JPH06273950A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain the photosensitive body which is very high in sensitivity, small in the residual electric potential having possibility of causing a fogging, small in the build-up of the residual electric potential due to repetitive use and in the fluctuation in surface electric potential and sensitivity because the fatigue by light is low and excellent in durability. CONSTITUTION:The electrophotographic sensitive body has the photosensitive layer containing the aryl amines compd. expressed by a general formula on a conductive supporting body. In the formula, X is hydrogen atom or-CR<8>=C(R<9>) R<10>. Y is O-A<1>-O or A<2>-O-A<3>. A<1> is a bivalent hydrocarbon residual group. A<2> and A<3> are alkylene, allylene group, etc., Ar<1> and Ar<2> are alkyl, aryl group, etc., R<1>-R<4> are hydrogen atom, halogen atom, alkyl group, etc., R<5>-R<10> are hydrogen atom, alkyl, aryl group, etc.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor. More specifically, it relates to a very sensitive and high-performance electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive substance.

[0002]

2. Description of the Related Art Conventionally, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used for the photosensitive layer of electrophotographic photoreceptors. However, selenium and cadmium sulfide need to be recovered as poisons, selenium has poor heat resistance because it is crystallized by heat, cadmium sulfide and zinc oxide have poor moisture resistance, and zinc oxide has no printing durability. However, the efforts for developing a new photoconductor have been continued. Recently, studies have been conducted on the use of organic photoconductive materials in the photosensitive layer of electrophotographic photoconductors, and some of them have been put to practical use. Organic photoconductive materials are lighter than inorganic ones, are easier to form films, are easier to manufacture photoconductors, and depending on the type, materials that can produce transparent photoconductors are pollution-free It has advantages such as

Recently, a so-called function-separated type photoconductor, in which separate functions of charge carrier generation and transfer are shared by different compounds, has become the mainstream of development because it is effective for high sensitivity. The organic photoconductor is also put into practical use. As the charge carrier transfer medium, there are a case where a high molecular weight photoconductive compound such as polyvinylcarbazole is used and a case where a low molecular weight photoconductive compound is dispersed and dissolved in a binder polymer.

[0004]

In particular, organic low-molecular-weight photoconductive compounds can easily select mechanical properties as a binder because they have excellent film-forming properties, flexibility and adhesive properties. (See Japanese Patent Application Laid-Open No. 60-196767, Japanese Patent Application Laid-Open No. 60-218652, Japanese Patent Application Laid-Open No. 60-2331).
56, JP-A-63-48552, JP-A-1
-267552, Japanese Patent Publication No. 3-39306,
JP-A-3-113459 and JP-A-3-12335.
No. 8, JP-A-3-149560, etc.). However, it has been difficult to find a compound suitable for producing a highly sensitive photoreceptor.

Further, in the continuous demand for high sensitivity,
In terms of electrical characteristics, there are various problems such as insufficient residual potential, poor photoresponsiveness, deterioration of chargeability after repeated use, and accumulation of residual potential. There has been reported a technique (Japanese Patent Application Laid-Open No. 61-134767) that uses a combination of hydrazone compounds to prevent the residual potential from increasing without significantly impairing other properties of the photoreceptor. However, the balance of the characteristics is not always sufficient, and there has been a demand for a technique for improving the characteristics of the photoreceptor as a whole in a well-balanced manner.

Further, a semiconductor laser has been positively applied in the printer field as a light source. In this case, the wavelength of the light source is around 800 nm, and therefore 800
There is a strong demand for the development of a photoconductor having high sensitivity to long-wavelength light of around nm. Materials which meet this purpose are disclosed in JP-A-59-49544 and JP-A-59-59.
214034, JP 61-109056, JP 61-171771, JP 61-2.
17050, Japanese Patent Laid-Open No. 61-239248,
JP-A-62-67094, JP-A-62-1346
51, JP-A-62-275272, JP-A-63-198067, and JP-A-63-198068.
JP, JP-A-63-210942, JP, JP-A-63
Materials described in JP-A-218768, etc.
Various oxytitanium phthalocyanines each having a crystal type suitable as a material for an electrophotographic photoreceptor are known. However, there has been a further demand for an electrophotographic photoreceptor having high sensitivity to long-wavelength light and excellent other electric characteristics.

The present invention has been made to solve the above problems, and a first object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity and high durability. The second object is high sensitivity, the residual potential is sufficiently low even when the film thickness is increased, the characteristic is small even after repeated use, and the electrophotographic photoreceptor has excellent durability. To provide.

A third object of the present invention is to provide a well-balanced electrophotographic photosensitive member which is highly sensitive even at a long wavelength of about 800 nm and has good chargeability, dark decay, residual potential and the like.

[0009]

DISCLOSURE OF THE INVENTION The inventors of the present invention have found that a specific arylamine compound is suitable as a result of intensive research on organic low-molecular photoconductive compounds that can satisfy these objects. Came to. That is, the gist of the present invention is to provide the following general formula [I] on a conductive support.

[0010]

[Chemical 4]

(In the formula, X is a hydrogen atom or a general formula [II]

[0012]

[Chemical 5]

Represents a group represented by the formula; Y is a compound represented by the general formula [III
 ] -OA¹-O- [III] or general formula [IV] -A²-OA³-Represents a group represented by [IV], and in the general formula [III], A¹Is replaced
Represents a divalent hydrocarbon residue which may have a group,
In general formula [IV], A²And A³Each has a substituent
Optionally, an alkylene group, which may have a substituent
Arylene group or alkylene which may have a substituent
A group in which a group and an arylene group which may have a substituent are bonded
Represents A²And A³Whether they are the same or different
Well; Ar ¹And Ar²Each have a substituent
Optionally substituted alkyl group, optionally substituted aryl
Represents a group or a heterocyclic group which may have a substituent.
May be the same or different from each other; R¹, R²，
R³And R^FourAre hydrogen atom, halogen atom, and
Alkyl group which may have a substituent, which may have a substituent
Represents a good alkoxy group or substituted amino group,
May be the same or different from each other; R^Five, R⁶, R
⁷, R⁸, R⁹And R^TenAre the hydrogen atom and
Alkyl group which may have a substituent, which may have a substituent
Shows an aryl group or a heterocyclic group which may have a substituent.
However, these may be the same or different from each other,
Kuha R⁶And R⁷, R⁹And R^TenAre condensed to form a carbocyclic group or
A heterocyclic group may be formed, provided that R⁶And R⁷From
Naru pair, R⁹And R^TenIs a pair consisting of one of each pair
When is a hydrogen atom or an alkyl group, the other is
Or a heterocyclic group. ) Ally
Characterized by having a photosensitive layer containing a ruamine-based compound
In the electrophotographic photoreceptor to

Further, it is characterized by having a photosensitive layer containing an arylamine compound represented by the general formula [I] and a pyrenehydrazone compound represented by the following general formula [X] on a conductive support. There is in the electrophotographic photoreceptor for

[0015]

[Chemical 6]

(In the formula, R ¹¹ represents an alkyl group, an allyl group, an aryl group or an aralkyl group, the aryl group and the aralkyl group may have a substituent, and R ¹² has a substituent. In addition, an arylamine compound represented by the above general formula [I] is contained as a charge transport material on a conductive support.
A photoreceptor for electrophotography, comprising a photosensitive layer containing oxytitanium phthalocyanine showing a main diffraction peak at a black angle (2θ ± 0.2 °) 27.3 ° of an X-ray diffraction spectrum as a charge generating material. Exist.

The present invention will be described in detail below. The electrophotographic photoreceptor of the present invention contains the arylamine compound represented by the general formula [I] in the photosensitive layer. In the above general formula [I], X is a hydrogen atom or a general formula [II].

[0018]

[Chemical 7]

Represents a group represented by Y is represented by the general formula [II
I] -O-A ¹ -O- [III] or the general formula (IV) -A ² -O-A ³ - represents a group represented by (IV). In the general formula [III], A ¹ is an alkylene group such as a methylene group, an ethylene group or a propylene group; an arylene group such as a phenylene group, a biphenylene group or a naphthylene group; a group in which an alkylene group such as a xylylene group and an arylene group are bonded. A cycloalkylene group such as a cyclohexylene group; a divalent hydrocarbon residue such as a vinylene group,
Particularly, an alkylene group, an arylene group, or a group in which an alkylene group and an arylene group are bonded is preferable. In general formula [IV], A
² and A ³ each represent an alkylene group, an arylene group, or a group in which an alkylene group and an arylene group are bonded, and A ² and A ³ may be the same or different from each other,
These A ¹ , A ² and A ³ groups include halogen atoms, hydroxyl groups, saturated or unsaturated hydrocarbon groups (alkyl groups, aryl groups, etc.), alkoxy groups, aryloxy groups, dialkylamino groups, diarylamino groups, etc. It may have a substituent.

Ar ¹ and Ar ² are each an alkyl group such as a methyl group, an ethyl group or a propyl group; an aryl group such as a phenyl group, a naphthyl group or an anthracenyl group; a pyrrolyl group, a thiophenyl group, a furyl group or a carbazolyl group. Which may be the same or different from each other, are preferably an aryl group or an aromatic heterocyclic group, and particularly preferably a phenyl group. These alkyl group, aryl group, and heterocyclic group may have a substituent, and as the substituent, a hydroxyl group; a halogen atom such as a chlorine atom, a bromine atom or an iodine atom; a methyl group, an ethyl group, Alkyl groups such as propyl group, butyl group, hexyl group; alkoxy groups such as methoxy group, ethoxy group, butoxy group; allyl group; aralkyl groups such as benzyl group, naphthylmethyl group, phenethyl group; phenoxy group, triloxy group, etc. Allyloxy group; arylalkoxy groups such as benzyloxy group and phenethyloxy group; aryl groups such as phenyl group and naphthyl group; arylvinyl groups such as styryl group and naphthylvinyl group; dialkylamino groups such as dimethylamino group and diethylamino group A diarylamino group such as a diphenylamino group or a dinaphthylamino group; a dibenzylamino group Group, a diaralkylamino group such as a diphenethylamino group; a diheterocyclic amino group such as a dipyridylamino group or a dithienylamino group; a diallylamino group, or a disubstituted amino group obtained by combining the substituents of the above amino groups. Etc.

