WO2024143485A1 - 化合物、組成物及び電子写真感光体 - Google Patents

化合物、組成物及び電子写真感光体 Download PDF

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WO2024143485A1
WO2024143485A1 PCT/JP2023/046986 JP2023046986W WO2024143485A1 WO 2024143485 A1 WO2024143485 A1 WO 2024143485A1 JP 2023046986 W JP2023046986 W JP 2023046986W WO 2024143485 A1 WO2024143485 A1 WO 2024143485A1
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group
substituent
compound
formula
integer
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English (en)
French (fr)
Japanese (ja)
Inventor
司 長谷川
ラミレス マヌエル エミリオ オテロ
明 安藤
英貴 五郎丸
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Mitsubishi Chemical Corp
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Mitsubishi Chemical Corp
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Priority to JP2024567942A priority Critical patent/JPWO2024143485A1/ja
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Priority to US19/251,782 priority patent/US20250320211A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • 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 or 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
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive 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 or 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
    • 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 or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/14—Inert intermediate or cover layers for charge-receiving layers
    • G03G5/147—Cover 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 or 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
    • G03G5/14717—Macromolecular material obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/14726—Halogenated polymers

Definitions

  • the present invention relates to a compound having an electron transport structure and a composition containing the compound.
  • the compound and composition of the present invention are useful as a material for forming a protective layer of an electrophotographic photoreceptor used in, for example, a copier or a printer.
  • the present invention also relates to an electrophotographic photoreceptor using this compound.
  • the photoconductor In printers and copiers, when a charged organic photoconductor (OPC) drum is irradiated with light, that part is discharged and an electrostatic latent image is created, and an image can be obtained by attaching toner to the electrostatic latent image.
  • OPC organic photoconductor
  • the photoconductor In devices that use electrophotography in this way, the photoconductor is the core material.
  • the charging method of the photoreceptor includes a negative charging method in which the surface of the photoreceptor is negatively charged, and a positive charging method in which the surface of the photoreceptor is positively charged.
  • a negative charging method in which the surface of the photoreceptor is negatively charged
  • a positive charging method in which the surface of the photoreceptor is positively charged.
  • a "positively charged single-layer photoreceptor” generally has a structure in which an undercoat layer (UCL) made of resin or the like is provided on a conductive substrate such as an aluminum tube, and a single-layer photosensitive layer made of a charge generating material (CGM), a hole transport material (HTM), an electron transport material (ETM), and a resin or the like is provided on top of that (see, for example, Patent Document 1).
  • UCL undercoat layer
  • CGM charge generating material
  • HTM hole transport material
  • ETM electron transport material
  • a photoreceptor As a technique for improving the mechanical strength or abrasion resistance of the photoreceptor surface, a photoreceptor has been disclosed in which a layer containing a compound having a chain-polymerizable functional group as a binder resin is formed in the outermost layer of the photoreceptor, and this is polymerized by applying energy such as heat, light, or radiation to form a cured resin layer (see, for example, Patent Documents 1 and 2).
  • Such a protective layer is generally formed by dissolving a curable composition containing a compound having a chain polymerizable functional group in an organic solvent to prepare a coating liquid for forming a protective layer, and then coating the coating liquid for forming a protective layer on the surface of the photoreceptor.
  • X represents a perylene diimide skeleton represented by formula (2).
  • a and B each represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a heteroaryloxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, a dialkylamino group which may have a substituent, a diarylamino group which may have a substituent, an arylalkylamino group which may have a substituent, an acyl group which may have a substituent, a haloalkyl group which may have a substituent, an alkylthio group which may have a substituent, an arylthio group which may have a substituent, a silyl group which may have a substituent, a siloxy group which may have a substituent, an aromatic hydrocarbon group which may have a substituent,
  • G 1 to G 8 each independently represent a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group which may have a substituent, or an alkoxy group which may have a substituent, provided that at least one of G 1 to G 8 is a halogen atom.
  • * represents a bond to A or B.
  • L 1 and L 2 each independently represent a direct bond or a divalent group.
  • Z represents a hydrogen atom, an alkyl group, an alkoxy group, an amide group, or a polymerizable functional group.
  • x1+y1 3, x1 is an integer from 0 to 2
  • y1 is an integer from 1 to 3
  • x2+y2 3, x2 is an integer from 0 to 2
  • y2 is an integer from 1 to 3
  • R1 may be the same or different from each other, when y1 is an integer of 2 or more
  • R2 , x2, y2, L1 , L2 and Z may be the same or different from each other, when x2 is an integer of 2 or more
  • R2 may be the same or different from each other, when y2 is an integer of 2 or more
  • L2 and Z may be the same or different from each other.
