JP2000206718A - Electrophotographic photoreceptor and process cartridge and electrophotographic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor superior in film strength, resistances to deposition and abrasion and scratching, by including in a photosensitive layer a compound obtained by polymerizing a hole transfer compound having more than two chain-polymerizable functional groups in the same molecule by heat or ultraviolet rays. SOLUTION: The photosensitive layer of this photoreceptor contains a compound obtained by heat- or ultraviolet-polymerizing a hole transfer compound having >=2 chain-polymerizable functional groups in the same molecule represented by formula I in which A is a hole transfer group; each of P1 and P2 is, independently, a chain-polymerizable functional group; Z is an optionally substituted organic group; each of (a), (b), and (d) is 0 or an integer of >=1, a+b×d>=2, and when a>=2, each of plural P1 may be the same or different, when d>=2, each of plural P2 may be the same or different, and when b>=2, each of Z and P2 may be the same or different. The hole transfer compound obtained by substituting the sites combining A and P1 and Z for H atoms is represented by a condensed cyclic hydrocarbon or a condensed heterocycle or formulae II or III.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photoreceptor,
More particularly, the present invention relates to an electrophotographic photoreceptor having a surface layer containing a specific resin, a process cartridge having the electrophotographic photoreceptor, and an electrophotographic apparatus.

[0002]

2. Description of the Related Art Conventionally, inorganic materials such as selenium, cadmium sulfide and zinc oxide have been known as photoconductive materials used for electrophotographic photosensitive members. On the other hand, organic materials such as polyvinyl carbazole, phthalocyanine, and azo pigments are noted for their advantages such as high productivity and no pollution, and they tend to be inferior in terms of photoconductive properties and durability as compared with inorganic materials. , Has become widely used.

These electrophotographic photoconductors are often used as function-separated electrophotographic photoconductors in which a charge generation layer and a charge transport layer are stacked in order to satisfy both electrical and mechanical properties. On the other hand, as a matter of course, the electrophotographic photosensitive member is required to have sensitivity, electric characteristics, optical characteristics, and durability characteristics according to the electrophotographic process to be applied.

Particularly, in the case of an electrophotographic photosensitive member that is used repeatedly, an external electrical or mechanical force such as charging, image exposure, toner development, transfer to paper, and cleaning is directly applied to the surface of the electrophotographic photosensitive member. Therefore, durability for them is required. Specifically, durability against abrasion and scratches on the surface due to rubbing is required, and durability against surface deterioration due to charging is also required.

Generally, the surface of an electrophotographic photosensitive member is a thin resin layer, and the characteristics of the resin are very important. In recent years, acrylic resins, polycarbonate resins, and the like have been put to practical use as resins that satisfy the above-mentioned conditions to some extent. However, not all of the above-described characteristics are satisfied by these resins, and in particular, electrophotographic photoreceptors It is difficult to say that the film hardness of the resin is sufficiently high for achieving high durability. Even when these resins are used as a resin for forming a surface layer, there is a problem in that the surface layer is worn and the flaw is further generated during repeated use.

Further, in recent years, low-molecular-weight compounds such as charge-transporting materials are often added in relatively large amounts due to demands for higher sensitivity of organic electrophotographic photoreceptors. In this case, these low-molecular-weight materials are used as plasticizers. Due to the unusual effect, the film strength is remarkably reduced, and abrasion and scratching of the surface layer at the time of further repeated use are problematic. Further, when the electrophotographic photoreceptor is stored for a long period of time, the above-mentioned low molecular weight component is precipitated, and there is a problem that the layers are separated.

As a means for solving these problems, an attempt to use a curable resin as a resin for the charge transport layer has been made.
For example, it is disclosed in JP-A-2-127652. As described above, by using a curable resin as the resin for the charge transport layer and curing and cross-linking the charge transport layer, the mechanical strength is increased, and the abrasion resistance and scratch resistance during repeated use are greatly improved. However, even if a curable resin is used, the low molecular weight component functions as a plasticizer in the binder resin to the last, so that the above-mentioned problems of precipitation and layer separation have not been fundamentally solved.

In a charge transport layer composed of an organic charge transport material and a binder resin, the charge transport ability greatly depends on the resin. For example, a curable resin having sufficiently high hardness has insufficient charge transport ability. However, there is no increase in the residual potential upon repeated use, and both have not been satisfied. In JP-A-5-216249 and JP-A-7-72640, a charge transporting layer contains a monomer having a carbon-carbon double bond, and a carbon-carbon double bond of the charge transporting material and a heat-transferring material. Alternatively, an electrophotographic photoreceptor in which a charge transport layer cured film is formed by reacting with light energy is disclosed, but the charge transport material is merely fixed in a pendant shape to the polymer main skeleton, and the plasticity of the plastic is reduced. Mechanical action cannot be sufficiently eliminated, so that the mechanical strength is not sufficient. In addition, when the concentration of the charge transporting material is increased to improve the charge transporting ability, the crosslink density becomes low and sufficient mechanical strength cannot be secured.

Another solution is disclosed in, for example,
JP-A-248649 discloses an electrophotographic photoreceptor having a charge transport layer formed by introducing a group having a charge transport ability into a thermoplastic polymer main chain. It has an effect on precipitation and layer separation compared to the transport layer, and improves mechanical strength, but it is a thermoplastic resin to the last, its mechanical strength is limited, including the solubility of the resin It is hard to say that handling and productivity are sufficient. As described above, the conventional system has not achieved both high mechanical strength and charge transport ability.

[0010]

SUMMARY OF THE INVENTION An object of the present invention is to solve the problems of a conventional electrophotographic photosensitive member using a resin as a surface layer, and to improve the abrasion resistance by increasing the film strength. Another object of the present invention is to provide an electrophotographic photoreceptor having improved scratch resistance and good deposition resistance.

Another object of the present invention is to provide an electrophotographic apparatus capable of exhibiting stable performance even when repeatedly used, with very little change or deterioration in electrophotographic photosensitive member characteristics such as an increase in residual potential upon repeated use. It is to provide a photoreceptor.

Still another object of the present invention is to improve the abrasion resistance and scratch resistance of the surface layer of an electrophotographic photosensitive member, to provide a long-life, high-quality electrophotographic photosensitive member, and to provide a process cartridge having the electrophotographic photosensitive member. And an electrophotographic apparatus.

[0013]

According to the present invention, there is provided an electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer has two or more photosensitive molecules in the same molecule represented by the following general formula (1). An electrophotographic photosensitive member containing a compound obtained by polymerizing a hole transporting compound having a chain polymerizable functional group by heat or ultraviolet, a process cartridge having the electrophotographic photosensitive member, and an electrophotographic apparatus are provided.

[0014]

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In the formula, A represents a hole transporting group. P ¹ and P ² represent a chain polymerizable functional group. P ¹ and P ² may be the same or different. Z represents an organic residue which may have a substituent. a, b and d each represent 0 or an integer of 1 or more, and a + b
Xd represents an integer of 2 or more. When a is 2 or more, P
¹ may be the same or different; when d is 2 or more, P ² may be the same or different; and when b is 2 or more, Z and P ² may be the same or different.

[0016]

Embodiments of the present invention will be described below in detail.

First, the chain polymerizable functional group in the present invention will be described. The term chain polymerization in the present invention refers to the former type of polymerization reaction when the formation reaction of a polymer is largely divided into chain polymerization and sequential polymerization.For example, for example, Gihodo Shuppan Tadahiro Miwa's `` Basic synthetic resin chemistry '' (New edition) 1
July 25, 995 (1st edition, 8th press) As described in 24, the form mainly refers to unsaturated polymerization, ring-opening polymerization, isomerization polymerization and the like in which the reaction proceeds mainly through intermediates such as radicals or ions.

The chain-polymerizable functional groups P ¹ and P ² in the general formula (1) mean functional groups capable of the above-mentioned reaction mode, and here, they occupy most of them, and have a wide range of application. Alternatively, specific examples of the ring-opening polymerizable functional group are shown.

Unsaturated polymerization refers to an unsaturated group such as CＣC, C≡C, C ＝ O, C ＝
This is a reaction in which N, C≡N and the like are polymerized, and mainly CＣC. Specific examples of the unsaturated polymerizable functional group are shown in Table 1, but are not limited thereto.

[0020]

[Table 1]

In the table, R represents an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aralkyl group such as a benzyl group and a phenethyl group which may have a substituent, and a substituent. An aryl group such as a phenyl group, a naphthyl group and an anthryl group or a hydrogen atom which may be possessed.

Ring-opening polymerization is a process in which an unstable cyclic structure having a strain, such as a carbon ring, an oxo ring, or a nitrogen heterocycle, is activated by the action of a catalyst. Is generated, but in this case, most of the ions basically act as active species.
Specific examples of the ring-opening polymerizable functional group are shown in Table 2, but are not limited thereto.

