JP2001117255A - Electrophotographic photoreceptor and image forming device using same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an electrophotographic photoreceptor excellent in environmental resistance, durability and photoconductive characteristics and an image forming device with the photoreceptor. SOLUTION: The electrophotographic photoreceptor contains electrically conductive fine particles and has a top layer comprising a hardened film formed from at least a reactive electron transferring material. The hardened film is formed from at least a compound of the formula F-[D-A]b, wherein F is an organic group derived from a photo-functional compound, D is a flexible subunit, A is a substituted silicon group having a hydrolyzable group of the formula-Si(R1)(3-a)(OR2)a (where R1 is H, alkyl or optionally substituted aryl, R2 is H, alkyl or trialkylsilyl and (a) is an integer of 1-3) and (b) is an integer of 1-4.

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 applied to a wide range of fields such as a copying machine, a printer and a facsimile, and an image forming apparatus using the same.

[0002]

2. Description of the Related Art Conventionally, an electrophotographic apparatus (for example, a plain paper copier (PPC), a laser printer, an LED printer, a liquid crystal printer, etc.) has an image forming process of charging, exposing, and developing a photoreceptor such as a rotating drum type. To form an image,
After transfer to a transfer material, fixing is performed to obtain a copy. The photoreceptors used for these include selenium, arsenic-selenium,
Inorganic photoreceptors such as cadmium sulfide, zinc oxide and a-Si are used, but research and development of organic photoreceptors (OPCs), which are also excellent in terms of manufacturability cost, are being actively conducted. A so-called function-separated-type laminated photoreceptor having a charge transport layer laminated thereon is excellent in terms of electrophotographic characteristics such as sensitivity, chargeability and repetition stability thereof, and various proposals have been made and put to practical use.

However, the durability required for electrophotographic photoreceptors has become severer year by year, and the wear and damage of the surface layer due to repeated use, especially the wear and tear of the surface layer which is remarkably increased by use under contact electrification. With respect to problems such as scratches and oxidative deterioration of the surface layer due to oxidizing gas such as ozone generated from a corona charger, studies on techniques necessary for improving durability are being continued.

[0004] Recently, copiers and printers using the contact charging system have been increasing for reasons such as reduction of generation of oxidizing gas and reduction of power supply cost. However, when an applied voltage having an AC component is used to stabilize the charging potential of the photoconductor, there has been a problem that abrasion of the photoconductor surface is increased. It is considered that the cause of this is that the binding of the binder resin on the surface of the photoreceptor is cut by the discharge generated between the surface of the photoreceptor and the contact charger, thereby reducing the molecular weight. It has been found that when the molecular weight of the binder resin on the photoreceptor surface is reduced, abrasion is significantly increased when mechanical cleaning such as a cleaning blade is performed.

As a method of reducing the wear of the photoreceptor, there is a method of applying a surface protective layer having high mechanical strength to the surface of the photoreceptor. A cross-linkable curable resin is excellent in terms of mechanical strength. However, if the cross-linkable resin alone is used, the surface protective layer becomes an insulating layer, and the photoelectric characteristics of the photoconductor are sacrificed. Specifically, the problem that the development potential margin is narrowed due to an increase in the light portion potential at the time of exposure, and the residual potential after static elimination is increased, especially when long-term repeated printing is performed, image density is reduced. There was a problem of lowering.

Further, as a method for imparting photoelectric characteristics of a photoreceptor, a method has been reported in which conductive metal oxide fine particles are dispersed in a surface protective layer as a resistance control material (Japanese Patent Application Laid-Open No. Sho 5).
No. 7-128344). The decrease in the photoelectric characteristics of the photoreceptor by this method is small, and the above-mentioned problems are remarkably improved. However, there is a problem that the resistance value of the metal oxide generally used as the conductive fine particles greatly depends on the humidity of the environment. Therefore, there has been an essential problem that the surface resistance of the photoreceptor is reduced particularly under high temperature and high humidity, and the image quality is largely reduced due to blurring of the electrostatic latent image.

As another method for improving the photoelectric characteristics of a photoreceptor, a method has been reported in which a charge transporting substance is dispersed in a binder resin, and then the binder resin is cured to form a surface protective layer ( JP-A-4-15659). In this method, the surface resistance of the photoreceptor did not depend on humidity, and there was no problem in image quality. However, the addition of a low-molecular-weight component such as a charge transporting substance inhibits the curing reaction and lowers the mechanical strength of the surface protective layer. Therefore, even when a cross-linking curable resin having high mechanical strength is used alone, the mechanical strength of the surface protective layer is greatly reduced by adding a low-molecular component such as a charge transport material essential for improving photoelectric properties. There was a problem.

From this point of view, it has been reported that the mechanical strength of the surface layer is improved by using a charge transport material having a functional group and reacting it with a thermoplastic binder resin ( JP-A-6-202354 and JP-A-5-323630). According to this method, a sufficient mechanical strength can be initially obtained without lowering the photoelectric characteristics of the photoconductor. However, with these surface layer configurations,
When used for a long time under contact charging, there has been a problem that the mechanical strength sharply decreases. It is thought that this is due to strong external stress such as breaking of the bond of the thermoplastic binder resin due to the application of AC voltage in contact charging.If mechanical cleaning such as a cleaning blade is used, abrasion may occur. Greatly increases.

As a solution to these problems,
There is a method of forming a crosslinked cured film using a reactive charge transporting material having an alkoxysilyl group and a monomer compound. According to this method, a three-dimensional crosslinked structure including a charge transport material is obtained, so that excellent mechanical strength can be obtained. In addition, since the charge transport material is included, the same photoelectric characteristics as those of the charge transport layer of the laminated photoreceptor are provided. You can also.

However, when the photoreceptor having such a configuration is used in an image forming apparatus of a scorotron charging system, if the airflow around the photoreceptor is insufficient, the photoreceptor is oxidized by ozone or nitrogen oxide (NOx) generated from the scorotron. Due to the deterioration, there were cases where the occurrence of density unevenness and the deterioration of image quality such as resolution were accompanied. Further, even when the contact charging method is used, when the applied voltage includes an AC component and a weak discharge is generated in the vicinity of the contact portion with the photoreceptor surface, if the number of continuous prints increases, it may be caused by ozone or NOx generation. In some cases, an apparent decrease in image quality was observed.

[0011] Since the main cause is oxidation deterioration of the charge transporting material, it can be improved by reducing the amount of the charge transporting material added to the crosslinked cured film. There were drawbacks such as doing.

[0012]

That is, an object of the present invention is to provide an electrophotographic photosensitive member having excellent environmental resistance, durability and photoelectric characteristics, and an image forming apparatus provided with the same.

[0013]

Means for Solving the Problems The present inventors have conducted intensive studies on the above-mentioned problems, and as a result, have reached the present invention. That is, the present invention

<1> An electrophotographic photosensitive member containing conductive fine particles and having at least an outermost surface layer of a cured film formed of a reactive charge transporting material.

<2> The electrophotographic photosensitive member according to <1>, wherein the cured film is a cured film formed by at least a compound represented by the following general formula (1).

[0016]

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In the general formula (I), F represents an organic group derived from a photofunctional compound. D represents a flexible subunit. A represents a substituted silicon group having a hydrolyzable group represented by -Si (R ₁ ) _(3-a) (OR ₂ ) _a (where R
₁ represents hydrogen, an alkyl group, or a substituted or unsubstituted aryl group. R ₂ represents hydrogen, an alkyl group, or a trialkylsilyl group. a represents an integer of 1 to 3. ). b is 1 to 4
Represents an integer.

<3> The cured film according to <1>, wherein the cured film is a charge transporting material having at least a hydroxy group and an isocyanate compound having three or more functional groups. It is an electrophotographic photosensitive member.

<4> An image forming apparatus including at least an electrophotographic photosensitive member and a charging unit thereof, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of <1> to <3>. The image forming apparatus is characterized in that the charging unit is of a contact charging type.

Since the electrophotographic photoreceptor of the present invention contains conductive fine particles as the outermost surface layer and has at least a cured film formed of a reactive charge transporting material, it has environmental resistance and durability. Excellent in photoelectric characteristics. In the electrophotographic photoreceptor of the present invention, since the amount of the reactive charge transporting material added can be reduced by adding conductive fine particles in the outermost surface layer, deterioration due to oxidation of the charge transporting material can be suppressed, In addition, if only the conductive fine particles are used, the temperature-humidity dependence of the photoelectric characteristics increases,
The addition of the charge transport material can minimize temperature and humidity fluctuations.

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION The electrophotographic photoreceptor of the present invention has an outermost surface layer comprising conductive fine particles and at least a cured film formed of a reactive charge transporting material.

(Outermost Surface Layer) The outermost surface layer comprises a cured film containing conductive fine particles and formed of at least a reactive charge transporting material.

-Conductive fine particles-The conductive fine particles include conductive or semiconductive metal powders (for example, carbon black, zinc, aluminum, copper, iron, nickel, chromium, titanium, etc.),
Metal oxide powder (TiO ₂ , SnO ₂ , Sb ₂ O ₃ , In
₂ O ₃ , ZnO, MgO, etc.). Further, as the conductive fine particles, those obtained by doping metal oxide with dopan (for example, Al-doped ZnO (ZnO-Al ₂
O ₃ ), Sn-doped SnO ₂ (SnO ₂ —Sb ₂ O ₃ ), S
n-doped _{In 2 O 3 (In 2 O} 3 -SnO 2), etc.) it can also be used.

