|Publication number||US3837851 A|
|Publication date||24 Sep 1974|
|Filing date||15 Jan 1973|
|Priority date||15 Jan 1973|
|Also published as||CA1005674A1, DE2401219A1, DE2401219B2, DE2401219C3|
|Publication number||US 3837851 A, US 3837851A, US-A-3837851, US3837851 A, US3837851A|
|Inventors||Shattuck M, Weiche W|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (9), Referenced by (120), Classifications (14)|
|External Links: USPTO, USPTO Assignment, Espacenet|
United States Patent 11 1 Shattuck et a1.
1 1 Sept. 24, 1974 1 PHOTOCONDUCTOR OVERCOAT ED WITH TRIARYLPYRAZOLINE CHARGE TRANSPORT LAYER  Inventors: Meredith David Shattuck, San Jose;
William Joseph Weiche, Los Gatos, both of Calif.
 Assignee: International Business Machines Corporation, Armonk, NY.
 Filed: Jan. 15, 1973  Appl. No.: 323,677
52 0.5. Ci 96/1.5, 96/1.6, 252/501, 117/215,117/218 51 1111. C1. G03g s/04, 003 5/06, 003 5/08 3,549,362 12/1970 Carpenter et a1 96/1.6 3,598,582 8/1971 Herrick et al 1 96/1.5 3,684,548 8/1972 Contois 96/1.6 X
FOREIGN PATENTS OR APPLICATIONS 4,326,710 11/1968 Japan 96/1.6 1,030,024 5/1966 Great Britain 96/1.5
Primary ExaminerR0land E. Martin, Jr. Attorney, Agent, or Firm-J0seph G. Walsh  ABSTRACT Electrophotographic plates are provided having a charge generation layer and a separate charge transport layer comprising a tri-aryl pyrazoline compound having the formula:
wherein n is Zero or one, and A, A and A are each aryl radicals.
4 Claims, No Drawings PHOTOCONDUCTOR OVERCOATED WITH TRIARYLPYRAZOLINE CHARGE TRANSPORT LAYER FIELD OF THE INVENTION The present invention is concerned with layered electrophotographic plates. In particular it is concerned with electrophotographic plates having a charge generating layer and a separate charge transporting layer. According to the present invention, the charge transporting layer always comprises at least one tri-aryl pyrazoline compound having the formula:
wherein n is zero or one, and A, A and A are each aryl radicals.
PRIOR ART The pyrazoline compounds useful in the present invention are known materials and their preparation has been described in the literature. The prior art teaches that such materials are known to be photoconductors. The photoconductive nature of pyrazolines is taught in U.S. Pat. Nos. 3,180,729 and 3,549,362.
SUMMARY OF THE INVENTION It has now been found that electrophotographic plates having unexpected advantages can be prepared using certain pyrazoline compounds in a charge transport layer which is used in conjunction with a separate charge generating layer.
the pyrazoline compounds useful in the present invention are those having the formula wherein n is zero or one, and A, A and A are each aryl radicals.
In this formula it is preferred that n l, in which case the materials may be classified chemically as styryl pyrazolines. It is also preferred that one or more of the aryl groups be substituted, most preferably with groups known in the art to be electron donating groups. The most preferred substituent groups are methoxy, ethoxy, dimethyl amino, diethyl amino an the like. It is not preferred to substitute the aryl groups with electron withdrawing groups such as nitro and cyano.
There are several well known electrophotographic reproduction processes in current use. They differ in the particular way in which they are carried out, particularly in the sequence in which electric charging (usually with a corona) and illumination are carried out. All electrophotographic reproduction processes, however, involve the process step.of selectively rendering portions of a photoconductor electrically conductive by selective exposure to light. The charge transport layers of the present invention are useful in making electrophotographic plates useful in all such processes.
