EP0504794B1 - Elément photosensible électrophotographique, son appareil et machine de fac-similé l'utilisant - Google Patents

Elément photosensible électrophotographique, son appareil et machine de fac-similé l'utilisant Download PDF

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Publication number
EP0504794B1
EP0504794B1 EP92104575A EP92104575A EP0504794B1 EP 0504794 B1 EP0504794 B1 EP 0504794B1 EP 92104575 A EP92104575 A EP 92104575A EP 92104575 A EP92104575 A EP 92104575A EP 0504794 B1 EP0504794 B1 EP 0504794B1
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EP
European Patent Office
Prior art keywords
aromatic ring
photosensitive member
group
electrophotographic photosensitive
groups
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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
EP92104575A
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German (de)
English (en)
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EP0504794A1 (fr
Inventor
Akio C/O Canon Kabushiki Kaisha Maruyama
Toshihiro C/O Canon Kabushiki Kaisha Kikuchi
Shoji C/O Canon Kabushiki Kaisha Amamiya
Shin C/O Canon Kabushiki Kaisha Nagahara
Katsumi C/O Canon Kabushiki Kaisha Aoki
Haruyuki C/O Canon Kabushiki Kaisha Tsuji
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Canon Inc
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Canon Inc
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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
    • G03G5/02—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
    • G03G5/0616—Hydrazines; Hydrazones
    • 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
    • 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
    • G03G5/06144—Amines arylamine diamine
    • 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
    • G03G5/06144—Amines arylamine diamine
    • G03G5/061443—Amines arylamine diamine benzidine
    • 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
    • G03G5/06147—Amines arylamine alkenylarylamine
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • 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
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/147—Cover layers
    • G03G5/14708—Cover layers comprising organic material
    • G03G5/14713—Macromolecular material
    • G03G5/14791—Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity

Definitions

  • the present invention relates to an electrophotographic photosensitive member, and more particularly to an electrophotographic photosensitive member comprised of a protective layer containing particular resin and a photosensitive layer containing a particular compound.
  • the present invention also relates to an electrophotographic apparatus, a device unit and a facsimile machine using such an electrophotographic photosensitive member.
  • An electrophotographic photosensitive member is of course required to have sensitivity, electric characteristics and optical characteristics necessary for the electrophotographic process.
  • a photosensitive member being used over again is brought into a condition that electrical and mechanical external forces caused during the steps of corona charging, image exposure, toner development, transfer to paper and cleaning are directly and repeatedly applied to the surface of the photosensitive member and, therefore, is required to withstand those external forces.
  • a photosensitive member must have durability against abrasion and/or flaws caused on its surface due to slide contact with other components during the steps of transfer and cleaning, deterioration of the photosensitive member and potential characteristics due to ozone generated during the step of corona charging, etc.
  • a good cleaning ability is also required.
  • Japanese Patent Application Laid-Open No. 56-42863 and No. 53-103741 propose use of a protective layer containing setting type resin as a main ingredient to improve hardness and wear resistance.
  • the EP-A-0 425 224 discloses an electrophotographic member comprising a photoconductive layer and a protective layer coated thereon and comprising a resin formed by hardening specific acrylic compounds.
  • the photosensitive layer contains a charge-transporting material, and the reference refers, in this respect, to a variety of patent literature encompassing a huge number of classes of organic photoconductive compounds. A specific hydrazone compound is used in an example of this reference.
  • an electrophotographic photosensitive member is formed by disposing a photosensitive layer and a protective layer in this order on an electroconductive support, wherein the protective layer is formed from a resin obtained by polymerization of curable acrylic monomer having at least three acrylic groups.
  • the charge transport layer of the photosensitive layer Example 5 of this document uses a compound corresponding to the reference Compound Example No. (1-24) listed below. Accordingly, the melting point thereof is 139.0 ⁇ 140.0.
  • the EP-A-0 464 749 discloses an electrophotographic photosensitive member comprising a photoconductive support and a photosensitive layer coated thereon in the form of a resinous layer obtained by polymerization of a specific phosphazene polyene compound. An additional protective layer formed from an acrylic type resin is not applied in the system of this reference.
  • obtaining a higher quality image requires not only that the protective layer of the photosensitive member has such characteristics as high hardness and superior wear resistance, but also that the protective layer itself has proper resistance.
  • the resistance of the protective layer is too high, there occurs an increase in the so-called residual potential, i.e., accumulation of electric charges in the protective layer through the repeated electrophotographic process of charging and exposure. This results in unstable image quality because the potential is not kept steady during repeated use of the photosensitive member.
  • the resistance is too low, an electrostatic latent image tends to drift in the planer direction, which gives rise to the problem such as blur or feathering.
  • Japanese Patent Application Laid-Open No. 57-30843 it is proposed in, for example, Japanese Patent Application Laid-Open No. 57-30843 to control resistance of a protective layer by adding a metal oxide in the form of electroconductive fine particles to the protective layer.
  • the protective layer and/or the photosensitive layer may crack when setting type resin is used as resin for the protective layer and an organic photosensitive layer is used as the photosensitive layer.
  • An object of the present invention is to provide an electrophotographic photosensitive member which can suppress the occurrence of cracks in the photosensitive member during forming of a protective layer, has high durability, and is free from any image defects.
  • Another object of the present invention is to provide an electrophotographic photosensitive member which can keep high image quality without accumulating a residual potential through the electrophotographic process repeated.
  • Still another object of the present invention is to provide an electrophotographic apparatus, a device unit and a facsimile machine using such as electrophotographic photosensitive member.
  • the present invention resides in an electrophotographic photosensitive member comprising a conductive support, a photosensitive layer and a protective layer, the protective layer containing resin formed by hardening a light-setting type acrylic monomer, and the photosensitive layer containing at least one compound selected from the group consisting of (A), (B) and (C) below as charge transport material:
  • the present invention resides in an electrophotographic apparatus, a device unit and a facsimile machine using the above electrophotographic photosensitive member.
  • Fig. 1 shows an example of schematic arrangement of an electrophotographic apparatus using an electrophotographic photosensitive member of the present invention.
