JP2000275886A - Electrophotographic photoreceptor and process cartridge and image forming device using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a photoreceptor excellent in wear resistance, scratch resistance or the like by incorporating a specified siloxane hardening resin into the surface layer of an electrophotographic photoreceptor and incorporating an org. metal compd. and/or silane coupling agent into an intermediate layer. SOLUTION: The surface layer of the electrophotographic photoreceptor contains a siloxane hardening resin containing a structural unit expressed by the formula, and the intermediate layer contains an org. metal compd. and/or silane coupling agent. In the formula, X is a donating group of charge transfer ability and is coupled to Z in the formula through the carbon atom which constitutes the donating group, Z is a divalent or higher-valence atom or group except for the adjacent coupling atoms (Si and C). The divalent or higher- valence atom or group Z except for the adjacent coupling atoms (Si and C) preferably means a divalent or higher-valence atoms or groups such as an oxygen atom (O), sulfur atom (S) and NR (R is a hydrogen atom or monovalent org. group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member, a process cartridge having the electrophotographic photosensitive member, and an image forming apparatus.

[0002]

2. Description of the Related Art Conventionally, an inorganic photoconductor containing an inorganic photoconductive substance has been used for an electrophotographic photoconductor. Recently, however, many organic photoconductors containing an organic photoconductive substance in place of the inorganic photoconductor have been used. Became used. The above organic photoreceptor (hereinafter, referred to as
(Photoconductors) are superior to inorganic photoconductors because materials that can be used for various exposure light sources from visible light to infrared light can be easily developed, materials that do not cause environmental pollution can be selected, and manufacturing costs are low. However, the only drawback is that the mechanical strength is weak, and the surface of the photosensitive layer is worn and damaged during copying or printing of a large number of sheets, so that the electrophotographic performance tends to deteriorate.

The surface of the photoreceptor is susceptible to wear and damage due to direct application of electrical and mechanical external force by a charger, a developing unit, a transfer unit, a separator, a cleaning unit, and the like, and the durability thereof is improved. Has been requested. Specifically, there has been a demand for an improvement in mechanical durability against abrasion and scratches on the surface of the photoreceptor due to rubbing, film contamination and the like during entry of foreign substances and paper jams. Above all, with respect to durability against scratches and film peeling due to impact, a strength as high as that of an inorganic photoreceptor is strongly required. Further, there is a demand for durability against deterioration of the surface of the photoreceptor due to ozone or active oxygen generated during corona charging.

In order to satisfy the various characteristics required for the surface of the photoreceptor, various improvement methods have been proposed so far. That is, it has been reported that the use of BPZ polycarbonate as a binder resin on the surface of a photoreceptor improves the surface wear characteristics, toner filming characteristics, and the like. Japanese Patent Application Laid-Open No. Hei 6-118681 reports that a curable silicone resin containing colloidal silica is used for a protective layer on the surface of a photoreceptor.

However, a photoreceptor using BPZ polycarbonate as a binder resin still lacks abrasion resistance and does not have satisfactory durability. on the other hand,
The surface layer of a curable silicone resin containing colloidal silica has improved abrasion resistance, but the electrophotographic properties during repeated use are inadequate, and fog and image blur are liable to occur during repeated use. It was not enough.

[0006] As a method of improving such a defect, Japanese Patent Application Laid-Open No. 9-124943 and Japanese Patent Application Laid-Open No.
Japanese Patent Application Laid-Open No. 4-64204 proposes a photoreceptor having, as a surface layer, a resin layer in which a hole transporting compound is bound in a curable organic Si-based polymer. However, this resin layer is liable to cause fogging and image blur in a high humidity environment and does not have sufficient durability. In addition, such a curable organic Si compound film has high abrasion resistance, but has drawbacks such as being easily damaged by an external impact and easily peeling off the photosensitive layer. Had insufficient film strength and adhesiveness.

[0007]

DISCLOSURE OF THE INVENTION The present invention has been proposed based on the above-mentioned circumstances, and its object is to provide:
The hardness of the photosensitive layer surface is high, and it is excellent in abrasion resistance, scratch resistance and adhesion, and when the image is repeatedly formed, especially when the image is repeatedly formed under high temperature and high humidity, An object of the present invention is to provide a photoreceptor capable of stably obtaining a good image without fogging or image blurring without causing fatigue deterioration of electrophotographic performance, a process cartridge using the photoreceptor, and an image forming apparatus. .

[0008]

As a result of diligent studies by the present inventors, it has been found that the above object is achieved by the following constitution.

1. In an electrophotographic photosensitive member having a photosensitive layer on a conductive support via an intermediate layer, the surface layer of the electrophotographic photosensitive member is formed of a siloxane-based cured resin containing a structural unit represented by the following general formula (1). An electrophotographic photoreceptor, wherein the intermediate layer is a layer containing an organometallic compound and / or a silane coupling agent.

[0010]

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(Wherein X is a charge transporting group,
It is a group bonded to Z in the formula via a carbon atom constituting the imparting group, and Z is a divalent or higher valent atom or group other than adjacent bonding atoms (Si and C). ) 2. In the general formula (1), X is a charge transporting ability-imparting group, which is a group bonded to Z in the formula via a carbon atom constituting the imparting group, and Z is an oxygen atom (O), 2. The electrophotographic photoreceptor according to the above 1, wherein the photoreceptor is an atom (S) or an NR group, and R is a hydrogen atom or a monovalent organic group.

3. 3. The electrophotographic photoreceptor according to the above item 1 or 2, wherein the organometallic compound contained in the intermediate layer is a metal alkoxide or an organic metal chelate.

4. 4. The electrophotographic photoreceptor according to any one of the items 1 to 3, wherein the intermediate layer is a layer containing an organic metal chelate and a silane coupling agent.

5. 5. The electrophotographic photoreceptor according to the above item 3 or 4, wherein the organometallic chelate contained in the intermediate layer is represented by the following general formula (2).

