JP7114408B2 - Electrophotographic photoreceptor manufacturing method and electrophotographic photoreceptor manufactured by the manufacturing method - Google Patents

Description

The present invention relates to a method for producing an electrophotographic photoreceptor and an electrophotographic photoreceptor produced by the method.

For the purpose of improving wear resistance and cleanability of an electrophotographic photoreceptor, a technique of adding organic fine particles to a surface layer containing a curable resin or a resin having a crosslinked structure is known.
Patent Document 1 discloses a technique for producing an electrophotographic photoreceptor excellent in abrasion resistance and cleanability by subjecting acrylic resin particles or melamine resin particles added to a surface layer containing a curable resin to a specific surface treatment. is described.
Patent Document 2 discloses a technique of designing the surface of a surface layer containing a resin having a cross-linked structure and acrylic resin particles to have a desired roughness to produce an electrophotographic photoreceptor having both wear resistance and cleanability. Have been described.
In Patent Document 3, an electrophotographic photoreceptor having both wear resistance and cleanability is prepared by designing the surface of a surface layer containing a resin having a crosslinked structure, inorganic fine particles, and melamine resin particles to a desired roughness. technology is described.

JP 2016-95340 A JP 2006-267467 A JP 2015-114453 A

However, the manufacturing process of the electrophotographic photoreceptor of Patent Documents 1 and 2 requires a surface treatment process for acrylic resin particles and melamine resin particles. In addition, the production steps of Patent Documents 1 to 3 required a step of dispersing the acrylic resin particles and the melamine resin particles. The problem with either technique is that the number of man-hours required for manufacturing increases. Further, it is known that the improvement of cleanability of the electrophotographic photoreceptor is achieved by improving the lubricity of the surface layer of the electrophotographic photoreceptor.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a simple method for producing an electrophotographic photoreceptor having excellent wear resistance and lubricity and containing at least one of acrylic resin particles and melamine resin particles in a surface layer.

The above objects are achieved by the present invention described below. That is, the method for producing an electrophotographic photoreceptor according to the present invention comprises a compound having a monovalent hydrocarbon group having 7 or more carbon atoms and a polymerizable functional group in the same molecule, and a hole-transporting compound having a polymerizable functional group. A coating solution for forming a surface layer containing a compound and at least one of acrylic resin particles and melamine resin particles is applied, and the formed coating film is cured to form the surface layer.

INDUSTRIAL APPLICABILITY As described above, according to the present invention, there is provided a simple method for producing an electrophotographic photoreceptor having excellent wear resistance and lubricity, the surface layer of which contains at least one of acrylic resin particles and melamine resin particles. can provide.

1 is a diagram showing an example of a schematic configuration of an electrophotographic apparatus equipped with a process cartridge having the electrophotographic photosensitive member of the present invention; FIG.

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below with reference to preferred embodiments.
In the prior art, man-hours were increased in order to control the state of particles in the surface layer. In the technique of Patent Document 1, the surfaces of acrylic resin particles or melamine resin particles are coated with an inorganic film and an organic component to form a surface layer in order to suppress separation of the acrylic resin particles or melamine resin particles from the surface layer. This is a technique for bonding a curable resin and a coating film of particles by a curing reaction. Therefore, a surface treatment step for acrylic resin particles or melamine resin particles is required.

In the technique of Patent Document 2, surface treatment is applied to the surface of the acrylic resin particles to suppress aggregation of the acrylic resin particles and to control the surface roughness of the surface layer within a desired range, thereby obtaining good cleaning properties. . Therefore, a surface treatment process is required.
According to the technique of Patent Document 3, by surface-treating the surfaces of melamine resin particles, aggregation of the melamine resin particles is suppressed, and by controlling the surface roughness of the surface layer within a desired range, good cleaning properties can be obtained. . Therefore, a surface treatment process is required.

As described above, in the prior art, in the step of forming the surface layer, the balance of the affinity of the other constituents with respect to the acrylic resin particles or the melamine resin particles is poor. It was necessary, and the number of man-hours had increased.

In order to solve the problems that have arisen in the prior art, the composition of the coating solution for forming the surface layer and the method of forming the surface layer were investigated. As a result of investigation, a compound having a monovalent hydrocarbon group having 7 or more carbon atoms and a polymerizable functional group in the same molecule (hereinafter also referred to as "compound b") and a hole-transporting compound having a polymerizable functional group were found. (hereinafter also referred to as “compound c”) and at least one of acrylic resin particles (hereinafter also referred to as “acrylic particles”) and melamine resin particles (hereinafter also referred to as “melamine particles”). By applying a layer-forming coating liquid and curing the formed coating film to form a surface layer, the surface layer contains at least one of acrylic particles and melamine resin particles without increasing the number of steps. It was found that an electrophotographic photoreceptor having excellent lubricity can be produced.

The structure of the coating liquid for surface layer formation and the mechanism by which the film forming method of the present invention solves the problems are considered as follows. First, compound b and compound c dissolve substantially uniformly in an alcoholic solvent having 3 or less carbon atoms. On the other hand, compound b has a higher affinity for acrylic particles and melamine particles than compound c having a charge-transporting skeleton. Therefore, acrylic particles and melamine particles are preferentially surrounded by compound b. At this time, compound b has a polymerizable functional group that is compatible with acrylic particles and melamine particles, and a monovalent hydrocarbon group with 7 or more carbon atoms is considered to face the opposite side to acrylic particles and melamine particles. Enclosed acrylic and melamine particles are somewhat hydrophobic. Acrylic particles and melamine particles having a slightly hydrophobic property do not separate from the coating solution for forming the surface layer, but when the coating solution for forming the surface layer becomes a coating film, the solvent is an alcohol solvent having 3 or less carbon atoms. If so, it is expected that it is likely to be exposed from the coating film in the vicinity of the free interface (interface with air). As a result, the formed surface layer has a high frequency of exposure of the acrylic particles and melamine particles covered with a thin skin composed of the cured products of compound b and compound c. In the electrophotographic process, this surface layer has an irregular shape caused by acrylic particles and melamine particles to reduce frictional force, and the cured product of compound b exposed on the surface together with acrylic particles and melamine particles has lubricity. Therefore, the lubricity is improved. Moreover, since the surface layer itself is composed of a cured product, the wear resistance is improved. Furthermore, since the acrylic particles and melamine particles covered with a thin skin made of the cured product are prevented from being detached from the surface layer, lubricity and wear resistance are maintained even after repeated use.

