JPH1090925A - Organic photoconductive material and electrophotographic photoreceptor using the same - Google Patents

Abstract

[PROBLEMS] To provide an organic photoconductive material which can be used for an electrophotographic photosensitive member having high sensitivity and high durability, a sensor material, an EL element, an electrostatic recording element, and the like. A conductive support contains one or more enamine compounds represented by the following general formula (1) or (2) as an organic photoconductive material. Embedded image In the general formula (1) or (2), R ₁ , R ₂ ,
R ₆ and R ₇ each represent an alkyl group which may have a substituent, an aryl group, or a heterocyclic ring; R ₃ and R _{8 each} represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, Shows an alkoxy group. R ₄ and R ₅ represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group, or a heterocyclic group. However, one of R ₄ and R ₅ always has an aryl group or a heterocyclic ring. R ₉ and R ₁₀ represent an optionally substituted alkyl group, alkenyl group, aralkyl group, aryl group, or heterocyclic ring. m and n show the integer of 0-2. Z represents an atomic group necessary for forming a saturated hydrocarbon ring or a 5- to 8-membered heterocyclic ring with two carbons of the indoline ring.

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 electrophotography is not limited to the field of copying machines, but has spread to fields in which photographic technology was conventionally used, such as printing plates, 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 for applications other than the electrophotographic photoreceptor, for example, an electrostatic recording element, a sensor material, an EL element, and the like has been 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. Furthermore,
Selenium and cadmium sulfide also 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. Various kinds of substances such as hydrazone compounds and stilbene compounds have been studied as hole transport substances, and 2,4,7-trinitro-9-fluorenone and diphenoquinone derivatives have been studied as electron transport substances.
Practical application is also progressing, but the fact is that we are also pursuing a huge amount of 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) or (2).

[0013]

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In the general formula (1) or (2), R
₁ , R ₂ , R ₆ , and R ₇ each represent an alkyl group, an aryl group, or a heterocyclic ring which may have a substituent; R ₃ and R _{8 each} represent a hydrogen atom;
A halogen atom, an alkyl group which may have a substituent,
Shows an alkoxy group. R ₄ and R ₅ represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group, or a heterocyclic group. However, one of R ₄ and R ₅ always has an aryl group or a heterocyclic ring. R ₉ and R ₁₀ represent an optionally substituted alkyl group, alkenyl group, aralkyl group, aryl group, or heterocyclic ring. m and n show the integer of 0-2. Z represents an atomic group necessary for forming a saturated hydrocarbon ring or a 5- to 8-membered heterocyclic ring with two carbons of the indoline ring.

Specific examples of R ₁ , R ₂ , R ₆ and R ₇ include alkyl groups such as methyl group, ethyl group, n-propyl group and isopropyl group, aryl groups such as phenyl group and naphthyl group, or Examples include a heterocyclic ring such as a furyl group and a thienyl group. R ₁ , R ₂ , R ₆ ,
R ₇ may have a substituent. Specific examples of the substituent include a halogen atom such as a fluorine atom and a chlorine atom, an alkoxy group such as a methoxy group, an ethoxy group and an isopropyloxy group, and the above-described alkyl group. And the like.

Specific examples of R ₃ and R ₈ include a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, an n-propyl group and an isopropyl group, an alkoxy group such as a methoxy group and an ethoxy group, a fluorine atom, Examples include a halogen atom such as a chlorine atom. R ₃ and R ₈ may have a substituent, and specific examples of the substituent include the above-described alkyl group and the above-described halogen atom.

Specific examples of R ₄ and R ₅ include a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, an n-propyl group and an isopropyl group, an aryl group such as a phenyl group and a naphthyl group, a furyl group, Heterocycles such as a thienyl group can be exemplified. R ₄ and R ₅ may have a substituent, and specific examples thereof include a fluorine atom,
Examples include a halogen atom such as a chlorine atom, an alkoxy group such as an alkyl group, a methoxy group, and an ethoxy group described above, and an aryl group described above.