As the conductive fine particles, tin oxide and tin oxide-doped antimony (tin oxide and antimony oxide) are preferable in terms of easy control of surface resistance and easy formation of a transparent film. Are simultaneously preferred).

The particle size (primary and secondary particles) of the conductive fine particles is preferably 0.3 μm or less from the viewpoint of maintaining the surface smoothness while maintaining an appropriate surface resistance value in the outermost surface layer. Preferably, more preferably 0.01-0.3μ
m. It is particularly preferable that the conductive fine particles contain 1 μm or more and 1% by weight or less.

The amount of the conductive fine particles varies depending on the composition and the particle size of the fine particles.
Preferably 10 ³ to 10 ¹⁴ Ωcm, more preferably 10 ⁵ Ωcm
〜１０10 ¹² Ωcm, more preferably 10 ⁷ 〜１０10 ¹² Ωc
It is preferable to add conductive fine particles so as to obtain m.

-A cured film formed by at least a reactive charge transporting material- A cured film formed by at least the reactive charge transporting material (hereinafter, sometimes simply referred to as a cured film) is at least the following general. A cured film formed of the compound represented by the formula (1), or a cured film formed of a charge transporting material having at least a hydroxy group and an isocyanate compound having three or more functional groups is preferable.

The cured film formed by at least the compound represented by the following general formula (1) will be described in detail.

[0029]

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In the general formula (I), F represents an organic group derived from a photofunctional compound. D represents a flexible subunit. A represents a substituted silicon group having a hydrolyzable group represented by -Si (R ₁ ) _(3-a) (OR ₂ ) _a (where R
₁ represents hydrogen, an alkyl group, or a substituted or unsubstituted aryl group. R ₂ represents hydrogen, an alkyl group, or a trialkylsilyl group. a represents an integer of 1 to 3. ). b is 1 to 4
Represents an integer.

In the general formula (I), A represents —Si (R ₁ )
_{(3-a) (OR 2} ) represents a substituted silicon group having a hydrolyzable group represented by _a, the substituted silicon group, the Si group, causing a crosslinking reaction with each other, three-dimensional Si- O-
This structure has a role of forming a Si bond, that is, an inorganic glassy network.

In the general formula (I), F is a unit having photoelectric characteristics, specifically, photocarrier transport characteristics,
Conventionally, a structure known as a charge transport material can be used as it is. Specific examples of F include compounds having a hole-transporting property, such as triarylamine compounds, benzidine compounds, arylalkane compounds, aryl-substituted ethylene compounds, stilbene compounds, anthracene compounds, and hydrazone compounds. And quinone compounds, fluorenone compounds, xanthone compounds, benzophenone compounds, cyanovinyl compounds,
A compound skeleton having an electron transporting property, such as an ethylene compound, can be used.

In the general formula (I), D represents a flexible subunit. Specifically, D represents an F site for imparting photoelectric properties and a direct bond to a three-dimensional inorganic glassy network. It represents a structure that has a function of binding the A portion to be bound and a function of imparting appropriate flexibility to the inorganic vitreous network having fragility on the other hand, and improving the strength as a film. Specifically, as D,
_{-C n H 2n -, C n} H (2 n-2) -, - C n H (2n-4) - a divalent hydrocarbon group (here represented, n represents an integer of 1 to 15 represented), -. COO -, - S -, - O -, - CH 2 -C 6
_{H 4 -, - N = CH} -, - (C 6 H 4) - (C 6 H 4) -,
And a combination thereof, and a substituent-introduced one.

In the general formula (I), b is preferably 2 or more. When b is 2 or more, the photofunctional organosilicon compound represented by the general formula (I) contains two or more Si atoms, easily forms an inorganic glassy network, and has a low mechanical strength. improves.

The compound represented by the general formula (I) includes
Compounds represented by the following general formula (II) are preferred. The compound represented by the following general formula (II) is a compound having a hole transporting ability, and is particularly preferable because it exhibits excellent hole generating ability and mechanical properties.

[0036]

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In the general formula (II), Ar _{1 to} Ar ₄ each independently represent a substituted or unsubstituted aryl group. A
r ₅ represents a substituted or unsubstituted aryl group or an arylene group. However, _{1 to} 4 of Ar _{1 to} Ar ₅ are:
—Y—Si (R ₄ ) _(3-c) (OR ₅ ) A substituted silicon group having a hydrolyzable group represented by _c (where R ₄ is a hydrogen, an alkyl group, a substituted or unsubstituted aryl group R ₅
Represents hydrogen, an alkyl group, or a trialkylsilyl group. c
Represents an integer of 1 to 3. Further, Y may _{-C x H 2x -, C x} '
A hydrocarbon group represented by H _{(2x'-2)-and -Cx "} H _{(2x" -4)} -(x represents an integer of 1 to 15; x 'and x "each independently represent 2 To 15), a substituted or unsubstituted divalent aryl group, or -CH = N-, -O-,
And a divalent substituent containing at least one or more of -COO-. ), K represents 0 or 1.

In the general formula (II), specifically, those represented by the following structural group 1 are preferable as Ar _{1 to} Ar ₄ .

[0039]

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In the structural group 1, Ar represents one shown in the following structural group 2.

[0041]

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In the structure group 1, Z ′ represents one shown in the following structure group 3.

[0043]

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In the structural group 1, X represents —Y—Si (R ₄ ) _(3-c)
(OR ₅₎ substituted silicon group having a hydrolyzable group represented by _{c (R 4, R 5,} Y, and c, R ₄ represented in the general formula _{(II), R 5, Y} , and c Is the same as.), But
Specifically, as Y, those shown in the following structural group 4 are particularly preferable, and those shown in the following structural group 5 may also be selected.

[0045]

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[0046]

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In the structural groups 1 to 5, R ₆ is hydrogen, carbon atom 1
A phenyl group substituted with an alkyl group having 1 to 4, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms,
Alternatively, it is selected from an unsubstituted phenyl group and an aralkyl group having 7 to 10 carbon atoms. R ₇ is selected from hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and halogen. m represents 0 or 1. s represents 0 or 1. t represents an integer of 1 to 3. x represents an integer of 1 to 10. x ′ represents an integer of 2 to 15. y and z each represent an integer of 1 to 5.

[0048] In the formula (II), specifically as Ar _5, preferably those k is represented by the following structural group 6 when 0, k is preferably those represented by the following structural County group 7 when the 1 .

[0049]

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[0050]

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In the structural groups 6 and 7, Z represents one shown in the following structural group 8.

[0052]

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In the structure group 8, W represents one shown in the following structure group 9.

[0054]

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In the structural groups 6 to 9, R ₈ is hydrogen, carbon number 1
Represents an alkyl group having 1 to 4, an alkoxy group having 1 to 4 carbon atoms, and halogen. q and r each represent an integer of 1 to 10. t ′ represents an integer of 1 or 2. s ′ represents an integer of 0 to 3. Further, R _6, R _7, s, t are, R _6, R ₇ in the structural group 1 to 5, s, is the same as t.

Hereinafter, specific examples of the compound represented by formula (II) will be shown, but the present invention is not limited to these specific examples. Further, a symbol in which "II-" is added to a compound number in the following table is referred to as an exemplified compound in the present specification (for example, a compound having a compound number of "12" is referred to as "exemplified compound (II-12)"). Shown).

[0057]

[Table 1]

[0058]

[Table 2]

[0059]

[Table 3]

[0060]

[Table 4]

[0061]

[Table 5]

[0062]

[Table 6]

[0063]

[Table 7]

[0064]

[Table 8]

[0065]

[Table 9]

[0066]

[Table 10]

[0067]

[Table 11]

[0068]

[Table 12]

[0069]

[Table 13]

[0070]

[Table 14]

[0071]

[Table 15]

[0072]

[Table 16]

[0073]

[Table 17]

[0074]

[Table 18]

[0075]

[Table 19]

[0076]

[Table 20]

[0077]

[Table 21]

[0078]

[Table 22]

[0079]

[Table 23]

[0080]

[Table 24]

[0081]

[Table 25]

[0082]

[Table 26]

[0083]

[Table 27]

[0084]

[Table 28]

[0085]

[Table 29]

[0086]

[Table 30]

[0087]

[Table 31]

[0088]

[Table 32]

[0089]

[Table 33]

[0090]

[Table 34]

[0091]

[Table 35]

[0092]

[Table 36]

[0093]

[Table 37]

[0094]

[Table 38]

[0095]

[Table 39]

[0096]

[Table 40]

[0097]

[Table 41]

[0098]

[Table 42]

[0099]

[Table 43]

[0100]

[Table 44]

[0101]

[Table 45]

[0102]

[Table 46]

[0103]

[Table 47]

[0104]

[Table 48]

[0105]

[Table 49]

[0106]

[Table 50]

[0107]

[Table 51]

[0108]

[Table 52]

[0109]

[Table 53]

[0110]

[Table 54]

The compounds represented by formula (I) may be used alone or in combination of two or more.

A compound represented by the following general formula (III) may be used in combination with the compound represented by the general formula (I) for the purpose of further improving the mechanical strength of the cured film.