It is one of the unexpected advantages of the present invention that the charge transport layers may be used with any of a wide variety of separate charge generating layers. For example, the charge generating layer may be selenium or an alloy of selenium. It may be other inorganic materials such as compounds from groups II and VI of the periodic table, for example cadmium sulfo-selenide. Alternatively, the charge generating material may be an organic material, for example a cyanine compound such as those shown in US. Pat. application Ser. No. 129,637, a disazo compound such as those shown in U.S. Pat. application Ser. No. 129,635, now abandoned, or a phthalocyanine compound. Particularly outstanding results have been obtained when the charge generating layer comprises a compound which is a methine dye derived from squaric acid. Materials of this type are discussed in U.S. Pat. application Ser. No. 323,678 filed on even date herewith.
The charge transport layers of the present invention may be used either on top of the charge generating layer, or beneath the charge generating layer. For mechanical reasons, it is generally preferred that the charge transport layer be on top. The charge transport layer may vary considerably in thickness, in general being from about 10 to about 30 microns thick, preferably from about 15 to about 25. When the charge transport layer is on top of the charge generating layer, i.e. when the charge generating layer is between the charge transport layer and the conductive substrate, the electrophotographic plate should be charged negatively. In those instances where the charge transport layer is beneath the charge generating layer, that is, when the charge transport layer is between the charge generating layer and the conductive substrate, the electrophotographic plate should be charged positively. The theoretical explanation for this is not known with certainty. It is theorized that the pyrazoline charge transport layers of the present invention operate by transporting holes, and this explanation would be consistent with those data.
Photoconductivity involves at least two steps: (1 the generation of charge, and (2) the transportation of charge. The present invention utilizes the ability of the pyrazoline containing layer to transport the charge generated in the separate charge generating layer. Among the unexpected advantages of the present invention, it should be particularly mentioned that the pyrazoline containing materials have the unexpected ability not only to transport the charge, but also to accept injection of the charge, that is, to allow the charge to cross the interface between the separate charge generating layer and the charge transport layer. This is true with both organic and inorganic charge generation layers.
The pyrazoline compounds of the present invention have the additional advantage of being film forming. They may, therefore, be used by themselves to form the charge transport layer. For mechanical reasons, however, it is generally preferred to use them in conjunction with a binder. In most instances it is preferred to use roughly from about 1 part to about 3 parts by weight binder to one part by weight pyrazoline. Many types of binder materials such as resins are known to the prior art. Particularly good results have been obtained using polyester resins and polycarbonates. Polyvinylidene chloride and polystyrene may also be used, as may acrylic resins of low molecular weight.
The following Examples are given solely for purposes of illustration and are not to be considered limitations on the invention, many variations of which are possible without departing from the spirit or scope thereof.
EXAMPLE 1 A charge generating layer consisting of 68% Se, 30% Te, and 2% As (weight percent) evaporated on a conductive substrate which was dip coated with a barrier layer with a dry thickness of approximately 0.3 microns. The barrier layer was coated with a solution of 3 parts polyester (Goodyear VPE 200) and 1 part lphenyl-3-[p-dimethylaminostyryl]-5-[p-dimethylaminophenyl]pyrazoline which had been dissolved in tetrahydrofuran. Method of coating was knife blade with a wet gap setting of 5 mils. The composite layer was heated 16 hours at 55 C with a resulting dry thickness of 15 microns.
The photoconductor was corona charged in the dark to a negative voltage of approximately 700 volts. The sample was then exposed to a light source of a photocopy green lamp. The initial dark charge was reduced to 200 V with an exposure of 0.33 micro joules/cm? EXAMPLE 2 A solution prepared from tetrahydrofuran and consisting of 3 parts of polyester and 1 part pyrazoline (as in Example No. 1) was knife blade coated at a wet thickness of 5 mils on a conductive substrate. The layer was dried for 2 hours at approximately 80C to remove excess solvent. Dry thickness was approximately 12 microns. The photoconductor was charged on a rotating disc electrometer to a negative voltage of 600 volts. Exposure to a tungsten source reduced the dark charge to 500 Volts (approximately 20 percent decay) after 4.0 seconds. By comparison, the layered photoconductor from Example No. l was dark charged on the rotating disc electrometer to a negative voltage of 880 V and exposed to the tungsten source plus a 1.47 neutral density filter plus opal glass. The original dark charge of 880 was reduced 20 percent after 0.15 sec. (70X increase) and to a 200 volt level in 0.7 seconds.