Specific examples of R ₉ and R ₁₀ include alkyl groups such as methyl group, ethyl group, n-propyl group and isopropyl group, alkenyl groups such as allyl group and methallyl group, benzyl group and 1-naphthyl group. Examples include an aralkyl group such as a methyl group, an aryl group such as a phenyl group and a naphthyl group, and a heterocycle such as a furyl group and a thienyl group. R ₉ and R ₁₀ may have a substituent. Specific examples of the substituent include a halogen atom such as a fluorine atom and a chlorine atom, an alkoxy group such as a methoxy group and an ethoxy group, and the above-mentioned alkyl group. And the like.

Specific examples of Z include those shown in the following specific examples.

[0020]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Specific examples of the organic photoconductive material represented by the general formula (1) or (2) of the present invention include:
Examples include those having the structures of C-01 to 84 shown below, but are not limited thereto.

[0021]

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[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[0033]

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[0034]

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The electrophotographic photoreceptor of the present invention can be obtained by containing one or more kinds of the organic photoconductive material represented by the general formula (1) or (2) and the charge generating substance, respectively. 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, methyl violet, brilliant green, triphenylmethane dyes such as crystal violet, thiazine dyes such as methylene blue, quinone dyes such as quinizarin, cyanine dyes, acridine dyes,
Examples include pyrylium dyes, thiapyrylium dyes, 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-53-132347, JP-A-53-13344
No. 5, JP-A-54-12742, JP-A-54-12742
No.-20736, JP-A-54-20737,
JP-A-54-21728, JP-A-54-22283
No. 4, JP-A-55-69148, JP-A-55-69148
-69654, JP-A-55-79449,
JP-A-55-117151, JP-A-56-462
No. 37, JP-A-56-116039, JP-A-56-116040, JP-A-56-119134
JP, JP-A-56-143437, JP-A-57-143637
-63537, JP-A-57-63538,
JP-A-57-63541, JP-A-57-6354
No. 2, JP-A-57-63549, JP-A-57-63549
-66438, JP-A-57-74746,
JP-A-57-78542, JP-A-57-7854
No. 3, JP-A-57-90056, JP-A-57-90056
-90057, JP-A-57-90632,
JP-A-57-116345, JP-A-57-202
349, JP-A-58-4151, and JP-A-5-5
JP-A-8-90644, JP-A-58-144358, JP-A-58-177555, JP-A-59-3
1962, JP-A-59-33253, JP-A-59-71059, JP-A-59-72448, JP-A-59-78356, JP-A-59-1
No. 36351, JP-A-59-201060,
JP-A-60-15624, JP-A-60-1403
No. 51, JP-A-60-179746, JP-A-61-11754, JP-A-61-90164, JP-A-61-90165, JP-A-61-90
166, JP-A-61-112154, JP-A-61-269165, and JP-A-61-28124.
No. 5, JP-A-61-51063, JP-A-62
-267363, JP-A-63-68844, JP-A-63-89866, JP-A-63-13
No. 9355, JP-A-63-142033, JP-A-63-183450, JP-A-63-2827
No. 43, JP-A-64-21455, JP-A-6-21
JP-A-4-78259, JP-A-1-200267, JP-A-1-202775, JP-A-1-319
754, JP-A-2-72372, JP-A-2-72372
-254467, JP-A-3-95561,
JP-A-3-278063, JP-A-4-96068
JP, JP-A-4-96069, JP-A-4-14
Compounds described in JP-A-7265, JP-A-5-142841, JP-A-5-303226, JP-A-6-324504, JP-A-7-168379 are exemplified.

The structure of the coupler component used in these azo pigments varies widely. For example, JP-A-54-17
735, JP-A-54-79632, JP-A-57-176055, JP-A-59-197043
JP, JP-A-60-130746, JP-A-60-130746
JP-153050, JP-A-60-103048, JP-A-60-189759, JP-A-63-1
No. 31146, JP-A-63-155052,
JP-A-2-110569, JP-A-4-14944
No. 8, JP-A-6-27705, JP-A-6-3
Compounds described in 48047 and the like can be mentioned.