[0113]

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In the general formula (III), A represents —Si (R ₁ )
_{(3-a) (OR 2} ) R 1 substituted silicon group (here having a hydrolyzable group represented by _a, R _{2, a} is, R in the general formula (I)
_{Same as 1} , R ₂ and a. ). B is composed of at least one group selected from a divalent or higher valent hydrocarbon group which may contain a branch, a divalent or higher phenyl group, and -NH-, or a combination thereof. a represents an integer of 1 to 3. n represents an integer of 2 or more.

The compound represented by the general formula (III)
Site is namely _{-Si (R 1) (3-} a) compounds a substituted silicon group having 2 or more having a hydrolyzable group represented by Q _a. The compound represented by the general formula (III) is represented by A
The part of the Si group contained in the site reacts with the compound represented by the general formula (I) or the compound represented by the general formula (III) to form a Si—O—Si bond, thereby three-dimensionally crosslinking and hardening. Form a film. Since the compound represented by the general formula (I) also has a similar Si group, it is possible to form a cured film by itself, but there are two compounds represented by the general formula (III). It is considered that the cross-linking structure of the cured film becomes three-dimensional because of having the above-mentioned A portion, so that it has stronger mechanical strength. Further, similarly to the D site in the compound represented by the general formula (I), it also has a role of giving the cured film an appropriate flexibility.

As the compound represented by the general formula (III), those represented by the following structural group 10 are preferable.

[0117]

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In the structural group 10, T ₁ and T ₂ each independently represent a divalent or trivalent hydrocarbon group which may be branched. A represents a substituted silicon group having a _{-Si (R 1) (3-} a) hydrolyzable group represented by Q _a. h, i, and j each independently represent an integer of 1 to 3, and the number of A in the molecule is 2
Is chosen to be above.

Hereinafter, specific examples of the compound represented by formula (III) are shown in Structural Group 11, but the present invention is not limited to these specific examples. Further, a symbol in which “III-” is added to a compound number in the following structural group 11 is referred to as an exemplary compound in the present specification (for example, a compound having a compound number of “12” is referred to as “exemplary compound (III-
12) ". )

[0120]

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The compound represented by the general formula (I) may be used in combination with another compound capable of undergoing a crosslinking reaction. As such a compound, various silane coupling agents and commercially available silicon-based hard coat agents can be used.

Examples of the silane coupling agent include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxysilane. Propyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, tetramethoxysilane, methyltrimethylsilane Methoxysilane, dimethyldimethoxysilane, and the like.

Commercially available hard coat agents include KP-8
5, CR-39, X-12-2208, X-40-97
40, X-41-1007, KNS-5300, X-4
0-2239 (all manufactured by Shin-Etsu Silicone Co., Ltd.) and A
Y42-440, AY42-441, AY49-208
(Above, manufactured by Dow Corning Toray Co., Ltd.).

A cured film formed of a charge transporting material having at least a hydroxy group and an isocyanate compound having three or more functional groups will be described in detail.

Particularly good photoelectric characteristics and abrasion resistance are at least one of the compounds represented by the following general formulas (A) to (C) wherein at least one kind of the charge transporting material having a hydroxy group is one of the compounds represented by the following general formulas (A) to (C). It is preferable from the viewpoint of the property.

[0126]

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In the general formula (A), R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, Represents an amino group substituted with an alkyl group of Formulas 1 and 2. T represents a divalent hydrocarbon group having 1 to 10 carbon atoms which may be branched in an aliphatic portion. n represents 0 or 1.

[0128]

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In the general formula (B), R ₄ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms,
An alkoxy group, a phenyl group, or a halogen atom as a substituent, an alkyl group having 1 to 5 carbon atoms or an alkyl group substituted with a halogen atom, or 1 to 5 carbon atoms.
5 represents a phenyl group substituted by an alkoxy group. T represents a divalent hydrocarbon group having 1 to 10 carbon atoms which may be branched in an aliphatic portion. n represents 0 or 1.

[0130]

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In the general formula (C), R ₅ represents hydrogen or an alkyl group having 1 to 5 carbon atoms. X is hydrogen, having 1 to 5 carbon atoms
Represents an alkyl group, a phenyl group, or a halogen atom as a substituent, an alkyl group having 1 to 5 carbon atoms or an alkyl group substituted with a halogen atom, or a phenyl group substituted with an alkoxy group having 1 to 5 carbon atoms. . T represents a divalent hydrocarbon group having 1 to 10 carbon atoms which may be branched in an aliphatic portion. Ar ₁ , Ar ₂ , and Ar ₃ each independently represent a phenyl group, a naphthyl group, or an anthracene group;
It may be substituted with a plurality of halogen groups, a plurality of alkyl groups having 1 to 5 carbon atoms, and a plurality of alkoxy groups having 1 to 5 carbon atoms.

In the general formulas (A) to (C), T specifically includes the following “T-1” to “T-22”.

[0133]

[Table 55]

[0134] In the general formula (C), specifically as Ar _1, include the following "Ar ₁ -1" - "Ar ₁ -18",
Specifically, as Ar ₂ and Ar ₃ , the following “Ar _x −1” to
"Ar _x -21" is exemplified. In the table, the direction in which the two hands bond to the aliphatic group T or N atom may be either direction.

[0135]

[Table 56]

[0136]

[Table 57]

Specific examples of the compounds represented by formulas (A) to (C) ("A-1" to "A-46",
"B-1" to "B-19", "C-1" to "C-2"
3)), respectively, but the present invention is not limited to these specific examples.

[0138]

[Table 58]

[0139]

[Table 59]

[0140]

[Table 60]

[0141]

[Table 61]

Along with the compounds represented by the general formulas (A) to (C), the chargeability can be improved without improving properties such as flexibility, film formability, humidity dependency and surface adhesion, or reducing the crosslink density. For the purpose of adjusting the concentration of the transport substance, if necessary, a compound having two or more hydroxy groups such as a glycol compound and a bisphenol compound may be used in combination. These compounds form a crosslinked structure by an addition polymerization reaction with an isocyanate compound in the same manner as the compounds of the above structural formulas (A) to (C).

The compound having two or more hydroxy groups can be freely selected from compounds having two or more hydroxy groups in the molecule and capable of undergoing addition polymerization with isocyanate. Examples thereof include ethylene glycol, propylene glycol, and the like. Butanediol, polyethylene glycol, bisphenol compounds and the like. Other examples of the compound having two or more hydroxy groups include various polymers and oligomers having a reactive hydroxy group, such as acrylic polyols and oligomers thereof, polyester polyols and oligomers thereof. Specific examples of the compound having two or more hydroxy groups (“H-1” to
"H-16") are shown below.

[0144]

[Table 62]

The isocyanate compound having three or more functional groups is used as a cured film to form a three-dimensional network structure by crosslinking.
That is, those having three or more reactive isocyanate groups are shown.

Examples of the isocyanate compound having three or more functional groups include derivatives obtained from isocyanate monomers and modified polyisocyanates such as prepolymers.

Specific examples of the isocyanate compound having three or more functional groups include an adduct modified product obtained by adding isocyanate to a polyol having three or more functional groups, a buret modified product obtained by modifying a compound having a urea bond with isocyanate, and urethane. Modified allophanate and isocyanurate in which isocyanate is added to the group, and modified carbimide are exemplified.

At least one of the isocyanate compounds having 3 or more functional groups is a burette-modified hexamethylene diisocyanate represented by the following structural formula (D) or a hexamethylene diisocyanate represented by the following structural formula (E) It is particularly preferred to be selected from the isocyanurate modified products of the above. The burette-modified hexamethylene diisocyanate and the isocyanurate-modified hexamethylene diisocyanate represented by structural formulas (D) and (E) have mechanical strength,
It is particularly preferable because it shows particularly excellent characteristics in terms of electric characteristics.

[0149]

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Other examples of the isocyanate compound having three or more functional groups include those represented by the following structural formulas (i) to (iii).

[0151]

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In addition to the isocyanate compound having three or more functional groups, another isocyanate compound can be used in combination. Other isocyanate compounds include tolylene diisocyanate (TDI), diphenylmethane diisosocyanate (MDI), 1,5-naphthylene diisocyanate, tolidine diisocyanate,
1,6-hexamethylene diisocyanate, xylene diisocyanate, lysine isocyanate, tetramethyl xylene diisocyanate, 1,3,6-hexamethylene triisocyanate, lysine ester triisocyanate, 1,6,11-undecane triisocyanate,
General isocyanate monomers such as 1,8-isocyanate-4-isocyanatomethyloctane, triphenylmethane triisocyanate, and tris (isocyanatephenyl) thiophosphate are exemplified.

The modified isocyanate compound having three or more functional groups is included in the modified polyisocyanate, and a blocked isocyanate reacted with a blocking agent for temporarily masking the activity of the isocyanate group is preferably used in combination. it can. This is preferable from the viewpoint of extending the pot life of the coating liquid.

The mixing ratio of the charge transporting material having a hydroxy group and the isocyanate compound having a functional group number of 3 or more is such that the ratio of (total number of hydroxy groups) :( total number of isocyanate groups) is preferably 2: 1 to 1: 1. : 2, more preferably in the range of 1.5: 1 to 1: 1.5, even more preferably in the range of 1.2: 1 to 1: 1.2. If the mixing ratio (2: 1) is exceeded and an excess of hydroxy groups remains, the hydrophilicity of the surface of the outermost surface layer increases, and the image characteristics under high temperature and high humidity may deteriorate.
If the mixing ratio is less than (1: 2), the crosslink density of the three-dimensional network structure becomes small, and the mechanical strength may be insufficient. Therefore, it is necessary to pay attention to the reaction conditions and the like.
Care must be taken because the isocyanate compound may be deactivated by moisture in the air and the like, and the number of reactive isocyanate groups may decrease. In that case, it is advisable to prepare such that the isocyanate group is slightly excessive.

