JP2000310870A - Electrophotographic photoreceptor, electrophotographic image forming method using same, electrophotographic image forming device and process cartridge - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enhance surface hardness, wear and scuffing resistances and to ensure such electrophotographic characteristics in repetitive use as to repeatedly give a good image even at high temperature and high humidity. SOLUTION: An electric charge generating layer, an electric charge transferring layer and a resin layer are successively laminated on an electrically conductive substrate to obtain the objective electrophotographic photoreceptor. The resin layer contains a siloxane resin having a structural unit with electric charge transferring performance and also having a crosslinked structure. The thickness of the electric charge transferring layer is >=12 μm, the thickness of the resin layer is <=2.5 μm and the ratio of the thickness of the resin layer to the thickness of the electric charge transferring layer is 0.01 to <0.25.

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 (hereinafter, also simply referred to as a photosensitive member), an electrophotographic image forming method using the photosensitive member, an electrophotographic image forming apparatus, and a process cartridge. .

[0002]

2. Description of the Related Art In recent years, an organic photoconductor containing an organic photoconductive substance has been most widely used as an electrophotographic photoconductor. Organic photoreceptors are advantageous over other photoreceptors in that materials that can be used for various exposure light sources from visible light to infrared light can be easily developed, materials that do not pollute the environment can be selected, and manufacturing costs are low. However, the only disadvantage is that the mechanical strength is weak,
The problem is that the photoreceptor surface is deteriorated or scratched when copying or printing a large number of sheets.

In general, in the electrophotographic image forming method of the Carlson method, a photoreceptor is uniformly charged, and then charge is erased imagewise by exposure to form an electrostatic latent image, and the electrostatic latent image is formed. Is developed and visualized with toner, and then the toner is transferred and fixed on paper or the like.

However, not all of the toner on the photoreceptor is transferred, and some of the toner remains on the photoreceptor. When an image is repeatedly formed in this state, the formation of a latent image is disturbed by the influence of the residual toner. Therefore, it is not possible to obtain a high-quality copy without contamination. Therefore, it is necessary to remove the residual toner. The cleaning means is typically a fur brush, a magnetic brush, a blade, or the like, but a blade is mainly used in terms of performance, configuration, and the like. At this time, a plate-shaped rubber elastic body is generally used as the blade member.

As described above, since the surface of the electrophotographic photosensitive member is directly subjected to an electrical or mechanical external force by a charger, a developing device, a transfer means, a cleaning device, etc., the surface thereof is required to have durability. In particular, it is required to have mechanical durability against abrasion and scratches on the surface of the photoreceptor due to rubbing, film intrusion of foreign matter, and film peeling due to impact during paper jam processing. 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.

In order to satisfy the various characteristics required as described above, various things have been studied so far.

For example, regarding mechanical durability, it has been reported that by using BPZ polycarbonate as a binder (binder resin) on the surface of an organic photoreceptor, the abrasion characteristics and toner filming characteristics of the surface are improved. I have. Japanese Patent Application Laid-Open No. Hei 6-118681 reports that a curable silicone resin containing colloidal silica is used as a surface layer of a photoreceptor.

However, a photoreceptor using a bisphenol Z-type polycarbonate binder still lacks abrasion resistance and does not have sufficient durability. On the other hand, in the surface layer of the curable silicone resin containing colloidal silica, the abrasion resistance is improved, but the electrophotographic properties after repeated use are insufficient, and fogging and image blur are liable to occur. Not enough.

[0009] The inventors of the present invention have found that the potential characteristics in a low-humidity environment can be improved by using a siloxane-based resin having a charge-transporting performance-imparting group and a cross-linked structure as a surface layer of a photoreceptor. (Japanese Patent Application No. 11-70)
No. 380).

However, when a siloxane-based resin having a charge-transporting performance-imparting group and a cross-linking structure is used for the surface layer, the difference in mechanical properties from the adjacent lower layer affects the adhesion and the film strength. Being more accessible has been raised as a new issue. Especially when the lower layer is a charge transport layer,
If the thickness of the charge transport layer is too small and the thickness of the surface layer is too large, it is difficult to obtain sufficient film strength.

On the other hand, an electrophotographic photoreceptor having a siloxane-based resin having a charge transporting performance-imparting group and having a cross-linking structure in a surface layer thereof may cause fogging under high temperature and high humidity conditions (hereinafter also referred to as HH conditions). Image blur tends to occur. One means for improving this is to include an antioxidant in the surface layer. However, when a hindered phenol-based or hindered amine-based antioxidant is used as the antioxidant, the thickness of the surface layer is reduced. It has been found that increasing the thickness of the film particularly deteriorates the strength properties of the film.

[0012]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems by providing a high surface hardness, a high abrasion resistance and a high scratch resistance, and an electrophotographic characteristic upon repeated use at high temperature and high humidity. Provided is an electrophotographic photoreceptor which is stable even under the image, and thus can repeatedly obtain good images. Also, the present invention provides an electrophotographic image forming method, an electrophotographic image forming apparatus, and a process cartridge using the photoreceptor. Is to do.

[0013]

The inventors of the present invention have made intensive efforts to solve the above problems, and as a result, the electrophotographic photosensitive member has a specific resin layer, and the resin layer and a charge transport layer thereunder. It has been found that there is a specific relationship between the film thicknesses and that a satisfactory film strength can be obtained by satisfying the relationship, and that a good image can be obtained even under a high temperature and high humidity environment.

That is, it has been found that the object of the present invention can be achieved by adopting any one of the following constitutions.

1. In an electrophotographic photosensitive member in which a charge generation layer, a charge transport layer, and a resin layer are sequentially laminated on a conductive support, the resin layer has a structural unit having charge transport performance,
And a layer containing a siloxane-based resin having a crosslinked structure, wherein the charge transport layer is 12 μm or more, and the resin layer is 2.
An electrophotographic photosensitive member having a thickness of 5 μm or less and a film thickness ratio between the resin layer and the charge transport layer falling within the range of the following formula.