  • Fig. 2 shows an example of a block diagram of a facsimile machine using the electrophotographic photosensitive member of the present invention.
  • a protective layer included in an electrophotographic photosensitive member of the present invention contains resin obtained by hardening a light-setting type acrylic monomer (hereinafter referred to as an acrylic monomer of the present invention).
  • the resin obtained from the light-setting type acrylic monomer has sufficient hardness which is one of important characteristics required for the protective layer.
  • the resin used in the present invention may be obtained from two or more light-setting type acrylic monomers or may be mixed with other types of resins such as polyester, polycarbonate, polyurethane, acrylic resin, epoxy resin, silicone resin, alkyd resin, and copolymer of vinyl chloride and vinyl acetate.
  • an optical starting agent (or photo-initiator) is used.
  • the amount of addition of the optical starting agent is preferably in a range of 0.1 to 40 wt.% based on the total weight of the acrylic monomer, more preferably in a range of 0.5 to 20 wt.%. Examples of the optical starting agent used are enumerated below, but not in a limiting sense.
  • the protective layer in the present invention preferably contains conductive particles, e.g., metal oxide particles, in a dispersed state.
  • Examples of such particles of conductive metal oxide are particles of zinc oxide, titanium oxide, tin oxide, antimony oxide, indium oxide, bismuth oxide, indium oxide doped with tin, tin oxide doped with antimony, and zirconium oxide. These metal oxides may be used solely or in the mixed form consisting of two or more kinds. Two or more kinds of metal oxides may be mixed with each other into the form of a solid solution or fusion.
  • the content of metal oxide particles in the present invention is preferably in a range of 5 to 90 wt.% based on the total weight of the protective layer, more preferably in a range of 10 to 90 wt.%.
  • a resistance value of the protective layer might be too high. If it is greater than 90 wt.%, the resistance value tends to be lower than a level required for the surface layer of the photosensitive member, thus resulting in a reduced charging ability and the cause of pin holes.
  • particle size is preferably smaller than the wavelength of incident light for the purpose of preventing the incident light from being scattered by the dispersed particles.
  • the number-average particle size is preferably less than 0.3 ⁇ m.
  • the larger number of functional groups per molecule is also preferable in point of hardness because the resin structure is more likely to become three-dimensional.
  • the protective layer in the present invention may be added with any of various coupling agent and/or anti-oxidizing agents.
  • the thickness of the protective layer in the present invention is preferably in a range of 0.1 to 10 ⁇ m, more preferably in a range of 0.5 to 7 ⁇ m.
  • the protective layer can be coated by any of such methods as spray coating, beam coating and dip coating.
  • the protective layer and the photosensitive layer have a tendency to easily crack.
  • the light setting type acrylic monomer as a monomer for resin used in the protective layer has higher hardness and is improved in such characteristics as resistance against scraping and flaws, with an increase in the number of functional groups in the acrylic monomer per molecule or unit weight.
  • dispersibility is improved as the number of functional groups in the light-setting type acrylic monomer increases. Accordingly, the advantage obtained by using the light-setting type acrylic monomer having the larger number of functional groups as a monomer for resin used in the protective layer is remarkable, and the invention of a technique of forming a protective layer on an organic photosensitive layer by the use of such resin without causing cracks is very valuable.
  • the inventors have conducted various studies and researches and, as a result, accomplished the present invention based on the finding that by providing a protective layer of the present invention on a photosensitive layer containing a charge transporting material which has the particular structure and melting point, a photosensitive member can be prevented from cracking.
  • an electrophotographic photosensitive member comprising a conductive support, a photosensitive layer and a protective layer, the protective layer containing resin formed by hardening a light-setting type acrylic monomer, and the photosensitive layer containing at least one compound selected from the group consisting of (A), (B) and (C) below:
  • Ar 1 and Ar 2 are each an aromatic ring group such as phenyl, naphthyl and anthryl.
  • Ar 3 is a bivalent aromatic ring group or a bivalent heterocyclic group derived from removing two hydrogen atoms from such an aromatic ring as benzene, naphthalene and anthracene, or such a heterocyclic group as thiophene and furan.
  • R 1 is an alkyl group such as methyl, ethyl, propyl and butyl, or an aromatic ring group such as phenyl and naphthyl.
  • R 2 is an alkyl group such as methyl, ethyl, propyl and butyl; an aromatic ring group such as phenyl and naphthyl; or a hydrogen atom.
  • Ar 1 , Ar 2 , Ar 3 , R 1 and R 2 each may have substituents.
  • substituents include an alkyl group such as methyl, ethyl, propyl and butyl; an alkoxy group such as methoxy, ethoxy and propoxy; an aryloxy group such as phenoxy and naphtoxy; a halogen atom such as fluorine, chlorine and bromine; or a di-substituted amino group such as dimethylamino, diethylamino and diphenylamino.
  • R 1 and R 2 may link to form a ring directly or via an atom such as carbon, sulfur and oxygen.
  • Ar 4 , Ar 5 and Ar 6 are each an aromatic ring group such as phenyl, naphthyl, anthryl, pyrenyl, fluorenyl, phenanthryl, 9,10-dihydrophenanthryl and fluorenonyl, or a heterocyclic group such as pyridyl, quinolyl, dibenzothienyl, dibenzofuryl, N-methylcarbazole, N-ethylcarbazole and N-tolylcarbazole.
  • the aromatic ring groups or the heterocyclic groups of Ar 4 , Ar 5 and Ar 6 each may have substituents thereof.
  • substituents include an alkyl group such as methyl, ethyl, propyl and butyl; an aralkyl group such as benzyl, phenetyl, and naphthylmethyl; an alkoxy group such as methoxy, ethoxy, and propoxy; an aryloxy group such as phenoxy and naphtoxy; a halogen atom such as fluorine, chlorine and bromine; an aromatic ring group such as phenyl and biphenyl; a diaryl amino group such as diphenyl amino and ditolyl amino; a dialkyl amino group such as dimethyl amino and diethyl amino; a diaralkyl amino group such as dibenzyl amino and diphenetyl amino; an alkyl aralkyl amino group such as benzylmethyl amino and benzylethyl amino; a
  • R 3 is an alkyl group such as methyl, ethyl and propyl, or a hydrogen atom.
