US3824099A - Sensitive electrophotographic plates - Google Patents

Sensitive electrophotographic plates Download PDF

Info

Publication number
US3824099A
US3824099A US00323678A US32367873A US3824099A US 3824099 A US3824099 A US 3824099A US 00323678 A US00323678 A US 00323678A US 32367873 A US32367873 A US 32367873A US 3824099 A US3824099 A US 3824099A
Authority
US
United States
Prior art keywords
charge
layer
transport layer
squaric acid
electrophotographic plates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00323678A
Inventor
R Champ
M Shattuck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IBM Information Products Corp
Original Assignee
International Business Machines Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by International Business Machines Corp filed Critical International Business Machines Corp
Priority to US00323678A priority Critical patent/US3824099A/en
Priority to FR7345362A priority patent/FR2214138B1/fr
Priority to GB49074A priority patent/GB1441996A/en
Priority to DE2401220A priority patent/DE2401220A1/en
Priority to JP49006088A priority patent/JPS524188B2/ja
Application granted granted Critical
Publication of US3824099A publication Critical patent/US3824099A/en
Assigned to IBM INFORMATION PRODUCTS CORPORATION, 55 RAILROAD AVENUE, GREENWICH, CT 06830 A CORP OF DE reassignment IBM INFORMATION PRODUCTS CORPORATION, 55 RAILROAD AVENUE, GREENWICH, CT 06830 A CORP OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: INTERNATIONAL BUSINESS MACHINES CORPORATION
Assigned to MORGAN BANK reassignment MORGAN BANK SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IBM INFORMATION PRODUCTS CORPORATION
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • G03G5/0611—Squaric acid
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms

Definitions

  • Very sensitive electrophotographic plates having a charge generating layer comprising a squaric acid methine dye and a charge transport layer comprising a tri-aryl pyrazoline compound.
  • the present invention is concerned with electrophotographic plates.
  • it is concerned with layered plates having a charge generation layer and a separate charge transport layer.
  • the charge generation layer comprises a squaric acid methine dye and the charge transport layer comprises a tri-aryl pyrazoline compound. Electrophotographic plates containing these layers have been found to be extremely sensitive to light.
  • Squaric Acid methine dyes are known compounds which have been described in the literature. 1,3- and 1,2-squaric acid methine dyes, both of which are useful in the present invention, have been described, for example, in US. Pat. 3,617,270 where methods for their synthesis are also described. That patent discloses the use of squaric acid methine dyes for the optical sensitization of zinc oxide, in which use the squaric acid methine dye is used at a concentration of about 0.1 to 20 milligrams per square meter of finished photoconductive layer.
  • the electrophotographic plates of the present invention comprise, in addition to a conductive substrate, a charge generating layer containing a squaric acid methine dye and a separate charge transport layer containing a tri-aryl pyrazoline compound.
  • Electrophotographic plates having the structure recited above have been found to be extremely fast in their response to light. They are panchromatic out to about 7000 Angstrom units. They are also responsive to light having wave lengths up to 9000 Angstroms. A particularly suitable field for their use is with lasers having wave lengths of from about 8000 to about 9000 Angstrorns.
  • the electrophotographic plates contain both squaric acid charge generating material and tri-aryl pyrazoline charge transporting material. Both are essential elements of the present invention. This result was totally unexpected and the theoretical explanation for it is not known.
  • electrophotographic reproduction processes there are several well known electrophotographic reproduction processes in current use. They differ in the particular way in which they are carried out, particularly United States Patent 0 ice 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 electrophotographic plates of the present invention are useful in all such processes.
  • the charge transport layer 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.
  • 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 squaric acid methine dye maybe used alone, but it is preferred to use a squaric acid methine dye in conjunction with a binder when the layer is formed by coating from a slurry.
  • the optimum ratio of dye to binder is generally from about 0.1 to about 0.9.
  • Binderless layers may be formed by vacuum evaporation. Many types of binder materials, such as resins, are known to the prior art. Many polyesters are suitable materials. Sucrose benzoate may also be employed in many mixtures of the various, binders. Particularly outstanding results have been obtained using polyvinyl butyral.
  • the charge generating layer be from about 0.1 to about 2 microns thick, most preferably about 0.5 microns. It is also preferred that the charge generating layer contain from approximately 50 to about 100 milligrams of the squaric acid methine dye per square meter of plate area.
  • the following squarylium pigments were all ground to a fine particle size in tetrahydrofuran and applied by a knife blade coater on aluminized Mylar substrate.
  • Mylar is a trade name for polyethyleneterephthalate film from Dupont.
  • the coating percent solids is 3% and the wet gap setting is one mil.
  • a transport layer of 2 parts Merlon 60 and 1 part DEASP by weight Coating thickness is 13-15 microns thick.
  • Merlon 60 is a trade name for a polycarbonate resin marketed by Mobay Chemicals.
  • DEASP is a shortened abbreviation for 1-Phenyl-3-[pdiethylaminostyryH-S [p-diethylamino phenyl]-pyrazoline.
  • the coated films are then heated for 30 minutes electrometer.
  • the illumination was from a tungsten halogen lamp, watts, 28 volts at a distance of approximately .5 cm.
  • HO- OH l CH3 HI E- A is the amount of energy required to decay the photoconductor by exposure to light to one-half its charge acceptance.
  • the percent solids is 15.5 and the coating speed is 8 f.p.m.
  • the fihn is treated for 15 minutes at 115 C.
  • EXAMPLE 12 When the formulation of Example 9 is coated on aluminized Mylar which has been subbed with a coating of 0.3;]. of an acrylic resin (A-11 from Roehm and Haas) the following sensitometric data are noted:
  • EXAMPLE 13 The charge generating layer was prepared by evaporating the compound in Example 11 on an aluminized Mylar substrate to an optical density to green light of 0.4.
  • An electrophotographic plate comprising a conductive substrate, a layer comprising a squaric acid methine dye and a separate layer comprising a tri-aryl pyrazoline compound.