1. 0.01 ≦ thickness of resin layer / thickness of charge transport layer <0.25 2. The electrophotographic photoreceptor according to the above item 1, wherein the resin layer further contains a hindered phenol-based or hindered amine-based antioxidant.

3. 3. The electrophotographic photoreceptor according to the above item 1 or 2, wherein the content of the charge transporting agent in the charge transporting layer is 45% by weight or more.

4. The siloxane-based resin having a structural unit having charge transport performance and having a crosslinked structure is a resin obtained by reacting an organosilicon compound having a hydroxyl group or a hydrolyzable group with a charge transportable compound having a hydroxyl group. 4. The electrophotographic photosensitive member according to any one of the above items 1 to 3, wherein

5. A resin obtained by reacting an organosilicon compound having a hydroxyl group or a hydrolyzable group with a charge transporting compound having a silicon atom-containing group, wherein the siloxane-based resin having the structural unit having the charge transporting ability and having a cross-linked structure is reacted. 4. The electrophotographic photoreceptor according to any one of the above items 1 to 3, wherein

6. 6. The electrophotographic photoreceptor according to any one of items 1 to 5, wherein the charge transport layer has a thickness of 21 μm or more.

7. 6. The electrophotographic photoreceptor according to any one of items 1 to 5, wherein the charge transport layer has a thickness of 26 μm or more.

8. 8. The electrophotographic photosensitive member according to any one of items 1 to 7, wherein the conductive support is a cylindrical drum having a diameter of 35 mm or more.

9. 9. The electrophotographic image forming method according to claim 1, wherein the electrophotographic photosensitive member has at least steps of charging, exposing, developing, and cleaning the electrophotographic photosensitive member. An electrophotographic image forming method using a photoreceptor.

10. In an electrophotographic image forming apparatus having an electrophotographic photoreceptor and at least charging, image exposure, development, and cleaning means,
An electrophotographic image forming apparatus, wherein the electrophotographic photoreceptor according to any one of the above items 8 is used.

[11] Electrophotographic photoreceptor and at least charged,
The process cartridge used in the electrophotographic image forming apparatus having image exposure, development, and cleaning means is the aforementioned 1
An electrophotographic photoreceptor and a charger according to any one of items 1 to 8,
A process cartridge having an image exposing device, a developing device, and a cleaning device in an integrated manner, and being designed to be freely inserted into and removed from the electrophotographic image forming apparatus.

The present invention will be described in more detail.

In the present invention, the siloxane-based resin in the siloxane-based resin having a structural unit having a charge-transporting property and having a cross-linked structure can be prepared by a known method, that is, by converting an organosilicon compound having a hydroxyl group or a hydrolyzable group. It is manufactured using. The organosilicon compound has the following general formula (A)
To (D).

[0028]

Embedded image

(Wherein, R _{1 to} R ₆ represent an organic group in which carbon is directly bonded to silicon in the formula, and Z represents a hydroxyl group or a hydrolyzable group.) In the case of a decomposable group, examples of the hydrolyzable group include a methoxy group, an ethoxy group, a methylethylketoxime group, a diethylamino group, an acetoxy group, a propenoxy group, a propoxy group, a butoxy group and a methoxyethoxy group. Examples of the organic group in which carbon is directly bonded to silicon represented by R _{1 to} R ₆ include alkyl groups such as methyl, ethyl, propyl and butyl, aryl groups such as phenyl, tolyl, naphthyl and biphenyl, and γ-glycidyl. Epoxy-containing groups such as xypropyl, β- (3,4-epoxycyclohexyl) ethyl, γ-acryloxypropyl, γ
-A (meth) acryloyl group containing methacryloxypropyl, a hydrate group such as γ-hydroxypropyl and 2,3 dihydroxypropyloxypropyl, a vinyl group containing vinyl and propenyl, a mercapto group containing γ-mercaptopropyl and the like, Amino-containing groups such as γ-aminopropyl, N-β (aminoethyl) -γ-aminopropyl, and γ-chloropropyl, 1,1,1-trifluorofluoropropyl, nonafluorohexyl, perfluorooctylethyl, etc. Examples include a halogen group, other nitro and cyano-substituted alkyl groups, and the like. Further, R _{1 to} R ₆ may have the same or different organic groups.

In general, when the number n of hydrolyzable groups bonded to silicon atoms of the organosilicon compound used as a raw material of the siloxane-based resin is 1, the polymerization reaction of the organosilicon compound is suppressed. You. n is 2, 3 or 4
In the case of (3), the polymerization reaction is likely to occur.
It is possible to advance the crosslinking reaction to a high degree. Therefore, by controlling these, it is possible to control the preservability of the obtained coating layer liquid, the hardness of the coating layer, and the like.

As a raw material of the siloxane-based resin, a hydrolyzed condensate obtained by hydrolyzing the organosilicon compound under acidic or basic conditions to oligomerize or polymerize can be used.

As described above, the siloxane-based resin of the present invention is obtained by reacting a monomer, oligomer, or polymer having a siloxane bond in a chemical structural unit in advance (hydrolysis reaction, reaction in which a catalyst or a crosslinking agent is added, etc.). (Included) means a resin that has formed and cured a three-dimensional network structure. That is, it means a siloxane-based resin having a cross-linked structure formed by promoting a siloxane bond by a hydrolysis reaction and subsequent dehydration condensation of an organosilicon compound having a siloxane bond to form a three-dimensional network structure.

Further, the siloxane-based resin may contain colloidal silica having a hydroxyl group or a hydrolyzable group, and may be a resin having silica particles incorporated in a part of a crosslinked structure.

