JPH03163460A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body having high sensitivity by forming a photosensitive layer contg. a specified hydrazone compd. on an electrically conductive substrate. CONSTITUTION:A photosensitive layer contg. a hydrazone compd. represented by the formula is formed on an electrically conductive substrate. In the formula, A is aryl which may have a substituent or a heterocyclic group which may have a substituent, each of R<1>, R<2> and R<5> is H or aryl which may have a substituent, each of R<4> and R<5> is H, halogen, alkyl which may have a substituent, alkoxy which may have a substituent aryl which may have a substituent, aryloxy which may have a substituent or nitro and R<6> is H, halogen, alkyl which may have a substituent or alkoxy which may have a substituent.

Description

[Detailed description of the invention] <Industrial application field> The present invention relates to a photoreceptor for electrophotography.

More specifically, it relates to a highly sensitive electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive substance. Conventional technology> Conventionally, the photosensitive layer of an electrophotographic photoreceptor contains selenium and carbon sulfide.
Inorganic photoconductive materials such as aluminum and zinc oxide were widely used. However, selenium and cadmium sulfide need to be recovered as toxic substances; selenium crystallizes when exposed to heat and has poor heat resistance; cadmium sulfide and zinc oxide have poor moisture resistance; and zinc oxide has poor printing durability. However, efforts are still being made to develop new photoreceptors. Recently, research has progressed on the use of organic photoconductive substances in photosensitive layers of electrophotographic photoreceptors, and some of them have been put into practical use. Organic photoconductive materials have advantages over inorganic materials, such as being lightweight, easy to form a film, easy to manufacture photoreceptors, and depending on the type, transparent photoreceptors can be manufactured. have. Recently, so-called functionally separated photoreceptors, in which the functions of generating and transporting charge carriers are shared by separate compounds, have become the mainstream in development because they are effective in increasing sensitivity.
Organic photoreceptors of this type are also being put into practical use. As the charge carrier transfer medium, a polymeric photoconductive compound such as polyvinylcarbazole may be used, or a low molecular weight photoconductive compound may be dispersed and dissolved in a binder polymer.

Problems to be Solved by the Invention In particular, for organic low-molecular photoconductive compounds, polymers with excellent film properties, flexibility, adhesive properties, etc. can be selected as binders, so it is easy to improve mechanical properties. However, it was difficult to find a compound suitable for making a highly sensitive photoreceptor. <Means for Solving the Problems> The present inventors conducted intensive research on organic low-molecular photoconductive compounds that provide electrophotographic photoreceptors with high sensitivity and high durability, and found that specific hydrazone compounds are suitable. We discovered that this is the case and arrived at the present invention. That is, the gist of the present invention is to provide the general formula (1)...(1) (wherein A is an aryl group which may have a substituent, or
Represents a heterocyclic group which may have a substituent, and Rl. Rt
and Bs represent a hydrogen atom, an alkyl group that may have a substituent, or an aryl group that may have a substituent, and these may be the same or different from each other, and R3 and R
4 is a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an alkoxy group that may have a substituent, an aryl group that may have a substituent, and a group that may have a substituent. Represents a ryloxy group or a nitro group, which may be the same or different from each other, and R6 is a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, or a substituent. represents an alkoxy group, R7 is an alkyl group which may have a substituent, an aryl group which may have a substituent, an allyl group, an aralkyl group which may have a substituent,
The following general formula (
If) represents a group forming any of the rings shown in (V), Cri) CIIN3 (IVI (V) n represents an integer of 1 or 2. However, A and R1 are integral with each other. The present invention relates to an electrophotographic photoreceptor characterized by having a photosensitive layer containing a hydrazone compound represented by the following formula.

<Function> The present invention will be described in detail below. The electrophotographic photoreceptor of the present invention contains a hydrazone compound represented by the above general formula (1) in the photosensitive layer.