[0023]

[Table 2]

In the table, R represents an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aralkyl group such as a benzyl group and a phenethyl group which may have a substituent, and a substituent. An aryl group such as a phenyl group, a naphthyl group and an anthryl group or a hydrogen atom which may be possessed.

Among the chain polymerizable functional groups according to the present invention as described above, the following general formulas (8) to (10)
Are preferred.

[0026]

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In the formula, E is a hydrogen atom, a halogen atom such as fluorine, chlorine and bromine, a methyl group which may have a substituent,
Alkyl group such as ethyl group, propyl group and butyl group, benzyl group which may have a substituent, aralkyl group such as phenethyl group, naphthylmethyl group, furfuryl group and thienyl group, and phenyl which may have a substituent; Group, naphthyl group,
Aryl groups such as anthryl group, pyrenyl group, thiophenyl group and furyl group, alkoxy groups such as CN group, nitro group, methoxy group, ethoxy group and propoxy group, -COO
R ¹³ or —CONR ¹⁴ R ¹⁵ is shown.

W is an arylene group such as a divalent phenylene group, a naphthylene group or an anthracenylene group which may have a substituent, or a divalent group such as a methylene group, an ethylene group or a butylene group which may have a substituent. Alkylene group, -COO-,
-O -, - OO -, - represented by S- or -CONR ^16.

Here, R ^{13 to} R ¹⁶ have a hydrogen atom, a halogen atom such as fluorine, chlorine and bromine, an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, and a substituent. R ¹⁴ and R ¹⁴ represent an aralkyl group such as a benzyl group and a phenethyl group or an aryl group such as a phenyl group, a naphthyl group and an anthryl group which may have a substituent;
¹⁵ may be the same or different from each other. F indicates 0 or 1.

The substituents which may be present in E and W include halogen atoms such as fluorine, chlorine, bromine and iodine;
Or a nitro group or a cyano group or a hydroxyl group; or a methyl group,
Alkyl groups such as ethyl group, propyl group and butyl group; or alkoxy groups such as methoxy group, ethoxy group and propoxy group; or aryloxy groups such as phenoxy group and naphthoxy group; or benzyl group, phenethyl group, naphthylmethyl group, Aralkyl groups such as furfuryl group and thienyl group; or aryl groups such as phenyl group, naphthyl group, anthryl group and pyrenyl group.

[0031]

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In the formula, R ¹⁷ and R ¹⁸ represent a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, a propyl group and an butyl group which may have a substituent, a benzyl group which may have a substituent and It represents an aralkyl group such as a phenethyl group or an aryl group such as a phenyl group and a naphthyl group which may have a substituent, and n represents an integer of 1 to 10.

[0033]

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In the formula, R ¹⁹ and R ²⁰ are a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group which may have a substituent; a benzyl group which may have a substituent; It represents an aralkyl group such as a phenethyl group or an aryl group such as a phenyl group and a naphthyl group which may have a substituent, and n represents 0 or an integer of 1 to 10.

The above general formulas (9) and (1)
Examples of the substituent which R ^{17 to} R ^{20 in} 0) may have include a halogen atom such as fluorine, chlorine, bromine and iodine; or an alkyl group such as methyl, ethyl, propyl and butyl; Or alkoxy groups such as ethoxy and propoxy groups; or aryloxy groups such as phenoxy and naphthoxy groups; or aralkyl groups such as benzyl, phenethyl, naphthylmethyl, furfuryl and thienyl; or phenyl and naphthyl And aryl groups such as anthryl group and pyrenyl group.

Further, among the above general formulas (8) to (10), more particularly preferred chain polymerizable functional groups include those represented by the following general formulas (11) to (17).

[0037]

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In the present invention, "a hole-transporting compound having a chain-polymerizable functional group" means that the above-described chain-polymerizable group is chemically bonded to the above-described hole-transporting compound by two or more functional groups. Are shown. In this case, all of the chain polymerizable functional groups may be the same or different. The hole transporting compound having two or more of these chain polymerizable functional groups is represented by the general formula (1).

In the general formula (1), when "a is 2 or more, P¹
May be the same or different. "
Of chain polymerizable functional groups¹¹, P¹², P¹³, P¹⁴, P¹⁵
.... P¹ⁿ, For example, when a = 3, hole transport
Chain polymerizable functional group P directly bonded to transportable compound A¹Is 3
Two things are the same, but two are the same and one is different (for example,
If P¹¹And P¹¹And P¹²But all three are different
(For example, P ¹²And P¹⁵And P¹⁷Or)
(“D is 2 or more, P
^TwoMay be the same or different. "
In the case above, Z and P^TwoMay be the same or different. "
This means the same thing.)

A in the above formula (1) represents a hole transporting group, and the hydrogenated compound (hole transporting compound) in which the bonding site with P ¹ or Z is replaced by a hydrogen atom has a substituent. Naphthalene, anthracene, phenanthrene,
Pyrene, fluorene, fluorancene, azulene, indene, perylene, chrysene and benzofuran which may have a substituent such as coronene or a substituent, indole, carbazole, benzcarbazole, acridine,
Examples include condensed complex rings such as phenothiazine and quinoline, or the following general formulas (2) and (4). Among them, those represented by the general formulas (2) and (4) are preferable.

[0041]

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However, the condensed ring hydrocarbon, the condensed complex ring and the general formula (2) have at least one group represented by the following general formula (3).

[0043]

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In the above general formulas (2) and (3), Ar ¹ and Ar ^{2 each} represent an optionally substituted phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl group, furyl group, A pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, a dibenzofuryl group, or an aryl group such as a dibenzothiophenyl group; R ¹ and R ^{2 each} have a substituent; Alkyl groups having 10 or less carbon atoms such as methyl group, ethyl group, propyl group and butyl group, and aralkyl groups such as benzyl group, phenethyl group, naphthylmethyl group, furfuryl group and thienyl group which may have a substituent. Group, phenyl group which may have a substituent, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl Group, a furyl group, a pyridyl group, a quinolyl group, a benzoquinolyl group, a carbazolyl group, a phenothiazinyl group, a benzofuryl group, a benzothiophenyl group, an aryl group such as a dibenzofuryl group and a dibenzothiophenyl group, R ³ and R ⁴ These alkyl groups,
A hydrogen atom is shown in addition to the aralkyl group and the aryl group.
Note that R ¹ and R ² and R ³ and R ⁴ may be the same or different.

Among them, it is preferable that R ⁴ is an aryl group, and the hole transporting group is represented by the general formula (2)
^It is particularly preferred that ¹ and R ² are aryl groups. Also,
Any two of R ¹ or R ² or Ar ¹ , or Ar ² and R ⁴ may be bonded directly or via a bonding group, and the bonding group includes a methylene group, an ethylene group and a propylene group. And the like, a hetero atom such as an oxygen and sulfur atom, or a CH ＝ CH group. n ¹ is an integer of 0 or 1.

[0046]

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In the general formula (4), the general formula (4)
The compound represented by has at least one group represented by the following general formula (5).

[0048]

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In the above general formulas (4) and (5), Ar ³ ,
Ar ⁴ and Ar ⁵ are a phenyl group which may have a substituent,
Naphthyl, anthryl, phenanthryl, pyrenyl, thiophenyl, furyl, pyridyl, quinolyl, benzoquinolyl, carbazolyl, phenothiazinyl, benzofuryl, benzothiophenyl, dibenzofuryl and dibenzothiophenyl R ⁵ is an alkyl group having 10 or less carbon atoms such as a methyl group, an ethyl group, a propyl group and a butyl group which may have a substituent, a benzyl group which may have a substituent, Aralkyl groups such as phenethyl group, naphthylmethyl group, furfuryl group and thienyl group, phenyl group which may have a substituent, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, thiophenyl group, furyl group, pyridyl group, quinolyl Group, benzoquinolyl group, carbazolyl group, phenothiazinyl group, ben Furyl group, a benzothiophenyl group, an aryl group such as a dibenzofuryl group and a dibenzothiophenyl group, R ⁶ and R ⁷ are the alkyl groups,
A hydrogen atom is shown in addition to the aralkyl group and the aryl group.
Note that Ar ³ and Ar ⁴ and R ⁶ and R ⁷ may be the same or different.

Further, among them, it is particularly preferable that R ⁵ and R ⁷ are aryl groups. R ⁵ or Ar ³ or A
Any two of r ⁴ , or Ar ⁵ and R ⁷ may be bonded directly or via a bonding group. Examples of the bonding group include a methylene group, an alkylene group such as an ethylene group and a propylene group, and an oxygen group. And a hetero atom such as a sulfur atom or a CH = CH group. n ² represents 0 or an integer of 1 to 2, and is preferably 1 or 2.