Abstract

VERY SENSITIVE ELECTROPHOTOGRAPHIC PLATES ARE PROVIDED HAVING A CHARGE GENERATING LAYER COMPRISING A SQUARIC ACID METHINE DYE AND A CHARGE TRANSPORT LAYER COMPRISING A TRI-ARYL PYRAZOLINE COMPOUND.

Description

3,824,099 SENSITIVE ELECTROPHOTOGRAPHIC PLATES Robert Bruce Champ and Meredith David Shattuck, San
Jose, Calif., assignors to International Business Machines Corporation, Armonk, N .Y. No Drawing. Filed Jan. 15, 1973, Ser. No. 323,678 Int. 'Cl. G03c 5/06 US. CI. 96-15 4 Claims ABSTRACT OF THE DISCLOSURE Very sensitive electrophotographic plates are provided having a charge generating layer comprising a squaric acid methine dye and a charge transport layer comprising a tri-aryl pyrazoline compound.
FIELD OF THE INVENTION The present invention is concerned with electrophotographic plates. In particular, it is concerned with layered plates having a charge generation layer and a separate charge transport layer. The charge generation layer comprises a squaric acid methine dye and the charge transport layer comprises a tri-aryl pyrazoline compound. Electrophotographic plates containing these layers have been found to be extremely sensitive to light.
PRIOR ART Squaric Acid methine dyes are known compounds which have been described in the literature. 1,3- and 1,2-squaric acid methine dyes, both of which are useful in the present invention, have been described, for example, in US. Pat. 3,617,270 where methods for their synthesis are also described. That patent discloses the use of squaric acid methine dyes for the optical sensitization of zinc oxide, in which use the squaric acid methine dye is used at a concentration of about 0.1 to 20 milligrams per square meter of finished photoconductive layer.
SUMMARY OF THE INVENTION The electrophotographic plates of the present invention comprise, in addition to a conductive substrate, a charge generating layer containing a squaric acid methine dye and a separate charge transport layer containing a tri-aryl pyrazoline compound. Electrophotographic plates having the structure recited above have been found to be extremely fast in their response to light. They are panchromatic out to about 7000 Angstrom units. They are also responsive to light having wave lengths up to 9000 Angstroms. A particularly suitable field for their use is with lasers having wave lengths of from about 8000 to about 9000 Angstrorns.
To obtain the high sensitivities of the present invention it is necessary that the electrophotographic plates contain both squaric acid charge generating material and tri-aryl pyrazoline charge transporting material. Both are essential elements of the present invention. This result was totally unexpected and the theoretical explanation for it is not known.
The use of tri-aryl pyrazoline containing charge transport layers is disclosed in US. Patent Application Ser. No. 323,677, filed on even date herewith.
There are several well known electrophotographic reproduction processes in current use. They differ in the particular way in which they are carried out, particularly United States Patent 0 ice 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 electrophotographic plates of the present invention are useful in all such processes.
In the electrophotographic plates of the present invention, the charge transport layer 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.
In forming the charge generating layers of the present invention, the squaric acid methine dye maybe used alone, but it is preferred to use a squaric acid methine dye in conjunction with a binder when the layer is formed by coating from a slurry. The optimum ratio of dye to binder, depending upon the particular dye, is generally from about 0.1 to about 0.9. Binderless layers may be formed by vacuum evaporation. Many types of binder materials, such as resins, are known to the prior art. Many polyesters are suitable materials. Sucrose benzoate may also be employed in many mixtures of the various, binders. Particularly outstanding results have been obtained using polyvinyl butyral. In general, it is preferred that the charge generating layer be from about 0.1 to about 2 microns thick, most preferably about 0.5 microns. It is also preferred that the charge generating layer contain from approximately 50 to about 100 milligrams of the squaric acid methine dye per square meter of plate area.
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.
EXAMPLES l.-8
The following squarylium pigments were all ground to a fine particle size in tetrahydrofuran and applied by a knife blade coater on aluminized Mylar substrate. (Mylar is a trade name for polyethyleneterephthalate film from Dupont.) The coating percent solids is 3% and the wet gap setting is one mil. Over this generation layer is then coated a transport layer of 2 parts Merlon 60 and 1 part DEASP by weight. Coating thickness is 13-15 microns thick. Merlon 60 is a trade name for a polycarbonate resin marketed by Mobay Chemicals. DEASP is a shortened abbreviation for 1-Phenyl-3-[pdiethylaminostyryH-S [p-diethylamino phenyl]-pyrazoline. The coated films are then heated for 30 minutes electrometer. The illumination was from a tungsten halogen lamp, watts, 28 volts at a distance of approximately .5 cm.
Light decay E Charge (mlcrojoules/ acceptance Example number Pigment cmfl) (volts) OH Et Et Et Et 580 a on 0H -Q 0H H Me Me N +2 N Me Me OH OH 0 2.2 670 6..--:--.-.: OH OH OH OH on. on 0 on OH:
HO- OH l CH3 HI E- A; is the amount of energy required to decay the photoconductor by exposure to light to one-half its charge acceptance.
EXAMPLE 9 One gram of the compound CH; 0- CH3 CH3 /CH; J K
is ground in a McCrone micronizing mill for minutes whereupon 3 g. of 5% polyvinylbutyral (XYHL B-800 from Union Carbide) is added with 7 g. of tetrahydrofuran. The material is micronized for 20 minutes and then decanted into a jar. Seven grams of a 5% Elvacite 4.05 g. Merlon 60 2.7 g. DEASP.
8 d.p.s. 10% DC-200 (Dow Corning Silicon Oil) in tetrahydroforan.
The percent solids is 15.5 and the coating speed is 8 f.p.m. The fihn is treated for 15 minutes at 115 C.
Sensitometry on the above film gave the following data:
Dark Decay v./Sec 40 volts/sec. E from 700 v. charge [Photocopy green lamps (PCG)] 0.95 microjoules/cmF. Dark Charge with 650 Volts on Screen 780 v.
EXAMPLE 10 When the compound O CH3 1 CH3 @GK (JR/3 3 OH:
is employed in the above formulation and coated to an optical density of 0.2 to green light the following sensitometric results are obtained:
Dark Decay Volts/sec. 220 volts/sec. E from 700 v. charge (PCG) 0.58 microjoules/cmF. Dark charge with 780 v. on
Screen 800 v.
EXAMPLE 11 When the compound OH O- OH is employed in the formulation as described in Example 9 and coated to an optical density of 0.6 to .green light the following sensitometric results are obtained:
Dark Decay Volts/sec. 16 volts/sec. E from 700 v. charge (PCG) 0.74 microjoules/cmF. Dark charge with 720 v. on
screen 780 v.
EXAMPLE 12 When the formulation of Example 9 is coated on aluminized Mylar which has been subbed with a coating of 0.3;]. of an acrylic resin (A-11 from Roehm and Haas) the following sensitometric data are noted:
Dark Decay v./sec. v./sec. E from 700 v. charge PCG) 1.1microjoules/cmfi. Dark charge with 680 v. on
screen 750.
EXAMPLE 13 The charge generating layer was prepared by evaporating the compound in Example 11 on an aluminized Mylar substrate to an optical density to green light of 0.4.
This was coated with a transport layer consisting of:
Parts Polyester (Vitel PE-200 from Goodyear) 2 DEASP 1 The percent solids is 20 in tetrahydrofuran and the coating speed is about 8 f.p.m. The film was dried to remove excess solvent at C. for 30 minutes.
Sensitometry on the above film is as follows:
Dark Charge 700 v. Energy required to decay to 200 v. (Photocopy green lamp) 0.4 microjoules/cmf".
References Cited UNITED STATES PATENTS 3,617,270 11/1971 Kampfer 96-l.7 3,527,602 9/1970 Fox 961.5 3,634,135 1/1972 Osaka 961.5
FOREIGN PATENTS 4,326,710 11/1968 Japan 961.6
RONALD H. SMITH, Primary Examiner J. L. GOODROW, Assistant Examiner US. Cl. X.R. 961.8, 1.6
. UNITED STATES PATENT OFFICE 1 CERTIFICATE OF CRRECTION Patent no. 3,824,099 Dated Julv 16,4374
Inventor(3) Robert Bruce Champ et al It is certified that error appears in the above idantitied patent and that said Letters Patent hereby untreated as shown aalowz r' In the Claims, Claim 1 should read as follows:
1. An electrophotographic plate comprising a conductive substrate, a layer comprising a squaric acid methine dye and a separate layer comprising a tri-aryl pyrazoline compound.
Signed and sealed this 22nd day of October 1974.
(SEAL) Attest:
McCOY M. GIBSON JR. C. MARSHALL DANN Attesting Officer Commissioner of Patents
US00323678A 1973-01-15 1973-01-15 Sensitive electrophotographic plates Expired - Lifetime US3824099A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US00323678A US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates
FR7345362A FR2214138B1 (en) 1973-01-15 1973-12-11
GB49074A GB1441996A (en) 1973-01-15 1974-01-04 Layered electrophotographic elements
DE2401220A DE2401220A1 (en) 1973-01-15 1974-01-11 ELECTROPHOTOGRAPHIC PLATE
JP49006088A JPS524188B2 (en) 1973-01-15 1974-01-11