EXAMPLE 3 Approximately 1 gram of a cyanine dye, 3-ethyl-2[5- '(3-ethyl-2-benzothiazolinylidene )-l ,S-pentadienyl] benzothiazolium iodide was placed in a McCrone micronizing mill (a vibro-energy laboratory mill available from McCrone Research Associates, London, England) and was ground as a dry powder for 60 minutes. Approximately grams of tetrahydrofuran and 0. 15 g of a polyvinylbutyral resin Vinylite XYHL (available from Union Carbide and Carbon Company) was added to the powder and was ground for an additional 30 minutes. The resultant slurry was reduced in concentration by additional tetrahydrofuran and was applied to an volts. The sample was exposed to a tungsten light source filtered with wavelength filters to give maximum intensity at approximately 5.500 angstroms. The initial dark voltage of 700 volts was reduced to 200 volts by an exposure of approximately 07 micro joules/cm".
EXAMPLE 4 A selenium alloy charge generating layer was prepared in the same manner as Example No. I The layer was dip coated with a solution of one part polyester and one part l-phenyl-3-[p-methoxystyryl]-5-[p'methoxy phenyll-pyrazoline dissolved in tetrahydrofuran. The coating was dried for 40 hours at C to remove excess solvent with a resulting dry thickness of 16 to 18 microns.
The photoconductive plate was negatively charged in the dark to approximately 700 volts. The plate was then exposed to a photocopy green lamp. The initial dark charge was reduced to 200 volts with an exposure of 0.32 micro joules/cm? EXAMPLE 5 A selenium alloy charge generating layer was prepared in the same manner as Example No. l. The layer was dip coated with a solution of two parts polyester and one part l-phenyl-3-[p-diethylaminostyryl]-5-[pdiethylaminophenyl]-pyrazoline dissolved in tetrahydrofuran. The coating was dried for 72 hours at C to remove excess solvent with a resulting dry thickness of 15 microns.
The photoconductor was corona charged in the dark to a negative charge of 700 volts and then was exposed to a photo-copy green lamp. The initial dark charge was reduced to 200 volts with an exposure of 0.24 micro joules/cm? EXAMPLE 6 A charge generating layer consisting of a Se alloy was evaporated directly onto a conductive substrate. A charge transport layer was formulated and coated in the same manner as Example No. 5.
The photoconductor was corona charged in the dark to a negative voltage of approximately 600 volts. The plate was then exposed to a photocopy green light source and the dark charge reduced to 200 volts with an exposure of 0.24 micro joules/cm? EXAMPLE 7 A charge generating layer consisting of Cd S Se approximately 0.3 microns thick was coated on a conductive substrate by a chemical vapor deposition technique. A charge transport layer consisting of 3 parts polyester and one part l-phenyl-3-[ pdimethylaminostyry] ]-5 -[p-dimethylamino phenyl]- pyrazoline was knife coated to a dry thickness of approximately six microns.
The photoconductor was dark charged on a rotating disc electrometer to a negative charge of 390 volts. The sample was exposed to a tungsten source with the initial dark charge being reduced to 200 volts in 0.15 sec.
EXAMPLE 8 A charge transport layer consisting of two parts polyester and one part l-phenyl-3[p-diethylaminostyryl1- S-[p-diethylamino phenyH-pyrazoline was dissolved in a suitable solvent. The solution was dip coated in a conductive substrate and dried to an approximate thickness of microns. A charge generating layer consisting of 2-p-dimethylaminostyrylquinoline ethiodide dye was rubbed onto the surface of the transport layer (thickness, less than 2 microns).