R ¹ , R ² , R ³ and R ⁴ are each a hydrogen atom; a halogen atom such as a chlorine atom, a bromine atom or an iodine atom; an alkyl group such as a methyl group, an ethyl group or a propyl group; a methoxy group, Alkoxy groups such as ethoxy group and propyloxy group; Dialkylamino groups such as dimethylamino group; Diarylamino groups such as diphenylamino group; Diaralkylamino groups such as dibenzylamino group; Diheterocyclic amino groups such as dipyridylamino group , Diallylamino group,
Further, it represents a substituted amino group such as a disubstituted amino group which is a combination of the above-mentioned amino group substituents, and these may be the same or different from each other, and a hydrogen atom, a methyl group and a methoxy group are particularly preferable. These alkyl group and alkoxy group may have a substituent, and the substituent includes a hydroxyl group; a halogen atom such as a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl group, a propyl group and a butyl group. Group, alkyl group such as hexyl group; alkoxy group such as methoxy group, ethoxy group, butoxy group; allyl group; aralkyl group such as benzyl group, naphthylmethyl group, phenethyl group; aryloxy group such as phenoxy group and triloxy group; Arylalkoxy groups such as benzyloxy group and phenethyloxy group; aryl groups such as phenyl group and naphthyl group; arylvinyl groups such as styryl group and naphthylvinyl group; dialkylamino groups such as dimethylamino group and diethylamino group;
Diarylamino groups such as diphenylamino groups and dinaphthylamino groups; diaralkylamino groups such as dibenzylamino groups and diphenethylamino groups; diheterocyclic amino groups such as dipyridylamino groups and dithienylamino groups; diallylamino groups and And di-substituted amino groups in which the above-mentioned amino group substituents are combined.

R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰
Are hydrogen atom; alkyl groups such as methyl group, ethyl group, propyl group; aryl groups such as phenyl group, naphthyl group, anthracenyl group; heterocyclic groups such as pyrrolyl group, thiophenyl group, furyl group and carbazolyl group. These may be the same or different from each other. The heterocyclic group is particularly preferably a heterocyclic group having aromaticity. These alkyl group, aryl group, and heterocyclic group may have a substituent, and as the substituent, a hydroxyl group; a halogen atom such as a chlorine atom, a bromine atom or an iodine atom; a methyl group, an ethyl group, Alkyl groups such as propyl group, butyl group, hexyl group; alkoxy groups such as methoxy group, ethoxy group, butoxy group; allyl group; aralkyl groups such as benzyl group, naphthylmethyl group, phenethyl group; phenoxy group, triloxy group, etc. Aryloxy group; arylalkoxy groups such as benzyloxy group and phenethyloxy group; aryl groups such as phenyl group and naphthyl group; arylvinyl groups such as styryl group and naphthylvinyl group; dialkylamino groups such as dimethylamino group and diethylamino group A diarylamino group such as a diphenylamino group or a dinaphthylamino group; a dibenzylamino group Group, a diaralkylamino group such as a diphenethylamino group; a diheterocyclic amino group such as a dipyridylamino group or a dithienylamino group; a diallylamino group, or a disubstituted amino group obtained by combining the substituents of the above amino groups. Etc.

R ⁶ and R ⁷ , R ⁹ and R ¹⁰ are condensed to form a single bond, a methylene group, an ethylene group, a carbonyl group,
A carbocyclic group via a vinylidene group, an ethylenylene group or the like; a heterocyclic group containing an oxygen atom, a sulfur atom, a nitrogen atom or the like may be formed, and those rings may have a substituent. Often, the substituent includes an alkyl group such as a methyl group, an ethyl group and a propyl group; an aryl group such as a phenyl group, a naphthyl group and an anthracenyl group; a cyano group; an alkoxycarbonyl group; an aryloxycarbonyl group; a nitro group;
Examples thereof include halogen atoms such as chlorine atom, bromine atom and iodine atom.

However, R⁶And R⁷A pair consisting of R⁹And R^Ten
The pair consisting of consists of a hydrogen atom or an
When the alkyl group, the other is an aryl group or a heterocyclic group
Is. Y in the general formula [I] is the general formula [III]
In the case of the group represented by^Five, R ⁶, R⁷, R⁸, R⁹Oh
And R^TenMay each have a hydrogen atom or a substituent.
An alkyl group, an aryl group which may have a substituent, or
Represents a heterocyclic group which may have a substituent, and these are mutually
May be the same or different, provided that R⁶And R⁷Empty
R vs. R⁹And R^TenA pair of consists of either pair
When it is a hydrogen atom or an alkyl group, the other of the pair is
A reel group or a heterocyclic group, or R⁶And R
⁷, R⁹And R^TenIs the following general formula [I ′] and general formula [I
In I ′], a carbocyclic group condensed as shown by a dotted line or
May form a heterocyclic group, and those rings are
It may have a substituent, and (1) when X is a hydrogen atom.
Is R⁶And R⁷Are fused to form carbocyclic or heterocyclic groups
And (2) X is a group represented by the general formula [II]
Is R⁶And R⁷A pair consisting of R⁹And R^TenA small pair of
At least one pair is condensed to form a carbocyclic or heterocyclic group.
Forming is preferred.

[0025]

[Chemical 8]

Typical examples of the arylamine compounds represented by the general formula [I] will be given below. These representative examples are shown for the purpose of illustration, and the arylamine compounds used in the present invention are It is not limited to the representative example.

[0027]

[Chemical 9]

[0028]

[Chemical 10]

[0029]

[Chemical 11]

[0030]

[Chemical 12]

[0031]

[Chemical 13]

[0032]

[Chemical 14]

[0033]

[Chemical 15]

[0034]

[Chemical 16]

[0035]

[Chemical 17]

[0036]

[Chemical 18]

[0037]

[Chemical 19]

[0038]

[Chemical 20]

[0039]

[Chemical 21]

[0040]

[Chemical formula 22]

[0041]

[Chemical formula 23]

[0042]

[Chemical formula 24]

[0043]

[Chemical 25]

[0044]

[Chemical formula 26]

[0045]

[Chemical 27]

[0046]

[Chemical 28]

[0047]

[Chemical 29]

[0048]

[Chemical 30]

[0049]

[Chemical 31]

The arylamine compound represented by the above general formula [I] can be produced by a known method. As a preferred production method, the following is a case where -X is -H and
-CR ⁸ which X is represented by the general formula [II] = C (R ⁹⁾ R ¹⁰
Each case will be described.

(1) When -X is -H For example, a known arylamine compound is used as a raw material to carry out a known carbonyl introduction reaction, and then Wit
It is a method of obtaining a target compound by performing a tig reaction. To explain this method in detail, first of all,

[0052]

[Chemical 32]

When R ⁵ = H: General formula [V] (in the general formulas [V] and [VI], Ar ¹ ,
Ar ² , R ¹ , R ² , R ³ , R ⁴ and R ⁵ have the same meanings as in formula [I]. ) In the presence of phosphorus oxychloride, an arylamine compound represented by
When reacted with a formylating agent such as N, N-dimethylformamide or N-methylformanilide, an aldehyde derivative represented by the general formula [VI] is obtained. The formylating agent may be used in a large excess to serve as the reaction solvent, but an inert solvent for the reaction such as O-dichlorobenzene or benzene may be used.

In the case of R ⁵ ≠ H, the arylamine compound represented by the general formula [V] is generally used in the presence of a Lewis acid such as aluminum chloride, iron chloride or zinc chloride in a solvent such as nitrobenzene, dichloromethane or carbon tetrachloride. by reaction with an acid chloride of the formula Cl-CO-R ^5, ketone bodies represented by formula [VI] is obtained.

Then, the obtained aldehyde or ketone represented by the general formula [VI] and N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dioxane, benzene, toluene and the like are inert to the reaction. In a known organic solvent, the general formula [VII] (the general formula [VI
In [I], R ⁶ and R ⁷ have the same meanings as in formula [I], and Q represents a halogen atom such as a chlorine atom or a bromine atom. ) Or a triphenylphosphine, or a halogen compound and a trialkoxyphosphorus compound (R ¹¹ O) ₃ P (R
¹¹ represents an alkyl group such as a methyl group and an ethyl group. ) And a Wittig reagent obtained by reacting
By reacting at a temperature of 0 ° C., preferably 20 to 100 ° C. in the presence of a known basic catalyst such as butyllithium, phenyllithium, sodium methoxide, sodium ethoxide, potassium t-butoxide, the compound of the general formula [I]
A compound represented by

At this time, any of cis isomer, trans isomer, and a mixture of cis isomer and trans isomer is obtained. (In the formula below, the general formula [I] represents any of a cis isomer, a trans isomer, and a mixture of the cis isomer and the trans isomer.)

[0057]

[Chemical 33]

[0058]

[Chemical 34]

For example, it is a method in which a known arylamine compound is used as a raw material, a known carbonyl introduction reaction is carried out, and then a Wittig reaction is carried out to obtain the target compound. To explain this method in detail, first of all,

[0060]

[Chemical 35]

R^Five= R⁸= H, the arylamine compound represented by the general formula [V] is used.
In the presence of phosphorus chlorochloride, N, N-dimethylformamid
Reaction with formylating agents such as N-methylformanilide
Then, the general formula [VIII] (in the formula, Ar¹, Ar²，
R¹, R², R³, R ^Four, R^FiveAnd R⁸Is the general formula
It has the same meaning as in [I]. )
Ludehid body is obtained. Using a large excess of formylating agent
Although it can be used as a reaction solvent, O-dichlorobenze
It is also possible to use an inert solvent for the reaction of benzene, benzene, etc.
Wear.