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00323678A US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates

Publications (1)

Publication Number Publication Date
US3824099A true US3824099A (en) 1974-07-16

Family

ID=23260256

Family Applications (1)

Application Number Title Priority Date Filing Date
US00323678A Expired - Lifetime US3824099A (en) 1973-01-15 1973-01-15 Sensitive electrophotographic plates

Country Status (4)

Country Link
US (1) US3824099A (en)
JP (1) JPS524188B2 (en)
DE (1) DE2401220A1 (en)
FR (1) FR2214138B1 (en)

Cited By (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3964904A (en) * 1974-08-22 1976-06-22 Xerox Corporation Manifold imaging member and process employing a dark charge injecting layer
US4030923A (en) * 1975-12-11 1977-06-21 International Business Machines Corporation Mixture of binder materials for use in connection with a charge transport layer in a photoconductor
US4052209A (en) * 1975-03-07 1977-10-04 Minnesota Mining And Manufacturing Company Semiconductive and sensitized photoconductive compositions
US4090782A (en) * 1977-05-31 1978-05-23 International Business Machines Corporation Electrochromic display devices comprising thienylidene pyrazoline compounds
US4093358A (en) * 1976-12-27 1978-06-06 International Business Machines Corporation High efficiency electrochromic display device
US4123270A (en) * 1975-09-15 1978-10-31 International Business Machines Corporation Method of making electrophotographic imaging element
US4142783A (en) * 1977-05-31 1979-03-06 International Business Machines Corporation Reversible electrochromic display device having memory
US4175956A (en) * 1978-02-10 1979-11-27 Eastman Kodak Company Electrophotosensitive materials for migration imaging processes
US4307167A (en) * 1980-03-03 1981-12-22 International Business Machines Corporation Layered electrophotographic plate having tetramethyl benzidene based disazo dye
US4314016A (en) * 1979-06-20 1982-02-02 Ricoh Co., Ltd. Electrophotographic element having a bisazo photoconductor
US4363859A (en) * 1977-10-22 1982-12-14 Ricoh Company, Ltd. Electrophotographic photoconductor
US4381337A (en) * 1981-11-23 1983-04-26 Pitney Bowes Inc. Polyester adhesive layer for photosensitive elements
US4389475A (en) * 1981-03-20 1983-06-21 Basf Aktiengesellschaft Multilayered electrophotographic recording medium
US4413045A (en) * 1981-05-26 1983-11-01 Canon Kabushiki Kaisha Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer
US4418133A (en) * 1981-03-27 1983-11-29 Canon Kabushiki Kaisha Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer
US4423129A (en) * 1980-12-17 1983-12-27 Canon Kabushiki Kaisha Electrophotographic member having layer containing methylidenyl hydrazone compound
US4446217A (en) * 1981-02-03 1984-05-01 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a hydrazone containing layer
US4456671A (en) * 1981-12-23 1984-06-26 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound
US4471041A (en) * 1983-05-09 1984-09-11 Xerox Corporation Photoconductive devices containing novel squaraine compositions
US4481272A (en) * 1981-03-20 1984-11-06 Basf Aktiengesellschaft Layered electrophotographic recording medium comprising heterocyclic nitrogen containing organic dye compounds
US4481270A (en) * 1983-04-28 1984-11-06 Ricoh Systems, Inc. Photoreceptor containing squaric acid methine dyes
US4486520A (en) * 1983-12-05 1984-12-04 Xerox Corporation Photoconductive devices containing novel squaraine compositions
US4487824A (en) * 1982-05-17 1984-12-11 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a halogen substituted hydrazone
US4500621A (en) * 1983-04-11 1985-02-19 Ricoh Systems, Inc. Sensitive electrophotographic plates containing squaric acid methine dyes suspended in a binder
US4507480A (en) * 1983-05-09 1985-03-26 Xerox Corporation Squaraines
US4508803A (en) * 1983-12-05 1985-04-02 Xerox Corporation Photoconductive devices containing novel benzyl fluorinated squaraine compositions
US4508811A (en) * 1983-01-17 1985-04-02 U.S. Philips Corporation Recording element having a pyrylium or thiopyrylium-squarylium dye layer and new pyrylium or thiopyrylium-squarylium compounds
US4523035A (en) * 1983-12-05 1985-06-11 Xerox Corporation Process for synthesizing squaraine compositions
US4524218A (en) * 1984-01-11 1985-06-18 Xerox Corporation Processes for the preparation of squaraine compositions
EP0146301A1 (en) * 1983-12-05 1985-06-26 Xerox Corporation Process for synthesizing squaraine compositions
US4543310A (en) * 1982-01-29 1985-09-24 Oce-Nederland B.V. Electrophotographic element and photocopying process making use of certain 4-[bis-phenylamino]benzaldehyde azines
US4559286A (en) * 1984-09-13 1985-12-17 Xerox Corporation Mixed squaraine photoconductive compositions
US4600673A (en) * 1983-08-04 1986-07-15 Minnesota Mining And Manufacturing Company Silicone release coatings for efficient toner transfer
US4606986A (en) * 1983-12-05 1986-08-19 Xerox Corporation Electrophotographic elements containing unsymmetrical squaraines
US4626485A (en) * 1984-05-11 1986-12-02 Fuji Xerox Co., Ltd. Substituted squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same