Specific examples of the above azo pigments include B-1 shown below.
Examples include, but are not limited to, all compounds composed of combinations of the compounds shown in Tables 1 to 40 and the couplers shown in Tables 1 to 14. Further, these compounds can be used in combination with other charge generating substances.

[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

[Table 1]

[0047]

[Table 2]

[0048]

[Table 3]

[0049]

[Table 4]

[0050]

[Table 5]

[0051]

[Table 6]

[0052]

[Table 7]

[0053]

[Table 8]

[0054]

[Table 9]

[0055]

[Table 10]

[0056]

[Table 11]

[0057]

[Table 12]

[0058]

[Table 13]

[0059]

[Table 14]

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 by using the compound of the present invention, a metal drum, a metal plate, a sheet-like or drum-like or belt-like support of paper or plastic film subjected to conductive processing, and the like are used. You.

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 them, polystyrene resin, polyvinyl acetal resin, polycarbonate resin, polyester resin, polyarylate resin, and the like have excellent potential characteristics as a photoconductor. These resins can be used alone or as a mixture of one or more of them as a copolymer. The amount of the binder resin to be added to the photoconductive compound is 20 to 1000% by weight.
Is preferable, and 50 to 500% by weight is more preferable.

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.

Some of these resins include 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), phosphoric acid esters (eg, TCP, TOP, etc.), sebacic acid esters, adipic acid esters, nitrile rubber, chlorinated hydrocarbons and the like. If these substances are added unnecessarily, they adversely affect the electrophotographic properties. Therefore, the ratio is preferably 20% by weight or less based on the binder resin.

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

The enamine compound, which is an organic photoconductive material represented by the general formula (1) or (2), can be used in combination with another charge transport substance. The charge transport materials include a hole transport material and an electron transport material. Examples of the former include, for example, oxadiazoles disclosed in JP-B-34-5466, triphenylmethanes disclosed in JP-B-45-555, and JP-B-52-4188. And the like, hydrazones described in JP-B-55-42380, oxadiazoles described in JP-A-56-123544, and the like. On the other hand, examples of the electron transporting substance include chloranil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone,
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 is added as a sensitizer which forms a charge transfer complex with the enamine compound represented by the general formula (1) or (2) and further enhances the sensitizing effect. You can also. Examples of the electron-withdrawing compound include quinones such as 2,3-dichloro-1,4-naphthoquinone, 1-nitroanthraquinone, 1-chloro-5-nitroanthraquinone, 2-chloroanthraquinone, and phenanthrenequinone; Aldehydes such as benzaldehyde, ketones such as 9-benzoylanthracene, indandione, 3,5-dinitrobenzophenone, 3,3 ', 5,5'-tetranitrobenzophenone, phthalic anhydride, 4-chloronaphthalic anhydride and the like Acid anhydride, terephthalalmalononitrile,
Cyano compounds such as 9-anthrylmethylidenemalononitrile, 4-nitrobenzalmalonenitrile, 4- (p-nitrobenzoyloxy) benzalmalonenitrile,
Phthalides such as 3-benzalphthalide, 3- (α-cyano-p-nitrobenzal) phthalide, 3- (α-cyano-p-nitrobenzal) -4,5,6,7-tetrachlorophthalide and the like can be mentioned. it can.

The organic photoconductive material of the present invention is dissolved or dispersed in a suitable 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, Aprotic polar solvents such as N-methylpyrrolidone, dimethylsulfoxide and n-butanol, 2-propanol; , And the like alcohol solvents such Lumpur. These solvents may be used alone or
It can be used as a mixed solvent of at least one kind.

[0069]

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

[0070]

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Synthesis Example 1 Synthesis of Exemplified Compound C-24 N, N-dimethylformamide (DMF) 80 m in which 2.00 g of the aldehyde shown in the above (3) and 2.52 g of diethylbenzhydrylphosphonate were dissolved.
The potassium tert-butoxide was added to the 1 solution under stirring at room temperature.
30 g were added slowly. After stirring was continued for 30 minutes, the reaction solution was poured into 500 ml of ice water to stop the reaction, and an organic component was extracted with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography to obtain 1.99 g of compound C-24. Yield 7
0%. 152 ° C.

[0072]

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Synthesis Example 2 Synthesis of Exemplified Compound C-30 N, N-dimethylformamide (DMF) 30 m in which 1.71 g of the aldehyde shown in the above (4) and 1.51 g of diethylbenzhydrylphosphonate were dissolved.
To a solution of potassium t-butoxide in a solution of 0.1 l with stirring at room temperature.
66 g was added slowly. After stirring was continued for 30 minutes, the reaction solution was poured into 500 ml of ice water to stop the reaction, and an organic component was extracted with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography to obtain 1.20 g of compound C-30. Yield 5
0%. 158 ° C.

Synthesis Example 3 Synthesis of Exemplified Compound C-62 Five drops of acetic acid were added to a solution of 1.94 g of the aldehyde shown in the above (3) and 1.01 g of methylphenylhydrazine in 80 ml of ethanol while stirring at room temperature. added.
After stirring at 60 ° C. for 3 hours, the reaction solution was poured into 500 ml of ice water to stop the reaction, and an organic component was extracted with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography to obtain 1.94 g of a compound C-62. Yield 78%. Oily.

Example 1 One part by weight of an azo pigment (B-1, Cp = A-21) and 1 part by weight of a polyester resin (Vylon 200 manufactured by Toyobo) were mixed with 100 parts by weight of tetrahydrofuran, and mixed with glass beads using a paint conditioner. Dispersed for 2 hours. The dispersion thus obtained was applied on an aluminum-evaporated polyester using an applicator and dried to a film thickness of about 0.2 μm.
m of the charge generation layer was formed. Next, an enamine compound (exemplified compound C-01) was mixed with a polyarylate resin (U-Polymer manufactured by Unitika) at a weight ratio of 1: 1 to prepare a 10% by weight solution using dichloroethane as a solvent. Applied on the layer with an applicator to a film thickness of about 20μm
Was formed.

The electrophotographic characteristics of the laminated photoreceptor thus manufactured were evaluated using an electrostatic recording tester (SP-428 manufactured by Kawaguchi Electric). Measurement conditions: applied voltage -6 kV, static No. 3 (turntable rotation speed mode: 10 m / min)
). As a result, the charging potential (V0) was -780 V, and the half-life exposure amount (E1 / 2) was 1.2 lux / sec, which was a high sensitivity value.

Further, the same apparatus was used to evaluate the characteristics with respect to repeated use in which charging-discharging (discharging light: irradiation with white light at 400 lux × 1 second) was performed in one cycle. 5000
The change in the charged potential due to the repetition of
The 5000th charging potential (V0) was -760V, compared to the charging potential (V0) of -780V at the time of charging, and the characteristics were stable with almost no decrease in potential due to repetition. The first half-exposure dose (E1 / 2) is 1.2 lux / sec, whereas the 5000th half-exposure dose (E1 / 2) is 1.2 lux / sec.
It showed excellent characteristics without change in looks and seconds.

Examples 2 to 47 In place of the azo pigment (B-1, Cp = A-21) and Exemplified Compound C-01 of Example 1, Tables 15 and 16 were used.
Except for using the azo pigment and the enamine compound shown in (1), a photoreceptor was prepared in the same manner as in Example 1, and its characteristics were evaluated. The results are shown in Tables 15 and 16.

[0079]

[Table 15]

[0080]

[Table 16]

Example 48 One part by weight of an azo pigment (B-1, Cp = A-21) and 40 parts by weight of tetrahydrofuran were subjected to a dispersion treatment together with glass beads for 8 hours using a paint conditioner. An enamine compound (Exemplified Compound C-0) is added to the dispersion thus obtained.
1) 2.5 parts by weight, 10 parts by weight of a polycarbonate resin (PCZ-200 manufactured by Mitsubishi Gas Chemical Co., Ltd.) and 60 parts by weight of tetrahydrofuran were added, and the mixture was further subjected to a dispersion treatment for 30 minutes by a paint conditioner, and then aluminum was deposited by an applicator. It was applied on polyester to form a photosensitive layer 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 is +5
Changed to kV. As a result, the first charging potential (V0)
+ 400V, half-exposure (E1 / 2) 1.4 lux
Charge potential (V0) after repeating 5000 times for 400 seconds
V, half-exposure (E1 / 2): 1.4 lux / sec, showing excellent characteristics with high sensitivity and little change.

