JP2019035845A - Electrophotographic photoreceptor, process cartridge and electrophotographic device - Google Patents

Abstract

To provide an electrophotographic photoreceptor with potential variation suppressed before and after continuous image output, and a process cartridge and an electrophotographic device having the electrophotographic photoreceptor.SOLUTION: An electrophotographic photoreceptor has a substrate, an undercoat layer, and a photosensitive layer arranged in this order. The undercoat layer has a compound having a structure selected from the group represented by formulas (A1) to (A11), and a structure (polysulfide structure) represented by -(CH-CH-O-CH-CH-S-S)-, wherein n is an integer of 2 to 50.SELECTED DRAWING: None

Description

  The present invention relates to an electrophotographic photosensitive member, a process cartridge having the electrophotographic photosensitive member, and an electrophotographic apparatus.

  As an electrophotographic photosensitive member mounted on a process cartridge or an electrophotographic apparatus, an electrophotographic photosensitive member containing an organic photoconductive substance (charge generating substance) is mainly used. In general, an electrophotographic photoreceptor has a support and a photosensitive layer formed on the support, and an undercoat layer is often formed between the support and the photosensitive layer.

In recent years, the demand for image quality is increasing. For example, the allowable range for color reproducibility has become much stricter.
The color reproducibility is greatly influenced by the stability of the potential of the electrophotographic photoreceptor. In particular, when the potential greatly fluctuates when outputting a large number of sheets, color reproducibility deteriorates and image quality deteriorates.
Not only full color output but also black and white output, the density of the halftone image changes, leading to a decrease in image quality.

As a technique for suppressing (reducing) such potential fluctuations when outputting a large number of sheets, a technique for containing an electron transport material in the undercoat layer is known.
For example, in Patent Document 1, Patent Document 2, and Patent Document 3, the undercoat layer includes an electron transport material such as a fluorenone compound derivative, an imide compound derivative, or an anthraquinone derivative. Technology is disclosed.

JP 2001-83726 A JP 2003-345044 A JP 2008-65173 A

  As a result of the study by the present inventors, it has been found that there is still room for improvement in the above-described conventional technology with respect to potential fluctuation (deterioration) before and after the continuous image output.

An object of the present invention is to provide an electrophotographic photosensitive member in which potential fluctuation before and after continuous image output is suppressed, a process cartridge having the electrophotographic photosensitive member, and an electrophotographic apparatus.
As a result of intensive studies, the present inventors have included a polymer of a compound having a specific structure in the undercoat layer of the electrophotographic photosensitive member, thereby suppressing the potential fluctuation before and after continuous image output at a high level. It has been found that it will be possible to achieve.

That is, the present invention is an electrophotographic photosensitive member having a support, an undercoat layer, and a photosensitive layer in this order, and the undercoat layer is represented by any of the following formulas (A1) to (A11). And a structure (polysulfide structure) represented by — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —SS) _n — (n is an integer of 2 to 50). An electrophotographic photosensitive member characterized by comprising:

In the above formulas (A1) to (A11), at least one of R ^{11 to} R ¹⁶ , one of R ^{21 to} R ³⁰ , one of R ^{31 to} R ³⁸ , and one of R ^{41 to} R ⁴⁸ . One of R ^{51 to} R ⁶⁰ , One of R ^{61 to} R ⁶⁶ , One of R ^{71 to} R ⁷⁸ , One of R ^{81 to} R ⁹⁰ , One of R ^{91 to} R ⁹⁸ One of R ^{101 to} R ¹¹⁰ and one of R ^{111 to} R ¹²⁰ are a single bond.

R ^{11 to} R ¹⁶ , R ^{21 to} R ³⁰ , R ^{31 to} R ³⁸ , R ^{41 to} R ⁴⁸ , R ^{51 to} R ⁶⁰ , R ^{61 to} R ⁶⁶ , R ^{71 to} R ⁷⁸ , R ^{81 to} R other than a single bond ⁹⁰ , R ^{91 to} R ⁹⁸ , R ^{101 to} R ¹¹⁰ , and R ^{111 to} R ¹²⁰ are each independently a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a cyano group, a dialkylamino group, a nitro group, a substituted or unsubstituted group. An alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. One of CH _{2 in} the main chain of the alkyl group may be replaced with O, S, NH or NR ¹²¹ (R ¹²¹ is an alkyl group).
The substituent of the substituted alkyl group or the substituted alkoxy group is an alkyl group, an aryl group, a halogen atom, or an alkoxycarbonyl group. The substituent of the substituted aryl group and the substituted heterocyclic group is a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, or an alkoxy group.

Z ²¹ , Z ³¹ , Z ⁴¹ and Z ⁵¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. When Z ²¹ is an oxygen atom, R ²⁹ and R ³⁰ do not exist, and when Z ²¹ is a nitrogen atom, R ³⁰ does not exist. When Z ³¹ is an oxygen atom, R ³⁷ and R ³⁸ do not exist, and when Z ³¹ is a nitrogen atom, R ³⁸ does not exist. If Z ⁴¹ is an oxygen atom ^{R 47} and ^{R 48} are ^absent, when ^{Z 41} is a nitrogen atom ^{R 48} is absent. When Z ⁵¹ is an oxygen atom, R ⁵⁹ and R ⁶⁰ do not exist, and when Z ⁵¹ is a nitrogen atom, R ⁶⁰ does not exist.

  In addition, 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 detachably attached to the electrophotographic apparatus main body. This is a process cartridge.

  The present invention also provides an electrophotographic apparatus comprising the above electrophotographic photosensitive member, a charging unit, an exposure unit, a developing unit, and a transfer unit.

  According to the present invention, it is possible to provide an electrophotographic photosensitive member in which potential fluctuations before and after continuous image output are suppressed, a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

1 is a diagram illustrating a schematic configuration of an electrophotographic apparatus having a process cartridge including the electrophotographic photosensitive member of the present invention.