In the general formula (1), A is benzene, naphthalene, anthracene, pyrene, perylene, phenanthrene,
Aryl groups derived from fluoranthene, acenaphthene, acenaphthylene, azulene, fluorene, indene, tetralin, naphthacene, etc.; virol, thiophene,
Represents a complex I52M derived from furan, indole, carbazole, birazole, biridine, acridine, phenazine, penzothiophene, henzofuran, xanthene, thioxanthe, indoline, phenothiazine, tetrahydroquinoline, etc. These aryl groups and heterocyclic groups may have a substituent, and examples of the substituent include 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 proyl group, and a butyl group. alkyl groups such as methoxy, ethoxy, butoxy groups; allyl groups; aralkyl groups such as benzyl, naphthylmethyl and phenethyl groups; aryloxy such as phenoxy and trioxy groups groups; arylalkoxy groups such as benzyloxy and phenethyloxy groups; aryl groups such as phenyl and naphthyl groups; arylvinyl groups such as styryl and naphthylvinyl groups; dialkylapolyno groups such as dimethylamino and jetylamino groups; Diarylamino groups such as diphenylamino and dinaphthylamino groups; dialkylamino groups such as dibenzylamino and diphenethylamino; dipyridylamino groups;
Examples include diheterocyclic amino groups such as dichenylamino groups; diallylamino groups, etc. R+. Rt and R% are hydrogen atoms; alkyl groups such as methyl group, ethyl group, proyl group, butyl group, hexyl group;
It represents an aryl group such as a phenyl group or a tolyl group, and these may be the same or different from each other. Further, these alkyl groups and aryl groups may have a substituent, and examples of the substituent include 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 proyl group, a butyl group, Alkyl groups such as hexyl groups; alkoxy groups such as methoxy, ethoxy, and butoxy groups; allyl groups; aralkyl groups such as benzyl, naphthylmethyl, and phenethyl groups; aryloxy groups such as phenoxy and triloxy groups;
Arylalkoxy groups such as benzyloxy and phenethyloxy groups; Aryl groups such as phenyl and naphthyl groups; Arylpinyl groups such as styryl and naphthylvinyl groups; Dialkylamino groups such as dimethylamino and diethylamino groups; diphenylamino groups; Diarylamino groups such as dinaphthylamino groups; dialkylamino groups such as dibenzylamino groups and diphenethylamino groups; diheterocyclic amino groups such as dibyridylamino groups and dichenylamino groups; and diallylamino groups.

R3 and R4 are hydrogen atoms; halogen atoms such as chlorine, bromine, iodine; alkyl groups such as methyl, ethyl, proyl, butyl, hexyl; methoxy, ethoxy, butoxy, etc. Represents an alkoxy group; an aryl group such as a phenyl group or a tolyl group; an aryloxy group such as a phenoxy group or a triloxy group; or a nitro group, and these may be the same or different from each other. In addition, these alkyl groups, alkoxy groups, aryl groups, and aryloxy groups may have a substituent, and examples of the substituent include a hydroxyl group; a halogen atom such as a chlorine atom, a bromine atom, and an iodine atom; a methyl group, an ethyl group; , alkyl groups such as probyl group, butyl group, hexyl group; alkoxy groups such as methoxy group, ethoxy group, putoxy group; allyl group; aralkyl group such as benzyl group, naphthylmethyl group, phenethyl group; phenoxy group,
Aryloxy groups such as triloxy groups; arylalkoxy groups such as benzyloxy groups and phenethyloxy groups; aryl groups such as phenyl groups and naphthyl groups; aryl vinyl groups such as styryl groups and naphthylvinyl groups; dimethylamino groups and diethyla ξ dialkylamino groups such as diphenylamino groups, dinaphthylamino groups; dialkylamino groups such as dibenzylamino groups and diphenethylamino groups; diheterocyclic amino groups such as dipyridylamino groups and dichenylamino groups Group; examples include diallylamino group.

R6 is 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, a probyl group, a butyl group, or a hexyl group; an alkoxy group such as a methoxy group, an ethoxy group, or a butoxy group These alkyl groups and alkoxy groups may have a substituent, and the substituents include hydroxyl group; halogen atoms such as chlorine atom, bromine atom, and iodine atom; methyl group, ethyl group, proyl group, butyl group. and alkyl groups such as hexyl group; alkoxy groups such as methoxy group, ethoxy group, butoxy group, and the like.