When R ⁵ ≠ H and R ⁸ ≠ H, the arylamine compound represented by the general formula [V] is added in the presence of a Lewis acid such as aluminum chloride, iron chloride or zinc chloride.
In a solvent such as nitrobenzene, dichloromethane, carbon tetrachloride, etc., the general formula Cl-CO-R ⁵ or Cl-CO-R ⁸
A ketone body represented by the general formula [VIII] is obtained by reacting with an acid chloride represented by Also, R ⁵
And R ⁸ may be the same or different from each other, and R ⁵
The case of ≠ R ⁸ is achieved by mixing the acid chlorides to be added or adding them stepwise.

One of R ⁵ and R ⁸ is a hydrogen atom and the other is not a hydrogen atom. This can be achieved by stepwise performing the synthetic methods in the above two cases.

Then, the obtained aldehyde or ketone represented by the general formula [VIII] and N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dioxane, benzene, toluene and the like are inert to the reaction. In a known organic solvent,

[0065]

[Chemical 36]

The above general formulas [VII] and [IX] (in [IX], R ⁹ and R ¹⁰ have the same meanings as in the general formula [I], and Q is a chlorine atom, a bromine atom or the like. A halogen compound represented by a halogen atom) and triphenylphosphine are allowed to act, or the above halogen compound and a trialkoxyphosphorus compound (R ¹² O) ₃ P (R ¹² is an alkyl group such as a methyl group or an ethyl group. And a Wittig reagent obtained by reacting
Butyllithium, preferably at a temperature of 20-100 ° C.
By reacting in the presence of a known basic catalyst such as phenyllithium, sodium methoxide, sodium ethoxide, potassium t-butoxide, the compound represented by the general formula [I] can be obtained.

At this time, any of cis isomer, trans isomer, and a mixture of cis isomer and trans isomer is obtained. (In the following formula, the general formula [I] represents any of cis isomer, trans isomer, and mixture of cis isomer and trans isomer.) [VII] and [IX] may be used alone or in combination. ,
Moreover, you may make it react stepwise depending on the case.

In these reactions, in some cases,
After each step, or after all steps, recrystallization purification,
It is also possible to obtain a highly purified product by a known purification means such as sublimation purification or column purification. The electrophotographic photoreceptor of the present invention has a photosensitive layer containing one or more arylamine compounds represented by the above general formula [I].

The arylamine compound represented by the general formula [I] exhibits excellent performance as an organic photoconductor. In particular, when it is used as a charge transport medium, it gives a photoreceptor having high sensitivity and excellent durability. Various forms of the photosensitive layer of the electrophotographic photosensitive member are known, and any of them may be used as the photosensitive layer of the electrophotographic photosensitive member of the present invention.

The photosensitive layer (photoconductive layer) is a layered type in which a charge generation layer and a charge transport layer are laminated in this order, or a laminate in which they are laminated in the opposite order. Any structure such as a so-called dispersion type in which the particles of 1) are dispersed can be used. For example, a photosensitive layer in which an arylamine compound and a dye serving as a sensitizer or an electron-withdrawing compound is added to a binder as necessary, a charge-generating material (photoconductive particle) that generates a charge carrier with extremely high efficiency when absorbing light. ) And an arylamine compound in a binder, a photosensitive layer, a charge transport layer composed of an arylamine compound and a binder, and a charge generating material that generates a charge carrier with extremely high efficiency when absorbing light, or from this and a binder. And a charge generation layer that is laminated.

In these photosensitive layers, along with the arylamine compound represented by the general formula [I], other known arylamine compounds, hydrazone compounds, stilbene compounds having excellent performance as organic photoconductors, etc. May be mixed. Among them, in an electrophotographic photoreceptor having at least a photosensitive layer on a conductive substrate, an arylamine compound represented by the above general formula [I] and a pyrenehydrazone represented by the following general formula [X] are provided in the photosensitive layer. An electrophotographic photosensitive member characterized by containing a system compound is preferable.

The electrophotographic photoreceptor containing these two specific compounds in the photosensitive layer has an extremely high photosensitivity and a low residual potential, and the residual potential is hardly accumulated even after repeated use. In addition, it has excellent durability because it has very little change in charging property and sensitivity and extremely good stability, and can be used in high-speed copying machines and printers without any problems.

[0073]

[Chemical 37]

In the general formula [X], R ¹¹ represents an alkyl group, an allyl group, an aryl group or an aralkyl group, and the aryl group and the aralkyl group may have a substituent,
An aryl group which may have a substituent is preferable, and a phenyl group and a naphthyl group are particularly preferable. R ¹² represents an aryl group which may have a substituent, and a phenyl group and a naphthyl group are particularly preferable. Examples of the substituent here include an alkyl group, an allyl group, an alkoxy group, an aryloxy group and a dialkylamino group.

Typical examples of the pyrene hydrazone compounds represented by the general formula [X] are shown below. However, these representative examples are shown for the purpose of illustration, and the pyrene hydrazone compounds used in the present invention are these compounds. It is not limited to the representative example.

[0076]

[Table 1] B-1 1-pyrenecarbaldehyde methylphenyl hydrazone B-21-pyrenecarbaldehyde ethylphenyl
Hydrazone B-3 1-pyrenecarbaldehyde allylphenyl
Hydrazone B-4 1-pyrenecarbaldehyde diphenyl hydrazone B-5 1-pyrenecarbaldehyde benzylphenyl hydrazone B-6 1-pyrenecarbaldehyde-phenyl-1-naphthyl hydrazone B-7 1-pyrenecarbaldehyde-phenyl-2- Naphthyl hydrazone B-8 1-pyrenecarbaldehyde-phenyl 4-methoxyphenyl hydrazone B-9 1-pyrenecarbaldehyde-phenylphenoxyphenyl hydrazone B-10 1-pyrenecarbaldehyde-phenyl-3-methylphenyl hydrazone B-11 1 -Pyrenecarbaldehyde-phenyl-4-methylphenyl hydrazone B-12 1-pyrenecarbaldehyde-phenyl-4-methoxyphenyl hydrazone B-13 1-pyrenecarbaldehyde-phenyl-4-diethyl Mino phenylhydrazone B-14 1-pyrene-carbaldehyde - di - (2-naphthyl) hydrazone

The compounding ratio of the compound represented by the general formula [I] or the general formula [X] is, by weight, usually 95: 5 to 2 or 2.
It is in the range of 0 to 80, but 90 for higher effect
A range of 10 to 40 to 60 is preferred.

The representative examples of particularly preferable combinations of the arylamine compounds represented by the general formula [I] and the pyrenehydrazone compounds represented by the general formula [X] are shown below. The arylamine compounds and pyrenehydrazone compounds used in the present invention are not limited to these representative examples. Representative Examples Representative Examples of the Arylamine Compounds The Pyrenehydrazone Compounds

[0079]

(Table 2) (1) A-18 B-4 (2) A-18 B-6 (3) A-18 B-7 (4) A-18 B-8 (5) A-18 B-10 ( 6) A-18 B-11 (7) A-18 B-12 (8) A-19 B-4 (9) A-19 B-6 (10) A-19 B-7 (11) A-19 B-8 (12) A-19 B-10 (13) A-19 B-11 (14) A-19 B-12 (15) A-20 B-4 (16) A-20 B-6 (17) ) A-20 B-7 (18) A-20 B-8 (19) A-20 B-10 (20) A-20 B-11 (21) A-20 B-12 (22) A-21 B -4 (23) A-21 B-6 (24) A-21 B-7 (25) A-21 B-8 (26) A-21 B-10 (27) A-21 B-11 (28) A-21 B-12 (29) A-22 B-4 (30) A 22 B-6 (31) A-22 B-7 (32) A-22 B-8 (33) A-22 B-10 (34) A-22 B-11 (35) A-22 B-12 ( 36) A-23 B-4 (37) A-23 B-6 (38) A-23 B-7 (39) A-23 B-8 (40) A-23 B-10 (41) A-23 B-11 (42) A-23 B-12 (43) A-24 B-4 (44) A-24 B-6 (45) A-24 B-7 (46) A-24 B-8 (47 ) A-24 B-10 (48) A-24 B-11 (49) A-24 B-12 (50) A-25 B-4 (51) A-25 B-6 (52) A-25 B -7 (53) A-25 B-8 (54) A-25 B-10 (55) A-25 B-11 (56) A-25 B-12 (57) A-26 B-4 (58) A-26 B-6 (59) A-26 B-7 (60) A-2 6 B-8 (61) A-26 B-10 (62) A-26 B-11 (63) A-26 B-12 (64) A-27 B-4 (65) A-27 B-6 ( 66) A-27 B-7 (67) A-27 B-8 (68) A-27 B-10 (69) A-27 B-11 (70) A-27 B-12 (71) A-28 B-4 (72) A-28 B-6 (73) A-28 B-7 (74) A-28 B-8 (75) A-28 B-10 (76) A-28 B-11 (77) ) A-28 B-12 (78) A-29 B-4 (79) A-29 B-6 (80) A-29 B-7 (81) A-29 B-8 (82) A-29 B -10 (83) A-29 B-11 (84) A-29 B-12 (85) A-30 B-4 (86) A-30 B-6 (87) A-30 B-7 (88) A-30 B-8 (89) A-30 B-10 (90) A-3 B-11 (91) A-30 B-12 (92) A-31 B-4 (93) A-31 B-6 (94) A-31 B-7 (95) A-31 B-8 (96 ) A-31 B-10 (97) A-31 B-11 (98) A-31 B-12 (99) A-32 B-4 (100) A-32 B-6 (101) A-32 B -7 (102) A-32 B-8 (103) A-32 B-10 (104) A-32 B-11 (105) A-32 B-12 (106) A-33 B-4 (107) A-33 B-6 (108) A-33 B-7 (109) A-33 B-8 (110) A-33 B-10 (111) A-33 B-11 (112) A-33 B- 12 (113) A-40 B-4 (114) A-40 B-6 (115) A-40 B-7 (116) A-40 B-8 (117) A-40 B-10 (118) A -40 B-11 (119) A-40 B-12

In the present invention, when the arylamine compound represented by the above general formula [I] is used in a charge transport layer of a photosensitive layer comprising two layers of a charge generation layer and a charge transport layer (charge transfer layer), In particular, it is possible to obtain a photoreceptor having a high sensitivity and a small residual potential, and having little variation in surface potential, a decrease in sensitivity, accumulation of residual potential, and the like when repeatedly used, and having excellent durability.

