JP2015102632A - Electrophotographic photoreceptor, method of producing electrophotographic photoreceptor, process cartridge and electrophotographic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor having a surface layer comprising a polymer of a charge transporting compound having a polymerizable functional group, the electrophotographic photoreceptor inhibiting image deletion, and a method of producing the same.SOLUTION: A surface layer of an electrophotographic photoreceptor comprises a polymer of a charge transporting compound having a univalent polymerizable functional group represented by a formula (1).

Description

  The present invention relates to an electrophotographic photosensitive member, a method for manufacturing an electrophotographic photosensitive member, a process cartridge, and an electrophotographic apparatus.

  An electrophotographic photosensitive member that is repeatedly used in an electrophotographic apparatus is required to have high wear resistance.

  Patent Document 1 discloses a technique for improving the abrasion resistance of an electrophotographic photosensitive member by adding a polymer obtained by polymerizing a charge transporting compound having a polymerizable functional group to the surface layer of the electrophotographic photosensitive member. Have been described. Patent Document 1 describes that an acryloyloxy group and a methacryloyloxy group are particularly preferable as the polymerizable functional group.

  On the other hand, as the abrasion resistance of the electrophotographic photosensitive member increases, the surface of the electrophotographic photosensitive member becomes difficult to be refreshed, and a material that has undergone a chemical change due to repeated use tends to remain on the surface of the electrophotographic photosensitive member. . It is thought that chemical changes in the materials constituting the surface of electrophotographic photoreceptors are mainly caused by the adhesion of discharge products generated by the charging process accompanied by discharge and the cleavage and oxidation of the molecular chains of the material caused by the discharge. ing.

JP 2000-066425 A

  If removal of a substance that has caused a chemical change is insufficient and the charge transporting compound is chemically changed (denatured), image flow is likely to occur in a high-temperature and high-humidity environment. In particular, in an electrophotographic photosensitive member in which a material that has undergone a chemical change due to repeated use is accumulated, when image formation is resumed after pausing image formation, the rubbing behavior of the cleaning member (cleaning blade, etc.) Tends to become unstable, and image flow tends to occur. A method for increasing the surface temperature of the electrophotographic photosensitive member by installing a heating means (drum heater) for the electrophotographic photosensitive member in order to suppress image flow due to chemical changes in the material constituting the surface of the electrophotographic photosensitive member. Is used. However, from the viewpoint of energy saving of the electrophotographic apparatus, there is a demand for an electrophotographic photosensitive member that suppresses image flow without using the above-described heating means.

  An object of the present invention is to provide an electrophotographic photosensitive member having a surface layer containing a polymer of a charge transporting compound having a polymerizable functional group, and an electrophotographic photosensitive member that suppresses image flow, and a method for producing the same. It is in.

  Another object of the present invention is to provide a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

The present invention relates to an electrophotographic photosensitive member having a support and a photosensitive layer formed on the support,
The electrophotographic photoreceptor includes an electrophotographic photoreceptor, wherein the surface layer of the electrophotographic photoreceptor contains a polymer of a charge transporting compound having a monovalent polymerizable functional group represented by the following formula (1).

(In Formula (1), R ¹ represents a fluorine atom or an alkyl group having a fluorine atom. R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group.)
The present invention also provides a method for producing an electrophotographic photosensitive member for producing the electrophotographic photosensitive member, wherein the manufacturing method comprises:
Forming a coating film of the surface layer coating solution containing the charge transporting compound, and
The present invention relates to a method for producing an electrophotographic photoreceptor, comprising a step of forming a surface layer by polymerizing the charge transporting compound in the coating film.

  Further, the present invention integrally supports the electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means, a transfer means, and a cleaning means, and is detachable from the main body of the electrophotographic apparatus. The present invention relates to a process cartridge.

  The present invention also relates to an electrophotographic apparatus comprising the electrophotographic photosensitive member, and a charging unit, an exposing unit, a developing unit, and a transfer unit.

  According to the present invention, there are provided an electrophotographic photosensitive member having a surface layer containing a polymer of a charge transporting compound having a polymerizable functional group, and an electrophotographic photosensitive member that suppresses image flow, and a method for producing the same. Can do.

  Further, according to the present invention, a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member can be provided.

1 is a diagram illustrating an example of a schematic configuration of an electrophotographic apparatus including a process cartridge having an electrophotographic photosensitive member. It is a figure which shows an example of the layer structure of an electrophotographic photoreceptor. It is a figure explaining the halftone image of 1 dot Keima pattern.

  The present invention is characterized in that the surface layer of the electrophotographic photosensitive member contains a polymer (cured product) of a charge transporting compound having a monovalent polymerizable functional group represented by the following formula (1). The charge transporting compound is a compound having charge transporting ability.

In the above formula (1), R ¹ represents a fluorine atom or an alkyl group having a fluorine atom (fluorinated alkyl group). R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group. * Shows the side couple | bonded with the structure which has a charge transport ability of a charge transport compound.

  By having the above characteristics, the electrophotographic photosensitive member of the present invention suppresses the occurrence of image flow when the image formation is resumed after the image formation is paused. The inventors presume the reason as follows.

  In the charge transporting compound having an acryloyloxy group or a methacryloyloxy group, the charge transporting compounds are polymerized to form a polymer.

  However, it is considered that the α-position carbon atom (the carbon atom indicated as “α” below) is easily cleaved by discharge deterioration due to the bond formed by the polymerization reaction of the acryloyloxy group or methacryloyloxy group. It is presumed that radicals are generated by this cleavage, or that the cleavage site is oxidized with ozone or nitrogen oxide (NOx), so that surface charges are easily diffused, and as a result, image flow occurs.

Therefore, as a result of further studies, the present inventors can suppress the occurrence of image blur by making R ¹ in the above formula (1) a fluorine atom or an alkyl group having a fluorine atom. It was. This is presumably because the bond energy between the carbon and fluorine atoms is strong, so that the bond formed by the polymerization reaction, that is, the bond between the carbon atom bonded to R ¹ and the adjacent carbon atom is difficult to cleave. Further, it is presumed that the oxidation reaction hardly occurs due to the strong electron withdrawing property of the fluorine atom. Thereby, it is considered that the chemical change of the charge transporting compound is suppressed, and the occurrence of image blur is suppressed.