The siloxane-based resin having a structural unit having a charge transporting property and having a crosslinked structure according to the present invention is a chemical structure having a characteristic of exhibiting electron or hole drift mobility (= a structure having a charge transporting property). (Also referred to as a unit or a charge transport performance-imparting group) in a siloxane-based resin as a partial structure. Specifically, the siloxane-based resin having a structural unit having a charge transporting property of the present invention and having a crosslinked structure includes a compound generally used as a charge transporting substance (hereinafter, also referred to as a charge transporting compound or CTM). It has a partial structure in the siloxane-based resin.

The above-mentioned structural unit having charge transport performance (= charge transport performance imparting group) is a structural unit having the property of having electron or hole drift mobility or a charge transport compound residue, Another definition is Time-O
It can also be expressed as a structural unit or a charge transporting compound residue from which a detection current due to charge transport can be obtained by a known method capable of detecting charge transport performance such as the f-Flight method.

The charge transporting compound capable of forming a charge transporting performance-imparting group in a siloxane-based resin by reaction with an organic silicon compound will be described below.

For example, hole transport type CTM: xazole, oxadiazole, thiazole, triazole, imidazole, imidazolone, imidazoline, bisimidazolidine, styryl, hydrazone, benzidine, pyrazoline,
Stilbene compound, amine, oxazolone, benzothiazole, benzimidazole, quinazoline, benzofuran, acridine, phenazine, aminostilbene, poly-N-vinylcarbazole, poly-1-vinylpyrene,
A chemical structure such as poly-9-vinylanthracene is contained as a partial structure of the siloxane-based resin.

On the other hand, electron transport type CTMs include succinic anhydride, maleic anhydride, phthalic anhydride, pyromellitic anhydride, melitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, nitrobenzene, dinitrobenzene, trinitrobenzene, Tetranitrobenzene, nitrobenzonitrile, picryl chloride, quinone chlorimide, chloranil, bromanyl, benzoquinone, naphthoquinone, diphenoquinone, tropoquinone, anthraquinone, 1-chloroanthraquinone, dinitroanthraquinone, 4-nitrobenzophenone, 4,4'-dinitrobenzophenone, 4-nitrobenzalmalonedinitrile, 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-fluoronylidenedicyanomethylenemalonodinitrile, picric acid, o-nitrobenzoic acid, p-nitrobenzoic acid, 3, Chemical structures such as 5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, phthalic acid and melitic acid are contained as partial structures of the siloxane-based resin.

In the present invention, a preferable charge transporting performance-imparting group is a residue of a commonly used charge transporting compound as described above, and is represented by the following formula via a carbon atom or a silicon atom constituting the charge transporting compound. And is contained in the siloxane-based resin via Y.

[0040]

Embedded image

(In the formula, X is a charge transporting performance-imparting group, a group bonding to Y in the formula via a carbon atom or a silicon atom constituting the imparting group, and Y is an adjacent bonding atom (Si and A divalent or higher valence atom or group excluding C). However, when Y is a trivalent or higher valence atom, the bond between Si and Y other than C in the formula can be bonded to the curable resin. Has a structure (group) bonded to any of the constituent atoms described above or connected to another atom or molecular group.

In the above formula, an oxygen atom (O), a sulfur atom (S), and a nitrogen atom (N) are particularly preferable as the Y atom.

Here, when Y is a nitrogen atom (N), the linking group is represented by -NR-. (R is a hydrogen atom or a monovalent organic group.) The charge transporting performance-imparting group X is shown as a monovalent group in the formula, but two or more charge transporting compounds are reacted with the siloxane-based resin. When it has a reactive functional group, it may be bonded as a divalent or higher crosslink group in the curable resin, or may be bonded simply as a pendant group.

The above-mentioned atoms, ie, the atoms of O, S, and N, are formed by the reaction of a hydroxyl group, a mercapto group, or an amine group introduced into a compound having a charge transporting ability with an organic silicon compound having a hydroxyl group or a hydrolyzable group. It is a linking group that is formed and incorporates the charge transport performance-imparting group into the siloxane-based resin as a partial structure.

Next, the charge transporting compound having a hydroxyl group, a mercapto group, an amine group and an organic silicon-containing group in the present invention will be described.

The charge transporting compound having a hydroxyl group is
It is a charge transport substance having a commonly used structure and a compound having a hydroxyl group. That is, typically, a charge transporting compound represented by the following general formula that can form a resin layer by bonding to a curable organosilicon compound can be exemplified, but is not limited to the following structure. Any compound having a charge transporting ability and a hydroxyl group may be used.

X- (R ₇ -OH) m m ≧ 1 wherein X: a group for imparting charge transport performance, R ₇ : a single bond, a substituted or unsubstituted alkylene group, an arylene group, m: an integer of 1 to 5 It is.

Among them, the following are typical examples. For example, a triarylamine-based compound has a triarylamine structure such as triphenylamine as a charge transport performance-imparting group = X, and an alkylene extended through a carbon atom constituting X or extended from X;
A compound having a hydroxyl group via an arylene group is preferably used.

1. Triarylamine compounds

[0050]

Embedded image

2. Hydrazine compounds

[0052]

Embedded image

3. Stilbene compounds

[0054]

Embedded image

4. Benzidine compound

[0056]

Embedded image

5. Butadiene compound

[0058]

Embedded image

6. Other compounds

[0060]

Embedded image

Next, a synthesis example of a charge transporting compound having a hydroxyl group will be described.