The charge transport material content in the outermost surface layer (cured film containing the conductive fine particles) is preferably 10 to 60% by weight, more preferably 15 to 50% by weight.
More preferably, 20 to 40% by weight is suitable. If the content exceeds 60% by weight, image quality deterioration such as density unevenness or resolution deterioration, which is considered to be caused by oxidation deterioration of the charge transport material, may occur during continuous printing. Also,
When the content is less than 10% by weight, the photoelectric characteristics are reduced,
In some cases, a problem such as an increase in the bright portion potential occurs.

A fluorine atom-containing compound can be added to the outermost surface layer (cured film containing the conductive fine particles) for the purpose of imparting surface lubricity. By improving the surface lubricity, the coefficient of friction with the cleaning member is reduced, and the wear resistance can be improved. It also has the effect of preventing toner and paper dust from adhering to the surface of the photoreceptor, which helps to improve the life of the photoreceptor.

As the fluorine-containing compound, a fluorine-containing polymer such as polytetrafluoroethylene may be added as it is, or fine particles of such a polymer may be added. Further, in the case of a cured film formed of the compound represented by the general formula (I), it is preferable that a compound capable of reacting with alkoxysilane is added as a fluorine-containing compound to constitute a part of the crosslinked film. Examples of such a fluorine atom-containing compound include (tridecafluoro-1,1,2,2-tetrahydrooctyl) triethoxysilane, (3,3,3-trifluoropropyl)
Trimethoxysilane, 3- (heptafluoroisopropoxy) propyltriethoxysilane, 1H, 1H, 2
H, 2H-perfluoroalkyltriethoxysilane,
1H, 1H, 2H, 2H-perfluorodecyltriethoxysilane, 1H, 1H, 2H, 2H-perfluorooctyltriethoxysilane, and the like.

The amount of the fluorine-containing compound to be added is preferably 20% by weight or less. Exceeding this may cause a problem in the film formability of the cured film.

Although the outermost surface layer (cured film containing the conductive fine particles) has sufficient oxidation resistance as described above, an antioxidant is added for the purpose of imparting stronger oxidation resistance. It may be added. As the antioxidant, a hindered phenol-based or hindered amine-based antioxidant is preferable, and an organic sulfur-based antioxidant, a phosphite-based antioxidant,
Known antioxidants such as dithiocarbamate-based antioxidants, thiourea-based antioxidants, and benzimidazole-based antioxidants may be used. The addition amount of the antioxidant is preferably 15% by weight or less, more preferably 10% by weight or less.

Hindered phenolic antioxidants include 2,6-di-t-butyl-4-methylphenol,
2,5-di-t-butylhydroquinone, N, N′-hexamethylenebis (3,5-di-t-butyl-4-hydroxyhydrocinnamide, 3,5-di-t-butyl-4
-Hydroxy-benzylphosphonate-diethyl ester, 2,4-bis [(octylthio) methyl] -o
-Cresol, 2,6-di-t-butyl-4-ethylphenol, 2,2′-methylenebis (4-methyl-6
t-butylphenol), 2,2′-methylenebis (4
-Ethyl-6-t-butylphenol), 4,4'-butylidenebis (3-methyl-6-t-butylphenol), 2,5-di-t-amylhydroquinone, 2-t-
Butyl-6- (3-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenylacrylate, 4,
4′-butylidenebis (3-methyl-6-t-butylphenol), and the like.

The outermost surface layer (cured film containing the conductive fine particles) contains one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential, and reducing fatigue upon repeated use. Can be done. Such electron acceptors include, for example, succinic anhydride, maleic anhydride,
Dibromo maleic anhydride, phthalic anhydride, tetrabromophthalic anhydride, tetracyanoethylene, tetracyanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, chloranil, dinitroanthraquinone, trinitrofluorenone, picric acid, o-nitrobenzoate Acid, p
-Nitrobenzoic acid, phthalic acid and the like. Among them, fluorenone type, quinone type, Cl, CN, NO ₂
A benzene derivative having an electron-withdrawing substituent such as

It is also possible to add other known additives for forming a coating film to the outermost surface layer (cured film containing the conductive fine particles), such as a leveling agent, an ultraviolet absorber, and a light stabilizing agent. Known agents such as agents and surfactants can be used.

In order to form the outermost surface layer (the cured film containing the conductive fine particles), a mixture of the above-mentioned various materials and various additives is applied on the photosensitive layer and heat-treated. Thereby, a cross-linking curing reaction occurs three-dimensionally, and a strong cured film is formed.

A solvent may be added to the outermost surface layer (cured film containing the conductive fine particles) as necessary to facilitate application. Specifically, water, methanol, ethanol, n-propanol, n-butanol, benzyl alcohol, methyl cellosolve, ethyl cellosolve, acetone, methyl ethyl ketone, cyclohexanone, methyl acetate, n-butyl acetate, dioxane, tetrahydrofuran, methylene chloride, chloroform , Dimethyl ether, dibutyl ether and the like can be used alone or in combination of two or more.

In the formation of the outermost surface layer (cured film containing the conductive fine particles), known means can be used to uniformly disperse the conductive fine particles. Examples thereof include a ball mill, a sand mill, and an attritor. And a dispersing means such as a dyno mill. In the formation of the outermost surface layer (cured film containing the conductive fine particles), the coating method includes a blade coating method, a Meyer bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, and a curtain. An ordinary method such as a coating method can be used. The thickness of the crosslinked cured film is preferably from 1 to 15, more preferably from about 3 to 10 μm.

In the formation of the outermost surface layer (cured film containing the conductive fine particles), the cross-linking curing reaction may be performed without a catalyst, but an appropriate catalyst may be used. Examples of the catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, formic acid, acetic acid, and trifluoroacetic acid; bases such as ammonia and triethylamine; organic tin compounds such as dibutyltin diacetate, dibutyltin dioctoate and stannous octoate; n-butyl titanate, organic titanium compounds such as tetraisopropyl titanate, iron salts of organic carboxylic acids, manganese salts,
Cobalt salts, zinc salts, zirconium salts and the like.
The temperature at the time of the curing reaction is not particularly limited as long as it does not affect the underlying photosensitive layer, but is preferably set to a temperature between room temperature and 150 degrees.

(Other Configurations) The electrophotographic photoreceptor of the present invention may have any configuration other than the outermost surface layer. For example, a photosensitive layer and the outermost surface layer are sequentially formed on a conductive support. Configuration. The photosensitive layer may have any structure of a function-separated type photosensitive layer including a single-layer type photosensitive layer, a charge generation layer, and a charge transport layer, but the function-separated type structure has a wider range of photoelectric characteristics and material selection. It is preferable from the aspect of the size. Further, an undercoat layer may be provided between the conductive support and the photosensitive layer.

Examples of the conductive support include metals such as aluminum, nickel, chromium, and stainless steel; and aluminum, titanium, nickel, chromium, stainless steel, gold, vanadium, tin oxide, indium oxide, and the like.
Examples include a plastic film provided with a thin film of ITO or the like, or a paper or plastic film coated or impregnated with a conductivity-imparting agent. These conductive supports are used in an appropriate shape such as a drum shape, a sheet shape, and a plate shape, but are not limited thereto. Further, if necessary, the surface of the conductive support can be subjected to various treatments within a range that does not affect the image quality.
For example, surface oxidation treatment, chemical treatment, coloring treatment, and the like, and irregular reflection treatment such as graining can be performed.

The undercoat layer prevents charge injection from the conductive support to the photosensitive layer during charging of the photosensitive layer having a laminated structure, and integrally bonds the photosensitive layer to the conductive support. It acts as an adhesive layer to hold, and in some cases, acts to prevent light reflection on the conductive support.

The binder resin used for the undercoat layer is polyethylene resin, polypropylene resin, acrylic resin, methacrylic resin, polyamide resin, vinyl chloride resin, vinyl acetate resin, phenol resin, polycarbonate resin, polyurethane resin, polyimide resin, chloride resin. Vinylidene resin, polyvinyl acetal resin, vinyl chloride-vinyl acetate copolymer, polyvinyl alcohol resin, water-soluble polyester resin, nitrocellulose, casein, gelatin,
Known materials such as polyglutamic acid, starch, starthiacetate, amino starch, polyacrylic acid, polyacrylamide, zirconium chelate compound, titanyl chelate compound, titanyl alkoxide compound, organic titanyl compound, and silane coupling agent can be used. Can be used alone or in combination of two or more. Further, it can be used by mixing with fine particles such as titanium oxide, silicon oxide, zirconium oxide, barium titanate, and silicone resin.

The thickness of the undercoat layer is 0.01 to 10 μm.
m, preferably in the range of 0.05 to 2 μm.
As a coating method, a usual method such as a blade coating method, a Meyer bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, a curtain coating method, or the like can be used.