[Surface layer]
As described above, the surface layer contains a polymer of a charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1).

  From the viewpoint of suppressing the chemical change of the charge transporting compound, among the charge transporting compounds having a monovalent polymerizable functional group represented by the above formula (1), monovalent polymerization represented by the following formula (2): A charge transporting compound having a functional group is preferred. The monovalent polymerizable functional group represented by the following formula (2) includes the monovalent polymerizable functional group represented by the above formula (1).

^{R 1, R 21} and ^{R 22} in the formula (2) has the same meaning as ^{R 1, R 21} and ^{R 22} in the formula (1). That is, R ¹ represents a fluorine atom or an alkyl group having a fluorine atom. R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group.

Examples of the alkyl group having a fluorine atom include —CF ₃ , —CF ₂ CF ₃ , —C (CF ₃ ) _{3 and the} like. Among these, R ¹ is preferably a fluorine atom or —CF ₃ (trifluoromethyl group). * Shows the side couple | bonded with the structure which has a charge transport ability of a charge transport compound.

Examples of the alkyl group for R ²¹ and R ²² include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. Group and the like. Among these, R ²¹ and R ²² are preferably a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group from the viewpoint that the polymerization reaction can proceed sufficiently. In particular, R ²¹ and R ²² are preferably hydrogen atoms.

  In addition, from the viewpoint of suppression of image flow and electrophotographic characteristics, the charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) is a compound represented by the following formula (3) or (4). Is preferred. A compound represented by the following formula (3) and a compound represented by the following formula (4) may be mixed.

(In the formula ^(3), Ar 1, Ar ² and Ar ⁴ each independently, .Ar ³ showing a monovalent group, or a substituted or unsubstituted aryl group represented by the following formula (M1) is A divalent group represented by the following formula (M2) or a substituted or unsubstituted arylene group, provided that at least one of Ar ^{1 to} Ar ⁴ is a monovalent group represented by the following formula (M1) Or a divalent group represented by the following formula (M2), wherein r is 0 or 1, provided that Ar ¹ , Ar ² and Ar ⁴ are a monovalent group represented by the following formula (M1). Otherwise, r is 1 and Ar ³ is a divalent group represented by the following formula (M2).)

(In formula (4), Ar ⁵ , Ar ⁶ , Ar ⁹ and Ar ¹⁰ each independently represent a monovalent group represented by the following formula (M1) or a substituted or unsubstituted aryl group. ⁷ and Ar ⁸ each independently represent a divalent group represented by the following formula (M2) or a substituted or unsubstituted arylene group, provided that at least one of Ar ^{5 to} Ar ¹⁰ represents the following formula: A monovalent group represented by (M1) or a divalent group represented by the following formula (M2): P ¹ is an oxygen atom, a cycloalkylidene group, and two phenylene groups bonded through an oxygen atom. A valent group or an ethylene group, s and t are each independently 0 or 1, provided that Ar ⁵ , Ar ⁶ , Ar ⁹ and Ar ¹⁰ are monovalent represented by the following formula (M1); Ar ⁷ is not the group of (In the case where it is not a divalent group represented by the following formula (M2), t is 1 and Ar ⁸ is a divalent group represented by the following formula (M2).)

^{(R 1, R 21} in the formula (M1), and ^{R 22, R} 1 in the formula ^{(1), R 21,} and ^{R 22} as synonymous. Formula in (M1), ^{Ar 11} represents a substituted Alternatively, it represents an unsubstituted arylene group, m is 0 or an integer of 1 or more, and * represents the side bonded to the above formula (3) or (4).

^{(R 1, R 21} in the formula (M2), and ^{R 22, R} 1 in the formula ^{(1), R 21,} and ^{R 22} as synonymous. Formula in (M2), ^{Ar 12} represents a substituted Alternatively, it represents an unsubstituted trivalent aromatic hydrocarbon group, n is 0 or an integer of 1 or more, and * represents the side bonded to the above formula (3) or (4).
Examples of the aryl group include a phenyl group, a biphenylyl group, and a fluorenyl group.

  Examples of the arylene group include a phenylene group, a biphenylylene group, a fluorenylylene group, and the like.

  Examples of the cycloalkylidene group include a cyclopropylidene group, a cyclobutylidene group, a cyclopentylidene group, a cyclohexylidene group, a cycloheptylidene group, and a cyclooctylidene group.

  Examples of the trivalent aromatic hydrocarbon group include trivalent groups derived by removing three hydrogen atoms from an aromatic hydrocarbon such as benzene, biphenyl, fluorene, and 9,9-dimethylfluorene.

  Examples of the substituent that each group may have include, for example, a carboxyl group, a cyano group, a substituted or unsubstituted amino group, a hydroxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, and a halogen atom. An atom etc. are mentioned. Examples of the substituent that the alkoxy group and the alkyl group may have include a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom. Examples of the substituent that the amino group may have include alkyl groups such as a methyl group, an ethyl group, and an n-propyl group.

In the above formula (3), at least two of Ar ^{1 to} Ar ⁴ are preferably a monovalent group represented by the above formula (M1) or a divalent group represented by the above formula (M2). . In the above formula (M1), m is preferably an integer of 2 or more and 5 or less.

In the above formula (4), at least two of Ar ^{5 to} Ar ¹⁰ are a monovalent group represented by the above formula (M1) or a divalent group represented by the above formula (M2). Is preferred. In the formula (M2), n is preferably an integer of 2 or more and 5 or less.

  In the surface layer of the electrophotographic photoreceptor, the charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) forms a polymer by using one kind or two or more kinds in combination, You may make it contain.

  The surface layer contains a polymer of a composition containing a charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1). The content of the charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) in the composition is preferably 50% by mass or more and 100% by mass or less.

  The charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) can be obtained by using, for example, a synthesis method described in Japanese Patent Application Laid-Open Nos. 2000-066425 and 2010-156835. Can be synthesized.

  Specific examples (exemplary compounds) of the charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) are shown below, but the present invention is not limited thereto.

  Among these, exemplary compounds (1-1), (1-9), (1-24), (1-27) to (1-29), (1-33) to (1-35), (1 -38), (1-40), (1-49), (1-50), (1-57), (1-58), (1-64), (1-65), (1-68) ), (1-69), (1-71) and (1-72) are preferred.