US4677045A (en) * 1984-07-27 1987-06-30 International Business Machines Corporation Squarylium charge generating dye and electrophotographic photoconductor
US4820846A (en) * 1982-07-29 1989-04-11 Minnesota Mining And Manufacturing Company Triarylmethane compounds, their preparation and use as photoconductive systems
US4830786A (en) * 1986-02-27 1989-05-16 Syntex (U.S.A.) Inc. Squaraine dyes
US5130217A (en) * 1991-09-17 1992-07-14 Lexmark International, Inc. Squarylium photoconductors with noncrystalline bisphenol a binders
US5270139A (en) * 1992-07-02 1993-12-14 Industrial Technology Research Institute Photoconductor comprising bisazo and squarylium pigments as the charge generation material
US5310922A (en) * 1986-02-27 1994-05-10 Syntex (U.S.A.) Inc. Squaraine dyes
US5338636A (en) * 1991-09-27 1994-08-16 Fuji Xerox Co., Ltd. Dichlorotin phthalocyanine crystal electrophotographic photoreceptor using the same, and coating composition for electrophotographic photoreceptor
US5486439A (en) * 1993-02-09 1996-01-23 Canon Kabushiki Kaisha Electrophotographic with polycarbonate having charge transporting group
US5488601A (en) * 1992-10-26 1996-01-30 Dai Nippon Printing Co., Ltd. Photoelectric sensor, information recording system, and information recording method
US5510218A (en) * 1993-07-09 1996-04-23 Canon Kabushiki Kaisha Electrophotographic photosensitive member, process cartridge using same and electrophotographic apparatus
US5621130A (en) * 1993-10-22 1997-04-15 Canon Kabushiki Kaisha Electrophotographic photosensitive member, eletrophotographic apparatus and apparatus unit including the photosensitive member
US5935755A (en) * 1995-08-21 1999-08-10 Xerox Corporation Method for document marking and recognition
US5952142A (en) * 1997-07-31 1999-09-14 Oce-Technologies, B.V. Azine-containing photoconductive element
WO2000053552A1 (en) * 1999-03-05 2000-09-14 Mitsubishi Chemical Corporation Squarylium compounds, filters for plasma display panels made by using the same, and plasma display panels
US6225015B1 (en) 1998-06-04 2001-05-01 Mitsubishi Paper Mills Ltd. Oxytitanium phthalocyanine process for the production thereof and electrophotographic photoreceptor to which the oxytitanium phthalocyanine is applied
US20040101770A1 (en) * 2002-09-04 2004-05-27 Sharp Kabushiki Kaisha Organic photoconductive material, electrophotographic photoreceptor comprising the same, and image-forming apparatus
US20050164107A1 (en) * 2003-11-19 2005-07-28 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus provided with the same
US20050232657A1 (en) * 2004-01-29 2005-10-20 Sharp Kabushiki Kaisha Image forming apparatus
US20050238973A1 (en) * 2004-03-30 2005-10-27 Sharp Kabushiki Kaisha Amine compound, electrophotographic photoreceptor using the amine compound and image forming apparatus having the same
US20050238972A1 (en) * 2003-12-01 2005-10-27 Sharp Kabushiki Kaisha Amine compound, manufacturing method thereof, electrophotographic photoreceptor using amine compound and image forming apparatus having the same
JP2006031030A (en) * 2005-07-22 2006-02-02 Kyowa Hakko Kogyo Co Ltd Synthetic resin molding
US20060057481A1 (en) * 2004-09-07 2006-03-16 Akihiro Kondoh Hydrazone compound, electrophotographic photoreceptor comprising the hydrazone compound, and image forming apparatus equipped with the electrophotographic photoreceptor
US20060160812A1 (en) * 2003-07-03 2006-07-20 The Salk Institute For Biological Studies Methods for treating neural disorders and conditions, and compounds useful therefor
US20060210895A1 (en) * 2003-06-03 2006-09-21 Takatsugu Obata Photosensitive material for electrophotography and image forming device having the same
US20060215805A1 (en) * 2003-08-13 2006-09-28 Louis Aerts Sealing device for the outer surface of a nuclear fuel cladding
US20060275683A1 (en) * 2005-06-01 2006-12-07 Sharp Kabushiki Kaisha Asymmetric bis-hydroxyenamine compound, electrophotographic photoreceptor and image forming apparatus
US20070026334A1 (en) * 2003-02-07 2007-02-01 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus including the same
US20070077506A1 (en) * 2003-10-08 2007-04-05 Akiki Kihara Electrophotographic photoreceptor and image forming apparatus provided with the same
US20070281229A1 (en) * 2006-06-02 2007-12-06 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus
US20110104600A1 (en) * 2009-10-29 2011-05-05 Kurauchi Takahiro Electrophotographic photoconductor and image forming apparatus using the same
US20120248419A1 (en) * 2011-02-09 2012-10-04 Mark Thompson Organic photosensitive devices comprising aryl squaraines and methods of making the same
US8465890B2 (en) 2010-08-30 2013-06-18 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus including the same, and coating solution for undercoat layer formation in electrophotographic photoconductor
US8546049B2 (en) 2010-12-21 2013-10-01 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus using the same
US8568946B2 (en) 2009-03-19 2013-10-29 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image formation device comprising same
US10651390B2 (en) 2016-06-08 2020-05-12 Ricoh Company, Ltd. Tertiary amine compound, photoelectric conversion element, and solar cell

