EP0376313B1 - Photosensitive member for electrophotography - Google Patents

Photosensitive member for electrophotography Download PDF

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Publication number
EP0376313B1
EP0376313B1 EP89124081A EP89124081A EP0376313B1 EP 0376313 B1 EP0376313 B1 EP 0376313B1 EP 89124081 A EP89124081 A EP 89124081A EP 89124081 A EP89124081 A EP 89124081A EP 0376313 B1 EP0376313 B1 EP 0376313B1
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EP
European Patent Office
Prior art keywords
member according
charge
layer
group
transport layer
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
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EP89124081A
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German (de)
English (en)
French (fr)
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EP0376313A2 (en
EP0376313A3 (en
Inventor
Akihiro Senoo
Ryoji Yashiro
Tetsuro Kanemaru
Toshihiro Kikuchi
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Canon Inc
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Canon Inc
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Filing date
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Publication of EP0376313A2 publication Critical patent/EP0376313A2/en
Publication of EP0376313A3 publication Critical patent/EP0376313A3/en
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Publication of EP0376313B1 publication Critical patent/EP0376313B1/en
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    • 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
    • G03G5/153—Charge-receiving layers combined with additional photo- or thermo-sensitive, but not photoconductive, layers, e.g. silver-salt layers
    • 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
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine

Definitions

  • the present invention relates to a photosensitive member for electrophotography, particularly to a photosensitive member for electrophotography comprising a low-molecular weight organic photoconductor capable of providing improved electrophotographic characteristics.
  • organic photoconductive polymers to be used for electrophotographic photosensitive members, such as polyvinyl carbazole.
  • These conventional organic polymers are superior to inorganic photoconductive materials in lightness (in weight), film-forming property, etc., but are inferior to the latter in sensitivity, durability, stability to environmental change, mechanical strength, etc.
  • the conventional low-molecular weight organic photoconductors represented by those as described above are used, the above-mentioned defect in film-forming property, which has conventionally posed a problem in the field of the organic photoconductive polymer, may be obviated by appropriately selecting a binder to be used in combination therewith.
  • these conventional organic photoconductors have not provide a sufficient sensitivity.
  • the electrophotographic photosensitive member comprising such a photosensitive layer may be improved in sensitivity to visible light, charge retentivity, surface strength, etc.
  • organic compounds As the charge-transporting substance constituting the above-mentioned transport layer, a large number of organic compounds have heretofore been proposed. Examples thereof include: pyrazoline compounds (Japanese Laid-Open Patent Application No. 72231/1977), hydrazone compounds (U.S. Patent 842,431 and Japanese Laid-Open Patent Application No. 52063/1980), triphenylamine compounds (Japanese Laid-Open Patent Application Nos. 195254/1982 and 58445/1979), stilbene compounds (Japanese Laid-Open Patent Application Nos. 151955/1979 and 198043/1983), carbazole compounds (Japanese Laid-Open Patent Application Nos. 150128/1979 and 58451/1988), benzothiophene compounds (Japanese Laid-Open Patent Application No. 110835/1979), etc.
  • pyrazoline compounds Japanese Laid-Open Patent Application No. 72231/1977
  • hydrazone compounds U.S. Patent 8
  • the EP-A-0 161 934 discloses an electrophotographic photosensitive member having a charge transporting layer containing a charge transporting triarylamine compound.
  • Two aromatic residues of the triarylamine compound are selected from the group consisting of a substituted or unsubstituted phenyl group, naphthyl group and polyphenyl group, and the third amine residue of the triarylamine compound is selected from the group consisiting of a substituted or unsubstituted aryl group, alkyl group having from 1 to 18 carbon atoms and cyclo-aliphatic compounds having from 3 to 18 carbon atoms.
  • triphenyl amine, a specific bis-triarylamine, a specific bis-arylamine ether and a specific bis-alkyl-arylamine are mentioned.
  • the sensitivity and other electrophotographic characteristics are not necessarily sufficient, and the light part potential and dark part potential are liable to show a considerable change, when charging and exposure operations are conducted repetitively.
  • An object of the present invention is to provide an electrophotographic photosensitive member which has solved the above-mentioned various problems encountered in the conventional photosensitive member.
  • Another object of the present invention is to provide an electrophotographic photosensitive member using a novel organic photoconductor which may easily be produced, is relatively inexpensive and is excellent in durability.
  • a photosensitive member for electrophotography comprising an electroconductive substrate and a photosensitive layer disposed thereon, wherein the photosensitive layer comprises a triarylamine compound represented by the following general formula (I): wherein Ar1 and Ar2 respectively denote a benzene ring capable of having at least one substituent; at least one of Ar1 and Ar2 has an electron-donating substituent; and R1 and R2 respectively denote a hydrogen atom, alkyl or alkoxyl.
  • Ar1 and Ar2 respectively denote a benzene ring capable of having at least one substituent; at least one of Ar1 and Ar2 has an electron-donating substituent; and R1 and R2 respectively denote a hydrogen atom, alkyl or alkoxyl.
  • Figures 1 and 2 show infrared absorption spectra of Compound Example Nos. 10 and 13, respectively, according to the KBr tablet (or pellet) method.
  • Ar1 and Ar2 respectively denote a benzene ring capable of having one or more substituent. At least one of Ar1 and Ar2 has an electron-donating (or electron donative) group as a substituent.
  • the "electron-donating substituent” used herein refers to a substituent having a greater electron-donating ability than a hydrogen atom.
  • the electron-donating group may include: alkyl groups (preferably C1 to C3) such as methyl, ethyl and propyl; alkoxyl groups (preferably C1 to C3) such as methoxy and ethoxy groups; substituted amino group (preferably, di-substituted amino group) such as dimethylamino and diethylamino groups; etc.
  • the substituent of the amino group may preferably be C1 to C3.
  • R1 and R2 respectively denote a hydrogen atom, alkyl groups (preferably C1 to C3) such as methyl, ethyl and propyl; alkoxyl groups (preferably C1 to C3) such as methoxy and ethoxy.
  • an electron-donating substituent is introduced into at least one of the benzene rings of Ar1 and Ar2 in the above-mentioned formula (I).
  • a compound of the above-mentioned formula (I) having an oxidation potential of 0.9 V or below wherein at least one electron-donating group is introduced into the benzene ring of Ar1 and/or Ar2 may provide an excellent electrophotographic characteristic. Further, such a compound having an oxidation potential of 0.60 V or above and 0.88 V or below may provide an electrophotographic photosensitive member having an extremely high sensitivity.