The photoconductor was then positively charged on a rotating disk electrometer to a dark charge of 720 volts. The initial dark charge was decayed with a tungsten lamp to 200 volts in 0.80 seconds.
EXAMPLE 9 A second charge transport layer prepared in the same manner as in Example No. 7 was coated with a thin dye layer of pyrazlone red.
The photoconductor was positively charged to a dark voltage of 920 volts on the rotating disc electrometer. The initial dark voltage was then reduced with a tungsten exposure source to 200 volts in 0.70 seconds.
What is claimed is:
1. An electrophotographic process comprising the steps of negatively charging and image-wise exposing to light an electrophotographic plate comprising a conductive substrate, a layer comprising a photoconductor selected from the group consisting of selenium and its alloys, compounds of an element from Group II and an element from Group VI of the periodic table, cyanine compounds, disazo compounds, and phthalocyanine compounds, and, overcoating said layer of photoconductor, a separate layer from 10 to 30 microns thick comprising a compound having the formula:
|Cited Patent||Filing date||Publication date||Applicant||Title|
|US3180729 *||18 Dec 1957||27 Apr 1965||Azoplate Corp||Material for electrophotographic reproduction|
|US3384488 *||21 Jul 1967||21 May 1968||Xcrox Corp||Polychromatic photoelectrophoretic imaging composition|
|US3527602 *||31 Aug 1967||8 Sep 1970||Eastman Kodak Co||Organic photoconductors|
|US3535221 *||17 Oct 1967||20 Oct 1970||Xerox Corp||Photoelectrophoretic imaging system employing a photoconductor coating for the blocking electrode|
|US3549362 *||12 Apr 1968||22 Dec 1970||Eastman Kodak Co||Novel cyanine dyes for the sensitization of organic photoconductors|
|US3598582 *||18 Sep 1967||10 Aug 1971||Ibm||Photoconductive element exhibiting photoconductive dichroism and process of using same|
|US3684548 *||30 Jun 1970||15 Aug 1972||Contois Lawrence E||Method of preparing a homogeneous dye-sensitized electrophotographic element|
|GB1030024A *||Title not available|
|JP43026710A *||Title not available|
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US3964904 *||22 Aug 1974||22 Jun 1976||Xerox Corporation||Manifold imaging member and process employing a dark charge injecting layer|
|US3977870 *||29 May 1975||31 Aug 1976||Hoechst Aktiengesellschaft||Dual layer electrophotographic recording material|
|US3989520 *||20 May 1975||2 Nov 1976||Hoechst Aktiengesellschaft||Electrophotographic dual layer recording material|
|US3996049 *||15 May 1975||7 Dec 1976||Hoechst Aktiengesellschaft||Dual layer electrophotographic recording material|
|US4012251 *||22 May 1975||15 Mar 1977||Xerox Corporation||Multi-layered photoconductive member|
|US4030923 *||11 Dec 1975||21 Jun 1977||International Business Machines Corporation||Mixture of binder materials for use in connection with a charge transport layer in a photoconductor|
|US4066455 *||5 Nov 1975||3 Jan 1978||Eastman Kodak Company||Selenium containing multi-active photoconductive element|
|US4090782 *||31 May 1977||23 May 1978||International Business Machines Corporation||Electrochromic display devices comprising thienylidene pyrazoline compounds|
|US4093358 *||27 Dec 1976||6 Jun 1978||International Business Machines Corporation||High efficiency electrochromic display device|
|US4123270 *||12 Jan 1976||31 Oct 1978||International Business Machines Corporation||Method of making electrophotographic imaging element|