Specifically, usually, a charge generating material is directly vapor-deposited or applied as a dispersion with a binder to form a charge generating layer, and an organic solvent solution containing the arylamine compound is cast thereon, or Alternatively, the charge transporting layer containing the charge transporting material containing the arylamine compound represented by the above general formula [I] is prepared by dissolving the arylamine compound with a binder and coating the dispersion. Although it is a laminated type photoreceptor, the order of laminating the charge generation layer and the charge transport layer may be reversed.

Further, it may be a single-layer type photoreceptor in which the charge generating material and the charge transporting material are dispersed and dissolved in a binder and applied on a conductive support. As the charge generation material, selenium, selenium-tellurium alloy, selenium-arsenic alloy, cadmium sulfide, inorganic photoconductive particles such as amorphous silicon; metal-free phthalocyanine, metal-containing phthalocyanine, perinone pigment, thioindigo, quinacridone, perylene pigment, Examples include organic photoconductive particles such as anthraquinone pigments, azo pigments, bisazo pigments, trisazo pigments, tetrakis azo pigments, and cyanine pigments.

Further, various organic pigments and dyes such as polycyclic quinones, pyrylium salts, thiopyrylium salts, indigo, anthanthrone and pyrantrone can be used. Among them, metal-free phthalocyanine, copper indium chloride, gallium chloride, tin,
Metals such as oxytitanium, zinc, vanadium, or
Azo pigments such as phthalocyanines coordinated with their oxides and chlorides, monoazo, bisazo, trisazo and polyazos are preferable.

Among them, a combination of the metal-containing phthalocyanine and the arylamine compound represented by the above-mentioned general formula [I] gives a photoreceptor having improved sensitivity to laser light, and in particular, at least on a conductive support, In an electrophotographic photoreceptor having a photosensitive layer containing a charge generating material and a charge transporting material, the charge generating material has a main diffraction at a black angle (2θ ± 0.2 °) of 27.3 ° in an X-ray diffraction spectrum. It contains oxytitanium phthalocyanine exhibiting a peak, and as the charge transport material, the compound represented by the general formula [I]
An electrophotographic photoreceptor containing an arylamine compound represented by

The electrophotographic photosensitive member thus obtained has a high sensitivity, a low residual potential and a high charging property, and the fluctuation due to repetition is small, and in particular, the charging stability affecting the image density is good. Therefore, it can be used as a highly durable photoreceptor. Further, since it has a high sensitivity in the region of 750 to 850 nm, it is particularly suitable for a photoconductor for a semiconductor laser printer.

Oxytitanium phthalocyanine used as the charge generating material has a main diffraction peak at 27.3 ° of the black angle (2θ ± 0.2 °) in its X-ray diffraction spectrum. The above-mentioned “main diffraction peak” refers to the peak with the highest (highest) intensity in the X-ray diffraction spectrum. The powder X-ray spectrum of the oxytitanium phthalocyanine used has a black angle (2
The main peak is the diffraction peak at 27.3 °, but there are various variations depending on the detailed conditions, except for the peak intensity at 27.3 °. Of 50% or less is preferable in terms of charging property, sensitivity and the like as an electrophotographic photoreceptor.

The method for producing the oxytitanium phthalocyanine is not particularly limited, but for example, it is produced by the following method. A method for producing a [II] type crystal described in Production Example 1 of JP-A-62-67094. That is, orthophthalodinitrile and a halide of titanium are heated and reacted in an inert organic solvent, and then hydrolyzed. Direct Various crystal forms of oxytitanium phthalocyanine, an organic acid solvent, sulfuric acid or the formula R-SO ₃ H (wherein, R
Represents an aliphatic or aromatic residue which may have a substituent. ) Or a sulfonated compound represented by the formula (1) or, if necessary, a mixed solvent of an insoluble organic solvent and water. If desired, it is dissolved in concentrated sulfuric acid and then released into ice water, or after amorphization by a known method such as mechanical grinding method such as paint shaker, pole mill, sand grind mill, heat treatment with the above sulfonated product or water. Heat treatment with a mixed solvent of an insoluble organic solvent and water. In the case of the treatment with the above-mentioned sulfonated product, it can be produced by using a mechanical grinding method such as a paint shaker, a pole mill and a sand grind mill instead of the heat treatment.

The oxytitanium phthalocyanine particles showing a main diffraction peak at a black angle (2θ ± 0.2 °) of 27.3 ° in the X-ray diffraction spectrum are binder polymers and, if necessary, other organic photoconductive compounds and dyes. The compound is dissolved or dispersed in a solvent together with the electron-withdrawing compound, and the coating solution thus obtained is applied and dried to obtain a charge generation layer. For example, oxytitanium phthalocyanine showing a main diffraction peak at the black angle (2θ ± 0.2 °) 27.3 ° of the X-ray diffraction spectrum and the black angle (2θ ± 0.2 °) 9.3 of the X-ray diffraction spectrum 9.3. °, 13.2
Using oxytitanium phthalocyanine showing major diffraction peaks at °, 26.2 ° and 27.1 °,
Alternatively, the black angle (2θ ±
Oxytitanium phthalocyanine showing a main diffraction peak at 0.2 °) 27.3 ° and a black angle (2θ ± 0.2 °) of X-ray diffraction spectrum 8.5 °, 12.2 °, 1
It is preferable to use dichlorotin phthalocyanine which shows major diffraction peaks at 3.8 °, 16.9 °, 22.4 °, 28.4 ° and 30.1 °.

Examples of dyes and dyes that may be optionally added in the present invention include triphenylmethane dyes such as methyl violet, brilliant green and crystal violet, and thiazine dyes such as methylene blue.
Examples thereof include quinone dyes such as quinizarin, cyanine dyes, pyrylium salts, thiabilylium salts, and benzopyrylium salts. Examples of the electron-withdrawing compound that forms a charge transfer complex with an arylamine compound include, for example, chloranil, 2,3-dichloro-1,4-naphthoquinone, 1-nitroanthraquinone, 1-chloro-5-nitroanthraquinone, and 2 -Quinones such as chloroanthraquinone and phenanthrenequinone; aldehydes such as 4-nitrobenzaldehyde; 9-benzoylanthracene, indandione, 3,5-dinitrobenzophenone, 2,4,7-
Ketones such as trinitrofluorenone, 2,4,5,7-tetranitrofluorenone and 3,3 ′, 5,5′-tetranitrobenzophenone; acid anhydrides such as phthalic anhydride and 4-chloronaphthalic anhydride; Cyano compounds such as tetracyanoethylene, terephthalalmalononitrile, 9-anthrylmethylidene malononitrile, 4-nitrobenzalmalononitrile, 4- (p-nitrobenzoyloxy) benzalmalononitrile; 3-benzalphthalide, 3- (Α-cyano-p-nitrobenzal) phthalide, 3- (α-cyano-p-nitrobenzal) -4,
Examples thereof include electron-withdrawing compounds such as phthalides such as 5,6,7-tetrachlorophthalide.

The charge generation layer in the laminated photosensitive layer contains fine particles of these substances, such as polyester resin, polyvinyl acetate, polyester, polycarbonate, polyvinyl acetoacetal, polyvinyl propional,
It may be used in a dispersion layer in the form of being bound with various binder resins such as polyvinyl butyral, phenoxy resin, epoxy resin, urethane resin, cellulose ester and cellulose ether. Further, examples of the binder resin include polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylic acid ester, methacrylic acid ester, vinyl alcohol and ethyl vinyl ether, polyamide, and silicon resin. In this case, the charge generation material (charge generation substance) is used in an amount of usually 20 to 2000 parts by weight, preferably 30 to 500 parts by weight, more preferably 33 to 500 parts by weight, based on 100 parts by weight of the binder resin. The thickness of the charge generation layer is usually 0.05 to 5 μm, preferably 0.1 μm.
To 2 μm, more preferably 0.15 μm to 0.8 μm
m is preferred. Further, the charge generation layer may contain various additives such as a leveling agent, an antioxidant and a sensitizer for improving the coating property, if necessary. Furthermore, the charge generation layer may be a vapor deposition film of the above charge generation material.

In the case of the dispersion type photosensitive layer, the particle size of the charge generating material needs to be sufficiently small, and it is preferably 1 μm or less, more preferably 0.5 μm or less. The amount of the charge generating material dispersed in the photosensitive layer is, for example, 0.5 to 5
If it is in the range of 0% by weight but too small, sufficient sensitivity cannot be obtained, and if it is too large, there are adverse effects such as a decrease in charging property and a decrease in sensitivity. More preferably, it is used in the range of 1-20% by weight. .

The thickness of the dispersion type photosensitive layer is usually 5 to 50 μm,
It is more preferably used in the range of 10 to 45 μm. Also in this case, known plasticizers for improving film-forming properties, flexibility, mechanical strength, etc., additives for suppressing residual potential, dispersion aids for improving dispersion stability, and coating properties are used. Leveling agents and surface active agents such as silicone oil, fluorine-based oil and other additives may be added for improvement.