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5358813A (en) * 1902-01-13 1994-10-25 Fuji Xerox Co., Ltd. Crystals of chlorogallium phthalocyanine and method of preparing them
US4548886A (en) * 1982-06-08 1985-10-22 Canon Kabushiki Kaisha Radiation sensitive organic thin film comprising an azulenium salt
JP2541030B2 (en) * 1991-04-22 1996-10-09 富士ゼロックス株式会社 Novel crystal of hydroxyindium phthalocyanine and electrophotographic photoreceptor using the same
US5393629A (en) * 1991-04-26 1995-02-28 Fuji Xerox Co., Ltd. Electrophotographic photoreceptor
JP3166293B2 (en) * 1991-04-26 2001-05-14 富士ゼロックス株式会社 Novel hydroxygallium phthalocyanine crystal, photoconductive material comprising the new crystal, and electrophotographic photoreceptor using the same
US5283145A (en) * 1991-05-01 1994-02-01 Fuji Xerox Co., Ltd. Crystals of dichlorotin phthalocyanine, method of preparing the crystal, and electrophotographic photoreceptor comprising the crystal
US5308728A (en) * 1991-08-16 1994-05-03 Fuji Xerox Co., Ltd. Dichlorotin phthalocyanine crystal, process for producing the same, and electrophotographic photoreceptor using the same
JP3166283B2 (en) * 1992-03-31 2001-05-14 富士ゼロックス株式会社 Method for producing novel crystals of hydroxygallium phthalocyanine
JPH07102183A (en) * 1993-10-01 1995-04-18 Fuji Xerox Co Ltd Gallium halide phthalocyanine crystal, its production and electrophotographic photoreceptor using the same
JP2814872B2 (en) * 1993-03-25 1998-10-27 富士ゼロックス株式会社 Hydroxygallium phthalocyanine crystal, method for producing the same, and electrophotographic photoreceptor using the same
JP3072689B2 (en) * 1993-04-02 2000-07-31 富士ゼロックス株式会社 Methoxygallium phthalocyanine compound and electrophotographic photoreceptor using the same
JP2882977B2 (en) * 1993-08-12 1999-04-19 富士ゼロックス株式会社 Method for producing hydroxygallium phthalocyanine crystal and electrophotographic photoreceptor using the same
JP3158831B2 (en) * 1994-01-11 2001-04-23 富士電機株式会社 Metal-free phthalocyanine, its production method and electrophotographic photoreceptor
JP3216426B2 (en) * 1994-06-06 2001-10-09 富士ゼロックス株式会社 Hydroxygallium phthalocyanine crystal and electrophotographic photoreceptor using the same
JPH08120190A (en) * 1994-08-31 1996-05-14 Fuji Xerox Co Ltd Production of chlorogallium phthalocyanine crystal
JP3060199B2 (en) * 1994-09-30 2000-07-10 富士ゼロックス株式会社 Method for producing hydroxygallium phthalocyanine crystal
JPH08209023A (en) 1994-11-24 1996-08-13 Fuji Electric Co Ltd Titaniloxyphthalocyanine crystal, its production and photosensitizer for electrophotography
JP3635786B2 (en) * 1996-01-17 2005-04-06 富士ゼロックス株式会社 Electrophotographic photoreceptor
US5958637A (en) * 1996-07-24 1999-09-28 Hitachi Chemical Company, Ltd. Electrophotographic photoreceptor and coating solution for production of charge transport layer
JP5147032B2 (en) * 2001-04-03 2013-02-20 株式会社林原 Cyanine dye
EP1997855A3 (en) 2002-07-29 2010-09-08 Mitsubishi Paper Mills Limited Organic dye, photoelectric transducing material, semiconductor electrode, and photoelectric transducing device
WO2008023489A1 (en) * 2006-08-21 2008-02-28 National Institute Of Advanced Industrial Science And Technology Squaric acid derivative compound, protein detection reagent comprising the compound, and protein detection method using the reagent
WO2010016612A1 (en) 2008-08-06 2010-02-11 三菱製紙株式会社 Dye for dye-sensitized solar cell, semiconductor electrode, and dye-sensitized solar cell
KR20150077290A (en) 2013-12-27 2015-07-07 삼성전자주식회사 Asymmetric butadiene-based charge transporting compounds, and electrophotographic photoreceptor and electrophotographic imaging apparatus including the same
WO2015159940A1 (en) 2014-04-16 2015-10-22 株式会社リコー Photoelectric conversion element
JP6447754B2 (en) 2016-01-25 2019-01-09 株式会社リコー Photoelectric conversion element
KR102163405B1 (en) 2016-12-07 2020-10-08 가부시키가이샤 리코 Photoelectric conversion element
CN113939922A (en) 2019-06-10 2022-01-14 株式会社理光 Photoelectric conversion element, photoelectric conversion element module, electronic device, and power supply module
US20230189540A1 (en) 2019-07-16 2023-06-15 Ricoh Company, Ltd. Solar cell module, electronic device, and power supply module
US20210167287A1 (en) 2019-11-28 2021-06-03 Tamotsu Horiuchi Photoelectric conversion element, photoelectric conversion module, electronic device, and power supply module
US11502264B2 (en) 2020-02-27 2022-11-15 Ricoh Company, Ltd. Photoelectric conversion element and photoelectric conversion module
JP7413833B2 (en) 2020-02-27 2024-01-16 株式会社リコー Photoelectric conversion element and photoelectric conversion module
EP4064355A1 (en) 2021-03-23 2022-09-28 Ricoh Company, Ltd. Solar cell module
WO2023008085A1 (en) 2021-07-29 2023-02-02 Ricoh Company, Ltd. Photoelectric conversion element and solar cell module
JP2023137773A (en) 2022-03-18 2023-09-29 株式会社リコー Photoelectric conversion elements, photoelectric conversion modules, electronic equipment, and solar cell modules

