WO2024143484A1 - 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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WO2024143484A1
WO2024143484A1 PCT/JP2023/046985 JP2023046985W WO2024143484A1 WO 2024143484 A1 WO2024143484 A1 WO 2024143484A1 JP 2023046985 W JP2023046985 W JP 2023046985W WO 2024143484 A1 WO2024143484 A1 WO 2024143484A1
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substituent
integer
formula
compound
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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 US19/250,023 priority patent/US20260049081A1/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
    • G03G15/00—Apparatus for electrographic processes using a charge pattern
    • G03G15/14—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base
    • G03G15/16—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base of a toner pattern, e.g. a powder pattern, e.g. magnetic transfer
    • G03G15/1665—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base of a toner pattern, e.g. a powder pattern, e.g. magnetic transfer by introducing the second base in the nip formed by the recording member and at least one transfer member, e.g. in combination with bias or heat
    • G03G15/167—Apparatus for electrographic processes using a charge pattern for transferring a pattern to a second base of a toner pattern, e.g. a powder pattern, e.g. magnetic transfer by introducing the second base in the nip formed by the recording member and at least one transfer member, e.g. in combination with bias or heat at least one of the recording member or the transfer member being rotatable during the transfer
    • 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
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/0648—Heterocyclic compounds containing two or more hetero rings in the same ring system containing two relevant rings
    • 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
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G03G5/0651—Heterocyclic compounds containing two or more hetero rings in the same ring system containing four relevant rings
    • 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
    • G03G5/14734—Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides
    • 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
    • G03G5/14795—Macromolecular compounds characterised by their physical properties
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G2215/00—Apparatus for electrophotographic processes
    • G03G2215/16—Transferring device, details
    • G03G2215/1647—Cleaning of transfer member
    • G03G2215/1657—Cleaning of transfer member of transfer drum

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.
  • This type of organic photoreceptor has a large range of material selection and the characteristics of the photoreceptor are easy to control, so that "functionally separated photoreceptors" in which the functions of generating and transporting charges are shared by different compounds have become mainstream.
  • a single-layer electrophotographic photoreceptor (hereinafter referred to as a "single-layer photoreceptor") having a charge generating material (CGM) and a charge transport material (CTM) in the same layer
  • CGM charge generating material
  • CTM charge transport material
  • multi-layer photoreceptor multi-layer electrophotographic photoreceptor formed by stacking a charge generating layer containing a charge generating material (CGM) and a charge transport layer containing a charge transport material (CTM) are known.
  • 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
  • the surface of the photoconductor is first charged using corona discharge or contact methods, and then the photoconductor is exposed to light to neutralize the surface charge, forming an electrostatic latent image due to the potential difference with the surrounding surface.
  • Toner is then brought into contact with the photoconductor surface to form a toner image that corresponds to the electrostatic latent image, which is then transferred to paper or other material and heated to melt and fix it, completing the print.
  • the basic structure of an electrophotographic photoreceptor is a photosensitive layer formed on a conductive support, but a protective layer may also be provided on the photosensitive layer to improve abrasion resistance, etc.
  • 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.
  • a protective layer to improve the abrasion resistance of a photoreceptor.
  • a protective layer using a curable compound is particularly excellent in mechanical strength and can provide a good protective effect.
  • the protective layer is required to have good electron transport properties as well as mechanical strength.
  • An object of the fifth and sixth embodiments of the present invention is to provide an electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support, which is excellent in electrical properties such as potential retention rate and surface flatness, and further, has excellent solubility in an organic solvent of an electron transport compound used in forming the protective layer.
  • the present inventors have found that by using two types of compounds having a conjugated skeleton, such as a benzenediimide skeleton, a naphthalene diimide skeleton, or a perylene diimide skeleton, as the electron transport compound forming the protective layer, at least one of which has at least two polymerizable functional groups, it is possible to produce a photoreceptor having excellent electrical properties such as potential retention and excellent surface flatness, and further, by using these compounds in combination, the photoreceptor has excellent solubility in organic solvents.
  • the present invention has been achieved based on these findings, and has the following gist.
  • R1 and R2 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
  • 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.
  • R 110 represents a hydrogen atom or an alkyl group which may have a substituent, and * represents a bonding position.
