JPH1063019A - Organic photoconductive material and electrophotographic photoreceptor using the same - Google Patents

Abstract

(57) Abstract: An object of the present invention is to provide an electrophotographic photoreceptor, a sensor material, and an EL element which exhibit high performance with high charge potential, high sensitivity, and stable performance even when used repeatedly without changing various characteristics. To provide an organic photoconductive material which can be used for an electrostatic recording element and the like. An organic photoconductive material represented by the following general formula (1), and a photosensitive layer containing one or more of these organic photoconductive materials on a conductive support. An electrophotographic photoreceptor, comprising: Embedded image In the general formula (1), R ₁ , R ₂ , R ₃ , R ₄ , and R ₅
Represents an aryl group or the like which may have a substituent, and X represents an arylene group or the like which may have a substituent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic photoconductive material and an electrophotographic photoreceptor using the same, and more particularly, to an electrophotographic photoreceptor containing a specific organic photoconductive material. It is.

[0002]

2. Description of the Related Art In recent years, the use of the electrophotographic method has spread not only in the field of copying machines but also in fields in which photographic technology has been conventionally used, such as printing plate materials, slide films, and microfilms. Application to a high-speed printer using a light source is also being studied. Recently, the use of a photoconductive material other than an electrophotographic photosensitive member, for example, an application to an electrostatic recording element, a sensor material, an EL element, and the like has begun to be studied. Accordingly, demands for photoconductive materials and electrophotographic photoreceptors using the same are becoming higher and wider.
Heretofore, inorganic photoconductive materials such as selenium, cadmium sulfide, zinc oxide, and silicon have been known as electrophotographic photosensitive members, and have been widely studied and put to practical use. While these inorganic materials have many advantages, they also have various disadvantages. For example, selenium has drawbacks in that the production conditions are difficult and it is easy to crystallize due to heat and mechanical shock, and cadmium sulfide and zinc oxide have poor moisture resistance and durability. It has been pointed out that silicon is insufficient in chargeability and difficult to manufacture. In addition, selenium and cadmium sulfide have toxicity problems.

On the other hand, organic photoconductive materials have good film-forming properties, excellent flexibility, are lightweight, have good transparency, and are sensitive to a wide wavelength range by an appropriate sensitization method. Due to its advantages such as easy design of the body, its practical use is gradually attracting attention.

Incidentally, the photoreceptor used in the electrophotographic technology is generally required to have the following basic properties. That is, (1) high chargeability against corona discharge in a dark place, (2) little leakage (dark decay) of the obtained charge in a dark place, and (3) charge charge by light irradiation. (4) The residual charge after light irradiation is small.

However, many studies have been made on photoconductive polymers such as polyvinyl carbazole as organic photoconductive substances to date, but these have not always had sufficient film-forming properties, flexibility and adhesiveness. Also, it is difficult to say that the above-mentioned basic properties of the photoreceptor are sufficiently provided.

On the other hand, as for the organic low-molecular-weight photoconductive compound, by selecting a binder or the like used for forming the photoreceptor, the photoreceptor having excellent mechanical strength such as film property, adhesiveness and flexibility can be obtained. Can be obtained, but it is difficult to find a compound suitable for maintaining high-sensitivity properties.

In order to improve such a point, an organic photoreceptor having a higher sensitivity characteristic has been developed in which the charge generation function and the charge transport function are shared by different substances. The feature of such a photoreceptor, which is called a function-separated type, is that a material suitable for each function can be selected from a wide range, and a photoreceptor having an arbitrary performance can be easily manufactured. Has been advanced.

Among them, various substances such as phthalocyanine pigments, squarium dyes, azo pigments and perylene pigments have been studied as substances in charge of the charge generation function. Among them, azo pigments can have various molecular structures. Also, since high charge generation efficiency can be expected, it has been widely studied, and its practical use has been advanced. However, in this azo pigment, the relationship between the molecular structure and the charge generation efficiency has not been clarified yet. The fact is that we are searching for the optimal structure through extensive synthesis research, but it fully satisfies the basic properties and high durability demands of the photoconductors listed above. Things have not yet been obtained.