In the general formula (1), Z is an alkylene group which may have a substituent, an arylene group which may have a substituent, CR ⁸ ＣＲCR ⁹ (R ⁸ and R ⁹ are Alkyl group,
An aryl group or a hydrogen atom, R ⁸ and R ⁹ may be the same or different), C ＝ O, S ＝ O, SO ₂ , an organic residue which is one or any combination of oxygen atom or sulfur atom Is shown. Among them, a compound represented by the following general formula (6) is preferable, and a compound represented by the following general formula (7) is particularly preferable.

[0052]

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[0053]

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In the above general formula (6), X ^{1 to} X ³ represent an optionally substituted alkylene group having 20 or less carbon atoms such as a methylene group, an ethylene group and a propylene group, and (CR ¹⁰ C
R ¹¹ ) _m , C ＝ O, S ＝ O, SO ₂ , an oxygen atom or a sulfur atom, and Ar ⁶ and Ar ⁷ are optionally substituted arylene groups (benzene, naphthalene, anthracene, phenanthrene, pyrene , Thiophene, pyridine, quinoline, benzoquinoline, carbazole, phenothiazine,
Benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, etc., from which two hydrogen atoms have been removed). R ¹⁰ and R ¹¹ are an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aryl group such as a phenyl group, a naphthyl group and a thiophenyl group which may have a substituent, or a hydrogen atom. And R ¹⁰ and R ¹¹
May be the same or different. m is an integer of 1 to 5, p to t
Represents 0 or an integer of 1 to 10 (where p to t are simultaneously 0
Is not.)

In the general formula (7), X ⁴ and X ⁵ represent (CH
₂ ) _g , (CH ＝ CR ¹² ) _h , C ＝ O or an oxygen atom, and Ar ⁵ is an arylene group which may have a substituent (benzene, naphthalene, anthracene, phenanthrene, pyrene, thiophene, pyridine, A group obtained by removing two hydrogen atoms from quinoline, benzoquinoline, carbazole, phenothiazine, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, and the like. R ¹²
Represents an alkyl group such as a methyl group, an ethyl group and a propyl group which may have a substituent, an aryl group such as a phenyl group, a naphthyl group and a thiophenyl group which may have a substituent, or a hydrogen atom. g is an integer of 1 to 10, h is an integer of 1 to 5, u to w is an integer of 0 or 1 to 10 (particularly preferably 0 or an integer of 1 to 5; It cannot be 0).

It should be noted that R ^{1 in the} above general formulas (1) to (7)
-R ¹² , Ar ¹ -Ar ⁸ , X ¹ -X ⁵ and Z may each have a substituent such as a halogen atom such as fluorine, chlorine, bromine and iodine; or a nitro group or a cyano group or a hydroxyl group; Or an alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group; or an alkoxy group such as a methoxy group, an ethoxy group and a propoxy group; or an aryloxy group such as a phenoxy group and a naphthoxy group; or a benzyl group or a phenethyl group; Aralkyl groups such as naphthylmethyl group, furfuryl group and thienyl group; or aryl groups such as phenyl group, naphthyl group, anthryl group and pyrenyl group; or dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group and di ( substituted amino groups such as p-tolyl) amino groups; or aryls such as styryl groups and naphthylvinyl groups Although vinyl group and the like, is preferably non-substituted amino group.

The hole transporting compound having two or more chain polymerizable functional groups in the same molecule according to the present invention preferably has an oxidation potential of 1.2 (V) or less.
More preferably, it is 4 to 1.2 (V). that is,
When the oxidation potential exceeds 1.2 (V), injection of charges (holes) from the charge generation material is unlikely to occur, and problems such as an increase in residual potential, deterioration in sensitivity, and an increase in potential fluctuation during repeated use tend to occur. If it is less than 0.4 (V), the compound itself is easily oxidized and deteriorates easily, in addition to problems such as a decrease in charging ability and the like, resulting in deterioration of sensitivity, image blur and potential fluctuation during repeated use. This is because problems such as an increase in size are likely to occur.

The oxidation potential described here is measured by the following method.

(Measurement method of oxidation potential) A saturated calomel electrode was used as a reference electrode, and 0.1 N (n-Bu) ₄ N ⁺ ClO was used as an electrolyte.
_{Using a 4} ^- acetonitrile solution, sweep the potential applied to the working electrode (platinum) with a potential sweeper,
The potential when the obtained current-potential curve showed a peak was defined as the oxidation potential. In detail, the sample is 0.1N (n-B
^{_{u) 4 N + ClO 4 -}} 5~10mmo in acetonitrile solution
Dissolve to a concentration of about 1%. Then, a voltage is applied to this sample solution by a working electrode, and a current change when the voltage is linearly changed from a low potential (0 V) to a high potential (+1.5 V) is measured to obtain a current-potential curve. In this current-potential curve, the potential at the peak top when the current value showed a peak (the first peak when there were a plurality of peaks) was defined as the oxidation potential.

Further, the hole transporting compound having a chain polymerizable functional group has a hole transporting ability of 1 × 10 ⁻⁷ (cm ^2).
/ V. sec) or more having a drift mobility of not less than (sec.) (provided electric field: 5 × 10 ⁴ V / cm).
If the density is less than 1 × 10 ⁻⁷ (cm ² /V.sec), there is a problem that, as an electrophotographic photoreceptor, holes cannot move sufficiently before development after exposure, sensitivity is apparently reduced and residual potential is increased. May occur.

The following are typical examples of the hole transporting compound having a chain polymerizable functional group according to the present invention, but the invention is not limited thereto.

[0062]

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[0063]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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In the present invention, a typical method for synthesizing a hole transporting compound having a chain polymerizable functional group will be described below.

(Synthesis Example 1: Synthesis of Compound No. 1-13) The compound was synthesized according to the following route.

[0089]

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1 (50 g: 0.173 mol), 2
(7.5 g: 81 mmol), anhydrous potassium carbonate (4
7.8 g) and copper powder (55 g) together with 200 g of 1,2-dichlorobenzene were heated and stirred at 180 to 190 ° C. for 10 minutes.
Time went. After filtering the reaction solution, the solvent was removed under reduced pressure,
The residue was purified using a silica gel column to give 58 g of 3
Obtained.

N, N-dimethylformamide (DM
F) After cooling 35 g to 0-5 ° C, the phosphorous oxychloride (1
(8.4 g: 0.12 mol) was slowly added dropwise so as not to exceed 10 ° C. After completion of the dropwise addition, the mixture was stirred for 15 minutes and then 3 (50.0 g: 0.12 mol) / DMF 50 g
The solution was slowly dropped. After completion of the dropwise addition, the mixture is stirred for 30 minutes, returned to room temperature, stirred for 1 hour, and further heated to 80 to 85 ° C.
And stirred for 5 hours. The reaction solution was poured into about 15% aqueous sodium acetate solution (800 g) and stirred for 12 hours. After neutralizing it, extraction was performed using toluene, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified by column using a silica gel column to obtain 37.8 g of 4.

4 (25 g: 56 mmol) was added to 200 ml of ethanol, and 1,1-diphenylhydrazine hydrochloride (35 g: 159 mmol) was added thereto. After completion of the addition, the mixture was stirred at room temperature for 1 hour, and then stirred at 50 ° C for 2 hours.
Heating and stirring were performed for hours. After cooling, the reaction solution was poured into water and extracted with toluene. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified with a silica gel column to give 24.5 g of 5.

5 (20 g: 33 mmol) was added to 200 g of methylcellosolve, and sodium methylate (12.0 g) was slowly added with stirring at room temperature. After completion of the addition, the mixture was stirred at room temperature for 1 hour, and further heated and stirred at 40 to 50 ° C. for 8 hours. The reaction solution was poured into water, neutralized with dilute hydrochloric acid, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column using a silica gel column to obtain 7.1 g of 6.

6 (7.0 g: 11 mmol) and triethylamine (3.5 g: 35 mmol) were added to 100 ml of dry tetrahydrofuran (THF), cooled to 0-5 ° C., and acryloyl chloride (2.5 g: 28 mmol) was slowly added dropwise. did. After completion of the dropwise addition, the temperature was slowly returned to room temperature, and the mixture was stirred at room temperature for 4 hours. The reaction solution was poured into water, neutralized, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified with a silica gel column to give 2.8 g of 7 (Compound No. 1-13) (oxidation potential: 0.69 V).

(Synthesis Example 2: Synthesis of Compound No. 2-1)
Synthesized according to the following route.

[0096]

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1 (50 g: 0.173 mol), 2
(8.0 g: 86 mmol), anhydrous potassium carbonate (4
7.8 g) and copper powder (55 g) together with 200 g of 1,2-dichlorobenzene at 180 to 190 ° C. and stirred for 13 minutes.
Time went. After filtering the reaction solution, the solvent was removed under reduced pressure,
The residue was recrystallized twice with an acetone / methanol mixed solvent to obtain 3 (51 g).