  • 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,
  • L1 and L2 each independently represent a direct bond or a divalent group, provided that at least one of L1 and L2 is a divalent group represented by the following formula (3A).
  • Z represents a hydrogen atom, an alkyl group, an alkoxy group, an amide group, or a polymerizable functional group.
  • R 1 is an alkyl group which may have a substituent.
  • a composition comprising a compound according to any one of [1] to [4] and a polymerizable compound that does not have an electron transport skeleton.
  • composition according to [5] further comprising an electron donor compound.
  • An electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support,
  • the protective layer has one or more polymerizable functional groups in one molecule and contains a polymer of a compound represented by the following formula (1):
  • a and B in formula (1) 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, an aromatic heterocyclic group which may have a substituent
  • a 1 , B 1 , A 2 , and B 2 are each preferably independently 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, an acyl group which may have a substituent, or a group represented by formula (3), more preferably an alkoxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, an acyl group which may have a substituent, or a group represented by formula (3), and particularly preferably a group represented by formula (3).
  • A1 and B1 may be the same or different from each other, but are preferably the same from the viewpoints of solubility in an organic solvent and curability.
  • A2 and B2 may be the same or different from each other, but are preferably the same from the viewpoints of solubility in an organic solvent and curability.
  • 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.
  • y2 is preferably 2, and therefore x2 is preferably 1.
  • the polymerizable functional group is preferably one of the formulae (M1), (M2), and (M4) to (M7), and more preferably one of the formulae (M1) or (2), from the viewpoints of chemical stability, polymerization reactivity, and hardness of the film after film formation.
  • the compounds of the present invention can be produced, for example, according to the methods described in the Examples below.
  • composition of the present invention contains the above-mentioned compound (1) of the present invention, or the compound (1A) and the compound (1B), and is particularly useful as a curable composition used in the preparation of 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 (1) of the present invention, or the compound (1A) and the compound (1B), and, as necessary, 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 compound (1) of the present invention, or compound (1A) and compound (1B), and may contain an electron transporting compound other than compound (1) of the present invention, or compound (1A) and compound (1B) as necessary.
  • the present composition may contain only one type of compound (1) of the present invention, or may contain two or more types.
  • the composition may contain only one type of compound (1A) or two or more types of compound (1B).
  • the compound (1A) and the compound (1B) in this composition are distinguished as follows. That is, when the composition contains a compound satisfying the above formulas (1A) and (1B) and having a polymerizable functional group and a compound not having a polymerizable functional group, the compound having a polymerizable functional group is compound (1A), and the compound not having a polymerizable functional group is compound (1B).
  • the present composition contains two compounds that satisfy the above formulas (1A) and (1B) and both have polymerizable functional groups, the compound having the greater number of polymerizable functional groups can be called compound (1A), and the compound having the fewer number of polymerizable functional groups can be called compound (1B).
  • the compound with a relatively higher electron transporting property can be designated as compound (1A) and the compound with a relatively lower electron transporting property can be designated as compound (1B) depending on the presence or absence of halogen atoms in G to G in formulas (11) to (13) and differences in the functional groups constituting formula (3).
  • the compound having a relatively larger molecular weight can be compound (1A) and the compound having a relatively smaller molecular weight can be compound (1B).
  • the content ratio of compound (1A) and compound (1B) is not particularly limited; however, in order to effectively obtain the effects of the present invention, such as improved solubility in organic solvents, which is achieved by mixing and using these compounds, the content ratio, in mass ratio, of compound (1A):compound (1B) is preferably 100:100 to 1, more preferably 100:100 to 30, and even more preferably 100:100 to 50.
  • the content ratio of compound (1A) and compound (1B) in the composition of the present invention corresponds to the content ratio of polymer (1), which is a polymer of compound (1A), and compound (1B) or a polymer or copolymer thereof in the protective layer described below.
  • Examples of electron transport compounds other than the compound according to the first embodiment contained in the composition include the compounds shown below.
  • Examples of electron transport compounds other than the compound according to the third embodiment contained in the composition include the compounds shown below.
  • examples of the electron transporting compound other than the compound (1A) and the compound (1B) include the compounds shown below.
  • 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.
  • the content of the electron transport compound in the composition 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 transport skeleton.
  • the present protective layer described below contains a polymer of a polymerizable compound that does not have an electron transport skeleton.
