-diamine, N,N-bis(4-di-4-tolylaminophenyl)-4-phenyl-cyclohexane, and oligomers and polymers having these aromatic tertiary amine skeletons, though not particularly limited thereto.
  • Specific examples of the phthalocyanine (Pc) derivatives include phthalocyanine derivatives such as H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc, GaPc—O—GaPc, as well as naphthalocyanine derivatives, though not particularly limited thereto.
  • Also, in the organic EL device of the present invention, between the light emitting layer and the anode, there is preferably formed a layer such as the above hole transporting layer or hole injecting layer containing those aromatic tertiary amine derivatives and/or phthalocyanine derivatives.
  • The electron injecting material is preferably made of compounds which have a good electron transporting capability as well as excellent capabilities of accepting electrons injected from the cathode and injecting the electrons into the light emitting layer or light emitting material, prevent excited particles produced in the light emitting layer from moving into the hole injecting layer, and exhibit an excellent capability of forming a thin film. Specific examples of the electron injecting material include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrane dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, though not particularly limited thereto. Further, an electron accepting substance and an electron donating substance may be added to the hole injecting material and the electron injecting material, respectively, for enhanced sensitization thereof.
  • In the organic EL device of the present invention, among these electron injecting materials, more effective electron injecting materials are metal complex compounds and five-member ring derivatives having a nitrogen atom.
  • Specific examples of the metal complex compounds include 8-hydroxyquinolinatolithium, bis(8-hydroxy(quinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)m anganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato)gallium, though not particularly limited thereto.
  • The five-member ring derivatives having a nitrogen atom are preferably derivatives of oxazole, thiazole, oxadiazole, thiadiazole or triazole. Specific examples of the nitrogen-containing five-member ring derivatives include 2,5-bis(1-phenyl)-1,3,4-oxazole, dimethyl POPOP, 2,5-bis(1-phenyl)-1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole, 2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-oxadiazole, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole, 1,4-bis[2-(5-phenyloxadiazolyl)]benzene, 1,4-bis[2-(5-phenyloxadiazolyl)-4-tert-butylbenzene], 2-(4′-tert-butylphenyl)-5-(4″-biphenyl-1,3,4-thiadiazole, 2,5-bis(1-naphthyl)-1,3,4-thiadiazole, 1,4-bis[2-(5-phenylthiadiazolyl)]benzene, 2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-triazole, 2,5-bis(1-naphthyl)-1,3,4-triazole, and 1,4-bis[2-(5-phenyltriazolyl)]benzene, though not particularly limited thereto.
  • In the organic EL device of the present invention, the light emitting layer may also optionally contain, in addition to the aromatic amine derivatives represented by the general formula (1), at least one material selected from the group consisting of light emitting materials, doping materials, hole injecting materials and electron injecting materials. The organic EL device of the present invention may be further provided with a protective layer on a surface thereof, or the whole part thereof may be protected with silicone oil, resins, etc., in order to enhance stability thereof against temperature, humidity, atmosphere, etc.
  • The anode of the organic EL device according to the present invention may be suitably made of an electro-conductive material having a work function more than 4 eV. Examples of the electro-conductive material for the anode include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium and alloys thereof, metal oxides such as tin oxide and indium oxide which are used for ITO substrates or NESA substrates, and organic electro-conductive resins such as polythiophene and polypyrrole. The cathode of the organic EL device according to the present invention may be suitably made of an electro-conductive material having a work function of 4 eV or less. Examples of the electro-conductive material for the cathode include magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride and alloys thereof, though not particularly limited thereto. Typical examples of the alloys include alloys of magnesium and silver, alloys of magnesium and indium, and alloys of lithium and aluminum, though not particularly limited thereto. The ratio between the constituting metals in the alloys may be controlled and appropriately determined depending upon temperature of vapor deposition sources, atmosphere, vacuum degree, etc. The anode and cathode may be constituted of two or more layers, if required.
  • At least one surface of the organic EL device of the present invention preferably exhibits a sufficient transparency in a wavelength range of light emitted therefrom in order to enhance an efficiency of light emission thereof. Further, the substrate for the device is also preferably transparent. The transparent electrode is formed using the above electro-conductive material by vapor deposition method, sputtering method, etc., so as to ensure a desirable transparency thereof. The electrode disposed on a light emitting surface of the device preferably has a light transmittance of 10% or greater. The substrate is not particularly limited as long as it suitably has a good mechanical and thermal strength as well as a good transparency. Examples of the substrate include glass substrates and transparent resin films. Specific examples of the transparent resin films include films made of polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylons, polyether ether ketones, polysulfones, polyether sulfones, tetrafluoroethylene-perfluoroalkylvinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride, polyesters, polycarbonates, polyurethanes, polyimides, polyether imides and polypropylene.
  • The respective layers of the organic EL device of the present invention may be formed by either a dry film-forming process such as vacuum deposition, sputtering, plasma and ion-plating, or a wet film-forming process such as spin-coating, dipping and flow-coating. The thickness of the respective layers is not particularly limited, but should be adjusted to an appropriate range. When the thickness is too large, a large electric voltage must be applied to the device in order to achieve a predetermined light output, resulting in a poor efficiency of light emission. On the other hand, when the thickness is too small, pinholes tend to be formed in the layers, thereby failing to obtain a sufficient luminance of light emission even upon applying an electric field thereto. The suitable thickness of the respective layers is usually in the range of from 5 nm to 10 μm and preferably from 10 nm to 0.2 μm.