Hereinafter, the present invention will be described in detail with reference to preferred embodiments.
[Electrophotographic photoreceptor]
The electrophotographic photoreceptor of the present invention has a support, an undercoat layer, and a photosensitive layer.
Examples of the method for producing the electrophotographic photosensitive member of the present invention include a method in which a coating solution for each layer described later is prepared, applied on a support in the order of desired layers, and dried. At this time, examples of the coating method of the coating liquid include dip coating, spray coating, inkjet coating, roll coating, die coating, blade coating, curtain coating, wire bar coating, and ring coating. Among these, dip coating is preferable from the viewpoints of efficiency and productivity.
Hereinafter, the support and each layer will be described.

<Support>
In the present invention, the electrophotographic photosensitive member has a support. The support is preferably a conductive support having conductivity. Moreover, examples of the shape of the support include a cylindrical shape, a belt shape, and a sheet shape. Among these, a cylindrical support is preferable. Further, the surface of the support may be subjected to electrochemical treatment such as anodic oxidation, blast treatment, cutting treatment or the like.
As the material for the support, metal, resin, glass and the like are preferable.
Examples of the metal include aluminum, iron, nickel, copper, gold, stainless steel, and alloys thereof. Among these, an aluminum support using aluminum is preferable.
In addition, the resin or glass may be imparted with conductivity by a treatment such as mixing or coating with a conductive material.

<Conductive layer>
In the present invention, a conductive layer may be provided on the support. By providing the conductive layer, it is possible to conceal scratches and irregularities on the surface of the support and to control light reflection on the surface of the support.
The conductive layer preferably contains conductive particles and a resin.

Examples of the material of the conductive particles include metal oxide, metal, carbon black and the like.
Examples of the metal oxide include zinc oxide, aluminum oxide, indium oxide, silicon oxide, zirconium oxide, tin oxide, titanium oxide, magnesium oxide, antimony oxide, and bismuth oxide. Examples of the metal include aluminum, nickel, iron, nichrome, copper, zinc, silver and the like.
Among these, it is preferable to use a metal oxide as the conductive particles, and it is particularly preferable to use titanium oxide, tin oxide, or zinc oxide.
When a metal oxide is used as the conductive particles, the surface of the metal oxide may be treated with a silane coupling agent or the like, or an element such as phosphorus or aluminum or an oxide thereof may be doped into the metal oxide.
Further, the conductive particles may have a laminated structure including core material particles and a coating layer that covers the particles. Examples of the core material particles include titanium oxide, barium sulfate, and zinc oxide. Examples of the coating layer include metal oxides such as tin oxide.
Moreover, when using a metal oxide as electroconductive particle, it is preferable that the volume average particle diameters are 1 nm or more and 500 nm or less, and it is more preferable that they are 3 nm or more and 400 nm or less.

Examples of the resin include polyester resin, polycarbonate resin, polyvinyl acetal resin, acrylic resin, silicone resin, epoxy resin, melamine resin, polyurethane resin, phenol resin, alkyd resin, and the like.
The conductive layer may further contain a masking agent such as silicone oil, resin particles, and titanium oxide.

The average film thickness of the conductive layer is preferably 1 μm or more and 50 μm or less, and particularly preferably 3 μm or more and 40 μm or less.
The conductive layer can be formed by preparing a coating liquid for a conductive layer containing each of the above materials and solvent, forming this coating film, and drying it. Examples of the solvent used for the coating solution include alcohol solvents, sulfoxide solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents. Examples of the dispersion method for dispersing the conductive particles in the coating liquid for the conductive layer include a method using a paint shaker, a sand mill, a ball mill, and a liquid collision type high-speed disperser.

<Underlayer>
In the present invention, an undercoat layer is provided on the support or the conductive layer.
The undercoat layer has at least one structure selected from structures represented by the following formulas (A1) to (A11), and — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —SS). and a compound represented by _n- (n is an integer of 2 to 50) (polysulfide structure).

(At least one of R ^{11 to} R ¹⁶ , one of R ^{21 to} R ³⁰ , one of R ^{31 to} R ³⁸ , one of R ^{41 to} R ⁴⁸ , and one of R ^{51 to} R ⁶⁰ . ^one, one of R 61 ^{to R 66,} one of R 71 ^{to R 78,} one of R 81 ^{to R 90,} one of R 91 ^{to R 98,} one of R 101 ^{to R 110} One of R ^{111 to} R ¹²⁰ is a single bond.
R ^{11 to} R ¹⁶ , R ^{21 to} R ³⁰ , R ^{31 to} R ³⁸ , R ^{41 to} R ⁴⁸ , R ^{51 to} R ⁶⁰ , R ^{61 to} R ⁶⁶ , R ^{71 to} R ⁷⁸ , R ^{81 to} R other than a single bond ⁹⁰ , R ^{91 to} R ⁹⁸ , R ^{101 to} R ¹¹⁰ , and R ^{111 to} R ¹²⁰ are each independently a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a cyano group, a dialkylamino group, a nitro group, a substituted or unsubstituted group. An alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. One of CH _{2 in} the main chain of the alkyl group may be replaced with O, S, NH or NR ¹²¹ (R ¹²¹ is an alkyl group).
The substituents of the substituted alkyl group and the substituted alkoxy group are an alkyl group, an aryl group, a halogen atom, and an alkoxycarbonyl group.
The substituent of the substituted aryl group and the substituted heterocyclic group is a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, or an alkoxy group.
Z ²¹ , Z ³¹ , Z ⁴¹ and Z ⁵¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. When Z ²¹ is an oxygen atom, R ²⁹ and R ³⁰ do not exist, and when Z ²¹ is a nitrogen atom, R ³⁰ does not exist. When Z ³¹ is an oxygen atom, R ³⁷ and R ³⁸ do not exist, and when Z ³¹ is a nitrogen atom, R ³⁸ does not exist. If Z ⁴¹ is an oxygen atom ^{R 47} and ^{R 48} are ^absent, when ^{Z 41} is a nitrogen atom ^{R 48} is absent. When Z ⁵¹ is an oxygen atom, R ⁵⁹ and R ⁶⁰ do not exist, and when Z ⁵¹ is a nitrogen atom, R ⁶⁰ does not exist. )

The ratio of the structure represented by — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —S—S) _n — (n is an integer of 2 to 50) contained in the undercoat layer is 1 mass. % To 10% by mass is preferable.