  • R 4 and R 5 are each an alkyl group such as methyl, ethyl and propyl, an aralkyl group such as benzyl and phenetyl, or an aromatic ring group such as phenyl, naphthyl and anthryl. Note that R 4 and R 5 may link to form a ring.
  • n 2 is 1 or 2.
  • R 4 and R 5 each may have substituents thereof. Examples of possible substituents include an alkyl group such as methyl and ethyl; an alkoxy group such as methoxy and ethoxy; or a halogen atom such as fluorine, chlorine and bromine.
  • substituents include an alkyl group such as methyl and ethyl; an alkoxy group such as methoxy and ethoxy; a halogen atom such as fluorine, chlorine and bromine; a dialkyl amino group such as dimethyl amino and diethyl amino; a diaralkyl amino group such as dibenzyl amino and diphenetyl amino; or a diaryl amino group such as diphenyl amino and di(p-tolyl) amino.
  • alkyl group such as methyl and ethyl
  • an alkoxy group such as methoxy and ethoxy
  • a halogen atom such as fluorine, chlorine and bromine
  • a dialkyl amino group such as dimethyl amino and diethyl amino
  • a diaralkyl amino group such as dibenzyl amino and diphenetyl amino
  • a diaryl amino group such as diphenyl amino and di(p-tolyl) amino.
  • styryl compounds having the structure expressed by the formula (1) and their melting points.
  • No. (1)-1 to (1)-22 are styryl compounds having a melting point not higher than 135°C and used in the present invention
  • No. (1)-23 to (1)-40 are styryl compounds having the structure expressed by the formula (1), but of which melting points are higher than 135°C, and thus departing from the scope of the present invention.
  • the kinds of styryl compounds usable in the present invention are of course not limited to the following examples.
  • triarylamine compounds having the structure expressed by the formula (2) and their melting points are triarylamine compounds having the structure expressed by the formula (2) and their melting points.
  • No. (2)-1 to (2)-45 are triarylamine compounds having a melting point not higher than 150°C and used in the present invention
  • No. (2)-46 to (2)-72 are triarylamine compounds having the structure expressed by the formula (2), but of which melting points are higher than 150°C, and thus departing from the scope of the present invention.
  • the kinds of triarylamine compounds usable in the present invention are of course not limited to the following examples.
  • hydrazone compounds having the structure expressed by the formula (3) and their melting points.
  • No. (3)-1 to (3)-27 are hydrazone compounds having a melting point not higher than 155°C and used in the present invention
  • No. (3)-28 to (3)-47 are hydrazone compounds having the structure expressed by the formula (3), but of which melting points are higher than 155°C, and thus departing from the scope of the present invention.
  • the kinds of hydrazone compounds usable in the present invention are of course not limited to the following examples.
  • the photosensitive layer of the electrophotographic photosensitive member in the present invention may be of either the single-layer type that a charge generating material and a charge transporting material are contained in the same layer, or the laminated type that a charge transporting layer containing a charge transporting material and a charge generating layer containing a charge generating material are functionally separated from each other.
  • the laminated type photosensitive layer will now be described.
  • An arrangement of the laminated type photosensitive layer is divided into two types; one formed by laminating the charge transporting layer over the charge generating layer, and the other formed by laminating the charge generating layer over the charge transporting layer.
  • the charge transporting layer used in the present invention is formed by dissolving at least one of the compounds (A), (B) and (C) as the charge transporting material into resin, which has a film forming ability, using an appropriate solvent to prepare a coating solution, and then applying and drying the coating solution.
  • resin there can be used any kind of resin which has been conventionally employed for the charge transporting layer, in addition to the resin obtained by hardening the acrylic monomer of the present invention, and includes, for instance, polyester, polycarbonate, polymethacrylic acid and polystyrene.
  • the thickness of the charge transporting layer is preferably in a range of 5 to 40 ⁇ m, more preferably, in a range of 10 to 30 ⁇ m.
  • the charge transporting layer may be further added with any other suitable charge transporting materials than the compounds (A), (B) and (C).
  • the charge generating layer in the present invention is formed by dispersing a charge generating material into bonding resin to prepare a dispersed solution, and then coating and drying the dispersed solution.
  • bonding resin there can be used the resin of the present invention which is obtained by hardening acrylic monomer and includes, for instance, polyvinyl butyral, polystyrene, polyvinyl acetate, acrylic resin, cellulose acetate and ethyl cellulose.
  • the charge generating material examples include azo pigment such as Sudan red and Dian blue; quinone pigment such as pyrene quinone and anth-anthrone; quinocyanin pigment; perylene pigment; indigo pigment such as indigo and thioindigo; azulenium salt pigment; or phthalocyanine pigment such as copper phthalocyanine and titanyl phthalocyanine.
  • the thickness of the charge generating layer is preferably not greater than 5 ⁇ m, more preferably in a range of 0.05 to 2 ⁇ m.
  • the single-layer type photosensitive layer will be next described.
  • the single-layer type photosensitive layer is formed by preparing such a solution that at least one of the compounds (A), (B) and (C) and the charge generating material are dissolved and dispersed into the aforesaid resin, and then coating and drying the solution.
  • the thickness of the single-layer type photosensitive layer is preferably in a range of 5 to 40 ⁇ m, more preferably in a range of 10 to 30 ⁇ m.
  • the conductive support for use in the present invention may be of any material so long as it has conductivity, which includes, for instance, a metal or an alloy such as aluminum, chromium, nickel, stainless steel, copper and zinc; a composite formed by laminating a metal foil, such as aluminum and copper, over a plastic film; another composite by coating aluminum, indium oxide, tin oxide and the like over a plastic film with vapor deposition; or a metal, a plastic film, paper and the like on which a conductive layer is provided by coating a conductive material solely or together with appropriate binder resin.