  The surface layer of the electrophotographic photosensitive member forms a coating film of a coating solution for a surface layer containing a charge transporting compound having a monovalent group represented by the above formula (1), and the above formula (1) ) To form a charge transporting compound having a monovalent group.

  Further, from the viewpoint of achieving both image flow and high polymerization efficiency, the surface layer has a charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) and a charge having an acryloyloxy group or a methacryloyloxy group. You may contain the polymer of a composition with a transportable compound. In this case, the content of the charge transporting compound having an acryloyloxy group or a methacryloyloxy group is 20% by mass or more and 50% by mass or less with respect to the total mass of the composition from the viewpoint of maintaining the effect of image blur. Preferably there is.

  Examples of the charge transporting compound having an acryloyloxy group or a methacryloyloxy group include compounds represented by the following formula (5) or (6).

In the above formula (5), Ar ³¹ , Ar ³² and Ar ³⁴ each independently represent a monovalent group represented by the following formula (M3) or a substituted or unsubstituted aryl group. Ar ³³ represents a divalent group represented by the following formula (M4) or a substituted or unsubstituted arylene group. However, at least one of Ar ^{31 to} Ar ³⁴ is a monovalent group represented by the following formula (M3) or a divalent group represented by the following formula (M4). u is 0 or 1. However, when Ar ³¹ , Ar ³² and Ar ³⁴ are not a monovalent group represented by the following formula (M3), u is 1 and Ar ³³ is a divalent group represented by the following formula (M4).

In the above formula (6), Ar ³⁵ , Ar ³⁶ , Ar ³⁹ and Ar ⁴⁰ each independently represent a monovalent group represented by the following formula (M3) or a substituted or unsubstituted aryl group. Ar ³⁷ and Ar ³⁸ each independently represent a divalent group represented by the following formula (M4) or a substituted or unsubstituted arylene group. However, at least one of Ar ^{35 to} Ar ⁴⁰ is a monovalent group represented by the following formula (M3) or a divalent group represented by the following formula (M4). X ¹ represents an oxygen atom, a cycloalkylidene group, a divalent group in which two phenylene groups are bonded via an oxygen atom, or an ethylene group. v and w are each independently 0 or 1. However, when Ar ³⁵ , Ar ³⁶ , Ar ³⁹ and Ar ⁴⁰ are not a monovalent group represented by the following formula (M3) and Ar ³⁷ is not a divalent group represented by the following formula (M4), w is 1 Ar ³⁸ is a divalent group represented by the following formula (M4).

In the above formulas (M3) and (M4), R ³¹ and R ³² represent an alkyl group. Ar ²¹ represents a substituted or unsubstituted arylene group. Ar ²² represents a substituted or unsubstituted trivalent aromatic hydrocarbon group. P ²¹ and P ²² each independently represent an acryloyloxy group or a methacryloyloxy group. * Shows the side couple | bonded with Formula (5) or (6).

  Specific examples of the compound represented by the above formula (5) or (6) are shown below.

  Further, from the viewpoint of achieving both image flow and high polymerization efficiency, the surface layer has a charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1), a polymerizable functional group, and a charge. You may contain the polymer of a composition with the compound which does not have a structure which has transport ability.

  As the compound having a polymerizable functional group and not having a structure having a charge transporting ability, the following compounds are used. Examples thereof include trimethylolpropane trimethacrylate and trimethylolpropane triacrylate.

  Various additives can be added to the surface layer. As the additive, for example, a deterioration preventing agent such as an antioxidant or an ultraviolet absorber, or a lubricant such as polytetrafluoroethylene (PTFE) particles or carbon fluoride can be used. Moreover, polymerization control agents such as polymerization reaction initiators and polymerization reaction terminators, leveling agents such as silicone oil, surfactants, and the like can also be used.

  Solvents used in the surface layer coating solution include alcohol solvents such as methanol, ethanol and propanol, ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate and butyl acetate, tetrahydrofuran, dioxane and the like. Ether solvents, 1,1,2,2,3,3,4-heptafluorocyclopentane, halogen solvents such as dichloromethane, dichloroethane, chlorobenzene, aromatic solvents such as benzene, toluene, xylene, methyl cellosolve, ethyl Examples include cellosolve solvents such as cellosolve. These solvents may be used alone or in combination of two or more.

  When the surface layer is a protective layer, the film thickness of the surface layer is preferably 2 μm or more and 20 μm or less. Moreover, when a surface layer is a charge transport layer, it is preferable that they are 5 micrometers or more and 40 micrometers or less.

  Examples of the method of polymerizing the charge transporting compound having a monovalent group represented by the above formula (1) include a method of polymerizing using heat, light (such as ultraviolet rays), or radiation (such as electron beams). . Among these, radiation is preferable, and among these radiation, an electron beam is more preferable.

  Polymerization using an electron beam is preferable because a very dense (high density) three-dimensional network structure is obtained and wear resistance is improved. Further, since the polymerization reaction is efficient in a short time, productivity is also increased. When irradiating an electron beam, examples of the accelerator include a scanning type, an electro curtain type, a broad beam type, a pulse type, and a laminar type.

  When an electron beam is used, the acceleration voltage of the electron beam is preferably 150 kV or less from the viewpoint of suppressing material property deterioration due to the electron beam without impairing the polymerization efficiency. Moreover, it is preferable that the electron beam absorbed dose in the surface of the coating film of the surface layer coating liquid is 5 kGy or more and 10 kGy or less.

  In addition, when a charge transporting compound having a monovalent polymerizable functional group represented by the above formula (1) is polymerized using an electron beam, electrons are generated in an inert gas atmosphere for the purpose of suppressing the polymerization inhibition action by oxygen. After irradiation with the wire, it is preferable to heat in an inert gas atmosphere. Examples of the inert gas include nitrogen, argon, helium and the like.

  The electrophotographic photoreceptor of the present invention is an electrophotographic photoreceptor having a support and a photosensitive layer formed on the support as described above.