  • L3 represents a direct bond or a divalent group.
  • R3 represents a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a heteroaryloxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, a dialkylamino group which may have a substituent, a diarylamino group which may have a substituent, an arylalkylamino group which may have a substituent, an acyl group which may have a substituent, a haloalkyl group which may have a substituent, an alkylthio group which may have a substituent, an arylthio group which may have a substituent, a silyl group which may have a substituent, a siloxy group
  • R 110 represents a hydrogen atom or an alkyl group which may have a substituent, and * represents the bonding position.
  • the compound according to the second embodiment of the present invention is a compound having at least one structure represented by the following formula (3A) (hereinafter also referred to as "linking group (3A)”) in one molecule, and having a halogenated perylene diimide skeleton, which is an electron transport skeleton, represented by the following formula (1).
  • G 1 to G 8 each independently represent a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group which may have a substituent, or an alkoxy group which may have a substituent.
  • G 1 to G 8 may further represent a group represented by the following formula (3B), with the proviso that at least one of G 1 to G 8 is a halogen atom. * represents a bond to A or B.
  • the halogen-containing perylene diimide skeleton represented by formula (2) preferably has at least two halogen atoms, and more preferably has at least four halogen atoms.
  • R 1 and R 2 each independently represent a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a heteroaryloxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, a dialkylamino group which may have a substituent, a diarylamino group which may have a substituent, an arylalkylamino group which may have a substituent, an acyl group which may have a substituent, a haloalkyl group which may have a substituent, an alkylthio group which may have a substituent, an arylthio group which may have a substituent, a silyl group which may have a substituent, a siloxy group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group
  • R 1 and R 2 may further be a group represented by the formula (3B).
  • R 1 is preferably an alkyl group which may have a substituent
  • R 2 is preferably a hydrogen atom.
  • L 1 and L 2 each independently represent a direct bond or a divalent group.
  • Z represents a hydrogen atom, an alkyl group, an alkoxy group, an amide group, or a polymerizable functional group.
  • y1 is preferably 1 or 2, and therefore x1 is preferably 2 or 1.
  • R1 is preferably a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, or an acyl group which may have a substituent, more preferably an alkyl group which may have a substituent, and further preferably the alkyl group is a linear or branched alkyl group having 4 or more carbon atoms.
  • the two R 1 are each independently a hydrogen atom, a linear or branched alkyl group, an alkoxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, or an acyl group which may have a substituent, and it is more preferable that one R 1 is a hydrogen atom and the other R 1 is a linear or branched alkyl group having 4 or more carbon atoms.
  • L 1 and L 2 each independently represent a direct bond or a divalent group.
  • L 1 and L 2 each independently represent an alkylene group, a divalent group having a ketone group, a divalent group having an ether bond, a divalent group having an ester bond, or a group formed by linking these together, more preferably an alkylene group, a divalent group having an ether bond, a divalent group having an ester bond, or a group formed by linking these together, and particularly preferably an alkylene group or a divalent group having an ester bond.
  • the divalent group which L1 and L2 can take is preferably an alkylene group, a divalent group having a ketone group, a divalent group having an ether bond, a divalent group having an ester bond, or a group in which these are linked (among these, the linking group (3A) is included in the group in which an alkylene group and an ester group are linked).
  • L1 and L2 are both a linking group (3A).
  • n is an integer of 1 or more, preferably 2 or more, and more preferably 8 or less, more preferably 4 or less. When n is equal to or more than the lower limit, the solubility in organic solvents is excellent. When n is equal to or less than the upper limit, the electron transport property is excellent.
  • the compound according to the first embodiment of the present invention has two or more polymerizable functional groups. If the compound has two or more polymerizable functional groups, it is possible to form a protective layer having excellent mechanical strength by polymerizing and curing the compound during the formation of the protective layer, which is preferable.
  • the compound according to the first embodiment of the present invention may have two or more polymerizable functional groups, but from the viewpoints of solubility in an organic solvent and curability, the number of polymerizable functional groups is preferably three or more, and more preferably four or more. On the other hand, from the viewpoint of the stability of the compound, the number of polymerizable functional groups possessed by the compound of the present invention is preferably 12 or less, more preferably 10 or less, and more preferably 8 or less.
  • the compound according to the second embodiment of the present invention preferably has at least one polymerizable functional group.