  • a metal or an alloy such as aluminum, chromium, nickel, stainless steel, copper and zinc
  • a composite formed by laminating a metal foil, such as aluminum and copper, over a plastic film another composite by coating aluminum, indium oxide, tin oxide and the like over a plastic film with vapor deposition; or a metal, a plastic film, paper and the like on which a conductive layer is provided by coating a conductive
  • Examples of the conductive material used in that conductive layer include powder, a foil and fibers of a metal such as aluminum, copper, nickel and silver; a conductive metal oxide such as antimony oxide, indium oxide and tin oxide; a high molecular conductive material such as polypyrrole, polyaniline and high molecular electrolyte; carbon black, graphite powder and an organic or inorganic electrolyte; or conductive powder of which surface is coated with any of those conductive materials.
  • a metal such as aluminum, copper, nickel and silver
  • a conductive metal oxide such as antimony oxide, indium oxide and tin oxide
  • a high molecular conductive material such as polypyrrole, polyaniline and high molecular electrolyte
  • carbon black, graphite powder and an organic or inorganic electrolyte or conductive powder of which surface is coated with any of those conductive materials.
  • the conductive support may be in the form of a drum, sheet, belt or the like, the support is preferably formed into any desired shape optimum for the electrophotographic apparatus in which it is employed.
  • an underlying layer may be provided between the conductive support and the photosensitive layer.
  • the underlying layer functions as a barrier layer for controlling injection of charges at the interface between itself and the photosensitive layer, and/or as a bonding layer therebetween.
  • the underlying layer comprises primarily bonding resin, but may contain any of the aforesaid metals and alloys, or oxides and salts thereof, and surface active agents.
  • Examples of the bonding resin forming the underlying layer are polyester, polyurethane, polyacrylate, polyethylene, polystyrene, polybutadiene, polycarbonate, polyamide, polypropylene, polyimide, phenol resin, acrylic resin, silicone resin, epoxy resin, urea resin, allyl resin, alkyd resin, polyamide imide, nylon, polysulphone, polyallyl ether, polyacetal and butyral resin.
  • the film thickness of the underlying layer is preferably in a range of 0.05 - 7 ⁇ m, more preferably in a range of 0.1 to 2 ⁇ m.
  • Each of the above-mentioned layers can be formed by using vapor deposition and coating.
  • the coating method is preferable because it can form a wide variety of films ranging from a thin one to a thick one with various compositions.
  • the coating method includes, for instance, immersion coating, spray coating, beam coating, bar coating, blade coating and roller coating.
  • the electrophotographic photosensitive member of the present invention is applicable to not only electrophotographic copying machines, but also a wide field of electrophotographic applications such as a laser beam printer, CRT printer, LED printer, liquid crystal printer, facsimile machine and laser printing machine.
  • Fig. 1 shows an example of schematic arrangement of a transfer-type electrophotographic apparatus using an electrophotographic photosensitive member of the present invention.
  • a drum-type electrophotographic photosensitive member of the present invention as an image carrier, which is driven to rotate around a shaft 1a in the direction of arrow of a predetermined circumferential speed. While making a rotation, the photosensitive member 1 is charged uniformly into a positive or negative predetermined potential on the circumferential surface, and then subjected to an optical image exposure L (such as slit exposure and laser beam scanning exposure) by image exposure means (not shown) at an exposure section 3.
  • an optical image exposure L such as slit exposure and laser beam scanning exposure
  • the electrostatic latent image is developed using toner by development means 4, and the toner-developed image is successively transferred by transfer means 5 to the surface of a transfer material P fed from a paper feeder (not shown) between the photosensitive member 1 and the transfer means 5 in synchronism with the rotation of the photosensitive member 1.
  • the transfer material P having the image transferred thereto is separated from the surface of the photosensitive member and introduced to an image fixing means 8 for fixing of the image, following which it is printed out as a reproduced product (copy) outside of the apparatus.
  • the surface of the photosensitive member 1 is cleaned by cleaning means 6 to remove the toner left, and the charges remaining on the surface is removed by pre-exposure means 7 for the repeated image forming.
  • a corona charging device As the uniformly charging means 2 for the photosensitive member 1, a corona charging device is generally in widespread use. As the transfer means 5, a corona charging device is also generally in widespread use.
  • the electrophotographic apparatus may be arranged such that, of the above components such as the photosensitive member, the development means and the cleaning means, any plural ones are integrated into a device unit, which is attached to the apparatus body in a detachable manner. For instance, it is also possible to integrate the photosensitive member 1 and the cleaning means 6 into a single device unit, and detachably attach the unit to the apparatus body by guide means such as rails provided therein. In this case, the charging means and/or the development means may be further integrated into the device unit.
  • the optical image exposure L is performed by receiving the reflected light or passing light from or through an original, or directly reading the original for conversion into an electric signal, and then scanning a laser beam driving an LED array, or driving a liquid crystal shutter array in response to the electric signal.
  • Fig. 2 shows an example of this case in the form of a block diagram.
  • a controller 11 controls an image reading part 10 and a printer 19.
  • the controller 11 is controlled in its entirety by a CPU 17.
  • the read data from the image reading part 10 is transmitted to a partner station via transmitting circuit 13.
  • the data received from the partner station is sent to the printer 19 via a receiving circuit 12.
  • An image memory 16 stores predetermined image data therein.
  • a printer controller 18 controls the printer 19. Denoted at 14 is a telephone set.
  • the image information received from a line 15 (i.e., the image information received from a remote terminal connected via the line) is demodulated by the receiving circuit 12, decoded by the CPU 17, and then stored in the image memory 16 successively.
  • image recording of that page takes places.
  • the CPU 17 reads the image information of one page out of the memory 16 and sends the decoded image information of one page to the printer controller 18.
  • the printer controller 18 controls the printer 19 to perform the image information recording of that page.
  • the receiving and recording of images are carried out in this manner.
  • Dispersed for 12 hours by a sand mill apparatus using glass beads with diameter of 1 mm were 4 parts of disazo pigment represented by the below formula, 2 parts of polyvinyl butyral (rate of butyralization: 68%, weight average molecular weight: 24,000), and 34 parts of cyclohexanone. Then, a dispersion liquid for charge generation layer was prepared by adding 60 parts of tetrahydrofuran (THF) into the above dispersed mixture. The dispersion liquid was coated by spraying over the above charge transport layer, and then dried at 80°C for fifteen minutes to form a charge generation layer of 0.20 ⁇ m film thickness, providing a photosensitive layer of laminating type.