[0009] On the other hand, the substances in charge of the charge transport function include a hole transport substance and an electron transport substance. A variety of materials such as hydrazone compounds and stilbene compounds have been studied as hole transport materials, and 2,4,7-trinitro-9-fluorenone and diphenoquinone derivatives have been studied as electron transport materials. The fact is that they are conducting extensive synthetic research to search for the optimal structure.
In fact, many improvements have been made so far, but none of the above-mentioned photoconductors sufficiently satisfy the requirements such as the basic properties and high durability required for the photoconductors.

As described above, various improvements have been made in the production of electrophotographic photoreceptors, but the requirements for the basic properties and high durability required for the above-mentioned photoreceptors have not been sufficiently satisfied. At present, there is no satisfactory product yet.

[0011]

SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photoreceptor, a sensor material, and an EL element which exhibit a high charge potential, high sensitivity, stable performance even when used repeatedly without changing various characteristics. Another object of the present invention is to provide an organic photoconductive material that can be used for an electrostatic recording element and the like.

[0012]

Means for Solving the Problems The present inventors have studied photoconductive materials to achieve the above object, and as a result, have found that an organic photoconductive material having a specific structure is effective. Invented the invention. The organic photoconductive material having a specific structure as described above is a compound represented by the following general formula (1).

[0013]

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In the general formula (1), R ₁ , R ₂ , R ₃ ,
And R ₄ each represent an alkyl group optionally having a substituent, an aralkyl group, an aryl group, a heterocyclic group, or a hydrogen atom; R ₅ represents an alkyl group optionally having a substituent; X represents an aralkyl group, an aryl group, or a heterocyclic group; X represents an arylene group which may have a substituent;
And a divalent fused polycyclic group, a divalent heterocyclic group, or a group represented by the following general formula (2) or (3). In the general formulas (2) and (3), R ₆ is
A C1-C4 alkyl group, a C1-C4 alkoxy group,
Or a halogen atom, Y represents an oxygen atom, a sulfur atom, a selenium atom, or a carbonyl group;
Indicates an integer of 4.

[0015]

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Here, specific examples of R ₁ , R ₂ , R ₃ and R ₄ include a methyl group, an ethyl group, a propyl group, a butyl group,
Octyl group, isopropyl group, 2-methoxyethyl group,
Alkyl groups such as benzyl group, 4-methoxybenzyl group, aralkyl group such as β-phenylethyl group, phenyl group, p-tolyl group, 3-chlorophenyl group, 1-pyrenyl group, 4methoxy-1-naphthyl group, Aryl groups such as
Examples include a heterocyclic group such as a 2-pyridyl group, a 5-indolyl group, and a 2-tetrahydropyranyl group, or a hydrogen atom. Specific examples of R ₅ include a methyl group, an ethyl group, a propyl group, a butyl group, and octyl. Group, isopropyl group, 2-
Alkyl group such as methoxyethyl group, benzyl group, 4-
Methoxybenzyl group, aralkyl group such as β-phenylethyl group, phenyl group, p-tolyl group, 3-chlorophenyl group, 1-pyrenyl group, 4methoxy-1-naphthyl group,
And heterocyclic groups such as a 2-pyridyl group, a 5-indolyl group and a 2-tetrahydropyranyl group.

Specific examples of X include arylene such as p-phenylene, m-phenylene, 2-methyl-1,4-phenylene, and 2,5-dimethoxy-1,4-phenylene. Group, 1,4-naphthylene group, 4-chloro-1,3-naphthylene group, 1,8-pyrenylene group,
Or a divalent heterocyclic group such as a 2,5-furandiyl group, a 2,5-pyridinediyl group, a 2,4-quinolinediyl group, a 3,6-carbazolediyl group, or the like. , 4,4'-biphenylene group, 3-methyl-4,4
'-Biphenylene group, 3,3'-dichloro-4,4'-
Divalent biphenyl groups such as biphenylene group and 4-methoxy-2,4'-biphenylene group, or diphenyl ether, diphenyl sulfide, diphenyl selenide,
Or a divalent group obtained by removing two hydrogen atoms from benzophenone, or a lower alkyl group such as a methyl group, an ethyl group, or a butyl group, a methoxy group, a lower alkoxy group such as a butoxy group, or Examples thereof include divalent groups having a halogen atom such as a chloro atom or a bromo atom as a substituent.