  • compounds having a polymerizable functional group can also function as a curable compound.
  • a protective layer can be formed with good curability by the method described below.
  • the mechanical strength of the protective layer that is formed can be obtained even more sufficiently.
  • 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.
  • 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 content of the polymerizable compound not having an electron transport skeleton in the composition corresponds to the content of the polymer in the protective layer described below.
  • the present composition may further contain an electron donating compound.
  • the present protective layer described below contains the electron donating 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.
  • examples of electron donating compounds include compounds having structures such as triphenylmethane, acridine, amine, amidine, aniline, pyridine, xanthene, benzimidazole, guanidine, and phosphazene.
  • compounds having a benzimidazole structure or a guanidine structure are preferred from the viewpoint of stability.
  • the guanidine structure either a chain guanidine structure or a cyclic guanidine structure can be used, but from the viewpoint of stability, a cyclic guanidine structure is preferred.
  • the protective layer is the outermost layer, that is, the outermost layer located on the opposite side to the conductive support.
  • the effect of the present invention can be obtained even if the protective layer is not necessarily the outermost layer.
  • the effect can be obtained even if the protective layer is not the outermost layer.
  • the coating film After forming the coating film by the above coating method, the coating film is dried. In this case, the temperature and time of drying are not important as long as necessary and sufficient drying is obtained. However, if the protective layer is applied by only air drying after applying the photosensitive layer, it is preferable to perform sufficient drying by the method described below in the method for forming the photosensitive layer.
  • 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.
  • CGM charge generating material
  • various photoconductive materials such as inorganic photoconductive materials and organic pigments can be used.
  • organic pigments are particularly preferred, and phthalocyanine pigments and azo pigments are more preferred.
  • Charge transport materials are classified into hole transport materials having mainly hole transporting ability and electron transport materials having mainly electron transporting ability.
  • the present photosensitive layer is a single-layer type photosensitive layer, it is preferable that at least a hole transport material and an electron transport material are contained in the same layer.
  • 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.
  • metal oxide particles used in the undercoat layer include metal oxide particles containing one type of metal element, such as titanium oxide, aluminum oxide, silicon oxide, zirconium oxide, zinc oxide, and iron oxide, and metal oxide particles containing multiple metal elements, such as calcium titanate, strontium titanate, and barium titanate.
  • the undercoat layer may contain only one type of particle, or multiple types of particles may be mixed in any ratio and combination.
  • 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 Martens hardness is preferably 210 N/mm2 or more , more preferably 220 N/mm2 or more, and even more preferably 240 N/ mm2 or more.
  • the Martens hardness varies depending on the component blend of the protective layer, but is preferably 175 N/ mm2 or more, more preferably 200 N/mm2 or more , and even more preferably 220 N/ mm2 or more.
  • the Martens hardness of the photoreceptor means the Martens hardness measured from the surface side of the photoreceptor. The Martens hardness can be measured by the method described in the Examples below.
  • the electrophotographic photoreceptors according to the first, second and fourth embodiments of the present invention are preferably 40.0% or more, more preferably 45.0% or more, and even more preferably 50.0% or more.
  • the electrophotographic photoreceptor according to the third embodiment of the present invention has an elastic deformation rate that, although it varies depending on the component composition of the protective layer, is preferably 25% or more, more preferably 30% or more, and even more preferably 40% or more.
  • the elastic deformation rate of the photoreceptor means the elastic deformation rate measured from the surface side of the photoreceptor. The elastic deformation rate can be measured by the method described in the Examples below.
  • the residual potential varies depending on the component composition of the protective layer, but is preferably 250 V or less, more preferably 200 V or less, even more preferably 150 V or less, and even more preferably 100 V or less.
  • the residual potential of the photoconductor means the potential of the photoconductor after it has been charged and irradiated with exposure light. The residual potential can be measured by the method described in the Examples below.
  • the potential retention rate is preferably 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 photoreceptor 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 type of toner T is arbitrary, and in addition to powder toner, polymerized toners 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").
  • the electrophotographic cartridge can be configured to be detachable from the main body of an electrophotographic device such as a copying machine or laser beam printer. In that case, for example, if the electrophotographic photoreceptor 1 or other components deteriorate, the electrophotographic photoreceptor cartridge can be removed from the main body of the image forming device and a new electrophotographic photoreceptor cartridge can be attached to the main body of the image forming device, making it easy to maintain and manage the image forming device.