  • THF tetrahydrofuran
  • a film was formed on the photosensitive layer by beam coating, and then dried.
  • a protection layer was obtained by photo-setting for twenty seconds with a high pressure mercury vapor lamp of 8 mW/cm 2 intensity.
  • a film thickness of protection layer was 4 ⁇ m. Dispersion in the composition liquid of the protection layer was good and the surface thereof was uniform without unevenness.
  • the thus formed photosensitive member was observed by a transmission microscope with back light at an angle of 15° to check a degree of cracks appeared. Evaluation was conducted with three ranks of ⁇ , ⁇ , and ⁇ judged from appearance of cracks in the entire field of view by the microscope of 10 ⁇ magnification. ⁇ represents no cracks, ⁇ not more than five relatively small cracks within 1 cm, and ⁇ more than five cracks or layer crack(s) than 1 cm.
  • a coating material for conductive layer was prepared by dispersing by the sand mill apparatus using the glass beads of 1 mm diameter for two hours 50 parts of conductive titanium oxide powder coated by tin oxide containing antimony oxide of 10%, 25 parts of phenol resin, 20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000).
  • the coating material was coated by dipping on an aluminum cylinder ( ⁇ 30 mm x 260 mm), and dried at 140°C for thirty minutes. A conductive layer of film thickness of 20 ⁇ m was thus formed.
  • Example 2 An undercoat layer was formed in the same process as in Example 1, and a photosensitive layer and a protection layer were successively layered thereon in the same process as in Example 1 except use of the afore-exemplified styryl compound No. (1)-17 as the charge transport material, providing a photosensitive member.
  • the thus formed electrophotographic photosensitive member was assembled in a copier of positive development type, which repeats 1.5 sec cycle of charge, exposure, development, transfer, and cleaning processes. Electrophotographic properties were evaluated at the ordinary temperature in the ordinary humidity, and 10,000 times of image formation were repeated as a durability test.
  • Results are shown in Table 2.
  • the photosensitive member of Example 2 showed the sensitivity and the residual potential equivalent to those of a photosensitive member of Comparative example 1 without a protection layer, while keeping stable images without unevenness and black dot. Further, the photosensitive member of the present invention provided the stable images without occurrence of image degradation such as black band, which is an image defect of black belt.
  • Photosensitive members were prepared in the same manner as in Example 2 except that used were the afore-exemplified styryl compound Nos. (1)-7, (1)-9, (1)-13, (1)-16, and (1)-20 as the charge transport material and the afore-exemplified monomers (2), (7), (13), (15), and (18), respectively, as the acrylic monomer for protection layer, and evaluated similarly.
  • a conductive layer and an undercoat layer were provided on an aluminum cylinder in the same manner as in Example 2.
  • Dispersed for 20 hours by the sand mill apparatus using the glass beads of ⁇ 1 mm were 4 parts of disazo pigment represented by the below formula, 2 parts of polyvinyl benzal (rate of benzalization: 80%, weight average molecular weight: 11,000), and 30 parts of cyclohexanone. Then, a dispersion liquid for charge generation layer was prepared by adding 60 parts of methylethyl ketone into the above dispersed mixture.
  • the dispersion liquid was coated by spraying over the above-mentioned undercoat layer, and then dried at 80°C for fifteen minutes to form a charge generation layer of 0.20 ⁇ m film thickness.
  • An electrophotographic photosensitive member was obtained by forming a protection layer on the charge transport layer in the same manner as in Example 2.
  • the thus formed electrophotographic photosensitive member was assembled in a laser printer of reversal development type, which repeats 1.5 sec cycle of charge, laser exposure, development, transfer, and cleaning processes. Electrophotographic properties were evaluated at the ordinary temperature under the ordinary pressure, and 10,000 times of image formation were repeated as a durability test.
  • Photosensitive members were made in the same manner as in Example 2 except that their charge transport materials were prepared from the following compositions, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 2 except that no protection layer was formed, and evaluated similarly. Results are shown in Table 2. As shown in Table 2, the photosensitive member of Comparative example 1 showed good initial electrophotographic properties, but had a difficulty in formation of good image after the durability test of 300 sheets because of abrasion of the charge generation layer surface.
  • a photosensitive member was made in the same manner as in Example 2 except that the integrating resin in the protection layer was a polycarbonate resin. Using the photosensitive member, evaluation was conducted similar to Example 2.
  • Photosensitive members were made in the same manner as in Example 2 except that the afore-exemplified styryl compound Nos. (1)-26, (1)-28, and (1)-38 were used as the charge transport material, and evaluated similarly.
  • Photosensitive members were made in the same manner as in Example 1 except that triarylamine compounds as listed in Table 3 were used as the charge transport material, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 2 except that the afore-exemplified triarylamine compound No. (2)-18 was used as the charge transport material, and evaluated similarly.
  • Results are shown in Table 4.
  • the photosensitive member of Example 14 showed the sensitivity and the residual potential equivalent to those of a photosensitive member of Comparative example 6 without a protection layer, while keeping stable images without unevenness and black dot. Further, the photosensitive member of the present invention provided the stable images without occurrence of image degradation such as black band, which is an image defect of black belt.
  • Photosensitive members were prepared in the same manner as in Example 2 except that used were the afore-exemplified triarylamine compound Nos. (2)-4, (2)-17, (2)-19, (2)-30, and (2)-38 as the charge transport material, and the afore-exemplified monomers (2), (7), (13), (15), and (18), respectively, as the acrylic monomer for protection layer, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 8 except that the thickness of charge generation layer was 0.10 ⁇ m and that the afore-exemplified triarylamine compound No. (2)-8, was used as the charge transport material, and evaluated similarly.
  • Photosensitive members were made in the same manner as in Example 14 except that their charge transport materials were prepared from the following compositions, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 14 except that no protection layer was formed, and evaluated similarly.
  • Results are shown in Table 4.
  • the photosensitive member of Comparative example 6 showed good initial electrophotographic properties, but had a difficulty in formation of good image after the durability test of 300 sheets because of abrasion of the charge generation layer surface.