  • the compound having an oxidation potential of above 0.9 V only provides insufficient carrier injection property from a charge-generation layer.
  • the compound having an oxidation potential of below 0.60 V provides relatively large dark decay and relatively high residual potential to deteriorate the electrophotographic characteristic, while the reason for such a phenomenon is not necessarily clear.
  • the oxidation potential values referred to in the present invention are based on a measurement using a potential-sweeping method wherein a saturated calomel electrode was used as the reference electrode, and a 0.1 N solution of (n-Bu)4N+ClO 4 - in acetonitrile was used as the electrolytic solution.
  • the potential of the working electrode comprising platinum was swept to obtain a current-potential curve.
  • the oxidation potential was defined as the potential value corresponding to the peak of the thus obtained current-potential curve.
  • a sample was dissolved, at a concentration of about 5 - 10 mmol %, in an electrolytic solution of 0.1 N (n-Bu)4N+ClO 4 - in acetonitrile. Then, a voltage was externally applied to the resultant sample solution, and a change in current was measured while linearly changing the voltage from a low potential value, thereby to obtain a current-potential curve.
  • a counter electrode comprising platinum was used, and the potential (difference) between the working electrode and the counter electrode was measured while the potential (difference) between the reference electrode and the counter electrode was defined as 0 (zero).
  • the oxidation potential was determined by the potential value corresponding to the peak of the current value in the above-mentioned current-potential curve.
  • the above-mentioend Compound Example may be synthesized in the following manner.
  • the compound according to the present invention may easily be synthesized in a high yield by using a one-step process as described above, it may provide an inexpensive electrophotographic photosensitive member.
  • the photosensitive layer is function-separated into a charge generation layer and a charge transport layer
  • the charge transport layer comprises the triarylamine compound represented by the above-mentioned general formula (I) as a charge-transporting substance.
  • the charge transport layer according to the present invention may preferably be formed by dissolving the above-mentioned compound of the formula (1) in an appropriate solvent together with a binder, applying the resultant coating liquid such as solution onto a predetermined surface, and drying the resultant coating.
  • binder to be used in the charge transport layer may include: polyarylate resins, polysulfone resins, polyamide resins, acrylic resins, acrylonitrile resins, methacrylic resins, vinyl chloride resins, vinyl acetate resins, phenol resins, epoxy resins, polyester resins, alkyd resins, polycarbonate, polyurethane, or copolymer resins containing two or more of the recurring units of these resins, such as styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, etc.
  • organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene and polyvinylpyrene may be used.
  • the charge-transporting substance may preferably be used in an amount of 10 - 500 wt. parts, more preferably 50 - 200 wt. parts, per 100 wt. parts of the binder.
  • the charge transport layer is electrically connected to the charge generation layer as described hereinafter, and has a function of receiving charge carriers injected from the charge generation layer in the presence of an electric field and of transporting these charge carriers to the surface of the charge transport layer.
  • the charge transport layer may be disposed on the charge generation layer, or may be disposed under the charge generation layer.
  • the charge transport layer may preferably be disposed on the charge generation layer. It is not preferred that the charge transport layer has too large a thickness, since there is a certain limit to the thickness thereof suitable for the transport of the charge carriers.
  • the charge transport layer may preferably have a thickness of 5 - 40 microns, more preferably 10 - 30 microns.
  • the organic solvent to be used in the above-mentioned formation of the charge transport layer may vary depending on the kind of the binder used therefor, and may preferably be selected from those which do not substantially dissolve the charge generation layer or a primer (or undercoat) layer as described hereinafter.
  • organic solvent may include: alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether; esters such as methyl acetate and ethyl acetate; aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene; aromatic compounds such as benzene, toluene, xylene, monochlorobenzene, and dichlorobenzene; etc.
  • alcohols such as methanol, ethanol, and isopropanol
  • ketones such as acetone
  • the coating may be effected by various coating methods such as dip coating, spray coating, wire bar coating, and blade coating.
  • the drying should preferably be conducted in the sequence of drying at room temperature to a "tack-free" state and then heat drying. In general, the heat drying may preferably be conducted for a time in the range of 5 minutes to 2 hours at a temperature of 30 °C to 200 °C under quiescent condition or under blowing.
  • the charge transport layer according to the present invention can further contain an additive selected from various species thereof.