Examples 49 to 94 Instead of the azo pigment (B-12, Cp = A-21) and the exemplified compound C-01 of Example 48, azo pigments and enamine compounds shown in Tables 17 and 18 were used. Other than
A photoconductor was prepared in the same manner as in Example 48, and the characteristics were evaluated. The results are shown in Tables 17 and 18.

[0083]

[Table 17]

[0084]

[Table 18]

Examples 95 to 113 The same procedures as in Example 1 were carried out except that the azo pigment of Example 1 was replaced by a τ-type metal-free phthalocyanine, and the enamine compounds shown in Table 19 were used instead of Exemplified Compound C-01. Then, a photoreceptor was manufactured and its characteristics were evaluated. Table 19 shows the results.
Shown in

[0086]

[Table 19]

Examples 114 to 132 The procedure of Example 4 was repeated, except that the azo pigment of Example 48 was replaced with Y-type titanyloxyphthalocyanine, and the exemplified compound C-01 was replaced by an enamine compound shown in Table 20.
In the same manner as in No. 8, a photoreceptor was prepared and its characteristics were evaluated.
The results are shown in Table 20.

[0088]

[Table 20]

[0089]

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Comparative Example 1 A photoconductor was prepared and the characteristics were evaluated in the same manner as in Example 1, except that the comparative compound (5) shown above was used instead of the exemplary compound C-01 as the charge transporting substance. As a result, 1
The charge potential at the second time is (V0) -730V, the half-exposure amount (E1 / 2) is 3.9 lux · sec, which is low sensitivity.
The 000th charging potential (V0) was -500 V, the half-life exposure amount (E1 / 2) was 4.3 lux / sec, and a significant decrease in potential due to repetition was observed.

[0091]

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Comparative Example 2 A photoconductor was prepared and the characteristics were evaluated in the same manner as in Example 48, except that the comparative compound (6) shown above was used instead of the exemplary compound C-01 as the charge transporting substance. as a result,
The first charging potential (V0) is +300 V, the half-exposure amount (E1 / 2) is 3.6 lux / sec, which is low sensitivity.
The 000th charging potential (V0) was +115 V, the half-life exposure amount (E1 / 2) was 3.9 lux / sec, and a significant decrease in potential due to repetition was observed.

[0093]

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.

Claims (3)

[Claims] 1. An organic photoconductive material represented by the following general formula (1) or (2). Embedded image (In the general formula (1) or (2), R ₁ , R ₂ , R
₆ , R ₇ represent an alkyl group which may have a substituent, an aryl group, or a heterocyclic ring; R ₃ and R ₈ represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group; Represents a group. R ₄ and R ₅ represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group, or a heterocyclic group. However, one of R ₄ and R ₅ always has an aryl group or a heterocyclic ring. R ₉ and R ₁₀ represent an optionally substituted alkyl group, alkenyl group, aralkyl group, aryl group, or heterocyclic ring. m and n show the integer of 0-2. Z represents an atomic group necessary for forming a saturated hydrocarbon ring or a 5- to 8-membered heterocyclic ring with two carbons of the indoline ring. ) 2. A conductive support comprising a photosensitive layer containing one kind of the organic photoconductive material represented by the general formula (1) or (2) or two or more kinds thereof on a conductive support. An electrophotographic photoreceptor, comprising: 3. A photosensitive layer containing a charge generating substance and a charge transporting substance, wherein the charge transporting substance is an organic photoconductive material represented by the above general formula (1) or (2). The electrophotographic photosensitive member according to claim 2, wherein