  • a photosensitive member was made in the same manner as in Example 14 except that the integrating resin in the protection layer was a polycarbonate resin. Using the photosensitive member, evaluation was conducted similar to Example 14.
  • Photosensitive members were made in the same manner as in Example 14 except that the afore-exemplified triarylamine compound Nos. (2)-53, (2)-59, and (2)-72 were used as the charge transport material, and evaluated similarly.
  • Photosensitive members were made in the same manner as in Example 1 except that hydrazone compounds as listed in Table 5 were used as the charge transport material, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 2 except that the afore-exemplified hydrazone compound No. (3)-17 was used as the charge transport material, and evaluated similarly.
  • Results are shown in Table 6.
  • the photosensitive member of Example 26 showed the sensitivity and the residual potential equivalent to those of a photosensitive member of Comparative example 11 without a protection layer, while keeping stable images without unevenness and black dot. Further, the photosensitive member of the present invention provided the stable images without occurrence of image degradation such as black band, which is an image defect of black belt.
  • Photosensitive members were prepared in the same manner as in Example 2 except that used were the afore-exemplified hydrazone compound Nos. (3)-4, (3)-13, (3)-15, (3)-18, and (3)-27 as the charge transport material, and the afore-exemplified monomers (2), (7), (13), (15), and (18), respectively, as the acrylic monomer for protection layer, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 8 except that the thickness of charge generation layer was 0.10 ⁇ m and that the afore-exemplified hydrazone compound No. (3)-19 was used as the charge transport material, and evaluated similarly.
  • Photosensitive members were made in the same manner as in Example 26 except that their charge transport materials were prepared from the following compositions, and evaluated similarly.
  • a photosensitive member was made in the same manner as in Example 26 except that no protection layer was formed, and evaluated similarly.
  • Results are shown in Table 6.
  • the photosensitive member of Comparative example 11 showed good initial electrophotographic properties, but had a difficulty in formation of good image after the durability test of 300 sheets because of abrasion of the charge generation layer surface.
  • a photosensitive member was made in the same manner as in Example 26 except that the integrating resin in the protection layer was a polycarbonate resin. Using the photosensitive member, evaluation was conducted similar to Example 26.
  • Photosensitive members were made in the same manner as in Example 26 except that the afore-exemplified hydrazone compound Nos. (3)-32, (3)-35, and (3)-40 were used as the charge transport material, and evaluated similarly.
  • the present invention may provide an electrophotographic photosensitive member, in which a photosensitive member is given without crack appearance a protection layer having high hardness and excellent durability, and which may supply high quality images without unevenness or defects of image from beginning to after substantial repetition use.
  • conductive microparticles may be dispersed in the protection layer.
  • the excellent dispersibility and dispersion stability thereof contribute to stable supply of higher quality image with high transparency and durability, but without residual potential.

Claims (26)

  1. Elément photosensible électrophotographique comprenant un support conducteur, une couche photosensible et une couche protectrice, ladite couche protectrice contenant une résine formée par durcissement d'un monomère acrylique sous l'action de la lumière, et ladite couche photosensible contenant au moins un composé choisi dans le groupe consistant en les composés (A), (B) et (C) ci-dessous comme matière de transport de charges :
    (A) des dérivés de styryle ayant une structure représentée par la formule (1) suivante et un point de fusion non supérieur à 135°C ;
    Figure 01110001
    formule dans laquelle Ar1 et Ar2 représentent des noyaux aromatiques, Ar3 représente un noyau aromatique bivalent ou un groupe hétérocyclique bivalent, R1 représente un groupe alkyle ou un noyau aromatique, R2 représente un atome d'hydrogène, un groupe alkyle ou un noyau aromatique, et n1 est égal à 1 ou 2, R1 et R2 pouvant être joints pour former un noyau lorsque n1 est égal à 1 ;
    (B) des dérivés de triarylamine ayant une structure représentée par la formule (2) suivante et un point de fusion non supérieur à 150°C ;
    Figure 01110002
    formule dans laquelle Ar4, Ar5 et Ar6 représentent chacun un noyau aromatique ou un groupe hétérocyclique ;
    (C) des dérivés d'hydrazone ayant une structure représentée par la formule (3) suivante et un point de fusion non supérieur à 155°C :
    Figure 01120001
    formule dans laquelle R3 représente un atome d'hydrogène ou un groupe alkyle, R4 et R5 représentent des groupes alkyle, des groupes aralkyle ou des noyaux aromatiques, n2 est égal à 1 ou 2, A représente un noyau aromatique, un groupe hétérocyclique ou un groupe - CH = C(R6)R7 (R6 et R7 représentent des atomes d'hydrogène, des noyaux aromatiques ou des groupes hétérocycliques, sous réserve que R6 et R7 ne représentent pas l'un et l'autre en même temps un atome d'hydrogène).
  2. Elément photosensible électrophotographique suivant la revendication 1, dans lequel le composé est un composé (A).
  3. Elément photosensible électrophotographique suivant la revendication 1, dans lequel le composé est un composé (B).
  4. Elément photosensible électrophotographique suivant la revendication 1, dans lequel le composé est un composé (C).
  5. Elément photosensible électrophotographique suivant la revendication 1, dans lequel le monomère acrylique durcissable sous l'action de la lumière comporte trois ou plus de trois groupes fonctionnels par molécule.
  6. Elément photosensible électrophotographique suivant la revendication 1, dans lequel le monomère acrylique durcissable sous l'action de la lumière a une teneur en groupes fonctionnels non inférieure à 0,004 mole/g.
  7. Elément photosensible électrophotographique suivant la revendication 1, dans lequel la couche protectrice contient des particules conductrices.
  8. Elément photosensible électrophotographique suivant la revendication 7, dans lequel les particules conductrices sont des particules d'oxyde métallique.
  9. Elément photosensible électrophotographique suivant la revendication 1, dans lequel la couche protectrice contient un agent de couplage et/ou un agent anti-oxydant.
  10. Elément photosensible électrophotographique suivant la revendication 1, dans lequel la couche photosensible comprend une couche de production de charges et une couche de transport de charges.