Synthesis of Exemplified Compound T-1

[0063]

Embedded image

Step A In a four-headed kolben equipped with a thermometer, a condenser, a stirrer, and a dropping funnel, 49 g of the compound (1) and phosphorus 184 chloride were added.
g was added and dissolved by heating. 117 g of dimethylformamide was gradually added dropwise from the dropping funnel.
The mixture was kept at ９５95 ° C. and stirred for about 15 hours. Next, the reaction solution was gradually poured into a large excess of warm water, and then slowly cooled with stirring.

The precipitated crystals were filtered and dried, and then purified by adsorption of impurities with silica gel or the like and recrystallization with acetonitrile to obtain a compound (2). Yield 30
g.

Step B 30 g of compound (2) and 100 ml of ethanol were charged into a kolben and stirred. After gradually adding 1.9 g of sodium borohydride, the solution was kept at 40 to 60 ° C. and stirred for about 2 hours. Next, the reaction solution was gradually poured into about 300 ml of water and stirred to precipitate crystals. After filtration, the resultant was sufficiently washed with water and dried to obtain a compound (3). The yield was 30 g.

Synthesis of Exemplified Compound S-1

[0068]

Embedded image

Step A In a 300 ml Kolben equipped with a thermometer and a stirrer, add C
u, 30 g, K2CO3, 60 g, compound (1) 8 g,
100 g of the compound (2) was charged, the temperature was raised to about 180 ° C., and the mixture was stirred for 20 hours. After cooling, the mixture was filtered and purified by column to obtain 7 g of compound (3).

Step B A 100 ml kolben equipped with a thermometer, a dropping funnel, an argon gas introducing device and a stirrer was set to an argon gas atmosphere, and 7 g of the compound (3), 50 ml of toluene and 3 g of phosphoryl chloride were charged into the atmosphere. While stirring at room temperature, D
2 g of MF was slowly added dropwise, and then the temperature was raised to about 80 ° C. and the mixture was stirred for 16 hours. The mixture was poured into warm water of about 70 ° C. and cooled. This was extracted with toluene, and the extract was washed with water until the pH of the water reached 7. After drying over sodium sulfate, the mixture was concentrated and purified by column to obtain 5 g of compound (4).

Step C: 100 ml with an argon gas introducing device and a stirring device
1.0 g of t-BuOK and 60 ml of DMF were charged into the Kolben, and the atmosphere was changed to an argon gas atmosphere. Compound (4)
2.0 g and 2.2 g of the compound (5) were added, and the mixture was stirred at room temperature for 1 hour. This was poured into a large excess of water, extracted with toluene, the extract was washed with water, dried over sodium sulfate,
After concentration, column purification was performed, and 2.44 g of compound (6) was obtained.
I got

Step D Toluene was charged into a 100 ml kolben equipped with a thermometer, a dropping funnel, an argon gas introducing device and a stirring device, and the atmosphere was changed to an argon gas atmosphere. To this, 15 ml of a hexane solution of n-BuLi (1.72 M) was added, and the mixture was heated to 50 ° C. To this, 2.44 g of compound (6) was added in 30 ml of toluene.
The dissolved liquid was added dropwise, and the mixture was stirred at 50 ° C. for 3 hours. After cooling to −40 ° C., 8 ml of ethylene oxide was added, the temperature was raised to −15 ° C., and the mixture was stirred for 1 hour.
Thereafter, the temperature was raised to room temperature, 5 ml of water was added, and ether 2 was added.
After extraction with 00 ml, the extract was washed with saturated saline.
After washing the washing solution to pH, it was dried over sodium sulfate, concentrated and purified by column to obtain 1.0 g of compound (7).

Next, specific examples of the charge transporting compound having a mercapto group are shown below.

The charge transporting compound having a mercapto group is a charge transporting substance having a commonly used structure and a compound having a mercapto group. That is, typically, a charge transporting compound represented by the following general formula that can form a resin layer by bonding to a curable organosilicon compound can be exemplified, but is not limited to the following structure. Any compound may be used as long as it has a charge transporting ability and a mercapto group.

X- (R ₈ -SH) m m ≧ 1 wherein X: a group for imparting charge transport performance, R ₈ : a single bond, a substituted or unsubstituted alkylene or arylene group, m: an integer of 1 to 5 is there.

Among them, the following are typical ones.

[0077]

Embedded image

Further, the charge transporting compound having an amino group will be described.

The charge transporting compound having an amino group is a charge transporting substance having a commonly used structure and a compound having an amino group. That is, typically, a charge transporting compound represented by the following general formula that can form a resin layer by bonding to a curable organosilicon compound can be exemplified, but is not limited to the following structure. Any compound having a charge transporting ability and having an amino group may be used.

X- (R ₉ -NR ₁₀ H) m m ≧ 1 wherein X is a group for imparting charge transport performance, R _{9 is a} single bond, substituted or unsubstituted alkylene, substituted or unsubstituted arylene group, R ₁₀ : hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, m: an integer of 1 to 5.

Among them, the following are typical ones.

[0082]

Embedded image

Among the charge transporting compounds having an amino group, in the case of a primary amine compound (—NH ₂ ), two hydrogen atoms may react with an organosilicon compound and be linked to a siloxane structure. In the case of a secondary amine compound (—NHR ₁₀ ), one hydrogen atom reacts with the organosilicon compound, and R ₁₀ may be a group that remains as a branch or a group that causes a cross-linking reaction, and includes a charge transport material. It may be a compound residue.

Further, the charge transporting compound having a silicon atom-containing group will be described.

The charge transporting compound having a silicon atom-containing group is a charge transporting substance having the following structure. This compound can also combine with the curable organosilicon compound to form a resin layer.

X-(— Y—Si (R ₁₁ ) _3-a (R ₁₂ ) _a ) _n (wherein X is a group containing a structural unit having charge transport performance, R ₁₁ is a hydrogen atom, R ₁₂ represents a hydrolyzable group or a hydroxyl group, Y represents a substituted or unsubstituted alkylene group or an arylene group, a represents an integer of 1 to 3, and n represents Represents an integer.) Among them, there are the following as typical examples.