After cooling 35 g of DMF to 0 to 5 ° C., phosphorus oxychloride (18.4 g: 0.12 mol) was slowly added dropwise so as not to exceed 10 ° C. After completion of the dropwise addition, the mixture was stirred for 15 minutes and then 3 (50.0 g: 0.12 mol) / DMF
A 50 g solution was slowly added dropwise. 3 after the end of dropping
After stirring for 0 minutes, return to room temperature, stir for 1 hour, and further at 80-85 ° C.
And stirred for 5 hours. The reaction solution was poured into about 15% aqueous sodium acetate solution (800 g) and stirred for 12 hours. After neutralizing it, extraction was performed using toluene, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified by column using a silica gel column to obtain 37.8 g of 4.

4 (30 g: 67 mmol) and 1,1-
Diphenylmethyldiethyl phosphate (20.5
g: 67 mmol) in 200 ml of dry THF.
At room temperature, oily sodium hydride (about 60%: 2.9)
7 g: about 74 mmol) was added slowly. After completion of the addition, the mixture was stirred at room temperature for 30 minutes and then heated and stirred for 3 hours. After cooling, the reaction solution was poured into water and extracted with toluene. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was subjected to column purification using a silica gel column.
1.1 g were obtained.

5 (20 g: 33.6 mmol) was added to 200 g of methylcellosolve, and sodium methylate (7.0 g) was slowly added with stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for 1 hour and then further heated to 70 to 80 ° C.
For 12 hours. The reaction solution was poured into water, neutralized with dilute hydrochloric acid, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with a silica gel column to give 15.1 g of 6.

6 (15 g: 29.3 mmol) and triethylamine (8.88 g: 87.9 mmol)
Was added to 100 ml of dry THF, cooled to 0 to 5 ° C., and acryloyl chloride (8.0 g: 88.4 mmol) was slowly added dropwise. After completion of the dropwise addition, the temperature was slowly returned to room temperature, and the mixture was stirred at room temperature for 6 hours. The reaction solution was poured into water, neutralized, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was subjected to column purification using a silica gel column to give 7 (Compound No. 2-1) as 9.8.
g (oxidation potential: 0.76 V).

(Synthesis Example 3: Synthesis of Compound No. 2-34) The compound was synthesized according to the following route.

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1 (50 g: 0.173 mol), 8 (3
1.7 g: 0.173 mol), anhydrous potassium carbonate (5
0 g) and copper powder (65 g) were heated and stirred at 180 to 190 ° C. for 10 hours together with 250 g of 1,2-dichlorobenzene. After filtering the reaction solution, the solvent was removed under reduced pressure, and the residue was subjected to column purification using a silica gel column to give 9 to 49.
g was obtained.

After cooling 40 g of DMF to 0 to 5 ° C., phosphorus oxychloride (19.9 g: 0.13 mol) was slowly added dropwise so as not to exceed 10 ° C. After completion of the dropwise addition, the mixture was stirred for 15 minutes and then 9 (45 g: 0.013 mol) / D
A MF 60 g solution was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred for 30 minutes, returned to room temperature, stirred for 1 hour, further heated to 80 to 85 ° C, and stirred for 5 hours. The reaction solution was poured into 1 kg of an aqueous solution of about 15% sodium acetate and stirred for 12 hours. After neutralizing it, extraction was performed using toluene, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the residue was subjected to column purification using a silica gel column to obtain 10-33.
g was obtained.

10 (30 g: 80 mmol) and 1-phenyl-1- (p-methoxyphenyl) methyldiethyl phosphate (27 g: 80.7 mmol) were dried in dry T
It was dissolved in 200 ml of HF, and oily sodium hydride (about 60%: 3.8 g: about 95 mmol) was slowly added thereto at room temperature. After stirring for 30 minutes at room temperature after the end of the addition,
Heating and stirring were performed for 3 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified with a silica gel column to give 28.1 g of 11.

11 (20 g: 36 mmol) was added to 150 g of methylcellosolve, and sodium methylate (8.0 g) was slowly added with stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for 1 hour and then further heated to 90 to 100 ° C.
For 20 hours. The reaction solution was poured into water, neutralized with dilute hydrochloric acid, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with a silica gel column to give 15.8 g of 12.
Obtained.

12 (15 g: 23 mmol) and triethylamine (7.0 g: 69 mmol) were added to dry TH
After adding to 100 ml of F and cooling to 0 to 5 ° C., acryloyl chloride (6.3 g: 70 mmol) was slowly added dropwise. After completion of the dropwise addition, the temperature was slowly returned to room temperature, and the mixture was stirred at room temperature for 6 hours. The reaction solution was poured into water, neutralized, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The residue was purified with a silica gel column to give 5.85 g of 13 (Compound No. 2-34) (oxidation potential: 0.78 V).

In the present invention, the compound having the hole transporting ability in the photosensitive layer is formed by polymerizing the hole transporting compound having two or more chain polymerizable functional groups in the same molecule. A three-dimensional crosslinked structure is formed with the above crosslinking points. The hole transporting compound can be polymerized or crosslinked alone or mixed with a compound having another chain polymerizable group, and the type / ratio thereof is all arbitrary. The compound having another chain polymerizable group as referred to herein includes both monomers and oligomers / polymers having a chain polymerizable group.

When the functional group of the hole transporting compound and the functional group of the other chain polymerizable compound are the same group or a group capable of polymerizing with each other, the two groups have a copolymerized three-dimensional crosslinked structure via a covalent bond. It is possible to take When the two functional groups are functional groups that do not polymerize with each other, the photosensitive layer may be a mixture of two or more three-dimensional cured products or a three-dimensional cured product of the main component in which another chain-polymerizable compound monomer or its monomer is present. Although it is configured as containing a cured product, its compounding ratio /
By properly controlling the film forming method, IPN (I
internet Penetrating Network)
That is, it is possible to form a mutual intrusion network structure.

Further, a photosensitive layer is formed from the above-mentioned hole transporting compound and a monomer or oligomer / polymer having no chain polymerizable group or a monomer or oligomer / polymer having a polymerizable group other than chain polymerizable group. May be.

Further, in some cases, it is possible to contain a hole transporting compound which is not chemically incorporated into the three-dimensional crosslinked structure, that is, has no chain polymerizable functional group. Further, other various additives, lubricants such as fine particles of fluorine atom-containing resin and the like may be contained.

The structure of the electrophotographic photoreceptor of the present invention has a structure in which a charge generating layer containing a charge generating material and a charge transporting layer containing a charge transporting material are laminated in this order on a conductive support. , Or a single-layer structure in which a charge generation material and a charge transport material are dispersed in the same layer. In the former laminated type, the charge transport layer may have two or more layers, and in the latter single layer type, a charge transport layer may be further formed on the photosensitive layer containing the same charge generation material and charge transport material. Further, a protective layer can be formed on the charge generation layer or the charge transport layer.

In any of these cases, the photosensitive layer contains one or both of the above-described hole transporting compound having a chain polymerizable group and a pre-hole transporting compound polymerized or crosslinked and cured by heat or ultraviolet rays. Just do it. However, in view of the characteristics of the electrophotographic photoreceptor, in particular, electrical characteristics such as residual potential and durability, a function-separated type electrophotographic photoreceptor having a charge generation layer / charge transport layer laminated in this order is preferable. An advantage of the present invention is that the surface layer can have high durability without lowering the charge transporting ability.

Next, a method for producing an electrophotographic photosensitive member according to the present invention will be specifically described.

The support of the electrophotographic photosensitive member may be any conductive material, for example, aluminum,
A metal or alloy such as copper, chromium, nickel, zinc and stainless steel formed into a drum or sheet, a metal foil such as aluminum and copper laminated on a plastic film, a plastic film made of aluminum, indium oxide and tin oxide And a metal provided with a conductive layer by applying a conductive material alone or together with a binder resin, and a plastic film and paper.

In the present invention, an undercoat layer having a barrier function and an adhesive function can be provided on the conductive support. The undercoat layer is used for improving the adhesiveness of the photosensitive layer, improving the coating property, protecting the support, covering defects on the support, improving the charge injection property from the support, and protecting the photosensitive layer against electrical breakdown. Formed.

Examples of the material of the undercoat layer include polyvinyl alcohol, poly-N-vinylimidazole, polyethylene oxide, ethyl cellulose, ethylene-acrylic acid copolymer, casein, polyamide, N-methoxymethylated 6 nylon, copolymer nylon, Glue and gelatin are known. These are dissolved in a suitable solvent and applied on a support. At this time, the film thickness is set to 0.
1-2 μm is preferred.

When the photoreceptor of the present invention is a function-separated type electrophotographic photoreceptor, a charge generation layer and a charge transport layer are laminated. Examples of the charge generation material used for the charge generation layer include selenium-tellurium, pyrylium, thiapyrylium dyes, and various kinds of central metals and crystal systems, specifically, for example, α,
phthalosinine compounds having crystal forms such as β, γ, ε and X type, anthantrone pigments, dibenzopyrene quinone pigments, pyranthrone pigments, trisazo pigments, disazo pigments, monoazo pigments, indigo pigments, quinacridone pigments,
Asymmetric quinocyanine pigments, quinocyanines and JP
And amorphous silicon described in JP-A-143645.