  • an electrophotographic device such as a copying machine or laser beam printer.
  • electrophotographic photoreceptors were prepared by the following method, and the hardness and elastic deformation rate of the outermost protective layer were evaluated by the following method. The evaluation results are shown in Table 1.
  • a single-layer photosensitive layer-forming coating solution Q1 having a solid content concentration of 25% by mass was prepared by mixing 2.6 parts of D-type titanyl phthalocyanine which exhibits a clear peak at a diffraction angle 2 ⁇ 0.2° of 27.3° in powder X-ray diffraction using CuK ⁇ radiation, 1.3 parts of perylene pigment 1 having the structure shown below, 0.5 parts of polyvinyl butyral resin, 90 parts of the hole transport material shown below (HTM48, molecular weight 748), 70 parts of the electron transport material shown below (ET-2, molecular weight 424.2), 100 parts of a polycarbonate resin having a biphenyl structure, 0.05 parts of silicone oil (manufactured by Shin-Etsu Silicones: product name KF-96) as a leveling agent, and 793.35 parts of a mixed solvent of tetrahydrofuran (hereinafter appropriately abbreviations: a mixed solvent of tetrahydrofuran (hereinafter appropriately ab
  • Both of the comparative compounds 2 and 3 had poor solubility, so that it was not possible to prepare a coating liquid for forming a protective layer.
  • a single-layer photoreceptor was prepared according to the following procedure.
  • the coating solution Q1 for forming a single-layer type photosensitive layer was dip-coated on the undercoat layer and dried at 100° C. for 24 minutes to provide a single-layer type photosensitive layer having a thickness of 32 ⁇ m after drying.
  • the protective layer-forming coating solutions S1 to S3 were each ring-coated onto the single-layer photosensitive layer, and immediately after coating, while the photoconductor was rotated at 60 rpm under a nitrogen atmosphere, 365 nm LED light was irradiated at an intensity of 0.9 W/ cm2 for 30 seconds for photoconductor A1, at an intensity of 0.9 W/ cm2 for 60 seconds for photoconductor A2, and at an intensity of 0.9 W/ cm2 for 120 seconds for photoconductor A3, thereby providing a protective layer so that the film thickness after curing was 1.5 ⁇ m, and photoconductors AI-1 to AI-3 were produced, respectively.
  • the electrophotographic photoreceptor of the present invention has a low residual potential, excellent electrical properties, and excellent mechanical strength such as hardness and elastic deformation rate.
  • Comparative Compounds 4 and 1, which do not have a perylene diimide skeleton, are used the residual potential is high and the electrical properties are poor.
  • S Completely dissolved at room temperature.
  • A A small amount of undissolved material was observed at room temperature, but it was completely dissolved when heated at 40° C. for 10 minutes or less.
  • B Some of the material remained undissolved at room temperature, but was completely dissolved when heated at 40° C. for 10 minutes or more.
  • C When heated at 40° C. for 10 minutes or more, residual material was observed.
  • a coating liquid Q1 for forming a single-layer type photosensitive layer was prepared in the same manner as in ⁇ Preparation of coating liquid Q1 for forming a single-layer type photosensitive layer> in [[First Example]].
  • a single-layer photoreceptor was prepared according to the following procedure.
  • the coating solution Q1 for forming a single-layer photosensitive layer was dip-coated on the undercoat layer, and dried at 100° C. for 24 minutes, so that a single-layer photosensitive layer was provided with a film thickness of 32 ⁇ m after drying.
  • the potential retention rate was measured by the following method.
  • the toner was attached to an electrophotographic property evaluation device manufactured in accordance with the measurement standard of the Society of Electrophotography (described in "Continued Fundamentals and Applications of Electrophotographic Technology," edited by the Society of Electrophotography, Corona Publishing, pp. 404-405), and the electrical properties were measured by a cycle of charging, exposure, potential measurement, and static elimination as follows.
  • the dark decay (DDR) after charging to +700 V and leaving for 5 seconds was measured (%).
  • the measurement was performed in an environment of a temperature of 25° C. and a relative humidity of 50% (N/N environment).

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