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Specific examples of the organic photoconductive material represented by the general formula (1) according to the present invention include those having the following structural formulas, but are not limited thereto. Absent.

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The electrophotographic photoreceptor of the present invention comprises, on a conductive support, an organic photoconductive material represented by the general formula (1), preferably one or two kinds of the organic photoconductive material and the charge generating material. It can be obtained by providing a photosensitive layer containing the above. The charge generating substance includes an inorganic charge generating substance and an organic charge generating substance. Examples of the former include selenium, selenium-tellurium alloy, selenium-arsenic alloy, cadmium sulfide, zinc oxide, amorphous silicon and the like.
Examples of organic charge generating substances include, for example, triphenylmethane dyes such as methyl violet, brilliant green, and crystal violet; thiazine dyes such as methylene blue; quinone dyes such as quinizarin; cyanine dyes; acridine dyes; pyrylium dyes; And squarium dyes, perinone pigments, anthraquinone pigments, phthalocyanine pigments containing and containing no metal, and perylene pigments, and azo pigments are also used.

As the azo pigment, for example, JP-A-47-3
7543, JP-A-53-95033, JP-A-53-95033
132347, JP-A-53-133445, JP-A-54-12742, JP-A-54-20736, JP-A-54-20737, JP-A-54-21728, JP-A-54-22834 JP-A-55-69148,
JP-A-55-69654 and JP-A-55-79449.
JP-A-55-117151, JP-A-56-462
No. 37, JP-A-56-116039, JP-A-56-1
No. 16040, JP-A-56-119134, JP-A-5-119134
6-143437, JP-A-57-63537, JP-A-57-63538, JP-A-57-63541, JP-A-57-63542, JP-A-57-63549,
JP-A-57-66438, JP-A-57-74746
JP-A-57-78542 and JP-A-57-7854.
3, JP-A-57-90056, JP-A-57-90056
No. 57, JP-A-57-90632, JP-A-57-11
6345, JP-A-57-202349, JP-A-58
-4151, JP-A-58-90644, JP-A-58-9064
JP-A-144358, JP-A-58-177555, JP-A-59-31962, JP-A-59-33253, JP-A-59-71059, JP-A-59-72448,
JP-A-59-78356, JP-A-59-136351
JP-A-59-201060, JP-A-60-156
No. 42, JP-A-60-140351, JP-A-60-1
No. 79746, JP-A-61-11754, JP-A-61-11654
-90164, JP-A-61-90165, JP-A-6
1-90166, JP-A-61-112154, JP-A-61-281245, JP-A-61-51063,
JP-A-62-267363, JP-A-63-68844
JP-A-63-89866, JP-A-63-1393
No. 55, JP-A-63-142063, JP-A-63-1
No. 83450, JP-A-63-282743, JP-A-6-282743
JP-A-4-21455, JP-A-64-78259, JP-A-1-200267, JP-A-1-202775, JP-A-1-319754, JP-A-2-72372, JP-A-2-254467, JP-A-2-254467 JP-A-3-27863, JP-A-4-96068, JP-A-4-96069, JP-A-4-147265, JP-A-5-142841, JP-A-5-303226, JP-A-6-324504,
Compounds described in JP-A-7-168379 and the like can be mentioned.

The structure of the coupler component used in these azo pigments varies widely. For example, Japanese Patent Application Laid-Open
No. 17735, JP-A-54-79632 and JP-A-57
-176055, JP-A-59-197043, JP-A-60-130746, JP-A-60-153050
JP-A-60-103048, JP-A-60-189
759, JP-A-63-131146, JP-A-63-131146
155052, JP-A-2-110569, JP-A-4
-149448, JP-A-6-27705, JP-A-6-27705
And the compounds described in JP-A-348047 and the like.

Specific examples of the azo pigment include the compounds shown in the following table, but are not limited thereto. Further, these compounds can be used in combination with other charge generating substances.