Further, the photosensitive layer of the electrophotographic photosensitive member of the present invention may contain a well-known plasticizer in order to improve film-forming property, flexibility and mechanical strength. Therefore, examples of the plasticizer added to the coating solution include phthalic acid esters, phosphoric acid esters, epoxy compounds, chlorinated paraffins, chlorinated fatty acid esters, and aromatic compounds such as methylnaphthalene. When the arylamine compound is used as the charge transport material in the charge transport layer, the coating solution may have the above composition, but the photoconductive particles, dye pigment, electron withdrawing compound, etc. may be removed or added in a small amount. Good. In this case, as the charge generation layer, a coating liquid obtained by dissolving or dispersing in the solvent such as the above-mentioned photoconductive particles and optionally a binder polymer or other organic photoconductive substance, dye pigment, electron-withdrawing compound is applied. Examples thereof include a dried thin layer or a layer formed by film-forming the photoconductive particles.

The thus-formed photoreceptor may also have a barrier layer, an intermediate layer such as an adhesive layer or a blocking layer, a transparent insulating layer, or a protective layer, if necessary, for improving electrical properties and mechanical properties. It goes without saying that it may have a layer for. As the conductive support on which the photosensitive layer is formed, any of those known in electrophotographic photoreceptors can be used. Specifically, for example, aluminum, stainless steel, copper, a drum made of a metal material such as nickel, a sheet or a laminate of these metal foils, a deposit, or aluminum, copper, palladium on the surface,
Examples thereof include a polyester film provided with a conductive layer such as tin oxide and indium oxide, and an insulating support such as paper. Further, there may be mentioned plastic films, plastic drums, papers, paper tubes, etc. which have been subjected to a conductive treatment by coating a conductive material such as metal powder, carbon black, copper iodide, or a polymer electrolyte with a suitable binder. In addition, examples include conductive plastic sheets and drums containing conductive materials such as metal powder, carbon black, and carbon fibers. Further, a plastic film or a belt that has been subjected to a conductive treatment with a conductive metal oxide such as tin oxide or indium oxide can be given.

Of these, an endless pipe made of a metal such as aluminum is a preferable support. As the barrier layer and the intermediate layer, for example, an anodized aluminum film, an aluminum oxide, an inorganic layer such as aluminum hydroxide, polyvinyl alcohol, casein, polyvinylpyrrolidone, polyacrylic acid, celluloses, gelatin, starch, polyurethane, polyimide, polyamide, Etc. are used.

In the electrophotographic photoreceptor of the present invention, the arylamine compound represented by the above general formula [I] is dissolved in a suitable solvent together with a binder according to a conventional method. A coating solution obtained by adding a well-known additive such as an infectious agent, an electron-withdrawing compound, another charge-transporting material, or a plasticizer or a pigment is coated on a conductive support and dried, and usually several times. μ to several tens μ, preferably 1
It can be produced by forming a photosensitive layer having a film thickness of 0 to 45 nm, particularly preferably 27 μm or more. In the case of a photosensitive layer consisting of a charge generation layer and a charge transport layer,
It can be produced by applying the coating liquid on the charge generation layer or forming the charge generation layer on the charge transport layer obtained by applying the coating liquid.

As the solvent for preparing the coating solution, ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene and xylene; N, N-dimethylformamide, acetonitrile, N-methylpyrrolidone,
Aprotic polar solvents such as dimethyl sulfoxide; esters such as ethyl acetate, methyl formate and methyl cellosolve acetate; solvents that dissolve arylamine compounds such as chlorinated hydrocarbons such as dichloroethane and chloroform. Of course, it is necessary to select one that dissolves the binder from these.

As the binder resin used in the charge transport layer in the case of the laminated type photosensitive layer or the binder resin used as the matrix in the case of the dispersed type photosensitive layer,
Good compatibility with the charge transport material, the charge transport material is not crystallized after forming a coating film, or a polymer which does not undergo phase separation, for example, styrene, vinyl acetate, vinyl chloride, acrylic acid ester, methacrylic acid ester, Polymers and copolymers of vinyl compounds such as butadiene, polyvinyl acetal, polycarbonate, polyester, polyester carbonate, polysulfone, polyimide,
Examples thereof include various polymers such as polyphenylene oxide, polyurethane, cellulose ester, cellulose ether, phenoxy resin, silicon resin and epoxy resin, and partially cross-linked cured products thereof can also be used. The amount of the binder used is usually 0.5 with respect to the arylamine compound.
-30 times by weight, preferably 0.7 to 10 times by weight.

In the photosensitive layer containing the arylamine compound represented by the general formula [I] and the pyrenehydrazone compound represented by the general formula [X], the charge transport layer in the laminated type photosensitive layer is basically the same. Specifically, it is composed of an arylamine compound represented by the general formula [I] and a pyrenehydrazone compound represented by the general formula [X] together with a binder resin. The charge generating material described above is dispersed in a matrix containing a compound represented by the general formula [I] or the general formula [X] as a main component.

In this case, the amount of the binder resin used is 0.5 to 3.3 times by weight, preferably 0.5 to 3.3 times the total amount of the compound represented by the general formula [I] and the compound represented by the general formula [X]. It is used in the range of 0.66 to 2.5 times by weight.
Further, the compound represented by the general formula [I] is preferably used in an amount of more than 20% by weight in the charge transport layer in the case of the laminated type or in the photosensitive layer in the case of the dispersed type, in order to obtain a higher effect. More preferably in the range of 25 to 45 weight percent.

In the case of the laminated type photosensitive layer, the charge transport layer may optionally contain various additives such as an antioxidant and a sensitizer, and other charge transport materials. The thickness of the charge transport layer is usually 10 to 60 μm, preferably 10 to 45 μm,
More preferably, it is used with a thickness of 27 to 40 μm. As the outermost surface layer, a conventionally known overcoat layer mainly composed of a thermoplastic or thermosetting polymer may be provided. Usually, the charge transfer layer is formed on the charge generation layer, but the reverse is also possible. As a method for molding each layer, a known method such as sequentially coating a coating solution obtained by dissolving or dispersing a substance contained in the layer in a solvent can be applied.
In addition to the above, various additives for improving the mechanical strength and durability of the coating film can be used in the charge transport layer.

Examples of such additives include well-known plasticizers, various stabilizers, fluidity imparting agents, cross-linking agents and the like. Examples of the coating method of the photosensitive layer include a spray coating method, a spiral coating method, a ring coating method and a dip coating method. Spray coating methods include air spray, airless spray, electrostatic air spray, electrostatic airless spray, rotary atomizing electrostatic spray, hot spray, hot airless spray, etc. Degree,
Considering the adhesion efficiency and the like, in the rotary atomization type electrostatic sprayer, the conveying method disclosed in the republication No. 1-805198 is repeated, that is, the cylindrical work is continuously rotated with no gap in its axial direction. By transporting the electrophotographic photosensitive member, it is possible to obtain an electrophotographic photosensitive member having high adhesion efficiency and excellent film thickness uniformity.

The spiral coating method is described in JP-A-52-
A method using a liquid injection coating machine or a curtain coating machine disclosed in Japanese Patent No. 119651, Japanese Patent Laid-Open No. 231966/1989.
Japanese Patent Laid-Open No. 3-193161 discloses a method using a multi-nozzle body for continuously ejecting paint in a streak pattern from a minute opening.

The dip coating method will be described below. An arylamine compound represented by the above general formula [I],
Suitable total solids concentration is 25 using binder, solvent, etc.
% Or more and more preferably 40% or less, and the viscosity is usually 50 centipoises to 300 centipoises or less, preferably 100 centipoises to 200 centipoises or less, to prepare a coating liquid for forming a charge transport layer. Here, the viscosity of the coating solution is substantially determined by the type of binder polymer and its molecular weight, but if the molecular weight is too low, the mechanical strength of the polymer itself will decrease and the binder polymer will have a molecular weight that does not impair it. Is preferably used. The charge transport layer is formed by the dip coating method using the coating liquid prepared as described above.

Thereafter, the coating film is dried, and the drying temperature time may be adjusted so that necessary and sufficient drying is performed. The drying temperature is usually 100 to 250 ° C., preferably 110 to 17
0 ° C., more preferably 120 to 140 ° C. As a drying method, a hot air dryer, a steam dryer, an infrared dryer, a far infrared dryer or the like can be used.

[0106]

The electrophotographic photosensitive member of the present invention has a very high sensitivity and a small residual potential that causes fogging. Particularly, since light fatigue is small, accumulation of residual potential due to repeated use, surface potential and It is characterized by small fluctuations in sensitivity and excellent durability.

[0107]

EXAMPLES Next, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following production examples and examples as long as the gist thereof is not exceeded. In the examples, “part” means “part by weight”. (Production Example 1) Bis (p-diphenylaminophenoxy)
methane

[0108]

[Chemical 38]

10 g of N, N-dimethylformamide 1
Dissolve in 00 ml, then phosphorus oxychloride 7.0 m
1 was added, and then the mixture was reacted at 65 ° C. for 10 hours. After cooling, the reaction solution was released into 200 g of ice water, hydrolyzed with sodium hydroxide, and then subjected to extraction, concentration and purification treatment by a conventional method to give a yellow oily substance represented by the following structural formula. 6.1 g of a new bisformyl compound was obtained.

[0110]

[Chemical Formula 39]

Production Example 2 3.3 g of the bisformyl compound synthesized in Production Example 1 and 6.8 g of diethyldiphenylmethylphosphonate were added to 55 ml of 1,2-dimethoxyethane.
, And then 1.1 g of 50% sodium hydride
Was added little by little. Then, the mixture was heated under reflux for 7 hours.