Formula (2) (R ¹ O) _l -M- (K) _m (wherein R ¹ is an alkyl group, M is zirconium,
A chelating group K representing titanium or aluminum
Represents an acetoacetic ester group or a β-diketone residue,
l and m represent an integer of 1 or more. However, when M is zirconium or titanium, l + m is 4, and when M is aluminum, l + m is 3. ) 6. The electrophotographic photosensitive member according to any one of the above items 1 to 4, wherein the silane coupling agent contained in the intermediate layer is represented by the following general formula (3).

Formula (3) (Q) _p —Si (Y) _q — (A) _r (wherein Q represents a halogen atom, an alkoxy group or an amino group, A represents an alkyl group or an aryl group, and functional group Y -BOOC (R ') C = CH 2, -BNHR " or .R representing the -BNH _2' represents an alkyl group, R" represents an alkyl group or an aryl group, B is an alkylene radical - Represents an alkylene group containing O-, -NH-, -CO-, p and q each represent an integer of 1 or more, r represents an integer of 0 or more, and p + q + r is 4.) The electrophotographic photoreceptor according to any one of Items 1 to 6, wherein the surface layer contains a hindered amine or a hindered phenol compound.

8. An image forming apparatus, comprising: performing image formation through charging, image exposure, development, transfer, separation, and cleaning using the electrophotographic photosensitive member according to any one of the above items 1 to 7.

9. 8. It is manufactured by combining the electrophotographic photosensitive member according to any one of the above items 1 to 7 with at least one of a charger, an image exposure device, a developing device, a transfer device, a separator, and a cleaning device. And process cartridge.

The present invention will be described in detail.

The photoreceptor of the present invention is a photoreceptor having a photosensitive layer provided on a conductive support via an intermediate layer, and the surface layer of the photoreceptor has a structure represented by the general formula (1). It is characterized in that it is composed of a siloxane-based cured resin containing a structural unit having a charge-transporting ability-providing group as shown below, and furthermore, the intermediate layer is an organometallic compound, particularly an organometallic compound of the general formula (2) and / or It is characterized by comprising a layer containing the silane coupling agent of the general formula (3), whereby a highly durable photoreceptor unique to the present invention is obtained.

<Structure of Surface Layer> The surface layer of the photoreceptor of the present invention is a layer composed of a siloxane-based cured resin containing the charge transporting ability-imparting group X of the general formula (1). For example, an alkyl (poly) siloxane-based compound and / or an aromatic (poly) siloxane-based compound having a hydrolyzable group such as a silanol group or an alkoxy group,
Reacting a charge transporting compound having a functional group including a charge transporting ability-imparting group X of the general formula (1) and a divalent or higher valent atom other than adjacent bonding atoms (Si and C) or a group Z; It is obtained by adding a crosslinking agent or a curing catalyst and curing.

In the present invention, adjacent bonding atoms (S
A divalent or higher valent atom or group Z other than i and C) is preferably a divalent or higher valent such as an oxygen atom (O), a sulfur atom (S) or NR (R is a hydrogen atom or a monovalent organic group). An atom or group, and the charge transporting ability-imparting group X in the general formula (1)
Is bonded to the silicon atom (Si) of the (poly) siloxane-based compound via the Z, and is cross-linked and cured to obtain a target siloxane-based cured resin. When Z is NR, R is a hydrogen atom or a monovalent organic group, and the organic group may be a charge transport ability-imparting group X.

<< Compound Containing Charge-Transporting Capability-Adding Group X >> A functional group containing the charge-transporting ability-providing groups X and Z of the general formula (1) in the structure contained in the siloxane-based cured resin according to the present invention. For example, charge transporting compounds having a functional group such as OH, SH, and NH ₂ are roughly classified into hole transporting compounds (p
-Type charge transporting) compound and electron transporting (n-type charge transporting)
There are compounds. Examples of the p-type charge transporting compound include:
For example, oxazole, oxadiazole, thiazole,
Triazole, imidazole, imidazolone, imidazoline, bisimidazolidine, styryl, hydrazone, benzidine, pyrazoline, stilbene compound, amine, oxazolone, benzothiazole, benzimidazole,
Quinazoline, benzofuran, acridine, phenazine,
Examples include, but are not limited to, aminostilbene, poly-N-vinylcarbazole, poly-1-vinylpyrene, poly-9-vinylanthracene or derivatives thereof.

Further, examples of the n-type charge transporting compound include succinic anhydride, maleic anhydride, phthalic anhydride, pyromellitic anhydride, melitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, nitrobenzene, Nitrobenzene, trinitrobenzene, tetranitrobenzene, nitrobenzonitrile, picryl chloride, quinone chlorimide, chloranil, bromanil,
Benzoquinone, naphthoquinone, diphenoquinone, tropoquinone, anthraquinone, 1-chloroanthraquinone,
Dinitroanthraquinone, 4-nitrobenzophenone,
4,4′-dinitrobenzophenone, 4-nitrobenzalmalone dinitrile, α-cyano-β- (p-cyanophenyl) -2- (p-chlorophenyl) ethylene, 2,
7-dinitrofluorene, 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, 9-fluorenylidenedicyanomethylenemalononitrile, polynitro-9-fluoronylidenedicyanomethylenemalononitrile, Picric acid, o-nitrobenzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid,
Pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,
Examples include, but are not limited to, compounds such as 5-dinitrosalicylic acid, phthalic acid, melitic acid, and derivatives thereof.

Another definition of the charge transport ability of the structural unit having a charge transport ability-imparting group X according to the present invention is as follows: a detection current value caused by charge transport by a known method such as an ordinary Time-Of-Flight method. Can also be expressed as

In the present invention, the charge transporting ability-imparting group X
Is more preferably a p-type charge-transporting compound having at least one functional group containing Z, and the corresponding charge-transporting ability-imparting group X is a functional group containing Z of the p-type charge-transporting compound. Is a residue from which a C is removed from the residue through the Z to form a Si (poly) siloxane compound.
Is a group bonded to

Among the p-type charge transporting compounds having at least one functional group containing Z, particularly preferred p-type charge transporting compounds useful in the present invention include, for example, the following compounds.