Raw material for forming the siloxane-based resin: The composition ratio of the above-mentioned general formulas (A) to (D) (hereinafter referred to as (A) to (D)) is as follows: organosilicon compound: (A) + (B) component 1
It is preferable to use 0.05 to 1 mol of the component (C) + (D) based on the mol.

When the colloidal silica (E) is added, 1 to 30 parts by weight of (E) is used based on 100 parts by weight of the total of the components (A) + (B) + (C) + (D). Is preferred.

The amount of the reactive charge transporting compound (F) capable of forming a resin layer by reacting with the above-mentioned organosilicon compound or colloidal silica is as follows: (A) + (B)
It is preferable to use 1 to 500 parts by weight of (F) based on 100 parts by total weight of + (C) + (D) components. (A)
When the + (B) component is used outside the above range,
When the amount of the components (A) and (B) is small, the siloxane resin layer has a too low crosslinking density and insufficient hardness. Also, (A) +
If the component (B) is too large, the crosslink density is too high and the hardness is sufficient, but a brittle resin layer is formed. Excess or deficiency of the colloidal silica component (E) has the same tendency as that of the component (A) + (B). On the other hand, when the amount of the component (F) is small, the charge transporting ability of the siloxane resin layer is small, and the sensitivity and the residual charge increase. Be looked at.

The siloxane-based resin of the present invention having a structural unit having charge transporting ability and having a crosslinked structure is prepared by adding a catalyst or a crosslinking agent to a monomer, oligomer or polymer having a siloxane bond in the structural unit in advance. A bond may be formed to form a three-dimensional network structure, or a hydrolysis reaction and subsequent dehydration condensation may promote a siloxane bond to form a three-dimensional network structure from monomers, ologomers and polymers.

Generally, a three-dimensional network structure can be formed by a condensation reaction of a composition containing alkoxysilane or a composition containing alkoxysilane and colloidal silica.

As the catalyst for forming the three-dimensional network structure, alkali metal salts of organic carboxylic acids, nitrous acid, sulfurous acid, aluminate, carbonic acid and thiocyanic acid, and organic amine salts (tetramethylammonium hydroxide, tetramethylammonium) Ammonium acetate), tin organic acid salts (stannas octoate, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin mercaptide, dibutyltin thiocarboxylate, dibutyltin malate), aluminum, zinc octenoic acid, naphthenate, An acetylacetone complex compound is exemplified.

Further, an antioxidant having a hindered phenol, hindered amine, thioether or phosphite partial structure is added to the resin layer in the present invention, whereby
It is possible to effectively prevent the occurrence of fog and image blurring at high temperature and high humidity.

Among the above-mentioned antioxidants, hindered phenol-based and hindered amine-based antioxidants are effective in preventing fogging and image blurring at high temperature and high humidity, and these antioxidants are used in the resin layer of the present invention. When the resin layer is used, the thickness of the resin layer and the underlying charge transport layer is important for increasing the film strength.

That is, in the resin layer containing the siloxane-based resin of the present invention, as the thickness of the resin layer increases, fog and image blur at high temperature and high humidity tend to occur. When a hindered phenol-based or hindered amine-based antioxidant is added to the resin layer to prevent the occurrence, the occurrence of the fog and image blur is suppressed,
The balance of the film thickness of the charge transport layer thereunder has an important relationship with the film strength of all the photosensitive layers.

That is, the charge transport layer (hereinafter also referred to as CTL) has a thickness of 12 μm or more, the resin layer (hereinafter also referred to as OL) has a thickness of 2.5 μm or less, and the thickness ratio between the resin layer and the charge transport layer is expressed by the following formula. The range is important for achieving the object of the present invention.

0.01 ≦ film thickness of resin layer / film thickness of charge transport layer <
0.25, that is, when the thickness of the CTL is 12 μm or less and the resin layer is 2.5 μm or more, the brittleness of the film increases and cracks are easily generated. On the other hand, if the ratio of the thickness of the resin layer to the thickness of the charge transport layer is less than 0.01, the amount of deformation of the charge transport layer becomes relatively large, and the resin layer is likely to peel off.
When the ratio of the thickness of the resin layer to the thickness of the charge transport layer is 0.25 or more, cracks are easily generated.

On the other hand, the content of the hindered phenol or hindered amine antioxidant in the resin layer is 0.0
1-10% by weight is preferred. Less than 0.01% by weight has no effect on fog and image blur at high temperature and humidity, and 10% by weight
If the content is higher, the charge transporting ability in the resin layer decreases, the residual potential tends to increase, and the film strength decreases.

The antioxidant may be contained in the lower charge generation layer, charge transport layer, intermediate layer, and the like, if necessary. The amount of the antioxidant added to these layers is preferably 0.01 to 10% by weight based on each layer.

Here, the hindered phenol means compounds having a branched alkyl group at an ortho position to the hydroxyl group of the phenol compound and derivatives thereof (however, the hydroxyl group may be modified to alkoxy).

Examples of the hindered amine include compounds having an organic group represented by the following structural formula.

[0102]

Embedded image

(In the formula, R ₁₃ represents a hydrogen atom or a monovalent organic group, R ₁₄ , R ₁₅ , R ₁₆ , and R ₁₇ represent an alkyl group, and R ₁₈ represents a hydrogen atom, a hydroxyl group, or a monovalent organic group. Examples of the antioxidant having a hindered phenol partial structure include, for example, JP-A-1-118137 (P7 to P14).
The compounds described above are included, but the present invention is not limited thereto.

Examples of the antioxidant having a hindered amine partial structure include, for example, JP-A-1-118138 (P7-
The compounds described in P9) may also be mentioned, but the present invention is not limited thereto.