The function-separated type photosensitive layer (charge generation layer, charge transport layer) will be described. First, the charge generation layer will be described. The charge generation layer contains at least a charge generation material and a binder resin. As the charge generation material, amorphous selenium, crystalline selenium-tellurium alloy, selenium-arsenic alloy, other selenium compounds and alloys, zinc oxide,
Examples include inorganic photoconductive materials such as titanium oxide, organic pigments such as phthalocyanine, squarylium, anthantrone, perylene, azo, anthraquinone, pyrene, pyrylium salts, and thiapyrylium salts, and dyes.

The phthalocyanine-based compound is desirable in terms of photosensitivity and stability, and particularly preferred are metal-free phthalocyanine, oxytitanium phthalocyanine, halogenated gallium phthalocyanine, hydroxygallium phthalocyanine, and halogenated tin phthalocyanine. Among these, the Bragg angle (2θ ±
0.2 °) is 7.4 °, 16.6 °, 25.5 °, 2
Chlorogallium phthalocyanine having a specific crystal form having a strong diffraction peak at 8.3 ° or a Bragg angle (2θ ± 0.2 °) in an X-ray diffraction spectrum of 7.
5 °, 9.9 °, 12.5 °, 16.3 °, 18.6
Hydroxygallium phthalocyanine having a specific crystal form having strong diffraction peaks at °, 25.1 °, and 28.3 ° has high charge generation efficiency with respect to a wide range of light from visible light to near infrared light. And particularly preferred.

Examples of the binder resin in the charge generation layer include polyvinyl butyral resin, polyvinyl formal resin, partially modified polyvinyl acetal resin, polycarbonate resin, polyester resin, acrylic resin, polyvinyl chloride resin, polystyrene resin, polyvinyl acetate resin, and chloride resin. Examples thereof include a vinyl-vinyl acetate copolymer, a silicone resin, a phenol resin, and a poly-N-vinyl carbazole resin, but are not limited thereto. These binder resins can be used alone or in combination of two or more.

Solvents used for forming the charge generating layer by coating include methanol, ethanol, n-propanol, n-butanol, benzyl alcohol, methyl cellosolve, ethyl cellosolve, acetone, methyl ethyl ketone, cyclohexanone, methyl acetate, and n-acetate. Conventional organic solvents such as butyl, dioxane, tetrahydrofuran, methylene chloride, chloroform and the like can be used alone or in combination of two or more. As the application method, a usual method such as a blade coating method, a Meyer bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, a curtain coating method, or the like can be used.

The mixing ratio (weight ratio) of the charge generation material to the binder resin is preferably in the range of 10: 1 to 1:10. The thickness of the charge generation layer is generally 0.1 to
It is 5 μm, preferably 0.2 to 2.0 μm.

The charge transport layer will be described. The charge transport layer is formed containing a charge transport material and a binder resin, or is formed containing a polymer charge transport material.

Examples of the charge transport material include quinone compounds such as p-benzoquinone, chloranil, bromanyl, and anthraquinone; tetracyanoquinodimethane compounds;
Fluorenone compounds such as 2,4,7-trinitrofluorenone, xanthone compounds, benzophenone compounds, cyanovinyl compounds, electron transporting compounds such as ethylene compounds, triarylamine compounds, benzidine compounds, arylalkane compounds And hole-transporting compounds such as aryl-substituted ethylene compounds, stilbene compounds, anthracene compounds and hydrazone compounds. These charge transport materials can be used alone or in combination of two or more.

Examples of the charge transporting material include a triphenylamine compound represented by the following general formula (IV) and a benzidine compound represented by the following general formula (V):
It is particularly preferable because it has high charge (hole) transport ability and excellent stability. These may be used alone or in combination of two or more.

[0180]

Embedded image

In the general formula (IV), R ₁₄ represents a hydrogen atom or a methyl group. Further, n means 1 or 2. A
r ₆ and Ar ₇ each independently represent a substituted or unsubstituted aryl group, and examples of the substituent include a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 1 to 3 carbon atoms. Represents a substituted amino group substituted with an alkyl group.

[0182]

Embedded image

In formula (V), R ₁₅ and R _{15 ′} each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. R ₁₆ , R
_{16 ′} , R ₁₇ and R _{17 ′} each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an amino substituted with an alkyl group having 1 to 2 carbon atoms. Represents a group. m and n each independently represent 0, 1, or 2.

Specific examples of the triphenylamine-based compound represented by the general formula (IV) are shown below.
It is not limited to these specific examples. In addition, a symbol in which "IV-" is added to a compound number in the following table is an exemplified compound in the present specification (for example, a compound having a compound number of "12" is referred to as "exemplified compound (IV-12)"). Shown).

[0185]

[Table 63]

[0186]

[Table 64]

[0187]

[Table 65]

Hereinafter, specific examples of the benzidine-based compound represented by the general formula (V) are shown, but the present invention is not limited to these specific examples. In addition, a symbol in which "V-" is added to a compound number in the following table is an exemplary compound in the present specification (for example, the compound number is "12").
Shows "Exemplified compound (V-12)". ).

[0189]

[Table 66]

[0190]

[Table 67]

[0191]

[Table 68]

Examples of the binder resin in the charge transport layer include polycarbonate resin, polyester resin, methacrylic resin, acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polystyrene resin, polyvinyl acetate resin, styrene-butadiene copolymer, Vinylidene chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone-alkyd resin, phenol-formaldehyde resin, styrene-acrylic resin, styrene- Known resins such as alkyd resin, poly-N-vinylcarbazole, and polysilane are exemplified.

The compounding ratio (weight ratio) of the charge transport material to the binder resin is preferably from 10: 1 to 1: 5.

Examples of the polymer charge transporting material include poly-
Known materials having a charge transporting property, such as N-vinylcarbazole and polysilane, may be mentioned. Examples of the polymer charge transport material include JP-A-8-176293 and JP-A-8-176293.
The polyester-based polymer charge transporting material disclosed in JP-A-208820 has a high charge transporting property and is particularly preferable. The polymer charge transport material alone can form a film, but may be formed by mixing with the binder resin in the charge transport layer. Further, the above-described low molecular charge transport material may be added.

Solvents used for forming the charge transport layer include aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, ketones such as acetone and 2-butanone, and halogens such as methylene chloride, chloroform and ethylene chloride. Ordinary organic solvents such as cyclic or linear ethers such as fluorinated aliphatic hydrocarbons, tetrahydrofuran, ethyl ether and dioxane can be used alone or in combination of two or more.

As the method of applying the charge transport layer, the same known methods as those described for the surface protective layer and the charge generation layer can be used. The preferred thickness of the charge transport layer is 5 to 50 μm, and more preferably 10 to 40 μm.

The single-layer type photosensitive layer will be described. The single-layer type photosensitive layer is formed containing the charge generation material and a binder resin. As the binder resin, the same resins as those used for the charge generation layer and the charge transport layer can be used. The content of the charge generating material in the single-layer photosensitive layer is
It is preferably about 10 to 85% by weight, more preferably 2 to 85% by weight.
0 to 50% by weight.

A charge transporting material or a polymer charge transporting material may be added to the single-layer type photosensitive layer for the purpose of improving the photoelectric characteristics. The addition amount is preferably 5 to 50% by weight. The same solvent and the same coating method as those described for the charge generation layer and the charge transport layer can be used. The single-layer type photosensitive layer has a thickness of 5 to 50 μm.
m, and more preferably 10 to 40 μm.

In the electrophotographic photoreceptor of the present invention, each of the above-mentioned layers (charge transport layer, charge transport layer, single-layer type photosensitive layer) is provided for the purpose of preventing deterioration due to oxidizing gas such as ozone generated in the charger. Alternatively, an antioxidant may be added. Even if there is the outermost surface layer, the oxidizing gas may permeate the surface protective layer and penetrate into the charge transport layer, thereby preventing oxidative deterioration. As the antioxidant, those similar to those used for the outermost surface layer can be used. The addition amount of the antioxidant is preferably 15% by weight or less of the charge transporting layer, and more preferably 10% by weight or less.

In the electrophotographic photoreceptor of the present invention, each of the above-mentioned layers (charge transport layer, charge transport layer, single-layer type photosensitive layer) may contain other known additives used for forming a coating film. It is possible to add known substances such as a leveling agent, an ultraviolet absorber, a light stabilizer, and a surfactant.

Hereinafter, specific examples of the electrophotographic photosensitive member of the present invention are shown in FIGS. 1 to 3 are enlarged sectional views showing an example of the electrophotographic photosensitive member of the present invention.
Shows a photosensitive layer having a laminated structure (separated function type), and FIG. 3 shows a photosensitive layer having a single layer structure.

In FIG. 1, a charge generation layer 2, a charge transport layer 3, and an outermost surface layer 4 are sequentially provided on a conductive support 4. In FIG. 2, a charge transport layer 3, a charge generation layer 2, and an outermost surface layer 4 are sequentially provided on a conductive support 4. In FIG. 3, a single-layer type photosensitive layer 5 and an outermost surface layer 4 are sequentially provided on a conductive support 4.

[Image Forming Apparatus] The image forming apparatus of the present invention is an electrophotographic image forming apparatus having the electrophotographic photosensitive member of the present invention.
Exposure means such as an ED array, development means for forming an image using toner, transfer means for copying a toner image onto a medium such as paper, fixing means for fixing a toner image on a medium such as paper, toner attached to a photoreceptor Cleaning means for removing dust and dirt, etc., and static elimination means for removing an electrostatic latent image remaining on the surface of the photoreceptor are provided by a known method as necessary.