R7 is an alkyl group such as methyl group, ethyl group, probyl group, butyl group, hexyl group; phenyl group, naphthyl group; tolyl group, methoxynaphthyl group, anthryl group, acenaphthyl group, fluorenyl group, biphenyl group, styryl group, etc. Aryl group; Allyl group; Aralkyl group such as benzyl group, naphthylmethyl group, phenethyl group; Heterocyclic group derived from pyrrole, thiophene, furan, indole, birazole, pyridine, etc.; Phenyl group bonded to nitrogen atom, bond represents a group representing a ring shown in the following general formulas (n) to [V]. [■) [111] (IV)
(V) These alkyl groups, aryl groups, aralkyl groups, and heterocyclic groups may have a substituent, and the substituents include hydroxyl group; halogen atom such as chlorine atom, bromine atom, and iodine atom; methyl group , alkyl groups such as ethyl group, puchyl group, butyl group, hexyl group; alkoxy groups such as methoxy group, ethoxy group, butoxy group; allyl group; aralkyl group such as benzyl group, naphthylmethyl group, phenethyl group; phenoxy aryloxy groups such as triloxy groups; arylalkoxy groups such as benzyloxy groups and phenethyloxy groups; aryl groups such as phenyl groups and naphthyl groups; aryl vinyl groups such as styryl groups and naphthyl vinyl groups; dimethylamino groups, Diarylamino groups such as diethylamino groups; diarylamino groups such as diphenylamino and dinaphthylamino groups; dialkylamino groups such as dibenzylamino and diphenethylamino; diheterocyclic amino groups such as dipyridylamino and dichenylamino groups Base;
Examples include diallylamino group.

n represents an integer of 1 or 2.

However, A and R' may be combined to form a ring.

An example of this is etc. can be mentioned.

In the above formula, R@ represents a hydrogen atom, an alkyl group, an allyl group, an aralkyl group, or an aryl group. The above general formula (I
) can be produced using known methods. A preferred production method is, for example, condensing raw materials aldehydes or ketones and halogenated methylthiophenes using Wittig reaction, then formylation using Willsmeyer reaction, and further condensation by reaction with desired hydrazine. , a method for obtaining the desired compound.

To explain this method in detail, first, as shown in the reaction formula below, general formula [■] (In the above formula, A and R' are general formula (1
) have the same meaning.

The same applies to the following expressions. ) with an aldehyde or ketone represented by the general formula [ (2) (In the above formula, R'', R'', R' and n have the same meanings as in general formula (13), and X represents a halogen atom such as a chlorine atom or a bromine atom.

The same applies to the following formulas. ) and Wittig reagent obtained by reacting the halide represented by
A compound represented by the general formula [■] can be obtained by reacting it at a temperature of 00°C in the presence of a known basic catalyst such as butyllithium, phenyllithium, sodium methoxide, sodium ethoxide, potassium, and mu-L-ptoxide. is obtained as a mixture of cis-trans isomers. Although the compound represented by the general formula (■) can be used in either cis or trans isomer form, it is preferable to use the mixture as a mixture in the next reaction without separating each isomer. (V[) [■] [■] Next, a carbonyl group is introduced into the condensate represented by the general formula [■], but the production method differs depending on whether RS is H or other than H. Each is described below.

(When R' = H) When the condensate represented by the general formula [■] is reacted with a formylating agent such as N,N-dimethylformamide or N-methylformanilide in the presence of phosphorus oxychloride, An aldehyde compound represented by the general formula [■] (in the formula, R5 represents a hydrogen atom) is obtained. Although the formylating agent can be used in large excess to serve as a reaction solvent, a non-reactive solvent such as O-dichlorobenzene or benzene may also be used.

[■] (IX) (RS = H) (When R5≠H) The condensate represented by the general formula [■] is mixed with nitrobenzene, dichloromethane, In a solvent such as carbon tetrachloride, general formula [X] (In the above formula, R% is a general formula other than a hydrogen atom (
It has the same meaning as in 1). ), a ketone body represented by general formula (IX) is obtained. (IX) (RS ≠H) Next, general formula [■] (In the above formula, R5 is general formula [1]
It has the same meaning as in . The same applies to the following formulas. ) Aromatic hydrocarbons such as benzene, toluene and chlorobenzene; Alcohols such as methanol, ethanol and butanol; Tetrahydrofuran, 1,2-dimethoxyethane, l,4-
Ethers such as dioxane; cellosolves such as methyl cellosolve and ethyl cellosolve. The following general formula (XI) (in the above formula, Rh and R' are the same as in the above general formula (1) hydrazine or its hydrochloride or sulfate represented by
A compound represented by general formula (1) can be obtained by reacting at a temperature of 200°C, preferably 20 to 100°C.

In order to accelerate the reaction, p-toluenesulfonic acid, hensensulfonic acid, hydrochloric acid, sulfuric acid, potassium acetate, sodium acetate, etc. may be added depending on the case. (Xll (N) In these reactions, it is possible to obtain a highly purified product by known purification means such as recrystallization, sublimation, and columns, depending on the case, after each step or after all steps.