  The photosensitive layer is a single layer type photosensitive layer containing a charge generation material and a charge transport material in the same layer, and a stacked type separated into a charge generation layer containing a charge generation material and a charge transport layer containing a charge transport material. (Functional separation type) photosensitive layer. In the present invention, a laminated photosensitive layer is preferred. In addition, the charge generation layer and the charge transport layer may be stacked.

  FIGS. 2A and 2B are views showing an example of the layer structure of the electrophotographic photosensitive member of the present invention. In FIGS. 2A and 2B, 101 is a support, 102 is a charge generation layer, 103 is a charge transport layer, and 104 is a protective layer (second charge transport layer). The surface layer of the electrophotographic photosensitive member is the charge transport layer 103 in FIG. 2A and the protective layer 104 in FIG.

  In the present invention, if necessary, a conductive layer or undercoat layer described later may be provided between the support and the photosensitive layer (charge generation layer, charge transport layer).

[Support]
As the support used in the electrophotographic photosensitive member, a conductive one (conductive support) is preferable. For example, a support made of metal such as aluminum, aluminum alloy, stainless steel or alloy can be used. In the case of a support made of aluminum or an aluminum alloy, an ED tube, an EI tube, or a tube obtained by cutting, electrolytic composite polishing, wet or dry honing treatment of these can also be used as the support. A support in which a thin film of a conductive material such as aluminum, an aluminum alloy, or an indium oxide-tin oxide alloy is formed on a metal support or a resin support can also be used.

  The surface of the support may be subjected to cutting treatment, roughening treatment, alumite treatment, or the like.

  A support formed by impregnating a resin or the like with conductive particles such as carbon black, tin oxide particles, titanium oxide particles, or silver particles, or a support containing a conductive resin can also be used.

[Conductive layer]
A conductive layer containing conductive particles and a binder resin may be provided between the support and the photosensitive layer or the undercoat layer described below.

  The conductive layer may be formed by forming a coating film of a coating solution for a conductive layer obtained by dispersing conductive particles together with a binder resin and a solvent, and drying and / or curing the obtained coating film. it can.

  Examples of the conductive particles include carbon particles such as carbon black, acetylene black, aluminum, nickel, iron, nichrome, copper, zinc, silver, titanium oxide, zinc oxide, tin oxide, zirconium oxide, aluminum oxide, and ITO. A metal oxide particle is mentioned. Further, the metal particles or metal oxide particles may have their surfaces treated with a surface treatment agent such as a silane coupling agent.

  Examples of the binder resin used for the conductive layer include acrylic resin, alkyd resin, epoxy resin, phenol resin, butyral resin, polyacetal, polyurethane, polyester, polycarbonate, and melamine resin.

  Examples of the solvent used in the conductive layer coating solution include ether solvents, alcohol solvents, ketone solvents, and aromatic hydrocarbon solvents.

  The thickness of the conductive layer is preferably 0.2 μm or more and 40 μm or less, and more preferably 5 μm or more and 40 μm or less.

[Undercoat layer]
An undercoat layer may be provided between the support or the conductive layer and the photosensitive layer.

  The undercoat layer can be formed by forming a coating film of an undercoat layer coating solution obtained by dissolving a binder resin in a solvent, and drying or curing the obtained coating film.

  Examples of the binder resin used for the undercoat layer include polyacrylic acid, methylcellulose, ethylcellulose, polyamide, polyimide, polyamideimide, polyamic acid, melamine resin, epoxy resin, and polyurethane.

  The conductive particles used for the undercoat layer are the same as the conductive particles used for the conductive layer described above.

  The undercoat layer may further contain semiconductive particles, an electron transporting material, and an electron accepting material.

  Examples of the solvent used in the coating solution for the undercoat layer include ether solvents, alcohol solvents, ketone solvents, aromatic hydrocarbon solvents, and the like.

  The thickness of the undercoat layer is preferably 0.05 μm or more and 40 μm or less, and more preferably 0.4 μm or more and 20 μm or less.

(Photosensitive layer)
A photosensitive layer (charge generation layer, charge transport layer) is formed on the support, the conductive layer, or the undercoat layer.

  In the case of a laminated photosensitive layer, the charge generation layer is formed by mixing a charge generation material and a binder resin with a solvent and applying a coating solution for charge generation layer obtained by dispersion treatment to form a coating film. It can be formed by drying the coating film. The charge generation layer may be a vapor generation film of a charge generation material.

  Examples of charge generating materials used in electrophotographic photoreceptors include pyrylium, thiapyrylium dyes, phthalocyanine compounds, anthanthrone pigments, dibenzpyrenequinone pigments, pyranthrone pigments, azo pigments, indigo pigments, quinacridone pigments, and quinocyanine pigments. Can be mentioned. Among these, gallium phthalocyanine is preferable. Furthermore, hydroxygallium phthalocyanine is preferable from the viewpoint of high sensitivity. Among these, hydroxygallium phthalocyanine crystals having peaks at 7.4 ° ± 0.3 ° and 28.2 ° ± 0.3 ° of the Bragg angle 2θ in CuKα characteristic X-ray diffraction are preferable.

  Examples of the binder resin used for the charge generation layer include polycarbonate, polyester, butyral resin, polyvinyl acetal, acrylic resin, vinyl acetate resin, urea resin, and the like. Among these, a butyral resin is preferable. These resin may use only 1 type and may use 2 or more types together as a mixture or a copolymer.

  In the charge generation layer, the ratio of the charge generation material to the binder resin is preferably 0.3 parts by mass or more and 4 parts by mass or less for the binder resin with respect to 1 part by mass of the charge generation material.

  Examples of the dispersion treatment method include a method using a homogenizer, ultrasonic waves, a ball mill, a sand mill, an attritor, a roll mill, and the like.

  Examples of the solvent used in the charge generation layer coating solution include alcohol solvents, sulfoxide solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents.

  The thickness of the charge generation layer is preferably from 0.01 μm to 5 μm, and more preferably from 0.1 μm to 1 μm.

  Further, various sensitizers, antioxidants, ultraviolet absorbers, plasticizers and the like may be added to the charge generation layer.

  When the photosensitive layer is a laminated photosensitive layer, a charge transport layer is formed on the charge generation layer.