  • In the wet film-forming process, materials constituting the respective layers are dissolved or dispersed in a suitable solvent such as ethanol, chloroform, tetrahydrofuran and dioxane to form a thin film thereof. The solvent used for forming the respective layers is not particularly limited. Also, suitable resins or additives may be added to the respective organic thin film layers for the purposes of improving a film-forming property, preventing formation of pinholes in the resultant film, etc. Examples of the resins usable for the above purposes include insulating resins such as polystyrene, polycarbonates, polyarylates, polyesters, polyamides, polyurethanes, polysulfones, polymethyl methacrylate, polymethyl acrylate and celluloses as well as copolymers thereof, photoconductive resins such as poly-N-vinyl carbazole and polysilanes, and electro-conductive resins such as polythiophene and polypyrrole. Examples of the additives include antioxidants, ultraviolet absorbers and plasticizers.
  • The organic EL device of the present invention is suitably applied to, for example, planar light-emitting members such as a wall-hanging type television flat panel displays or so, light sources for copiers, printers, back light for liquid crystal displays and, measuring instruments, display panels, marker light, etc. Further, the material of the present invention can be used not only for organic EL devices but also in other applications such as electronic photographic members, photoelectric converter elements, solar cells, image sensors, etc.
    • EXAMPLE
  • The present invention will be described in more detail by reference to the following examples.
    • Synthesis Example 1 Synthesis of Chemical Compound (4) (1-1) Synthesis of 2-bromo-6-methylnaphthalene
  • Under an atmospheric argon gas flow, trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol), dichloro (diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5% by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into a three neck flask with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to −20° C. After slowly dripping methylmagnesiumbromide in an amount of 90 milliliter (90 mmol, 1 mol/liter (tetrahydrofuran)) into the flask, the resultant solution was stirred under heating at the temperature of 80° C. for 4 hours. After the reaction terminated, adding dilute hydrochloric acid in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium bicarbonate solution and sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=90/10), and as a result, 9.4 g of aimed compound (white crystal) was obtained (yield: 47%).
    • (1-2) Synthesis of 2-(6-methyl-2-naphthyl)benzaldehyde
  • Under an atmospheric argon gas flow, 2-bromo-6-methylnaphthalene in an amount of 6.6 g (30 mmol), 2-formylphenylboronic acid in an amount of 5.4 g (36 mmol), (tetrakistriphenylphosphine)palladium in an amount of 0.7 g (0.6 mmol), 2N sodium carbonate aqueous solution in an amount of 45 milliliter and dimethoxyethane in an amount of 90 milliliter were placed into a three neck flask with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was refluxed under heating for 8 hours. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=60/40), and as a result, 6.7 g of aimed compound (white crystal) was obtained (yield: 91%).
    • (1-3) Synthesis of 2-((2-methoxyvinyl)phenyl)-6-methylnaphthalene
  • Under an atmospheric argon gas flow, 2-(6-methyl-2-naphthyl)benzaldehyde in an amount of 13.7 g (55 mmol), (methoxymethyl)triphenylphosphoniumchloride in an amount of 21 g (61 mmol), t butoxy potassium in an amount of 7.5 g (67 mmol) and desiccated tetrahydrofuran in an amount of 250 milliliter were placed into a three neck flask with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for a night. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=10/90), and as a result, 12.8 g of aimed compound (white crystal) was obtained (yield: 84%).
    • (1-4) Synthesis of 2-methylchrysene
  • Under an atmospheric argon gas flow, 2-((2-methoxyvinyl)phenyl)-6-methylnaphthalene in an amount of 12.8 g (46 mmol), several drops of methyl acid, and desiccated dichloromethane in an amount of 100 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for 8 hours. After the reaction terminated, adding sodium bicarbonate solution in an amount of 100 milliliter into the reacted solution, crystals were separated by filtration. The resultant crude product was washed with the use of water and methanol, and then, it was vacuum dried at the temperature of 50° C. for 8 hours, and as a result, 8.2 g of aimed compound (white crystal) was obtained (yield: 73%).
    • (1-5) Synthesis of 2-methyl-6,12-dibromochrysene
  • Under an atmospheric argon gas flow, 2-methylchrysene in an amount of 8.2 g (34 mmol), N-bromosuccinimide in an amount of 14.5 g (81 mmol) and N,N-dimethylformamide in an amount of 400 milliliter were placed into a three neck flask with a cooling pipe and having a capacity of 1 liter, and the resultant solution was stirred at the room temperature for one night. After the reaction terminated, adding water in an amount of 300 milliliter into the reacted solution, crystals were separated by filtration. The resultant crude product was washed with the use of water and methanol, and then, it was re-crystallized in 100 milliliter of toluene, and as a result, 8.8 g of aimed compound (white crystal) was obtained (yield: 65%).