  • the polymerizable functional group By having the polymerizable functional group, it is possible to form a protective layer having excellent mechanical strength.
  • the number of polymerizable functional groups possessed by the compound according to the second embodiment of the present invention is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more.
  • the number of polymerizable functional groups possessed by the compound according to the second embodiment of the present invention is preferably 12 or less, more preferably 10 or less, and more preferably 8 or less.
  • the polymerizable functional group is preferably one of the formulae (M1), (M2), and (M4) to (M7), and more preferably one of the formula (M1) or (M2), from the viewpoints of chemical stability, polymerization reactivity, and hardness of the film after film formation.
  • R 110 represents a hydrogen atom or an alkyl group which may have a substituent, and * represents the bonding position.
  • the compounds of the present invention can be produced, for example, according to the methods described in the Examples below.
  • the compound of the present invention has excellent solubility in organic solvents, particularly alcoholic solvents and mixed solvents containing alcoholic solvents, and is preferably soluble in a mixed solvent of toluene and 2-propanol (toluene 30% by mass, 2-propanol 70% by mass) at a concentration of 3% by mass or more, particularly preferably 6% by mass or more.
  • the compound of the present invention is useful as a protective layer-forming material for an electrophotographic photoreceptor due to its excellent electron transport property and solubility in an organic solvent.
  • the compound can also be used not only as a protective layer-forming material but also as a photosensitive layer-forming material and an undercoat layer-forming material for an electrophotographic photoreceptor, or for applications other than materials for electrophotographic photoreceptors, such as materials for organic electroluminescent elements and materials for organic thermoelectric conversion elements.
  • composition of the present invention contains the above-mentioned compound of the present invention, and is particularly useful as a curable composition used in preparing a coating liquid for forming a protective layer of an electrophotographic photoreceptor.
  • the present composition will be described below by taking as examples curable compositions used in the preparation of a coating liquid for forming a protective layer for an electrophotographic photoreceptor, but the present composition is not limited to such curable compositions.
  • the composition contains an electron transporting compound including at least the compound of the present invention, and optionally contains a polymerizable compound not having an electron transporting skeleton, an electron donor compound, a polymerization initiator, inorganic particles, and other materials.
  • the term "composition” refers to a composition that is made up of only solid components that do not contain a solvent. Therefore, the content of each component, such as the compound of the present invention, in 100 parts by mass of the composition described below corresponds to the content of each component in 100 parts by mass of the total mass of the protective layer formed using the composition.
  • the total mass of the protective layer means the total mass of the protective layer after curing, that is, the total mass of the solid content in the coating liquid for forming the protective layer, which will be described later.
  • the electron transporting compound contained in the present composition includes at least the compound of the present invention, and may contain an electron transporting compound other than the compound of the present invention as necessary.
  • the composition may contain only one type of the compound of the present invention, or may contain two or more types.
  • the composition of the present invention may contain only one type, or may contain two or more types.
  • the content of the electron transport compound in the composition is preferably 40 parts by mass or more, more preferably 50 parts by mass or more, and even more preferably 60 parts by mass or more, relative to 100 parts by mass of the total mass of the composition, while from the viewpoint of the hardness and elastic deformation rate of the protective layer, the content is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 70 parts by mass or less.
  • the content of the compound of the present invention is preferably 40 parts by mass or more, more preferably 50 parts by mass or more, and even more preferably 60 parts by mass or more, relative to 100 parts by mass of the total mass of the electron transporting compounds in the composition, and may be 100 parts by mass.
  • the present composition may contain a polymerizable compound that does not have an electron transporting skeleton.
  • a composition using them does not contain a polymerizable compound having no electron transport skeleton, it can form a protective layer with good curability by the method described below, but by using a polymerizable compound having no electron transport skeleton in addition to the compound of the present invention, the mechanical strength of the protective layer formed can be more sufficiently obtained.
  • the polymerizable compound without an electron transport backbone may be any compound having a chain polymerizable functional group.
  • a monomer, oligomer, or polymer having a radical polymerizable functional group is preferred.
  • a curable compound having crosslinking properties, particularly a photocurable compound is preferred.
  • a curable compound having two or more radical polymerizable functional groups can be mentioned.
  • a compound having one radical polymerizable functional group can also be used in combination.
  • the radically polymerizable functional group may be either an acryloyl group (including an acryloyloxy group) or a methacryloyl group (including a methacryloyloxy group), or both of these groups.