Cited By (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3964904A (en) * 1974-08-22 1976-06-22 Xerox Corporation Manifold imaging member and process employing a dark charge injecting layer
US4134764A (en) * 1975-03-07 1979-01-16 Minnesota Mining And Manufacturing Company Semiconductive and sensitized photoconductive compositions
US4052209A (en) * 1975-03-07 1977-10-04 Minnesota Mining And Manufacturing Company Semiconductive and sensitized photoconductive compositions
US4123270A (en) * 1975-09-15 1978-10-31 International Business Machines Corporation Method of making electrophotographic imaging element
US4030923A (en) * 1975-12-11 1977-06-21 International Business Machines Corporation Mixture of binder materials for use in connection with a charge transport layer in a photoconductor
US4093358A (en) * 1976-12-27 1978-06-06 International Business Machines Corporation High efficiency electrochromic display device
US4090782A (en) * 1977-05-31 1978-05-23 International Business Machines Corporation Electrochromic display devices comprising thienylidene pyrazoline compounds
US4142783A (en) * 1977-05-31 1979-03-06 International Business Machines Corporation Reversible electrochromic display device having memory
US4363859A (en) * 1977-10-22 1982-12-14 Ricoh Company, Ltd. Electrophotographic photoconductor
US4175956A (en) * 1978-02-10 1979-11-27 Eastman Kodak Company Electrophotosensitive materials for migration imaging processes
US4314016A (en) * 1979-06-20 1982-02-02 Ricoh Co., Ltd. Electrophotographic element having a bisazo photoconductor
US4307167A (en) * 1980-03-03 1981-12-22 International Business Machines Corporation Layered electrophotographic plate having tetramethyl benzidene based disazo dye
US4423129A (en) * 1980-12-17 1983-12-27 Canon Kabushiki Kaisha Electrophotographic member having layer containing methylidenyl hydrazone compound
US4446217A (en) * 1981-02-03 1984-05-01 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a hydrazone containing layer
US4481272A (en) * 1981-03-20 1984-11-06 Basf Aktiengesellschaft Layered electrophotographic recording medium comprising heterocyclic nitrogen containing organic dye compounds
US4389475A (en) * 1981-03-20 1983-06-21 Basf Aktiengesellschaft Multilayered electrophotographic recording medium
US4418133A (en) * 1981-03-27 1983-11-29 Canon Kabushiki Kaisha Disazo photoconductive material and electrophotographic photosensitive member having disazo pigment layer
US4413045A (en) * 1981-05-26 1983-11-01 Canon Kabushiki Kaisha Multilayer electrophotographic photosensitive member comprises disazo charge generator layer, hydrazone transport layer
US4381337A (en) * 1981-11-23 1983-04-26 Pitney Bowes Inc. Polyester adhesive layer for photosensitive elements
US4456671A (en) * 1981-12-23 1984-06-26 Canon Kabushiki Kaisha Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound
US4543310A (en) * 1982-01-29 1985-09-24 Oce-Nederland B.V. Electrophotographic element and photocopying process making use of certain 4-[bis-phenylamino]benzaldehyde azines
US4487824A (en) * 1982-05-17 1984-12-11 Canon Kabushiki Kaisha Electrophotographic photosensitive member containing a halogen substituted hydrazone
US4820846A (en) * 1982-07-29 1989-04-11 Minnesota Mining And Manufacturing Company Triarylmethane compounds, their preparation and use as photoconductive systems
US4508811A (en) * 1983-01-17 1985-04-02 U.S. Philips Corporation Recording element having a pyrylium or thiopyrylium-squarylium dye layer and new pyrylium or thiopyrylium-squarylium compounds
US4500621A (en) * 1983-04-11 1985-02-19 Ricoh Systems, Inc. Sensitive electrophotographic plates containing squaric acid methine dyes suspended in a binder
US4481270A (en) * 1983-04-28 1984-11-06 Ricoh Systems, Inc. Photoreceptor containing squaric acid methine dyes
US4507480A (en) * 1983-05-09 1985-03-26 Xerox Corporation Squaraines
US4471041A (en) * 1983-05-09 1984-09-11 Xerox Corporation Photoconductive devices containing novel squaraine compositions
US4600673A (en) * 1983-08-04 1986-07-15 Minnesota Mining And Manufacturing Company Silicone release coatings for efficient toner transfer
US4508803A (en) * 1983-12-05 1985-04-02 Xerox Corporation Photoconductive devices containing novel benzyl fluorinated squaraine compositions
US4606986A (en) * 1983-12-05 1986-08-19 Xerox Corporation Electrophotographic elements containing unsymmetrical squaraines
US4523035A (en) * 1983-12-05 1985-06-11 Xerox Corporation Process for synthesizing squaraine compositions
US4486520A (en) * 1983-12-05 1984-12-04 Xerox Corporation Photoconductive devices containing novel squaraine compositions
EP0146301A1 (en) * 1983-12-05 1985-06-26 Xerox Corporation Process for synthesizing squaraine compositions
US4524218A (en) * 1984-01-11 1985-06-18 Xerox Corporation Processes for the preparation of squaraine compositions
US4626485A (en) * 1984-05-11 1986-12-02 Fuji Xerox Co., Ltd. Substituted squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same
US4677045A (en) * 1984-07-27 1987-06-30 International Business Machines Corporation Squarylium charge generating dye and electrophotographic photoconductor
US4559286A (en) * 1984-09-13 1985-12-17 Xerox Corporation Mixed squaraine photoconductive compositions
US4830786A (en) * 1986-02-27 1989-05-16 Syntex (U.S.A.) Inc. Squaraine dyes
US5416214A (en) * 1986-02-27 1995-05-16 Syntex (U.S.A.) Inc. Squaraine dyes
US5310922A (en) * 1986-02-27 1994-05-10 Syntex (U.S.A.) Inc. Squaraine dyes
US5329019A (en) * 1986-02-27 1994-07-12 Syntex (U.S.A.) Inc. Squaraine dye compounds
US5130217A (en) * 1991-09-17 1992-07-14 Lexmark International, Inc. Squarylium photoconductors with noncrystalline bisphenol a binders
US5338636A (en) * 1991-09-27 1994-08-16 Fuji Xerox Co., Ltd. Dichlorotin phthalocyanine crystal electrophotographic photoreceptor using the same, and coating composition for electrophotographic photoreceptor
US5463043A (en) * 1991-09-27 1995-10-31 Fuji Xerox Co., Ltd. Process for producing a dichlorotin phthalocyanine crystal
US5270139A (en) * 1992-07-02 1993-12-14 Industrial Technology Research Institute Photoconductor comprising bisazo and squarylium pigments as the charge generation material
US5488601A (en) * 1992-10-26 1996-01-30 Dai Nippon Printing Co., Ltd. Photoelectric sensor, information recording system, and information recording method
US5629920A (en) * 1992-10-26 1997-05-13 Dai Nippon Printing Co., Ltd. Photoelectric sensor, information recording system, and information recording method