    • (1-6) Synthesis of Chemical Compound (4)
  • Under an atmospheric argon gas flew, 2-methyl-6,12-dibromochrysene in an amount of 4.0 g (10 mmol), bis(3,4-dimethylphenyl)amine in an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 5.8 g of pale yellow powders were obtained. The pale yellow powders were identified as Compound (4) from the result in accordance with Field Desorption Mass Spectrum (FD-MS) measurement (yield: 85%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (4) is shown in FIG. 1. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (4) among the toluene solvent were 400 nm and 456 nm respectively.
    • Synthesis Example 2 Synthesis of Compound (9) (2-1) Synthesis of 2-isopropyl-6,12-dibromo chrysene
  • An aimed compound was obtained in a similar manner as Synthesis Example 1 from the step (1-1) to the step (1-5) except that isopropylmagnesium bromide was employed instead of methylmagnesium bromide in the step (1-1).
    • (2-2) Synthesis of Compound (9)
  • Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromochrysene in an amount of 4.2 g (10 mmol), 4-isopropylphenyl-p-tolyl amine in an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.4 g of pale yellow powders were obtained. The obtained product was identified to be Compound (9) in accordance with FD-MS measurement (yield: 90%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (9) is shown in FIG. 2. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (9) among the toluene solvent were 407 nm and 453 nm respectively.
    • Synthesis Example 3 Synthesis of Chemical Compound (20) (3-1) Synthesis of 2-bromo-6-isopropylnaphthalene
  • Under an atmospheric argon gas flow, trifluoromethane sulfonic acid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol), dichloro (diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5% by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into three necked-flask equipped with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to −20° C. After slowly dripping isopropylmagnesiumbromide in an amount of 90 milliliter (90 mmol, 1 mol 1 liter (tetrahydrofuran)) into the flask, the resultant solution was stirred under heating at the temperature of 80° C. for 4 hours. After the reaction terminated, adding dilute hydrochloric acid in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium bicarbonate solution and sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=90/10), and as a result, 9.4 g of aimed compound (white crystal) was obtained (yield: 33%).
    • (3-2) Synthesis of 6-isopropylnaphthalene-2-boronic acid
  • Under an atmospheric argon gas flow, 2-bromo-6-isopropylnaphthalene in an amount of 9.4 g (38 mmol), desiccated ether in an amount of 100 milliliter and desiccated toluene in an amount of 50 milliliter were placed into a three necked-flask equipped with cooling pipe and having a capacity of 500 milliliter, and then, the resultant solution was cooled down to −40° C. After slowly dripping n-butyllithium in an amount of 25 milliliter (40 mmol, 1.58M (n-hexane)) into the flask, the resultant solution was stirred at a temperature of −20° C. for 2 hours. Subsequently, the solution was cooled down to −40° C. and then, slowly dripping boronic acid triisopropylester in an amount of 26 milliliter (114 mmol), the resultant solution was stirred at the room temperature for one night. After the reaction terminated, adding dilute hydrochloric acid in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was washed with the use of 100 milliliter of toluene and as a result, 5.0 g of an aimed compound (white crystal) was obtained (yield: 63%).
    • (3-3) Synthesis of 5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde
  • Under an atmospheric argon gas flow, 2-hydroxy-5-isopropylbenzaldehyde in an amount of 4.4 g (27 mmol), trifluoromethane sulfonic acid anhydride in an amount of 11.2 g (40 mmol), pyridine in an amount of 6 milliliter (80 mmol) and dichloromethane in an amount of 100 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for 2 hours. After the reaction terminated, the resultant was separated by filtration, and after washing the resultant crude product with the use of hexane and dichloromethane, the resultant solution was vacuum dried at a temperature of 50° C. for 8 hours and as a result, 6.0 g of 2-formyl-4-isopropylphenyltrifluoromethanesulfonate (white crystal) was obtained (yield: 75%). Subsequently, under an atmospheric argon gas flow, 2-formyl-4-isopropylphenyl trifluoromethanesulfonate in an amount of 5.9 g (20 mmol), 6-isopropylnaphthalene-2-boronic acid in an amount of 4.7 g (22 mmol), (tetrakistriphenylphosphine)palladium in an amount of 1.1 g (1 mmol), 2N sodium carbonate aqueous solution in an amount of 30 milliliter and dimethoxyethane in an amount of 40 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was refluxed under heating for 8 hours. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=60/40), and as a result, 4.4 g of an aimed compound (white crystal) was obtained (yield: 70%).
    • (3-4) Synthesis of 2-isopropyl-6-(4-isopropyl-2-(2-methoxyvinyl)phenyl)naphthalene
  • Under an atmospheric argon gas flow, 5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde in an amount of 4.4 g (14 mmol), (methoxymethyl)triphenylphosphoniumchloride in an amount of 5.1 g (15 mmol), t-butoxypotassium in an amount of 1.7 g (15 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred under heating at the room temperature for one night. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=10/90), and as a result, 4.3 g of an aimed compound (white crystal) was obtained (yield: 90%).