In the case of a function-separated type electrophotographic photoreceptor, the charge generation layer comprises a homogenizer, an ultrasonic dispersion, a ball mill, a vibrating ball mill, a sand mill, and an atomizer containing the charge generation material together with 0.3 to 4 times the amount of a binder resin and a solvent. It is well dispersed by a method such as a lighter and a roll mill, coated with a dispersion, and dried, or formed as a film of a single composition such as a vapor-deposited film of the charge generation material. The film thickness is preferably 5 μm or less, especially 0.1 to 2 μm
Is preferably within the range.

When a binder resin is used, for example, polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylate, methacrylate, vinylidene fluoride and trifluoroethylene, polyvinyl alcohol, polyvinyl alcohol Acetal, polycarbonate, polyester, polysulfone, polyphenylene oxide, polyurethane, cellulose resin,
Phenol resins, melamine resins, silicon resins, epoxy resins, and the like.

The hole transporting compound having a chain polymerizable functional group according to the present invention may be a charge transporting layer comprising a charge transporting material and a binder resin on the charge generating layer or on the charge generating layer. Can be used as a surface protective layer having a hole transporting ability (this surface protective layer is also a photosensitive layer since it has a hole transporting ability). In any case, the method of forming the surface layer includes:
After applying the solution containing the hole transporting compound, polymerization and
It is common to carry out a cross-linking reaction.However, a solution containing a hole-transporting compound is reacted in advance to obtain a cured product, and then a surface layer is formed by dispersing or dissolving in a solvent again. It is also possible. As a method of applying these solutions, for example, a dip coating method, a spray coating method, a curtain coating method, a spin coating method, and the like are known, but a dip coating method is preferable from the viewpoint of efficiency and productivity. In addition, vapor deposition, plasma, and other known film forming methods can be appropriately selected.

In the present invention, the polymerization / crosslinking reaction of the chain polymerizable group can be performed by either heat or light. When the polymerization reaction is carried out by heat, the polymerization reaction proceeds only with heat energy and a polymerization initiator may be required.However, in order to promote the reaction efficiently at a lower temperature, the addition of the initiator is required. Is desirable.

The polymerization initiator used in this case may be any one having a half-life at room temperature or higher. Specific examples thereof include ammonium persulfate, dicumyl peroxide,
Examples thereof include peroxides such as benzoyl peroxide, cyclohexane peroxide, t-butyl hydroperoxide and di-t-butyl peroxide, and azo compounds such as azobisbutyronitrile. The addition amount is 0.01 to 100 parts by mass of the total mass of the compound having a chain polymerizable group.
It is about 10 parts by mass, and the temperature of the reaction system can be appropriately selected from room temperature to 200 ° C. depending on the initiator.

In the present invention, with respect to polymerization / crosslinking using light in the present invention, it is extremely rare that the reaction proceeds only with light energy, and a photopolymerization initiator is generally used in combination.
In this case, the polymerization initiator mainly refers to those that absorb ultraviolet rays having a wavelength of 400 nm or less to generate active species such as radicals and ions and initiate polymerization, but specific examples thereof include:
Radical polymerization initiators such as acetophenone, benzoin, benzophenone and thioxanthone, and ionic polymerization initiators such as diazonium compounds, sulfonium compounds, iodonium compounds and metal complex compounds.

In recent years, however, a polymerization initiator which absorbs light in the infrared / visible region at a wavelength of 400 nm or more and generates the above-mentioned active species has been disclosed, and their use is also possible. The amount of the initiator added is based on the total mass of the compound having a chain polymerizable group.
It is about 0.01 to 50 parts by mass with respect to 00 parts by mass.
In the present invention, the above-mentioned heat and photopolymerization initiators can be used in combination.

When the hole transporting compound having a chain polymerizable group is used as a charge transporting layer, the amount of the hole transporting compound is based on the total mass of the charge transporting layer film after polymerization and crosslinking. The content of the hydrogenated product of the hole transporting group A having a chain polymerizable functional group represented by the general formula (1) is preferably 20% by mass or more, and more preferably 40% by mass or more. If it is less than that, the charge transporting ability is reduced, and problems such as a decrease in sensitivity and an increase in residual potential are likely to occur. In this case, the film thickness of the charge transport layer is preferably from 1 to 50 μm, and more preferably from 3 to 30 μm.

When the above-mentioned hole transporting compound is used as a surface protective layer on the charge generating layer / charge transporting layer, the underlying charge transporting layer may be made of a suitable charge transporting material such as poly-N
A polymer compound having a heterocyclic ring or a condensed polycyclic aromatic compound such as vinylcarbazole and polystyrylanthracene, a heterocyclic compound such as pyrazoline, imidazole, oxazole, triazole and carbazole, a triarylalkane derivative such as triphenylmethane, A low molecular weight compound such as a triarylamine derivative such as phenylamine, a phenylenediamine derivative, an N-phenylcarbazole derivative, a stilbene derivative, or a hydrazone derivative together with a suitable binder resin (can be selected from the above-described resins for the charge generation layer). It can be formed by applying and drying a solution dispersed / dissolved in a solvent by the above-mentioned known method.

In this case, the ratio of the charge transporting material to the binder resin is preferably from 30 to 100, more preferably from 50 to 100, assuming that the total weight of both is 100. You. If the amount of the charge transporting material is less than that, the charge transporting ability is reduced, and problems such as a decrease in sensitivity and an increase in residual potential are likely to occur. The total thickness of the charge transport layer including the upper surface protective layer is 1
決定 50 μm, preferably 5-30 μm
m.

In the present invention, in any of the above cases, the charge transporting material can be contained in the photosensitive layer containing the cured product of the hole transporting compound.
In the case of a single-layer type photosensitive layer, the charge-generating material is simultaneously contained in the solution containing the hole-transporting compound, and the solution may be provided with an appropriate undercoat layer or an intermediate layer.
The case where the polymer is formed by polymerization and crosslinking after coating on the conductive support, and the case where the hole transport is performed on the single-layer photosensitive layer composed of the charge generation material and the charge transport material provided on the conductive support. Any of the methods of polymerizing and cross-linking after applying the solution containing the acidic compound is possible.

Various additives can be added to the photosensitive layer in the present invention. The additive is a deterioration inhibitor such as an antioxidant and an ultraviolet absorber, a lubricant such as fine particles of a fluorine atom-containing resin, and the like.

FIG. 1 shows a schematic configuration of an electrophotographic apparatus having a process cartridge having the electrophotographic photosensitive member of the present invention.

In the figure, reference numeral 1 denotes a drum-shaped electrophotographic photosensitive member of the present invention, which is rotated around an axis 2 at a predetermined peripheral speed in a direction indicated by an arrow. In the rotation process, the peripheral surface of the electrophotographic photoreceptor 1 is uniformly charged at a predetermined positive or negative potential by the primary charging means 3, and then the photosensitive member 1 is exposed to light from exposure means (not shown) such as slit exposure or laser beam scanning exposure. The exposure light 4 is received. Thus, an electrostatic latent image is sequentially formed on the peripheral surface of the electrophotographic photosensitive member 1.

The formed electrostatic latent image is then developed.
The toner-developed image developed by the above is taken out from a paper supply unit (not shown) between the electrophotographic photosensitive member 1 and the transfer means 6 in synchronization with the rotation of the electrophotographic photosensitive member 1 and fed. The image is sequentially transferred to the transferred transfer material 7 by the transfer means 6.

The transfer material 7 which has undergone the image transfer is separated from the electrophotographic photosensitive member surface, introduced into the image fixing means 8 and subjected to image fixing to be printed out of the apparatus as a copy.

After the transfer of the image, the surface of the electrophotographic photosensitive member 1 is cleaned by removing the untransferred toner by the cleaning means 9, and is further subjected to a charge removal treatment by the pre-exposure light 10 from the pre-exposure means (not shown). After that, it is repeatedly used for image formation. When the primary charging unit 3 is a contact charging unit using a charging roller or the like, the pre-exposure is not necessarily required.

In the present invention, a plurality of components such as the above-described electrophotographic photosensitive member 1, primary charging means 3, developing means 5, and cleaning means 9 are integrally connected as a process cartridge. The process cartridge may be configured to be detachable from a main body of an electrophotographic apparatus such as a copying machine or a laser beam printer. For example, at least one of the primary charging unit 3, the developing unit 5, and the cleaning unit 9 is integrally supported with the electrophotographic photosensitive member 1 to form a cartridge, and is attached to and detached from the apparatus main body using the guide means such as the rail 12 of the apparatus main body. A flexible process cartridge 11 can be provided.