In the present invention, a coating liquid for forming a surface layer containing compound b, compound c, and at least one of acrylic particles and melamine particles is applied, and the formed coating film is cured to form compound b and compound c. By forming a surface layer containing the copolymer, the three types of materials effectively interact in both the coating liquid and the coating film, and without increasing the number of man-hours for surface treatment of acrylic particles and melamine particles, It is possible to provide a method for producing an electrophotographic photoreceptor which contains at least one of acrylic particles and melamine particles in the surface layer and has excellent abrasion resistance and lubricity.

As described above, the synergistic effect of each configuration makes it possible to achieve the effects of the present invention.

[Manufacturing method of electrophotographic photoreceptor]
A method for producing the electrophotographic photoreceptor of the present invention is shown below. First, there is a method of preparing a coating solution for each layer other than the surface layer, which will be described later, coating the layers in the desired order, and drying. Examples of the coating method of the coating solution for layers other than the surface layer 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 viewpoint of efficiency and productivity.

Subsequently, on each layer other than the surface layer formed by the above method, a coating liquid for forming a surface layer containing compound b, compound c, and at least one of acrylic particles and melamine particles is applied to form a surface layer. In this method, the applied film is cured to form a surface layer.

The coating liquid for forming the surface layer can be prepared by simply mixing and stirring the materials without going through a surface treatment process or a dispersion process of acrylic resin or melamine resin particles.
The method of applying the coating liquid for surface layer formation is not particularly limited as long as it is a method capable of forming a coating film. Coating methods include dip coating, spray coating, inkjet coating, roll coating, die coating, blade coating, curtain coating, wire bar coating, ring coating, and the like. Among these, dip coating is preferable from the viewpoint of efficiency and productivity.

The method of curing the coating film is a method of heating or irradiating the coating film in order to cure the compound having a polymerizable functional group contained in the coating liquid. As a heating method, a hot air drying oven, an infrared heater, an IH heater, or the like can be used. Examples of radiation include ultraviolet rays and electron beams. At this time, if necessary, a known polymerization initiator may be used. In addition, for the purpose of improving properties, heat treatment may be performed separately before and after curing.

Compound b is described below. A monovalent hydrocarbon group having 7 or more carbon atoms is a linear or branched unsubstituted alkyl group. In the case of a branched alkyl group, the sum of the number of carbon atoms in the main chain and the number of carbon atoms in the branched chain is 7 or more. If the number of carbon atoms is less than 7, an electrophotographic photoreceptor with excellent lubricity cannot be produced. Examples of the polymerizable functional group of compound b include vinyl group, acryloyl group, methacryloyl group, epoxy group, hydroxyl group, alkoxy group, carboxy group, amino group, isocyanate group, styryl group and the like.

式（１）中、Ｒ^１は、水素原子、または、メチル基である。Ｒ^２は、炭素数が７以上の直鎖状または分岐状の無置換のアルキル基である。分岐状のアルキル基である場合、主鎖の炭素数と分岐鎖の炭素数との合計が７以上である。Ｘは－ＯＣＯ－（オキシカルボニル基）または－ＣＯＯ－（カルボニルオキシ基）である。 As the polymerizable functional group, any functional group capable of undergoing a polymerization reaction with the polymerizable functional group possessed by compound c can be arbitrarily selected. The polymerizable functional group may be directly bonded to the hydrocarbon group, may be bonded via a heteroatom such as an oxygen atom, a nitrogen atom, a sulfur atom, or may be bonded via an oxycarbonyl group, a carbonyloxy group, or the like. may be combined with As the polymerizable functional group, an acryloyloxy group and a methacryloyloxy group that bond to a hydrocarbon group through oxygen are more preferable. One molecule of the compound b may have at least one polymerizable functional group. Compound b is more preferably a compound represented by formula (1).

In formula (1), R ¹ is a hydrogen atom or a methyl group. R ² is a linear or branched unsubstituted alkyl group having 7 or more carbon atoms. In the case of a branched alkyl group, the sum of the number of carbon atoms in the main chain and the number of carbon atoms in the branched chain is 7 or more. X is -OCO- (oxycarbonyl group) or -COO- (carbonyloxy group).

Examples of compounds b are shown below.

Compound c is described below. Examples of the polymerizable functional group possessed by the compound c include vinyl group, acryloyl group, methacryloyl group, epoxy group, hydroxyl group, alkoxy group, carboxy group, amino group, isocyanate group and styryl group. The polymerizable functional group may be directly bonded to the hydrocarbon group, or may be bonded via a heteroatom such as an oxygen atom, a nitrogen atom, or a sulfur atom. One molecule of the compound c may have one or more polymerizable functional groups.

Examples of hole-transporting groups possessed by compound c include
a group derived by removing a hydrogen atom of a benzene ring or an alkyl group of a triarylamine compound having an alkyl group as a substituent or not having a substituent;
a group derived by removing the hydrogen atom of the benzene ring of the hydrazone compound,
A group derived by removing a hydrogen atom from a benzene ring of a stilbene compound, and the like.

式（２）中、Ｐ^１は重合性官能基であり、下記式（３）で示される１価の基、下記式（４）で示される１価の基、下記式（５）、または下記式（６）で示される基である。ａは、１以上４以下の整数であり、ａが２以上である場合、ａ個のＰ１は同一であっても異なっていてもよい。 Compound c is more preferably a compound represented by the following formula (2).

In formula (2), P ¹ is a polymerizable functional group, a monovalent group represented by the following formula (3), a monovalent group represented by the following formula (4), the following formula (5), or the following It is a group represented by formula (6). a is an integer of 1 or more and 4 or less, and when a is 2 or more, the a pieces of P1 may be the same or different.

式（７）中、Ｒ^３１は置換基として炭素数１以上３以下のアルキル基を有してもよいフェニル基、または置換基として炭素数１以上３以下のアルキル基を有してもよいビフェニル基を示す。Ｒ^３２およびＲ^３３は置換基として炭素数１以上３以下のアルキル基を有してもよいフェニル基を示す。また、Ｒ^３１、Ｒ^３２およびＲ^３３はそれぞれ同一であっても異なっていてもよい。

式（８）中、Ｒ^３４、Ｒ^３５、Ｒ^３６およびＲ^３７は置換基として炭素数１以上３以下のアルキル基を有してもよいフェニル基を示す。また、Ｒ^３４、Ｒ^３５、Ｒ^３６およびＲ^３７はそれぞれ同一であっても異なっていてもよい。Ｒ^３８およびＲ^３９は水素原子、または炭素数１以上３以下のアルキル基を示す。また、Ｒ^３８およびＲ^３９はそれぞれ同一であっても異なっていてもよい。 In formula (2) above, Z is a hole-transporting group. A hydrogen adduct obtained by substituting ^a hydrogen atom for the binding site of Z to P1 in the above formula (2) is a compound represented by the following formula (7) or (8).

In formula (7), R ³¹ is a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent, or a biphenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent. indicates a group. R ³² and R ³³ represent a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent. Also, R ³¹ , R ³² and R ³³ may be the same or different.

In formula (8), R ³⁴ , R ³⁵ , R ³⁶ and R ³⁷ each represent a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent. Also, R ³⁴ , R ³⁵ , R ³⁶ and R ³⁷ may be the same or different. R ³⁸ and R ³⁹ each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Also, R ³⁸ and R ³⁹ may be the same or different.

Examples of the hole-transporting compound (compound c) having a polymerizable functional group are shown below.

The acrylic resin particles contained in the surface layer forming coating liquid are described below. An acrylic resin is a resin containing a polymer of acrylic acid ester or methacrylic acid ester. Among them, styrene acrylic resin particles are preferred. There are no particular restrictions on the degree of polymerization of the acrylic resin or styrene-acrylic resin, or whether the resin is thermoplastic or thermosetting.
Although the particle size of the acrylic resin particles can be arbitrarily designed, it is more preferably 1.0 μm or less.

Commercially available acrylic resin particles that can be used in the present invention include fine spheres manufactured by Nippon Paint Industrial Coatings Co., Ltd.: FS-101, FS-102, FS-107, FS-201, FS-301, FS-701. , MG-155, MG-351, MG-451, TECHPOLYMER manufactured by Sekisui Plastics Co., Ltd.: SSX-101, SSX-102, SSX-103, SSX-104, SSX-105, viaduct particles manufactured by JSR Corporation: SX8002 , polymethyl methacrylate powder manufactured by Sekisui Plastics Co., Ltd.: XX-159AP, XX-160AP, and the like.

The ratio B/A of the mass B of the compound b to the mass A of the acrylic resin particles in the surface layer forming coating liquid can be arbitrarily designed, but is preferably 8% by mass or more.

The ratio A/(A+B+C) of the mass A of the acrylic resin particles to the sum of the mass B of the compound (b) in the coating liquid for forming the surface layer, the mass C of the compound c, and the mass A of the acrylic resin particles is designed arbitrarily. Although it is possible, 10% by mass or more and 25% by mass or less is more preferable.

The melamine resin particles contained in the surface layer forming coating liquid are described below. Melamine resin particles are produced by polycondensation of melamine and formaldehyde. Benzoguanamine may be added to increase compatibility. Among them, particles containing a melamine-formaldehyde resin as a main component are preferable, and particles composed of a melamine-formaldehyde resin are more preferable. The particle size of the particles containing the melamine resin particles can be arbitrarily designed, but is preferably 1.0 μm or less.

Commercially available melamine resin particles that can be used in the present invention include, for example, Nippon Shokubai Co., Ltd. Eposter: SS, S, FS, S6, and the like.

The ratio B/D of the mass B of the compound b to the mass D of the melamine resin particles in the surface layer forming coating liquid can be arbitrarily designed, but is preferably 10% by mass or more.

The ratio D/(D+B+C) of the mass D of the melamine resin particles to the sum of the mass B of the compound b in the coating liquid for forming the surface layer, the mass C of the compound c, and the mass A of the melamine resin particles can be designed arbitrarily. , more preferably 13% by mass or more and 32% by mass or less.

The structure and layers of the electrophotographic photoreceptor manufactured by the manufacturing method of the present invention will be described below.

<Support>
An electrophotographic photoreceptor manufactured by the manufacturing method of the present invention has a support. The support is preferably a conductive support having electrical conductivity. Further, the shape of the support includes a cylindrical shape, a belt shape, a sheet shape, and the like. Among them, a cylindrical support is preferable. Further, the surface of the support may be subjected to electrochemical treatment such as anodization, blasting treatment, cutting treatment, or the like.
The material of the support is preferably metal, resin, glass, or the like.
Examples of metals include aluminum, iron, nickel, copper, gold, stainless steel, and alloys thereof. Among them, an aluminum support using aluminum is preferable.
Conductivity may also be imparted to the resin or glass by treatment such as mixing or coating with a conductive material.

<Conductive layer>
In the electrophotographic photoreceptor produced by the production method of the invention, a conductive layer may be provided on the support. By providing the conductive layer, it is possible to cover scratches and irregularities on the surface of the support and to control reflection of light on the surface of the support.
The conductive layer preferably contains conductive particles and a resin.

Materials for the conductive particles include metal oxides, metals, and carbon black.
Metal oxides include zinc oxide, aluminum oxide, indium oxide, silicon oxide, zirconium oxide, tin oxide, titanium oxide, magnesium oxide, antimony oxide, and bismuth oxide. Metals include aluminum, nickel, iron, nichrome, copper, zinc, silver and the like.
Among these, metal oxides are preferably used as the conductive particles, and titanium oxide, tin oxide, and zinc oxide are particularly preferably used.
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 the metal oxide may be doped with an element such as phosphorus or aluminum or an oxide thereof.
Also, the conductive particles may have a laminated structure including core particles and a coating layer that covers the particles. Examples of core material particles include titanium oxide, barium sulfate, and zinc oxide. Metal oxides, such as tin oxide, are mentioned as a coating layer.
When metal oxides are used as the conductive particles, the volume average particle diameter is preferably 1 nm or more and 500 nm or less, more preferably 3 nm or more and 400 nm or less.

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

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 conductive layer coating liquid containing each of the above materials and a solvent, forming a coating film thereon, and drying the coating film. Solvents used in the coating liquid include alcohol solvents, sulfoxide solvents, ketone solvents, ether solvents, ester solvents, aromatic hydrocarbon solvents and the like. Examples of the dispersion method for dispersing the conductive particles in the conductive layer coating liquid include methods using a paint shaker, a sand mill, a ball mill, and a liquid collision type high-speed disperser.

<Undercoat layer>
In the electrophotographic photoreceptor manufactured by the manufacturing method of the present invention, an undercoat layer may be provided on the support or the conductive layer. By providing the undercoat layer, the adhesion function between the layers is enhanced, and the electrophotographic photoreceptor can be provided with a charge injection blocking function.
The undercoat layer preferably contains a resin. Alternatively, the undercoat layer may be formed as a cured film by polymerizing a composition containing a monomer having a polymerizable functional group.

Resins include polyester resins, polycarbonate resins, polyvinyl acetal resins, acrylic resins, epoxy resins, melamine resins, polyurethane resins, phenol resins, polyvinyl phenol resins, alkyd resins, polyvinyl alcohol resins, polyethylene oxide resins, polypropylene oxide resins, and polyamide resins. , polyamic acid resins, polyimide resins, polyamideimide resins, cellulose resins, and the like.

Examples of the polymerizable functional group possessed by the monomer having a polymerizable functional group include an isocyanate group, a blocked isocyanate group, a methylol group, an alkylated methylol group, an epoxy group, a metal alkoxide group, a hydroxyl group, an amino group, a carboxyl group, a thiol group, Carboxylic anhydride groups, carbon-carbon double bond groups, and the like.

In addition, the undercoat layer may further contain an electron-transporting material, a metal oxide, a metal, or the like for the purpose of enhancing electrical properties. Among these, electron transport substances and metal oxides are preferably used.
Examples of electron-transporting substances include quinone compounds, imide compounds, benzimidazole compounds, cyclopentadienylidene compounds, fluorenone compounds, xanthone compounds, benzophenone compounds, cyanovinyl compounds, halogenated aryl compounds, silole compounds, and boron-containing compounds. . An electron transporting substance having a polymerizable functional group may be used as the electron transporting substance, and an undercoat layer may be formed as a cured film by copolymerizing the electron transporting substance with the above-mentioned monomer having a polymerizable functional group.
Metal oxides include indium tin oxide, tin oxide, indium oxide, titanium oxide, zinc oxide, aluminum oxide, and silicon dioxide. Metals include gold, silver, and aluminum.
In addition, the undercoat layer may further contain additives.

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 can be formed by preparing an undercoat layer coating solution containing each of the materials and solvents described above, forming a coating film, and drying and/or curing the coating film. Solvents used in the coating liquid include alcohol solvents, ketone solvents, ether solvents, ester solvents, aromatic hydrocarbon solvents and the like.

<Photosensitive layer>
The photosensitive layer of the electrophotographic photoreceptor manufactured by the manufacturing method of the present invention is mainly classified into (1) laminated photosensitive layer and (2) single layer photosensitive layer. (1) The laminated photosensitive layer has a charge generation layer containing a charge generation substance and a charge transport layer containing a charge transport substance. (2) A single-layer type photosensitive layer has a photosensitive layer containing both a charge-generating substance and a charge-transporting substance.

(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 substance and a resin.

Examples of charge-generating substances include azo pigments, perylene pigments, polycyclic quinone pigments, indigo pigments, and phthalocyanine pigments. Among these, azo pigments and phthalocyanine pigments are preferred. Among the phthalocyanine pigments, oxytitanium phthalocyanine pigments, chlorogallium phthalocyanine pigments, and hydroxygallium phthalocyanine pigments are preferred.

The content of the charge-generating substance in the charge-generating layer is preferably 40% by mass or more and 85% by mass or less, more preferably 60% by mass or more and 80% by mass or less, relative to the total mass of the charge-generating layer. preferable.

Resins include polyester resins, polycarbonate resins, polyvinyl acetal resins, polyvinyl butyral resins, acrylic resins, silicone resins, epoxy resins, melamine resins, polyurethane resins, phenol resins, polyvinyl alcohol resins, cellulose resins, polystyrene resins, and polyvinyl acetate resins. , polyvinyl chloride resin, and the like. Among these, polyvinyl butyral resin is more preferable.

The charge generation layer may further contain additives such as antioxidants and UV absorbers. Specific examples include hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, benzophenone compounds, and the like.

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

The charge-generating layer can be formed by preparing a charge-generating layer coating solution containing each of the above materials and a solvent, forming a coating film thereon, and drying the coating film. Solvents used in the coating liquid include alcohol solvents, sulfoxide solvents, ketone solvents, ether solvents, ester solvents, aromatic hydrocarbon solvents and the like.

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

Examples of charge-transporting substances include polycyclic aromatic compounds, heterocyclic compounds, hydrazone compounds, styryl compounds, enamine compounds, benzidine compounds, triarylamine compounds, and resins having groups derived from these substances. be done. Among these, triarylamine compounds and benzidine compounds are preferred.
The content of the charge transport substance in the charge transport layer is preferably 25% by mass or more and 70% by mass or less, more preferably 30% by mass or more and 55% by mass or less, relative to the total mass of the charge transport layer. preferable.

Examples of resins include polyester resins, polycarbonate resins, acrylic resins, and polystyrene resins. Among these, polycarbonate resins and polyester resins are preferred. A polyarylate resin is particularly preferable as the polyester resin.
The content ratio (mass ratio) of the charge transport substance and the resin is preferably 4:10 to 20:10, more preferably 5:10 to 12:10.

The charge transport layer may also contain additives such as antioxidants, UV absorbers, plasticizers and leveling agents. Specific examples include hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, benzophenone compounds, siloxane-modified resins, and silicone oils.

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-transporting layer can be formed by preparing a charge-transporting-layer coating solution containing each of the materials and solvents described above, forming a coating film thereon, and drying the coating film. Solvents used in the coating liquid include alcohol solvents, ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents. Among these solvents, ether solvents and aromatic hydrocarbon solvents are preferred.

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

<Protective layer>
In the present invention, a protective layer may be provided on the photosensitive layer. Durability can be improved by providing a protective layer.
The protective layer preferably contains conductive particles and/or a charge-transporting substance and a resin.

Conductive particles include particles of metal oxides such as titanium oxide, zinc oxide, tin oxide, and indium oxide.
Charge-transporting substances include polycyclic aromatic compounds, heterocyclic compounds, hydrazone compounds, styryl compounds, enamine compounds, benzidine compounds, triarylamine compounds, and resins having groups derived from these substances. Among these, triarylamine compounds and benzidine compounds are preferred.

Examples of resins include polyester resins, acrylic resins, phenoxy resins, polycarbonate resins, polystyrene resins, phenol resins, melamine resins, and epoxy resins. Among them, polycarbonate resins, polyester resins, and acrylic resins are preferred.

Alternatively, the protective layer may be formed as a cured film by polymerizing a composition containing a monomer having a polymerizable functional group. The reaction at that time includes thermal polymerization reaction, photopolymerization reaction, radiation polymerization reaction, and the like. Examples of the polymerizable functional group possessed by the monomer having a polymerizable functional group include an acrylic group and a methacrylic group. A material having charge transport ability may be used as the monomer having a polymerizable functional group.

The protective layer may contain additives such as antioxidants, UV absorbers, plasticizers, leveling agents, and the like. Specific examples include hindered phenol compounds, hindered amine compounds, sulfur compounds, phosphorus compounds, benzophenone compounds, siloxane-modified resins, and silicone oils.

The average film thickness of the protective layer is preferably 0.5 μm or more and 10 μm or less, and more preferably 1 μm or more and 7 μm or less.

The protective layer can be formed by preparing a protective layer coating liquid containing each of the materials and solvents described above, forming a coating film thereon, and drying and/or curing the coating film. As the solvent used for the coating liquid, an alcohol-based solvent having 3 or less carbon atoms is desirable. This is because, among alcohol-based solvents, if the number of carbon atoms is large, the effect of locating the particles is weakened. If the alcohol solvent is contained in an amount of 50% by mass, it may contain a ketone solvent, an ether solvent, a sulfoxide solvent, an ester solvent and an aromatic hydrocarbon solvent.

<Surface layer>
As described above, the layer corresponding to the surface layer is a coating film formed by applying a surface layer forming coating liquid containing compound b, compound c, and at least one of acrylic resin particles and melamine resin particles. is cured to form a surface layer containing a copolymer of compound b and compound c and at least one of acrylic resin particles and melamine resin particles.

The surface layer of the electrophotographic photoreceptor produced by the production method of the present invention is the above protective layer, or in the case of a multilayer photoreceptor having no protective layer, a charge transport layer or a single layer type without a protective layer. In the case of a photoreceptor, it is either a single layer type photoreceptor layer.
The layer corresponding to the surface layer is composed of the above (1-2) charge transport layer, (2) single-layer type photosensitive layer, and the material described in <protective layer> as long as it is formed according to the production method of the present invention. You may

[Process cartridge, electrophotographic device]
A process cartridge having an electrophotographic photoreceptor manufactured by the manufacturing method of the present invention includes at least one means selected from the group consisting of the electrophotographic photoreceptor described above and charging means, developing means, and cleaning means. are integrally supported, and can be detachably attached to the main body of the electrophotographic apparatus.

Further, the electrophotographic apparatus of the present invention is characterized by having the electrophotographic photosensitive member, charging means, exposure means, developing means and transfer means described above.

FIG. 1 shows an example of a schematic configuration of an electrophotographic apparatus having a process cartridge 11 provided with an electrophotographic photosensitive member 1. As shown in FIG.
A cylindrical electrophotographic photosensitive member 1 is rotationally driven about a shaft 2 in the direction of an arrow at a predetermined peripheral speed. The surface of the electrophotographic photosensitive member 1 is charged to a predetermined positive or negative potential by charging means 3 . Although FIG. 1 shows a roller charging method using a roller-type charging member, other charging methods such as a corona charging method, a proximity charging method, and an injection charging method may be used. The surface of the charged electrophotographic photosensitive member 1 is irradiated with exposure light 4 from an exposure means (not shown) to form an electrostatic latent image corresponding to desired image information. The electrostatic latent image formed on the surface of the electrophotographic photoreceptor 1 is developed with toner accommodated in the developing means 5 to form a toner image on the surface of the electrophotographic photoreceptor 1 . A toner image formed on the surface of the electrophotographic photosensitive member 1 is transferred onto a transfer material 7 by transfer means 6 . The transfer material 7 onto which the toner image has been transferred is conveyed to a fixing means 8 where the toner image is fixed and printed out of the electrophotographic apparatus. The electrophotographic apparatus may have a cleaning means 9 for removing deposits such as toner remaining on the surface of the electrophotographic photosensitive member 1 after transfer. Also, a so-called cleanerless system may be used in which the deposits are removed by developing means or the like without separately providing a cleaning means. The electrophotographic apparatus may have a charge removing mechanism for removing charges from the surface of the electrophotographic photosensitive member 1 with pre-exposure light 10 from a pre-exposure unit (not shown). Also, a guide means 12 such as a rail may be provided for attaching/detaching the process cartridge 11 to/from the main body of the electrophotographic apparatus.

The electrophotographic photoreceptor manufactured by the manufacturing method of the present invention can be used for laser beam printers, LED printers, copiers, facsimiles, and multifunction devices thereof.

The present invention will be described in more detail below using examples and comparative examples. The present invention is by no means limited by the following examples, as long as the gist thereof is not exceeded. In the description of the following examples, "parts" are based on mass unless otherwise specified.

<Production of Electrophotographic Photoreceptor>
<Support>
A cylindrical aluminum cylinder with a diameter of 29.9 mm, a length of 357.5 mm and a thickness of 0.7 mm was used as a support.

<Undercoat layer>
As a metal oxide, 100 parts by mass of zinc oxide particles (specific surface area: 19 m ² /g, powder resistance: 4.7×10 ⁶ Ω·cm) was stirred and mixed with 500 parts by mass of toluene. To this, 0.8 part by mass of N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane (trade name: KBM602, manufactured by Shin-Etsu Chemical Co., Ltd.) was added as a silane coupling agent and stirred for 6 hours. Thereafter, toluene was distilled off under reduced pressure, and the residue was dried by heating at 140° C. for 6 hours to obtain surface-treated zinc oxide particles.

Next, polyvinyl butyral (trade name: S-Lec (registered trademark) B BM-1, manufactured by Sekisui Chemical Co., Ltd.) 15 parts by mass and blocked isocyanate (trade name: Sumidule 3175, manufactured by Sumitomo Bayer Urethane) 15 parts by mass was dissolved in the mixed solution. The mixed solution is a mixed solution of 73.5 parts by mass of methyl ethyl ketone and 73.5 parts by mass of 1-butanol.

80.8 parts by mass of the surface-treated zinc oxide particles prepared above and 0.4 parts by mass of 2,3,4-trihydroxybenzophenone (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added to this solution, and the resulting particles were separated into particles having a diameter of 0.005 mm. Using a sand mill apparatus using 8 mm glass beads, the mixture was dispersed in an atmosphere of 23° C. for 3 hours. After dispersion, silicone oil (trade name: SH28PA, manufactured by Dow Corning Toray Co., Ltd.) 0.01 parts by mass, crosslinked polymethyl methacrylate (PMMA) particles (trade name: TECHPOLYMER (registered trademark) SSX-103, Sekisui Plastics Co., Ltd. 5.6 parts by mass of the company's product, average primary particle size 3.1 μm) was added and stirred to prepare a coating liquid for an undercoat layer.

This undercoat layer coating solution was applied onto the support by dip coating, and the resulting coating film was dried at 160° C. for 40 minutes to form an undercoat layer having a thickness of 18 μm.

<Charge generation layer>
The following four materials were placed in a sand mill using glass beads with a diameter of 1 mm, dispersed for 4 hours, and then 700 parts by mass of ethyl acetate was added to prepare a charge generation layer coating liquid.
・Crystal form hydroxygallium phthalocyanine crystal (charge-generating substance) having strong peaks at 7.4° and 28.2° of Bragg angle 2θ±0.2° in CuKα characteristic X-ray diffraction: 20 parts by mass ・Polyvinyl butyral ( Product name: S-Lec (registered trademark) B BX-1, manufactured by Sekisui Chemical Co., Ltd.): 10 parts by mass Compound represented by the following structural formula (A): 0.2 parts by mass Cyclohexanone: 600 parts by mass This charge generation The layer coating liquid was applied onto the undercoat layer by dip coating, and the resulting coating film was dried at 80° C. for 15 minutes to form a charge generation layer having a thickness of 0.18 μm.

この電荷輸送層用塗布液を電荷発生層上に浸漬塗布し、得られた塗膜を３０分間１１０℃で乾燥して、膜厚１８μｍの電荷輸送層を形成した。 <Charge transport layer>
A charge transport layer coating solution was prepared by dissolving the following four materials in a mixed solvent of 600 parts by mass of xylene and 200 parts by mass of dimethoxymethane.
・Compound represented by the following structural formula (B) (charge-transporting substance): 30 parts by mass ・Compound represented by the following structural formula (C) (charge-transporting substance): 60 parts by mass ・Represented by the following structural formula (D) Compound (charge transport material): 10 parts by mass Polycarbonate (trade name: Iupilon (registered trademark) Z400, manufactured by Mitsubishi Engineering-Plastics Corporation, bisphenol Z-type polycarbonate): 100 parts by mass

The charge transport layer coating liquid was applied onto the charge generation layer by dip coating, and the resulting coating film was dried at 110° C. for 30 minutes to form a charge transport layer having a thickness of 18 μm.

<Protective layer>
Next, protective layer coating solutions 1 to 48 were prepared.
In 100 parts by mass of 1-propanol, a group of particles corresponding to the following acrylic resin particles (particles a-1, 2, 3, 4, 5, 6, particles P), a group of melamine resin particles (particles d-1, 2, 3, 4, 5), a group of compounds corresponding to compound b (compound b-4, 5, 6, 10, 11, compound Q, TMPTA), a group of compounds corresponding to compound c (compound c-3 , 5, 6, 7, 9, 10, 11, compound of structural formula (D)) are mixed and stirred in the types and parts by mass shown in Tables 1 and 2 to obtain a protective layer coating solution. 1-45, 47, and 48 were obtained.
To 100 parts by mass of 1-butanol, melamine resin particles (d-3), a compound other than a hole-transporting compound (compound b-9), and a hole-transporting compound (compound c-5) were added in the mass shown in Table 2. The mixture was mixed and stirred in the parts to obtain a protective layer coating liquid 46 .

For the protective layer coating solutions 1 to 25, the ratio B/A of the mass B of the compound b to the mass A of the acrylic resin particles, and the mass B of the compound b in the surface layer forming coating solution of the mass A of the acrylic particles, Table 1 shows the mass C of the compound c and the ratio A/(A+B+C) of the mass A of the acrylic resin particles to the total mass A of the acrylic resin particles.

For the protective layer coating solutions 26 to 48, the ratio B/D of the mass B of the compound b to the mass D of the melamine resin particles, and the mass B of the compound b in the coating solution for forming the surface layer with the mass D of the melamine particles, Table 2 shows the mass C of the compound c and the ratio D/(D+B+C) of the mass D of the melamine resin particles to the total mass D of the melamine resin particles.

[Group of particles corresponding to acrylic resin particles]
Particle a-1 XX-159AP manufactured by Sekisui Plastics Co., Ltd.
(Polymethyl methacrylate particles, particle size 0.1 μm)
Particle a-2 XX-160AP manufactured by Sekisui Plastics Co., Ltd.
(Polymethyl methacrylate particles, particle size 0.1 μm)
Particle a-3 SSX-102 manufactured by Sekisui Plastics Co., Ltd.
(Polymethyl methacrylate particles, particle size 2.0 μm)
Particle a-4 MG-451 manufactured by Nippon Paint Industrial Coatings Co., Ltd.
(Polystyrene acrylic particles, particle size 0.1 μm)
Particle a-5 Nippon Paint Industrial Coatings Co., Ltd. FS-201
(Polystyrene acrylic particles, particle size 0.5 μm)
Particle a-6 Nippon Paint Industrial Coatings Co., Ltd. FS-301
(Polystyrene acrylic particles, particle size 1.0 μm)
Particle P Shin-Etsu Chemical Co., Ltd. QSG-170
(Silica particles, particle size 0.17 μm)

[Group of Particles Corresponding to Melamine Resin Particles]
Particle d-1 Eposter SS manufactured by Nippon Shokubai Co., Ltd.
(Melamine/formaldehyde particles, particle size 0.1 μm)
Particle d-2 Eposter S manufactured by Nippon Shokubai Co., Ltd.
(Melamine/formaldehyde particles, particle size 0.2 μm)
Particle d-3 Eposter S6 manufactured by Nippon Shokubai Co., Ltd.
(Melamine/formaldehyde particles, particle size 0.4 μm)
Particle d-4 Eposter S12 manufactured by Nippon Shokubai Co., Ltd.
(Melamine/formaldehyde particles, particle size 1.2 μm)
Particle d-5 Eposter MS manufactured by Nippon Shokubai Co., Ltd.
(Melamine/formaldehyde particles, particle size 2.0 μm)

ダイセル・サイテック株式会社製トリメチロールプロパントリアクリレート（ＴＭＰＴＡ） [Group of compounds corresponding to compound b]

Trimethylolpropane triacrylate (TMPTA) manufactured by Daicel-Cytec Co., Ltd.

[Group of compounds corresponding to compound c]

These protective layer coating solutions were applied onto the charge transport layer by dip coating. The resulting coating film was then dried at 40° C. for 6 minutes. After that, the coated film was irradiated with an electron beam for 1.6 seconds in nitrogen while rotating the support (body to be irradiated) at 200 rpm. The electron beam conditions were set so that the absorbed dose was 8000 Gy at an accelerating voltage of 70 kV. Subsequently, the coating film was heated by raising the temperature from 25° C. to 120° C. over 30 seconds in nitrogen. The oxygen concentration in the atmosphere during electron beam irradiation and subsequent heating was 15 ppm. Next, a protective layer having a thickness of 5 μm was formed by performing heat treatment at 100° C. for 30 minutes in the atmosphere.

Electrophotographic photoreceptors 1 to 48 were produced using protective layer coating solutions 1 to 48 shown in Table 3 as described above.
Using Protective Layer Coating Liquids 1 to 48 and Electrophotographic Photoreceptors 1 to 48, the following evaluations were carried out.

[evaluation]
<Evaluation of change over time of coating solution for protective layer>
The protective layer coating solution was placed in a glass bottle, sealed, and allowed to stand in a cool and dark place for one week. Results are shown in Tables 1 and 2. More specifically, in the protective layer coating liquids 10, 25, 44, and 45, the particles sedimented. When these glass bottles were shaken by hand to check whether they were dispersed again, protective layer coating liquid 25 was not dispersed, but protective layer coating liquids 10, 44, and 45 were dispersed again. Therefore, the coating liquid for surface layer formation prepared by the manufacturing method of the present invention has a long pot life, which is preferable from the viewpoint of productivity.

<Evaluation of function of electrophotographic photoreceptor>
The produced electrophotographic photoreceptor was evaluated whether or not there was any problem in basic electrophotographic photoreceptor functions such as electrical characteristics and developability. Electrophotographic photoreceptors 1, 8, 11, 13, 19, 26, 32, 34, 39, 40, and 42 were installed in image RUNNER (registered trademark)-ADV 4545 (manufactured by Canon Inc.), and problems with images were observed. It was confirmed that no When 10,000 sheets of A4 paper with a printing ratio of 5% were printed in an environment of 23° C. and 50% RH, no abnormalities occurred in the images of any of the electrophotographic photosensitive members. Therefore, the electrophotographic photoreceptor produced by the manufacturing method of the present invention satisfies the function as an electrophotographic photoreceptor.

<Evaluation of lubricity>
The dynamic friction coefficient was measured with a rotary Haydon. The rotary Haydon has a mechanism that supports and rotates the electrophotographic photosensitive member, a mechanism that abuts and supports the cleaning blade on the surface of the electrophotographic photosensitive member at a desired angle and penetration amount, and a mechanism that abuts and supports the cleaning blade. and detection means for detecting the As the cleaning blade, a urethane rubber blade having a Wallace hardness (value of M method in IRHD hardness test method) of 77 degrees and a rebound resilience of 20% was used. A blade with a width of 10 mm, a thickness of 2 mm, and a free length of 8 mm was rotated at a set angle of 25°, a penetration depth of 1.4 mm, and a rotation speed of 168 rpm. After one minute from the start of rotation, read the tangential load and normal load of the electrophotographic photosensitive member at the blade contact portion obtained by the detection means, and divide the tangential load by the normal load. to calculate the dynamic friction coefficient. Table 2 shows the results. The electrophotographic photoreceptors 21, 24, 25, and 47 could not be measured for their dynamic friction coefficients because the blades were curled during the measurement.

<Abrasion resistance evaluation>
Using Heidon: Type 14 manufactured by Sintokagaku Co., Ltd., the easiness of scratching of the surface layer was evaluated by simulating the method of surface scratch hardness JIS K5600. A conical scratching needle (diamond needle) having a R of 0.03 mm at the tip was brought into contact with the electrophotographic photosensitive member, and a vertical load of 30 g was applied with a weight. Heidon: The electrophotographic photosensitive member was scratched at a speed of 1 rpm by a mechanism for rotating and supporting the electrophotographic photosensitive member prepared separately from Type 14, and the depth of scratches formed in the circumferential direction of the electrophotographic photosensitive member was evaluated. The depth is measured using a surface roughness measuring machine Surfcoder SE3500 manufactured by Kosaka Laboratory Co., Ltd., and the maximum height Rmax according to JISB 0601 (1982) is measured in the generatrix direction of the electrophotographic photosensitive member (the direction across the scratches). It was measured. Table 3 shows the results.

According to the manufacturing method of the present invention, at least one of the acrylic resin particles and the melamine resin particles is added to the surface layer by simply mixing and stirring at least one of the acrylic resin particles and the melamine resin particles in the coating liquid, without increasing the number of man-hours. It is possible to produce an electrophotographic photoreceptor excellent in abrasion resistance and lubricity.

REFERENCE SIGNS LIST 1 electrophotographic photosensitive member 2 shaft 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 (15)

organic resin particles of at least one of acrylic resin particles and melamine resin particles;
a compound having a monovalent hydrocarbon group having 7 or more carbon atoms and a polymerizable functional group in the same molecule;
a hole-transporting compound having a polymerizable functional group;
A method for producing an electrophotographic photoreceptor, comprising applying a coating liquid for forming a surface layer containing: and curing the formed coating film to form a surface layer. 2. The method of manufacturing an electrophotographic photoreceptor according to claim 1, wherein the organic resin particles are acrylic resin particles. The ratio B/A of the mass B of the compound having the monovalent hydrocarbon group having 7 or more carbon atoms and the polymerizable functional group in the same molecule to the mass A of the acrylic resin particles is 8% by mass or more. 3. The method for producing an electrophotographic photoreceptor according to claim 2. The mass A of the acrylic resin particles, the mass B of the compound having the monovalent hydrocarbon group having 7 or more carbon atoms and the polymerizable functional group in the same molecule, and the hole-transporting compound having the polymerizable functional group. 4. The electrophotographic photoreceptor according to claim 2, wherein the ratio A/(A+B+C) of the mass A of the acrylic resin particles to the total mass C of the acrylic resin particles is 10% by mass or more and 25% by mass or less. manufacturing method. 5. The method for producing an electrophotographic photoreceptor according to claim 2, wherein the acrylic resin particles are particles containing styrene-acrylic resin. 2. The method of manufacturing an electrophotographic photoreceptor according to claim 1, wherein the organic resin particles are melamine resin particles. A ratio B/D of a mass B of a compound having a monovalent hydrocarbon group having 7 or more carbon atoms and a polymerizable functional group in the same molecule to the mass D of the melamine resin particles is 10% by mass or more. 7. The method for producing an electrophotographic photoreceptor according to claim 6. The mass D of the melamine resin particles, the mass B of the compound having the monovalent hydrocarbon group having 7 or more carbon atoms and the polymerizable functional group in the same molecule, and the hole-transporting compound having the polymerizable functional group 8. The electrophotographic photoreceptor according to claim 6, wherein the ratio D/(D+B+C) of the mass D of the melamine resin particles to the total mass C of the melamine resin particles is 13% by mass or more and 32% by mass or less. manufacturing method. 9. The method for producing an electrophotographic photoreceptor according to claim 5, wherein the melamine resin particles are particles containing a melamine-formaldehyde resin. Any one of claims 1 to 9, wherein the compound having a monovalent hydrocarbon group with 7 or more carbon atoms and a polymerizable functional group in the same molecule is a compound represented by the following formula (1): 2. The method for producing an electrophotographic photoreceptor according to item 1.

(In Formula (1), R ¹ is a hydrogen atom or a methyl group. R ² is a linear or branched alkyl group having 7 or more carbon atoms. X is —OCO—(oxy carbonyl group) or -COO- (carbonyloxy group).) 11. Any one of claims 1 to 10, wherein the hole-transporting compound having a polymerizable functional group is a hole-transporting compound having an acryloyloxy group or a hole-transporting compound having a methacryloyloxy group. 2. The method for producing an electrophotographic photoreceptor according to item 1. 11. The method for producing an electrophotographic photoreceptor according to any one of claims 1 to 10, wherein the hole-transporting compound having a polymerizable functional group is a compound represented by the following formula (2). .

(In the formula (2), P ¹ is a polymerizable functional group, is a monovalent group represented by the following formula (3), a monovalent group represented by the following formula (4), the following formula (5), Or a group represented by the following formula (6), where a is an integer of 1 or more and 4 or less, and when a is 2 or more, a P1 may be the same or different.Z is a hole-transporting group A hydrogen adduct obtained by substituting a hydrogen atom for P ¹ in the above formula (2) is a compound represented by the following formula (7) or (8).

In formula (7), R ₃₁ is a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent, or a biphenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent. indicates a group. R ³² and R ³³ represent a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent. Also, R ³¹ , R ³² and R ³³ may be the same or different.

In formula (8), R ³⁴ , R ³⁵ , R ³⁶ and R ³⁷ each represent a phenyl group optionally having an alkyl group having 1 to 3 carbon atoms as a substituent.
Also, R ³⁴ , R ³⁵ , R ³⁶ and R ³⁷ may be the same or different.
R ³⁸ and R ³⁹ each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
Also, R ³⁸ and R ³⁹ may be the same or different. ) 13. The method for producing an electrophotographic photoreceptor according to claim 1, wherein the organic resin particles have a particle diameter of 1.0 μm or less. 14. The method for producing an electrophotographic photoreceptor according to any one of claims 1 to 13, wherein the surface layer forming coating liquid contains an alcohol having 3 or less carbon atoms. In an electrophotographic photoreceptor having a support and a photosensitive layer formed on the support, the surface layer of the electrophotographic photoreceptor comprises a monovalent hydrocarbon group having 7 or more carbon atoms and a polymerizable functional group of the same molecule. An electrophotographic photoreceptor comprising a compound contained therein, a hole-transporting compound having a polymerizable functional group, and at least one of acrylic resin particles and melamine resin particles.

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