    • (3-5) Synthesis of 2,8-diisopropyl chrysene
  • Under an atmospheric argon gas flow, 2-isopropyl-6-(4-isopropyl-2-(2-methoxy vinyl)phenyl)naphthalene in an amount of 4.3 g (12 mmol), several drops of methyl acid, and desiccated dichloromethane in an amount of 50 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred at the room temperature for 8 hours. After the reaction terminated, adding sodium bicarbonate solution in an amount of 100 milliliter into the reacted solution, crystals were separated by filtration. The resultant crude product was washed with the use of water and methanol, and then, it was vacuum dried at the temperature of 50° C. for 8 hours, and as a result, 3.5 g of an aimed compound (white crystal) was obtained (yield: 90%).
    • (3-6) Synthesis of 2,8-diisopropyl-6,12-dibromochrysene
  • Under an atmospheric argon gas flow, 2,8-diisopropyl chrysene in an amount of 3.5 g (12 mmol), N-bromosuccinimide in an amount of 5.3 g (30 mmol) and N,N-dimethylformamide in an amount of 20 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for one night. After the reaction terminated, adding water in an amount of 300 milliliter into the reacted solution, crystals were separated by filtration. The resultant crude product was washed with the use of water and methanol, and then, it was re-crystallized in 100 milliliter of toluene, and as a result, 4.7 g of an aimed compound (white crystal) was obtained (yield: 80%).
    • (3-7) Synthesis of Chemical Compound (20)
  • Under an atmospheric argon gas flow, 2,8-diisopropyl-6,12-dibromochrysene in an amount of 4.7 g (10 mmol), 4-isopropylphenyl-p-tolyl amine in an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.6 g of pale yellow powders were obtained. The obtained product was identified to be Compound (20) in accordance with FD-MS measurement (yield: 88%). Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (20) is shown in FIG. 3. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (20) among the toluene solvent were 407 nm and 450 nm respectively.
    • Synthesis Example 4 Synthesis of Compound (23) (4-1) Synthesis of 2-t-butyl-8-isopropyl-6,12-dibromo chrysene
  • An aimed compound was obtained in a similar manner as Synthesis Example 3 from the step (3-1) to the step (3-6) except that 2-hydroxy-5-t-butyl benzaldehyde was employed instead of 2-hydroxy-5-isopropyl benzaldehyde in the step (3-3).
    • (4-2) Synthesis of Compound (23)
  • Under an atmospheric argon gas flow, 2-t-butyl-8-isopropyl-6,12-dibromo chrysene in an amount of 4.8 g (10 mmol), bis(3,4-dimethylphenyl)amine in an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.9 g of pale yellow powders were obtained. The obtained product was identified to be Compound (23) in accordance with FD-MS measurement (yield: 90%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (23) is shown in FIG. 4. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (23) among the toluene solvent were 409 nm and 453 nm respectively.
    • Synthesis Example 5 Synthesis of Compound (25)
  • Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromo chrysene obtained in the step (2-1) in Synthesis Example 2 in an amount of 4.2 g (10 mmol), bis(3,4-dimethylphenyl)amine in an amount of 6.3 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine in an amount of 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.8 g of pale yellow powders were obtained. The obtained product was identified to be Compound (25) in accordance with FD-MS measurement yield: 88%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (25) is shown in FIG. 5. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (25) among the toluene solvent were 415 nm and 459 nm respectively.
    • Synthesis Example 6 Synthesis of Compound (39)
  • Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromo chrysene obtained in the step (2-1) in Synthesis Example 2 in an amount of 4.2 g (10 mmol), di(2-naphthyl)amine in an amount of 6.7 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine in an amount of 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.8 g of pale yellow powders were obtained. The obtained product was identified to be Compound (39) in accordance with FD-MS measurement yield: 85%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (39) is shown in FIG. 6. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (39) among the toluene solvent were 408 nm and 452 nm respectively.
    • Synthesis Example 7 Synthesis of Compound (57) (7-1) Synthesis of 2-t-butyl-6,12-dibromo chrysene
  • An aimed compound was obtained in a similar manner as Synthesis Example 1 from the step (1-1) to the step (1-5) except that t-butyl magnesium bromide was employed instead of methyl magnesium bromide in the step (1-1).
    • (7-2) Synthesis of Chemical Compound (57)
  • Under an atmospheric argon gas flow, 2-t-butyl-6,12-dibromochrysene in an amount of 4.4 g (10 mmol), bis(3,4-dimethylphenyl) amine in an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.6% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.5 g of pale yellow powders were obtained. The obtained product was identified to be Compound (57) in accordance with FD-MS measurement (yield: 90%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (57) is shown in FIG. 7. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (57) among the toluene solvent were 410 nm and 456 nm respectively.
    • Synthesis Example 8 Synthesis of Compound (95)
  • Under an atmospheric argon gas flow, 2-methyl-6,12-dibromo chrysene obtained in the step (1-5) in Synthesis Example 1 in an amount of 4.0 g (10 mmol), di(4-cyclohexylphenyl)amine in an amount of 8.3 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 6.3 g of pale yellow powders were obtained. The obtained product was identified to be Compound (95) in accordance with FD-MS measurement (yield: 70%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (95) is shown in FIG. 8. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (95) among the toluene solvent were 406 nm and 454 nm respectively.