As the charging method, a non-contact method using a conventionally known corotron or scorotron can be preferably employed. However, since the electrophotographic photoreceptor of the present invention has a high mechanical strength, the electrophotographic photoreceptor exhibits particularly excellent durability when using a contact charging system in which stress on the photoreceptor is large.

In the contact charging method, the surface of the photoreceptor is charged by applying a voltage to the conductive member brought into contact with the surface of the photoreceptor. The shape of the conductive member may be any of a brush shape, a blade shape, a pin electrode shape, a roller shape, and the like, but a roller-shaped member is particularly preferable. Normal,
The roller-shaped member is composed of a resistance layer, an elastic layer supporting them, and a core material from the outside. Further, a protective layer can be provided outside the resistance layer as needed.

The roller-shaped member rotates at the same peripheral speed as that of the photoreceptor by contacting the photoreceptor without any driving means, and functions as a charging means. However, some kind of driving means may be attached to the roller member, and the roller member may be rotated at a peripheral speed or direction different from that of the photoconductor.

The material of the core material has conductivity, and generally, iron, copper, brass, stainless steel, aluminum, nickel or the like is used. In addition, a resin molded product in which conductive particles and the like are dispersed can be used.

The elastic layer is made of a material having conductivity or semi-conductivity, and is generally a material in which conductive particles or semi-conductive particles are dispersed in a rubber material.

As the rubber material, EPDM, polybutadiene, natural rubber, polyisobutylene, SBR, CR, N
BR, silicone rubber, urethane rubber, epichlorohydrin rubber, SBS, thermoplastic elastomer, norbornene rubber, fluorosilicone rubber, ethylene oxide rubber and the like are used.

The conductive particles or semiconductive particles
Carbon black, zinc, aluminum, copper, iron,
Metals such as nickel, chromium and titanium, ZnO-Al
_TwoO_Three, SnO_Two-Sb_TwoO_Three, In_TwoO_Three-SnO_Two, ZnO
-TiO_Two, MgO-Al_TwoO _Three, FeO-TiO_Two, Ti
O_Two, SnO_Two, Sb_TwoO_Three, In_TwoO_Three, ZnO, MgO, etc.
Metal oxides can be used.
Alternatively, two or more kinds may be used in combination.

The material of the resistive layer and the protective layer is a material obtained by dispersing conductive particles or semiconductive particles in a binder resin and controlling the resistance. The resistivity is 10 ³ to 10.
¹⁴ Ωcm, preferably 10 ⁵ to 10 ¹² Ωcm, more preferably 10 ⁷ to 10 ¹² Ωcm. The thickness is 0.01 to 1000 μm, preferably 0.1 to 500 μm.
μm, more preferably 0.5 to 100 μm. Acrylic resin, cellulose resin, polyamide resin, methoxymethylated nylon, ethoxymethylated nylon, polyurethane resin, polycarbonate resin, polyester resin, polyethylene resin, polyvinyl resin, polyarylate resin, polythiophene resin, PF
Polyolefin resins such as A, FEP and PET, and styrene butadiene resin are used. As conductive particles or semiconductive particles, the same carbon black as the elastic layer,
Metals and metal oxides are used. If necessary, an antioxidant such as hindered phenol and hindered amine,
Fillers such as clay and kaolin and lubricants such as silicone oil can be added.

As means for forming the resistance layer and the protective layer, a blade coating method, a Meyer bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, a curtain coating method and the like can be used. .

As a method for charging the photoreceptor using the conductive member, a voltage is applied to the conductive member. The applied voltage may be a DC voltage or a DC voltage with an AC voltage superimposed thereon.

As the range of the applied voltage, the DC voltage is a positive or negative 50 to 50 depending on the required photosensitive member charging potential.
2000V is preferable, and 100 to 1500V is particularly preferable. When the AC voltage is superimposed, the peak-to-peak voltage is 40
0-2500V, preferably 800-2000V, more preferably 1200-2000V. The frequency of the AC voltage is 50 to 20,000 Hz, preferably 10 to
0 to 5,000 Hz.

FIG. 4 is a schematic diagram showing an example of the image forming apparatus of the present invention to which the electrophotographic photosensitive member of the present invention is applied. The photoreceptor 10, which is an electrophotographic photoreceptor of the present invention, a charging roll 12, which is a contact charging type charging means, a laser exposure optical system 14, a developing device 16 using powder toner, a transfer roll 18, a mechanical cleaning It has a cleaning blade 20 and a fixing roll 22 as means.

[0216]

EXAMPLES (Preparation of base photoreceptor) On a 30 mm outer diameter aluminum substrate subjected to honing treatment, 20 parts of a zirconium compound (trade name: Organotics ZC540, manufactured by Matsumoto Pharmaceutical Co., Ltd.) and a silane compound (trade name: A1100,
A solution consisting of 2.5 parts of Nippon Unicar Co., Ltd. and 45 parts of butanol and polyvinyl butyral resin (trade name: Eslec BM-S, manufactured by Sekisui Chemical Co., Ltd.) is applied by a dip coating method, and dried by heating at 150 ° C. for 10 minutes. An undercoat layer having a thickness of 1.0 μm was formed.

The Bragg angles (2θ ± 0.2 °) in the X-ray diffraction spectrum were 7.5 °, 9.9 °, 12.5 °
°, 16.3 °, 18.6 °, 25.1 °, 28.3 °
A part of hydroxygallium phthalocyanine having a specific crystal form having a strong diffraction peak is mixed with 1 part of polyvinyl butyral (Eslec BM-S, Sekisui Chemical) and 100 parts of n-butyl acetate, and mixed with glass beads using a paint shaker. After treating and dispersing for 1 hour, the obtained coating solution was dip-coated on the undercoat layer, and dried by heating at 100 ° C. for 10 minutes to form a charge generation layer having a thickness of about 0.15 μm.

A coating solution prepared by dissolving 2 parts of a benzidine compound of the exemplified compound (V-27) and 3 parts of a high molecular compound represented by the following basic unit 1 (viscosity average molecular weight: 39,000) in 20 parts of chlorobenzene was subjected to the charge generation. The layer was applied by dip coating and heated at 110 ° C. for 40 minutes to form a 20 μm-thick charge transport layer. The configuration so far is used as a base photoconductor.

[0219]

Embedded image

Example 1 Exemplified Compound (II-3) 10
Part, curable siloxane resin (Shin-Etsu Silicon, X-40-
2239) 18 parts, tin oxide fine particles doped with antimony (T-1, manufactured by Mitsubishi Metal Corporation, primary particle size 0.01 μm) 8
Parts of the mixture in a paint shaker for 5 hours,
The coating solution obtained by adding 7 parts of acetic acid and 0.001 part of 1N hydrochloric acid was dip-coated on the base photoreceptor, and after touch drying for 30 minutes, heat treatment was performed at 120 ° C. for 2 hours. An outermost layer (surface protective layer) having a thickness of about 5 μm was formed. Thus, an electrophotographic photosensitive member of Example 1 was obtained.

[Comparative Example 1] In the photoreceptor of Example 1,
The electrophotographic photoconductor of Comparative Example 1 was obtained without the outermost layer (surface protective layer), that is, the base photoconductor.

[Comparative Example 2] 18 parts of a curable siloxane resin (Shin-Etsu Silicon, X-40-2239), tin oxide fine particles doped with antimony (T-1, manufactured by Mitsubishi Metal Corporation, primary particle size: 0.01 μm) The coating solution obtained by dispersing the mixture of 8 parts with a paint shaker for 5 hours was dip-coated on the base photoreceptor, and after touch drying for 30 minutes, the mixture was dried at 120 ° C.
By performing the heat treatment for a long time, an outermost surface layer (surface protective layer) having a thickness of about 5 μm was formed. Thus, an electrophotographic photosensitive member of Comparative Example 2 was obtained.

The obtained electrophotographic photosensitive members of Example 1 and Comparative Examples 1 and 2 were manufactured using LaserPress manufactured by Fuji Xerox.
4160II and a printing durability test was performed. As the evaluation of the printing durability, the image quality before and after the intermittent printing of 50,000 sheets was evaluated, and the amount of reduction in the thickness of the photoconductor due to abrasion was evaluated. Fuji Xerox PPC paper (L, A4) was used as the paper. The image quality was evaluated using a special evaluator at room temperature and normal humidity (25 ° C./50%) and high temperature and high humidity (2
(8 ° C./85%) environment, 256 gradations and 400 line resolution were evaluated. The results are shown in Table 69.

[0224]

[Table 69]

From Table 69, it was found that the electrophotographic photosensitive member of Example 1 maintained good image quality in any of the environments before and after the printing test. In the electrophotographic photoreceptor of Comparative Example 1, since the film thickness was greatly reduced due to abrasion, the image quality was reduced due to a decrease in print density and partial discharge breakdown was caused. In the electrophotographic photoreceptor of Comparative Example 2, an image was blurred and the resolution was reduced in an initial high temperature and high humidity environment (28 ° C./85%). Further, the evaluation was stopped because the surface protective layer was worn out when the number of sheets exceeded 20,000.