  11. Elément photosensible électrophotographique suivant la revendication 10, ledit élément photosensible électrophotographique comprenant un support conducteur, une couche de production de charges et une couche de transport de charges dans cet ordre.
  12. Elément photosensible électrophotographique suivant la revendication 10, ledit élément photosensible électrophotographique comprenant un support conducteur, une couche de transport de charges et une couche de production de charges dans cet ordre.
  13. Elément photosensible électrophotographique suivant la revendication 1, dans lequel la couche photosensible consiste en une seule couche.
  14. Elément photosensible électrophotographique suivant la revendication 1, ledit élément photosensible électrophotographique comprenant une couche sous-jacente entre le support conducteur et la couche photosensible.
  15. Appareil électrophotographique comprenant un élément photosensible électrophotographique, un moyen de formation d'image latente électrostatique, un moyen de développement d'une image latente électrostatique formée par ledit moyen de formation d'image électrostatique, et un moyen de transfert d'une image développée à une matière de transfert,
       ledit élément photosensible électrophotographique comprenant un support conducteur, une couche photosensible et une couche protectrice, ladite couche protectrice contenant une résine formée par durcissement d'un monomère acrylique sous l'action de la lumière, et ladite couche photosensible contenant au moins un composé choisi dans le groupe consistant en les composants (A), (B) et (C) ci-dessous comme matière de transport de charges :
    (A) des dérivés de styryle ayant une structure représentée par la formule (1) suivante et un point de fusion non supérieur à 135°C :
    Figure 01140001
    formule dans laquelle Ar1 et Ar2 représentent des noyaux aromatiques, Ar3 représente un noyau aromatique bivalent ou un groupe hétérocyclique bivalent, R1 représente un groupe alkyle ou un noyau aromatique, R2 représente un atome d'hydrogène, un groupe alkyle ou un noyau aromatique, et n1 est égal à 1 ou 2, R1 et R2 pouvant être joints pour former un noyau lorsque n1 est égal à 1 ;
    (B) des dérivés de triarylamine ayant une structure représentée par la formule (2) suivante et un point de fusion non supérieur à 150°C :
    Figure 01150001
    formule dans laquelle Ar4, Ar5 et Ar6 représentent chacun un noyau aromatique ou un groupe hétérocyclique ;
    (C) des dérivés d'hydrazone ayant une structure représentée par la formule (3) suivante et un point de fusion non supérieur à 155°C ;
    Figure 01150002
    formule dans laquelle R3 représente un atome d'hydrogène ou un groupe alkyle, R4 et R5 représentent des groupes alkyle, des groupes aralkyle ou des noyaux aromatiques, n2 est égal à 1 ou 2, A représente un noyau aromatique, un groupe hétérocyclique ou un groupe - CH = C(R6)R7 (R6 et R7 représentent des atomes d'hydrogène, des noyaux aromatiques ou des groupes hétérocycliques, sous réserve que R6 et R7 ne représentent pas l'un et l'autre un atome d'hydrogène en même temps).
  16. Appareil électrophotographique suivant la revendication 15, dans lequel le composé est un composé (A).
  17. Appareil électrophotographique suivant la revendication 15, dans lequel le composé est un composé (B).
  18. Appareil électrophotographique suivant la revendication 15, dans lequel le composé est un composé (C).
  19. Unité de dispositif, comprenant un élément photosensible électrophotographique et au moins un moyen choisi dans le groupe consistant en un moyen de chargement, un moyen de développement et un moyen de nettoyage,
       ledit élément photosensible électrophotographique comprenant un support conducteur, une couche photosensible et une couche protectrice, ladite couche protectrice contenant une résine formée par durcissement d'un monomère acrylique sous l'action de la lumière, et ladite couche photosensible contenant au moins un composé choisi dans le groupe consistant en les composés (A), (B) et (C) ci-dessous comme matière de transport de charges :
    (A) des dérivés de styryle ayant une structure représentée par la formule (1) suivante et un point de fusion non supérieur à 135°C :
    Figure 01160001
    formule dans laquelle Ar1 et Ar2 représentent des noyaux aromatiques, Ar3 représente un noyau aromatique bivalent ou un groupe hétérocyclique bivalent, R1 représente un groupe alkyle ou un noyau aromatique, R2 représente un atome d'hydrogène, un groupe alkyle ou un noyau aromatique, et n1 est égal à 1 ou 2, R1 et R2 pouvant être joints pour former un noyau lorsque n1 est égal à 1 ;
    (B) des dérivés de triarylamine ayant une structure représentée par la formule (2) suivante et un point de fusion non supérieur à 150°C :
    Figure 01160002
    formule dans laquelle Ar4, Ar5 et Ar6 représentent chacun un noyau aromatique ou un groupe hétérocyclique ;
    (C) des dérivés d'hydrazone ayant une structure représentée par la formule (3) suivante et un point de fusion non supérieur à 155°C :
    Figure 01170001
    formule dans laquelle R3 représente un atome d'hydrogène ou un groupe alkyle, R4 et R5 représentent des groupes alkyle, des groupes aralkyle ou des noyaux aromatiques, n2 est égal à 1 ou 2, A représente un noyau aromatique, un groupe hétérocyclique ou un groupe - CH = C(R6)R7 (R6 et R7 représentent des atomes d'hydrogène, des noyaux-aromatiques ou des groupes hétérocycliques, sous réserve que R6 et R7 ne représentent pas l'un et l'autre un atome d'hydrogène en même temps),
       ladite unité portant ledit élément photosensible électrophotographique et au moins un moyen choisi dans le groupe consistant en un moyen de chargement, un moyen de développement et un moyen de nettoyage, simultanément, et étant fixée à un corps d'appareil de manière amovible.