  • an additive may include: plasticizers such as diphenyl, m-terphenyl and dibutyl phthalates; surface-lubricating agents such as silicone oil, graft-type silicone polymers, and various fluorocarbons; potential stabilizing agents such as dicyanovinyl compounds and carbazole derivatives; anti-oxidizing agents such as ⁇ -carotene, Ni complexes, and 1,4-diazabicyclo[2,2,2]-octane; etc.
  • the charge generation layer may comprise a charge-generating substance.
  • the charge-generating substance may include: inorganic charge-generating substances such as selenium, selenium-tellurium, and amorphous silicon; and organic charge-generating substances including: cationic dyes such as pyrylium dye, thiapyrylium dye, azulenium dye, thiacyanine dye, and quinocyanine dye; polycyclic quinone pigments such as squarium salt dye, phthalocyanine pigment, anthanthrone pigment, dibenzpyrene-quinone pigment, and pyranthrone pigment; indigo pigment; quinacridone pigment; azo pigment; etc.
  • These charge-generating substances may be used singly or as a combination of two or more species.
  • the charge generation layer may be formed by using such a charge-generating substance in the form of a vapor deposition layer or coating layer.
  • the azo pigment particularly includes various types. Representative structures of the azo pigment preferably used in the present invention are described hereinbelow.
  • coupler portion Cp include those having the following structures:
  • the above-mentioned central structures A and coupler Cp may appropriately be combined to form a pigment as a charge-generating substance.
  • the charge generation layer may be formed by vapor-depositing such a charge-generating substance by means of a vacuum vapor deposition device, or by applying a dispersion containing such a charge-generating substance dispersed therein, together with an appropriate binder as desired.
  • the binder to be used for forming the charge generation layer may be selected from a wide variety of insulating resins or alternatively from organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene, and polyvinylpyrene.
  • the insulating resin such as polyvinyl butyral, polyarylates (e.g., polycondensation product between bisphenol A and phthalic acid), polycarbonate, polyester, phenoxy resin, acrylic resin, polyacrylamide resin, polyamide, polyvinyl pyridine, cellulose resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and polyvinyl pyrrolidone.
  • the resin may preferably be contained in the charge generation layer in an amount of 5 - 80 wt. %, more preferably 10 - 40 wt. %.
  • organic solvent usable in the coating of the charge generation layer may include: alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; sulfoxides such as dimethyl sulfoxide; ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether; esters such as methyl acetate and ethyl acetate; aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene; aromatic compounds such as benzene, toluene, xylene, monochlorobenzene, and dichlorobenzene; etc.
  • alcohols such as methanol, ethanol, and isopropano
  • the charge generation layer may preferably contain the above-mentioned charge-generation substance in an amount as large as possible, so that it may provide a sufficient absorbance. Further, the charge generation layer may preferably be a thin layer having a thickness of 5 microns or below, more preferably 0.01 - 1 micron so that it may inject charge carriers generated therein into the charge transport layer within the lifetime of the charge carriers. This may be attributable to facts such that most of the incident light quantity may preferably be absorbed into the charge generation layer to generate a large number of charge carriers, and that the thus generated charge carriers may preferably be injected into the charge transport layer without deactivation due to recombination or trapping thereof.
  • the above-mentioned photosensitive layer having a laminate structure comprising a charge generation layer and a charge transport layer may be disposed on an electroconductive substrate.
  • the electroconductive substrate may be a substrate which per se has an electroconductivity such as those of aluminum, aluminum alloy, copper, zinc, and stainless steel; alternatively, the above-mentioned metal substrate or a substrate of a plastic coated with, e.g., a vacuum vapor-deposited layer of aluminum, aluminum alloy, indium oxide, tin oxide or indium oxide-tin oxide alloy, or a mixture of an electroconductive powder (such as aluminum powder, titanium oxide, tin oxide, zinc oxide, carbon black and silver particles) and an appropriate binder; a substrate of paper or plastic impregnated with electroconductive particles, or a plastic substrate coated with an electroconductive polymer layer.
  • the electroconductive substrate may be in any form such as sheet, drum, etc.
  • the primer layer may comprise e.g., casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (e.g., nylon 6, nylon 66, nylon 610, copolymer nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, or aluminum oxide.
  • the thickness of the primer layer should preferably be 0.1 - 5 microns, particularly 0.5 to 3 microns.
  • a protective layer can further be disposed on the photosensitive layer.
  • a protective layer may comprise a resin, or a resin and an electroconductive material dispersed therein.
  • a pigment or dye having a photoconductivity may be used as a sensitizer.
  • a dye or pigment include: the above-mentioned disazo pigment, pyrylium dye, thiapyrylium dye, selenapyrylium dye, benzopyrylium dye, benzothiapyrylium dye, naphthopyrylium dye, and naphthothiapyrylium dye, as described in U.S. Patent 3,554,745; 3,567,438; and 3,586,500.
  • an euteclic (crystal) complex comprising a pyrylium dye (as disclosed in U.S. Patent 3,684,502) and an electrically insulating polymer comprising an alkylidene-diarylene portion may be used as a sensitizer.