After cooling, the reaction solution was discharged into 200 g of ice water,
Further, extraction, concentration, and purification treatments were carried out by a conventional method to obtain 2.7 g of pale yellow crystals (melting point: 110 to 112 ° C). According to the following elemental analysis values and infrared absorption spectrum (FIG. 1), this compound was identified as No. It was found to be an arylamine compound represented by the structural formula of A-21. (Elemental analysis value) As C ₆₅ H ₅₀ N ₂ O ₂

[0113]

[Table 3] C% H% N% Measured value 87.61 5.66 3.14 Measured value 87.90 5.69 3.01 (mass spectrometry measurement result) As C ₆₅ H ₅₀ N ₂ O ₂ MW =
890 M ⁺ = 890

Production Example 3 3.3 g of the bisformyl compound synthesized in Production Example 1 and 6.1 g of 9-dimethylphosphonylfluorene were dissolved in 55 ml of 1,2-dimethoxyethane, and 50% sodium hydride was added. 0.1 g
Added little by little. Then, the mixture was heated under reflux for 7 hours.

After cooling, the reaction solution was discharged into 200 g of ice water,
Further, extraction, concentration and purification treatments were carried out by a conventional method to obtain 2.9 g of yellow crystals (melting point 126-128 ° C). This compound was identified as compound No. 1 from the following elemental analysis values and infrared absorption spectrum (FIG. 2). It was found to be an arylamine compound represented by the structural formula of A-54. (Elemental analysis value) As C ₆₅ H ₄₆ N ₂ O ₂

[0116]

[Table 4] C% H% N% Measured value 88.01 5.23 3.16 Measured value 87.93 5.29 3.14 (mass spectrometric measurement result) C ₆₅ H ₄₆ N ₂ O ₂ MW =
886 M ⁺ = 886

Production Example 4 (Production of Oxytitanium Phthalocyanine Used in Example 51 etc.) 97.5 g of phthalodinitrile was mixed with α-chloronaphthalene 7
Add to 50 ml, then titanium tetrachloride 2 under nitrogen atmosphere
2 ml was added dropwise. After dripping, the temperature is raised, and 200 with stirring.
After reacting at ~ 220 ° C for 3 hours, let stand to cool to 100 ~ 1
The mixture was filtered while hot at 30 ° C., and washed with 200 ml of α-chloronaphthalene heated to 100 ° C. The obtained crude cake,
α-chloronaphthalene 300 ml, then methanol 30
Suspended with 0 ml at room temperature and further 800m methanol
The resulting cake was washed with water for 1 hour several times for 1 hour.
It was suspended in 00 ml and subjected to hot suspension washing for 2 hours.

The pH of the filtrate was 1 or less. The hot water suspension washing was repeated until the pH of the filtrate became 6 to 7. The X-ray diffraction spectrum of the obtained oxytitanium phthalocyanine shows a sharp peak at 27.3 ° at the black angle (2θ ± 0.2 °), but the other peaks are relatively broad peaks.

Example 1 1.0 part of oxytitanium phthalocyanine pigment was added to 14 parts of dimethoxyethane and dispersed with a sand grinder, and then 14 parts of dimethoxyethane and 4-methoxy-4-methylpentanone-2 were added.
14 parts (manufactured by Mitsubishi Kasei Co., Ltd.) are added to dilute, and further,
0.5 parts of polyvinyl butyral (produced by Denki Kagaku Kogyo KK, trade name Denka Butyral # 6000-C) and phenoxy resin (produced by Union Carbide Co., Ltd., trade name U
CAR (registered trademark) PKHH) 0.5 part, dimethoxyethane 6.6 parts, 4-methoxy-4-methylpentanone-
A dispersion liquid was obtained by mixing with a liquid dissolved in 26 parts of the mixed solvent. This dispersion was dried on an aluminum vapor-deposited layer vapor-deposited on a polyester film having a thickness of 75 μm so that the weight after drying was 0.1.
It was coated with a wire bar so as to have a concentration of 4 g / m ² and then dried to form a charge generation layer.

70 parts of the arylamine compound (No. A-21) prepared in Preparation Example 2 and a polycarbonate resin shown below (the following formula is a copolymerized polycarbonate in which the polycarbonate resin is composed of two types of structural units) And that the ratio of these structural units contained in the copolycarbonate is 1: 1.)

[0121]

[Chemical 40]

A coating liquid prepared by dissolving 100 parts in a mixed solvent of 585 parts of tetrahydrofuran and 315 parts of dioxane was applied and dried to form a charge transport layer having a film thickness of 17 μm.
The sensitivity, that is, the half-exposure amount, was 0.36 (μJ / m ² ) measured by the electrophotographic photosensitive member having the photosensitive layer composed of two layers thus obtained.

The half-exposure amount is 50 μm in the dark.
It was obtained by charging with the corona current of A, then exposing with light of 780 nm, and measuring the exposure amount required for the surface potential to decay from 450V to 225V.

(Example 2) A photoconductor prepared in the same manner as in Example 1 except that a naphthalic acid-based bisazo pigment represented by the following structural formula was used in place of the phthalocyanine-based pigment used in Example 1 was subjected to white light. It was 0.75 lux.sec.

[0125]

[Chemical 41]

(Examples 3 to 10) Example 1 was repeated except that the arylamine compound shown in Table 1 below was synthesized in the same manner as in Production Example 2 instead of the arylamine compound used in Example 1. Table 1 shows the sensitivities of the electrophotographic photoconductors prepared in the same manner as in.

[0127]

Table 1 Table 1 Example Exemplified Compound No. Sensitivity (μJ / m ² ) 3 A-1 1.10 4 A-3 0.48 5 A-5 0.47 6 A-11 0.59 7 A-19 0.34 8 A-32 0.359 A-40 0.37 10 A-41 0.76

Examples 11 to 18 Example 2 was repeated except that the arylamine compound shown in Table 2 below was synthesized in the same manner as in Production Example 2 instead of the arylamine compound used in Example 1. Table 2 shows the sensitivities of the electrophotographic photoconductors prepared in the same manner as in.

[0129]

Table 2 Table 2 Example Exemplified Compound No. Sensitivity (lux · sec) 11 A-1 2.30 12 A-3 1.00 13 A-5 0.96 14 A-11 1.34 15 A-19 0.72 16 A-32 0.72 17 A -40 0.75 18 A-41 1.51

Example 19 The procedure of Example 1 was repeated except that the arylamine compound (No. A-54) produced in Production Example 3 was used instead of the arylamine compound used in Example 1. An electrophotographic photoreceptor was obtained. The electrophotographic photosensitive member thus obtained was exposed to light having a wavelength of 780 nm to measure the half-exposure amount, which was 0.38 (μJ / m ² ).

(Example 20) A photoconductor prepared in the same manner as in Example 19 except that the phthalocyanine-based pigment used in Example 19 was replaced with the naphthalic acid-based bisazo pigment used in Example 2 was used. It was 0.77 lux.sec.

Examples 21 to 28 Example 19 was repeated except that the arylamine compounds shown in Table 3 below were synthesized in the same manner as in Production Example 3 instead of the arylamine compounds used in Example 19. Table 3 shows the sensitivities of the electrophotographic photoconductors prepared in the same manner as in.

[0133]

Table 7 Table 3 Example Exemplified Compound No. Sensitivity (μJ / m ² ) 21 A-42 0.68 22 A-43 0.55 23 A-52 0.44 24 A-53 0.41 25 A-55 0.39 26 A-56 0.47 27 A-61 0.50 28 A-63 0.45

(Examples 29 to 36) Example 20 was repeated except that the arylamine compound used in Example 20 was replaced with an arylamine compound shown in Table 4 below, which was synthesized in the same manner as in Production Example 3. Table 4 shows the sensitivities of the electrophotographic photoconductors prepared in the same manner as in.

[0135]

Table 8 Table 4 Example Exemplified Compound No. Sensitivity (lux · sec) 29 A-42 1.40 30 A-43 1.15 31 A-52 0.89 32 A-53 0.85 33 A-55 0.80 34 A-56 0.92 35 A -61 1.03 36 A-63 0.95

Example 37 1.0 part of the naphthalic acid-based bisazo pigment used in Example 2 was added to 14 parts of dimethoxyethane and dispersed with a sand grinder, and then 14 parts of dimethoxyethane and 4-methoxy-4-methyl were added. 14 parts of pentanone-2 (manufactured by Mitsubishi Kasei Co., Ltd.) was added to dilute, and 0.5 part of polyvinyl butyral (manufactured by Denki Kagaku Co., Ltd., trade name Denka Butyral # 6000-C) and phenoxy Resin (Union Carbide Co., Ltd., trade name UCAR (registered trademark)
PKHH) 0.5 part to dimethoxyethane 6.6 parts, 4-
Mixing was performed with a liquid dissolved in a mixed solvent of 6 parts of methoxy-4-methylpentanone-2 to obtain a dispersion liquid. This dispersion is 7
A charge-generating layer was formed on the aluminum vapor-deposited layer vapor-deposited on a polyester film having a thickness of 5 μm by a wire bar so that the weight after drying was 0.4 g / m ² .

On top of this, Exemplified Compound No. A charge transporting layer having a thickness of 40 μm was prepared by applying a coating solution prepared by dissolving 110 parts of the arylamine compound of A-21 and 100 parts of the polycarbonate resin used in Example 1 in a mixed solvent of 302 parts of tetrahydrofuran and 163 parts of dioxane. Was formed.
The electrophotographic photosensitive member having a photosensitive layer composed of two layers thus obtained was mounted on a photosensitive member characteristic measuring instrument [Model EPA-8100 manufactured by Kawaguchi Electric Co., Ltd.] so that the current flowing into the aluminum surface was 72 μA. After being charged to, the exposure and neutralization were performed, and the half-exposure sensitivity (E _1/2 , reference potential 700 V) and residual potential (Vr) at that time were measured. As a result, the half-exposure sensitivity was 0.84 (lux · sec), the residual potential was 8 V, and the chargeability and response speed at low temperatures were excellent, and the running characteristics in actual copying were also good, and 30,000 copies were made. After that, the residual potential did not increase and was stable.