  • curable compound having a radically polymerizable functional group examples include trimethylolpropane triacrylate (TMPTA), trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, glycerol triacrylate, tris(acryloxyethyl)isocyanurate, dipentaerythritol hexaacrylate, dimethylolpropane tetraacrylate, pentaerythritol ethoxy tetraacrylate, EO-modified phosphate triacrylate, 2,2,5,5-tetrahydroxymethylcyclopentanone tetraacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, polyethylene glycol diacrylate, and the like.
  • TMPTA trimethylolpropane triacrylate
  • trimethacrylate pentaerythritol triacrylate
  • acrylate polypropylene glycol diacrylate, polytetramethylene glycol diacrylate, EO-modified bisphenol A diacrylate, PO-modified bisphenol A diacrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, tricyclodecane dimethanol diacrylate, decanediol diacrylate, hexanediol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, EO-modified bisphenol A dimethacrylate, PO-modified bisphenol A dimethacrylate, tricyclodecane dimethanol dimethacrylate, decanediol dimethacrylate, hexanediol dimethacrylate, and the like.
  • examples of oligomers and polymers having an acryloyl group or a methacryloyl group include urethane acrylate, ester acrylate, acrylic acrylate, and epoxy acrylate. Among these, urethane acrylate and ester acrylate are preferred, and among these, ester acrylate is more preferred.
  • the above compounds can be used alone or in combination of two or more types.
  • the content ratio (mass ratio) of the polymerizable compound to the electron transporting compound in the present composition is preferably 1.5 or less, more preferably 1.0 or less, and even more preferably 0.75 or less, from the viewpoint of electron transportability.
  • this content ratio (mass ratio) is preferably 0.2 or more, more preferably 0.3 or more, and even more preferably 0.4 or more.
  • the composition may further contain an electron donor compound.
  • the term "electron donating compound” refers to a compound that can donate electrons to the protective layer.
  • the term “electron donating compound” refers to a compound that can reduce the energy barrier during electron transfer in a target compound (electron transporting compound) in the protective layer by any mechanism, and can inject electrons into the target compound.
  • the mechanism may be, for example, a direct transfer of electrons from the electron donating compound to the target compound, a transfer of electrons by forming a hydrogen bond between the electron donating compound and the target compound, or a reduction in the energy barrier during electron transfer by forming a hydrogen bond between the electron donating compound and the target compound, and an injection of electrons transferred from the photosensitive layer into the target compound present in the protective layer.
  • electron donating compounds include compounds having structures such as triphenylmethane, acridine, amine, amidine, aniline, pyridine, xanthene, benzimidazole, guanidine, and phosphazene. Compounds that will be recognized to have such effects in the future are also included.
  • the electron donor compound is preferably a compound having one or more heteroatoms in the molecule, and more preferably a compound having one or more nitrogen atoms (N atoms) in the molecule.
  • the number of heteroatoms in one molecule of the electron donor compound is preferably one or more, more preferably two or more, and even more preferably three or more.
  • the number of nitrogen atoms (N atoms) in one molecule of the electron donor compound is preferably one or more, more preferably two or more, and even more preferably three or more.
  • the electron donating compound is preferably a compound having one or more cyclic structures.
  • the electron donor compound is preferably an electron donor compound represented by the following formula (4) or (5).
  • These electron donor compounds are activated, for example, when heated to room temperature or higher, and can donate electrons to the protective layer.
  • the electron donor compound represented by the following formula (4) is activated when heated to about 80° C. or higher, and can donate electrons to the protective layer.
  • the electron donor compound represented by the following formula (5) is activated when heated to room temperature or higher, and can donate electrons to the protective layer.
  • these compounds are activated by the temperature rise accompanying ultraviolet irradiation, and can donate electrons to the protective layer.
  • E 1 to E 4 are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted thioalkyl group, an optionally substituted thioaryl group, an optionally substituted arylsulfonyl group, an optionally substituted amino group, an optionally substituted alkylamino group, an optionally substituted arylamino group, an optionally substituted hydroxy group, an optionally substituted alkoxy group, an optionally substituted acylamino group, an optionally substituted acyloxy group, an optionally substituted aromatic hydrocarbon group, an optionally substituted carboxy group, an optionally substituted carboxamido group, an optionally substituted carboalkoxy group, an optionally substituted acyl group, an optionally substituted sulfonyl group, an optionally substituted cyano group, an optionally substituted nitro group, or a derivative of any of these groups.
  • a halogen atom an optional
  • h is an integer of 0 or more, and from the viewpoint of stability, h is preferably 2 or less, more preferably 1 or less, and even more preferably 0.
  • Ar is preferably represented by the following formula (6):
  • G 22 is preferably an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or a halogen atom.
  • g2 is an integer of 0 or more, and from the viewpoint of stability, it is preferably 2 or less, more preferably 1 or less, and most preferably 0.
  • G21 in formula (5) is preferably a hydrocarbon group which may have a substituent.
  • the number of carbon atoms in the hydrocarbon group is preferably 1 or more, more preferably 3 or more, and is preferably 12 or less, more preferably 10 or less.
  • the hydrocarbon group is preferably an alkyl group, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a hexyl group, an octyl group, or a decyl group.
  • the hydrocarbon group is preferably an alkylene group, such as a methylene group or an ethylene group.
  • the photosensitive layer may be a single-layer type photosensitive layer that contains both a charge generating material and a charge transporting material in the same layer, or it may be a laminated type photosensitive layer that is separated into a charge generating layer and a charge transporting layer.
  • titanyl phthalocyanine such as type A, type B, or type D, chlorogallium phthalocyanine, hydroxygallium phthalocyanine, etc. are suitable.
  • the electrophotographic photoreceptor has a laminated photosensitive layer, for example, a structure in which a charge transport layer (CTL) containing a charge transport material is laminated on a charge generation layer (CGL) containing a charge generation material (CGM) can be mentioned.
  • CTL charge transport layer
  • CGL charge generation layer
  • CGM charge generation material
  • the charge generating layer (CGL) usually contains a charge generating material (CGM) and a binder resin.
  • the charge generating material (CGM) and the binder resin are the same as those described in the single-layer type photosensitive layer.
  • the compounding ratio (mass) of the charge generating substance is preferably 10 parts by mass or more, and more preferably 30 parts by mass or more, per 100 parts by mass of the binder resin.
  • the compounding ratio (mass) of the charge generating substance is preferably 1000 parts by mass or less, and more preferably 500 parts by mass or less, per 100 parts by mass of the binder resin. From the viewpoint of film strength, a ratio of 300 parts by mass or less is even more preferable, and 200 parts by mass or less is particularly preferable.
  • the charge transport layer usually contains a charge transport material and a binder resin.
  • the charge transport material and the binder resin are the same as those explained in the single-layer type photosensitive layer.
  • the charge transport material is preferably mixed in a ratio of 20 parts by weight or more to 100 parts by weight of binder resin, more preferably 30 parts by weight or more from the viewpoint of reducing residual potential, and even more preferably 40 parts by weight or more from the viewpoint of stability and charge mobility during repeated use.
  • the charge transport material is preferably mixed in a ratio of 200 parts by weight or less to 100 parts by weight of binder resin, more preferably 150 parts by weight or less from the viewpoint of compatibility between the charge transport material and the binder resin, and particularly preferably 120 parts by weight or less from the viewpoint of glass transition temperature.
  • the thickness of the charge transport layer is not particularly limited. From the viewpoints of electrical characteristics, image stability, and high resolution, it is preferably 5 ⁇ m or more and 50 ⁇ m or less, more preferably 10 ⁇ m or more and 40 ⁇ m or less, and even more preferably 15 ⁇ m or more and 35 ⁇ m or less.
  • solvent or dispersion medium used to prepare the coating liquid.
  • Specific examples include alcohols, ethers, aromatic hydrocarbons, and chlorinated hydrocarbons. These may be used alone or in any combination of two or more of any type.
  • the amount of the solvent or dispersion medium used is not particularly limited. Taking into consideration the purpose of each layer and the properties of the selected solvent or dispersion medium, it is preferable to appropriately adjust the solid content concentration, viscosity, and other physical properties of the coating liquid so that they fall within the desired range.
  • the coating film is preferably dried to the touch at room temperature, and then heated and dried for 1 minute to 2 hours at a temperature in the range of 30° C. to 200° C., either stationary or with a fan.
  • the heating temperature may be constant, or the temperature may be changed during drying.
  • the conductive support of the present electrophotographic photoreceptor (hereinafter also referred to as "the present conductive support”) is not particularly limited as long as it supports a layer formed thereon and exhibits electrical conductivity.
  • the conductive support that can be used include metal materials such as aluminum, aluminum alloys, stainless steel, copper, and nickel; resin materials to which electrical conductivity has been imparted by the coexistence of conductive powders such as metal, carbon, and tin oxide; and resins, glass, and paper to which a conductive material such as aluminum, nickel, or ITO (indium oxide tin oxide) has been vapor-deposited or applied on the surface.
  • the conductive support may be in the form of a drum, cylinder, sheet, belt, or the like.
  • the conductive support may be a conductive support made of a metal material on which a conductive material having an appropriate resistance value is applied in order to control the conductivity and surface properties or to cover defects.
  • the metal material When using a metal material such as an aluminum alloy as the conductive support, the metal material may be anodized before use.
  • the present electrophotographic photoreceptor may have an undercoat layer (also referred to as “the present undercoat layer”) between the present conductive support and the present photosensitive layer in order to improve adhesion, blocking properties, and the like.
  • an undercoat layer also referred to as "the present undercoat layer”
  • organic pigments used in the undercoat layer include phthalocyanine pigments, azo pigments, and perylene pigments. Among them, phthalocyanine pigments and azo pigments, specifically, the phthalocyanine pigments and azo pigments used as the charge generating material described above, can be mentioned.
  • this undercoat layer can be selected as desired. In view of the characteristics of the electrophotographic photoreceptor and the coatability of the dispersion liquid, it is preferably 0.1 ⁇ m or more, and more preferably 20 ⁇ m or less.
  • the present electrophotographic photoreceptor may have other layers as necessary in addition to the above-mentioned present conductive support, present photosensitive layer, present protective layer and present undercoat layer.
  • the electrophotographic photoreceptor preferably has a potential retention rate of 60% or more, more preferably 70% or more, and even more preferably 80% or more.
  • the potential retention rate (dark decay, DDR) of a photoconductor means the surface potential retention rate (%) when a photoconductor with a charged surface is left for a certain period of time.
  • the potential holding rate can be measured by the method described in the Examples below.
  • the present electrophotographic photoreceptor can be used to configure an image forming apparatus (hereinafter, also referred to as "the present image forming apparatus").
  • the image forming apparatus is configured with the electrophotographic photoreceptor 1, a charging device 2, an exposure device 3, and a developing device 4, and may further include a transfer device 5, a cleaning device 6, and a fixing device 7 as necessary.
  • the electrophotographic photoreceptor 1 is not particularly limited as long as it is the electrophotographic photoreceptor described above.
  • FIG. 1 shows a drum-shaped photoreceptor in which the above-mentioned photosensitive layer is formed on the surface of a cylindrical conductive support.
  • a charging device 2, an exposure device 3, a developing device 4, a transfer device 5, and a cleaning device 6 are arranged along the outer circumferential surface of the electrophotographic photoreceptor 1.
  • the charging device 2 may be a non-contact corona charging device such as a corotron or scorotron, or a contact-type charging device (direct-type charging device) that charges the photoconductor surface by contacting a charging member to which a voltage is applied.
  • Examples of contact charging devices include a charging roller and a charging brush. Note that FIG. 1 shows a roller-type charging device (charging roller) as an example of the charging device 2.
  • the exposure device 3 is not particularly limited in type as long as it can expose the electrophotographic photoreceptor 1 to light and form an electrostatic latent image on the photosensitive surface of the electrophotographic photoreceptor 1 . Moreover, the exposure may be performed by an internal exposure method of the photoconductor.
  • the type of toner T is arbitrary, and in addition to powder toner, polymerized toner produced using methods such as suspension polymerization and emulsion polymerization can be used.
  • transfer device 5 There are no particular limitations on the type of transfer device 5, and any type of device can be used, including electrostatic transfer methods such as corona transfer, roller transfer, and belt transfer, pressure transfer, and adhesive transfer.
  • the cleaning device 6 There is no particular limitation on the cleaning device 6.
  • any cleaning device can be used, such as a brush cleaner, a magnetic roller cleaner, a blade cleaner, etc. If there is little or almost no toner remaining on the photoreceptor surface, the cleaning device 6 may not be necessary.
  • the image forming apparatus may be configured to perform, for example, a charge removal process.
  • the image forming device may be further modified, for example, to perform processes such as a pre-exposure process and an auxiliary charging process, to perform offset printing, or even to be configured as a full-color tandem system using multiple types of toner.
  • the electrophotographic photoreceptor 1 can be combined with one or more of a charging device 2, an exposure device 3, a developing device 4, a transfer device 5, a cleaning device 6 and a fixing device 7 to form an integrated cartridge (referred to as "the electrophotographic cartridge").

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  • Spectroscopy & Molecular Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Indole Compounds (AREA)
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