The following are representative compounds.

[0106]

Embedded image

[0107]

Embedded image

[0108]

Embedded image

[0109]

Embedded image

Examples of the commercially available antioxidants include the following compounds, for example, “Irganox 107
6, Irganox 1010, Irganox 1098, Irganox 245, Irganox 1330, Irganox 3114, Irganox 1076, 3,5-di-t-butyl-4 -Hydroxybiphenyl '' or more hindered phenols,
"Sanol LS2626", "Sanol LS765"
"Sanol LS2626", "Sanol LS770",
“Sanol LS744”, “Tinuvin 144”, “Tinuvin 622LD”, “Mark LA57”, “Mark LA”
67 "," Mark LA62 "," Mark LA68 ",
"Mark LA63" or more is a hindered amine type.

The layer structure of the electrophotographic photosensitive member of the present invention has a layer structure in which at least a charge generation layer, a charge transport layer and a resin layer are sequentially laminated on a conductive support. Each layer of the charge transport layer may be composed of a plurality of layers.

Examples of the charge generation material (CGM) contained in the charge generation layer of the present invention include phthalocyanine pigments,
Polycyclic quinone pigments, azo pigments, perylene pigments, indigo pigments, quinacridone pigments, azurenium pigments, squalilium dyes, cyanine dyes, pyrylium dyes, thiopyrylium dyes, xanthene dyes, triphenylmethane dyes,
Styryl dyes and the like, and these charge generating substances (C
GM) forms a layer alone or together with a suitable binder resin.

Examples of the charge transport material (CTM) contained in the charge transport layer include oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives,
Imidazolone derivatives, imidazoline derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds,
Benzidine compound, pyrazoline derivative, stilbene compound, amine derivative, oxazolone derivative, benzothiazole derivative, benzimidazole derivative, quinazoline derivative, benzofuran derivative, acridine derivative, phenazine derivative, aminostilbene derivative, poly-N-vinylcarbazole, poly-1- Vinylpyrene, poly-9-
Vinyl anthracene and the like can be mentioned, and these charge transporting substances (CTM) are usually formed into a layer together with a binder.

The charge generation layer (CGL) and the charge transport layer (CT
As the binder resin contained in L), 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,
Silicone resin, epoxy resin, silicon-alkyd resin, phenol resin, polysilane resin, polyvinyl carbazole and the like can be mentioned.

In the present invention, the ratio between the charge generating substance and the binder resin in the charge generating layer is from 1:10 to 1 by weight.
0: 1 is preferred. The thickness of the charge generation layer is preferably 5 μm or less, and particularly preferably 0.05 to 2 μm.

The charge transport layer is formed by dissolving the charge transport material and the binder resin in an appropriate solvent, and applying and drying the solution. The mixing ratio of the charge transport material and the binder resin is preferably from 10: 1 to 1:10 by weight.

Further, the amount of the charge transporting substance in the charge transporting layer is preferably at least 45% by weight. That is, by setting the amount of the charge transporting substance to 45% by weight or more, the charge transporting layer itself can be made a flexible layer and can absorb stress applied from the outside, and this has a synergistic effect with the high-strength resin layer of the present invention. Thereby, the film strength of the entire photosensitive layer can be improved.

Further, by increasing the thickness of the flexible charge transport layer, more external stress can be absorbed. The thickness of the charge transport layer is 12 μm or more as described above, preferably 21 μm or more, and most preferably 26 μm or more.
μm or more. As the thickness of the charge transport layer is increased, the film strength of the entire photosensitive layer is enhanced, and the fog and image blur characteristics with HH are also improved.

Further, an adhesive layer may be provided between the resin layer of the present invention and the charge transport layer.

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; 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 electroconductive support of the electrophotographic photoreceptor of the present invention may have a surface on which a sealed alumite film is formed.

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.

The photoreceptor of the present invention is effective to be applied to a high-speed machine requiring high durability characteristics. However, the photoreceptor of the present invention is used in a copying machine which forms a copy image of 30 sheets or more per minute. In this case, it is preferable to use a drum-shaped support having a diameter of 35 mm or more. That is, by setting the diameter to 35 mm or more, a highly durable photoconductor can be obtained.

The solvent or dispersion medium used in the production of the photoreceptor of the present invention includes n-butylamine, diethylamine, ethylenediamine, isopropanolamine, triethanolamine, triethylenediamine, N, N-dimethylformamide, acetone, methylethylketone,
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. 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.

Next, the coating method for producing the electrophotographic photosensitive member of the present invention includes dip coating, spray coating,
A coating method such as circular amount control type coating is used, but the coating process on the resin layer side of the photosensitive layer is performed by spray coating or circular amount control type in order to minimize dissolution of the lower layer film and to achieve uniform coating processing. (A typical example is the circular slide hopper type.)
It is preferable to use a coating method such as coating. The spray coating is described in detail in, for example, JP-A-3-90250 and JP-A-3-269238,
The circular amount control type coating is described in, for example, JP-A-58-1.
It is described in detail in JP-A-89061.

It is preferable that the photoreceptor of the present invention is dried by heating at a temperature of 50 ° C. or more, preferably 60 to 200 ° C., after the resin layer is formed. By this heating and drying, the remaining coating solvent can be reduced, and the curable resin layer can be sufficiently cured.

In the present invention, it is preferable to provide an intermediate layer having a barrier function between the conductive support and the photosensitive layer.

Examples of the material for the intermediate layer include casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyvinyl butyral, and phenol resin polyamides (nylon 6, nylon 66, nylon 610, copolymer nylon, alkoxymethyl). And an intermediate layer using polyurethane, gelatin, and aluminum oxide, or a hardening intermediate layer using a metal alkoxide, an organic metal chelate, or a silane coupling agent as described in JP-A-9-68870. The thickness of the intermediate layer is preferably from 0.1 to 10 μm, particularly preferably from 0.1 to 10 μm.
5 μm is preferred.