[0098]

[Table 1]

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[Table 45]

Various types of photosensitive members are known, and any of them can be used. For example, there is one in which a photosensitive layer comprising a charge generating substance, a charge transporting substance, and a film-forming binder resin is provided on a conductive support. Further, a laminated photoreceptor in which a charge generation layer composed of a charge generation substance and a binder resin and a charge transport layer composed of a charge transport substance and a binder resin are provided on a conductive support is also known. . Either of the charge generation layer and the charge transport layer may be an upper layer. In addition, if necessary, an undercoat layer is provided between the conductive support and the photosensitive layer, an overcoat layer is provided on the surface of the photosensitive member, and in the case of a laminated photosensitive member, an intermediate layer is provided between the charge generation layer and the charge transport layer. Can also be provided. As a support for producing a photoreceptor using the compound of the present invention, a metal drum,
A metal plate, a paper subjected to conductive processing, a plastic film sheet, a drum-shaped or belt-shaped support, and the like are used.

As the film-forming binder resin used for forming the photosensitive layer on the support, there are various resins depending on the field of use. For example, for photoreceptors for copying, polystyrene resin, polyvinyl acetal resin, polysulfone resin, polycarbonate resin, vinyl acetate
Crotonic acid copolymer resin, polyester resin, polyphenylene oxide resin, polyarylate resin, alkyd resin, acrylic resin, methacrylic resin, phenoxy resin and the like. Among these, polystyrene resin, polyvinyl acetal resin, polycarbonate resin, polyester resin, polyarylate resin, and the like are excellent in potential characteristics as a photoconductor. Also, these resins are
One type or a mixture of two or more types may be used alone or as a copolymer. The amount of the binder resin added to the photoconductive compound is preferably 20 to 1000% by weight, more preferably 50 to 500% by weight.

In the case of a laminate type photoreceptor, these resins contained in the charge generation layer are 10 to 50 with respect to the charge generation substance.
0% by weight is preferable, and 50 to 150% by weight is more preferable. If the ratio of the resin is too high, the charge generation efficiency is lowered, and if the ratio of the resin is too low, there is a problem in film formability. Further, the content of these resins contained in the charge transport layer is preferably from 20 to 1,000% by weight, more preferably from 50 to 500% by weight, based on the charge transport material. If the ratio of the resin is too high, the sensitivity is lowered, and if the ratio of the resin is too low, the repetition characteristics may be deteriorated or the coating film may be damaged.

Among these resins, tension, bending,
Some have weak mechanical strength such as compression. To improve this property, substances which impart plasticity can be added. Specifically, phthalic acid esters (eg, DOP, DOP
BP, etc.), phosphate esters (eg, TCP, TOP
Etc.), sebacic esters, adipic esters, nitrile rubbers, chlorinated hydrocarbons and the like. If these substances are added unnecessarily, they adversely affect the electrophotographic properties. Therefore, the ratio is preferably 20% or less based on the binder resin.

In addition, a leveling agent or the like as an additive to the photoreceptor for improving coatability, such as an antioxidant or an anti-curl agent, can be added as needed.

The compound represented by the formula (1) can be used in combination with another charge transporting substance. The charge transport materials include a hole transport material and an electron transport material. Examples of the former include oxadiazoles disclosed in JP-B-34-5466 and JP-B-45-555.
JP, JP-B-52-4188, etc., pyrazolines, etc .;
Examples thereof include hydrazones disclosed in JP-B-55-42380, oxadiazoles disclosed in JP-A-56-123544 and the like. On the other hand, examples of electron transporting substances include chloranil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,4
7-trinitro-9-fluorenone, 2,4,5,7-
Tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 1,3,7-trinitrodibenzothiophene, 1,3,7-trinitrodibenzothiophene- 5,
5-dioxide and the like. These charge transport materials can be used alone or in combination of two or more.

A certain electron-withdrawing compound can be added as a sensitizer for forming a charge transfer complex with the organic conductive material of the present invention and further increasing the sensitizing effect. Examples of the electron-withdrawing compound include 2,3-dichloro-1,4-naphthoquinone, 1-nitroanthraquinone,
Quinones such as 1-chloro-5-nitroanthraquinone, 2-chloroanthraquinone and phenanthrenequinone;
Aldehydes such as -nitrobenzaldehyde, ketones such as 9-benzoylanthracene, indandione, 3,5-dinitrobenzophenone, 3,3 ', 5,5'-tetranitrobenzophenone, phthalic anhydride and 4-chloronaphthalic anhydride Acid anhydrides, terephthalalmalononitrile, 9-anthrylmethylidenemalononitrile,
Cyano compounds such as 4-nitrobenzalmalonenitrile, 4- (p-nitrobenzoyloxy) benzalmalonenitrile, 3-benzalphthalide, 3- (α-cyano-p
-Nitrobenzal) phthalide, 3- (α-cyano-p-
And phthalides such as nitrobenzal) -4,5,6,7-tetrachlorophthalide.

The organic photoconductive material of the present invention is dissolved or dispersed in an appropriate solvent together with the above-mentioned various additives depending on the form of the photoreceptor, and the coating solution is coated on the above-mentioned conductive support. And dried to produce a photoreceptor.

Examples of the coating solvent include halogenated hydrocarbons such as chloroform, dichloroethane, dichloromethane, trichloroethane, trichloroethylene, chlorobenzene and dichlorobenzene, aromatic hydrocarbons such as benzene, toluene and xylene, dioxane, tetrahydrofuran, methyl cellosolve, ethyl cellosolve, and the like. Ether solvents such as ethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, methyl isopropyl ketone and cyclohexanone, ester solvents such as ethyl acetate, methyl formate, methyl cellosolve acetate, N, N-dimethylformamide, acetonitrile; Non-protonic polar solvents such as N-methylpyrrolidone and dimethyl sulfoxide and alcohol solvents can be exemplified. These solvents can be used alone or as a mixed solvent of two or more kinds.

[0152]

EXAMPLES Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

SYNTHESIS EXAMPLE 1 Synthesis of Exemplified Compound 7 4- [N- (2,2-diphenylphenyl) -N-phenylamino] benzarthuman1.22
g and 0.61 g of p-xylylene bis (diethylphosphonate) are dissolved in 50 ml of N, N-dimethylformamide, and the mixture is stirred under room temperature.
Add 0.55 g of t-photoxite and continue stirring at room temperature for 24 hours. Thereafter, the reaction solution is poured into 300 ml of ice water, and after stirring for a while, the precipitated crystals are collected by filtration, washed with water on a glass filter, and further dispersed and washed with methanol. The obtained crystals were recrystallized from 45 ml of benzene to obtain 0.34 g of Compound 7. Yield: 26%, melting point: 249.0-254.3 ° C

Example 1 1 part by weight of an azo pigment (A-2) and 1 part by weight of a polyester resin (Vylon 200 manufactured by Toyobo) were mixed with 100 parts by weight of tetrahydrofuran, and dispersed together with glass beads by a paint conditioner for 2 hours. The dispersion thus obtained was applied on an aluminum-evaporated polyester using an applicator and dried to form a charge generation layer having a thickness of about 0.2 μm. Next, Exemplified Compound 7 of the present invention was mixed with a polyarylate resin (U-Polymer manufactured by Unitika) at a weight ratio of 1: 1 to prepare a 10% solution using dichloroethane as a solvent. Was applied with an applicator to form a charge transport layer having a thickness of about 20 μm.

The electrophotographic characteristics of the laminated photoreceptor thus manufactured were evaluated using an electrostatic recording tester (SP-428, manufactured by Kawaguchi Electric Co., Ltd.). Measurement conditions: applied voltage -6 kV, static No. 3 (turntable rotation speed mode: 10 m / min)
). As a result, the charging potential (Vo) was -740 V, and the half-life exposure amount (E1 / 2) was 1.1 lux / sec, which was a high sensitivity value.

Further, the same apparatus was used to evaluate characteristics for repeated use in which charge-discharge (discharge light: white light, 400 lux × 1 second irradiation) was performed in one cycle. 5000
The change in the charged potential due to the repetition of
The charging potential (Vo) at the 5000th time was −740 V, as compared with the charging potential (Vo) at the −740 V, and the characteristics were stable without a decrease in potential due to repetition. Also, the 5000th half-exposure dose (E1 / 2) was 1.1 lux / sec, which was the same as the first half-exposure dose (E1 / 2) of 1.1 lux / sec. .

Examples 2 to 9 The same procedures as in Example 1 were carried out except that the azo pigment (A-2) of Example 1 and the compound of the present invention were used instead of the azo pigment (A-2) and Exemplified Compound 7, respectively, as shown in Table 46. Then, a photoreceptor was manufactured and its characteristics were evaluated. The results are shown in Table 46.