  When the charge transport layer is a surface layer as shown in FIG. 2A, the charge transport layer is formed as follows. That is, a coating film of a charge transporting layer coating liquid (surface layer coating liquid) containing a charge transporting compound having a monovalent group represented by the above formula (1) is formed, and the above formula in the coating film It can be formed by polymerizing a charge transporting compound having a monovalent group represented by (1).

  When the protective layer is a surface layer as shown in FIG. 2B, the charge transport layer (first charge transport layer) is formed as follows. That is, it can be formed by forming a coating film of a charge transport layer coating solution obtained by dissolving a charge transporting substance and a binder resin in a solvent and drying the obtained coating film.

  Hereinafter, the structure of the charge transport layer when the charge transport layer is not the surface layer will be described.

  Examples of the charge transport material used in the charge transport layer include triarylamine compounds, hydrazone compounds, stilbene compounds, pyrazoline compounds, oxazole compounds, thiazole compounds, triarylmethane compounds, and the like.

  Examples of the binder resin used for the charge transport layer include polyvinyl butyral, polyarylate, polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide, polyamide, polyvinyl pyridine, cellulose resin, urethane resin, and epoxy resin. , Agarose resin, cellulose resin, casein, polyvinyl alcohol, polyvinylpyrrolidone and the like. These binder resins may use only 1 type, and may use 2 or more types together as a mixture or a copolymer.

  The ratio of the charge transport material is preferably 30% by mass to 70% by mass with respect to the total mass of the charge transport layer.

  Examples of the solvent used in the charge transport layer coating solution include ether solvents, alcohol solvents, ketone solvents, and aromatic hydrocarbon solvents.

  The thickness of the charge transport layer is preferably 5 μm or more and 40 μm or less.

[Protective layer]
A protective layer (surface layer) may be provided on the charge transport layer. The protective layer (surface layer) is as described above.

  When applying the coating liquid for each of the above layers, a coating method such as a dip coating method (dipping method), a spray coating method, a spinner coating method, a bead coating method, a blade coating method, or a beam coating method can be used.

  FIG. 1 shows an example of a schematic configuration of an electrophotographic apparatus provided with a process cartridge having the electrophotographic photosensitive member of the present invention.

  In FIG. 2, a cylindrical (drum-shaped) electrophotographic photosensitive member 1 is rotationally driven around a shaft 2 in a direction indicated by an arrow with a predetermined peripheral speed (process speed). The surface (circumferential surface) of the electrophotographic photosensitive member 1 is positively or negatively charged by a charging unit (primary charging unit) 3 during the rotation process. Next, the surface of the electrophotographic photoreceptor 1 is irradiated with exposure light (image exposure light) 4 output from an exposure means (image exposure means) (not shown). The exposure light 4 is intensity-modulated corresponding to the time-series electric digital image signal of the target image information. Examples of exposure means include slit exposure and laser beam scanning exposure. Thus, an electrostatic latent image corresponding to the target image information is formed on the surface of the electrophotographic photoreceptor 1.

  The electrostatic latent image formed on the surface of the electrophotographic photoreceptor 1 is then developed (regular development or reversal development) with toner stored in the developing means 5 to form a toner image. The toner image formed on the surface of the electrophotographic photoreceptor 1 is transferred to the transfer material 7 by the transfer means 6. Here, when the transfer material 7 is paper, it is taken out from a paper feeding unit (not shown) in synchronization with the rotation of the electrophotographic photosensitive member 1 and fed between the electrophotographic photosensitive member 1 and the transfer means 6. Is done. Further, a bias voltage having a polarity opposite to the charge held in the toner is applied to the transfer means 6 from a bias power source (not shown). The transfer means may be an intermediate transfer type transfer means having a primary transfer member, an intermediate transfer member, and a secondary transfer member.

  The transfer material 7 onto which the toner image has been transferred is separated from the surface of the electrophotographic photosensitive member 1, transported to a fixing unit 8, and subjected to a fixing process of the toner image, whereby an electronic image forming product (print, copy) is obtained. Printed out of the photographic device.

  The surface of the electrophotographic photosensitive member 1 after the toner image is transferred is cleaned by the cleaning unit 9 to remove deposits such as transfer residual toner. The transfer residual toner can also be collected by a developing means or the like. Further, if necessary, the surface of the electrophotographic photosensitive member 1 is subjected to charge removal treatment by irradiation with pre-exposure light 10 from a pre-exposure unit (not shown), and then repeatedly used for image formation. When the charging unit 3 is a contact charging unit using a charging roller or the like, the pre-exposure unit is not always necessary.

  Among the components selected from the electrophotographic photosensitive member 1, the charging unit 3, the developing unit 5, the transfer unit 6, and the cleaning unit 9, a plurality of components may be housed in a container to form a process cartridge. Further, the process cartridge may be detachable from the main body of the electrophotographic apparatus. For example, the electrophotographic photoreceptor 1 and at least one means selected from the group consisting of charging means 3, developing means 5, transfer means 6 and cleaning means 9 are integrally supported to form a cartridge. Then, the process cartridge 11 can be detachably attached to the main body of the electrophotographic apparatus using guide means 12 such as a rail of the main body of the electrophotographic apparatus.

  Hereinafter, the present invention will be described in more detail with reference to specific examples. In the examples, “part” means “part by mass”.

<Example 1>
An aluminum cylinder having a diameter of 30 mm, a length of 357.5 mm, and a wall thickness of 1 mm was used as a support (conductive support).

Next, 100 parts of zinc oxide particles (specific surface area: 19 m ² / g, powder resistance: 4.7 × 10 ⁶ Ω · cm) are stirred and mixed with 500 parts of toluene, and 0.8 part of a silane coupling agent is added thereto. Was added and stirred for 6 hours. Thereafter, toluene was distilled off under reduced pressure, followed by heating and drying at 130 ° C. for 6 hours to obtain surface-treated zinc oxide particles. As the silane coupling agent, KBM602 (compound name: N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd. was used.