Example 38 Example 37 is repeated except that a naphthalic acid bisazo pigment represented by the following structural formula is used instead of the naphthalic acid bisazo pigment used in Example 37.
When the electrical characteristics of the photoconductor prepared in the same manner as in Example 37 was measured in the same manner as in Example 37, the half-exposure sensitivity was 1.09lux.
-Sec, the residual potential was 7 V, and the chargeability was particularly good under low temperature conditions.

[0139]

[Chemical 42]

(Examples 39 to 44) Electrophotographic sensitizations prepared in the same manner as in Example 37 except that the arylamine compounds shown in Table 5 below were used instead of the arylamine compounds used in Example 37. Table 5 shows the body sensitivity and residual potential.

[0141]

Table 9 Table 5 Example Exemplified compound No. Sensitivity (lux · sec) Residual potential (V) (E _1/2 ) (Vr) 39 A-19 0.79 9 40 A-18 0.76 8 41 A-20 0.79 2 42 A-33 0.3. 95 8 43 A-30 0.93 20 44 A-31 0.93 9

(Examples 45 to 50) An electrophotographic photosensitive member prepared in the same manner as in Example 38 except that the arylamine compounds shown in Table 6 below were used in place of the arylamine compounds used in Example 38. Table 6 shows body sensitivity and residual potential.

[0143]

Table 10 Table 6 Example Exemplified Compound No. Sensitivity (lux · sec) Residual potential (V) (E _1/2 ) (Vr) 45 A-19 1.03 8 46 A-18 0.99 7 47 A-20 1.03 1 48 A-33 1. 24 7 49 A-30 1.21 18 50 A-31 1.218

Example 51 1.0 part of oxytitanium phthalocyanine prepared in Preparation Example 4 was added to 14 parts of dimethoxyethane and dispersed by a sand grinder, and then 14 parts of dimethoxyethane and 4-methoxy-4-methylpentanone. -2 (manufactured by Mitsubishi Kasei Co., Ltd.) was added and diluted, and further 0.5 parts by weight of polyvinyl butyral (manufactured by Denki Kagaku Kogyo KK, trade name Denka Butyral # 6000-C) and phenoxy resin ( Union Carbide Co., Ltd., trade name UCAR (registered trademark) PKHH) 0.5 parts dimethoxyethane 6.6
Part, and 4-methoxy-4-methylpentanone-2 were mixed with a solution prepared by dissolving 6 parts in a mixed solvent with 6 parts to obtain a dispersion liquid. This dispersion was dried on an aluminum vapor-deposited layer vapor-deposited on a polyester film having a thickness of 75 μm, and the weight after drying was 0.4 g / m 2.
After being coated with a wire bar so as to be ² , it was dried to form a charge generation layer.

Furthermore, 70 parts of the arylamine compound represented by the structural formula of Exemplified Compound 21 and 100 parts of the polycarbonate resin used in Example 1 were added to tetrahydrofuran 5
A coating solution dissolved in a mixed solvent of 85 parts and 315 parts of dioxane was applied and dried to form a charge transport layer having a film thickness of 17 μm. The electrophotographic photosensitive member having the two-layered photosensitive layer thus obtained was exposed to light of 780 nm and the half-exposure amount was measured and found to be 0.18 (μJ / m ² ).

(Examples 52 to 59) Electrophotographic photosensitive members were prepared in the same manner as in Example 51 except that the arylamine compounds shown in Table 7 below were used instead of the arylamine compounds used in Example 51. Created. The results of measuring the sensitivity of these electrophotographic photoconductors in the same manner as in Example 51 are shown in Table 7.

[0147]

Table 11 Example 7 Exemplified Compound No. Sensitivity (μJ / m ² ) 52 A-19 0.18 53 A-18 0.20 54 A-20 0.19 55 A-25 0.17 56 A-33 0.20 57 A-30 0.18 58 A-31 0.20 59 A-41 0.20

(Examples 60 to 68) 0.5 parts of oxytitanium phthalocyanine used in Example 51 was used instead of 1.0 part of oxytitanium phthalocyanine used in Example 51.
Part and black angle (2θ ± 0.2 °) 9.3 °, 13.2
An electrophotographic photosensitive member was prepared in the same manner as in Example 51 except that 0.5 part of oxytitanium phthalocyanine showing major diffraction peaks at °, 26.2 ° and 27.1 ° was used. The results of measuring the sensitivity of these electrophotographic photoconductors in the same manner as in Example 51 are shown in Table 8.

[0149]

Table 12 Table 8 Example Exemplified Compound No. Sensitivity (μJ / m ² ) 60 A-21 0.26 61 A-19 0.28 62 A-18 0.26 63 A-20 0.28 64 A-25 0.29 65 A-33 0.28 66 A-30 0.30 67 A-31 0.29 68 A-41 0.29

(Examples 69 to 74) Oxytitanium phthalocyanine 0.3 used in Example 51 was used in place of 1.0 part of oxytitanium phthalocyanine used in Example 51.
Part and black angle (2θ ± 0.2 °) 8.5 °, 12.2
°, 13.8 °, 16.9 °, 22.4 °, 28.4 °
Example 51 except that and 0.7 parts of dichlorotin phthalocyanine showing a main diffraction peak at 30.1 ° were used.
An electrophotographic photoreceptor was prepared in the same manner as in. The results of measuring the sensitivity of these electrophotographic photoconductors in the same manner as in Example 51 are shown in Table 9.

[0151]

Table 13 Example 9 Exemplified Compound No. Sensitivity (μJ / m ² ) 69 A-21 0.29 70 A-18 0.30 71 A-20 0.28 72 A-33 0.30 73 A-31 0.30 74 A-30 0.28

Example 75 10 parts by weight of the bisazo compound used in Example 2 was added to 150 parts by weight of 4-methoxy-4-.
In addition to methylpentanone-2, pulverization and dispersion treatment was performed with a sand grind mill. The pigment dispersion obtained here was added to a 5% 1,2-dimethoxyethane solution of polyvinyl butyral (manufactured by Denki Kagaku Kogyo KK, trade name # 6000-C) to finally obtain a solid content concentration of 4.0%. A dispersion liquid of was prepared.

The dispersion thus obtained has a mirror-finished surface with an outer diameter of 80 mm, a length of 340 mm and a wall thickness of 1.0.
A mm aluminum cylinder was applied by dip coating, and a charge generation layer was provided so that the dry film thickness was 0.4 g / m ² .
Next, 88 parts by weight of the arylamine compound (Exemplified Compound No. A-21) on the charge generation layer and 1-pyrenecarbaldehyde diphenylhydrazone (Exemplified Compound B-
4) 22 parts by weight and 100 parts by weight of a polycarbonate resin (viscosity average molecular weight 22,000) having the following structure:

[0154]

[Chemical 43]

And 1.5 parts by weight of 4- (2,2-dicyanovinyl) phenyl-2,4,5-trichlorobenzenesulfonate are applied by dip coating to a solution prepared by dissolving them in a mixed solvent of 1,4-dioxane and tetrahydrofuran. Then, it is dried at room temperature for 30 minutes and at 125 ° C for 30 minutes, and the film thickness after drying is 3
The charge transport layer was provided so as to have a thickness of 5 μm. When the photoconductor A produced in this manner was mounted on a photoconductor characteristic measuring machine and charged so that the surface potential became −700 V, the half-exposure sensitivity E _1/2 (lux · sec) was 0.66. High sensitivity,
The residual potential was as low as 8V. As a result of repeating durability tests with a copying machine having a commercially available blade cleaning process, a slight increase in residual potential was observed after 100,000 copies, but there was little decrease in potential and there was no change in image quality.

Example 76 Example 76 was carried out except that the amount of the arylamine compound (Exemplified compound A-21) was changed to 70 parts by weight and the amount of 1-pyrenecarbaldehyde diphenylhydrazone (Exemplified compound B-4) was changed to 40 parts by weight. Photoconductor B was prepared and evaluated in the same manner as in Example 75. Half exposure sensitivity E
_1/2 (lux · sec) was 0.66, which showed high sensitivity and residual potential as low as 10 V. The repeated durability test result was also excellent as in Example 75.

Example 77 Example 77 was carried out except that the amount of the arylamine compound (Exemplified compound A-21) was changed to 55 parts by weight and the amount of 1-pyrenecarbaldehyde diphenylhydrazone (Exemplified compound B-4) was changed to 55 parts by weight. Photoconductor C was prepared and evaluated in the same manner as in Example 75. Half exposure sensitivity E
_1/2 (lux · sec) was 0.67 and the sensitivity was high, and the residual potential was a low value of 11 V, and the repeated durability test result was excellent as in Example 75.

(Example 78) Instead of the polycarbonate resin used in Example 37, a polycarbonate resin shown below (the following formula is a copolymerized polycarbonate in which the polycarbonate resin is composed of three types of structural units The ratio contained in the copolymerized polycarbonate of is the following numerical value.)

[0159]

[Chemical 44]

An electrophotographic photosensitive member was prepared in the same manner as in Example 37, except that was used. This electrophotographic photoconductor is a photoconductor characteristic measuring device [Model EPA-810 manufactured by Kawaguchi Electric Co., Ltd.].
0, and the current flowing into the aluminum surface is 72μ
After charging so as to be A, exposure and charge removal were performed, and the half-exposure sensitivity (E _1/2 , reference potential 700 V) and residual potential (Vr) at that time were measured. As a result, half-exposure sensitivity is less than 0.
The residual potential was 85 (lux · sec) and the residual potential was 9V.