  • Such an eutectic complex may be formed by dissolving 4-[4-bis(2-chloroethyl)aminophenyl]-2,6-diphenylthiapyrylium perchlorate and poly(4,4′-isopropylidene diphenylene carbonate) in a halogenated hydrocarbon-type solvent (e.g., dichloromethane, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, bromobenzene, 1,2-dichlorobenzene, etc.), and then adding a non-polar solvent (e.g., hexane, octane, decane, 2,2,4-trimethylbenzene, ligroin, etc.) to the resultant mixture so as to produce a particulate eutectic complex.
  • the electrophotographic photosensitive member may include a binder such as styrene-butadiene copolymer, silicone resin, vinyl resin, vinylidene chloride-acrylonitrile copolymer, styrene-acrylonitrile copolymer, vinyl acetate-vinyl chloride copolymer, polyvinyl butyral, polymethyl methacrylate, poly-N-butyl methacrylate, polyester, cellulose ester, etc.
  • a binder such as styrene-butadiene copolymer, silicone resin, vinyl resin, vinylidene chloride-acrylonitrile copolymer, styrene-acrylonitrile copolymer, vinyl acetate-vinyl chloride copolymer, polyvinyl butyral, polymethyl methacrylate, poly-N-butyl methacrylate, polyester, cellulose ester, etc.
  • the electrophotographic photosensitive member according to the present invention may be used not only for ordinary copying machines but also in the fields related to electrophotography such as laser printers, CRT printers and electrophotographic plate-making.
  • a disazo pigment represented by the following formula: and a solution obtained by dissolving 2 g of a butyral resin (butyral degree: 63 mol. %) in 100 ml of cyclohexanone were dispersed for 24 hours by means of a sand mill to prepare a coating liquid.
  • the thus prepared coating liquid was applied onto an aluminum sheet by means of a wire bar to form a charge generation layer having a thickness (after drying) of 0.2 micron.
  • the thus prepared photosensitive member was charged by using corona (-5 KV) according to a static method by means of an electrostatic copying paper tester (Model: SP-428, mfd. by Kawaguchi Denki K.K.) and retained in a dark place for 1 sec. Thereafter, the photosensitive member was exposed to light at an illuminance of 20 lux, to evaluate the charging characteristic.
  • the surface potential (V0), the potential (V1) obtained after a dark decay of 1 sec, and the exposure quantity (E 1/2 ) required for decreasing the potential V1 to 1/2 thereof were measured.
  • the photosensitive member prepared in this instance was bonded to the cylinder for a photosensitive drum to be used for a plain paper copying (PPC) machine (NP-3525, mfd. by Canon K.K.) and subjected to a copying test of 5000 sheets, and thereafter, the variations in the light part potential (V L ) and dark part potential (V D ) in the initial stage and after the copying of 5000 sheets were determined.
  • the initial V D and V L were set to -700 V and -200 V, respectively.
  • Example 1 For the purpose of comparison, three species of photosensitive members were prepared in the same manner as in Example 1 except that the following comparative compounds were respectively used as the charge-transporting substance (Comparative Examples 1 - 3).
  • the arylamine compounds represented by the following formulas (II), (III) and (IV) provided a particularly high sensitivity and an excellent potential stability in successive copying.
  • a charge-generating substance represented by the following formula: a solution obtained by dissolving 5 g of a butyral resin (butyral degree: 63 mol. %) and 200 g of dioxane were dispersed for 48 hours by means of a ball mill disperser to prepare a coating liquid.
  • the thus prepared coating liquid was applied onto the above-mentioned primer layer by a blade coating method to form a charge generation layer having a thickness (after drying) of 0.15 micron.
  • the thus prepared photosensitive member was charged by using corona discharge (-5 KV) so as to have an initial potential of V0, left standing in a dark place for 1 sec, and thereafter the surface potential thereof was measured.
  • the exposure quantity (E 1/2 , ⁇ J/cm) required for decreasing the potential V1 after the dark decay to 1/2 thereof was measured.
  • the light source used herein was laser light (output: 5 mW, emission wavelength: 780 nm) emitted from a ternary semiconductor comprising gallium/aluminum/arsenic.
  • the above-mentioned photosensitive member was assembled in a laser beam printer (trade name: LBP-CX, mfd. by Canon K.K.) as an electrophotographic printer equipped with the above-mentioned semiconductor laser using a reversal development system, and subjected to actual image formation.
  • a laser beam printer (trade name: LBP-CX, mfd. by Canon K.K.) as an electrophotographic printer equipped with the above-mentioned semiconductor laser using a reversal development system, and subjected to actual image formation.
  • the image formation was effected by line-scanning the laser beam corresponding to character and image signals. As a result, good prints were obtained with respect to the characters and images.
  • aqueous ammonia solution of casein (comprising 11.2 g of casein, 1 g of 28 % ammonia water, and 222 ml of water) was applied onto an aluminum plate by means of a wire bar to form a primer layer having a thickness of 1 micron (after drying).
  • a charge transport layer and a charge generation layer were successively formed in the same manner as in Example 9, whereby an electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that the laminate structure was different.
  • a 5 % methanol solution of a soluble nylon (6-66-610-12 quaternary copolymer nylon) was applied onto an aluminum substrate to form a primer layer having a thickness of 0.5 micron (after drying).