  Next, 15 parts of butyral resin (trade name: BM-1, manufactured by Sekisui Chemical Co., Ltd.) and 15 parts of blocked isocyanate (trade name: Sumijoule 3175, manufactured by Sumitomo Bayern Urethane Co., Ltd.) as polyol resin were added to methyl ethyl ketone 73. It was dissolved in a mixed solution of 5 parts and 73.5 parts of 1-butanol. 80.8 parts of surface-treated zinc oxide particles and 0.81 part of 2,3,4-trihydroxybenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to this solution, and this was added to glass beads having a diameter of 0.8 mm. Dispersion was performed for 3 hours in an atmosphere of 23 ± 3 ° C. using the sand mill apparatus used. After dispersion, 0.01 parts of silicone oil (trade name: SH28PA, manufactured by Toray Dow Corning Silicone), crosslinked polymethyl methacrylate (PMMA) particles (trade name: TECHPOLYMER SSX-103, manufactured by Sekisui Plastics Co., Ltd.) 5.6 parts of an average primary particle size of 3.0 μm) was added and stirred to prepare an undercoat layer coating solution.

  This coating solution for undercoat layer was dip-coated on a support to form a coating film, and the resulting coating film was dried at 160 ° C. for 30 minutes to form an undercoat layer having a film thickness of 18 μm.

  Next, a crystalline hydroxygallium phthalocyanine crystal (charge generation material) having strong peaks at 7.4 ° and 28.1 ° with a Bragg angle 2θ ± 0.2 ° in CuKα characteristic X-ray diffraction was prepared. 4 parts of this hydroxygallium phthalocyanine crystal and 0.04 part of the compound represented by the following formula (A) are added to 100 parts of cyclohexanone and 2 parts of polyvinyl butyral resin (trade name: ESREC BX-1, manufactured by Sekisui Chemical Co., Ltd.) Was added to the dissolved solution. Thereafter, dispersion treatment was performed for 1 hour in an atmosphere of 23 ± 3 ° C. in a sand mill apparatus using glass beads having a diameter of 1 mm. After dispersion treatment, 100 parts of ethyl acetate was added to prepare a coating solution for a charge generation layer. The charge generation layer coating solution is dip-coated on the undercoat layer to form a coating film, and the resulting coating film is dried at 90 ° C. for 10 minutes to form a charge generation layer having a thickness of 0.21 μm. Formed.

  Next, 30 parts of a compound represented by the following formula (B) (charge transporting substance), 60 parts of a compound represented by the following formula (C) (charge transporting substance), 10 parts of a compound represented by the following formula (D), polycarbonate 100 parts of resin (trade name: Iupilon Z400, manufactured by Mitsubishi Engineering Plastics Co., Ltd., bisphenol Z-type polycarbonate), a structural unit represented by the following formula (E) and a structural unit represented by the following formula (F) For charge transport layer by dissolving 0.02 part of polycarbonate (viscosity average molecular weight Mv: 20000) in a mixed solvent of 600 parts of mixed xylene (a mixture of o-xylene and m-xylene) and 200 parts of dimethoxymethane A coating solution was prepared. This charge transport layer coating solution was dip coated on the charge generation layer to form a coating film, and the resulting coating film was dried at 100 ° C. for 30 minutes to form a charge transport layer having a thickness of 21 μm.

(In the formulas (E) and (F), 0.95 and 0.05 indicate the molar ratio (copolymerization ratio) of the structural unit represented by the formula (E) and the structural unit represented by the formula (F). )
Next, as a charge transporting compound having a monovalent group represented by the above formula (1), 100 parts of exemplary compound (1-1) was dissolved in 100 parts of n-propyl alcohol. To this solution, 100 parts of 1,1,2,2,3,3,4-heptafluorocyclopentane (trade name: ZEOLORA H, manufactured by Nippon Zeon Co., Ltd.) was added to give a protective layer coating solution. Prepared.

  This coating solution for protective layer was dip coated on the charge transport layer to form a coating film, and the resulting coating film was dried at 50 ° C. for 5 minutes. After drying, the coating film was cured by irradiating the coating film with an electron beam while rotating the support for 6.4 seconds under the conditions of an acceleration voltage of 70 kV and an absorbed dose of 7000 Gy in a nitrogen atmosphere. Thereafter, heat treatment was performed for 25 seconds in a nitrogen atmosphere under conditions where the coating film reached 130 ° C. The oxygen concentration from the electron beam irradiation to the heat treatment for 25 seconds was 18 ppm. Next, in the atmosphere, a heat treatment was performed for 12 minutes under the condition that the coating film became 110 ° C., thereby forming a protective layer (surface layer) having a film thickness of 5 μm.

  Thus, a drum-shaped electrophotographic photosensitive member having an undercoat layer, a charge generation layer, a charge transport layer, and a protective layer in this order on the support was produced.

<Examples 2-36>
In Example 1, a coating solution for a protective layer was prepared by changing the exemplified compound (1-1) to the exemplified compound shown in Table 1 as the charge transporting compound having a monovalent group represented by the above formula (1). An electrophotographic photoreceptor was produced in the same manner as Example 1 except for the above.

<Example 37>
In Example 1, the coating liquid for protective layer was changed as follows. 80 parts of exemplary compound (1-37), 20 parts of trimethylolpropane trimethacrylate (product name: Miramer M301, manufactured by Toyo Chemicals Co., Ltd.), 0.005 part of hydroquinone monomethyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) Was dissolved in 100 parts of n-propanol. To this solution, 100 parts of 1,1,2,2,3,3,4-heptafluorocyclopentane (trade name: Zeolora H, manufactured by Nippon Zeon Co., Ltd.) was added to prepare a coating solution for a protective layer. did.

  This protective layer coating solution was dip coated on the charge transport layer to form a coating film, and the resulting coating film was heat treated at 50 ° C. for 5 minutes. Thereafter, an electron beam was irradiated for 3.2 seconds under conditions of an acceleration voltage of 70 kV and an absorbed dose of 50000 Gy in a nitrogen atmosphere. Then, it heat-processed for 30 second on conditions with a coating film becoming 130 degreeC in nitrogen atmosphere. The oxygen concentration from the electron beam irradiation to the heat treatment for 30 seconds was 19 ppm. Next, in the air, a heat treatment was performed for 12 minutes under the condition that the coating film became 110 ° C. to form a protective layer having a thickness of 5 μm. Except for these, an electrophotographic photosensitive member was produced in the same manner as in Example 1.

<Examples 38 to 42>
Example 37 was the same as Example 37 except that the coating liquid for protective layer was prepared by changing to the exemplified compound shown in Table 1 as the charge transporting compound having a monovalent group represented by the above formula (1). Thus, an electrophotographic photosensitive member was produced.