(Examples 79 to 84) The arylamine compound used in Example 78 (Exemplified Compound No. A-21)
Table 10 shows the sensitivity and residual potential of the electrophotographic photosensitive member prepared in the same manner as in Example 78 except that the arylamine compounds shown in Table 10 below were used instead of.

[0162]

Table 14 Example 10 Exemplified Compound No. Sensitivity (lux · sec) Residual potential (V) (E _1/2 ) (Vr) 79 A-19 0.79 10 80 A-18 0.77 9 81 A-20 0.80 4 82 A-33 0.3. 96 9 83 A-30 0.93 21 84 A-31 0.94 10

Example 85 Example 78 is repeated except that the naphthalic acid bisazo pigment used in Example 38 is used in place of the naphthalic acid bisazo pigment used in Example 78.
When the electrical properties of the photoconductor prepared in the same manner as in Example 78 were measured, the half-exposure sensitivity was 1.10lux.
-Sec, the residual potential was 8V.

(Examples 86 to 91) The arylamine compound used in Example 78 (Exemplified Compound No. A-21)
Table 11 shows the sensitivity and residual potential of the electrophotographic photoconductor prepared in the same manner as in Example 85 except that the arylamine compounds shown in Table 11 below were used instead.

[0165]

Table 15 Table 11 Example Compound No. Sensitivity (lux · sec) Residual potential (V) (E _1/2 ) (Vr) 86 A-19 1.04 10 87 A-18 0.99 9 88 A-20 1.04 5 89 A-33 1. 25 9 90 A-30 1.21 19 91 A-31 1.22 10

Comparative Example 1 Arylamine compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 37 except that the compound represented by the following structural formula was used in place of
When the electric characteristics were measured in the same manner as in No. 7, the sensitivity (half-exposure amount) was 0.86 (lux · sec) and the residual potential was 45V.
It was found to be high and there was a problem in practical use.

[0167]

[Chemical formula 45]

Comparative Example 2 Arylamine compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 37 except that the compound represented by the following structural formula was used in place of
When the electrical characteristics were measured in the same manner as in No. 7, it was found that the sensitivity (half-exposure amount) was 0.80 (lux · sec) and the residual potential was 120 V, which was extremely high and had a problem in practical use.

[0169]

[Chemical formula 46]

Comparative Example 3 Arylamine compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 37 except that the compound represented by the following structural formula was used in place of
When the electrical characteristics were measured in the same manner as in No. 7, the sensitivity (half-exposure amount) was 0.78 (lux · sec), which was good.
The residual potential was as high as 55 V, and in running characteristics in actual copying, there was a problem that the residual potential increased as the number of copies increased, which proved to be a practical problem.

[0171]

[Chemical 47]

Comparative Example 4 Arylamine compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 38 except that the compound represented by the following structural formula was used in place of
When the electrical characteristics were measured in the same manner as in No. 7, the sensitivity (half-exposure amount) was 1.15 (lux · sec) and the residual potential was 43V.
It was found to be high and there was a problem in practical use.

[0173]

[Chemical 48]

Comparative Example 5 Arylamine Compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 38 except that the compound represented by the following structural formula was used in place of
When the electrical characteristics were measured in the same manner as in No. 7, the sensitivity (half-exposure amount) was 1.06 (lux · sec) and the residual potential was 115V.
It was found to be extremely high and there was a problem in practical use.

[0175]

[Chemical 49]

Comparative Example 6 Arylamine Compound (Exemplified Compound No. A-21)
Example 3 A photoconductor prepared in the same manner as in Example 38 except that the compound represented by the following structural formula was used in place of
When the electric characteristics were measured in the same manner as in No. 7, the sensitivity (half-exposure amount) was 1.01 (lux · sec), which was excellent, but the residual potential was 120 V, which was remarkably high. It was found that there was a problem in practical use in the running characteristics in the live action.

[0177]

[Chemical 50]

Comparative Example 7 Without using the arylamine compound (Exemplified Compound 21),
Comparative Photoreceptor E was prepared and evaluated in the same manner as in Example 75, except that 110 parts by weight of 1-pyrenecarbaldehyde diphenylhydrazone (Exemplified compound B-4) was used. Although the half-exposure sensitivity and the repeated durability test results were good, there was a problem that the value of the residual potential was high.

[Brief description of drawings]

FIG. 1 is an infrared absorption spectrum diagram of the arylamine compound obtained in Production Example 2.

FIG. 2 is an infrared absorption spectrum diagram of the arylamine compound obtained in Production Example 3.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (31) Priority claim number Japanese Patent Application No. 5-7832 (32) Priority date Hei 5 (1993) January 20 (33) Priority claim country Japan (JP) (72) Inventor Hitoshi Ono 1000 Kamoshida-cho, Midori-ku, Yokohama-shi, Kanagawa Sanryo Kasei Co., Ltd. (72) Inventor Tetsuro Murayama 1000 Kamoshida-cho, Midori-ku, Yokohama-shi, Kanagawa Sanryo Kasei Co., Ltd.

Claims (8)

[Claims] 1. On a conductive support, the following general formula [I]:(In the formula, X is a hydrogen atom or a compound represented by the general formula [II]Represents a group represented by the formula; Y is a compound represented by the general formula [III] -OA¹-O- [III] or general formula [IV] -A²-OA³-Represents a group represented by [IV], and in the general formula [III], A¹Is replaced
Represents a divalent hydrocarbon residue which may have a group,
In general formula [IV], A²And A³Each has a substituent
Optionally, an alkylene group, which may have a substituent
Arylene group or alkylene which may have a substituent
A group in which a group and an arylene group which may have a substituent are bonded
Represents A²And A³Whether they are the same or different
Well; Ar ¹And Ar²Each have a substituent
Optionally substituted alkyl group, optionally substituted aryl
Represents a group or a heterocyclic group which may have a substituent.
May be the same or different from each other; R¹, R²，
R³And R^FourAre hydrogen atom, halogen atom, and
Alkyl group which may have a substituent, which may have a substituent
Represents a good alkoxy group or substituted amino group,
May be the same or different from each other; R^Five, R⁶, R
⁷, R⁸, R⁹And R^TenAre the hydrogen atom and
Alkyl group which may have a substituent, which may have a substituent
Shows an aryl group or a heterocyclic group which may have a substituent.
However, these may be the same or different from each other,
Kuha R⁶And R⁷, R⁹And R^TenAre condensed to form a carbocyclic group or
A heterocyclic group may be formed, provided that R⁶And R⁷From
Naru pair, R⁹And R^TenIs a pair consisting of one of each pair
When is a hydrogen atom or an alkyl group, the other is
Or a heterocyclic group. ) Ally
Characterized by having a photosensitive layer containing a ruamine-based compound
A photoconductor for electrophotography. 2. A photosensitive layer comprising a conductive support and an arylamine compound represented by the general formula [I] and a pyrenehydrazone compound represented by the following general formula [X]. The electrophotographic photoreceptor according to claim 1. [Chemical 3] (In the formula, R ¹¹ represents an alkyl group, an allyl group, an aryl group or an aralkyl group, the aryl group and the aralkyl group may have a substituent, and R ¹² represents an aryl which may have a substituent. Represents a group.) 3. An arylamine compound represented by the general formula [I] is contained as a charge transporting material on a conductive support, and a black angle (2θ ± 0.2 °) of an X-ray diffraction spectrum is used as a charge generating material. The electrophotographic photoreceptor according to claim 1, further comprising a photosensitive layer containing oxytitanium phthalocyanine showing a main diffraction peak at 27.3 °. 4. The electrophotographic photosensitive material according to claim 1, wherein Y in the general formula [I] is a group represented by the general formula [III]. body. 5. A ¹ in the general formula [III] may have an alkylene group which may have a substituent, an arylene group which may have a substituent, or a substituent which may have a substituent. 3. A group in which a good alkylene group and an arylene group which may have a substituent are bonded to each other.
Alternatively, the electrophotographic photoreceptor according to claim 3. 6. The Y in the general formula [I] is a group represented by the general formula [IV].
The electrophotographic photoreceptor according to claim 2 or 3. 7. Y in the general formula [I] is a group represented by the general formula [III], and R ⁵ , R ⁶ , R ⁷ ,
R ⁸ , R ⁹ and R ¹⁰ are each a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. Which may be the same or different from each other, provided that R ⁶
A pair consisting of R ^7, the pair consisting of R ⁹ and R ^10, when either one of a hydrogen atom or an alkyl group of each pair, the other, and wherein an aryl group or a heterocyclic group, The electrophotographic photosensitive member according to claim 1, claim 2, or claim 3. 8. Y in the general formula [I] is a group represented by the general formula [III]; R ⁵ , R ⁶ , R ⁷ ,
R ⁸ , R ⁹ and R ¹⁰ are each a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. Which may be the same or different from each other, provided that R ⁶
And a pair consisting of R ⁷ and a pair consisting of R ⁹ and R ¹⁰ , when one of each pair is a hydrogen atom or an alkyl group, the other of the pair is an aryl group or a heterocyclic group, or , R ⁶ and R ⁷ , R ⁹ and R ¹⁰ may be condensed to form a carbocyclic group or a heterocyclic group, and those rings may have a substituent, and (1) X is When it is a hydrogen atom,
R ⁶ and R ⁷ are condensed to form a carbocyclic group or a heterocyclic group, and when (2) X is a group represented by the general formula [II], a pair consisting of R ⁶ and R ⁷ , R ⁹ 4. The electrophotographic photoreceptor according to claim 1, wherein at least one of the pair consisting of R ¹⁰ and R ¹⁰ is condensed to form a carbocyclic group or a heterocyclic group.