    • Synthesis Example 9 Synthesis of Compound (D-973)
  • Under an atmospheric argon gas flow, 6,12-dibromochrysene in, an amount of 3.8 g (10 mmol), N-methylaniline in an amount of 2.7 g (25 mmol, palladium acetate in an amount of 0.03 g (1.6% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 2.2 g of white powders were obtained. The obtained product was identified to be Compound (D-973) in accordance with FD-MS measurement (yield: 50%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (D-973) is shown in FIG. 9. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (D-973) among the toluene solvent were 373 nm and 440 nm respectively.
    • Synthesis Example 10 Synthesis of Compound (D-974)
  • Under an atmospheric argon gas flow, 6,12-dibromochrysene in an amount of 3.8 g (10 mmol), N-isopropylaniline in an amount of 3.4 g (25 mmol, palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 2.0 g of pale yellow powders were obtained. The obtained product was identified to be Compound (C-974) in accordance with FD-MS measurement (yield: 40%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (D-974) is shown in FIG. 10. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (D-974) among the toluene solvent were 362 nm and 436 nm respectively.
    • Synthesis Example 11 Synthesis of Compound (D-998)
  • Under an atmospheric argon gas flow, 6,12-dibromochrysene in an amount of 3.8 g (10 mmol), N-(4-isopropylphenyl)pyridine-3-amine in an amount of 5.3 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 4.2 g of pale yellow powders were obtained. The obtained product was identified to be Compound (D-998) in accordance with FD-MS measurement (yield: 65%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (D-998) is shown in FIG. 11. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (D-998) among the toluene solvent were 393 nm and 444 nm respectively.
    • Synthesis Example 12 Synthesis of Compound (D-1000)
  • Under an atmospheric argon gas flow, 2-methyl-6,12-dibromochrysene in an amount of 3.9 g (10 mmol), N-(4-isopropylphenyl)pyridine-3-amine in an amount of 5.3 g (25 mmol), palladium acetate in an amount of 0.03 g (1.6% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 300 milliliter, and the resultant solution was stirred under heating at a temperature of 100° C. for one night. After the reaction terminated, precipitated crystals were separated by filtration and washed with the use of 50 milliliter of toluene and 100 milliliter of methanol, and as a result, 5.3 g of pale yellow powders were obtained. The obtained product was identified to be Compound (D-1000) in accordance with FD-MS measurement (yield: 80%).
  • Measurement by means of DRX-500 (Trade name; produced by Brucker Optics Inc.) was carried out using dimethylene chloride as a solvent and a result of 1H-NMR spectrum about the resultant Compound (D-1000) is shown in FIG. 12. Further, the maximum absorption wavelength and the maximum fluorescence wavelength of Compound (D-1000) among the toluene solvent were 385 nm and 440 nm respectively.
    • Example 1
  • A 120 nm-thick transparent electrode made of indium oxide was formed on a glass substrate having a size of 25 mm×75 mm×1.1 mm. The glass substrate with the transparent electrode was cleaned by irradiation of Ultra Violet ray and ozone. The thus cleaned glass substrate with the transparent electrode was mounted to a vacuum vapor deposition apparatus.
  • First, N′,N″-bis[4-(diphenylamino)phenyl]-N′,N″-diphenylbiphenyl-4,4′-diamine was vapor-deposited to form a hole injecting layer having a thickness of 60 nm, and then N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-bendizine was vapor deposited on the hole injecting layer to form a hole transporting layer having a thickness of 20 nm. Then, 10,10′-bis[1,1′,4′,1″]terphenyl-2-yl-9,9′-bianthracenyl and the above Compound (9) were simultaneously vapor deposited at a weight ratio of 40:2 on the hole transporting layer to form a light emitting layer having a thickness of 40 nm.
  • Next, tris(8-hydroxyquinolinato)aluminum was vapor-deposited on the light emitting layer to form an electron injecting layer having a thickness of 10 nm. Then, tris(8-hydroxyquinolinato)aluminum and lithium was vapor-deposited at a weight ratio of 10:0.3 on the electron injecting layer to form a layer having a thickness of 10 nm, and further aluminum was vapor-deposited thereon to form an aluminum layer having a thickness of 150 nm. The aluminum layer functioned as a cathode. Thus, an organic EL device was fabricated.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 602 cd/m2 (peak wavelength of light emission: 464 nm) and current efficiency of 6.0 cd/A was emitted at a voltage of 6.0 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 18900 hours.
    • Example 2
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that Compound (9) was replaced with Compound (23).
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 664 cd/m2 (peak wavelength of light emission: 462 nm) and current efficiency of 6.6 cd/A was emitted at a voltage of 6.5 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 16000 hours.
    • Example 3
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that 10,10′-bis[1,1′,4′,1′]terphenyl-2-yl-9,9′-bianthracenyl was replaced with 10-(3-(naphthalen-1-yl)phenyl)-9-(naphthalen-2-yl)anthracene.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 631 cd/m2 (peak wavelength of light emission: 464 nm) and current efficiency of 6.3 cd/A was emitted at a voltage of 6.5 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 20000 hours or longer.