|US4142783 *||31 May 1977||6 Mar 1979||International Business Machines Corporation||Reversible electrochromic display device having memory|
|US4164431 *||18 May 1978||14 Aug 1979||Eastman Kodak Company||Multilayer organic photovoltaic elements|
|US4231799 *||15 May 1975||4 Nov 1980||Hoechst Aktiengesellschaft||Electrophotographic recording material|
|US4247614 *||16 Nov 1979||27 Jan 1981||Ricoh Co., Ltd.||Electrophotographic element containing a disazo pigment|
|US4251614 *||30 Jun 1978||17 Feb 1981||Ricoh Company, Ltd.||Novel disazo compounds, process for the preparation of same and application of said disazo compounds and analogues thereof to electrophotographic sensitive materials|
|US4268596 *||21 Nov 1979||19 May 1981||Ricoh Company, Ltd.||Electrophotographic element having 1,4-bis(azostyryl)-2,5 dimethoxy benzene compounds as photoconductors|
|US4278746 *||14 Jun 1979||14 Jul 1981||Konishiroku Photo Industry Co., Ltd.||Photosensitive elements for electrophotography|
|US4279981 *||18 Apr 1978||21 Jul 1981||Ricoh Company, Ltd.||Electrophotographic elements containing trisazo compounds|
|US4281053 *||7 Feb 1980||28 Jul 1981||Eastman Kodak Company||Multilayer organic photovoltaic elements|
|US4293628 *||26 Jan 1978||6 Oct 1981||Ricoh Co., Ltd.||Electrophotographic elements containing disazo compounds|
|US4299896 *||17 Jul 1978||10 Nov 1981||Ricoh Co., Ltd.||Electrophotographic sensitive materials containing a disazo pigment|
|US4302521 *||15 Jul 1980||24 Nov 1981||Konishiroku Photo Industry Co., Ltd.||Photosensitive element for electrophotography|
|US4307167 *||3 Mar 1980||22 Dec 1981||International Business Machines Corporation||Layered electrophotographic plate having tetramethyl benzidene based disazo dye|
|US4314015 *||19 Dec 1980||2 Feb 1982||Ricoh Co., Ltd.||Electrophotographic sensitive materials containing disazo compounds|
|US4314016 *||11 Jun 1980||2 Feb 1982||Ricoh Co., Ltd.||Electrophotographic element having a bisazo photoconductor|
|US4315982 *||24 Feb 1981||16 Feb 1982||Copyer Co., Ltd.||Styryl pyrazoline compounds, process for production thereof, and electrophoto graphic material comprising said compounds|
|US4348470 *||4 Dec 1979||7 Sep 1982||Ricoh Co., Ltd.||Electrophotographic element containing disazo compounds|
|US4349617 *||23 Oct 1980||14 Sep 1982||Fuji Photo Film Co., Ltd.||Function separated type electrophotographic light-sensitive members and process for production thereof|
|US4362798 *||18 May 1981||7 Dec 1982||International Business Machines Corporation||Hydrazone and pyrazoline or acetosol yellow containing charge transport layer, photoconductor and electrophotographic process using the same|
|US4363859 *||13 Oct 1978||14 Dec 1982||Ricoh Company, Ltd.||Electrophotographic photoconductor|
|US4369242 *||5 Aug 1981||18 Jan 1983||Minnesota Mining And Manufacturing Company||Non-porous and porous Al2 O3 barrier zones in layered electrophotographic device|
|US4399207 *||22 Jul 1982||16 Aug 1983||Canon Kabushiki Kaisha||Electrophotographic photosensitive member with hydrazone compound|
|US4413045 *||24 May 1982||1 Nov 1983||Canon Kabushiki Kaisha||Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer|
|US4418133 *||4 Mar 1982||29 Nov 1983||Canon Kabushiki Kaisha||Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer|
|US4423129 *||30 Nov 1981||27 Dec 1983||Canon Kabushiki Kaisha||Electrophotographic member having layer containing methylidenyl hydrazone compound|
|US4446217 *||27 Jan 1982||1 May 1984||Canon Kabushiki Kaisha||Electrophotographic photosensitive member having a hydrazone containing layer|