Undercoat layer, in addition to the polysulfide structure preferably further has a structure represented by _{-CO-NH-C 6 H 12} -NH-CO-.

In addition to the polysulfide structure, the undercoat layer may further have a structure represented by —CO—NH—C ₆ H ₁₂ —N (CO—NH—C ₆ H ₁₂ —NH—CO—) _2. preferable.

Furthermore, the undercoat layer includes at least one compound selected from the following formulas (A1) to (A11), a compound having an isocyanate group, a blocked isocyanate group, or an N methylol group, and HS— (CH ₂ —CH ₂ of _{-O-CH 2 -CH 2 -S-} S) n -C 2 H 4 -O-C 2 H 4 -SH (n is a composition containing a compound represented by integers) from 2 to 50 You may have a polymer.

  The polysulfide structure may have a cross-linking agent having a functional group crosslinkable with a functional group of the electron transport material, or a resin having a functional group crosslinkable with the functional group of the cross-linking agent. May be.

The mechanism by which the electron transport ability is improved and the potential fluctuation is improved by using the compound having the polysulfide structure is not clear, but the inventor thinks as follows.
Compared to oxygen, carbon, etc., this structure has a structure in which large sulfur atoms are connected. Therefore, the film-forming property can be maintained while having flexibility, and since there are few film defects, the electron transport is inhibited. It is expected that it will not occur easily.

Hereinafter, the electron transport material, the crosslinking agent, and the resin will be described.
(1) Electron Transport Material In the present invention, the content of the electron transport material in the undercoat layer needs to be 30% by mass or more with respect to the total mass of the composition. Furthermore, 70 mass% or less is preferable. By setting it to 70 mass% or less, generation | occurrence | production of elution can be prevented and an electric potential fluctuation inhibitory effect can fully be acquired.

The electron transport material is at least one selected from compounds represented by the following general formulas (A1) to (A11).

In the general formulas (A1) to (A11), at least one of R ^{11 to} R ¹⁶ , at least one of R ^{21 to} R ³⁰ , at least one of R ^{31 to} R ³⁸ , and at least one of R ^{41 to} R ⁴⁸ , At least one of R ^{51 to} R ⁶⁰ , at least one of R ^{61 to} R ⁶⁶ , at least one of R ^{71 to} R ⁷⁸ , at least one of R ^{81 to} R ⁹⁰ , at least one of R ^{91 to} R ⁹⁸ , At least one of R ^{101 to} R ¹¹⁰ and at least one of R ^{111 to} R ¹²⁰ is a monovalent group represented by the following general formula (A). Except for the monovalent group represented by formula (A), each independently represents a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkoxycarbonyl group, a dialkylamino group, an alkyl group, an alkoxy group, an aryl group, or a heterocyclic ring. Or one of CH _{2 in} the main chain of the alkyl group is replaced with O, S, NH or NR ¹²¹ (R ¹²¹ is an alkyl group). The alkyl group, alkoxy group, aryl group, and heterocyclic group may further have a substituent. Examples of the substituent for the alkyl group and alkoxy group include an alkyl group, an aryl group, a halogen atom, and an alkoxycarbonyl group. Examples of the substituent for the aryl group and heterocyclic group include a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, and an alkoxy group.
Z ²¹ , Z ³¹ , Z ⁴¹ and Z ⁵¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. When Z ²¹ is an oxygen atom, R ²⁹ and R ³⁰ do not exist, and when Z ²¹ is a nitrogen atom, R ³⁰ does not exist. When Z ³¹ is an oxygen atom, R ³⁷ and R ³⁸ do not exist, and when Z ³¹ is a nitrogen atom, R ³⁸ does not exist. If Z ⁴¹ is an oxygen atom ^{R 47} and ^{R 48} are ^absent, when ^{Z 41} is a nitrogen atom ^{R 48} is absent. When Z ⁵¹ is an oxygen atom, R ⁵⁹ and R ⁶⁰ do not exist, and when Z ⁵¹ is a nitrogen atom, R ⁶⁰ does not exist.

In general formula (A), α is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms in the main chain, and the substituted alkylene group is an alkyl group having 1 to 6 carbon atoms, a benzyl group, an alkoxy group. It has at least one group selected from the group consisting of a carbonyl group or a phenyl group. Furthermore, the substituted alkylene group may have a group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent. One of CH _{2 in} the main chain of the alkylene group may be replaced with O, S, NR ¹²² (wherein R ¹²² represents a hydrogen atom or an alkyl group).
β is a substituted or unsubstituted phenylene group, and the substituted phenylene group is any one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a nitro group, a halogen group, or an alkoxy group. At least. Furthermore, the substituted phenylene group may have a group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent.
γ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms in the main chain, or an alkyl group having 1 to 6 carbon atoms in the main chain substituted with an alkyl group having 1 to 6 carbon atoms. These groups may have a group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent. One of CH _{2 in} the main chain of the alkyl group may be replaced with O, S, or NR ¹²³ (wherein R ¹²³ represents a hydrogen atom or an alkyl group).

  At least one of α, β, and γ is a group having a substituent, and the substituent is selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group. l and m are each independently 0 or 1, and the sum of l and m is 0 or more and 2 or less.

  Among these, a compound represented by the general formula (A1) or a compound represented by the general formula (A8) is particularly preferable. Since these compounds have a structure that is easy to stack, it is believed that the effect of improving adhesion can be obtained more effectively. These compounds can be synthesized by the method described in JP-A-2015-143828. Specific examples of the compounds represented by the general formulas (A1) and (A8) are shown in Tables 1 and 2 below.

(2) Crosslinking agent Any known material can be used as the crosslinking agent. Specific examples include compounds described in Shinzo Yamashita and Tosuke Kaneko “Crosslinking Agent Handbook” (published by Taiseisha, published in 1981). In the present invention, the crosslinking agent preferably has a polymerizable functional group.

  In the present invention, the crosslinking agent is preferably an isocyanate compound, a blocked isocyanate compound, a methylol compound, or an alkylated methylol compound.

  Examples of commercially available crosslinking agents include Duranate MFK-60B, SBA-70B (above, manufactured by Asahi Kasei), Desmodur BL3175, BL3475 (above, manufactured by Sumika Bayer Urethane), Super Melami No. 90 (manufactured by NOF Corporation), Super Becamine (R) TD-139-60, L-105-60, L127-60, L110-60, J-820-60, G-821-60, L-148-55 , 13-535, L-145-60, TD-126 (manufactured by DIC), Uban 2020 (manufactured by Mitsui Chemicals), Smitex Resin M-3 (manufactured by Sumitomo Chemical Co., Ltd.), Nikaluck MW-30, MW-390 , MX-750LM, BL-60, BX-4000, MX-280, MX-270, MX-290 (manufactured by Nippon Carbide).

(3) Resin A hydroxy group, a thiol group, an amino group, or a carboxyl group and — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —S—S) _n — (n is an integer of 2 to 50). As the resin having the above structure, any resin having these structures may be used. Among these, a compound represented by the following formula (B1) is preferable.
HS— (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —S—S) _n —C ₂ H ₄ —O—C ₂ H ₄ —SH (B1) (n is an integer of 2 to 50)

(Other resins)
The undercoat layer may contain a resin having no polysulfide structure. In that case, a thermoplastic resin is preferable, polyolefin resin, polyester resin, polycarbonate resin, polyvinyl acetal resin, acrylic resin, polyurethane resin, polyvinyl phenol resin, polyvinyl alcohol resin, polyethylene oxide resin, polypropylene oxide resin, polyamide resin, polyamic acid resin. , Polyimide resin, polyamideimide resin, cellulose resin and the like.

Furthermore, the resin preferably has a polymerizable functional group. Examples of the polymerizable functional group include a hydroxyl group, a thiol group, an amino group, a carboxyl group, and a methoxy group. That is, the resin preferably has a structural unit represented by the following general formula (C).
In the general formula (C), R ¹ represents a hydrogen atom or an alkyl group. Y ¹ represents a single bond, an alkylene group or a phenylene group. W ¹ represents a hydroxy group, a thiol group, an amino group, or a carboxyl group.

What is marketed as a thermoplastic resin having a polymerizable functional group is, for example,
Polyether polyol resins such as AQD-457, AQD-473 (manufactured by Nippon Polyurethane Industry), GP-400, GP-700 (manufactured by Sanyo Chemical Industries, Sannix);
Phthalkid W2343 (manufactured by Hitachi Chemical Co., Ltd.), Watersol S-118, CD-520, Beckolite M-6402-50, M-6201-40IM (manufactured by DIC), Hallidip WH-1188 (manufactured by Harima Chemicals), Polyester polyol resins such as ES3604 and ES6538 (manufactured by Nippon Iupika);
Polyacryl polyol resins such as Bernock WE-300 and WE-304 (manufactured by DIC);
Polyvinyl alcohol resins such as Kuraray Poval PVA-203 (manufactured by Kuraray);
Polyvinyl acetal resins such as BX-1, BM-1, KS-5 (manufactured by Sekisui Chemical Co., Ltd.);
Polyamide resin such as Toresin FS-350 (manufactured by Nagase ChemteX);
Carboxyl group-containing resins such as Aquaric (manufactured by Nippon Shokubai) and Finelex SG2000 (manufactured by Lead City);
Polyamine resins such as racamide (made by DIC);
Examples include polythiol resins such as QE-340M (Toray). Among these, a polyvinyl acetal resin having a polymerizable functional group, a polyester polyol resin having a polymerizable functional group, and the like are more preferable from the viewpoints of polymerizability and uniformity of the undercoat layer.

The undercoat layer may further contain an additive.
The average thickness of the undercoat layer is preferably from 0.1 μm to 50 μm, more preferably from 0.2 μm to 40 μm, and particularly preferably from 0.3 μm to 30 μm.

  The undercoat layer is formed by preparing a coating solution for the undercoat layer containing the above-mentioned materials and solvent, and forming this coating film on a support or a conductive layer, followed by drying and / or curing. Can do. Examples of the solvent used for the coating solution include alcohol solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents.

<Photosensitive layer>
The photosensitive layer of the electrophotographic photoreceptor is mainly classified into (1) a multilayer type photosensitive layer and (2) a single layer type photosensitive layer. (1) The laminated photosensitive layer has a charge generation layer containing a charge generation material and a charge transport layer containing a charge transport material. (2) The single-layer type photosensitive layer has a photosensitive layer containing both a charge generation material and a charge transport material.

(1) Laminated Photosensitive Layer The laminated photosensitive layer has a charge generation layer and a charge transport layer.

(1-1) Charge Generation Layer The charge generation layer preferably contains a charge generation material and a resin.

Examples of the charge generation material include azo pigments, perylene pigments, polycyclic quinone pigments, indigo pigments, and phthalocyanine pigments. Among these, azo pigments and phthalocyanine pigments are preferable. Among the phthalocyanine pigments, oxytitanium phthalocyanine pigments, chlorogallium phthalocyanine pigments, and hydroxygallium phthalocyanine pigments are preferable.
The content of the charge generation material in the charge generation layer is preferably 40% by mass to 85% by mass and more preferably 60% by mass to 80% by mass with respect to the total mass of the charge generation layer. preferable.

  The resin includes polyester resin, polycarbonate resin, polyvinyl acetal resin, polyvinyl butyral resin, acrylic resin, silicone resin, epoxy resin, melamine resin, polyurethane resin, phenol resin, polyvinyl alcohol resin, cellulose resin, polystyrene resin, polyvinyl acetate resin. And polyvinyl chloride resin. Among these, polyvinyl butyral resin is more preferable.

  The charge generation layer may further contain additives such as an antioxidant and an ultraviolet absorber. Specific examples include hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, and benzophenone compounds.

  The average film thickness of the charge generation layer is preferably from 0.1 μm to 1 μm, and more preferably from 0.15 μm to 0.4 μm.

  The charge generation layer can be formed by preparing a coating solution for a charge generation layer containing the above-described materials and solvent, forming this coating film, and drying it. Examples of the solvent used for the coating solution include alcohol solvents, sulfoxide solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents.

(1-2) Charge Transport Layer The charge transport layer preferably contains a charge transport material and a resin.

  Examples of the charge transport material include polycyclic aromatic compounds, heterocyclic compounds, hydrazone compounds, styryl compounds, enamine compounds, benzidine compounds, triarylamine compounds, and resins having groups derived from these materials. It is done. Among these, a triarylamine compound and a benzidine compound are preferable.

  The content of the charge transport material in the charge transport layer is preferably 25% by mass to 70% by mass and more preferably 30% by mass to 55% by mass with respect to the total mass of the charge transport layer. preferable.

  Examples of the resin include polyester resin, polycarbonate resin, acrylic resin, and polystyrene resin. Among these, polycarbonate resin and polyester resin are preferable. As the polyester resin, polyarylate resin is particularly preferable.

  The content ratio (mass ratio) between the charge transport material and the resin is preferably 4:10 to 20:10, and more preferably 5:10 to 12:10.

  Further, the charge transport layer may contain additives such as an antioxidant, an ultraviolet absorber, a plasticizer, a leveling agent, a slipperiness imparting agent, and an abrasion resistance improving agent. Specifically, hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, benzophenone compounds, siloxane-modified resins, silicone oil, fluorine resin particles, polystyrene resin particles, polyethylene resin particles, silica particles, alumina particles, boron nitride particles Etc.

  The average film thickness of the charge transport layer is preferably 5 μm or more and 50 μm or less, more preferably 8 μm or more and 40 μm or less, and particularly preferably 10 μm or more and 30 μm or less.

  The charge transport layer can be formed by preparing a coating liquid for a charge transport layer containing the above-mentioned materials and solvent, forming this coating film on the charge generation layer, and drying it. Examples of the solvent used for the coating solution include alcohol solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents. Among these solvents, ether solvents or aromatic hydrocarbon solvents are preferable.

(2) Single-layer type photosensitive layer A single-layer type photosensitive layer is formed by preparing a coating solution for a photosensitive layer containing a charge generating substance, a charge transporting substance, a resin and a solvent, forming this coating film, and drying it. can do. Examples of the charge generating substance, the charge transporting substance, and the resin are the same as those exemplified in the above-mentioned “(1) Multilayer type photosensitive layer”.

<Protective layer>
In the present invention, a protective layer may be provided on the photosensitive layer. By providing the protective layer, durability can be improved.
The protective layer preferably contains conductive particles and / or a charge transport material and a resin.
Examples of the conductive particles include metal oxide particles such as titanium oxide, zinc oxide, tin oxide, and indium oxide.
Examples of the charge transport material include polycyclic aromatic compounds, heterocyclic compounds, hydrazone compounds, styryl compounds, enamine compounds, benzidine compounds, triarylamine compounds, and resins having groups derived from these materials. Among these, a triarylamine compound and a benzidine compound are preferable.
Examples of the resin include polyester resin, acrylic resin, phenoxy resin, polycarbonate resin, polystyrene resin, phenol resin, melamine resin, and epoxy resin. Among these, polycarbonate resin, polyester resin, and acrylic resin are preferable.

  Further, the protective layer may be formed as a cured film by polymerizing a composition containing a monomer having a polymerizable functional group. Examples of the reaction at that time include a thermal polymerization reaction, a photopolymerization reaction, and a radiation polymerization reaction. Examples of the polymerizable functional group possessed by the monomer having a polymerizable functional group include an acryl group and a methacryl group. As the monomer having a polymerizable functional group, a material having a charge transporting ability may be used.

  The protective layer may contain additives such as an antioxidant, an ultraviolet absorber, a plasticizer, a leveling agent, a slipperiness imparting agent, and an abrasion resistance improver. Specifically, hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, benzophenone compounds, siloxane-modified resins, silicone oil, fluorine resin particles, polystyrene resin particles, polyethylene resin particles, silica particles, alumina particles, boron nitride particles Etc.

The average film thickness of the protective layer is preferably 0.5 μm or more and 10 μm or less, and preferably 1 μm or more and 7 μm or less.
The protective layer can be formed by preparing a protective layer coating solution containing the above-mentioned materials and solvent, forming this coating film on the photosensitive layer, and drying and / or curing it. Examples of the solvent used for the coating solution include alcohol solvents, ketone solvents, ether solvents, sulfoxide solvents, ester solvents, and aromatic hydrocarbon solvents.

[Process cartridge, electrophotographic equipment]
The process cartridge of the present invention integrally supports the electrophotographic photosensitive member described so far and at least one means selected from the group consisting of a charging means, a developing means, a transfer means, and a cleaning means. It is detachable from the main body.
The electrophotographic apparatus of the present invention includes the electrophotographic photosensitive member, the charging unit, the exposure unit, the developing unit, and the transfer unit described so far.