<Examples 43 to 62>
Example 1 was the same as Example 1 except that the coating liquid for protective layer was prepared by changing to the exemplified compounds shown in Table 1 as the charge transporting compound having a monovalent group represented by the above formula (1). Thus, an electrophotographic photosensitive member was produced.

<Example 63>
In Example 1, the coating liquid for protective layer was changed as follows. 99 parts of Exemplified Compound (1-1) and 1 part of 1-hydroxy-cyclohexyl-phenyl-ketone (trade name: Irgacure 184, manufactured by Ciba Specialty Chemicals) were dissolved in 100 parts of n-propanol. A protective layer coating solution was prepared by adding 100 parts of 1,1,2,2,3,3,4-heptafluorocyclopentane to this solution.

This coating solution for protective layer was dip coated on the charge transport layer to form a coating film, and the resulting coating film was heat-treated at 50 ° C. for 5 minutes. Then, using a metal halide lamp, the coating film was irradiated with ultraviolet rays for 20 seconds under the condition of irradiation intensity: 500 mW / cm ² , and the film thickness was 5 μm by heat treatment for 30 minutes under the condition that the coating film reached 130 ° C. A protective layer was formed. Except for these, an electrophotographic photosensitive member was produced in the same manner as in Example 1.

<Example 64>
Example 63 is the same as Example 63 except that the coating liquid for protective layer was prepared by changing to the exemplary compounds shown in Table 1 as the charge transporting compound having a monovalent group represented by the above formula (1). Thus, an electrophotographic photosensitive member was produced.

<Example 65>
In Example 1, a protective layer coating solution was prepared as follows. 80 parts of Exemplified Compound (1-45), 20 parts of trimethylolpropane trimethacrylate (Miramer M301) and 1 part of 1-hydroxy-cyclohexyl-phenyl-ketone (Irgacure 184) were dissolved in 100 parts of n-propanol. . A protective layer coating solution was prepared by adding 100 parts of 1,1,2,2,3,3,4-heptafluorocyclopentane (trade name: Zeolora H) to this solution. This coating solution for protective layer was dip coated on the charge transport layer to form a coating film, and the resulting coating film was heat-treated at 50 ° C. for 5 minutes. Then, using a metal halide lamp, the coating film was irradiated with ultraviolet rays for 20 seconds under the condition of irradiation intensity: 500 mW / cm ² , and the film thickness was 5 μm by heat treatment for 30 minutes under the condition that the coating film reached 130 ° C. A protective layer was formed. Except for these, an electrophotographic photosensitive member was produced in the same manner as in Example 1.

<Example 66>
Example 65 is the same as Example 65 except that the coating liquid for protective layer was prepared by changing to the exemplified compound shown in Table 1 as the charge transporting compound having a monovalent group represented by the above formula (1). Thus, an electrophotographic photosensitive member was produced.

<Comparative example>
Below, the comparative compound used in Comparative Examples 1-6 is shown.

<Comparative example 1>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1, except that the protective layer coating solution was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (F). did.

<Comparative example 2>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the coating compound for the protective layer was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (G). did.

<Comparative Example 3>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the coating compound for the protective layer was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (H). did.

<Comparative example 4>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1, except that the protective layer coating solution was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (I). did.

<Comparative Example 5>
In Example 37, an electrophotographic photosensitive member was produced in the same manner as in Example 37, except that the protective layer coating solution was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (I). did.

<Comparative Example 6>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the protective layer coating solution was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (J). did.

<Comparative Example 7>
In Example 1, an electrophotographic photosensitive member was produced in the same manner as in Example 1, except that the protective layer coating solution was prepared by changing the exemplified compound (1-1) to the compound represented by the above formula (M). did.

(Evaluation)
About the evaluation method of the electrophotographic photoreceptor of Examples 1-66 and Comparative Examples 1-6, it is as follows.

(Image evaluation at the initial stage of image formation)
A copying machine (trade name: GP-405, manufactured by Canon Inc.), which is an electrophotographic apparatus, was used as an evaluation apparatus. As a modification point, the charging roller of the process cartridge for the copying machine was changed to a corona charger (a corona charger for the copying machine GP-55 (trade name) manufactured by Canon Inc.), and from the outside of the copying machine. Modified to supply power to the corona charger. Further, the GP-405 drum cartridge was modified so that a corona charger could be mounted.

  A high voltage power supply control system (Model 615-3, manufactured by Trek) was used as a power source for supplying power for the corona charger from the outside of the copying machine. And it adjusted so that the electric current amount which flows through the corona wire of a corona charger might be 500 microamperes. Further, the constant current control scorotron grid applied voltage and the exposure apparatus so that the initial dark portion potential (Vd) of the electrophotographic photosensitive member is −700 [V] and the initial bright portion potential (Vl) is −200 [V]. The exposure light amount conditions were set.

  After the manufactured electrophotographic photosensitive member is mounted on a process cartridge and mounted on the evaluation apparatus, an image with an image printing ratio of 3% is printed on A4 vertical size paper in an environment of a temperature of 35 ° C. and a humidity of 85% RH. 1000 sheets were output. Every 1000 image outputs, the power supply to the evaluation apparatus was stopped, and it was suspended for 2 days. Power supply to the evaluation device was started again after a 2-day pause, and a character image (E character image) in which a halftone image and the letter E of the alphabet (font type: Times, font size 6 points) were repeated on A4 vertical size paper ) Was output. As the halftone image, the image of the 1-dot Keima pattern shown in FIG. 3 was used. The heater for the electrophotographic photosensitive member (drum heater (cassette heater)) was always turned off during the evaluation. Thereafter, the same evaluation was performed twice (total of 3000 sheets passed).

About the obtained image, the effect which suppresses an image flow (an image defect in which a white spot and an image density become thin) was evaluated according to the following evaluation ranks. The larger the rank number, the better. Ranks 6, 5, 4 and 3 were judged to be levels at which the effect of suppressing image blur of the present invention was obtained. On the other hand, ranks 1 and 2 were determined to be levels at which the image flow suppression effect of the present invention was not obtained. The evaluation results are shown in Table 2.
Rank 6: No image defect (image flow) is observed in both the halftone image and the E character image.
Rank 5: The density of the halftone image is light, but there is no image defect of the E character image.
Rank 4: The halftone image is partially blank, but there is no image defect in the E character image.
Rank 3: The halftone image is partially blank and the E character image density is light.
Rank 2: The halftone image is partially blank and the E character image density is partially blank.
Rank 1: The halftone image is mostly white and the E character image density is mostly white.