|US4454211 *||1 Jun 1982||12 Jun 1984||Canon Kabushiki Kaisha||Electrophotographic photosensitive member with pyrazoline charge transport material|
|US4456671 *||13 Dec 1982||26 Jun 1984||Canon Kabushiki Kaisha||Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound|
|US4487824 *||9 May 1983||11 Dec 1984||Canon Kabushiki Kaisha||Electrophotographic photosensitive member containing a halogen substituted hydrazone|
|US4543310 *||20 Jan 1983||24 Sep 1985||Oce-Nederland B.V.||Electrophotographic element and photocopying process making use of certain 4-[bis-phenylamino]benzaldehyde azines|
|US4554231 *||9 Dec 1983||19 Nov 1985||Canon Kabushiki Kaisha||Electrophotographic photosensitive member|
|US4567125 *||6 Dec 1983||28 Jan 1986||Hoechst Aktiengesellschaft||Electrophotographic recording material|
|US4588667 *||15 May 1984||13 May 1986||Xerox Corporation||Electrophotographic imaging member and process comprising sputtering titanium on substrate|
|US4762760 *||29 Jan 1987||9 Aug 1988||Hoechst Aktiengesellschaft||Electrophotographic recording material comprising a pyrazoline derivative|
|US4769304 *||27 Apr 1982||6 Sep 1988||Fuji Photo Film Co., Ltd.||Photoconductive composition and electro-photographic light-sensitive material using said composition|
|US4883731 *||4 Jan 1988||28 Nov 1989||Xerox Corporation||Imaging system|
|US4931371 *||21 Nov 1988||5 Jun 1990||Canon Kabushiki Kaisha||Electrophotographic photosensitive member|
|US5032479 *||15 Jun 1989||16 Jul 1991||Kao Corporation||Ion transport photoreceptor for electrophotography|
|US5079118 *||19 Jan 1990||7 Jan 1992||Canon Kabushiki Kaisha||Photosensitive member for electrophotography with substituted pyrene|
|US5116709 *||13 Jun 1989||26 May 1992||Industrial Technology Research Institute||Electrophotoreceptor using styrene-maleic anhydride copolymer as the polymeric binder|
|US5120628 *||12 Dec 1989||9 Jun 1992||Xerox Corporation||Transparent photoreceptor overcoatings|
|US5215842 *||8 Jan 1991||1 Jun 1993||Hitachi, Ltd.||Photosensitive element for electrophotography|
|US5262261 *||16 Sep 1992||16 Nov 1993||Canon Kabushiki Kaisha||Photosensitive member for electrophotography|
|US5324608 *||23 Nov 1992||28 Jun 1994||Mitsubishi Kasei America, Inc.||Photoconductor drum, having a non-conductive layer, with an area of electrical contact and method of manufacturing the same|
|US5466550 *||25 Oct 1994||14 Nov 1995||Canon Kabushiki Kaisha||Electrophotographic photosensitive member and electrophotographic apparatus, device unit and facsimile machine using the same|
|US5554473 *||23 Nov 1994||10 Sep 1996||Mitsubishi Chemical America, Inc.||Photoreceptor having charge transport layers containing a copolycarbonate and layer containing same|
|US5876888 *||2 Jul 1997||2 Mar 1999||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, and apparatus and process cartridge provided with the same|
|US5876890 *||23 May 1997||2 Mar 1999||Canon Kabushiki Kaisha||Electrophotographic photosensitive member and apparatus and process cartridge provided with the same|
|US5935747 *||5 Jun 1997||10 Aug 1999||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, and process cartridge and electrophotographic apparatus having the electrophotographic photosensitive member|
|US5952142 *||31 Jul 1998||14 Sep 1999||Oce-Technologies, B.V.||Azine-containing photoconductive element|