[Examples 2 to 6] In the formation of the outermost surface layer (surface protective layer) of Example 1, (II-13) and (II-3) were used instead of the exemplified compound (II-3).
1), (II-145), (II-249), (II-
Except that 276) was used, the electrophotographic photoreceptors of Examples 2 to 6 were produced in the same manner as in Example 1, and the same evaluation was performed. The results are shown in Table 70.

[0227]

[Table 70]

Example 7 A zirconium compound (trade name: Organotics ZC540, manufactured by Matsumoto Pharmaceutical Co., Ltd.) was formed on a honing-treated aluminum substrate having an outer diameter of 30 mm.
A solution comprising 20 parts, 2.5 parts of a silane compound (trade name: A1100, manufactured by Nippon Unicar), 45 parts of butanol and polyvinyl butyral resin (trade name: Eslec BM-S, manufactured by Sekisui Chemical Co., Ltd.) is applied by a dip coating method. Apply and heat dry at 150 ° C for 10 minutes to form a film thickness of 1.0μ
m undercoat layer was formed.

The Bragg angles (2θ ± 0.2 °) in the X-ray diffraction spectrum were 7.4 °, 16.6 °, 25.
One part of chlorogallium phthalocyanine having a strong diffraction peak at 5 ° and 28.3 ° is mixed with 1 part of polyvinyl butyral (Eslec BM-S, Sekisui Chemical) and 100 parts of n-butyl acetate, and a glass shaker and a paint shaker are mixed. After dispersing by treating for 1 hour, the obtained coating solution was dip-coated on the undercoat layer and dried by heating at 100 ° C. for 10 minutes to form a charge generation layer having a thickness of about 0.15 μm.

2 parts of Exemplified Compound (V-27), 1 part of Exemplified Compound (IV-28), the same high molecular compound (viscosity average molecular weight of 39,000) used for forming the charge transport layer in the base photoreceptor A coating solution obtained by dissolving 3 parts in 24 parts of chlorobenzene is applied on the charge generating layer by dip coating, and heated at 110 ° C. for 40 minutes to form a film having a thickness of 20 μm.
m of the charge transport layer was formed.

The formation of the outermost surface layer (surface protective layer) in Example 1 was carried out in the same manner as in Example 1 except that Exemplified Compound (II-270) was used instead of Exemplified Compound (II-3). An outermost surface layer (surface protective layer) having a thickness of about 5 μm was formed to obtain an electrophotographic photosensitive member of Example 7.

When the same experiment as in Example 1 was conducted on the obtained electrophotographic photosensitive member of Example 7, the abrasion amount was 2.8 μm, and there was no problem in the image quality before and after the printing test.

Example 8 The procedure of Example 7 was repeated except that 0.3 parts of a hindered phenolic antioxidant (Sumilyzer, MDP-S) was added in the formation of the charge transport layer. Formed.

10 parts of the exemplified compound (II-270) and a curable siloxane resin (Shin-Etsu Silicon, X-40-223)
9) 18 parts, hindered phenolic antioxidant (Sumilyzer, MDP-S) 0.5 part, antimony-doped tin oxide fine particles (T-1, manufactured by Mitsubishi Metal Corporation, primary particle size 0.01 μm) 8 Parts of the mixture on a paint shaker
After dispersing for 7 hours, a coating solution obtained by adding 7 parts of acetic acid and 0.001 part of 1N hydrochloric acid was applied onto the charge transport layer by dip coating. Heat treatment was performed to form an outermost surface layer (surface protective layer) having a thickness of about 5 μm. Thus, an electrophotographic photosensitive member of Example 8 was obtained.

The same experiment as in Example 1 was performed on the obtained electrophotographic photosensitive member of Example 8, and as a result, the abrasion loss was 3%.
μm, and there was no problem in image quality before and after the printing test.

Example 9 An electrophotographic photosensitive member of Example 9 was obtained in the same manner as in the electrophotographic photosensitive member of Example 8.

The obtained electrophotographic photosensitive member of Example 9 was mounted on Able 1450 manufactured by Fuji Xerox and evaluated for image quality. As a result, there was no problem in gradation and resolution. 5
The amount of wear after printing 10,000 sheets was 4.5 μm, and there was no abnormality in image quality.

Example 10 An electrophotographic photosensitive member of Example 10 was obtained in the same manner as in the electrophotographic photosensitive member of Example 8, except that the outer diameter of the base material was changed to 60 mm.

The obtained electrophotographic photosensitive member of Example 10 was replaced with
When mounted on an Able 936 manufactured by Fuji Xerox and evaluated for image quality, the color gradation and the 400-line resolution were both good at room temperature, normal humidity, and high temperature and high humidity. After performing 10,000 color prints, the same evaluation was performed, and no problem occurred. As described above, the charging method of Able 936 is not a contact charging method but a scorotron charging method, but could be used without any problem.

Example 11 The electrophotographic photosensitive member of Example 1 was replaced with a LaserPress 4160 manufactured by Fuji Xerox.
The image forming apparatus of the present invention was mounted on a modified II machine and subjected to a printing durability test. This remodeling machine uses an external power supply (Trek's high-voltage power supply 610C, Wavet).
ek waveform generator) and a DC-60
A printing test was performed by applying 0V. From the measurement result of the applied voltage-surface potential measured in advance, no discharge occurred at this applied voltage.

As the evaluation of the printing durability, the image quality was evaluated before and after the intermittent printing of 50,000 sheets, and the reduction in the thickness of the photosensitive member due to abrasion was evaluated. Fuji Xerox PPC paper (L, A4) was used as the paper. The image quality was evaluated using a dedicated evaluator under normal temperature and normal humidity (25 ° C./50%) and high temperature and high humidity (28 ° C./85%) environments with 256 gradations and 4
A 00 line resolution evaluation was performed. The results are shown in Table 71.

[Comparative Example 3] Evaluation was performed in the same manner as in Example 11 using the electrophotographic photosensitive member of Comparative Example 1. Table 7 shows the results
It is shown in FIG.

[0243]

[Table 71]

According to Table 71, in Example 11, good image quality was maintained in both environments before and after the printing durability test. In Comparative Example 3, since the photoconductor did not have the outermost surface layer (surface protective layer) containing the conductive fine particles on the surface, charging with only DC was unstable, and good image quality could be obtained from the beginning. Did not.

[Examples 12 to 16] The electrophotographic photosensitive members of Examples 2 to 6 were evaluated in the same manner as in Example 11. The results are shown in Table 72.

[0246]

[Table 72]

Example 17 When the electrophotographic photoreceptor of Example 7 was evaluated in the same manner as in Example 11, the abrasion was 1.8 μm, and there was no problem in the image quality before and after the printing test. Was.

Example 18 When the electrophotographic photosensitive member of Example 8 was evaluated in the same manner as in Example 11, the abrasion was 2.2 μm, and there was no problem in the image quality before and after the printing test. Was.

Example 19 3 parts of the exemplified compound (A-36) as a charge transporting substance having a hydroxy group, and a burette-modified polyisocyanate solution (solid content 67% by weight) represented by the above structural formula (D) 4 Part, exemplified compound (H-1)
5 parts of bisphenol compound represented by 5), antimony-doped tin oxide fine particles (T-1, manufactured by Mitsubishi Metal Corporation,
5 parts of secondary particle size 0.01 μm) and cyclohexanone 20
Part of the mixture was dispersed with a paint shaker for 5 hours to prepare a coating solution, applied on the base photoreceptor by a spray coating method, dried at room temperature for 10 minutes, and then dried at 150 ° C. for 6 minutes.
By heating for 0 minutes, a 5 μm-thick outermost layer (surface protective layer) was formed. Thus, the electrophotographic photosensitive member of Example 19 was obtained and evaluated in the same manner as in Example 1. The results are shown in Table 73.

[Comparative Example 4] Bisphenol compound (H-
1) 5 parts, 4 parts of a burette-modified polyisocyanate solution represented by the above structural formula (D) (solid content: 67% by weight),
A mixture of 10 parts of antimony-doped tin oxide fine particles (T-1, manufactured by Mitsubishi Metal Corporation, primary particle size: 0.01 μm) and 25 parts of cyclohexanone was mixed with a paint shaker for 5 minutes.
A coating solution was prepared by dispersing the coating solution over time, applied to the base photoreceptor by a spray coating method, dried at room temperature for 10 minutes, and then heated at 150 ° C. for 60 minutes to form a film having a thickness of 5 μm.
Was formed as the outermost layer (surface protective layer). Thus, an electrophotographic photosensitive member of Comparative Example 4 was obtained and evaluated in the same manner as in Example 1. The results are shown in Table 73. The outermost surface layer (surface protective layer) of the electrophotographic photoreceptor of Comparative Example 4 did not contain a charge transporting material, and resistance was controlled only by metal oxide fine particles.

Comparative Example 5 In the formation of the outermost surface layer (surface protective layer) of the electrophotographic photosensitive member of Example 1, the structural formula (D)
The electrophotographic photoreceptor of Comparative Example 5 was obtained in the same manner as in Example 19, except that 4,4′-diphenylmethane diisocyanate having two functional groups was used instead of the burette-modified polyisocyanate solution represented by Evaluation was performed in the same manner as in Example 1. The results are shown in Table 73.