    • Example 4
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (23) for the doping material.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 710 cd/m2 (peak wavelength of light emission: 465 nm) and current efficiency of 7.1 cd/A was emitted at a voltage of 6.5 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 20000 hours or longer.
    • Example 5
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (25) for the doping material.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 793 cd/m2 (peak wavelength of light emission: 469 nm) and current efficiency of 7.9 cd/A was emitted at a voltage of 6.5 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 20000 hours or longer.
    • Example 6
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 3 except that Compound (9) was replaced with Compound (10) for the doping material.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 782 cd/m2 (peak wavelength of light emission: 468 nm) and current efficiency of 7.8 cd/A was emitted at a voltage of 6.5 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 20000 hours or longer.
    • Comparative Example 1
  • An organic EL device was fabricated in accordance with the same procedures as those conducted in Example 1 except that Compound (9) was replaced with 6,12-bis(4-isopropylphenyl-p-tolylamino)chrysene.
  • As a result of subjecting the thus obtained organic EL device to a test by passing electric current, it was confirmed that a blue light with a luminance of 594 cd/m2 (peak wavelength of light emission: 462 nm) and current efficiency of 5.9 cd/A was emitted at a voltage of 6.3 V and a current density of 10 mA/cm2. Further, as a result of subjecting the device to a continuous test by passing DC electric current starting at an initial luminance of 500 cd/m2, it was confirmed that the half lifetime thereof was 4590 hour.
  • From the above-mentioned result, it is apparent that when any substituent does not bond to diaminochrysene backbone structure, half lifetime shortens because of an association between compounds each other.
    • INDUSTRIAL APPLICABILITY
  • The organic EL device using the aromatic amine derivative according to the present invention can exhibit a practically sufficient luminance of light emission even upon applying a low voltage thereto, and has an enhanced efficiency of light emission and the device is free from deterioration in properties even after being used for a long period of time and, therefore, has a long lifetime. Resultantly, the EL device is useful as a flat panel light emitting member for a wall-hanging type television or as a light source of backlight and the like for display devices.

Claims (6)

1. An aromatic amine derivative represented by the following general formula (2):
Figure US20090189522A1-20090730-C04552
wherein A5 to A8 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms; R5 to R8 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylamino group having 5 to 20 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms; and a couple of R5 and R6, and a couple of R7 and R8 may bond each other to form a saturated or unsaturated ring.
2. An organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrodes consisting of an anode and a cathode, wherein one or more of the at least one organic thin film layer comprises the aromatic amine derivative according to claim 1 singly or in mixture.
3. The organic electroluminescence device according to claim 2, wherein the light emitting layer comprises the aromatic amine derivative singly or in mixture.
4. The organic electroluminescence device according to claim 2, wherein the light emitting layer comprises the aromatic amine derivative in an amount of 0.1 to 20% by weight.
5. The organic electroluminescence device according to claim 2, wherein said device emits bluish light.
6. A doping material comprising the aromatic amine derivative according to claim 1.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130062598A1 (en) * 2011-09-12 2013-03-14 Hakan Usta Compounds Having Semiconducting Properties and Related Compositions and Devices
KR20160052526A (en) * 2013-09-06 2016-05-12 이데미쓰 고산 가부시키가이샤 Anthracene derivative and organic electroluminescent element using same

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1219747C (en) * 1998-12-28 2005-09-21 出光兴产株式会社 Organic electroluminescent device
CN100343359C (en) * 2002-11-12 2007-10-17 出光兴产株式会社 Material for organic electroluminescent device and organic electroluminescent device using the same
TW200536924A (en) * 2004-05-12 2005-11-16 Idemitsu Kosan Co 1,6-substituted 3,8-dihalogenopyrene and process for producing the same
WO2006025273A1 (en) 2004-08-31 2006-03-09 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
WO2006030527A1 (en) * 2004-09-17 2006-03-23 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
DE602006018864D1 (en) * 2005-02-07 2011-01-27 Idemitsu Kosan Co AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THIS
JP4263700B2 (en) * 2005-03-15 2009-05-13 出光興産株式会社 Aromatic amine derivative and organic electroluminescence device using the same
JP2007137837A (en) * 2005-11-21 2007-06-07 Idemitsu Kosan Co Ltd Aromatic amine derivative and organic electroluminescent element using the same