1. Triarylamine compounds

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2. Hydrazone compounds

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3. Stilbene compounds

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4. Benzidine compound

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5. Butadiene compound

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6 Other compounds

[0046]

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In addition, X in the general formula (1) may be present as a crosslink group with the (poly) siloxane compound or bonded as a pendant group in addition to the charge transport ability. In a drying step after application of the coating composition containing the (poly) siloxane compound to which the p-type charge transporting compound has been bonded, the polysiloxane compounds are crosslinked with each other by the presence of a crosslinking agent and a curing catalyst if necessary. By performing (cross-linking), a cured resin layer having high hardness can be formed.

<< Siloxane-based Cured Resin >> As the siloxane-based cured resin for forming the surface layer of the present invention, a (poly) siloxane-based compound such as a monomer, oligomer, or polymer having a siloxane bond in a structural unit in advance may be used. A three-dimensional network structure is formed by adding a curing catalyst or a crosslinking agent to form a new chemical bond. For example, a three-dimensional network structure is formed by a condensation reaction of an alkoxysilane or a silanol. Further, particles such as colloidal silica may be included in the three-dimensional network structure.

To form the (poly) siloxane compound and to crosslink the (poly) siloxane compound to form a cured resin layer, the functional group is preferably a hydroxyl group or a hydrolyzable group described below. It is desirable to have

The hydrolyzable group in the above-mentioned (poly) siloxane compound specifically has a carbon number of 1 to 1, such as a methoxy group, an ethoxy group, an acetoxy group, a propoxy group, a butoxy group, a methoxyethoxy group and a hexaoxy group. An alkoxy group having 6 alkyl groups is preferred.

The (poly) siloxane-based compound used as a raw material of the siloxane-based curable resin in the present invention includes:
Generally, when the number n of hydroxyl groups or hydrolyzable groups bonded to Si atoms is 1, the polymerization reaction of the (poly) siloxane-based compound is suppressed. When n is 2, 3 or 4, a polymerization reaction is likely to occur, and especially when 3 or 4, the crosslinking reaction can be advanced to a high degree. Therefore, by controlling these, it is possible to control the storage stability of the obtained coating layer liquid, the hardness of the coating layer, and the like.

The content ratio of the charge transportability-imparting group X contained in the siloxane-based cured resin layer which is the surface layer (protective layer) of the present invention is preferably in the range of 1 to 70% by weight.
If the amount is less than 1% by weight, the sensitivity is lowered and fogging is increased in the process of image formation, and high quality images cannot be obtained. If the amount is more than 70% by weight, the density of the image is repeatedly decreased due to the potential drop in the image forming process. The decrease is so great that a clear image cannot be obtained.

The thickness of the surface layer (protective layer) of the present invention is preferably from 0.01 to 10 μm. If the thickness is less than 0.01 μm, the photosensitive layer is repeatedly worn and damaged in the course of image formation, and the photoreceptor is deteriorated by fatigue. When the thickness exceeds 10 μm, electrophotographic performance is reduced, fog is easily increased, and it is difficult to form a high quality image.

<< Antioxidant added to the surface layer >>
In the present invention, it is preferable that the surface layer contains an antioxidant in order to sufficiently prevent fatigue deterioration of the electrophotographic performance of the photoreceptor in the process of repeated image formation, particularly a hindered amine, a hindered phenol compound, It preferably contains a phosphorus compound or a sulfur compound.

Examples of compounds which can be preferably used in the present invention, such as hindered amine compounds, hindered phenol compounds, phosphorus compounds and sulfur compounds, are shown below.

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<Structure of Intermediate Layer> Next, the photosensitive member of the present invention is used in order to ensure excellent image quality and adhesion when an image is formed by providing a photosensitive layer on a conductive support. It is characterized in that an intermediate layer containing an organometallic compound and / or a silane coupling agent is provided between the support and the photosensitive layer.

<< Organic Metal Compound, Silane Coupling >>
Examples of the organometallic compound contained in the intermediate layer of the photoreceptor of the present invention include alkoxide compounds such as zirconium tetra-n-propylate, aluminum isopropylate, mono-sec-butoxyaluminum-i-propylate, and aluminum-sec-butylate. And a group 1a, a group 1b, or a group 2a of the periodic table.
Group, group 3a, group 3b, group 4a, group 4b, group 5a
3, 4, 6, 8 with a metal atom selected from Group 5, 5b and Group 8 and acetoacetate, β-diketone, acetylacetone, catechol, ethylenediamine, o-phenylenebisdimethylaniline and the like as chelating agents
An organic metal chelate compound which is molecularly coordinated in the range of the molecule may be used.

However, in the intermediate layer of the photoreceptor of the present invention, the organometallic chelate compound represented by the general formula (2) is used as the organometallic compound, and together with the organometallic chelate compound, the intermediate formula (3) is used. It is preferred to contain the indicated silane coupling agents in combination.

In the general formula (2), R ¹ is a lower alkyl group, M represents a metal atom such as zirconium, titanium or aluminum, the chelating group K represents an acetoacetic ester group or a β-diketone residue, l and m represent an integer of 1 or more. However, when M is zirconium or titanium, l + m is 4, and when M is aluminum, l + m is 3.

Specific examples of the organometallic chelate compound represented by the general formula (2) include, for example, diisopropoxytitanium (methylacetoacetate) isobutoxytitanium tri (methylacetoacetate) tributoxytitanium acetylacetate Nitto diisopropoxyaluminum (methylacetoacetonate) dibutoxytitanium bis (ethylacetoacetonate) isobutoxyaluminum (acetylacetonate) and the like.

Next, in the silane coupling agent represented by the general formula (3), Q represents a halogen atom, a lower alkoxy group or an amino group which may have a substituent, and A represents a lower alkyl group or a phenyl group. Or an aryl group such as a naphthyl group, and the organic functional group Y is -BOOC (R ')
C = CH ₂ , —BNHR ″ or —BNH _2. R ′ represents a lower alkyl group, R ″ represents a lower alkyl group or an aryl group such as phenyl or naphthyl group, and B represents a lower alkylene group or —O. Represents a lower alkylene group containing-, -NH- and -CO-. p and q represent an integer of 1 or more, r represents an integer of 0 or more, and p + q + r is 4.