The electrophotographic photoreceptor of the present invention has a photosensitive layer containing one or more hydrazone compounds represented by the above general formula (1). The hydrazone compound represented by the general formula (1) exhibits extremely excellent performance as an organic photoconductor. Particularly when used as a charge transfer medium, it provides a photoreceptor with high sensitivity and excellent durability.

Various forms of the photosensitive layer of an electrophotographic photoreceptor are known, and the photosensitive layer of the electrophotographic photoreceptor of the present invention may be any of them.

For example, a photosensitive layer containing a hydrazone compound in a binder and, if necessary, a dye or electron-withdrawing compound as a sensitizer, and a photoconductive particle and hydrazone compound that generate charge carriers with extremely high efficiency when absorbing light. a photosensitive layer in which a hydrazone compound and a binder are added, a charge transfer layer made of a hydrazone compound and a binder, and a charge generation layer made of photoconductive particles that generate charge carriers with extremely high efficiency when absorbing light, or a charge generation layer made of photoconductive particles and a binder. Examples include laminated photosensitive layers. In these photosensitive layers, other known hydrazone compounds and stilbenzene compounds having excellent performance as organic photoconductors may be mixed together with the hydrazone compound represented by the general formula (1).

In the present invention, when the hydrazone compound represented by the above general formula (1) is used in the charge transfer layer of a photosensitive layer consisting of two layers, a charge generation layer and a charge transfer layer, it has particularly high sensitivity and low residual potential. In addition, it is possible to obtain a photoreceptor with excellent durability, with little variation in surface potential, decrease in sensitivity, accumulation of residual potential, etc. when used repeatedly. The electrophotographic photoreceptor of the present invention can be prepared using the general formula (
A hydrazone compound represented by 1) is dissolved in a suitable solvent together with a binder, and if necessary, a photoconductive particle, a sensitizing dye, an electron-withdrawing compound, which generates charge carriers with extremely high efficiency when absorbing light, or , a coating solution obtained by adding plasticizers, pigments, and other additives is applied onto a conductive support and dried to form a photosensitive layer with a thickness of usually several micrometers to several tens of micrometers. be able to. In the case of a photosensitive layer consisting of two layers, a charge generation layer and a charge transfer layer,
It can be manufactured by applying the above-mentioned coating liquid onto the charge-generating layer, or by forming the charge-generating layer on the charge transfer layer obtained by applying the above-mentioned coating liquid.

Examples of solvents for preparing the coating solution include tetrahydrofuran, 1.
Ethers such as 4-dioxane; methyl ethyl ketone,
Ketones such as cyclohexanone; aromatic hydrocarbons such as toluene and xylene. Aprotic polar solvents such as N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, and dimethyl sulfoxide; Esters such as ethyl acetate, methyl formate, and methyl cellosolve acetate; Hydrazones such as chlorinated hydrocarbons such as dichloroethane and chloroform Examples include solvents that dissolve the system compounds. Of course, it is necessary to select one that dissolves the binder from among these. In addition, as a binder, polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylic esters, methacrylic esters, and phthadiene, polyvinyl acecool, polycarbonate, polyester, polysulfone, polyphenylene oxide, Examples include various polymers that are compatible with styrene compounds, such as polyurethane, cellulose ester, cellulose ether, phenoxy resin, silicone resin, and epoxy resin. The amount of binder used is usually 0.5 to 30 times the hydrazone compound, preferably 0.5 to 30 times the hydrazone compound. 7-1
The range is 0 times the weight. As the photoconductive particles, dyes, and electron-withdrawing compounds to be added to the photosensitive layer, well-known ones can be used. Photoconductive particles that generate charge carriers with extremely high efficiency when absorbing light include inorganic photoconductive particles such as selenium, selenium-tellurium alloy, selenium-arsenic alloy, cadmium sulfide, and amorphous silicon; metal-containing cyanine, and perinone. Examples include organic photoconductive particles such as thioindigo, quinacridone, berylene pigments, anthraquinone pigments, azo pigments, bisazo pigments, trisazo pigments, tetrakis azo pigments, and cyanine pigments. (In particular, when combined with metal-containing cap cyanine, a photoreceptor with improved sensitivity to laser light can be obtained.) Examples of dyes include triphenylmethane dyes such as methyl violet, brilliant green, and crystal violet, and thiazine dyes such as methylene blue. , quinone dyes such as quinizarin, cyanine dyes, biryllium salts, thiavirylium salts, penzovirilium salts, and the like. In addition, as electron-withdrawing compounds that form charge transfer complexes with hydrazone compounds,
For example, chloranil, 2,3-dichloro-1,4-naphthoquinone, ■-nitroanthraquinone, 1-chloro-5-
Quinones such as nitroanthraquinone, 2-chloroanthraquinone, and phenanthrenequinone; Aldehydes such as 4-nitrobenzaldehyde; 9-penzoylanthracene, indanedione, 3,5-dinitropenzophenone, 2,4.7-} Rinitrofluorenone, 2.4,5.
7-tetranitrofluorenone, 3.3',5.5'-
Ketones such as tetranitrobenzophenone; acid anhydrides such as phthalic anhydride and 4-chloronaphthalic anhydride; tetracyanoethylene, terephthalalmalononitrile, 9-anthrylmethylidenemalononitrile, 4-nitrobenzalmalononitrile Cyano compounds such as nitrile, 4-(p-nitrobenzoyloxy)penzalmalononitrile; 3-penzalphthalide, 3-(α-cyano-p-nitrobenzal)phthalide, 3-(α-cyano-p-nitrobenzal)
Examples include electron-withdrawing compounds such as phthalides such as -4.5,6.7-tetrachlorophthalide.