|US6017665 *||26 Feb 1998||25 Jan 2000||Mitsubishi Chemical America||Charge generation layers and charge transport layers and organic photoconductive imaging receptors containing the same, and method for preparing the same|
|US6093515 *||27 Aug 1998||25 Jul 2000||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus|
|US6146800 *||16 Oct 1998||14 Nov 2000||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus|
|US6180302||27 Oct 1998||30 Jan 2001||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, and process cartridge and electrophotographic apparatus provided with the electrophotographic member|
|US6405005||31 Jul 2000||11 Jun 2002||Canon Kabushiki Kaisha||Process cartridge and electrophotographic apparatus|
|US6410195||7 Aug 2000||25 Jun 2002||Canon Kabushiki Kaisha||Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus|
|US6703174||30 Jan 2002||9 Mar 2004||Canon Kabushiki Kaisha||Electrophotographic apparatus and process cartridge|
|US7361440||9 Aug 2005||22 Apr 2008||Xerox Corporation||Anticurl backing layer for electrostatographic imaging members|
|US7422831||15 Sep 2005||9 Sep 2008||Xerox Corporation||Anticurl back coating layer electrophotographic imaging members|
|US7455941||21 Dec 2005||25 Nov 2008||Xerox Corporation||Imaging member with multilayer anti-curl back coating|
|US7462434||21 Dec 2005||9 Dec 2008||Xerox Corporation||Imaging member with low surface energy polymer in anti-curl back coating layer|
|US7504187||28 Jul 2006||17 Mar 2009||Xerox Corporation||Mechanically robust imaging member overcoat|
|US7517624||27 Dec 2005||14 Apr 2009||Xerox Corporation||Imaging member|
|US7524597||22 Jun 2006||28 Apr 2009||Xerox Corporation||Imaging member having nano-sized phase separation in various layers|
|US7527906||20 Jun 2006||5 May 2009||Xerox Corporation||Imaging member having adjustable friction anticurl back coating|
|US7541123||20 Jun 2005||2 Jun 2009||Xerox Corporation||Imaging member|
|US7582399||22 Jun 2006||1 Sep 2009||Xerox Corporation||Imaging member having nano polymeric gel particles in various layers|
|US7642028||15 Sep 2005||5 Jan 2010||Xerox Corporation||Imaging members|
|US7704658||15 Jul 2009||27 Apr 2010||Xerox Corporation||Imaging member having nano polymeric gel particles in various layers|
|US7754404||27 Dec 2005||13 Jul 2010||Xerox Corporation||Imaging member|
|US7767373||23 Aug 2006||3 Aug 2010||Xerox Corporation||Imaging member having high molecular weight binder|
|US7943278||7 Apr 2008||17 May 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US7998646||7 Apr 2008||16 Aug 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US8003285||31 Aug 2009||23 Aug 2011||Xerox Corporation||Flexible imaging member belts|
|US8007970||7 Apr 2008||30 Aug 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US8021812||7 Apr 2008||20 Sep 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US8026028||7 Apr 2008||27 Sep 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US8084173||7 Apr 2008||27 Dec 2011||Xerox Corporation||Low friction electrostatographic imaging member|
|US8124305||1 May 2009||28 Feb 2012||Xerox Corporation||Flexible imaging members without anticurl layer|
|US8168356||1 May 2009||1 May 2012||Xerox Corporation||Structurally simplified flexible imaging members|
|US8173341||1 May 2009||8 May 2012||Xerox Corporation||Flexible imaging members without anticurl layer|
|US8232030||17 Mar 2010||31 Jul 2012||Xerox Corporation||Curl-free imaging members with a slippery surface|
|US8232032||29 Mar 2011||31 Jul 2012||Xerox Corporation||Low friction electrostatographic imaging member|