FIG. 1 shows an example of a schematic configuration of an electrophotographic apparatus having a process cartridge provided with an electrophotographic photosensitive member.
Reference numeral 1 denotes a cylindrical electrophotographic photosensitive member, which is driven to rotate at a predetermined peripheral speed in the direction of an arrow about an axis 2. The surface of the electrophotographic photoreceptor 1 is charged to a predetermined positive or negative potential by the charging unit 3. In the drawing, a roller charging method using a roller-type charging member is shown, but a charging method such as a corona charging method, a proximity charging method, and an injection charging method may be adopted. The surface of the charged electrophotographic photosensitive member 1 is irradiated with exposure light 4 from an exposure means (not shown), and an electrostatic latent image corresponding to target image information is formed. The electrostatic latent image formed on the surface of the electrophotographic photosensitive member 1 is developed with toner accommodated in the developing means 5, and a toner image is formed on the surface of the electrophotographic photosensitive member 1. The toner image formed on the surface of the electrophotographic photoreceptor 1 is transferred to the transfer material 7 by the transfer means 6. The transfer material 7 onto which the toner image has been transferred is conveyed to the fixing means 8, undergoes a toner image fixing process, and is printed out of the electrophotographic apparatus. The electrophotographic apparatus may have a cleaning unit 9 for removing deposits such as toner remaining on the surface of the electrophotographic photosensitive member 1 after transfer. Further, a so-called cleaner-less system may be used in which the above deposits are removed by a developing unit or the like without providing a cleaning unit. The electrophotographic apparatus may have a static elimination mechanism that neutralizes the surface of the electrophotographic photosensitive member 1 with pre-exposure light 10 from pre-exposure means (not shown). Further, in order to attach / detach the process cartridge 11 of the present invention to / from the electrophotographic apparatus main body, a guide means 12 such as a rail may be provided.
The electrophotographic photosensitive member of the present invention can be used in laser beam printers, LED printers, copiers, facsimiles, and complex machines of these.

  Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The present invention is not limited in any way by the following examples as long as the gist thereof is not exceeded. In the description of the following examples, “part” is based on mass unless otherwise specified.

  As typical examples of the electron transporting material contained in the undercoat layer, synthesis examples of the compounds represented by formula (A109) and formula (A804) are shown.

(Synthesis Example 1)
Naphthalene-1,4,5,8-tetracarboxylic dianhydride (26.8 g, 100 mmol) and dimethylacetamide (250 ml) were placed in a 500 ml three-necked flask at room temperature under a nitrogen stream. After heating to 120 ° C., a mixture of 11.6 g (100 mmol) of 4-heptylamine, 9.2 g (100 mmol) of 2-amino-1,3-propanediol and 50 ml of dimethylacetamide was added dropwise thereto with stirring. After completion of dropping, the mixture was stirred with heating at 120 ° C. for 3 hours. After completion of the reaction, the container was cooled and concentrated under reduced pressure. Ethyl acetate was added to the residue, followed by filtration, and the filtrate was purified by silica gel column chromatography. Furthermore, the recovered product was recrystallized from ethyl acetate / hexane to obtain 11.3 g of an imide compound represented by the formula (A109) shown in Table 1.
When this compound was measured by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF MS), a peak top value 438 was obtained.

(Synthesis Example 2)
In a 300 ml three-necked flask at room temperature and under a nitrogen stream, 39.2 g (100 mmol) of 3,4,9,10-perylenetetracarboxylic dianhydride and 150 ml of dimethylacetamide were placed. To this, a mixture of 17.8 g (200 mmol) of amino-1-butanol, 23.4 g (200 mmol) of L-leucinol and 50 ml of dimethylacetamide was added dropwise with stirring. After completion of dropping, the mixture was heated to reflux for 6 hours. After completion of the reaction, the container was cooled and concentrated under reduced pressure. Chloroform was added to the residue, followed by filtration, and the filtrate was purified by silica gel column chromatography. Furthermore, the recovered product was recrystallized from ethyl acetate / hexane to obtain 16.0 g of an imide compound represented by the formula (A804) shown in Table 2.
When this compound was measured by MALDI-TOF MS, a peak top value of 590 was obtained.

Next, preparation and evaluation of an electrophotographic photoreceptor will be described.
Example 1
An aluminum cylinder (JIS-A3003, aluminum alloy) having a length of 260.5 mm and a diameter of 30 mm was used as a support (conductive support).

Next, 50 parts of titanium oxide particles coated with oxygen-deficient tin oxide (powder resistivity: 120 Ω · cm, tin oxide coverage: 40%), phenol resin (Pryofen J-325, DIC Corporation) ), Resin solid content: 60%) 40 parts and 55 parts of methoxypropanol were placed in a sand mill using glass beads having a diameter of 1 mm. Then, the coating liquid for conductive layers was prepared by carrying out the dispersion process for 3 hours.
The average particle size of the titanium oxide particles coated with oxygen-deficient tin oxide in the coating liquid for the conductive layer is measured using a particle size distribution meter (trade name: CAPA700, manufactured by Horiba, Ltd.), tetrahydrofuran as a dispersion medium, and the number of rotations. Measurements were made by centrifugal sedimentation at 5000 rpm. As a result, the average particle size was 0.30 μm.
The conductive layer coating solution was dip-coated on a support, and the resulting coating film was dried at 160 ° C. for 30 minutes to form a conductive layer having a thickness of 30 μm.

Next, 47.5 parts of the compound (A109), 7 parts of the resin represented by the above formula (B1), 45.5 parts of the crosslinking agent represented by the following formula (I1), and 0.001 part of dioctyltin laurate were added to methoxypropanol 60. Dissolved in a mixed solvent of 1 part and 60 parts of tetrahydrofuran. Thereby, the coating liquid for undercoat layers was prepared. The ratio of the polysulfide structure site in the cured film is 5.8%, and the ratio to A109 is 12.3%. In addition, the mass part of a crosslinking agent is the value which remove | divided the mass of the block group.
The undercoat layer coating solution is dip-coated on the conductive layer, and the resulting coating film is heated at 160 ° C. for 30 minutes to evaporate the solvent and harden it, thereby reducing the film thickness to 0.85 μm. A layer was formed.