Comparative Example 6 5 parts of the exemplified compound (A-36) as a charge transporting substance having a hydroxy group, and a burette-modified polyisocyanate solution (solid content 67% by weight) represented by the above structural formula (D) 4 And a mixture of 15 parts of cyclohexanone were dispersed in a paint shaker for 5 hours to prepare a coating solution, applied on the base photoreceptor by a spray coating method, dried at room temperature for 10 minutes, and then heated to 150 ° C.
For 60 minutes to form a 5 μm-thick outermost layer (surface protective layer). Thus, an electrophotographic photosensitive member of Comparative Example 6 was obtained, and evaluated in the same manner as in Example 1. The results are shown in Table 73.

[0253]

[Table 73]

According to Table 73, the electrophotographic photoreceptor of Example 19 maintained good image quality in any environment before and after the printing test. Further, in the electrophotographic photoreceptor of Comparative Example 4 in which the outermost surface layer (surface protective layer) does not contain a reactive charge transport material,
From the beginning, image blurring and resolution degradation occurred in a high-temperature and high-humidity environment (28 ° C./85%). In addition, the print density was reduced around 20,000 sheets, and almost no image was obtained when printing 50,000 sheets. Comparative Example 5 using an isocyanate compound having two functional groups for the outermost surface layer (surface protective layer)
In the electrophotographic photoreceptor described above, the amount of wear after printing 50,000 sheets was large, and streak-like scratches occurred frequently on the surface of the photoreceptor, which appeared as image defects. The electrophotographic photoreceptor of Comparative Example 6, which does not contain conductive fine particles in the outermost surface layer (surface protective layer) and has a high content ratio of the charge transport material, has good initial image quality in any environment, but prints 50,000 sheets. After high temperature and high humidity environment (28 ℃
/ 85%), the image was blurred and the resolution was reduced, which is considered to be caused by the deterioration of the charge transport material due to the discharge product.

[Examples 20 and 21] In forming the outermost surface layer (surface protective layer) of the electrophotographic photosensitive member of Example 19, each of the exemplified compound (B-7) was used instead of the exemplified compound (A-36). ) And the electrophotographic photoreceptors of Examples 20 and 21 were obtained in the same manner as in Example 19 except for using the exemplified compound (C-15), and evaluated in the same manner as in Example 1. Table 7 shows the results
It is shown in FIG.

Example 22 In the outermost surface layer (surface protective layer) of the electrophotographic photosensitive member of Example 19, a burette-modified polyisocyanate solution (solid content: 67% by weight) represented by the structural formula (D) was prepared. Instead of using the isocyanurate-modified polyisocyanate solution (solid content 75% by weight) represented by the structural formula (E), the same procedure as in Example 19 was carried out.
The electrophotographic photoreceptor of Example 22 was obtained and evaluated in the same manner as in Example 1. The results are shown in Table 74.

[0257]

[Table 74]

Example 23 An undercoat layer, a charge generation layer and a charge transport layer were sequentially formed on a conductive support in the same manner as in the electrophotographic photoreceptor of Example 7. Next, in forming the outermost surface layer (surface protective layer) of the electrophotographic photoreceptor of Example 19, the exemplary compound (A-2) was used instead of the exemplary compound (A-36).
A film thickness of about 5 μm was obtained in the same manner as in Example 19 except that 2) was used.
m of the outermost layer (surface protective layer) was formed. Thus, the electrophotographic photosensitive member of Example 23 was obtained and evaluated in the same manner as in Example 1. As a result, the abrasion amount was 1.5 μm, and there was no problem in the image quality before and after the printing test.

Example 24 A charge transport layer was formed in the same manner as in Example 8.

3 parts of the exemplified compound (A-36), 4 parts of the burette-modified polyisocyanate solution (solid content: 67% by weight) represented by the structural formula (D), and the exemplified compound (H-1)
2) bisphenol compound represented by 5), hindered phenolic antioxidant (Sumilyzer, MDP-S)
0.5 parts, tin oxide fine particles doped with antimony (T-
1. A mixture of 5 parts of Mitsubishi Metal Corporation (primary particle size: 0.01 μm) and 20 parts of cyclohexanone was dispersed in a paint shaker for 5 hours to prepare a coating solution, and spray-coated on the charge transport layer by a spray coating method. After coating, drying at room temperature for 10 minutes, and heating at 150 ° C. for 60 minutes, a film thickness of 5 μm
m of the outermost layer (surface protective layer) was formed. Thus, the electrophotographic photosensitive member of Example 24 was obtained and evaluated in the same manner as in Example 1. As a result, the abrasion amount was 1.8 μm, and there was no problem in the image quality before and after the printing test.

Example 25 An electrophotographic photosensitive member of Example 25 was obtained in the same manner as in the electrophotographic photosensitive member of Example 24.

The obtained electrophotographic photosensitive member of Example 25 was replaced with
When the image quality was evaluated by attaching the device to Able 1450 manufactured by Fuji Xerox, there was no problem in both gradation and resolution.
The amount of wear after printing 50,000 sheets was 2.2 μm, and there was no abnormality in image quality.

Example 26 An electrophotographic photosensitive member of Example 26 was obtained in the same manner as in Example 24, except that the outer diameter of the base material was changed to 84 mm.

The obtained electrophotographic photosensitive member of Example 26 was replaced with
When mounted on an Able 936 manufactured by Fuji Xerox and evaluated for image quality, the color gradation and the 400-line resolution were both good at room temperature, normal humidity, and high temperature and high humidity. After performing 10,000 color prints, the same evaluation was performed, and no problem occurred.

Example 27 Using the electrophotographic photosensitive member of Example 19, evaluation was made in the same manner as in Example 11. The results are shown in Table 75.

[0266]

[Table 75]

As shown in Table 75, in Example 1, good image quality was maintained in any environment before and after the printing test.

[Examples 28 and 29] The electrophotographic photosensitive members of Examples 20 and 21 were evaluated in the same manner as in Example 11. The results are shown in Table 76.

Example 30 Using the electrophotographic photosensitive member of Example 22, evaluation was made in the same manner as in Example 11. The results are shown in Table 76.

[0270]

[Table 76]

Example 31 Using the electrophotographic photosensitive member of Example 23, evaluation was made in the same manner as in Example 11.
The abrasion amount was 1.0 μm, and there was no problem in the image quality before and after the printing test.

Example 32 Using the electrophotographic photosensitive member of Example 24, evaluation was made in the same manner as in Example 11.
The abrasion amount was 1.2 μm, and there was no problem in image quality before and after the printing test.

According to Examples and Comparative Examples, the electrophotographic photoreceptor of the present invention comprises a compound represented by the general formula (I) or a compound represented by the general formulas (A) to (C) having photoelectric properties. It has a three-dimensionally cross-linked and cured film structure, and further has a structure in which conductive fine particles are dispersed, thereby achieving strong mechanical strength while having photoelectric characteristics. Therefore, it has high durability when used as an electrophotographic image forming apparatus, and has the effect of suppressing the printing running cost. In particular, when used in conjunction with an electrophotographic image forming apparatus that employs a contact charging method that exerts a large stress on the photoreceptor, especially a contact charging method that has an AC component, the effect is significant.

[0274]

As described above, the present invention can provide an electrophotographic photosensitive member excellent in environmental resistance, durability, and photoelectric characteristics, and an image forming apparatus having the same.

[Brief description of the drawings]

FIG. 1 is an enlarged sectional view showing an example of an electrophotographic photoconductor of the present invention.

FIG. 2 is an enlarged sectional view showing an example of the electrophotographic photoreceptor of the present invention.

FIG. 3 is an enlarged sectional view showing an example of the electrophotographic photoreceptor of the present invention.

FIG. 4 is a schematic configuration diagram illustrating an example of an image forming apparatus of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 10 photoconductor 12 charging roll 14 laser exposure optical system 16 developing device 18 transfer roll 20 cleaning blade 22 fixing roll

 ────────────────────────────────────────────────── ─── Continued on the front page (72) Inventor Fumio Kojima 1600 Takematsu, Minamiashigara-shi, Kanagawa Prefecture Fuji Xerox Co., Ltd. F-term (reference) 2H068 AA02 AA03 AA04 AA05 BA12 BA14 BA58 BB29 BB57 FA03 FA07 FC01

Claims (4)

[Claims] 1. An electrophotographic photoreceptor comprising conductive fine particles and having at least an outermost surface layer comprising a cured film formed of a reactive charge transporting material. 2. The electrophotographic photoconductor according to claim 1, wherein the cured film is a cured film formed by at least a compound represented by the following general formula (1). Embedded image In the general formula (I), F represents an organic group derived from a photofunctional compound. D represents a flexible subunit. A represents a substituted silicon group having a hydrolyzable group represented by -Si (R ₁ ) _(3-a) (OR ₂ ) _a (where R ₁ is a hydrogen, an alkyl group, a substituted or unsubstituted Represents an aryl group.
₂ represents hydrogen, an alkyl group, or a trialkylsilyl group.
a represents an integer of 1 to 3. ). b represents an integer of 1 to 4. 3. The electrophotography according to claim 1, wherein the cured film is a cured film formed of a charge transporting material having at least a hydroxy group and an isocyanate compound having three or more functional groups. Photoconductor. 4. An image forming apparatus comprising at least an electrophotographic photosensitive member and a charging means therefor, wherein said electrophotographic photosensitive member is the electrophotographic photosensitive member according to claim 1, wherein An image forming apparatus, wherein the means is a contact charging system.