JPS63172161A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To improve the flexibility, the photosensitivity, the electrification and the residual potential of the titled body by incorporating at least one kind of hydrazone compds to a photosensitive layer. CONSTITUTION:The titled body comprises a conductive supporting body and the photosensitive layer laminated on the conductive supporting body, and the photosensitive layer contains one kinds of the hydrazone compd. shown by the formula. In formula I, R1 and R2 are each independently 1-3C alkyl, aryl or benzyl group, R3 and R4 are each alkyl, aralkyl or aryl group. In formulas II and III, R1 and R4 are each hydrogen or halogen atom, 1-3C alkyl, 1-3C alkoxy, hydroxyl, nitro, amino or a substd. amino group, R2 is hydrogen atom or 1-3C alkyl, R3 is hydrogen atom, alkyl, aralkyl or aryl group. Thus, the titled body has the stability to light, heat and ozone, and the stable electrification, photosensitivity and residual potential, even in case of using for long period.

Description

[Detailed Description of the Invention] [Object of the Invention] (Industrial Application Field) The present invention relates to an electrophotographic photoreceptor that is effective for use in the Carlson method, and more specifically, it has excellent photosensitivity, charging characteristics, and residual potential. The present invention relates to an electrophotographic photoreceptor with good stability of properties and excellent durability.

(Prior Art) The photoconductive process of electrophotographic photoreceptors consists of a photocharge generation process and a charge transport process. Conventionally, for electrophotographic photoreceptors, two methods are known: one in which the above two processes are carried out using one substance, and the other in which the two processes are carried out using separate substances.

Of the two methods described above, the method in which each process is performed using separate materials expands the range of materials to be used for the photoreceptor, and the electrophotographic properties such as sensitivity and 3' potential of the resulting photoreceptor are improved. Greeting 1. In addition, it has the advantage that a photoreceptor with excellent coating properties can be produced when manufacturing a photoreceptor.

For example, the following types of laminated photoreceptors are known.

However, such conventionally known photoreceptors have several problems. For example, in a photoreceptor using amorphous selenium, the layer used for the charge transport layer (1) is hard because vinyl carbazole lacks flexibility.
It has the disadvantage that it is brittle and prone to cracking, peeling, and other phenomena, and has poor durability as a photoreceptor. Therefore, in order to increase the flexibility of polyvinylcarbazole, a method of using it together with a plasticizer has been proposed. However, this method has a major drawback in that residual charges in the charge transport layer increase, resulting in deterioration of electrophotographic properties such as fogging of images.

Furthermore, photoreceptors using low-molecular cloudy organic compounds as charge transport materials, such as 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, have relatively excellent electrophotography. Although some of them have properties, they generally do not have the ability to form a film, so they are used in combination with a polymeric binder that has the ability to form a film to form a charge transport layer. However, even if these low molecular weight organic compounds have excellent electrophotographic properties, they generally have poor compatibility with polymeric binders.
When a film is formed as a charge transport layer, it tends to crystallize and has poor thermal stability. In addition, in terms of electrophotographic characteristics, none of the conventionally known photoreceptors mentioned above has sufficient sensitivity, and moreover, some of them cause fluctuations in surface potential, particularly a decrease in charge retention ability, when subjected to repeated exposure charging. many.

Another drawback is that the sensitivity and image contrast change with changes in the environment, especially changes in humidity.

(Problems to be Solved by the Invention) As mentioned above, conventional electrophotographic photoreceptors have problems with flexibility and compatibility with polymeric binders, and also have problems with photosensitivity and property deterioration due to repeated use. Also, there are problems with deterioration of characteristics due to the environment.

The present invention eliminates the drawbacks of the conventional electrophotographic photoreceptor, and has excellent flexibility, excellent photosensitivity, charging characteristics, and residual potential characteristics, and small deterioration of various characteristics due to repeated use and changes in various environments. The purpose is to provide electrophotographic photoreceptors.