Specific examples of the silane coupling agent represented by the general formula (3) include, for example, γ-methacryloxypropyltrimethoxysilane γ-methacryloxypropyltriethoxysilane γ-methacryloxypropylmethyldimethoxysilane Etc. can be given.

In the present invention, the thickness of the intermediate layer is from 0.1 to
10 μm is preferable, and particularly preferably 0.1 to 5 μm.

<Layer Structure of Photoreceptor> The layer structure of the photoreceptor of the present invention comprises a charge generation material (CG) on a conductive support via an intermediate layer.
M) -containing charge generation layer (CGL), a charge transport layer (CTL) containing a charge transport substance (CTM), and a surface layer (as a protective layer) may be provided in this order, or via an intermediate layer. CGL containing CGM and surface layer (C
TL) may be provided in this order, or a surface layer (as a photosensitive layer) containing CGM may be provided via an intermediate layer. Further, CGM may be provided via an intermediate layer.
And a photosensitive layer and a surface layer (as a protective layer) containing both CTM and CTM may be provided in this order.

However, in the present invention, from the viewpoint of practicability, a configuration in which CGL containing CGM, CTL containing CTM, and a surface layer (as a protective layer) are provided in this order on a conductive support via an intermediate layer. Of particular importance.

The above-mentioned surface layer of the present invention has a CT
L may be used, but preferably, CTL
Alternatively, a protective layer may be provided on the CGL or single-layer type photosensitive layer as a separate layer. in this case,
More preferably, an adhesive layer is provided between the photosensitive layer and the surface layer of the invention.

<< CGM and CTM contained in the photosensitive layer >> Examples of the CGM contained in the photosensitive layer of the present invention include phthalocyanine pigments, polycyclic quinone pigments, azo pigments, perylene pigments, indigo pigments, quinacridone pigments, and azurenium pigments. And squarylium dyes, cyanine dyes, pyrylium dyes, thiopyrylium dyes, xanthene dyes, triphenylmethane dyes, styryl dyes, and the like. These CGMs can be used alone or together with a suitable binder resin to form a layer.

The CTM contained in the photosensitive layer includes:
For example, oxazole derivatives, oxadiazole derivatives,
Thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives,
Imidazoline derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds, benzidine compounds, pyrazoline derivatives, stilbene compounds, amine derivatives, oxazolone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, phenazine derivatives, amino Examples include stilbene derivatives, poly-N-vinylcarbazole, poly-1-vinylpyrene, poly-9-vinylanthracene, and the like. In these CTMs, a layer is usually formed together with a binder resin.

<< Binder Resin of Photosensitive Layer >> As the binder resin contained in the single-layered photosensitive layer and the CGL and CTL in the case of the laminated structure, polycarbonate resin, polyester resin, polystyrene resin, methacrylic resin,
Acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl butyral resin, polyvinyl acetate resin, styrene-butadiene resin, vinylidene chloride-acrylonitrile copolymer resin, vinyl chloride-maleic anhydride copolymer resin, urethane resin, silicon resin,
Epoxy resin, silicon-alkyd resin, phenol resin, polysilane resin, polyvinyl carbazole and the like can be mentioned.

In the present invention, the ratio of CGM to binder resin in CGL is preferably from 1: 5 to 5: 1 by weight. The thickness of the CGL is preferably 5 μm or less, particularly preferably 0.05 to 2 μm.

The CTL is formed by dissolving the CTM and the binder resin in an appropriate solvent, and applying and drying the solution. The mixing ratio of CTM and binder resin is preferably from 3: 1 to 1: 3 by weight.

The thickness of the CTL is preferably 5 to 50 μm, particularly preferably 10 to 40 μm. When a plurality of CTLs are provided, the thickness of the upper layer of the plurality of CTLs is preferably 10 μm or less. It is preferable that the thickness be smaller than the thickness of all the CTLs provided under the plurality of CTLs.

<< Solvent and Dispersant for Photosensitive Layer >> As the solvent or dispersant used for the photosensitive layer, intermediate layer and protective layer of the photoreceptor of the present invention, n-butylamine, diethylamine, ethylenediamine, isopropanolamine, tripropanolamine Ethanolamine, triethylenediamine, N, N-dimethylformamide, acetone, methyl ethyl ketone, methyl isopropyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, dichloromethane,
1,2-dichloroethane, 1,2-dichloropropane,
1,1,2-trichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethane,
Tetrahydrofuran, dioxolan, dioxane, methanol, ethanol, butanol, isopropanol,
Ethyl acetate, butyl acetate, dimethyl sulfoxide, methyl cellosolve and the like can be mentioned. Although the present invention is not limited to these, dichloromethane, 1,2-dichloroethane, methyl ethyl ketone and the like are preferably used. In addition, these solvents can be used alone or as a mixed solvent of two or more kinds.

<< Conductive Support >> Next, the conductive support of the electrophotographic photoreceptor of the present invention includes: 1) a metal plate such as an aluminum plate or a stainless plate, or 2) a support such as paper or a plastic film. ,
A thin metal layer such as aluminum, palladium, or gold provided by lamination or vapor deposition. 3) On a support such as paper or plastic film,
Examples thereof include those in which a layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is provided by coating or vapor deposition.

The material of the conductive support used in the present invention is mainly aluminum, copper, brass, steel,
A belt-shaped or drum-shaped metal material such as stainless steel or another plastic material is used. Among them, aluminum excellent in cost, workability and the like is preferably used, and a thin-walled cylindrical aluminum tube usually formed by extrusion or drawing is often used.

The shape of the support may be a drum shape, a sheet shape, or a belt shape, and is preferably a shape most suitable for the applied electrophotographic apparatus.

<< Coating Method >> Next, as a coating method for producing the electrophotographic photoreceptor of the present invention, coating methods such as dip coating, spray coating, and circular amount control type coating are used. The coating process on the surface layer side of the layer does not dissolve the lower layer film as much as possible, and in order to achieve a uniform coating process, a coating process such as a spray coating or a circular volume control type (a typical example is a circular slide hopper type). It is preferable to use The spray coating is described in detail in, for example, JP-A-3-90250 and JP-A-3-269238, and the circular amount control type coating is described in detail in, for example, JP-A-58-189061. I have.