In the present invention, a coating for compensating for surface defects of the support is provided between the support and the intermediate layer, and interference fringes, which are problematic particularly when image input is performed by laser light, are performed. A conductive layer for the purpose of preventing generation and the like 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.

The electrophotographic photoreceptor of the present invention can be applied to general electrophotographic devices such as copiers, laser printers, LED printers, and liquid crystal shutter printers. It can be widely applied to devices such as light printing, plate making, and facsimile.

FIG. 1 is a sectional view showing an example of an image forming apparatus having the electrophotographic photosensitive member of the present invention.

In FIG. 1, reference numeral 10 denotes a photosensitive drum (photosensitive member) serving as an image bearing member, and an organic photosensitive layer is coated on the drum.
A photoreceptor coated with the resin layer of the present invention thereon is grounded and driven to rotate clockwise. 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, in order to eliminate the history of the photoconductor in the previous image formation, exposure by the exposure unit 11 using a light emitting diode or the like may be performed to remove electricity from the peripheral surface of the photoconductor.

After the photosensitive member is uniformly charged, the image exposure unit 13 performs image exposure based on the image signal. The image exposure device 13 in this figure uses a laser diode (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. At the periphery of the photoconductor drum 10, developing devices 14 each containing a developer having a toner and a carrier such as yellow (Y), magenta (M), cyan (C), and black (K) are provided. The color development 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 performed again by the scorotron charger 12, and the latent image of the second color is formed. 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 apparatus, the developing device 1
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) 1 is mounted on the peripheral surface of the photosensitive drum 10 in synchronization with the transfer timing.
8, the multicolor image is transferred collectively by sandwiching the fed recording paper P.

Next, the recording paper P is neutralized by a separation brush (separator) 19 which is brought into pressure contact with the transfer roller almost simultaneously, is separated by the peripheral surface of the photosensitive drum 10 and is conveyed to the fixing device 20, where the heat roller 201 and pressure roller 2
After the toner is welded by heating and pressurizing 02, the toner is discharged to the outside of the apparatus via the discharge roller 21. The transfer roller 18 and the separation brush 19 are retracted and separated from the peripheral surface of the photosensitive drum 10 after the recording paper P has passed to prepare for the formation of the next toner image.

On the other hand, the photosensitive drum 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 receives the charge removal by the exposure unit 11 and the charge by the charger 12 again. 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 retreats from the peripheral surface of the photoconductor drum 10.

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

An electrophotographic image forming apparatus is constructed by integrally combining the above-described photoreceptor, a developing unit, a cleaning unit, and other components as a process cartridge, and this unit is configured to be detachable from the apparatus main body. You may.
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.

The electrophotographic photoreceptor of the present invention can be applied to general electrophotographic devices such as copiers, laser printers, LED printers, and liquid crystal shutter printers. It can be widely applied to devices such as light printing, plate making, and facsimile.

[0147]

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

Preparation of Photoconductors of Examples 1 to 7 and Comparative Examples 1 to 4 Photoconductors were prepared as described below.

<Intermediate Layer> A polyamide resin (Amilan CM-8000: manufactured by Toray Industries, Inc.) 60 g methanol 1600 ml 1-butanol 400 ml was mixed and dissolved to prepare an intermediate layer coating solution. This coating solution was applied on a cylindrical aluminum substrate having a diameter of 80 mm by a dip coating method to form an intermediate layer having a thickness of 0.3 μm.

<Charge Generating Layer> Titanyl phthalocyanine 60 g Silicone resin solution (KR5240, 15% xylene-butanol solution: manufactured by Shin-Etsu Chemical Co., Ltd.) 700 g 2-butanone 2000 ml was mixed, and dispersed using a sand mill for 10 hours. A coating solution was prepared. This coating solution was applied on the intermediate layer by a dip coating method to form a 0.2 μm-thick charge generation layer.

<Charge Transport Layer> 4-Methoxy-4 '-(4-methyl-α-phenylstyryl) triphenylamine 200 parts Bisphenol Z-type polycarbonate (Iupilon Z300: manufactured by Mitsubishi Gas Chemical Company) 300 g 1,2-dichloroethane 2000 ml were mixed and dissolved to prepare a charge transport layer coating solution. This coating solution was applied on the charge generation layer by a dip coating method to form a charge transport layer having a film thickness shown in Table 1.

<Resin Layer> Trimethoxymethylsilane 180 g 1-butanol 280 ml 1% acetic acid aqueous solution 106 ml was mixed and stirred at 60 ° C. for 2 hours, and then 370 m
1-butanol was added and stirring was continued for 48 hours.

67.5 g of dihydroxymethyltriphenylamine (Exemplified Compound T-1), 1.7 g of an antioxidant (Sanol LS2626, manufactured by Sankyo) and 4.5 g of dibutyltin acetate were added and mixed. As a resin layer having a dry film thickness shown in Table 1,
Performed heat curing for 1 hour, Examples 1 to 7 and Comparative Examples 1 to
The photoreceptor having the resin layer of No. 4 of the present invention was produced.

Example 8 In Example 1, the dihydroxymethyltriphenylamine in the resin layer was replaced with 4- [2- (triethoxysilyl) ethyl] triphenylamine (the silicon-containing compound of Synthesis Example 1 of JP-A-10-251277). The photoreceptor having the resin layer of the present invention was prepared in exactly the same manner except that the above was used.

Example 9 Example 1 was repeated except that no antioxidant was used.
In the same manner as in the above, a photoreceptor having the resin layer of the present invention was produced.