[0158]

[Table 46]

Examples 10 to 18 The same procedures as in Example 1 were carried out except that the azo pigment of Example 1 was replaced with an X-type metal-free phthalocyanine, and the compounds of the present invention shown in Table 47 were used instead of Exemplified Compound 7. Then, a photoreceptor was manufactured and its characteristics were evaluated. The results are shown in Table 47.

[0160]

[Table 47]

Example 19 1 part by weight of an azo pigment (A-2) and tetrahydrofuran 40
Parts by weight were dispersed for 4 hours together with glass beads in a paint conditioner. In the dispersion thus obtained,
2.5 parts by weight of the compound of the present invention (Exemplified Compound 7), 10 parts by weight of a polycarbonate resin (PCZ-200; manufactured by Mitsubishi Gas Chemical Co., Ltd.) and 60 parts by weight of tetrahydrofuran are added, and the mixture is further dispersed for 30 minutes by a paint conditioner. After that, the resultant was coated on an aluminum vapor-deposited polyester with an applicator to form a photoreceptor having a thickness of about 15 μm. The electrophotographic characteristics of this photoreceptor were evaluated in the same manner as in Example 1. However, only the applied voltage was changed to +5 kV. As a result, the first charging potential (Vo) +480 V,
Half-exposure (E1 / 2) 1.1 lux / sec. Charge potential (Vo) after 5,000 repetitions + 470 V, half-exposure (E1 / 2) 1.1 lux / sec, high sensitivity and little change And excellent properties.

Examples 20 to 27 The same procedures as in Example 19 were carried out except that the azo pigment (A-2) of Example 19 and the compound of the present invention were replaced by the azo pigments shown in Table 48 and the compounds of the present invention, respectively. Then, a photoreceptor was manufactured and its characteristics were evaluated. The results are shown in Table 48.

[0163]

[Table 48]

Comparative Example 1 A photoconductor was prepared in the same manner as in Example 1 except that Compound 81 was used instead of Compound 7 as the charge transporting material, and the characteristics were evaluated. As a result, the first charging potential was (Vo) -680 V, and the half-exposure amount (E1 / 2) was 2.2.
Looks second, low sensitivity, 5000th charge potential (Vo) is -440V, half-exposure (E1 / 2) 2.1
Looks second, and a significant decrease in potential due to repetition was observed.

Comparative Example 2 A photoconductor was prepared and the characteristics were evaluated in the same manner as in Example 10, except that Comparative Compound 82 was used instead of Exemplary Compound 9 as the charge transport material. As a result, the first charging potential (Vo) was -700 V, and the half-exposure amount (E1 / 2) was 1.
The results were relatively good at 3 looks / sec, but 500
The 0th charging potential (Vo) was -310 V, the half-life exposure amount (E1 / 2) was 1.1 lux / sec, and a drastic decrease in potential due to repetition was observed.

Comparative Example 3 A photoconductor was prepared and the characteristics were evaluated in the same manner as in Example 19, except that Comparative Compound 83 was used instead of Exemplary Compound 7 as the charge transport material. As a result, the charging potential (V
o) was 370 V, and the half-life exposure amount (E1 / 2) was 7.7 lux / sec, which was insufficient sensitivity.

[0167]

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[0168]

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[0170]

As is apparent from the above, an electrophotographic photosensitive member having high sensitivity and high durability can be provided by using the organic photoconductive material of the present invention.

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Claims (3)

[Claims] 1. An organic photoconductive material represented by the following general formula (1). Embedded image (In the general formula (1), R ₁ , R ₂ , R ₃ , and R ₄ are
Each represents an optionally substituted alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a hydrogen atom, and R ₅ represents an optionally substituted alkyl group, an aralkyl group, or an aryl group. Or a heterocyclic group;
Represents an arylene group which may have a substituent, a divalent fused polycyclic group, a divalent heterocyclic group, or a group represented by the following formula (2) or (3). In the general formulas (2) and (3), R ₆ represents C1 to C4
Y represents an oxygen atom, a sulfur atom, a selenium atom, or a carbonyl group, and n represents an integer of 0 to 4. ) Embedded image 2. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer containing an organic photoconductive material represented by the above general formula (1). 3. The photosensitive layer contains a charge generating substance and a charge transporting substance, wherein the charge transporting substance is an organic photoconductive material represented by the general formula (1). The electrophotographic photosensitive member according to the above.