JP5145717B2 (en) * 2006-04-13 2013-02-20 東ソー株式会社 Benzofluorene compounds and uses thereof
US8993805B2 (en) 2006-04-13 2015-03-31 Tosoh Corporation Benzofluorene compound and use thereof
KR20090035693A (en) * 2006-08-04 2009-04-10 이데미쓰 고산 가부시키가이샤 Organic electroluminescent device material and organic electroluminescent device using the same
US8115378B2 (en) * 2006-12-28 2012-02-14 E. I. Du Pont De Nemours And Company Tetra-substituted chrysenes for luminescent applications
US8465848B2 (en) * 2006-12-29 2013-06-18 E I Du Pont De Nemours And Company Benzofluorenes for luminescent applications
JP5439711B2 (en) * 2007-01-26 2014-03-12 東ソー株式会社 Benzofluorene compounds and uses thereof
US20080303428A1 (en) * 2007-06-01 2008-12-11 Vsevolod Rostovtsev Chrysenes for green luminescent applications
KR20100025544A (en) * 2007-06-01 2010-03-09 이 아이 듀폰 디 네모아 앤드 캄파니 Chrysenes for blue luminescent applications
ATE536340T1 (en) * 2007-06-01 2011-12-15 Du Pont BLUE LUMINESCENT MATERIALS
JP5466150B2 (en) 2007-06-01 2014-04-09 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Green light emitting material
KR101554750B1 (en) 2007-06-01 2015-09-22 이 아이 듀폰 디 네모아 앤드 캄파니 Chrysenes for deep blue luminescent applications
WO2009084585A1 (en) * 2007-12-28 2009-07-09 Idemitsu Kosan Co., Ltd. Aromatic diamine derivative and organic electroluminescent device using the same
US8546844B2 (en) 2008-06-26 2013-10-01 E I Du Pont De Nemours And Company Process for forming an organic light-emitting diode luminaires having a single light-emitting layer with at least two light-emitting dopants
CN102132436A (en) * 2008-08-29 2011-07-20 出光兴产株式会社 Compound for organic thin film transistor and organic thin film transistor using same
JP5335379B2 (en) * 2008-11-12 2013-11-06 学校法人東海大学 Organic semiconductor material and organic electronic device using the same
KR101495396B1 (en) 2008-11-19 2015-02-24 이 아이 듀폰 디 네모아 앤드 캄파니 Chrysene compounds for blue or green luminescent applications
US20110037056A1 (en) * 2008-12-12 2011-02-17 E. I. Du Pont De Nemours And Company Photoactive composition and electronic device made with the composition
US8263973B2 (en) 2008-12-19 2012-09-11 E I Du Pont De Nemours And Company Anthracene compounds for luminescent applications
US8932733B2 (en) 2008-12-19 2015-01-13 E I Du Pont De Nemours And Company Chrysene derivative host materials
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
TWI387394B (en) * 2009-03-04 2013-02-21 Chung Shan Inst Of Science Organic light emitting diode and method for manufacturing the same
KR20170134775A (en) * 2009-03-13 2017-12-06 미쯔비시 케미컬 주식회사 Process for manufacturing organic electroluminescent element, organic electroluminescent element, organic el display, and organic el lighting
KR101582707B1 (en) 2009-04-03 2016-01-05 이 아이 듀폰 디 네모아 앤드 캄파니 Electroactive materials
TW201040132A (en) * 2009-05-07 2010-11-16 Du Pont Deuterated compounds for luminescent applications
CN102428159A (en) * 2009-05-19 2012-04-25 E.I.内穆尔杜邦公司 Chrysene Compounds For Luminescent Applications
EP2449054A4 (en) * 2009-07-01 2013-05-29 Du Pont Chrysene compounds for luminescent applications
CN102834483B (en) 2009-08-13 2015-07-15 E.I.内穆尔杜邦公司 Chrysene derivative materials
KR20120055713A (en) * 2009-08-24 2012-05-31 이 아이 듀폰 디 네모아 앤드 캄파니 Organic light-emitting diode luminaires
KR20120066025A (en) * 2009-08-24 2012-06-21 이 아이 듀폰 디 네모아 앤드 캄파니 Organic light-emitting diode luminaires
WO2011028482A2 (en) * 2009-08-24 2011-03-10 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
US20110204337A1 (en) * 2009-08-24 2011-08-25 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
CN102484217A (en) * 2009-08-24 2012-05-30 E.I.内穆尔杜邦公司 Organic light-emitting diode luminaires
CN102484215A (en) * 2009-08-24 2012-05-30 E.I.内穆尔杜邦公司 Organic light-emitting diode luminaires
WO2011040939A1 (en) 2009-09-29 2011-04-07 E. I. Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8716700B2 (en) * 2009-10-29 2014-05-06 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
EP2493887A4 (en) 2009-10-29 2013-06-19 Du Pont Deuterated compounds for electronic applications
US8716699B2 (en) * 2009-10-29 2014-05-06 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
US8674343B2 (en) 2009-10-29 2014-03-18 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
WO2011059789A2 (en) * 2009-10-29 2011-05-19 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
EP2510071A4 (en) * 2009-12-09 2013-12-18 Du Pont Deuterated compound as part of a combination of compounds for electronic applications
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
JP5644147B2 (en) * 2010-03-17 2014-12-24 三菱化学株式会社 Organic compound, organic electroluminescent element material, composition for organic electroluminescent element, organic electroluminescent element, organic EL display device, and organic EL lighting
KR101758328B1 (en) 2010-04-06 2017-07-17 삼성디스플레이 주식회사 Heterocyclic compound and organic light emitting device comprising the same
KR101736987B1 (en) 2010-04-06 2017-05-18 삼성디스플레이 주식회사 Heterocyclic compound and organic light emitting device comprising the same
KR101810045B1 (en) 2010-10-25 2017-12-19 삼성디스플레이 주식회사 Heterocyclic compound and Organic light emitting device containing same