DESCRIPTION OF SYMBOLS 101 Support body 102 Charge generation layer 103 Charge transport layer 104 Protective layer 1 Electrophotographic photosensitive member 2 Axis 3 Charging means 4 Exposure light 5 Development means 6 Transfer means 7 Transfer material 8 Fixing means 9 Cleaning means 10 Pre-exposure light 11 Process cartridge 12 Guide means

Claims (14)

In an electrophotographic photoreceptor having a support and a photosensitive layer formed on the support,
An electrophotographic photosensitive member, wherein the surface layer of the electrophotographic photosensitive member contains a polymer of a charge transporting compound having a monovalent polymerizable functional group represented by the following formula (1).

(In Formula (1), R ¹ represents a fluorine atom or an alkyl group having a fluorine atom. R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group.) The electrophotographic photosensitive member according to claim 1, wherein the charge transporting compound is a charge transporting compound having a monovalent polymerizable functional group represented by the following formula (2).

^{(R 1, R 21} and ^{R 22} in formula (2) is the same as defined in the formula (1) ^{R 1, R 21} and ^{R 22} in.) The electrophotographic photosensitive member according to claim ^1, wherein R ¹ is a fluorine atom. The electrophotographic photosensitive member according to claim ^1, wherein R ¹ is a trifluoromethyl group. The electrophotographic photoreceptor according to claim 1, wherein R ²¹ and R ²² are each independently a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group. The surface layer is
A charge transporting compound having a monovalent polymerizable functional group represented by the formula (1);
The electrophotographic photosensitive member according to any one of claims 1 to 5, comprising a polymer of a composition with a charge transporting compound having an acryloyloxy group or a methacryloyloxy group. The surface layer is
A charge transporting compound having a monovalent polymerizable functional group represented by the formula (1);
The electrophotographic photosensitive member according to claim 1, comprising a polymer of a composition with a compound having a polymerizable functional group and not having a structure having a charge transporting ability. A charge transporting compound having a monovalent polymerizable functional group represented by the formula (1) is:
The electrophotographic photoreceptor according to claim 1, which is at least one selected from the group consisting of a compound represented by the following formula (3) and a compound represented by the following formula (4).

(In the formula ^(3), Ar 1, Ar ² and Ar ⁴ each independently, .Ar ³ showing a monovalent group, or a substituted or unsubstituted aryl group represented by the following formula (M1) is A divalent group represented by the following formula (M2) or a substituted or unsubstituted arylene group, provided that at least one of Ar ^{1 to} Ar ⁴ is a monovalent group represented by the following formula (M1) Or a divalent group represented by the following formula (M2), wherein r is 0 or 1, provided that Ar ¹ , Ar ² and Ar ⁴ are a monovalent group represented by the following formula (M1). Otherwise, r is 1 and Ar ³ is a divalent group represented by the following formula (M2).)

(In formula (4), Ar ⁵ , Ar ⁶ , Ar ⁹ and Ar ¹⁰ each independently represent a monovalent group represented by the following formula (M1) or a substituted or unsubstituted aryl group. ⁷ and Ar ⁸ each independently represent a divalent group represented by the following formula (M2) or a substituted or unsubstituted arylene group, provided that at least one of Ar ^{5 to} Ar ¹⁰ represents the following formula: A monovalent group represented by (M1) or a divalent group represented by the following formula (M2): P1 is a divalent group in which an oxygen atom, a cycloalkylidene group, and two phenylene groups are bonded via an oxygen atom. Or s and t are each independently 0 or 1. However, Ar ⁵ , Ar ⁶ , Ar ⁹ and Ar ¹⁰ are each a monovalent group represented by the following formula (M1) not a group, Ar ⁷ is If not a divalent group represented by the serial formula (M2), t is 1, Ar ⁸ is a divalent group represented by the following formula (M2).)

^{(R 1, R 21} in the formula (M1), and ^{R 22, R} 1 in the formula ^{(1), R 21,} and ^{R 22} as synonymous. Formula in (M1), ^{Ar 11} represents a substituted Or an unsubstituted arylene group, where m is 0 or an integer of 1 or more.

^{(R 1, R 21} in the formula (M2), and ^{R 22, R} 1 in the formula ^{(1), R 21,} and ^{R 22} as synonymous. Formula in (M2), ^{Ar 12} represents a substituted Or an unsubstituted trivalent aromatic hydrocarbon group, where n is 0 or an integer of 1 or more.) The charge transporting compound is a compound represented by the formula (3);
The electrophotographic photosensitive member according to claim 8, wherein at least two of Ar ^{1 to} Ar ⁴ are a monovalent group represented by the formula (M1) or a divalent group represented by the formula (M2). . The charge transporting compound is a compound represented by the formula (4);
The electrophotographic photosensitive member according to claim 8, wherein at least two of Ar ^{5 to} Ar ¹⁰ are a monovalent group represented by the formula (M1) or a divalent group represented by the formula (M2). . An electrophotographic photoreceptor production method for producing the electrophotographic photoreceptor according to any one of claims 1 to 10, wherein the production method comprises:
Forming a coating film of the surface layer coating solution containing the charge transporting compound; and
A method for producing an electrophotographic photoreceptor, comprising a step of forming a surface layer by polymerizing the charge transporting compound in the coating film.   The method for producing an electrophotographic photosensitive member according to claim 11, wherein the charge transporting compound is polymerized by irradiating the coating film with an electron beam.   An electrophotographic photosensitive member according to any one of claims 1 to 10, and at least one means selected from the group consisting of a charging means, a developing means, a transfer means, and a cleaning means, are integrally supported, and electrophotographic A process cartridge which is detachable from the apparatus main body. An electrophotographic apparatus comprising: the electrophotographic photosensitive member according to claim 1; and a charging unit, an exposing unit, a developing unit, and a transferring unit.

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