[Structure of the invention]

(Means and effects for solving the problems) In order to achieve the above object, the present inventors studied various low-molecular H organic compounds and arrived at the present invention.

That is, it is an electrophotographic photoreceptor comprising an electrically conductive support and a photosensitive layer laminated on the electrically conductive support, where the photosensitive layer contains at least one type of hydrazone compound.

In particular, the hydrazone compound in the photosensitive layer has the following general formula [
I] a In the formula: R1 and R2 are each independently an alkyl group having 1 to 3 carbon atoms, an aryl group which may have a substituent, or a benzyl group R3 and R4 are each independently a substituent, Good alkyl group, aralkyl group, aryl group R5 represents an optionally substituted aryl group or aralkyl group.

It is characterized by containing at least one type of hydrazone compound shown in the following.

Furthermore, the hydrazone compound of the photosensitive layer has the following general formula and round shape 3, where: R1, R4 - hydrogen atom, halogen atom, carbon number 1
-3 alkyl group, C1-3 alkoxy group, hydroxyl group, nitro group, amino group, or substituted amino group. Further, n is an integer of 1 to 5, m is an integer of 1 to 4, and n.

If m is 2 or more, R1 or R4 is the same but different It's okay.

R2-represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

R3-represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group that may be replaced.

This is an electrophotographic photoreceptor containing at least one of the compounds shown below.

In addition, the present invention provides at least one shydrazone compound represented by the following general formula nvl! ! An electrophotographic photoreceptor characterized by containing:

In the formula: R1, R2, R3, and R4 represent an optionally substituted alkyl group, aralkyl group, aryl group, or heterocyclic group.

Xl and X2 represent a heterocyclic group which may be substituted with e1.

2 represents a divalent organic residue.

The present invention includes, for example, a functionally separated single-core photoreceptor containing at least one layer of a charge generating substance and a charge transporting substance on a conductive substrate, and at least two layers of a charge generating layer and a charge transporting layer on a conductive substrate. It can be applied to any type of electrophotographic photoreceptor, such as a functionally separated stacked stone photoreceptor in which a charge transport port and a charge generation layer are sequentially laminated or at least two layers of a charge transport port and a charge generation layer are sequentially laminated.

Hereinafter, the present invention will be roughly explained in detail by taking an example of a functional valve m-type product β photoreceptor.

The conductive support used in the present invention is not particularly limited, and may be any support that is normally used as a conductive support for electrophotographic photoreceptors. Such supports include, for example, metallic materials such as brass, aluminum, gold, and silver; metal surfaces coated with a thin film of plastic; metal-coated paper, metal-coated plastic sheets, or iodine. Conductors such as aluminum oxide, copper iodide, chromium oxide or tin oxide! Examples include old coated glass. These are used as thin cylindrical sheets with appropriate thickness, hardness, and flexibility, and either the support itself is conductive or its surface is conductive, and has sufficient strength for handling. It is preferable that the

A charge generation layer or a charge transport layer, which will be described later, is formed on such a conductive support.

The substance H constituting the charge generation layer may be any charge generation substance as long as it absorbs light and generates charges (carriers) with high efficiency.

Examples of such charge generating substances include selenium and J
: Selenium alloy; CdS, CdSe, Cd5Se, Zn
Inorganic light guides such as O and ZnS: phthalocyanine pigments such as metal phthalocyanines and non-metal phthalocyanines;
Azo dyes such as monoazo dyes and disazo dyes; penylene dyes such as benylene anhydride and benylene imide; indigoid dyes; quinacridone pigments; polycyclic quinones such as anthraquinones and pyrenequinones; cyanine dyes: xanthene dyes; Examples include charge transfer complexes comprising an electron donating substance such as poly-N-vinylcarbazole and an electron accepting substance such as trinitrofluorenone; and eutectic complexes comprising a pyrylium salt dye and a polycarbonate resin.

Methods for forming the charge generation layer vary depending on the type of charge generation substance used, but include various coating methods such as spin coating, pulling method, roller coating method, doctor blade coating method, vacuum evaporation method, A sputtering method and a plasma CVD method using glow discharge, for example, can be appropriately selected and applied.

The thickness of the charge generation openings to be formed at this time is appropriately determined depending on the charging characteristics required for the electrophotographic photoreceptor.
Usually, it is preferably about 0.1 to 20.

Note that when forming the charge generation layer on the conductive support,
If necessary, a contact I! is provided between the conductive support and the charge generating bottom. tFf! J may also be formed. As the material for forming the adhesive opening, a conventionally commonly used material such as Chikyoin can be used, and the thickness thereof is 0.1 to 10 JJ! It
, preferably about 0.5 to 2.

The charge transport layer contains at least one hydrazone compound represented by each of the above general formulas.

In these compounds, the aryl group includes, for example, di-substituted amino groups (e.g., dimethylamino group, diethylamino group, dibutylamino group, methylethylamino group,
dialkylamino groups such as methylbutylamino group and siamylamino group; dialkylamino groups such as dibenzylamino group and diarylamino group; diarylamino groups such as diphenylamino group, ditolylamino group and dixylylamino group); alkoxy groups (e.g. methoxy group, ethoxy group, propoxy group, butoxy group) and aryloxy group (
For example, phenoxy group, naphthoxy group), alkyl group, nitro group, cyano group, yahydroxy group, acetyl group, phenyl group which may be substituted with halogen, naphthyl group, anthracene group, phenanthrene group, tetralin group, azulene group , biphenylene group, acenaphthylene group, acenaphthene group, fluorene group, fluoranthene group,
Examples include triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, benzopyrene group, rubycene group, coronene group, and obalene group.

In the above compound, examples of the aralkyl group include:
Disubstituted amino groups (e.g. dimethylamino group, diethylamino group, dibutylamino group, methylethylamino group,
Diarylamino groups such as methylbutylamino group and siamylamino group; , propoxy group, butoxy group), aryl group, oxy group (e.g., phenoxy group, naphthoxy group), alkyl group, nitro group, cyano group, hydroxy group, acetyl group, benzyl group that may be substituted with halogen, phenethyl group, Examples include phenylpropyl group, phenylbutyl group, naphthylmethyl group, naphthylethyl group, and the like.

In the above compound, the alkyl group includes, for example, a di-purchased amino group (e.g., a dialkylamino group such as a dimethylamino group, a diethylamino group, a dibutylamino group, a methylethylamino group, a methylbutylamino group, a cyamylamino group; a dibenzylamino group; group, dialkylamino groups such as diphenethylamino group; diarylamino groups such as diphenylamino group, ditolylamino group, dixylylamino group) and alkoxy groups (e.g. methoxy group, ethoxy group,
propoxy group, butoxy group), aryloxy group (e.g. phenoxy group, naphthoxy group), nitro group, cyano group, hydroxy group, acetyl group, methyl group, ethyl group, propyl group, isopropyl group, which may be substituted with a halogen, etc. group, butyl group, pentyl group, hexyl J1%'
can be mentioned.

Pyrrole ring group, indole ring group, indoline ring group, isoindole ml, carbazole ring group, 7ran ring group, benzofuran ring group, diophene ring group, pyrazole ring group, pyrazoline ring group, benzopyrazole ring group, imidazole ring group, Imidacillin ring group, benzimidazole r! ! i group,
Oxazole ring group, benzoxazole ring group, naphthoxazole ring group, oxazoline ring group, thiazole 11,
thiazoline ring group, benzothiazoline ring group, triazole ring group, benzotriazole ring group, oxadiazole ring group, thiadiazole ring group, benzoxadiazole ring group,
benzothiadiazole ring group, tetrazole ring group, pyridine ring group, quinoline ring group, acridine ring group, phenanthridine ring group, benzoquinoline ring group, naphthoquinoline ring group,
Pyran ring group, benzopyran ring group, thiapyran I! :W,
Pyridazine W%, pyrimidine ring group, pyrazine, oxazine ring group, penzoxazine ring group, thiazine Wi group, benzothiazine ring group, phenothiazine ring group, dioxane ring group, triazine ring group, oxadiazine ring group, thiadiazine ring group, tetrazine ring group, benzofuran ring group, thiazole ring group, benzothiazole ring group, naphthothiazole ring group,
Examples include selenazole TM group, benzoselenazole ring group, naphthoselenazole ring group, and the like.

Divalent organic residues in this compound include optionally substituted alkylene groups such as methylene group, ethylene group, propylene group, butylene group, optionally substituted phenylene group, naphthylene group, biphenylene group, etc. An arylene group, a heterocyclic group such as an optionally substituted carbazolephenothiazine, etc. and its derivatives,
Others-@-o-@-. -os-@-. -@-NH@
−.

−0−υσX, etc. can be mentioned.

In addition, as substituents for the Ia group constituting the above-mentioned hetero ffl group, aryl group, aralkyl group, alkyl group, etc.,
For example, alkyl groups such as methyl, ethyl, and propyl; alkylene groups such as methylene, ethylene, and propylene; alkoxy groups of divalent organic residues such as methoxy and ethoxy; aryloxy such as phenoxy; Groups: Halogen atoms such as chlorine and bromine Dialkylamino groups such as dimethylamino, diethylamino and edilptylamino groups Diarylamino groups such as diphenylamino groups; Alkylarylamino groups such as ethylphenylamino groups; Methylthio group , Argylthio group such as ethylthio group: Nitro group, Nidiano group; Amino group: Hydroxyl group; Ester group such as methyl ester group, edyl ester group, phenyl ester group: Amide group such as phenylamide group, dimethoxyphenylamide group, diamino group dialkylamino groups such as dibenzylamino groups, diphenethylamino groups: diarylamino groups such as diphenylamino group, ditolylamino group, and dixylylamino group), alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group), aryloxy groups (e.g., phenoxy group, naphthoxy group), and alkyl groups. phenyl group, naphthyl group, anthracene group, phenanthrene group, tetralin group, azulene group, biphenylene group, acenaphthylene group, acenaphthene group, fluorene group that may be substituted with a group, a nitro group, a cyano group, a hydroxy group, an acetyl group, or a halogen. , fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, bicene group, perylene group, benzopyrene group, rubicene group, coronene group, obalene group; disubstituted amino groups (e.g. dimethylamino group, diethylamino group) group, dialkylamino groups such as dibutylamino group, methylethylamino group, methylethylamino group, cyamylamino group; dialkylamino groups such as dibenzylamino group, diarylamino group; diphenylamino group, ditolylamino group, diarylamino group, etc. Diarylamino group), alkoxy group (e.g. methoxy group, ethoxy group, propoxy group, butoxy group), aryloxy group (e.g. phenoxy group, naphthoxy group), alkyl group, cyano group, hydroxy group, etc. Benzyl group, phenethyl group, phenylpropyl group, phenylbutyl group, naphdylmethyl group, naphthylethyl group that may be substituted with e1 by acetyl group or halogen! Examples include aralkyl groups such as 3 and the like.

Specific examples of the hydrazone compounds represented by the above formulas using structural formulas include those shown in Table 1 below.

Below, the amidine compounds represented by the above-mentioned formulas are specifically exemplified by the structural formulas as shown in Table 2 below.

Below is Table 2 in the margin.Specific examples of the hydrazone compounds represented by the above formulas using their structural formulas include those shown in Table 3 below.

Margin below When forming a charge transport layer containing these compounds as essential components, since none of these compounds have film-forming properties, it is prepared by dissolving a polymer compound as described below in an appropriate organic solvent. It is necessary to form a layer by using a resin solution as a binding component.

Examples of such polymer compounds include polycarbonate, polyester carbonate, polystyrene, polyvinyl chloride, acrylic resin, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyvinyl acetal,
Known bonding materials for electrophotographic photoreceptors include phenolic resins, styrene-acrylic copolymers, Boryaryl 1-1, and alkyd resins.

In forming the layer, a mixture of preferably 0.1 to 5 parts of the above-mentioned polymer compound is added to 1 part of the above-mentioned hydrazone or hydrazone compound. A solution prepared by dissolving or dispersing in an organic solvent such as aromatic chlorine, ether, ester, ketone, etc. is applied using a conventional coating method such as a spin coating method, a pulling method, a roller coating method, a dogta blade coating method, etc. It may be applied onto the charge generation layer or the conductive support by a method or the like, and then dried.

It should be noted that two or more of the above-mentioned dracin or shydrazone compounds may be used in combination, or may be used in combination with a known charge transporting substance within the range that does not impair the effects of the present invention.

As for the thickness of the charge transport layer, it is usually preferable that the total thickness of the charge generation layer and the charge transport layer is 100 or less. Total thickness is 100 JJ! This is because if it exceeds lt, the flexibility and photosensitivity of the formed film will decrease.

(Example) Examples of the present invention will be described below.

Examples 1 to 6 A polyethylene terephthalate film coated with aluminum is used as a conductive support, and the aluminum is MI! A charge generating material as shown in Table 4 was deposited on the exposed surface by a coating method to form a charge generating layer having the thickness shown in Table 4.

Roughly, the compounds shown in Table 4 are selected from among the hydrazone compounds numbered in Table 1 above, and the solution prepared by dissolving the hydrazone compound and the polymer compound is subjected to the pulling method. The charge transport layer was coated at 90 DEG C. for 24 hours to form a charge transport layer having a thickness not shown in Table 4.

Table 4 in the margin below shows the chargeability (initial value of the photoreceptor surface potential when charged) of the photoreceptor thus obtained and the photosensitivity (necessary for the initial value of the surface potential to attenuate to 1/2). Exposure ff1) was measured and the results are shown in Table 4.

Further, the dark decay rate (decay rate of photoconductor surface potential in the dark) and residual potential (where the surface potential decay rapidly slows down due to exposure) of the photoconductor were as shown in Table 4.

When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, almost no abnormality was observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.

Comparative Examples 1 and 2 Electrophotographic photoreceptors were produced in the same manner as in Examples except that a pyrazoline derivative was used as the charge transport material.

The charging ability, photosensitivity, dark decay rate, and residual potential of this photoreceptor were measured and shown in Table 4.

When this photoreceptor was charged and exposed io, ooo times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance characteristics were compared with those of the examples. and was inferior.

Examples 7 to 12 A polyethylene terephthalate film on which aluminum is vapor-deposited is used as a conductive support, and a charge-generating substance as shown in Table 5 is deposited on the surface on which aluminum is vapor-deposited by a vapor deposition method or a coating method. A charge generation layer having a thickness as shown in Table 5 was formed.

Roughly, select the compounds shown in Table 5 from among the hydrazone compounds numbered in Table 2, and dissolve this hydrazone compound and the polymer compound!
ill! ! ! The solution was applied by pulling up method and heated at 90℃ for 24 hours.
The mixture was dried for a period of time to form a charge transport layer having a thickness as shown in Table 5.

The chargeability (initial value of the photoreceptor surface potential when it is set to Wll) and photosensitivity (the exposure stage required for the initial value of the surface potential to attenuate to 172) of the photoreceptor thus obtained were measured. The results are shown in Table 5.

When this photoconductor was repeatedly charged and exposed 10,000 times under 8 conditions in which heat, ozone, etc. were generated, almost no abnormality was observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small and fatigue resistant. It turned out that it has excellent characteristics.

Comparative Examples 3 to 4 Electrophotographic photoreceptors were produced in the same manner as in the examples except that a pyrarizone derivative was used as the charge transport material.

The charging ability and photosensitivity of this photoreceptor were measured and shown in Table 5.

When this photoconductor was repeatedly charged and exposed io and ooo times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared to that of the example. It was inferior.

In the following margin Examples 13 to 18, 500 g of a 5% by weight solution of the polymer compound shown in Table 6 was added.
5 g of the charge generating substance shown in Table 6 was added and dispersed in a ball mill to prepare a paint. For this paint, select a compound shown in Table 6 from among the compounds marked with Bantan in Table 2, and add 5 mol of this compound to the charge generating substance.
After adding them in the same ratio, they were coated and dried to form a photosensitive layer. Examples 6 to 1 of the photoreceptors prepared in this way
Tram performance and photosensitivity were measured in the same manner as in 2. The results are shown in Table 6.

When this photoreceptor was charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, almost no abnormalities were observed, and fluctuations in streetcar performance, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.

Comparative Examples 5-6 Example 1 except that an existing compound was used as the charge transport material
Photoreceptors were prepared in the same manner as in Examples 3 to 18. The charging ability and photosensitivity of this photoreceptor were measured and shown in Table 6.

When this photoreceptor was repeatedly charged and exposed 10,000 times under an environment generating heat, ozone, etc., changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared to that of the example. It was inferior.

Margin Examples 19 to 24 Below, the compounds shown in Table 7 were selected from the compounds numbered in Table 2, and a solution in which Compound 59 and 5 g of the polymer compound shown in Table 7 were dissolved was prepared. It was coated on aluminum mylar and dried to form a charge transporting bottom.

On this charge transport report, the charge generating substances T! shown in Table 7! 1
．． A paint in which 1.5 g of the compound numbered No. 59 in Table 2 or a known charge transporting substance was dispersed together with the polymer compound solution shown in Table 7 was applied and dried to form a charge generation layer. The photoconductors produced in this way were used in Examples 7-
Charging ability and photosensitivity were measured in the same manner as in No. 12. The results are shown in Table 7.

When this photoreceptor was repeatedly charged and exposed io and ooo times in an environment where heat, ozone, etc. were generated, no abnormalities were observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.

Comparative Examples 7-8 Examples 13-1 using existing compounds as charge transport materials
A photoreceptor was prepared in the same manner as in Example 8. The charging ability and photosensitivity of this photoreceptor were measured and shown in Table 7.

When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared with the example. It was inferior.

Examples 25 to 30 with blank spaces below: Using a polyethylene terephthalate film on which aluminum is vapor-deposited as a conductive support, a charge-generating substance as shown in Table 8 is applied to the surface on which aluminum is vapor-deposited by vapor deposition or coating method. The layers were laminated to form a charge-generating layer having a film thickness as shown in Table 8.

Roughly, the compounds shown in Table 8 were selected from among the bishydrazone compounds numbered in Table 3,
A solution prepared by dissolving this bishydrazone compound and a polymer compound was applied by a pulling method and dried at 90'C for 24 hours to form a charge transport port having a thickness of IIjl as shown in Table 8.

In this way, the chargeability of the photoconductor (the initial value of the photoconductor surface potential when charged) and the photosensitivity (the exposure device necessary for the initial value of the surface potential to attenuate to 1/2) are determined. The results are shown in Table 8.

This photoreceptor is heated and ozone is generated! Under 1 fft? 1
) Electron and light exposure were repeated 10,000 times, and almost no abnormality was observed, and variations in charging ability, photosensitivity, residual potential, etc. An electrophotographic photoreceptor was prepared.

The charging ability, photosensitivity, and residual potential of this photoreceptor were measured.
Shown in the table.

When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared with the example. It was inferior.

In the following margin Examples 31 to 36, 5009 % solution of the polymer compound shown in Table 9,
A charge generating substance 5tj shown in Table 9 was added and dispersed in a ball mill to prepare a paint. For this paint, the compounds shown in Table 9 were selected from among the compounds numbered in Table 3, and 5 mo of this compound was added to the charge generating substance.
After adding the mixture at a ratio of 1 to 1, the mixture was coated and dried to form a photosensitive aperture. The photoconductors produced in this way were used in Examples 25-
Charging ability and photosensitivity were measured in the same manner as No. 30. The results are shown in Table 9.

When this photoreceptor was repeatedly charged and exposed to light in an environment where heat, ozone, etc. were generated, almost no abnormalities were observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.

Comparative Examples 11-12 Example 3 except that an existing compound was used as the charge transport material
Photoreceptors were prepared in the same manner as in Examples 1 to 36. The charging ability and photosensitivity of this photoreceptor were measured and shown in Table 9.

When this photoreceptor was repeatedly charged and exposed io and ooo times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared to that of the example. It was inferior.

Margin Examples 37 to 42 Below, a 10th compound not shown in the table was selected from the compounds numbered in Table 3, and 5g of this compound and 1st compound were selected.
A solution in which polymer compound 5q shown in Table 0 was dissolved was applied onto aluminum mylar and dried to form a charge transport circuit.

On this charge transport port, a charge generator 'R shown in Table 10 is placed.
A paint in which compounds numbered 1.59 and 1.59 in Table 3 or known charge transport substances 1.5!7 were dispersed together with a polymer compound solution shown in Table 10 was applied and dried to form a charge generation layer. . The chargeability and photosensitivity of the photoreceptors thus prepared were measured in the same manner as in Examples 25-30.

The results are shown in Table 10.

When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, almost no abnormality was observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.

Comparative Examples 13-14 Example 37 except that an existing compound was used as the charge transport material
A photoreceptor was prepared in the same manner as in 42. The charging ability and photosensitivity of this photoreceptor were measured and shown in Table 10.

When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared with the example. It was inferior.

Below is the margin [of invention? [J] As is clear from the results of the examples, the electrophotographic photoreceptor of the present invention has charging characteristics with a greatly distorted charging ability, and has a smooth photosensitivity characteristic with a small half-exposure level. It is. In some cases, the dark decay rate decreases. Furthermore, the electrophotographic photoreceptor of the present invention has stability against light, heat, and ozone, and maintains stable charging characteristics, photosensitivity characteristics, and residual potential characteristics even when used for a long time. It has excellent durability.

Agent Patent Attorney Nori Chika Tsubo Scary Same Bamboo Flower Kikuo

Claims (1)

[Claims] (1) An electrophotographic photosensitive material comprising an electrically conductive support and a photosensitive layer laminated on the electrically conductive support, wherein the photosensitive layer contains at least one of the following hydrazone compounds: body. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] In the formula: R_1 and R_2 each independently have a carbon number of 1 to 3
represents an alkyl group, an aryl group which may have a substituent, or a benzyl group. R_3 and R_4 each independently represent an alkyl group, an aralkyl group, or an aryl group that may have a substituent. R_5 represents an optionally substituted aryl group or aralkyl group. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [III] In the formula: R_1, R_4 = hydrogen atom, halogen atom, alkyl group with 1 to 3 carbon atoms, number of carbon atoms 1 to 3 alkoxy groups,
Represents a hydroxyl group, nitro group, amino group or substituted amino group. Further, n is an integer of 1 to 5, m is an integer of 1 to 4, and when n and m are 2 or more, R_1 or R_4 may be the same or different. R_2 = hydrogen atom, alkyl group having 1 to 3 carbon atoms R_3 = hydrogen atom, optionally substituted alkyl group, aralkyl group, aryl group ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [IV] In the formula: R_1, R_2 , R_3, R_4 are optionally substituted alkyl groups, aralkyl groups, aryl groups, heterocyclic groups X_1, X_2 are optionally substituted heterocyclic groups Z is a divalent organic residue