US8455867B2 (en) 2010-10-26 2013-06-04 Samsung Display Co., Ltd. Organic light-emitting device
JP5727038B2 (en) 2010-12-20 2015-06-03 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ Compositions for electronic technology applications
WO2012162818A1 (en) * 2011-06-03 2012-12-06 Queen's University At Kingston Substituted diarylamines and use of same as antioxidants
KR102138351B1 (en) * 2011-08-18 2020-07-28 이데미쓰 고산 가부시키가이샤 Biscarbazole derivative and organic electroluminescence element using same
KR101918953B1 (en) * 2012-03-06 2018-11-16 삼성디스플레이 주식회사 Amine-based compound, organic light emitting diode comprising the same and organic light emitting apparatus comprising the same
KR102050484B1 (en) 2013-03-04 2019-12-02 삼성디스플레이 주식회사 Anthracene derivatives and organic light emitting diodes comprising the derivatives
KR102107106B1 (en) 2013-05-09 2020-05-07 삼성디스플레이 주식회사 Styryl-based compound and organic light emitting diode comprising the same
KR102269131B1 (en) 2013-07-01 2021-06-25 삼성디스플레이 주식회사 Compound and organic light emitting device comprising same
EP3054459B1 (en) * 2013-10-04 2018-07-11 ONES (Organic Nano Electronic System) Co., LTD Electrode having excellent light transmittance and method for manufacturing same
US10062850B2 (en) 2013-12-12 2018-08-28 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
KR20160100961A (en) 2013-12-20 2016-08-24 바스프 에스이 Highly efficient oled devices with very short decay times
KR20150132795A (en) 2014-05-16 2015-11-26 삼성디스플레이 주식회사 Organic light emitting device
KR102343145B1 (en) 2015-01-12 2021-12-27 삼성디스플레이 주식회사 Condensed compound and organic light-emitting device comprising the same
US20180182980A1 (en) 2015-06-03 2018-06-28 Udc Ireland Limited Highly efficient oled devices with very short decay times
JP6913079B2 (en) 2016-03-29 2021-08-04 住友化学株式会社 Light emitting element
US11225602B2 (en) 2016-06-24 2022-01-18 Sumitomo Chemical Company, Limited Light emitting device

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030072966A1 (en) * 1998-12-28 2003-04-17 Idemitsu Kosan Co., Ltd. Organic electrolumescence device
US20030082404A1 (en) * 2001-08-29 2003-05-01 Fujitsu Limited Condensed eight-ring aromatic compound, and organic EL element and organic EL display using the same
US6747287B1 (en) * 2001-10-18 2004-06-08 Nec Corporation Organic thin film transistor
US20050064233A1 (en) * 2002-07-19 2005-03-24 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and organic light emitting medium
US20050107430A1 (en) * 2003-10-29 2005-05-19 Banik Bimal K. Antimicrobial and antiviral compounds
US20060194074A1 (en) * 2005-02-07 2006-08-31 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US20070236137A1 (en) * 2006-03-03 2007-10-11 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US7405326B2 (en) * 2005-08-08 2008-07-29 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and electroluminescence device using the same
US7425653B2 (en) * 2004-08-31 2008-09-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device employing the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4117093B2 (en) * 1998-12-28 2008-07-09 出光興産株式会社 Material for organic electroluminescence device and organic electroluminescence device using the same
CN100343359C (en) * 2002-11-12 2007-10-17 出光兴产株式会社 Material for organic electroluminescent device and organic electroluminescent device using the same

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030072966A1 (en) * 1998-12-28 2003-04-17 Idemitsu Kosan Co., Ltd. Organic electrolumescence device
US20050038296A1 (en) * 1998-12-28 2005-02-17 Idemitsu Kosan Co., Ltd. Organic electrolumescence device
US20030082404A1 (en) * 2001-08-29 2003-05-01 Fujitsu Limited Condensed eight-ring aromatic compound, and organic EL element and organic EL display using the same
US6747287B1 (en) * 2001-10-18 2004-06-08 Nec Corporation Organic thin film transistor
US20050064233A1 (en) * 2002-07-19 2005-03-24 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and organic light emitting medium
US20050107430A1 (en) * 2003-10-29 2005-05-19 Banik Bimal K. Antimicrobial and antiviral compounds
US7425653B2 (en) * 2004-08-31 2008-09-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device employing the same
US7524568B2 (en) * 2004-08-31 2009-04-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device employing the same
US20060194074A1 (en) * 2005-02-07 2006-08-31 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US7405326B2 (en) * 2005-08-08 2008-07-29 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and electroluminescence device using the same
US20070236137A1 (en) * 2006-03-03 2007-10-11 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US7642380B2 (en) * 2006-03-03 2010-01-05 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130062598A1 (en) * 2011-09-12 2013-03-14 Hakan Usta Compounds Having Semiconducting Properties and Related Compositions and Devices
KR20160052526A (en) * 2013-09-06 2016-05-12 이데미쓰 고산 가부시키가이샤 Anthracene derivative and organic electroluminescent element using same
KR102342399B1 (en) * 2013-09-06 2021-12-22 이데미쓰 고산 가부시키가이샤 Anthracene derivative and organic electroluminescent element using same

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