US5486439A (en) * 1993-02-09 1996-01-23 Canon Kabushiki Kaisha Electrophotographic with polycarbonate having charge transporting group
US5510218A (en) * 1993-07-09 1996-04-23 Canon Kabushiki Kaisha Electrophotographic photosensitive member, process cartridge using same and electrophotographic apparatus
US5621130A (en) * 1993-10-22 1997-04-15 Canon Kabushiki Kaisha Electrophotographic photosensitive member, eletrophotographic apparatus and apparatus unit including the photosensitive member
US5622800A (en) * 1993-10-22 1997-04-22 Canon Kabushiki Kaisha Electrophotographic photosensitive member, electrophotographic apparatus and apparatus unit including the photosensitive member
US5935755A (en) * 1995-08-21 1999-08-10 Xerox Corporation Method for document marking and recognition
US5952142A (en) * 1997-07-31 1999-09-14 Oce-Technologies, B.V. Azine-containing photoconductive element
US6225015B1 (en) 1998-06-04 2001-05-01 Mitsubishi Paper Mills Ltd. Oxytitanium phthalocyanine process for the production thereof and electrophotographic photoreceptor to which the oxytitanium phthalocyanine is applied
WO2000053552A1 (en) * 1999-03-05 2000-09-14 Mitsubishi Chemical Corporation Squarylium compounds, filters for plasma display panels made by using the same, and plasma display panels
US20020014819A1 (en) * 1999-03-05 2002-02-07 Mitsubishi Chemical Corporation Squarylium compounds, filters for plasma display panels employing them, and plasma display panel devices
US6746629B2 (en) 1999-03-05 2004-06-08 Mitsubishi Chemical Corporation Squarylium compounds, filters for plasma display panels employing them, and plasma display panel devices
US20040101770A1 (en) * 2002-09-04 2004-05-27 Sharp Kabushiki Kaisha Organic photoconductive material, electrophotographic photoreceptor comprising the same, and image-forming apparatus
US7175956B2 (en) 2002-09-04 2007-02-13 Sharp Kabushiki Kaisha Organic photoconductive material, electrophotographic photoreceptor comprising the same, and image-forming apparatus
US7803507B2 (en) 2003-02-07 2010-09-28 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus including the same
US20070026334A1 (en) * 2003-02-07 2007-02-01 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus including the same
US20060210895A1 (en) * 2003-06-03 2006-09-21 Takatsugu Obata Photosensitive material for electrophotography and image forming device having the same
US7534539B2 (en) 2003-06-03 2009-05-19 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus having the same
US20060160812A1 (en) * 2003-07-03 2006-07-20 The Salk Institute For Biological Studies Methods for treating neural disorders and conditions, and compounds useful therefor
US20060215805A1 (en) * 2003-08-13 2006-09-28 Louis Aerts Sealing device for the outer surface of a nuclear fuel cladding
US7588871B2 (en) 2003-10-08 2009-09-15 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus provided with the same
US20070077506A1 (en) * 2003-10-08 2007-04-05 Akiki Kihara Electrophotographic photoreceptor and image forming apparatus provided with the same
US7429439B2 (en) 2003-11-19 2008-09-30 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus provided with the same
US20050164107A1 (en) * 2003-11-19 2005-07-28 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image forming apparatus provided with the same
US20050238972A1 (en) * 2003-12-01 2005-10-27 Sharp Kabushiki Kaisha Amine compound, manufacturing method thereof, electrophotographic photoreceptor using amine compound and image forming apparatus having the same
US7563548B2 (en) 2003-12-01 2009-07-21 Sharp Kabushiki Kaisha Amine compound, manufacturing method thereof, electrophotographic photoreceptor using amine compound and image forming apparatus having the same
US20050232657A1 (en) * 2004-01-29 2005-10-20 Sharp Kabushiki Kaisha Image forming apparatus
US7457565B2 (en) 2004-01-29 2008-11-25 Sharp Kabushiki Kaisha Image forming apparatus
US20050238973A1 (en) * 2004-03-30 2005-10-27 Sharp Kabushiki Kaisha Amine compound, electrophotographic photoreceptor using the amine compound and image forming apparatus having the same
US7364823B2 (en) 2004-03-30 2008-04-29 Sharp Kabushiki Kaisha Amine compound, electrophotographic photoreceptor using the amine compound and image forming apparatus having the same
US7794907B2 (en) 2004-09-07 2010-09-14 Sharp Kabushiki Kaisha Hydrazone compound, electrophotographic photoreceptor comprising the hydrazone compound, and image forming apparatus equipped with the electrophotographic photoreceptor
US20060057481A1 (en) * 2004-09-07 2006-03-16 Akihiro Kondoh Hydrazone compound, electrophotographic photoreceptor comprising the hydrazone compound, and image forming apparatus equipped with the electrophotographic photoreceptor
US20060275683A1 (en) * 2005-06-01 2006-12-07 Sharp Kabushiki Kaisha Asymmetric bis-hydroxyenamine compound, electrophotographic photoreceptor and image forming apparatus
US7625681B2 (en) 2005-06-01 2009-12-01 Sharp Kabushiki Kaisha Asymmetric bis-hydroxyenamine compound, electrophotographic photoreceptor and image forming apparatus
JP2006031030A (en) * 2005-07-22 2006-02-02 Kyowa Hakko Kogyo Co Ltd Synthetic resin molding
US7615326B2 (en) 2006-06-02 2009-11-10 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus
US20070281229A1 (en) * 2006-06-02 2007-12-06 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus
US8568946B2 (en) 2009-03-19 2013-10-29 Sharp Kabushiki Kaisha Electrophotographic photoreceptor and image formation device comprising same
US20110104600A1 (en) * 2009-10-29 2011-05-05 Kurauchi Takahiro Electrophotographic photoconductor and image forming apparatus using the same
US8465890B2 (en) 2010-08-30 2013-06-18 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus including the same, and coating solution for undercoat layer formation in electrophotographic photoconductor
US8546049B2 (en) 2010-12-21 2013-10-01 Sharp Kabushiki Kaisha Electrophotographic photoconductor and image forming apparatus using the same
US20120248419A1 (en) * 2011-02-09 2012-10-04 Mark Thompson Organic photosensitive devices comprising aryl squaraines and methods of making the same
US10333079B2 (en) 2011-02-09 2019-06-25 University Of Southern California Organic photosensitive devices comprising aryl squaraines and methods of making the same
US11944007B2 (en) 2011-02-09 2024-03-26 The Regents Of The University Of Michigan Organic photosensitive devices comprising aryl squaraines and methods of making the same
US10651390B2 (en) 2016-06-08 2020-05-12 Ricoh Company, Ltd. Tertiary amine compound, photoelectric conversion element, and solar cell