Example 10 A photoconductor having a resin layer of the present invention was prepared in the same manner as in Example 1, except that the hindered phenol compound (1-10) was used as the antioxidant.

Example 11 A photoconductor having a resin layer of the present invention was prepared in the same manner as in Example 1, except that 100 g of colloidal silica (30% methanol solution) was added to the coating solution for the resin layer.

Comparative Example 5 A photoconductor was prepared in the same manner as in Example 1, except that no resin layer was used.

<Evaluation> Strength evaluation The strength evaluation was performed by placing a diamond needle with a curvature of 0.1 mm at the tip on a “Surface Tester” manufactured by HEIDON and moving the photosensitive drum at a speed of 5 mm / sec. The starting minimum load was measured.

2. Potential evaluation / Evaluation of actual shooting Evaluation was performed using this photoconductor as a digital copier Kon manufactured by Konica Corporation.
The ica 7050 was modified and mounted on an evaluator with an appropriate amount of exposure, the initial charging potential was set to -650 V, and the temperature was 30
Under the conditions of a temperature of 80 ° C. and a humidity of 80% (HH condition), 50,000 copies were actually evaluated. The evaluation was performed by measuring potential fluctuations (ΔVL, ΔVH) of the exposed and unexposed portions after 50,000 copies, a copy image (density, fog, image unevenness) of a human image wearing black and white clothes, and a photoconductor ( The occurrence of scratches and the presence or absence of film peeling) was visually evaluated. Table 1 shows the results.

[0161]

[Table 1]

As is clear from Table 1, those having the film thickness and the film thickness ratio of the charge transport layer and the resin layer within the range of the present invention were excellent in both the film strength and the actual image evaluation, but were out of the range of the present invention. (Comparative Example) has insufficient surface hardness, abrasion resistance, scratch resistance, etc., and causes cracks and scratches on the surface of the photoreceptor, resulting in image unevenness and fogging. I have.

[0163]

According to the present invention, by adopting the configuration as described above,
The surface hardness was high, the abrasion resistance and scratch resistance were high, and stable and good electrophotographic characteristics and electrophotographic images could be obtained even under high temperature and high humidity.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating an example of an image forming apparatus having an electrophotographic photosensitive member according to the present invention.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 10 Photosensitive drum (or photoreceptor) 11 Exposure part using light emitting diode etc. 12 Charging device 13 Image exposing device 14 Developing device 17 Paper feed roller 18 Transfer roller (transfer device) 19 Separation brush (separator) 20 Fixing device 21 Discharge roller 22 Cleaning device 30 Removable process cartridge in which photoconductor, charging device, transfer device / separator and cleaning device are integrated.

 ──────────────────────────────────────────────────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 AA02 AA03 AA04 AA08 AA20 AA28 AA35 AA54 AA58 BA58 BB33 BB49 BB57 EA12 FA03 FA06 FA07 FA27

Claims (11)

[Claims] 1. An electrophotographic photosensitive member having a charge generation layer, a charge transport layer, and a resin layer sequentially laminated on a conductive support, wherein the resin layer has a structural unit having charge transport performance,
And a layer containing a siloxane-based resin having a crosslinked structure, wherein the charge transport layer is 12 μm or more, and the resin layer is 2.
An electrophotographic photosensitive member having a thickness of 5 μm or less and a film thickness ratio between the resin layer and the charge transport layer falling within the range of the following formula. 0.01 ≦ thickness of resin layer / thickness of charge transport layer <0.25 2. The electrophotographic photoreceptor according to claim 1, wherein the resin layer further contains a hindered phenol or hindered amine antioxidant. 3. The electrophotographic photosensitive member according to claim 1, wherein the content of the charge transport agent in the charge transport layer is 45% by weight or more. 4. A siloxane-based resin having a structural unit having charge transport performance and having a crosslinked structure obtained by reacting an organic silicon compound having a hydroxyl group or a hydrolyzable group with a charge transport compound having a hydroxyl group. The electrophotographic photoreceptor according to any one of claims 1 to 3, wherein the resin is obtained. 5. The siloxane-based resin having a structural unit having a charge transporting property and having a crosslinked structure reacts an organosilicon compound having a hydroxyl group or a hydrolyzable group with a charge transporting compound having a silicon atom-containing group. The electrophotographic photoreceptor according to any one of claims 1 to 3, wherein the electrophotographic photoreceptor is a resin obtained by the above method. 6. The electrophotographic photosensitive member according to claim 1, wherein the charge transport layer has a thickness of 21 μm or more. 7. The electrophotographic photosensitive member according to claim 1, wherein the thickness of the charge transport layer is 26 μm or more. 8. The electrophotographic photosensitive member according to claim 1, wherein the conductive support is a cylindrical drum having a diameter of 35 mm or more. 9. An electrophotographic photosensitive member having at least a charge,
2. An electrophotographic image forming method comprising the steps of performing image exposure, development, and cleaning, wherein the electrophotographic photosensitive member is applied to the electrophotographic photosensitive member.
An electrophotographic image forming method, comprising using the electrophotographic photoreceptor according to any one of claims 1 to 8. 10. An electrophotographic photoreceptor, at least charged,
9. An electrophotographic image forming apparatus having means for image exposure, development, and cleaning, wherein the electrophotographic photosensitive member is provided on the electrophotographic photosensitive member.
An electrophotographic image forming apparatus using the electrophotographic photosensitive member according to any one of the above. 11. A process cartridge used in an electrophotographic image forming apparatus having an electrophotographic photosensitive member and at least means for charging, image exposure, development, and cleaning.
An electrophotographic photoreceptor and a charger according to any one of items 1 to 8,
A process cartridge having an image exposing device, a developing device, and a cleaning device in an integrated manner, and being designed to be freely inserted into and removed from the electrophotographic image forming apparatus.