When the electrophotographic apparatus is a copier or a printer, the exposure light 4 is reflected light or transmitted light from the original, or the original is read by a sensor, converted into a signal, and a laser beam is emitted in accordance with the signal. Scanning, LED
Light emitted by driving the array, driving the liquid crystal shutter array, and the like.

The electrophotographic photosensitive member of the present invention can be used not only for an electrophotographic copying machine but also for a laser beam printer,
It can be widely used in electrophotographic applications such as CRT printers, LED printers, liquid crystal printers, faxes and laser plate making.

[0140]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples. In addition, "part" shows a mass part.

Example 1-1 First, a paint for a conductive layer was prepared by the following procedure. 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% antimony oxide,
Phenol resin 25 parts, methyl cellosolve 20 parts, methanol 5 parts and silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight 300
0) It was prepared by dispersing 0.002 parts in a sand mill using 1 mmφ glass beads for 2 hours. 30 of this paint
A 20 μm-thick conductive layer was formed by applying a dip coating method on an aluminum cylinder having a diameter of mm and drying it at 140 ° C. for 30 minutes.

Next, 5 parts of N-methoxymethylated nylon was dissolved in 95 parts of methanol to prepare a coating for an intermediate layer. This paint was applied on the conductive layer by a dip coating method, and dried at 100 ° C. for 20 minutes to form an intermediate layer having a thickness of 0.6 μm.

Next, 5 parts of a bisazo pigment represented by the following structural formula (18), 2 parts of a polyvinyl butyral resin, and 35 parts of cyclohexanone were dispersed for 24 hours by a sand mill using 1 mmφ glass beads, and tetrahydrofuran was further added. This was used as a paint for a charge generation layer. This paint is applied on the intermediate layer by a dip coating method,
The film thickness is 0.2 μm by drying at 15 ° C. for 15 minutes.
Was formed.

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Next, Compound Example No. For a charge transport layer, 60 parts of a hole transporting compound of No. 1-13 and 0.6 part of a photopolymerization initiator represented by the following structural formula (19) are dissolved in a mixed solvent of 30 parts of monochlorobenzene / 30 parts of dichloromethane. A paint was prepared. This paint was coated on the above-mentioned charge generation layer, and 750 mW using a metal halide lamp.
By curing for 20 seconds at a light intensity of / cm ² ,
A charge transport layer having a thickness of 15 μm was formed to obtain an electrophotographic photoreceptor.

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The produced electrophotographic photosensitive member was evaluated for its sedimentability with time, electrophotographic characteristics, and durability. With respect to the sedimentability with time, a urethane rubber cleaning blade for a copying machine was pressed against the surface of the photoreceptor, stored at 75 ° C., and an accelerated test for the sedimentability was performed. After 14 days, the surface of the electrophotographic photosensitive member was observed with a microscope to determine the presence or absence of precipitation. When there was no precipitation, the test was continued until further 30 days later.

The electrophotographic characteristics and durability were evaluated by mounting this electrophotographic photosensitive member on an LBP-SX manufactured by Canon Inc. and evaluating the electrophotographic characteristics and durability. The initial electrophotographic characteristics [dark potential Vd, light decay sensitivity (light amount required to attenuate light to -150 V at dark portion potential -700 V setting) and residual potential Vsl (light amount three times the light decay sensitivity) were applied. Potential), a 10,000-sheet paper-pass durability test was performed, and the occurrence of image defects was visually observed.
The shaving amount of the electrophotographic photosensitive member and the electrophotographic characteristics after the endurance were measured, and the respective change values ΔVd and ΔVl (when the same amount of light as the amount of light at which Vl became −150 V initially was irradiated after the endurance, Vl) and ΔVsl.

The results are shown in Table 3. The electrophotographic photosensitive member of the present invention did not precipitate, had good electrophotographic properties, had a small amount of scraping at endurance, and had good electrophotographic properties at endurance. Shows very stable and good characteristics such that almost no change is observed.

(Examples 1-2 to 1-11) Example 1-1
In the hole transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1-1, except that 1-13 was replaced with the compound shown in Table 4. Table 3 shows the results.

(Examples 1-12-1-14) Example 1-
1, the hole transporting compound No. 1 Example 1-1 except that 1-13 was replaced with the compound shown in Table 4 and the photopolymerization initiator represented by the structural formula (19) was replaced by a photopolymerization initiator represented by the following structural formula (20). An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated. Table 3 shows the results.

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(Example 1-15) In Example 1-1, the hole transporting compound No. Compound No. 1-13 as Compound No. 1-1
In the same manner as in Example 1-1, except that 0.3 parts of the photopolymerization initiator represented by the structural formula (19) and 0.3 parts of the photopolymerization initiator represented by the structural formula (20) were used instead of 5 An electrophotographic photoreceptor was prepared and evaluated. Table 3 shows the results.

(Example 1-16) In Example 1-1, the photopolymerization initiator represented by the structural formula (19) was replaced by a thermal polymerization initiator represented by the following structural formula (21), and instead of ultraviolet curing, An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-1, except that the thermosetting reaction was performed at 140 ° C. for 1 hour. Table 3 shows the results.

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(Example 1-17) The compound having the hole transporting compound No. Compound No. 1-13 as Compound No. 1-
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-16, except that the composition was changed to 39. Table 3 shows the results.

Example 1-18 In Example 1-16, the compound having the hole-transporting compound No. Compound No. 1-13 as Compound No. 1-
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-16 except that the photoconductor was replaced with 37. Table 3 shows the results.

(Example 1-19) In Example 1-1, the hole transporting compound No. The amount of 1-13 was 48 parts, and the acrylic monomer represented by the following structural formula (22) was further added to 1 part.
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1-1 except that 2 parts were added. Table 3 shows the results.

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Example 1-20 In Example 1-12, the compound having the hole-transporting compound No. The amount of 1-35 is 48 parts,
Further, an electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1-12, except that 12 parts of an epoxy monomer represented by the following structural formula (23) was added. Table 3 shows the results.

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Example 1-21 In Example 1-1, the hole transporting compound No. An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-1, except that the amount of 1-13 was 48 parts, and that 12 parts of an acrylic oligomer represented by the following structural formula (24) was further added. Table 3 shows the results.

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(Example 1-22) In Example 1-16, the compound having the hole-transporting compound No. The amount of 1-13 is 48 parts,
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1-16, except that 12 parts of the acrylic monomer represented by the structural formula (22) was added. Table 3 shows the results.

Example 1-23 After forming a charge generation layer in Example 1-1, 20 parts of a styryl compound represented by the following structural formula (25) and a repeating unit represented by the following structural formula (26) were added. A charge transport layer was formed on the charge generation layer using a charge transport layer paint prepared by dissolving 10 parts of a polycarbonate resin having the same in a mixed solvent of 50 parts of monochlorobenzene / 20 parts of dichloromethane. At this time, the thickness of the charge transport layer was 10 μm.

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[0167]

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Next, the hole transporting compound No. 1-13
Was dissolved in a mixed solvent of 50 parts of monochlorobenzene / 30 parts of dichloromethane to prepare a coating for a surface protective layer. This paint was applied on the charge transport layer by a spray coating method, and was coated with a metal halide lamp.
By curing at a light intensity of 50 mW / cm ² for 30 seconds, a surface protective layer having a thickness of 5 μm was formed, and an electrophotographic photosensitive member was obtained. This electrophotographic photosensitive member was evaluated in the same manner as in Example 1-1. Table 3 shows the results.

(Example 1-24) In Example 1-23, the compound having the hole-transporting compound No. Compound No. 1-13 as Compound No. 1-
35. An electrophotographic photoreceptor in the same manner as in Example 1-23, except that the photopolymerization initiator represented by Structural Formula (20) was used instead of the photopolymerization initiator represented by Structural Formula (19) in place of 35 Was prepared and evaluated. Table 3 shows the results.

(Example 1-25) In Example 1-23, the compound having the hole-transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1-23, except that 1 to 30 parts was used and 30 parts of an acrylic monomer represented by the structural formula (22) was added. Table 3 shows the results.

(Example 1-26) In Example 1-24, the compound having the hole transporting compound No. An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-24, except that 1 to 35 parts was used and 30 parts of the epoxy monomer represented by the structural formula (23) was added. Table 3 shows the results.

Example 1-27 Example 1-25 was repeated except that the acrylic oligomer represented by the structural formula (24) was used in place of the acrylic monomer represented by the structural formula (22) in the example 1-25. An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated. Table 3 shows the results.

[0173]

[Table 3]

[0174]

[Table 4]

(Example 2-1) In Example 1-1, the hole transporting compound No. No. 1-13 is No. An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-1 except that 2-1 was used. Table 5 shows the results.

(Examples 2-2 to 2-11) Example 2-1
In the hole transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 2-1 except that 2-1 was replaced with the compound shown in Table 6. Table 5 shows the results.

(Examples 2-12 to 2-14) Example 2
1, the hole transporting compound No. 1 Example 2-1 was the same as Example 2-1 except that 2-1 was replaced with the compound shown in Table 6 and the photopolymerization initiator shown in Structural Formula (19) was replaced with the photopolymerization initiator shown in Structural Formula (20). In the same manner, an electrophotographic photosensitive member was prepared and evaluated. Table 5 shows the results.

(Example 2-15) The compound having the hole transporting compound No. 2-1 was designated as Compound No. 2-19
In the same manner as in Example 2-1 except that the photopolymerization initiator represented by the structural formula (19) and the photopolymerization initiator represented by the structural formula (20) were further replaced by 0.3 part and 0.3 part, respectively. To prepare an electrophotographic photosensitive member and evaluated. Table 5 shows the results.

(Example 2-16) The photopolymerization initiator represented by the structural formula (19) in Example 2-1 was replaced with the structural formula (2)
Except that the thermal polymerization initiator shown in 1) was replaced with a thermal curing reaction instead of ultraviolet curing and the temperature was set at 140 ° C. for 1 hour,
An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 2-1. Table 5 shows the results.

(Example 2-17) The compound having the hole transporting compound No. 2-1 was designated as Compound No. 2-4
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 2-16, except that the composition was changed to 7. Table 5 shows the results.

(Example 2-18) The compound having the hole transporting compound No. 2-1 was designated as Compound No. 2-5
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 2-16 except that the value was changed to 0. Table 5 shows the results.

(Example 2-19) The compound having the hole transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 2-1 except that the amount of 2-1 was 48 parts and further 12 parts of an acrylic monomer represented by the structural formula (22) was added. Table 5 shows the results.

(Example 2-20) In Example 2-12, the compound having the hole-transporting compound No. The amount of 2-48 is 48 parts,
Further, the epoxy monomer represented by the structural formula (23) is
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 2-12, except for adding a part. Table 5 shows the results.

(Example 2-21) The compound having the hole-transporting compound No. An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 2-1 except that the amount of 2-1 was 48 parts and further 12 parts of an acrylic oligomer represented by the structural formula (24) was added. Table 5 shows the results.

(Example 2-22) In Example 2-16, the compound having the hole-transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 2-16, except that the amount of 2-1 was 48 parts and the acrylic monomer represented by the structural formula (22) was added in 12 parts. Table 5 shows the results.

(Example 2-23) After forming a charge generation layer in Example 2-1, a polycarbonate having 20 parts of a styryl compound represented by the structural formula (25) and a repeating unit represented by the structural formula (26) A charge transport layer was formed on the charge generation layer using a charge transport layer paint prepared by dissolving 10 parts of a resin in a mixed solvent of 50 parts of monochlorobenzene / 20 parts of dichloromethane. At this time, the thickness of the charge transport layer was 10 μm.

Next, the hole transporting compound No. 2-1
60 parts and a photopolymerization initiator represented by the structural formula (19)
6 parts of monochlorobenzene 50 parts / dichloromethane 30
Was dissolved in the mixed solvent of parts to prepare a coating for the surface protective layer. This paint was applied onto the charge transport layer by spray coating, and the paint was applied to a metal halide lamp for 75 minutes.
By curing at a light intensity of 0 mW / cm ² for 30 seconds, a surface protective layer having a thickness of 5 μm was formed, and an electrophotographic photosensitive member was obtained. This electrophotographic photosensitive member was evaluated in the same manner as in Example 2-1. Table 5 shows the results.

(Example 2-24) In Example 2-23, the compound having the hole-transporting compound No. 2-1 was designated as Compound No. 2-4
Electrophotographic photoreceptor in the same manner as in Example 2-23, except that the photopolymerization initiator represented by Structural Formula (20) was used instead of the photopolymerization initiator represented by Structural Formula (19) in place of 8 Was prepared and evaluated. Table 5 shows the results.

(Example 2-25) In Example 2-23, the compound having the hole transporting compound No. An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 2-23 except that 30 parts of 2-1 was used and 30 parts of an acrylic monomer represented by the structural formula (22) was added. Table 5 shows the results.

(Example 2-26) In Example 2-24, the compound having the hole transporting compound No. An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 2-24, except that 30 parts of 2-48 was used and 30 parts of the epoxy monomer represented by the structural formula (23) was added. Table 5 shows the results.

Example 2-27 Example 2-25 was repeated, except that the acrylic monomer represented by the structural formula (24) was used in place of the acrylic monomer represented by the structural formula (22). An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated. Table 5 shows the results.

[0192]

[Table 5]

[0193]

[Table 6]

(Comparative Example 1) After forming the charge generation layer in Example 1-1, polymethyl having 15 parts of a styryl compound represented by the structural formula (25) and a repeating unit represented by the following structural formula (27) was prepared. A charge transport layer was formed on the charge generation layer using a charge transport layer paint prepared by dissolving 15 parts of a methacrylate resin in a mixed solvent of 50 parts of monochlorobenzene / 20 parts of dichloromethane. At this time, the thickness of the charge transport layer was 15 μm.

[0195]

Embedded image

This electrophotographic photosensitive member was evaluated in the same manner as in Example 1-1. As a result, precipitation was observed after 14 days. On the other hand, the electrophotographic characteristics in the initial stage were good, but the amount of surface layer shaved in durability was large, and image defects such as fogging and scratches occurred. Further, after 8000 sheets, the thickness of the charge transport layer was reduced due to scraping, and poor charging occurred, making image formation impossible. Table 7 shows the results.

Comparative Example 2 In Comparative Example 1, the structural formula (2
An electrophotographic photosensitive member was produced and evaluated in the same manner as in Comparative Example 1 except that the polycarbonate resin represented by the structural formula (26) was used instead of the polymethyl methacrylate resin represented by 7), and as a result, after 30 days, Precipitation was observed. In addition, although the durability was slightly improved as compared with the case of the polymethyl methacrylate resin, it was not sufficient, and image defects also occurred after the durability. Table 7 shows the results.

Comparative Example 3 In Comparative Example 2, the structural formula (2
10 parts of a styryl compound represented by 5) and structural formula (2)
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Comparative Example 2 except that 15 parts of the polycarbonate resin shown in 6) were used. As a result, although the durability was improved as compared with Comparative Example 2, the charge transfer material , The charge transport ability was reduced, and the sensitivity was reduced and the residual potential was increased. As a result, a ghost was observed in the image. Table 7 shows the results.

(Comparative Example 4) After forming the charge transport layer in Example 1-23, 10 parts of the styryl compound represented by the structural formula (25) and 15 parts of the polycarbonate resin represented by the structural formula (26) were converted to monochlorobenzene. It was dissolved in a mixed solvent of 50 parts / 30 parts of dichloromethane to prepare a coating for a surface protective layer. This paint was applied onto the charge transport layer by a spray coating method, and dried at 120 ° C. for 1 hour to form a surface protective layer having a thickness of 5 μm. Comparative Example 3
On the other hand, since the charge transporting layer having high charge transporting ability is in the lower layer, the sensitivity is lowered, the residual potential is slightly increased, and the shaving amount is improved, but the image after the durability still has scratches / fog. Therefore, sufficient durability could not be secured. Table 7 shows the results.

Comparative Example 5 The hole-transporting compound No. in Example 1-1 was prepared. JP-A-5-21 instead of 1-13
An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 1-1, except that the compound represented by the following structural formula (28) disclosed in JP-A-6249 was used. As a result, the initial electrophotographic properties were good, but the durability was significantly lower than that of Example 1-1. Table 7 shows the results.

[0201]

Embedded image

Comparative Example 6 The hole transporting compound No. in Example 1-19 was used. Instead of 1-13, the structural formula (2
Example 1-19 except that the compound shown in 7) was used.
An electrophotographic photoreceptor was prepared in the same manner as described above and evaluated. As a result, the electrophotographic characteristics in the initial stage were good, but Examples 1-19.
The durability was greatly reduced as compared with. Table 7 shows the results.

(Comparative Example 7) After the charge generation layer was formed in Example 1-1, the charge generation layer was formed as described in JP-A-8-248649.
Polycarbonate resin 20 represented by the following structural formula (29) synthesized according to the production method described in Nos. 10 to 11
A charge transport layer was formed on the charge generation layer using a charge transport layer paint prepared by dissolving the above-mentioned parts in 80 parts of tetrahydrofuran. At this time, the thickness of the charge transport layer was 15 μm. The electrophotographic photoreceptor was evaluated in the same manner as in Example 1-1. As a result, although the mechanical strength was improved as compared with Comparative Examples 1 and 2, sufficient durability could not be secured. Table 7 shows the results.