Further, the photosensitive layer of the electrophotographic photoreceptor of the present invention may contain a well-known plasticizer in order to improve film resistance, flexibility, and mechanical strength. For this purpose, the plasticizers added to the above coating solution include phthalate esters, phosphate esters,
Examples include epoxy compounds, chlorinated paraffins, chlorinated fatty acid esters, and aromatic compounds such as methylnaphthalene. When using a hydrazone compound as a charge transfer medium in the charge transfer layer, the coating liquid may have the above composition, but photoconductive particles, dyes, electron-withdrawing compounds, etc. may be excluded or added in small amounts. ．． In this case, the charge generation layer was prepared by coating and drying a coating solution obtained by dissolving or dispersing the above-mentioned photoconductive particles in a solvent such as a binder polymer, an organic photoconductive substance, a dye, an electron-withdrawing compound, etc. as necessary. Examples include a thin layer, or a layer formed by enclosing the photoconductive particles by means such as binding.

It goes without saying that the photoreceptor formed in this way may also have an adhesive layer, an intermediate layer, a transparent insulating layer, etc., if necessary. As the conductive support on which the photosensitive layer is formed, any of those used in well-known electrophotographic photoreceptors can be used.

Specific examples include metal drums and sheets made of aluminum, stainless steel, copper, etc., and laminates and vapor deposits of these metal foils. Further examples include plastic films, plastic drums, paper, paper tubes, etc., which are coated with a conductive substance such as metal powder, carbon black, copper iodide, or polymer electrolyte together with a suitable binder to conductivity treatment. Other examples include plastic sheets and drums that contain conductive substances such as metal powder, carbon black, and carbon fibers and are made conductive. <Effects of the Invention> The electrophotographic photoreceptor of the present invention has extremely high sensitivity and has a low residual potential that causes fogging, and is particularly resistant to optical fatigue, so that it does not accumulate residual potential due to repeated use, and has a low residual potential that causes fogging. It has the characteristics of small sensitivity fluctuations and excellent durability.

<Examples> Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following production examples and Examples unless the gist thereof is exceeded. In the examples, "part F" indicates "part J by weight."

Production Example 1 25g of dried N,N-dimethylformamide 250
mI! ．． Then, 37 g of triphenylphosphine was added and reacted to combine the Wittig reagent. Next, 27 g of triphenylamine aldehyde was added to the reaction system, and 41 g of a 28% methanol solution of sodium methylate was added dropwise, followed by reaction at 70° C. for 1 hour and 30 minutes. After cooling, the reaction solution was poured into ice water at 500 ml.
35 g of a known styrenic compound was obtained by further performing filtration and purification using conventional methods.

Production Example 2 15 g of the styrene compound obtained in Production Example 1 and 10 g of phosphorus oxychloride were mixed with 300 g of N,N-dimethylformamide.
The reaction was carried out at 70° C. for 3 hours in mf.