In the present invention, a coating for compensating for surface defects of the support is provided between the support and the intermediate layer. A conductive layer for the purpose of preventing the generation can be provided. This conductive layer is made of carbon black,
It can be formed by applying and drying a solution in which conductive powder such as metal particles or metal oxide particles is dispersed in a suitable binder resin. The thickness of the conductive layer is preferably 5 to 40 μm, particularly preferably 10 to 30 μm.

<Image Forming Apparatus, Process Cartridge>
The photoreceptor of the present invention can be used for copying machines, laser printers, LEs
Although it can be applied to electrophotographic image forming apparatuses such as a D printer and a liquid crystal shutter printer in general,
Furthermore, the present invention can be widely applied to image forming apparatuses such as displays, recording, light printing, plate making, facsimile and the like to which electrophotographic technology is applied.

FIG. 1 is a sectional view of an image forming apparatus having the photoreceptor of the present invention.

In FIG. 1, reference numeral 10 denotes a photosensitive drum, which is a photosensitive drum having a photosensitive layer coated on the drum and a surface layer (protective layer) of the present invention provided thereon. Is done. Reference numeral 12 denotes a scorotron charger, which applies uniform charging to the peripheral surface of the photosensitive drum 10 by corona discharge. Prior to the charging by the charger 12, even if the peripheral surface of the photoconductor is removed by performing exposure by the exposure unit 11 using a light emitting diode (LED) or the like in order to eliminate the history of the photoconductor in the previous image formation. Good.

After the photosensitive member is uniformly charged, the image exposing device 13 performs image exposure based on the image signal. The image exposure device 13 in this figure uses a laser or LED (not shown) as an exposure light source. The light on the photosensitive drum is scanned by the light whose optical path is bent by the reflection mirror 132 through the rotating polygon mirror 131, the fθ lens, and the like, and an electrostatic latent image is formed.

Next, the electrostatic latent image is developed by the developing device 14. Developing devices 14 each having a built-in developer composed of toner and carrier such as yellow (Y), magenta (M), cyan (C), black (K), etc., at the periphery of the photosensitive drum 10.
First, development of the first color is performed by a developing sleeve 141 which rotates with a built-in magnet and holding a developer. The developer comprises, for example, a carrier in which an insulating resin is coated around a ferrite core, and a toner in which a pigment corresponding to a color and a charge control agent, silica, titanium oxide, etc. are added using polyester as a main material. The developer is regulated to a layer thickness of 100 to 600 μm on the developing sleeve 141 by a layer forming means (not shown), and is conveyed to a developing area to be developed. At this time, normally, a DC and / or AC bias voltage is applied between the photosensitive drum 10 and the developing sleeve 141 to perform the development.

In the color image formation, after the visualization of the first color is completed, the image forming process for the second color is started, and the uniform charging is again performed by the scorotron charger 12 to form the latent image of the second color. It is formed by the exposure device 13. An image forming process similar to that for the second color is performed for the third color and the fourth color, and a visible image of four colors is formed on the peripheral surface of the photosensitive drum 10. On the other hand, in a monochrome electrophotographic image forming apparatus, a developing device 1 is used.
Reference numeral 4 is composed of one kind of black toner and can form an image by one development.

After the image is formed, the recording paper P is fed to the transfer area by the rotation of the paper feed roller 17 at the time when the transfer timing is adjusted.

In the transfer area, a transfer roller (transfer device) 18 is pressed against the peripheral surface of the drum-shaped photoreceptor 10 in synchronization with the transfer timing, and the fed recording paper P is sandwiched to form a multicolor image. Are collectively transferred.

Next, the recording paper P is neutralized by the separator 19 which is brought into pressure contact with the transfer roller almost at the same time.
And heats and presses the heat roller 201 and the pressure roller 202 to fuse the toner.
Is discharged out of the apparatus via The transfer roller 18 and the separator 19 are retracted from the peripheral surface of the drum-shaped photoreceptor 10 after the recording paper P has passed to prepare for the formation of the next toner image.

On the other hand, the drum-shaped photoreceptor 10 from which the recording paper P has been separated, removes and cleans the residual toner by pressing the blade 221 of the cleaning device 22 and removes the charge by the exposure unit 11 and the charge by the charger 12 again. Then, the next image forming process is started. When a color image is formed on the photoconductor by superimposition, the blade 221 moves immediately after the cleaning of the photoconductor surface and is retracted from the peripheral surface of the drum-shaped photoconductor 10.

Reference numeral 30 denotes a detachable process cartridge in which a photosensitive member, a charging device, a transfer device / separator, and a cleaning device are integrated.

An electrophotographic image forming apparatus is constructed by integrally combining the above-mentioned drum-shaped photoreceptor and components such as a developing unit and a cleaning unit as a process cartridge. It may be configured to be detachable. Also, a process cartridge is formed by integrally supporting at least one of a charger, an image exposing unit, a developing unit, a transfer or separating unit, and a cleaning unit together with a photoreceptor. It may be configured to be detachable using a guide means such as a rail of the apparatus body.

When the image forming apparatus is used as a copying machine or a printer, the image exposure is performed by irradiating the photosensitive member with reflected light or transmitted light from the original, or by reading the original with a sensor and converting it into a signal. Scanning of a laser beam, driving of an LED array, or driving of a liquid crystal shutter array is performed by irradiating the photosensitive member with light.

When used as a facsimile printer, the image exposure unit 13 performs exposure for printing received data.

[0115]

EXAMPLES The present invention will be described below in detail with reference to examples, but embodiments of the present invention are not limited thereto.

Example 1 <Preparation of Photoconductor of Example 1><< Intermediate Layer >> Zirconium chelate compound “ZC-540” (manufactured by Matsumoto Pharmaceutical Co., Ltd.) 200 g Silane coupling agent “KBM-903” (manufactured by Shin-Etsu Chemical Co., Ltd.) 100 g methanol 700 ml ethanol 300 ml The above composition was applied onto a drum-shaped aluminum support by dip coating, and dried at 150 ° C. for 30 minutes to form an intermediate layer having a thickness of 1.0 μm.

<< CGL >> CGM (C1) having the following structure: 60 g 15% xylene-butanol solution of silicone resin “KR5240” (manufactured by Shin-Etsu Chemical Co., Ltd.) 700 g: methyl ethyl ketone 2000 ml The above compositions were mixed and dispersed using a sand mill for 10 hours. And a CGL coating solution. This coating solution was applied on the intermediate layer by a dip coating method to form a 0.2 μm-thick CGL.

<< CTL >> 200 g of CTM (D1) having the following structure: 300 g of bisphenol Z-type polycarbonate "Iupilon Z300" (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 300 g of 1,2-dichloroethane were mixed and dissolved to prepare a CTL coating solution. . This coating solution was applied on the CGL by a dip coating method,
μm CTLs were formed.

[0119]

Embedded image

However, in the X-ray diffraction diagram using the characteristic X-ray of CuKα, the Bragg angle (2θ ± 0.2 °) is 2
It has a maximum peak at 7.3 °, and 9.5 ° and 11.
Oxytitanium phthalocyanine having at least one peak at 6 °, 15.0 ° and 24.1 °.

[0121]

Embedded image

On top of this, a commercially available primer "PC-7J"
(Manufactured by Shin-Etsu Chemical Co., Ltd.) is diluted 2 times with toluene.
Drying was performed at 00 ° C. for 30 minutes to form an adhesive layer having a dry film thickness of 0.3 μm.

On top of this, 10 parts by weight of a polysiloxane resin (containing 1% by weight of silanol groups) consisting of 80% by mole of methylsiloxane units and 20% by mole of methyl-phenylsiloxane units was added to a commercially available dehydrating agent "Molecular sieve 4".
A "(manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was allowed to stand for 15 hours to be dehydrated. This resin was dissolved in 10 parts by weight of toluene, and 5 parts by weight of methyltrimethoxysilane and 0.2 parts by weight of dibutyltin acetate were added thereto to form a uniform solution.

6 parts by weight of a triarylamine-type charge transporting compound (exemplified compound T-1) was added thereto and mixed. The solution was applied as a surface layer (protective layer) having a dry film thickness of 1 μm, For 1 hour to produce the photoreceptor of Example 1.

Example 2 <Preparation of Photoreceptor of Example 2> In place of the triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer of the photoreceptor of Example 1, triarylamine type charge was used. A photoconductor of Example 2 was prepared in the same manner except that the transportable compound (exemplified compound T-14) was used.

Example 3 <Preparation of Photoreceptor of Example 3> Instead of the triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer of the photoreceptor of Example 1, a triarylamine type charge was used. A photoconductor of Example 3 was prepared in the same manner except that the transportable compound (exemplified compound T-15) was used.

For evaluation of the photoreceptors of Examples 1 to 3, the photoreceptors were mounted on a Konica 7050 (digital copying machine manufactured by Konica Corp.), and an image forming test was performed with the initial charging potential set at −650 V. That is, 20 ° C. 60% RH, 30 ° C. 80%
In the RH environment, the initial and 100,000 sheet image evaluations were performed using A4 paper. No fogging occurred in the initial and 100,000 sheets under both environmental conditions, and the density of the solid black portion was 1 in reflection density. .2 or more, and an image having excellent uniformity was obtained. Further, the abrasion loss of the photoreceptor at the end of 100,000 sheets was very small at 0.1 μm or less. Further, scars on the surface of the photoreceptor were scarcely observed, and no image defect due to scratches was observed on the halftone image. No peeling of the photosensitive layer was observed.

Comparative Example 1 <Preparation of Photoconductor of Comparative Example 1> The triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer in the photoconductor of Example 1 was replaced with 4- [2- ( [Triethoxysilyl) ethyl] The photoconductor of Comparative Example 1 was prepared in the same manner except that triphenylamine was used.

Evaluation of the photoreceptor of Comparative Example 1 was performed in the same manner as in the case of the photoreceptor of Example 1, and as a result, a good image was obtained in an environment of 20 ° C. and 60% RH, but 30 ° C. and 80% RH. In this case, fogging occurred in 70,000 images, and image blurring occurred in a part of the images.

Example 4 <Preparation of Photoreceptor of Example 4> A photoreceptor of Example 4 was prepared in the same manner as in Example 1 except that the intermediate layer was replaced with the following materials.

Silane Coupling Agent “KBM-903” (manufactured by Shin-Etsu Chemical Co., Ltd.) 300 g Water 30 ml Ethanol 1000 ml Further, the polysiloxane resin in the protective layer of the photoreceptor of Example 1 was prepared by adding 80 mol% of methylsiloxane units and dimethylsiloxane. Polysiloxane resin (20 mol%)
The photoreceptor of Example 4 was prepared in the same manner except that the photoreceptor was replaced with the same.

Comparative Example 2 <Preparation of Photoreceptor of Comparative Example 2> A photoreceptor of Comparative Example 2 was prepared in the same manner as in Example 1 except that the intermediate layer was replaced with the following materials.

Polyamide resin “CM-8000” manufactured by Toray Industries, Inc.) 15 g 2-propanol 150 ml methanol 850 ml Evaluation of the photoconductor of Comparative Example 2 was performed in the same manner as the photoconductor of Example 1, and as a result, the temperature was 20 ° C. and 60% RH. Although a good image was obtained in the environment of (3), at 30 ° C. and 80% RH, the reflection density of the black solid portion was reduced to 1.0 in 60,000 sheets of the image, and image blur occurred in a part of the image. In addition, peeling of the photosensitive layer was observed in part of the photosensitive layer after the completion of 100,000 sheets.

Example 5 <Preparation of Photoreceptor of Example 5> The polysiloxane resin of the protective layer of the photoreceptor of Example 1 was prepared by adding 30 mol% of a methylsiloxane unit, 40 mol% of an ethylsiloxane unit, and 20 mol of a dimethylsiloxane unit. %, A polysiloxane resin consisting of 10 mol% of diethylsiloxane units (containing 2% by weight of silanol groups) was prepared in the same manner as in Example 5, except that a polysiloxane resin was used.

Example 6 <Preparation of Photoreceptor of Example 6> The polysiloxane resin of the protective layer of the photoreceptor of Example 1 was prepared by adding 30 mol% of methylsiloxane units, 30 mol% of phenylsiloxane units, and 20 mol of dimethylsiloxane units. %, Diethylsiloxane unit 20
A photoreceptor of Example 6 was made in the same manner except that the polysiloxane resin consisting of mol% (containing 2% by weight of silanol group) was used.

Example 7 <Preparation of Photoreceptor of Example 7> The triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer of the photoreceptor of Example 1 was replaced with a hydrazone type charge transporting compound ( A photoconductor of Example 7 was made in the same manner except that the exemplified compound H-1) was replaced.

Example 8 <Preparation of Photoreceptor of Example 8> The triarylamine type charge transporting compound (Exemplified Compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a hydrazone type charge transporting compound ( A photoconductor of Example 8 was prepared in the same manner except that the exemplified compound H-5) was replaced.

Example 9 <Preparation of Photoreceptor of Example 9> The triarylamine type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a stilbene type charge transporting compound ( A photoconductor of Example 9 was made in the same manner except that the exemplified compound S-1) was replaced.

Example 10 <Preparation of Photoreceptor of Example 10> The triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer of the photoreceptor of Example 1 was replaced with a stilbene type charge transporting compound ( A photoconductor of Example 10 was made in the same manner except that Exemplified Compound S-4) was used.

Example 11 <Preparation of Photoreceptor of Example 11> The triarylamine type charge transporting compound (exemplified compound T-1) in the protective layer of the photoreceptor of Example 1 was replaced with a stilbene type charge transporting compound ( A photoconductor of Example 11 was made in the same manner except that Exemplified Compound S-8) was used.

Example 12 <Preparation of Photoreceptor of Example 12> The triarylamine type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a benzidine type charge transporting compound (Example Compound T-1). A photoconductor of Example 12 was made in the same manner except that the exemplified compound Be-1) was replaced.

Example 13 <Preparation of Photoreceptor of Example 13> The triarylamine type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a benzidine type charge transporting compound ( A photoconductor of Example 13 was made in the same manner except that Exemplified Compound Be-4) was used.

Example 14 <Preparation of Photoreceptor of Example 14> The triarylamine type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a benzidine type charge transporting compound ( A photoconductor of Example 14 was made in the same manner except that Exemplified Compound Be-6) was used.

Example 15 <Preparation of Photoreceptor of Example 15> The triarylamine type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 was replaced with a butadiene type charge transporting compound (Example Compound T-1). A photoreceptor of Example 15 was made in the same manner except that Exemplified Compound Bu-1) was used.

Example 16 <Preparation of Photoreceptor of Example 16> The triarylamine-type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 is exemplified by other charge transporting compounds. A photoconductor of Example 16 was made in the same manner except that the compound (So-1) was used.

Example 17 <Preparation of Photoreceptor of Example 17> The triarylamine-type charge transporting compound (exemplified compound T-1) of the protective layer of the photoreceptor of Example 1 is exemplified by other charge transporting compounds. A photoconductor of Example 17 was made in the same manner except that the compound (So-3) was used.

Example 18 <Preparation of Photoreceptor of Example 18> Instead of the intermediate layer of the photoreceptor of Example 1, a coating solution obtained by stirring and mixing the following composition was dip-coated on a support. After drying at 150 ° C. for 30 minutes, an intermediate layer having a thickness of 1.0 μm was formed, and the same CGL, CTL and adhesive layer as in Example 1 were formed on the intermediate layer.

Titanium chelate compound “TC-750” (Matsumoto Pharmaceutical Co., Ltd.) 200 g Silane coupling agent “KBM-503” (Shin-Etsu Chemical Co., Ltd.) 130 g 2-propanol 1000 ml Water 30 ml 60 parts by weight of a curable siloxane resin “KP-854” (manufactured by Shin-Etsu Chemical Co., Ltd.) and 60 parts by weight of isopropanol were added and uniformly dissolved, and a triarylamine-type charge transporting compound (exemplified compound T) was obtained in the same manner as in Example 1. -1) A coating solution obtained by mixing 6 parts by weight was applied and dried at 120 ° C. for 1 hour to form a protective layer having a dry film thickness of 1 μm, thereby producing a photoreceptor of Example 18.

Example 19 <Preparation of Photoconductor of Example 19> A siloxane resin “X-40-2239” (manufactured by Shin-Etsu Chemical Co., Ltd.) was used in place of the siloxane resin “KP-854” for the protective layer of Example 18. A photoreceptor of Example 19 was made in exactly the same manner except that

Example 20 A coating solution obtained by stirring and mixing the following composition in place of the intermediate layer of Example 18 was dip-coated on a support, dried at 150 ° C. for 30 minutes, and dried to a thickness of 1.0 μm. A layer was formed, and the same CGL, CTL and adhesive layer as in Example 1 were formed on the intermediate layer.

Titanium chelate compound “TC-100” (manufactured by Matsumoto Pharmaceutical Co., Ltd.) 200 g Silane coupling agent “KBM-903” (manufactured by Shin-Etsu Chemical Co., Ltd.) 130 g Toluene 1000 ml Water 30 ml Instead of the siloxane resin "KP-854", the siloxane resin "X-40"
A protective layer was formed in exactly the same manner as in Example 20, except that "-2269" (Shin-Etsu Chemical Co., Ltd.) was used.

The evaluation of the photosensitive members of Examples 4 to 20 was performed in Example 1.
At a temperature of 20 ° C. and 60% R
H, 30 ° C., 80% RH environment, no fog occurs in both initial and 100,000 sheets under both environmental conditions, and the density of the solid black portion is a reflection density of 1.2 or more, and uniformity is obtained. Excellent image was obtained. Further, the abrasion loss of the photoreceptor at the end of 100,000 sheets was very small at 0.1 μm or less. Further, scars on the surface of the photoreceptor were scarcely observed, and no image defect due to scratches was observed on the halftone image. No peeling of the photosensitive layer was observed.