[0204]

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[0205]

[Table 7]

[0206]

As described above, the electrophotographic photoreceptor of the present invention has a
It has an effect of excellent abrasion resistance and scratch resistance. Further, the electrophotographic characteristics such as sensitivity and residual potential are very good, and stable performance can be exhibited even when repeatedly used. Further, the effect of the electrophotographic photosensitive member is naturally exerted also in a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member, and high image quality is maintained for a long time.

[Brief description of the drawings]

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

[Description of Signs] 1 electrophotographic photoreceptor 2 axis 3 charging means 4 exposure light 5 developing means 6 transfer means 7 transfer material 8 fixing means 9 cleaning means 10 pre-exposure light 11 process cartridge 12 rail

Claims (17)

[Claims] 1. An electrophotographic apparatus having a photosensitive layer on a conductive support.
In the true photoreceptor, the photosensitive layer is represented by the following general formula (1).
Having two or more chain-polymerizable functional groups in the same molecule
Of a hole-transporting compound by heat or ultraviolet light
An electrophotographic photosensitive member containing a compound. Embedded image｛(Wherein A represents a hole transporting group;¹And P^TwoIs a chain
Indicates a polymerizable functional group; P ¹And P^TwoMay be the same or different
Z represents an organic residue which may have a substituent; a, b
And d represent 0 or an integer of 1 or more, and a + b × d represents 2 or more.
The above integer; and when a is 2 or more, P¹Are the same
May be different, and when d is 2 or more, P^TwoAre the same but different
And when b is 2 or more, Z and P^TwoIs the same
(A or P may be different.) In the general formula (1), A and P¹And binding site with Z
Is replaced by a hydrogen atom.
Hydrogenated or condensed heterocyclic ring or the following general formula (2) or general formula
This is indicated by (4). Embedded image(Where R¹And R^TwoIs an alkyl which may have a substituent
Group, aralkyl group which may have a substituent or
Represents an optionally substituted aryl group;¹And R^TwoSame but different
May be used; Ar¹Is an aryl group which may have a substituent
Provided that the above-mentioned fused ring hydrocarbon, fused heterocyclic ring and
The general formula (2) includes one or more groups represented by the following general formula (3).
Have on top. Embedded image(Where R^ThreeAnd R^FourIs an alkyl which may have a substituent
Group, aralkyl group which may have a substituent,
An aryl group or a hydrogen atom,^ThreeAnd R^FourIs
May be the same or different; Ar^TwoHas a substituent
An optionally substituted aryl group; n¹Is 0 or an integer of 1-2
Is shown).(Wherein, Ar^ThreeAnd Ar^FourIs an aryl which may have a substituent
A group represented by Ar^ThreeAnd Ar^FourMay be the same or different
I; R^FiveRepresents an alkyl group which may have a substituent,
An aralkyl group which may have
Represents a reel group) provided that the compound represented by the general formula (4)
Has one or more groups represented by the following general formula (5). Embedded image(Where R⁶And R⁷Is an alkyl which may have a substituent
Group, aralkyl group which may have a substituent,
An aryl group or a hydrogen atom,⁶And R⁷Is
May be the same or different; Ar^FiveHas a substituent
An optionally substituted aryl group; n^TwoIs 0 or an integer of 1-2
示 す) 2. In the above formula (1), the hole transporting compound in which the bonding site of A, P ¹ and Z is replaced by a hydrogen atom is a fused ring hydrocarbon or a fused heterocyclic ring or a compound represented by the following formula (2) The electrophotographic photoreceptor according to claim 1, wherein 3. The hole-transporting compound of the above general formula (1) wherein the bonding site between A, P ¹ and Z is replaced by a hydrogen atom, is represented by the following general formula (4). Electrophotographic photoreceptor. 4. Z in the general formula (1) is an alkylene group which may have a substituent, an arylene group which may have a substituent, CR ⁸ ＝ CR ⁹ (where R ⁸ and R ⁹ are substituted An alkyl group which may have a group, an aryl group which may have a substituent or a hydrogen atom, and R ⁸ and R ⁹ may be the same or different), C ＝ O, S ＝ O, SO ₂ The electrophotographic photoreceptor according to any one of claims 1 to 3, wherein the electrophotographic photoreceptor represents an organic residue which is one or arbitrarily combined from an oxygen atom or a sulfur atom. 5. Z in the general formula (1) is the following general formula:
The electron according to any one of claims 1 to 4, which is represented by (6).
Photoreceptor. Embedded image(Where X¹~ X^ThreeIs an alkylene which may have a substituent
Group, (CR^Ten= CR¹¹)_m, C = O, S = O, SO_Two,acid
Represents an elementary atom or a sulfur atom;⁶And Ar⁷Is a substituent
Represents an arylene group which may be present;^TenAnd R¹¹Is replaced
An alkyl group which may have a group;
R represents a reel group or a hydrogen atom;^TenAnd R ¹¹Are the same
M may be an integer from 1 to 5, p to t may be 0 or 1
Represents an integer of from 10 to 10, provided that p to t are simultaneously 0
Not) 6. The electrophotographic photosensitive member according to claim 1, wherein Z in the general formula (1) is represented by the following general formula (7). Embedded image (Wherein, Ar ⁸ represents an arylene group which may have a substituent; X ⁴ and X ⁵ represent (CH ₂ ) _g , (CH CR ¹² ) _h ,
C = represents O or an oxygen atom; R ¹² represents an alkyl group which may have a substituent group, an optionally substituted aryl group or a hydrogen atom, g is an integer of from 1 to 10, h is 1 Integers from 5 to 5, u to w each represent 0 or an integer from 1 to 10;
Are never 0 at the same time) 7. A hole-transporting compound in which, in the above general formula (1), the bonding site between A, P ¹ and Z is replaced by a hydrogen atom, is a general formula (2), and R ¹ and R ² are 7. The electrophotographic photoreceptor according to claim 1, which is an aryl group which may have a substituent. 8. The method according to claim 1, wherein R ^{4 in the} general formula (3) is an aryl group which may have a substituent.
The electrophotographic photosensitive member according to any one of the above. 9. The method according to claim 1, wherein R ^{5 in the} general formula (4) is an aryl group which may have a substituent.
The electrophotographic photosensitive member according to any one of the above. 10. The electrophotographic photosensitive member according to claim 1, wherein R ^{7 in the} general formula (5) is an aryl group which may have a substituent. 11. The electrophotographic photosensitive material according to claim 1, wherein one or both of the chain polymerizable groups P ¹ and P ² is an unsaturated polymerizable functional group represented by the following general formula (8). body. Embedded image (Wherein E is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent, a cyano group, a nitro group, an alkoxy group, -COOR ¹³
{R ¹³ is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent} or -CONR ¹⁴ R
¹⁵ ｛R ¹⁴ and R ^{15 each} represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent. Represents the same or different｝, and W represents a divalent aryl group optionally having a substituent, a divalent alkylene group optionally having a substituent, -COO-, -O −, −
OO—, —S— or —CONR ¹⁶ — ｛R ¹⁶ is a hydrogen atom,
A halogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent; f represents 0 or 1) 12. The electrophotographic photosensitive member according to claim 1, wherein one or both of the chain polymerizable groups P ¹ and P ² is a cyclic ether group represented by the following general formula (9). Embedded image (Wherein, R ¹⁷ and R ¹⁸ represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent, and n is 1 to 10
Indicates an integer) 13. The electrophotographic photoreceptor according to claim 1, wherein one or both of the chain polymerizable groups P ¹ and P ² is an alicyclic epoxy group represented by the following general formula (10). . Embedded image (Wherein, R ¹⁹ and R ²⁰ represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent or an aryl group which may have a substituent, and n is 0 or 1
Represents an integer from 10 to 10) 14. The electrophotographic photosensitive material according to claim 1, wherein one or both of the chain polymerizable groups P ¹ and P ² are any of the following formulas (11) to (17). body. Embedded image 15. The method according to claim 1, wherein the oxidation potential of the hole transporting compound having two or more chain polymerizable functional groups in the same molecule is 0.4 to 1.2 (V). An electrophotographic photoreceptor as described in Crab. 16. An electrophotographic photoreceptor according to claim 1, wherein said electrophotographic photoreceptor is charged with a charging means, and said electrophotographic photoreceptor on which an electrostatic latent image is formed is developed with toner. Developing means, and at least one means selected from the group consisting of a cleaning means for collecting residual toner on the electrophotographic photoreceptor after the transfer step, are integrally supported together, and are detachably attached to the electrophotographic apparatus main body. Characteristic process cartridge. 17. An electrophotographic photoreceptor according to claim 1, a charging means for charging the electrophotographic photoreceptor, and exposing the charged electrophotographic photoreceptor to form an electrostatic latent image. An electrophotographic apparatus comprising: an exposure unit; a developing unit that develops an electrophotographic photosensitive member having an electrostatic latent image formed thereon with toner; and a transfer unit that transfers a toner image on a transfer material.