Next, Bragg angles (2θ ± 0.2 °) in CuKα characteristic X-ray diffraction of 7.5 °, 9.9 °, 12.5 °, 16.3 °, 18.6 °, 25.1 ° and A crystalline hydroxygallium phthalocyanine crystal (charge generation material) having a peak at 28.3 ° was prepared. 10 parts of this hydroxygallium phthalocyanine crystal, 5 parts of polyvinyl butyral (trade name: ESREC BX-1, manufactured by Sekisui Chemical Co., Ltd.) and 250 parts of cyclohexanone are placed in a sand mill using glass beads having a diameter of 1 mm and dispersed for 2 hours. Processed. Next, 250 parts of ethyl acetate was added thereto to prepare a charge generation layer coating solution.
This 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 95 ° C. for 10 minutes, whereby a charge generation layer having a thickness of 0.2 μm is formed. Formed.

Next, 6 parts of an amine compound (charge transport material) represented by the following formula (1), 2 parts of an amine compound (charge transport material) represented by the following formula (2), and the following formulas (3) and (4) By dissolving 10 parts of a polyester resin having a structural unit of 1 to 1 and a weight average molecular weight (Mw) of 100,000 in a mixed solvent of 40 parts of dimethoxymethane and 60 parts of chlorobenzene. Then, a coating liquid for charge transport layer was prepared.
The charge transport layer coating solution was dip-coated on the charge generation layer, and the resulting coating film was dried at 120 ° C. for 40 minutes to form a charge transport layer having a thickness of 22 μm.

Thus, an electrophotographic photosensitive member having a conductive layer, an undercoat layer, a charge generation layer and a charge transport layer on a support was produced.
Remodeling machine (primary charging: roller contact DC charging, process) of laser beam printer (trade name: LBP-2510) manufactured by Canon Co., Ltd. in an environment of 15 ° C. and 10% RH. (Speed 180 mm / sec, laser exposure). Then, evaluation of the surface potential and output image after initial and after output of 20,000 images were performed. Details are as follows.

(Surface potential evaluation)
The cyan process cartridge for the laser beam printer was modified and a potential probe (model 6000B-8, manufactured by Trek Japan Co., Ltd.) was mounted at the development position. Next, the initial surface potential was measured using a surface potentiometer (model 344: manufactured by Trek Japan Co., Ltd.) for the potential at the center of the electrophotographic photosensitive member. Further, the amount of light for image exposure was set so that the dark portion potential (Vd) was −500 V and the light portion potential (Vl) was −120 V.
Subsequently, the produced electrophotographic photosensitive member was attached to the cyan process cartridge of the laser beam printer, and the process cartridge was attached to the cyan process cartridge station, and 20,000 images were output. .
After the completion of image output, the surface potential of the central portion of the electrophotographic photosensitive member was measured again using a potential probe and an electrometer.

(Examples 2 to 10)
The types and amounts (parts by mass) of the electron transport material, the crosslinking agent, and the resin were changed so that the ratio of the polysulfide structure as shown in Table 3 was obtained. Other than that, a photoconductor was prepared in the same manner as in Example 1, and the evaluation of the surface potential and the output image after initial and after output of 20,000 sheets of images were similarly performed. The results are shown in the table.

The structures of A5, A7, A10, I2, I3, I4, and I5 are as follows.

(Comparative Example 1)
A photoconductor was prepared in the same manner as in Example 1 except that B2 was used as the resin, and was similarly evaluated. The results are shown in Table 3.

(Comparative Example 2)
A photoconductor was prepared in the same manner as in Example 1 except that the following formula B3 was used as the resin, and evaluation was performed in the same manner. The results are shown in Table 3.
_{HO- (CH 2 -CH 2 -O-)} n-H (B3)
(N = 22)

(Comparative Example 3)
A photoconductor was prepared in the same manner as in Example 7 except that B3 (n = 22) was used as the resin, and evaluated in the same manner. The results are shown in Table 3.

(Comparative Example 4)
A photoconductor was prepared in the same manner as in Example 8 except that B2 was used as the resin, and evaluated in the same manner. The results are shown in Table 3.

(Comparative Example 5)
A photoconductor was prepared in the same manner as in Example 10 except that B3 (n = 200) was used as the resin, and evaluation was performed in the same manner. The results are shown in Table 3.

DESCRIPTION OF SYMBOLS 1 Electrophotographic photoreceptor 2 Axis 3 Charging means 4 Exposure light 5 Developing means 6 Transfer means 7 Transfer material 8 Fixing means 9 Cleaning means 10 Pre-exposure light 11 Process cartridge 12 Guide means

Claims (7)

An electrophotographic photosensitive member having a support, an undercoat layer, and a photosensitive layer in this order,
The undercoat layer is
At least one structure selected from structures represented by formulas (A1) to (A11);
A structure represented by — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —S—S) _n — (n is an integer of 2 to 50);
An electrophotographic photosensitive member comprising a compound having:
(At least one of R ^{11 to} R ¹⁶ , one of R ^{21 to} R ³⁰ , one of R ^{31 to} R ³⁸ , one of R ^{41 to} R ⁴⁸ , and one of R ^{51 to} R ⁶⁰ . ^one, one of R 61 ^{to R 66,} one of R 71 ^{to R 78,} one of R 81 ^{to R 90,} one of R 91 ^{to R 98,} one of R 101 ^{to R 110} One of R ^{111 to} R ¹²⁰ is a single bond.
R ^{11 to} R ¹⁶ , R ^{21 to} R ³⁰ , R ^{31 to} R ³⁸ , R ^{41 to} R ⁴⁸ , R ^{51 to} R ⁶⁰ , R ^{61 to} R ⁶⁶ , R ^{71 to} R ⁷⁸ , R ^{81 to} R other than a single bond ⁹⁰ , R ^{91 to} R ⁹⁸ , R ^{101 to} R ¹¹⁰ , and R ^{111 to} R ¹²⁰ are each independently a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a cyano group, a dialkylamino group, a nitro group, a substituted or unsubstituted group. An alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group is shown. One of CH _{2 in} the main chain of the alkyl group may be replaced with O, S, NH or NR ¹²¹ (R ¹²¹ is an alkyl group).
The substituent of the substituted alkyl group or the substituted alkoxy group is an alkyl group, an aryl group, a halogen atom, or an alkoxycarbonyl group. The substituent of the substituted aryl group and the substituent of the substituted heterocyclic group are a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, or an alkoxy group.
Z ²¹ , Z ³¹ , Z ⁴¹ and Z ⁵¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. When Z ²¹ is an oxygen atom, R ²⁹ and R ³⁰ do not exist, and when Z ²¹ is a nitrogen atom, R ³⁰ does not exist. When Z ³¹ is an oxygen atom, R ³⁷ and R ³⁸ do not exist, and when Z ³¹ is a nitrogen atom, R ³⁸ does not exist. If Z ⁴¹ is an oxygen atom ^{R 47} and ^{R 48} are ^absent, when ^{Z 41} is a nitrogen atom ^{R 48} is absent. When Z ⁵¹ is an oxygen atom, R ⁵⁹ and R ⁶⁰ do not exist, and when Z ⁵¹ is a nitrogen atom, R ⁶⁰ does not exist. ) The ratio of the structure represented by — (CH ₂ —CH ₂ —O—CH ₂ —CH ₂ —S—S) _n — (n is an integer of 2 to 50) contained in the undercoat layer is 1 The electrophotographic photosensitive member according to claim 1, wherein the electrophotographic photosensitive member is in the range of 10% by mass to 10% by mass. The electrophotographic photosensitive member according to claim 1, wherein the undercoat layer further has a structure represented by —CO—NH—C ₆ H ₁₂ —NH—CO—. The electrophotographic image according to claim 1, wherein the undercoat layer further has a structure represented by —CO—NH—C ₆ H ₁₂ —N (CO—NH—C ₆ H ₁₂ —NH—CO—) _2. Photoconductor. An electrophotographic photosensitive member having a support, an undercoat layer, and a photosensitive layer in this order,
The undercoat layer is
At least one compound selected from (A1) to (A11);
A compound having an isocyanate group or a blocked isocyanate group or an N methylol group;
_{HS- (CH 2 -CH 2 -O-} CH 2 -CH 2 -S-S) n -C 2 H 4 -O-C 2 H 4 -SH (n is an integer of 2 to 50) a compound represented by When,
An electrophotographic photosensitive member comprising a polymer of a composition comprising
(In the formulas (A1) to (A11), at least one of R ^{11 to} R ¹⁶ , at least one of R ^{21 to} R ³⁰ , at least one of R ^{31 to} R ³⁸ , and at least one of R ^{41 to} R ⁴⁸ , At least one of R ^{51 to} R ⁶⁰ , at least one of R ^{61 to} R ⁶⁶ , at least one of R ^{71 to} R ⁷⁸ , at least one of R ^{81 to} R ⁹⁰ , at least one of R ^{91 to} R ⁹⁸ , At least one of R ^{101 to} R ¹¹⁰ and at least one of R ^{111 to} R ¹²⁰ is a monovalent group represented by the following formula (A) other than the monovalent group represented by the formula (A). ^{R 11 ~R 16, R 21 ~R} 30, R 31 ~R 38, R 41 ~R 48, R 51 ~R 60, R 61 ~R 66, R 71 ~R 78, R 81 ~R 90, R 91 to R ^{98 is, R} 101 to R ^10, R 111 ^{to R 120} each independently represents a monovalent group represented by the formula (A), a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkoxycarbonyl group, a dialkylamino group, a substituted or unsubstituted An alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, wherein one of CH _{2 in} the main chain of the alkyl group is O, S, NH, or NR ¹²¹ (R ¹²¹ is an alkyl group) may be substituted.
The substituent of the substituted alkyl group or the substituted alkoxy group is an alkyl group, an aryl group, a halogen atom, or an alkoxycarbonyl group. The substituent of the substituted aryl group and the substituent of the substituted heterocyclic group are a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, or an alkoxy group. Z ²¹ , Z ³¹ , Z ⁴¹ and Z ⁵¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. When Z ²¹ is an oxygen atom, R ²⁹ and R ³⁰ do not exist, and when Z ²¹ is a nitrogen atom, R ³⁰ does not exist. When Z ³¹ is an oxygen atom, R ³⁷ and R ³⁸ do not exist, and when Z ³¹ is a nitrogen atom, R ³⁸ does not exist. If Z ⁴¹ is an oxygen atom ^{R 47} and ^{R 48} are ^absent, when ^{Z 41} is a nitrogen atom ^{R 48} is absent. When Z ⁵¹ is an oxygen atom, R ⁵⁹ and R ⁶⁰ do not exist, and when Z ⁵¹ is a nitrogen atom, R ⁶⁰ does not exist.
In formula (A),
α is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms in the main chain, and the substituted alkylene group is any one selected from the group consisting of a benzyl group, an alkoxycarbonyl group, and a phenyl group. At least a group of species. Furthermore, the substituted alkylene group may have a group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group as a substituent. One of CH _{2 in} the main chain of the alkylene group may be replaced with O, S, NR ¹²² (wherein R ¹²² represents a hydrogen atom or an alkyl group).
β is a substituted or unsubstituted phenylene group, and the substituted phenylene group is any one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a nitro group, a halogen group, or an alkoxy group. At least. The substituted phenylene group may have a group selected from the group consisting of a hydroxy group, a thiol group, an amino group, and a carboxyl group as a substituent.
γ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms in the main chain, or an alkyl group having 1 to 6 carbon atoms in the main chain substituted with an alkyl group having 1 to 6 carbon atoms. One of CH _{2 in} the main chain of the alkyl group may be replaced with O, S, or NR ¹²³ (wherein R ¹²³ represents a hydrogen atom or an alkyl group).
At least one of α, β, and γ is a group having a substituent, and the substituent is at least one group selected from the group consisting of a hydroxy group, a thiol group, an amino group, a carboxyl group, and a methoxy group. is there. l and m are each independently 0 or 1, and the sum of l and m is 0 or more and 2 or less. )   An electrophotographic photosensitive member according to any one of claims 1 to 5, 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.