Example 21 A photoreceptor of Example 21 was prepared in the same manner as in Example 1, except that 0.9 parts by weight of a hindered phenol compound (Exemplified Compound 1-32) was added to the protective layer.

Example 22 A photoreceptor of Example 22 was prepared in the same manner except that 0.6 parts by weight of a hindered phenolamine compound (Exemplified Compound 2-1) was added to the protective layer of the photoreceptor of Example 1. did.

The photosensitive members of Examples 21 and 22 were evaluated in the same manner as the photosensitive member of Example 1.

No fogging occurred in the initial and 100,000 sheets under both environmental conditions of 20 ° C., 60% RH and 30 ° C., 80% RH, and the density of the solid black portion was 1.3 in reflection density.
The above density was obtained, and an image having excellent uniformity was obtained.
Further, the abrasion loss of the photoreceptor at the end of 100,000 sheets was very small at 0.1 μm or less. Further, scars on the surface of the photoreceptor were scarcely observed, and no image defect due to scratches was observed on the halftone image. No peeling of the photosensitive layer was observed. In the photoconductors of Examples 21 and 22, since an antioxidant was contained in the protective layer, the photoconductors of Examples 21 and 22 had higher concentrations than the photoconductors of Examples 1 to 20 not containing the antioxidant. A clear image was obtained.

From Examples 1 to 22 and Comparative Examples 1 and 2,
The photoreceptor of Example has a small thickness wear amount of the photoreceptor even when repeatedly forming an image up to 100,000 times under high temperature and high humidity, and has no fog, image blur, film peeling, scratches, etc.
Although a high-density and clear image can be obtained, it is understood that any of the photoconductors of the comparative examples is inferior and is not practical.

[0158]

As demonstrated by the examples, according to the photoreceptor of the present invention, the process cartridge and the image forming apparatus using the same, the hardness of the surface of the photosensitive layer is high, and the abrasion resistance, scratch resistance and adhesion are improved. The electrophotographic performance is excellent, and even when the image is repeatedly formed, especially when the image is repeatedly formed under a high temperature and a high humidity, the electrophotographic performance is not deteriorated by fatigue, and fog and image blur are generated. And excellent effects such as stably obtaining good images.

[Brief description of the drawings]

FIG. 1 is a sectional view of an image forming apparatus.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 10 Photoreceptor drum 12 Charger 13 Image exposure device 14 Developing device 18 Transfer roller 19 Separator 20 Fixing device 22 Cleaning device 30 Process cartridge

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yoko Kitahara 2970 Ishikawacho, Hachioji-shi, Tokyo Konica Corporation (72) Inventor Masahiko Kurachi 2970 Ishikawacho, Hachioji-shi, Tokyo Konica Corporation (72) Inventor Kazuhisa Shida 2970 Ishikawacho, Hachioji-shi, Tokyo Konica Corporation F-term (reference) 2H068 AA04 AA43 AA44 BA12 BA57 BA58 BB32 BB44 BB57 FA03 FA27

Claims (9)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer on a conductive support via an intermediate layer, wherein the surface layer of the electrophotographic photosensitive member includes a structural unit represented by the following general formula (1). An electrophotographic photoreceptor comprising a layer containing a siloxane-based cured resin, wherein the intermediate layer is a layer containing an organometallic compound and / or a silane coupling agent. Embedded image (In the formula, X is a charge transporting ability-imparting group, and is a group bonded to Z in the formula via a carbon atom constituting the imparting group;
Z is a divalent or higher valent atom or group other than adjacent bonding atoms (Si and C). ) 2. In the general formula (1), X is a charge-transporting group, and is a group bonded to Z in the formula via a carbon atom constituting the group, and Z is an oxygen atom. The electrophotographic photosensitive member according to claim 1, wherein (O), a sulfur atom (S) or an NR group, and R is a hydrogen atom or a monovalent organic group. 3. The electrophotographic photosensitive member according to claim 1, wherein the organometallic compound contained in the intermediate layer is a metal alkoxide or an organometallic chelate. 4. The electrophotographic photoconductor according to claim 1, wherein the intermediate layer is a layer containing an organic metal chelate and a silane coupling agent. 5. The electrophotographic photoreceptor according to claim 3, wherein the organic metal chelate contained in the intermediate layer is represented by the following general formula (2). Formula (2) (R ¹ O) _l -M- (K) _m (wherein R ¹ is an alkyl group, M is zirconium,
A chelating group K representing titanium or aluminum
Represents an acetoacetic ester group or a β-diketone residue,
l and m represent an integer of 1 or more. However, when M is zirconium or titanium, l + m is 4, and when M is aluminum, l + m is 3. ) 6. The electrophotographic photoconductor according to claim 1, wherein the silane coupling agent contained in the intermediate layer is represented by the following general formula (3). Formula (3) (Q) _p -Si (Y) _q- (A) _r (wherein Q represents a halogen atom, an alkoxy group or an amino group, A represents an alkyl group or an aryl group, and the organic functional group Y Represents —BOOC (R ′) C ＝ CH ₂ , —BNHR ″ or —BNH _2. R ′ represents an alkyl group, R ″ represents an alkyl group or an aryl group, B represents an alkylene group or —O—, Represents an alkylene group containing -NH-, -CO-, p and q represent an integer of 1 or more, r represents an integer of 0 or more, and p + q + r is 4.) 7. The electrophotographic photoreceptor according to claim 1, wherein the surface layer contains a hindered amine or a hindered phenol compound. 8. An image forming method using the electrophotographic photosensitive member according to claim 1, wherein the image forming is performed through charging, image exposure, development, transfer, separation and cleaning. apparatus. 9. A combination of the electrophotographic photosensitive member according to claim 1 and at least one of a charger, an image exposing unit, a developing unit, a transfer unit, a separator and a cleaning unit. A process cartridge characterized by being manufactured.