  20. Unité de dispositif suivant la revendication 19, dans laquelle le composé est un composé (A).
  21. Unité de dispositif suivant la revendication 19, dans laquelle le composé est un composé (B).
  22. Unité de dispositif suivant la revendication 19, dans laquelle le composé est un composé (C).
  23. Télécopieur comprenant un appareil électrophotographique et un moyen de réception d'une information d'image provenant d'un terminal éloigné,
    ledit appareil électrophotographique comprenant un élément photosensible électrophotographique,
    ledit élément photosensible électrophotographique comprenant un support conducteur, une couche photosensible et une couche protectrice, ladite couche protectrice contenant une résine formée par durcissement d'un monomère acrylique sous l'action de la lumière, et ladite couche photosensible contenant au moins un composé choisi dans le groupe consistant en les composés (A), (B) et (C) ci-dessous comme matière de transport de charges :
    (A) des dérivés de styryle ayant une structure représentée par la formule (1) suivante et un point de fusion non supérieur à 135°C :
    Figure 01180001
    formule dans laquelle Ar1 et Ar2 représentent des noyaux aromatiques, Ar3 représente un noyau aromatique bivalent ou un groupe hétérocyclique bivalent, R1 représente un groupe alkyle ou un noyau aromatique, R2 représente un atome d'hydrogène, un groupe alkyle ou un noyau aromatique, et n1 est égal à 1 ou 2, R1 et R2 pouvant être joints pour former un noyau lorsque n1 est égal à 1 :
    (B) des dérivés de triarylamine ayant une structure représentée par la formule (2) suivante et un point de fusion non supérieur à 150°C ;
    Figure 01190001
    formule dans laquelle Ar4, Ar5 et Ar6 représentent chacun un noyau aromatique ou un groupe hétérocyclique ;
    (C) des dérivés d'hydrazone ayant une structure représentée par la formule (3) suivante et un point de fusion non supérieur à 155°C ;
    Figure 01190002
    formule dans laquelle R3 représente un atome d'hydrogène ou un groupe alkyle, R4 et R5 représentent des groupes alkyle, des groupes aralkyle ou des noyaux aromatiques, n2 est égal à 1 ou 2, A représente un noyau aromatique, un groupe hétérocyclique ou un groupe - CH = C(R6)R7 (R6 et R7 représentent des atomes d'hydrogène, des noyaux aromatiques ou des groupes hétérocycliques, sous réserve que R6 et R7 ne représentent pas l'un et l'autre un atome d'hydrogène en même temps.
  24. Télécopieur suivant la revendication 23, dans lequel le composé est un composé (A).
  25. Télécopieur suivant la revendication 23, dans lequel le composé est un composé (B).
  26. Télécopieur suivant la revendication 23, dans lequel le composé est un composé (C).
EP92104575A 1991-03-18 1992-03-17 Elément photosensible électrophotographique, son appareil et machine de fac-similé l'utilisant Expired - Lifetime EP0504794B1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10032568B2 (en) 2014-04-09 2018-07-24 National Chung Hsing University Photosensitive organic dyes for dye-sensitized solar cells

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5449580A (en) * 1992-10-02 1995-09-12 Mita Industrial Co., Ltd. Organic photosensitive material for electrophotography
US5455135A (en) * 1992-12-18 1995-10-03 Canon Kabushiki Kaisha Electrophotographic photosensitive member with overlayer and electrophotographic apparatus employing same
DE69431541T2 (de) * 1993-03-29 2003-06-18 Mitsubishi Chem Corp Elektrophotographischer Photorezeptor für die Flüssigentwicklung
US5364727A (en) * 1993-06-21 1994-11-15 Hewlett-Packard Company Positive-charging organic photoconductor for liquid electrophotography
US5510218A (en) * 1993-07-09 1996-04-23 Canon Kabushiki Kaisha Electrophotographic photosensitive member, process cartridge using same and electrophotographic apparatus
US5876890A (en) * 1996-05-27 1999-03-02 Canon Kabushiki Kaisha Electrophotographic photosensitive member and apparatus and process cartridge provided with the same
EP0823669B1 (fr) * 1996-08-08 2001-03-14 Canon Kabushiki Kaisha Elément électrophotographique photosensible, cartouche de traitement et appareil électrophotographique le comprenant
EP0823668B1 (fr) * 1996-08-08 2002-11-13 Canon Kabushiki Kaisha Elément électrophotographique photosensible, cartouche de traitement et appareil électrophotographique l'utilisant
US6066426A (en) * 1998-10-14 2000-05-23 Imation Corp. Organophotoreceptors for electrophotography featuring novel charge transport compounds
US6214503B1 (en) 1999-12-21 2001-04-10 Imation Corp. Organophotoreceptors for electrophotography featuring novel charge transport compounds based upon hydroxy-functional compounds
EP1298496A3 (fr) * 2001-09-28 2004-10-27 SAMSUNG ELECTRONICS Co. Ltd. Photorécepteurs organiques électrophotographiques
JP4164317B2 (ja) 2002-08-28 2008-10-15 キヤノン株式会社 有機発光素子
US6960418B2 (en) * 2003-10-23 2005-11-01 Samsung Electronics Co., Ltd. Organophotoreceptor with charge transport material with two N,N,N-trisubstituted-amino groups
JP6060630B2 (ja) * 2012-11-08 2017-01-18 富士電機株式会社 電子写真用感光体

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4362799A (en) * 1978-04-28 1982-12-07 Canon Kabushiki Kaisha Image-holding member with a curable epoxyacrylate resin insulating layer
NL8600670A (nl) * 1986-03-17 1987-10-16 Gen Electric Polymeermengsel, dat een polyfenyleenether, een blokcopolymeer, een fosfaatester en toeslagstoffen bevat.
EP0425224A1 (fr) * 1989-10-26 1991-05-02 Fuji Photo Film Co., Ltd. Précurseur électrophotographique de plaque d'impression lithographique
JPH03246553A (ja) * 1990-02-23 1991-11-01 Idemitsu Petrochem Co Ltd 電子写真感光体
DE69116933T2 (de) * 1990-06-04 1996-07-11 Canon Kk Lichtempfindliches Element zur Elektrophotographie
DE69113529T2 (de) * 1990-07-02 1996-04-11 Canon Kk Element für die Bildherstellung.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10032568B2 (en) 2014-04-09 2018-07-24 National Chung Hsing University Photosensitive organic dyes for dye-sensitized solar cells

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DE69225736T2 (de) 1998-12-17
EP0504794A1 (fr) 1992-09-23

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