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP89124081A 1988-12-29 1989-12-28 Photosensitive member for electrophotography Expired - Lifetime EP0376313B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP330997/88 1988-12-29
JP63330997A JPH02178668A (ja) 1988-12-29 1988-12-29 電子写真感光体

Publications (3)

Publication Number Publication Date
EP0376313A2 EP0376313A2 (en) 1990-07-04
EP0376313A3 EP0376313A3 (en) 1990-08-29
EP0376313B1 true EP0376313B1 (en) 1996-03-13

Family

ID=18238678

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89124081A Expired - Lifetime EP0376313B1 (en) 1988-12-29 1989-12-28 Photosensitive member for electrophotography

Country Status (9)

Country Link
EP (1) EP0376313B1 (zh)
JP (1) JPH02178668A (zh)
KR (1) KR940003105B1 (zh)
CN (1) CN1078714C (zh)
AU (1) AU604428B2 (zh)
CA (1) CA2006857C (zh)
DE (1) DE68925955D1 (zh)
FR (1) FR2641384B1 (zh)
GB (1) GB2226653B (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5393629A (en) * 1991-04-26 1995-02-28 Fuji Xerox Co., Ltd. Electrophotographic photoreceptor
EP0617005B1 (en) * 1993-03-22 2001-06-13 Fuji Xerox Co., Ltd. Triarylamine compound, process for producing the same and electrophotographic photoreceptor using the same
TW382076B (en) * 1993-06-30 2000-02-11 Canon Kk Electrophotographic photosensitive member and electrophotographic apparatus using same
JPH07233106A (ja) * 1994-02-23 1995-09-05 Fuji Xerox Co Ltd モノヨウ素化芳香族化合物の製造方法
US5529868A (en) * 1994-03-23 1996-06-25 Fuji Xerox Co., Ltd. Electrophotographic photoreceptor
US7138555B2 (en) 2004-04-20 2006-11-21 Xerox Corporation Process for preparing iodoaromatic compounds and using the same

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3277036D1 (en) * 1981-04-22 1987-09-24 Eastman Kodak Co Condensation polymeric photoconductors containing pendant arylamines, photoconductive compositions and electrophotographic elements containing these photoconductors
US4725518A (en) * 1984-05-15 1988-02-16 Xerox Corporation Electrophotographic imaging system comprising charge transporting aromatic amine compound and protonic acid or Lewis acid
JPH0823699B2 (ja) * 1986-02-28 1996-03-06 三田工業株式会社 電子写真感光体
JPH0715583B2 (ja) * 1987-04-30 1995-02-22 富士ゼロックス株式会社 電子写真感光体
US4806444A (en) * 1987-06-10 1989-02-21 Xerox Corporation Arylamine polymers and systems utilizing arylamine polymers
JP2753582B2 (ja) * 1987-10-20 1998-05-20 株式会社リコー 電子写真用感光体
JP2742546B2 (ja) * 1988-02-19 1998-04-22 株式会社リコー アミノビフェニル化合物

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GB8929200D0 (en) 1990-02-28
CA2006857C (en) 1995-10-24
JPH0516019B2 (zh) 1993-03-03
JPH02178668A (ja) 1990-07-11
KR940003105B1 (ko) 1994-04-13
KR900010481A (ko) 1990-07-07
EP0376313A2 (en) 1990-07-04
FR2641384B1 (fr) 1993-12-31
EP0376313A3 (en) 1990-08-29
GB2226653A (en) 1990-07-04
CA2006857A1 (en) 1990-06-29
AU4708789A (en) 1990-07-19
FR2641384A1 (fr) 1990-07-06
AU604428B2 (en) 1990-12-13
CN1044172A (zh) 1990-07-25
DE68925955D1 (de) 1996-04-18
GB2226653B (en) 1992-07-01
CN1078714C (zh) 2002-01-30

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