|US8241825||31 Aug 2009||14 Aug 2012||Xerox Corporation||Flexible imaging member belts|
|US8263298||24 Feb 2011||11 Sep 2012||Xerox Corporation||Electrically tunable and stable imaging members|
|US8263301||14 Jun 2011||11 Sep 2012||Xerox Corporation||Low friction electrostatographic imaging member|
|US8268457||5 Dec 2008||18 Sep 2012||Idemitsu Kosan Co., Ltd.||Organic electroluminescent device and material for organic electroluminescent device|
|US8278017||2 Oct 2012||Xerox Corporation||Crack resistant imaging member preparation and processing method|
|US8343700||16 Apr 2010||1 Jan 2013||Xerox Corporation||Imaging members having stress/strain free layers|
|US8394560||25 Jun 2010||12 Mar 2013||Xerox Corporation||Imaging members having an enhanced charge blocking layer|
|US8404413||18 May 2010||26 Mar 2013||Xerox Corporation||Flexible imaging members having stress-free imaging layer(s)|
|US8465892||18 Mar 2011||18 Jun 2013||Xerox Corporation||Chemically resistive and lubricated overcoat|
|US8470505||10 Jun 2010||25 Jun 2013||Xerox Corporation||Imaging members having improved imaging layers|
|US8475983||30 Jun 2010||2 Jul 2013||Xerox Corporation||Imaging members having a chemical resistive overcoat layer|
|US8541151||19 Apr 2010||24 Sep 2013||Xerox Corporation||Imaging members having a novel slippery overcoat layer|
|US8877413||23 Aug 2011||4 Nov 2014||Xerox Corporation||Flexible imaging members comprising improved ground strip|
|US9017907||11 Jul 2013||28 Apr 2015||Xerox Corporation||Flexible imaging members having externally plasticized imaging layer(s)|
|US9017908||20 Aug 2013||28 Apr 2015||Xerox Corporation||Photoelectrical stable imaging members|
|US9046798||16 Aug 2013||2 Jun 2015||Xerox Corporation||Imaging members having electrically and mechanically tuned imaging layers|
|US9075327||20 Sep 2013||7 Jul 2015||Xerox Corporation||Imaging members and methods for making the same|
|US9091949||16 Aug 2013||28 Jul 2015||Xerox Corporation||Imaging members having electrically and mechanically tuned imaging layers|
|DE2717007A1 *||18 Apr 1977||20 Oct 1977||Ricoh Kk||3-(9-fluorenyliden)-carbazolderivate, verfahren zu ihrer herstellung und ihre verwendung in elektrophotographischen lichtempfindlichen materialien|
|DE3730258A1 *||9 Sep 1987||7 Apr 1988||Canon Kk||Elektrophotographisches lichtempfindliches aufzeichnungsmaterial, 5h-dibenzo(a,d)cycloheptanylidenderivat, 5h-dibenzo(a,d)cycloheptenylidenderivat und verfahren zu ihrer herstellung|
|EP0001599A1 *||6 Oct 1978||2 May 1979||International Business Machines Corporation||Electrophotographic recording material and its application in a copying process|
|EP0096989A2 *||25 May 1983||28 Dec 1983||Toray Industries, Inc.||Electrophotographic photosensitive material|
|EP1515191A2||27 Aug 2004||16 Mar 2005||Xerox Corporation||Dual charge transport layer and photoconductive imaging member including the same|
|EP2253998A1||11 May 2010||24 Nov 2010||Xerox Corporation||Flexible imaging members having a plasticized imaging layer|
|EP2290449A1||18 Aug 2010||2 Mar 2011||Xerox Corporation||Flexible imaging member belts|
|EP2290450A1||18 Aug 2010||2 Mar 2011||Xerox Corporation||Flexible imaging member belts|
|WO2007038425A2 *||26 Sep 2006||5 Apr 2007||David M Ferguson||Anti-viral compouinds|
|U.S. Classification||430/58.55, 252/501.1|
|International Classification||G03G5/06, C09K3/16, G03G5/043, G03G5/047|
|Cooperative Classification||G03G5/047, G03G5/0631, G03G5/067, G03G5/0436|
|European Classification||G03G5/043D, G03G5/06D2D4, G03G5/06H2B2, G03G5/047|