Also Published As

Publication number Publication date
FR2214138A1 (en) 1974-08-09
FR2214138B1 (en) 1977-06-10
JPS524188B2 (en) 1977-02-02
DE2401220A1 (en) 1974-07-25
JPS49105536A (en) 1974-10-05

Similar Documents

Publication Publication Date Title
US3824099A (en) Sensitive electrophotographic plates
US3837851A (en) Photoconductor overcoated with triarylpyrazoline charge transport layer
JPS6132666B2 (en)
JPH052145B2 (en)
US3533783A (en) Light adapted photoconductive elements
US3772011A (en) Print-out elements and methods using photoconductors and polygnes
EP0402980A1 (en) Electrophotographic recording material
US3585026A (en) Treatment of background areas of developed electrophotographic elements with carboxy substituted triarylamine photoconductors with an alkaline medium to reduce opacity
US4282298A (en) Layered imaging member and method
US3543025A (en) Electroradiographic x-ray sensitive element containing tetragonal lead monoxide
US4626485A (en) Substituted squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same
US3784375A (en) Ectrostatic image forms a developable image in a silver salt
JPS61188543A (en) Electrophotographic sensitive body
US5248579A (en) Electrophotographic recording material
JPS615253A (en) Electrophotographic sensitive body
US5055615A (en) Novel Squarium compounds, a process for preparing them and electrophotographic photoreceptors containing them
JPS58123542A (en) Electrophotographic receptor
JPH02293854A (en) Laminate type electrophotographic sensitive body
US5210301A (en) Squarium compounds, process for preparing the same and electrophotographic photoreceptors containing the same
EP0473800B1 (en) Laminated organic photosensitive material
JP2867561B2 (en) Function-separated photoconductor
JPS62121460A (en) Electrophotographic sensitive body
SU497783A3 (en) Electrophotographic material
JPH056179B2 (en)
JPH067268B2 (en) Electrophotographic photoconductor

Legal Events

Date Code Title Description
AS Assignment

Owner name: IBM INFORMATION PRODUCTS CORPORATION, 55 RAILROAD

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:INTERNATIONAL BUSINESS MACHINES CORPORATION;REEL/FRAME:005678/0098

Effective date: 19910326

Owner name: MORGAN BANK

Free format text: SECURITY INTEREST;ASSIGNOR:IBM INFORMATION PRODUCTS CORPORATION;REEL/FRAME:005678/0062

Effective date: 19910327