After cooling, the reaction solution was poured into 300 g of ice water, hydrolyzed with sodium hydroxide, and further treated in a conventional manner. separation, concentration,
By performing purification treatment, 10 g of brown viscous liquid was obtained. This compound was found to be a styrene-based compound having a formyl group represented by the following structural formula based on the following elemental analysis, mass spectrometry, and infrared absorption spectrum measurements. (Elemental analysis value) As C■}I+vONS (Mass spectrometry measurement result) As CtsHrqONS MW = 38 1 M'' = 381 Production Example 3 2.5 g of the styrene compound having a formyl group synthesized in Production Example 2 and 1.1- 72.6 g of diphenyl hydrazi was reacted in a mixed solvent of 25 mf of methyl alcohol and 10 ml of chloroform under heating under reflux for 30 minutes.

After cooling, the reaction solution was concentrated and further purified by a conventional method to obtain 2.1 g of orange crystals (melting point 78-80).
°C) was obtained.

This compound was found to be a hydrazone compound represented by the following structural formula by the following elemental analysis values, mass spectrometry measurements, and infrared absorption spectrum measurements (Fig. 1).

(Elemental analysis value) Cs, HzqNs As S (Mass spectrometry measurement result) C, J7 HzqN MW as 3S = 547 M''' = 5 4 7 Example 1 0.4 part of ditanium oxyphthalocyanine pigment and polyvinyl 0.2 parts of butyral (manufactured by Sekisui Chemical Co., Ltd., trade name S-LEC BH-3) and 0.2 parts of phenoxy resin (manufactured by Union Carbide, trade name PKHH) were mixed into 30 parts of 4-
Dispersion and pulverization treatment was performed in methoxy-4-methylpentanone-2 (manufactured by Mitsubishi Kakai Corporation). The weight of this dispersion after drying was 0.2 g on the Al ξ vapor deposited layer on a polyester film with a film thickness of 75 μm.
/m" with a wire bar, and dried to form a charge generation layer. On top of this, 90 parts of the hydrazone compound produced in Production Example 3 and polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd.) were applied. Manufactured by company, product name Yubilon E-2000) 1
00 parts dissolved in 900 parts of dioxane is applied.
It was dried to form a charge transfer layer with a thickness of 17 μm.

When the sensitivity, that is, the half-decreased exposure of the electrophotographic photoreceptor having the two-layer photosensitive layer thus obtained was measured, it was 2.6 (μW/cm'')-'. It was determined by charging the body in the dark with a corona discharge of -4.8 KV, then exposing it to 775 nm light, and measuring the amount of exposure required for the surface potential to decay from 500 V to 250 V.

Example 2 A photoreceptor was prepared in the same manner as in Example 1 using a naphthalic acid-based bisazo pigment represented by the following structural formula in place of the cyanine-based pigment used in Example 1. When the exposure amount was measured, 1. 1 lux-s
It was ee.

Examples 3 to 18 Instead of the hydrazone compound used in Example 1, the hydrazone compound shown in Table 1 below, which was synthesized in the same manner as in Production Example 3, was used. The sensitivity of the electrophotographic photoreceptor obtained using the titanium oxyphthalocyanine pigment used in Example 1 is shown in the table below.

[Brief explanation of the drawing]

Figure 1 shows the infrared absorption spectrum of the hydrazone compound obtained in Production Example 3. Mitsubishi Kakai Co., Ltd.

Claims (1)

[Claims] (1) General formula [I] ▲Mathematical formula, chemical formula, table, etc. are present on the conductive support▼...[I] (In the formula, A is an aryl group that may have a substituent, or
Represents a heterocyclic group that may have a substituent, R^1, R^2
and R^5 represent a hydrogen atom, an alkyl group that may have a substituent, or an aryl group that may have a substituent, and these may be the same or different from each other, and R^3 and R^ 4 is a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an alkoxy group that may have a substituent,
Represents an aryl group that may have a substituent, an aryloxy group that may have a substituent, or a nitro group, which may be the same or different from each other, and R^6 is a hydrogen atom,
Represents a halogen atom, an alkyl group that may have a substituent, or an alkoxy group that may have a substituent, and R^7 represents an alkyl group that may have a substituent, or an alkyl group that may have a substituent. A good aryl group, an allyl group, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent, or a phenyl group bonded to a nitrogen atom is bonded as shown by the dotted line to form the following general formula: Represents a group forming any of the rings shown in [II] to [V], ▲There are mathematical formulas, chemical formulas, tables, etc.▼[II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼[III]▲Mathematical formulas, There are chemical formulas, tables, etc. ▼ [IV] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [V] n represents an integer of 1 or 2. However, A and R^1 may be integrated with each other to form a ring. ) A photoreceptor for electrophotography, comprising a photosensitive layer containing a hydrazone compound represented by: