JPH10239877A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prevent the lowering of potential by electrification, the lowering of sensitivity and the rise of residual potential due to repeated use as well as to enhance sensitivity by forming a photosensitive layer contg. specified compds. on an electrically conductive substrate. SOLUTION: A photosensitive layer contg. at least a compd. represented by formula I and one of compds. represented by formulae II, III, etc., is formed on an electrically conductive substrate to obtain the objective electrophotographic photoreceptor. In the formula I, R1 is H or halogen and R2 is an optionally substd. arom. residue or a heterocyclic residue. In the formula II, each of R1 and R3 is H, lower alkyl, lower alkoxy or di-lower alkylamino, R2 is H, lower alkyl, lower alkoxy, halogen or nitro and (n) is 0 or 1. In the formula III, R is carbazolyl, pyridyl, thienyl, indolyl, optionally substd. phenyl, optionally substd. styryl, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly to a high-sensitivity electrophotographic photoreceptor using a combination of specific charge-transporting materials and having good electrostatic characteristics and image characteristics in repeated use many times. The present invention relates to an electrophotographic photosensitive member having excellent repetition stability.

[0002]

2. Description of the Related Art A function-separated type electrophotographic photosensitive member having a photosensitive layer containing a charge generating material and a charge transporting material in order to enhance the sensitivity of an organic electrophotographic photosensitive member, particularly contains a charge generating material. A function-separated type electrophotographic photosensitive member in which a charge generating layer and a charge transporting layer containing a charge transporting material are laminated has attracted attention and has been put to practical use. The mechanism of formation of an electrostatic latent image in this function-separated type electrophotographic photosensitive member is as follows. That is, when the photoreceptor is charged and then irradiated with light, the light is absorbed by the charge generating material, and the charge generating material that has absorbed the light generates charge carriers, which are injected into the charge transport layer and generated by the charging. Move in the charge transport layer (or photosensitive layer) according to the electric field
An electrostatic latent image is formed by neutralizing the charge on the photoreceptor surface. Then, the electrostatic latent image thus formed on the surface of the photoreceptor is visualized by a developer such as toner, and the copied or recorded image is obtained by transferring the image to paper or the like. Electrophotographic photoreceptors include electrophotographic characteristics represented by sensitivity, receptive potential, potential retention, potential stability, residual potential, spectral characteristics, etc., mechanical durability such as abrasion resistance, heat, light, discharge Various properties such as chemical stability to products and the like are required. In particular, it is important that they have high sensitivity and excellent repetition stability. Traditionally,
A variety of charge generation materials and charge transport materials for use in function-separated electrophotographic photoreceptors have been developed, and a certain degree of sensitization has been achieved by appropriate combinations of charge generation materials and charge transport materials. When the body is used many times, the charge potential decreases, the sensitivity decreases, the residual potential increases, etc., and the photosensitive layer film deteriorates, such as peeling of the photosensitive layer or cracks, and image defects in the copied or recorded image, Insufficient repetition stability such as occurrence of soiling.

[0003]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to solve such a problem, to provide a high sensitivity and to reduce the charging potential, the sensitivity, and the residual potential even when used repeatedly many times. An object of the present invention is to provide an electrophotographic photoreceptor excellent in repetition stability, in which rise and the like are less likely to occur, and there is no deterioration of a photosensitive layer film and no occurrence of image defects or background contamination of a copied or recorded image.

[0004]

The object of the present invention is to provide at least one of a compound represented by the following general formula (1) and a compound represented by the following general formulas (2) to (32) on a conductive support. This is achieved by an electrophotographic photoreceptor comprising a photosensitive layer containing a seed.

Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) ]

Embedded image (Wherein R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group;
₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. n represents 0 or 1. )

Embedded image [Wherein, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group or a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, wherein the substituent is a di-lower alkylamino group; , A lower alkyl group, a lower alkoxy group, a halogen atom, an aralkylamino group and an amino group.). ]

Embedded image (In the formula, R ₁ , R ₂ , and R ₃ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenoxy group, or a halogen atom.)

Embedded image [In the formula, R ₁ represents a hydrogen atom, a halogen atom, a cyano group, or a lower alkyl group, and Ar represents the following general formula (a) or (b)

Embedded image (However, R ₂ , R ₃ and R ₆ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted benzyl group, and R ₄ and R ₅ represent a hydrogen atom, a halogen atom, a lower alkyl group, Represents a lower alkoxy group or a di-lower alkylamino group). ]

Embedded image (Wherein R ₁ , R ₂ , R ₃ , R ₄ and R ₆ represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted di-lower alkylamino group or a dibenzylamino group. , R ₅ represents a lower alkyl group or a benzyl group.)

Embedded image (In the formula, Ar represents a naphthalene ring, an anthracene ring, a pyrene ring, a styryl group or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents a lower alkyl group or a benzyl group.)

Embedded image (Wherein, R ₁ represents a lower alkyl group, a 2-hydroxyethyl group or a 2-chloroethyl group, R ₂ represents a lower alkyl group, a benzyl group or a phenyl group, and R ₃ represents a hydrogen atom, a halogen atom, a lower alkyl group. Group, lower alkoxy group, di-lower alkylamino group or nitro group.)

Embedded image (Wherein, R ₁ represents a hydrogen atom, a lower alkyl group, a chloroethyl group or a hydroxyethyl group, R ₂ represents a hydrogen atom or a halogen atom, and R ₃ represents a lower alkyl group, a di-lower alkylamino group, a diarylamino group. Represents a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue, or a substituted or unsubstituted heterocyclic residue.) Examples of the aromatic ring of the aromatic ring residue include a benzene ring, a naphthalene ring, and an anthracene ring. And the heterocyclic ring of the heterocyclic residue includes a pyridine ring, a quinoxaline ring, a carbazole ring and the like.

Embedded image (Wherein, R ₁ represents a lower alkyl group, R ₂ represents a lower alkyl group, a di-lower alkylamino group, a diarylamino group,
Represents a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue, or a substituted or unsubstituted heterocyclic residue. Examples of the aromatic ring of the aromatic ring residue include a benzene ring, a naphthalene ring, and an anthracene ring, and examples of the heterocyclic ring of the heterocyclic residue include a pyridine ring, a quinoxaline ring, and a carbazole ring.

Embedded image (Wherein R ₁ and R ₂ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group, a chloro lower alkyl group, an alkyl group having 1 to 2 carbon atoms, an alkyl group having 1 to 2 carbon atoms) Represents 5 to 6 cycloalkyl groups or substituted or unsubstituted aralkyl groups.)

Embedded image (Wherein R ₁ , R ₃ and R ₄ are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom or a substituted or unsubstituted R ₂ represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, provided that R ₁ ,
R ₂ , R ₃ and R ₄ are not all hydrogen atoms. Further, k, l, m and n are integers of ₁ , ₂ , 3 or 4, and when each is an integer of 2, 3 or 4, R ₁ , R ₂ ,
R ₃ and R ₄ may be the same or different. )

Embedded image A-CH ₂ CH ₂ —Ar 1 —CH ₂ CH ₂ —A (13) [wherein, Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, A represents a substituted or unsubstituted N-substituted carbazolyl group or the following general formula (c)

Embedded image (However, Ar ₂ is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, and R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ). ]

Embedded image (Wherein R ₁ is a hydrogen atom, an alkyl group, an alkoxy group,
Represents an aryloxy group, a dialkylamino group, a diarylamino group or a halogen atom, R ₂ and R ₃ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and Ar represents an aromatic hydrocarbon group or a heterocyclic group. Represents a ring group. n represents an integer of 1 or 2. )

Embedded image (Wherein R ₁ and R ₂ are a hydrogen atom, an amino group, a substituted or unsubstituted dialkylamino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted R ₃ and R ₄ represent a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and Ar represents a substituted or unsubstituted monocyclic aromatic hydrocarbon group, a substituted or unsubstituted group. Represents a substituted non-fused polycyclic aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group.)

Embedded image [Wherein A is an N-substituted carbazolyl group or the following general formula (d)

Embedded image (However, Ar is an aromatic hydrocarbon group or a heterocyclic group,
R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ), And R represents an alkyl group, an alkoxy group, or a halogen atom. n represents an integer of 0 to 4, and when n is 2 or more, Rs may be the same or different. ]

Embedded image [Wherein A is a 9-anthryl group, a substituted or unsubstituted N-substituted carbazolyl group, an N-substituted phenothiazinyl group, or a compound represented by the following general formula (e):

Embedded image (However, Ar represents a substituted or unsubstituted arylene group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.) And R represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. m represents an integer of 2 to 8, and n represents an integer of 0 or 1. ]

Embedded image [In the formula, A represents a 9-anthryl group, a substituted or unsubstituted N-substituted carbazolyl group, an N-substituted phenothiazinyl group, or the following general formula (f)

Embedded image (However, Ar represents a substituted or unsubstituted arylene group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.) And R represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. n represents the integer of 0-8. ]

Embedded image (In the formula, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different.)

Embedded image (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and at least one of R ₁ and R ₂ represents a substituted or unsubstituted aryl group.)

Embedded image (Wherein, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₁ and R ₂ may be the same or different. R ₃ and R ₄ are hydrogen atoms , An alkyl group, an alkoxy group or a halogen atom, m represents an integer of 1, 2, or 3, n represents an integer of 1, 2, 3, or 4. When m or n is 2 or more, R ₃ , R ₄ may be the same or different.)

Embedded image (In the formula, m represents an integer of 0 or 1, and when m is 1, X
An oxygen atom, a sulfur _{atom, -CH 2 -, - CH 2} CH 2 -,
Represents -CH = CH- or -N (R)-(where R represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group). R ₁ and R ₂ represent an alkyl group, an aralkyl group, a carbocyclic aromatic group or a heterocyclic group, and R ₃ and R ₄ represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Ar represents a carbocyclic aromatic group or a heterocyclic group. n represents an integer of 0 or 1. R ₃ may form a benzene ring with X. )

Embedded image (In the formula, Ar represents a substituted or unsubstituted biphenylene group, and R ₁ , R _2, and R ₃ represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group, an alkoxy group, or an aryl group. Represents an oxy group, an alkylmercapto group, a methylenedioxy group, a methylenedithio group, or an aryl group, and R ₁ , R ₂ and R ₃ may be the same or different, and l, m and n are integers of 1 to 5 Represents each of 2 to
When it is an integer of 5, R ₁ , R ₂ and R ₃ may be the same or different. )

Embedded image (In the formula, Ar represents a phenylene group or a biphenylene group, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and n represents an integer of 1 to 4.)

Embedded image (In the formula, A ₁ and A ₂ each represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different. Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon. Represents a group.)

Embedded image (Wherein R ₁ and R ₂ are a substituted or unsubstituted alkyl group,
Represents a substituted or unsubstituted aryl group, wherein n is 1 or 2
Represents an integer. R ₃ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ₄ and R ₅ represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a substituted or unsubstituted alkyl group, or a halogen atom. m represents an integer of 1, 2, and 3, and 1 represents an integer of 1, 2, 3, and 4. l, m
Is an integer of 2 or more, R ₄ and R ₅ may be the same or different. )

Embedded image (Wherein, R ₁ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₂ , R ₃ , and R ₄ represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group , A methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, a substituted or unsubstituted aryl group, h represents an integer of 1, 2, 3, and 4, and k and l represent 1, 2, 3 Represents an integer of 4, 5;
When h, k, and l are integers of 2 or more, R ₂ , R ₃ , and R ₄ may be the same or different. n represents an integer of 1, 2, 3, and 4, and m represents an integer of 4-n. When m is 2 or more, R
₁ may be the same or different. )

Embedded image (In the formula, A ₁ represents a substituted or unsubstituted aromatic hydrocarbon group, A ₂ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and A3 represents a hydrogen atom, a substituted or unsubstituted group. Represents an alkyl group or a substituted or unsubstituted aryl group, wherein m and n represent an integer of 1 or 2, and m + n is 3, provided that m or n is 2
At this time, A ₁ , A 3 or A ₂ may be the same or different. )

Embedded image (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different, except for a 1,6-diaminopyrene compound. )

Embedded image (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.)

Embedded image (Wherein, R represents a lower alkyl group or a benzyl group;
Represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, or an amino group substituted with a lower alkyl group or a benzyl group. n represents an integer of 1 or 2. )

Embedded image (Wherein, R ₁ and R ₂ represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a substituted or unsubstituted alkyl group, and R ₃ and R ₄ represent a hydrogen atom, a cyano group, an alkoxycarbonyl group, It represents an unsubstituted alkyl group, R ₅
Represents a hydrogen atom, a lower alkyl group or an alkoxy group.
W represents a hydrogen atom or a substituted or unsubstituted alkyl group. j is an integer of 1 to 5, k is an integer of 1 to 4, l is 0 to 2
M represents an integer of 1 or 2, and n represents an integer of 1 to 3. )

According to the present invention, by using a combination of the above-mentioned specific compounds as a charge transporting material in a photosensitive layer, the photosensitive layer has high sensitivity. Less occurrence of potential rise, etc., no deterioration of the photosensitive layer film such as peeling or cracking of the photosensitive layer, no image defects of copy or recorded image or background stain, and excellent repetition stability An electrophotographic photoreceptor can be obtained. The compound represented by the general formula (1) and the compounds represented by the general formulas (2) to (32) are disclosed in, for example, JP-A-2-272569 and JP-A-2-272570. It has not been found that the use of a specific combination as described above produces a special effect of suppressing the occurrence of image defects due to the deterioration of the photosensitive layer as described above.

[0006]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
FIG. 1 is a sectional view showing an electrophotographic photosensitive member having a single-layer photosensitive layer. A single-layer photosensitive layer 15 is provided on a conductive support 11. FIGS. 2 and 3 are cross-sectional views showing an example of the configuration of an electrophotographic photoreceptor having a laminated photosensitive layer. The charge generating layer 17 mainly composed of a charge generation material and the charge transport layer 19 mainly composed of a charge transport material are shown. Are laminated. The single layer photosensitive layer 15 or the charge transport layer 19 in the laminated photosensitive layer contains a charge transport material composed of a combination of the above specific compounds. Conductive support 11
As a material having a conductivity of 10 ¹⁰ Ωcm or less, for example, a metal such as aluminum, nickel, chromium, nichrome, copper, silver, gold, platinum, or a metal oxide such as tin oxide or indium oxide, Film or cylindrical plastic or paper coated by vapor deposition or sputtering, or plates made of aluminum, aluminum alloy, nickel, stainless steel, etc., and after making them into a tube, surface-treated by cutting, super finishing, polishing, etc. A tube or the like can be used.

Next, regarding the photosensitive layer, first, the charge generation layer 17
The structure of the laminated photosensitive layer in which the charge transport layer 19 and the charge transport layer 19 are laminated will be described. The charge generation layer 17 is a layer containing a charge generation material as a main component, and any of an inorganic or organic charge generation material can be used as the charge generation material. Representative examples of the charge generation material include monoazo pigments, disazo pigments, trisazo pigments, perylene pigments, perinone pigments, quinacridone pigments, quinone condensed polycyclic compounds, squaric acid dyes, phthalocyanine pigments, and naphthalocyanine pigments , Selenium, selenium-tellurium, selenium-arsenic alloy, amorphous silicon, etc., and these may be used alone or in combination of two or more.

In order to form the charge generation layer 17, a charge milling material is added to a ball mill, an attritor, or the like, using a suitable solvent such as tetrahydrofuran, cyclohexanone, dioxane, 2-butanone, or dichloroethane, together with a binder resin, if necessary. What is necessary is just to disperse by a sand mill or the like, apply the dispersion on a conductive support or a charge transport layer, and dry the dispersion. As a method of applying the dispersion,
Dip coating, spray coating, bead coating, and the like can be used. As the binder resin used as needed, polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate,
Examples include silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polyacrylamide, and the like. The amount of the binder resin used is suitably 2 parts by weight or less based on 1 part by weight of the charge generating material. The charge generation layer 17 can also be formed by a known vacuum thin film manufacturing method. The thickness of the charge generation layer 17 is suitably about 0.01 to 5 μm, and particularly preferably 0.1 to 2 μm.

To form the charge transport layer 19, the compound represented by the general formula (1) and one of the compounds represented by the general formulas (2) to (32) are dissolved in a suitable solvent together with a binder resin. The dispersion may be dispersed to prepare a coating liquid for a charge transport layer, which may be coated on a conductive support or a charge generation layer and dried. The mixing ratio between the compound represented by the general formula (1) and the compounds represented by the general formulas (2) to (32) is determined by using the compound represented by the general formula (1) and the compound represented by the general formulas (2) to (32). It is preferable that at least one selected from the compounds shown is in the range of 5:95 to 95: 5.

The binder resin used for the charge transport layer 19 includes polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, and vinyl chloride. Vinyl acetate copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, acrylic resin, silicone resin, epoxy resin, melamine resin, Thermoplastic or thermosetting resins such as urethane resins, phenolic resins, and alkyd resins. As a solvent used when preparing the coating solution for the charge transport layer, tetrahydrofuran,
Examples thereof include dioxane, toluene, 2-butanone, monochlorobenzene, dichloroethane, and methylene chloride.

The charge transport layer 19 includes, in addition to the compound represented by the general formula (1) and the compounds represented by the general formulas (2) to (32), a known electron transporting charge transporting material and / or a hole. A transportable charge transporting material may be added, and a plasticizer or a leveling agent may be added. As the plasticizer, those used as general plasticizers for general resins, such as dibutyl phthalate and dioctyl phthalate, can be used as they are.
0% by weight or less is appropriate. As the leveling agent, silicone oils such as dimethyl silicone oil and methyl phenyl silicone oil, and a polymer or oligomer having a perfluoroalkyl group in a side chain are used.
The following are appropriate: The thickness of the charge transport layer 19 is 5
About 100 μm is preferable.

Next, the single-layer photosensitive layer 15 will be described. In order to form the single-layer photosensitive layer 15, at least the charge generating material and the compound represented by the general formula (1) and one of the compounds represented by the general formulas (2) to (32) are combined with a binder resin and a suitable solvent. May be dissolved or dispersed, and then applied to a conductive support or the like and dried. As the binder resin, the binder resin described for the charge transport layer 19 can be used as it is, or the binder resin described for the charge generation layer 17 may be used as a mixture.
Further, a compound represented by the general formula (1) and one of the compounds represented by the general formulas (2) to (32) are added to a eutectic complex formed from a pyrylium-based dye and a bisphenol A-based polycarbonate to form a single crystal. A photosensitive layer can also be formed. Furthermore, a single-layer photosensitive material containing a binder resin, a compound represented by the general formula (1) and one of the compounds represented by the general formulas (2) to (32) as main components and not including a charge generating material as an active ingredient. The layer is also useful as a photosensitive layer having sensitivity to blue light to ultraviolet light. The compound represented by the general formula (1) and the general formulas (2) to (3) in the single-layer photosensitive layer
The mixing ratio with the compound represented by 2) is from 5:95 to
A range of 95: 5 is preferred. The thickness of the single-layer photosensitive layer is suitably about 5 to 100 μm.

Specific examples of the compound represented by the general formula (1) and the compounds represented by the general formulas (2) to (32) are shown in Tables 1 and 2 to 32 below.

[0014]

[Table 1-1]

[0015]

[Table 1-2]

[0016]

[Table 2-1]

[0017]

[Table 2-2]

[0018]

[Table 3-1]

[0019]

[Table 3-2]

[0020]

[Table 3-3]

[0021]

[Table 3-4]

[0022]

[Table 4-1]

[0023]

[Table 4-2]

[0024]

[Table 5-1]

[0025]

[Table 5-2]

[0026]

[Table 5-3]

[0027]

[Table 5-4]

[0028]

[Table 6-1]

[0029]

[Table 6-2]

[0030]

[Table 6-3]

[0031]

[Table 6-4]

[0032]

[Table 6-5]

[0033]

[Table 7-1]

[0034]

[Table 7-2]

[0035]

[Table 8-1]

[0036]

[Table 8-2]

[0037]

[Table 9-1]

[0038]

[Table 9-2]

[0039]

[Table 9-3]

[0040]

[Table 9-4]

[0041]

[Table 9-5]

[0042]

[Table 9-6]

[0043]

[Table 9-7]

[0044]

[Table 9-8]

[0045]

[Table 9-9]

[0046]

[Table 10-1]

[0047]

[Table 10-2]

[0048]

[Table 10-3]

[0049]

[Table 10-4]

[0050]

[Table 11]

[0051]

[Table 12-1]

[0052]

[Table 12-2]

[0053]

[Table 12-3]

[0054]

[Table 12-4]

[0055]

[Table 12-5]

[0056]

[Table 13-1]

[0057]

[Table 13-2]

[0058]

[Table 13-3]

[0059]

[Table 13-4]

[0060]

[Table 13-5]

[0061]

[Table 13-6]

[0062]

[Table 13-7]

[0063]

[Table 13-8]

[0064]

[Table 13-9]

[0065]

[Table 13-10]

[0066]

[Table 13-11]

[0067]

[Table 13-12]

[0068]

[Table 13-13]

[0069]

[Table 13-14]

[0070]

[Table 13-15]

[0071]

[Table 13-16]

[0072]

[Table 13-17]

[0073]

[Table 13-18]

[0074]

[Table 13-19]

[0075]

[Table 13-20]

[0076]

[Table 13-21]

[0077]

[Table 13-22]

[0078]

[Table 13-23]

[0079]

[Table 13-24]

[0080]

[Table 13-25]

[0081]

[Table 13-26]

[0082]

[Table 13-27]

[0083]

[Table 13-28]

[0084]

[Table 13-29]

[0085]

[Table 13-30]

[0086]

[Table 13-31]

[0087]

[Table 13-32]

[0088]

[Table 13-33]

[0089]

Table 13-34

[0090]

[Table 13-35]

[0091]

[Table 13-36]

[0092]

[Table 13-37]

[0093]

[Table 13-38]

[0094]

Table 13-39

[0095]

[Table 13-40]

[0096]

[Table 13-41]

[0097]

Table 13-42

[0098]

[Table 13-43]

[0099]

[Table 14-1]

[0100]

[Table 14-2]

[0101]

[Table 14-3]

[0102]

[Table 14-4]

[0103]

[Table 14-5]

[0104]

[Table 14-6]

[0105]

[Table 14-7]

[0106]

[Table 14-8]

[0107]

[Table 14-9]

[0108]

[Table 14-10]

[0109]

[Table 14-11]

[0110]

[Table 14-12]

[0111]

[Table 15-1]

[0112]

[Table 15-2]

[0113]

[Table 15-3]

[0114]

[Table 15-4]

[0115]

[Table 15-5]

[0116]

[Table 15-6]

[0117]

[Table 15-7]

[0118]

[Table 15-8]

[0119]

[Table 15-9]

[0120]

[Table 15-10]

[0121]

[Table 15-11]

[0122]

[Table 15-12]

[0123]

[Table 15-13]

[0124]

[Table 15-14]

[0125]

[Table 15-15]

[0126]

[Table 15-16]

[0127]

[Table 15-17]

[0128]

[Table 16-1]

[0129]

[Table 16-2]

[0130]

[Table 16-3]

[0131]

[Table 16-4]

[0132]

[Table 16-5]

[0133]

[Table 16-6]

[0134]

[Table 16-7]

[0135]

[Table 16-8]

[0136]

[Table 16-9]

[0137]

[Table 17-1]

[0138]

[Table 17-2]

[0139]

[Table 17-3]

[0140]

[Table 17-4]

[0141]

[Table 17-5]

[0142]

[Table 17-6]

[0143]

[Table 17-7]

[0144]

[Table 17-8]

[0145]

[Table 17-9]

[0146]

[Table 17-10]

[0147]

[Table 17-11]

[0148]

[Table 17-12]

[0149]

[Table 17-13]

[0150]

[Table 17-14]

[0151]

[Table 17-15]

[0152]

[Table 17-16]

[0153]

[Table 17-17]

[0154]

[Table 17-18]

[0155]

[Table 18-1]

[0156]

[Table 18-2]

[0157]

[Table 18-3]

[0158]

[Table 18-4]

[0159]

[Table 18-5]

[0160]

[Table 18-6]

[0161]

[Table 19-1]

[0162]

[Table 19-2]

[0163]

[Table 20-1]

[0164]

[Table 20-2]

[0165]

[Table 21-1]

[0166]

[Table 21-2]

[0167]

[Table 21-3]

[0168]

[Table 21-4]

[0169]

[Table 22-1]

[0170]

[Table 22-2]

[0171]

[Table 22-3]

[0172]

[Table 22-4]

[0173]

[Table 22-5]

[0174]

[Table 22-6]

[0175]

[Table 22-7]

[0176]

[Table 22-8]

[0177]

[Table 22-9]

[0178]

[Table 22-10]

[0179]

[Table 22-11]

[0180]

[Table 23-1]

[0181]

[Table 23-2]

[0182]

[Table 23-3]

[0183]

[Table 23-4]

[0184]

[Table 24-1]

[0185]

[Table 24-2]

[0186]

[Table 25-1]

[0187]

[Table 25-2]

[0188]

[Table 25-3]

[0189]

[Table 25-4]

[0190]

[Table 25-5]

[0191]

[Table 25-6]

[0192]

[Table 25-7]

[0193]

[Table 26-1]

[0194]

[Table 26-2]

[0195]

[Table 27-1]

[0196]

[Table 27-2]

[0197]

[Table 27-3]

[0198]

[Table 27-4]

[0199]

[Table 28-1]

[0200]

[Table 28-2]

[0201]

[Table 28-3]

[0202]

[Table 28-4]

[0203]

[Table 29-1]

[0204]

[Table 29-2]

[0205]

[Table 29-3]

[0206]

[Table 29-4]

[0207]

[Table 29-5]

[0208]

[Table 29-6]

[0209]

[Table 30-1]

[0210]

[Table 30-2]

[0211]

[Table 30-3]

[0212]

[Table 30-4]

[0213]

[Table 31-1]

[0214]

[Table 31-2]

[0215]

[Table 31-3]

[0216]

[Table 31-4]

[0219]

[Table 31-5]

[0218]

[Table 31-6]

[0219]

[Table 31-7]

[0220]

[Table 31-8]

[0221]

[Table 31-9]

[0222]

[Table 32-1]

[0223]

[Table 32-2]

[0224]

[Table 32-3]

[0225]

[Table 32-4]

[0226]

[Table 32-5]

[0227]

[Table 32-6]

[0228]

[Table 32-7]

[0229]

[Table 32-8]

In the electrophotographic photosensitive member of the present invention, an undercoat layer can be provided between the conductive support 11 and the photosensitive layer. The undercoat layer generally contains a resin as a main component. However, considering that the photosensitive layer is coated thereon with a solvent, these resins are resins having high solubility resistance to general organic solvents. desirable. Such resins include polyvinyl alcohol, casein, water-soluble resins such as sodium polyacrylate, copolymerized nylon, alcohol-soluble resins such as methoxymethylated nylon, polyurethane, melamine resin, alkyd-melamine resin, epoxy resin, and the like. Curable resins that form a three-dimensional network structure are exemplified. Further, a fine powder of a metal oxide exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide, or the like may be added to the undercoat layer in order to prevent moire and reduce residual potential. These underlayers
It can be formed using an appropriate solvent and a coating method as in the case of the above-mentioned photosensitive layer. Further, as the undercoat layer, a metal oxide layer formed by a sol-gel method using a silane coupling agent, a titanium coupling agent, a chromium coupling agent, or the like is also useful. In addition, the undercoat layer of the present invention is provided with Al ₂ O ₃ by anodic oxidation, an organic substance such as polyparaxylylene (parylene), SiO, SnO, or the like.
₂ , inorganic materials such as TiO ₂ , ITO, and CeO ₂ provided by a vacuum thin film manufacturing method can also be used favorably. An appropriate thickness of the undercoat layer is 5 μm or less.

In the electrophotographic photosensitive member of the present invention, a protective layer may be provided on the photosensitive layer for the purpose of protecting the photosensitive layer.
Materials used for this include ABS resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenolic resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallyl sulfone, polybutylene, Polybutylene terephthalate, polycarbonate, polyether sulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide, polysulfone, A
Examples of the resin include resins such as S resin, AB resin, BS resin, polyurethane, polyvinyl chloride, polyvinylidene chloride, and epoxy resin. For the purpose of improving abrasion resistance, the protective layer may be made of a fluororesin such as polytetrafluoroethylene, a silicone resin, or a material in which an inorganic material such as titanium oxide, tin oxide or potassium titanate is dispersed in these resins. Can be added. As a method of forming the protective layer,
A normal coating method is employed. The thickness of the protective layer is
About 0.5 to 10 μm is appropriate. In addition to the above, known materials such as iC and a-SiC formed by a vacuum thin film manufacturing method can also be used as the protective layer.

Further, in the electrophotographic photosensitive member of the present invention, another intermediate layer can be provided between the photosensitive layer and the protective layer. The intermediate layer generally uses a binder resin as a main component, and examples of these resins include polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, and polyvinyl alcohol. As a method for forming the intermediate layer, a normal coating method is employed as described above. The thickness of the intermediate layer is 0.05 to 2 μm.
About m is appropriate.

[0233]

The present invention will now be described in more detail with reference to the following Examples, which are provided only for illustrating the present invention in detail and do not limit the present invention. All parts in the examples are parts by weight.

Example 1 An undercoat layer coating solution, a charge generation layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied on an aluminum cylinder having an outer diameter of 70 mm, and dried to form a layer having a thickness of 4 μm. Coating layer, 0.2μ
m and a charge transport layer having a thickness of 25 μm were formed to prepare an electrophotographic photosensitive member of the present invention. [Coating solution for undercoat layer] Oil-free alkyd resin (Dainippon Ink and Chemical: Beckolite M6401) 15 parts Melamine resin (Dainippon Ink and Chemical: Super Beckamine G-821) 10 parts Titanium dioxide (Ishihara Sangyo) 55 parts 2-butanone 40 parts [Coating solution for charge generation layer] 5 parts of charge generation material of the following structural formula (A)

[0235]

Embedded image Polyvinyl butyral resin (Denka Butyral # 5000-A, manufactured by Denki Kagaku Kogyo Co., Ltd.) 2 parts Cyclohexanone 200 parts 4-methyl-2-pentanone 150 parts [Coating solution for charge transport layer] Compound 3 of Table 10-1 Compound of 5 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Tetrahydrofuran 75 parts

Comparative Example 1 In the coating liquid for the charge transport layer of Example 1, the compound No. Except for compound No. 5, compound No. 5 in Table 1-1. 10
An electrophotographic photoreceptor of a comparative example was prepared in the same manner as in Example 1 except that 9 parts of the compound was used.

Examples 2-31 In the coating liquid for the charge transport layer of Example 1, the compound No. An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 1, except that the respective compounds shown in Table 33 below were used instead of the compound of No. 5.

[0238]

[Table 33]

Example 32 After the surface of an aluminum cylinder was anodized, a sealing treatment was performed. On this, the following charge generation layer coating solution,
The charge transport layer coating liquid is sequentially applied and dried to a thickness of 0.2 μm.
An electrophotographic photoreceptor of the present invention was prepared by forming a charge generation layer of m and a charge transport layer of 22 μm. [Coating solution for charge generation layer] 3 parts of charge generation material of the following structural formula (B)

[0240]

Embedded image Polyvinyl butyral resin (manufactured by Sekisui Chemical Co., Ltd .: ESLEC BL-S) 1 part Cyclohexanone 250 parts Tetrahydrofuran 50 parts [Charge transport layer coating solution] The compound No. in the above Table 1-1. Compound 2 of Part 2 Compound No. 12 of Table 2-1 8 parts 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Methylene chloride 80 parts

Comparative Example 2 In the coating liquid for the charge transport layer of Example 32, the compound No. Example 3 except that 12 compounds were not added
In the same manner as in Example 2, an electrophotographic photosensitive member of Comparative Example was produced.

Examples 33 to 62 In the coating solution for the charge transporting layer of Example 32, the compound Nos. 12 and the compound No. in Table 2-1.
An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 32 except that the respective compounds shown in Table 34 below were used in place of the compound of No. 8.

[0243]

[Table 34]

Comparative Examples 3 to 32 Examples 33 to 6 were carried out except that the compound of the general formula (1) was not added to the charge transport layer coating liquids of Examples 33 to 62.
In the same manner as in Example 2, an electrophotographic photosensitive member of Comparative Example was produced.

Example 63 An undercoat layer coating solution, a charge generation layer coating solution and a charge transport layer coating solution having the following composition were sequentially applied on an aluminum cylinder and dried to form a 2.5 μm thick undercoat layer. , And a charge transport layer of 0.2 μm and a charge transport layer of 27 μm to form an electrophotographic photoreceptor of the present invention. [Undercoat layer coating solution] Alcohol-soluble nylon (Toray: Amilan CM-8000) 10 parts Titanium dioxide (Ishihara Sangyo: Taipaque TA-300) 40 parts Methanol 120 parts Isopropanol 60 parts [Charge generation layer coating Liquid] 3 parts of a charge generating material of the following structural formula (C)

[0246]

Embedded image Polyester (manufactured by Toyobo Co., Ltd .: Byron 200) 1 part Cyclohexanone 150 parts Cyclohexane 100 parts [Coating solution for charge transport layer] Compound No. in the above Table 1-1. Compound No. 5 4 parts Compound No. in the above Table 2-2. 10 compounds 4 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Comparative Example 33 In the coating liquid for the charge transporting layer of Example 63, Compound No. Compound No. 5 in Table 2-2 except for Compound No. 5 1
An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 63 except that 8 parts of Compound 0 was used.

Examples 64 to 93 In the coating liquid for the charge transporting layer of Example 63, the compound Nos. Compound No. 5 and Compound No. 5 in Table 2-2. 1
An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 63 except that each compound shown in Table 35 below was used in place of the compound No. 0.

[0249]

[Table 35]

Comparative Examples 34 to 63 The same procedures as in Examples 64 to 93 were carried out except that 8 parts of the compounds of the general formulas (2) to (32) were used except for the compound of the general formula (1). An electrophotographic photosensitive member of a comparative example was produced in the same manner as in Examples 64 to 93.

Example 94 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 21 μm, thereby producing an electrophotographic photosensitive member of the present invention. [Coating solution for photosensitive layer] 4 parts of charge generating material of the following structural formula (D)

[0252]

Embedded image Polycarbonate (Mitsubishi Gas Chemical Co., Ltd .: Iupilon S-2000) 20 parts Compound No. 1 in Table 1-2 above. Compound No. 14 6 parts Compound No. 9 compound 10 parts cyclohexanone 100 parts tetrahydrofuran 150 parts Comparative Example 64 In the photosensitive layer coating liquid of Example 94, compound N of Table 1-2
o. An electrophotographic photoreceptor of a comparative example was prepared in the same manner as in Example 94 except that Compound 14 was not added.

Examples 95 to 124 In the photosensitive layer coating solution of Example 94, the compound Nos. 14 and the compound No. of Table 2-2. An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 94, except that the respective compounds shown in Table 36 below were used instead of the compound of No. 9.

[0254]

[Table 36]

Comparative Examples 65 to 94 Examples 95 to 124 except that the compound of the formula (1) was not added to the photosensitive layer coating solutions of Examples 95 to 124.
In the same manner as in Example 24, an electrophotographic photosensitive member of Comparative Example was produced.

Comparative Example 95 In the coating liquid for the charge transport layer of Example 1, the compound No. An electrophotographic photoreceptor of a comparative example was prepared in the same manner as in Example 1, except that the compound of the following structural formula (E) was used instead of the compound of No. 5.

[0257]

Embedded image

Comparative Example 96 In the coating solution for the charge transport layer of Example 63, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 63 except that the compound of the following structural formula (F) was used instead of the compound of No. 10.

[0259]

Embedded image For each of the electrophotographic photoreceptors obtained in the above Examples and Comparative Examples, the characteristics of the photoreceptors were measured as follows using an evaluation apparatus disclosed in Japanese Patent Application Laid-Open No. 60-100167. Corona discharge voltage -6.0 kV (or +
5.6 kV), a potential Vm (V) after charging for 20 seconds, a potential Vo (V) after dark decay for 20 seconds, and an exposure amount E1 / 2 (lux · sec) required to attenuate the potential Vo to １ ／. ) Was measured. The potential holding ratio is defined as Vo / Vm. Each electrophotographic photoreceptor was mounted on an electrophotographic copying machine (FT-3300, manufactured by Ricoh Co., Ltd. or modified so that the photoreceptor could be positively charged) to continuously copy 30,000 sheets, and image defects ( The presence or absence of an abnormal image was visually determined. Further, for each electrophotographic photosensitive member after the completion of the copying test, Vm (V), Vo (V), E1 / 2 (lux · s) were obtained in the same manner as described above.
ec) was measured. The results are shown in Tables 37-44.

[0260]

[Table 37]

[0261]

[Table 38]

[0262]

[Table 39]

[0263]

[Table 40]

[0264]

[Table 41]

[0265]

[Table 42]

[0266]

[Table 43]

[0267]

[Table 44]

As is clear from Tables 37 to 44, the electrophotographic photoreceptors of the examples have high sensitivity, and the charge potential and the sensitivity are small even when used repeatedly many times. The electrophotographic photoreceptor of the comparative example is inferior in at least one of these, while there is no occurrence of abrasion scratches and no image defect or background stain of a copied image.

[0269]

According to the present invention, by using a combination of the above two specific compounds as a charge transporting material for a photosensitive layer, the photosensitive layer has high sensitivity, and the charging potential is reduced even when used repeatedly many times. There are few occurrences such as decrease in sensitivity, increase in residual potential, etc., and there is no deterioration of the photosensitive layer film such as peeling of the photosensitive layer, abrasion scratches and cracks, and the occurrence of image defects and background stains on copied or recorded images. And an electrophotographic photoreceptor having excellent repetition stability can be obtained.

[Brief description of the drawings]

FIG. 1 is an explanatory view schematically showing an electrophotographic photosensitive member having a single-layer photosensitive layer.

FIG. 2 is an explanatory view schematically showing an electrophotographic photosensitive member having a laminated photosensitive layer.

FIG. 3 is an explanatory view schematically showing another electrophotographic photosensitive member having a laminated photosensitive layer.

[Explanation of symbols]

 Reference Signs List 11 conductive support 15 single-layer photosensitive layer 17 charge generation layer 19 charge transport layer

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI G03G 5/06 315 G03G 5/06 315C 316 316A 316B 319 319 322 322 324 324 324 324B 1-3-6 Magome, Ricoh Co., Ltd.

Claims (33)

[Claims] 1. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (2) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Chemical formula 2] (Wherein R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group;
₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. n represents 0 or 1. ) 2. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (3) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 4] [Wherein, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group or a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, wherein the substituent is a di-lower alkylamino group; , A lower alkyl group, a lower alkoxy group, a halogen atom, an aralkylamino group and an amino group.). ] 3. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (4) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 6] (In the formula, R ₁ , R ₂ , and R ₃ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenoxy group, or a halogen atom.) 4. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (5) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image [In the formula, R ₁ represents a hydrogen atom, a halogen atom, a cyano group, or a lower alkyl group, and Ar represents the following general formula (a) or (b): (However, R ₂ , R ₃ and R ₆ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted benzyl group, and R ₄ and R ₅ represent a hydrogen atom, a halogen atom, a lower alkyl group, Represents a lower alkoxy group or a di-lower alkylamino group). ] 5. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (6) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein R ₁ , R ₂ , R ₃ , R ₄ and R ₆ represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted di-lower alkylamino group or a dibenzylamino group. , R ₅ represents a lower alkyl group or a benzyl group.) 6. An electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (7) on a conductive support. body. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 13] (In the formula, Ar represents a naphthalene ring, an anthracene ring, a pyrene ring, a styryl group or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents a lower alkyl group or a benzyl group.) 7. An electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (8) on a conductive support. body. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein, R ₁ represents a lower alkyl group, a 2-hydroxyethyl group or a 2-chloroethyl group, R ₂ represents a lower alkyl group, a benzyl group or a phenyl group, and R ₃ represents a hydrogen atom, a halogen atom, a lower alkyl group. Group, lower alkoxy group, di-lower alkylamino group or nitro group.) 8. An electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (9) on a conductive support. body. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 17] (Wherein, R ₁ represents a hydrogen atom, a lower alkyl group, a chloroethyl group or a hydroxyethyl group, R ₂ represents a hydrogen atom or a halogen atom, and R ₃ represents a lower alkyl group, a di-lower alkylamino group, a diarylamino group. Represents a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue, or a substituted or unsubstituted heterocyclic residue.) 9. An electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (10) on a conductive support. body. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein, R ₁ represents a lower alkyl group, R ₂ represents a lower alkyl group, a di-lower alkylamino group, a diarylamino group,
Represents a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue, or a substituted or unsubstituted heterocyclic residue. ) 10. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (11) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein R ₁ and R ₂ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group, a chloro lower alkyl group, an alkyl group having 1 to 2 carbon atoms, an alkyl group having 1 to 2 carbon atoms) Represents 5 to 6 cycloalkyl groups or substituted or unsubstituted aralkyl groups.) 11. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (12) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 23] (Wherein R ₁ , R ₃ and R ₄ are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom or a substituted or unsubstituted R ₂ represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, provided that R ₁ ,
R ₂ , R ₃ and R ₄ are not all hydrogen atoms. Further, k, l, m and n are integers of ₁ , ₂ , 3 or 4, and when each is an integer of 2, 3 or 4, R ₁ , R ₂ ,
R ₃ and R ₄ may be the same or different. ) 12. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (13) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image A-CH ₂ CH ₂ —Ar ₁ —CH ₂ CH ₂ —A (13) wherein Ar ₁ is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group A represents a substituted or unsubstituted N-substituted carbazolyl group or the following general formula (c): (However, Ar ₂ is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, and R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ). ] 13. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (14) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 28] (Wherein R ₁ is a hydrogen atom, an alkyl group, an alkoxy group,
Represents an aryloxy group, a dialkylamino group, a diarylamino group or a halogen atom, R ₂ and R ₃ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and Ar represents an aromatic hydrocarbon group or a heterocyclic group. Represents a ring group. n represents an integer of 1 or 2. ) 14. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (15) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Chemical Formula 30] (Wherein R ₁ and R ₂ are a hydrogen atom, an amino group, a substituted or unsubstituted dialkylamino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted R ₃ and R ₄ represent a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and Ar represents a substituted or unsubstituted monocyclic aromatic hydrocarbon group, a substituted or unsubstituted group. Represents a substituted non-fused polycyclic aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group.) 15. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (16) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image Wherein A is an N-substituted carbazolyl group or the following general formula (d): (However, Ar is an aromatic hydrocarbon group or a heterocyclic group,
R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ), And R represents an alkyl group, an alkoxy group, or a halogen atom. n represents an integer of 0 to 4, and when n is 2 or more, Rs may be the same or different. ] 16. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (17) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) ] Wherein A is a 9-anthryl group, a substituted or unsubstituted N-substituted carbazolyl group, an N-substituted phenothiazinyl group, or a compound represented by the following general formula (e): (However, Ar represents a substituted or unsubstituted arylene group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.) And R represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. m represents an integer of 2 to 8, and n represents an integer of 0 or 1. ] 17. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (18) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image [In the formula, A is a 9-anthryl group, a substituted or unsubstituted N-substituted carbazolyl group, an N-substituted phenothiazinyl group, or a compound represented by the following general formula (f): (However, Ar represents a substituted or unsubstituted arylene group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.) And R represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. n represents the integer of 0-8. ] 18. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (19) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 41] (In the formula, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different.) 19. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (20) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and at least one of R ₁ and R ₂ represents a substituted or unsubstituted aryl group.) 20. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (21) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 45] (Wherein, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₁ and R ₂ may be the same or different. R ₃ and R ₄ are hydrogen atoms , An alkyl group, an alkoxy group or a halogen atom, m represents an integer of 1, 2, or 3, n represents an integer of 1, 2, 3, or 4. When m or n is 2 or more, R ₃ , R ₄ may be the same or different.) 21. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (22) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 47] (In the formula, m represents an integer of 0 or 1, and when m is 1, X
An oxygen atom, a sulfur _{atom, -CH 2 -, - CH 2} CH 2 -,
Represents -CH = CH- or -N (R)-(where R represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group). R ₁ and R ₂ represent an alkyl group, an aralkyl group, a carbocyclic aromatic group or a heterocyclic group, and R ₃ and R ₄ represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom 22. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (23) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, Ar represents a substituted or unsubstituted biphenylene group, and R ₁ , R _2, and R ₃ represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group, an alkoxy group, or an aryl group. Represents an oxy group, an alkylmercapto group, a methylenedioxy group, a methylenedithio group, or an aryl group, and R ₁ , R ₂ and R ₃ may be the same or different, and l, m and n are integers of 1 to 5 Represents each of 2 to
When it is an integer of 5, R ₁ , R ₂ and R ₃ may be the same or different. ) 23. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (24) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, Ar represents a phenylene group or a biphenylene group, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and n represents an integer of 1 to 4.) 24. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (25) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, A ₁ and A ₂ each represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different. Ar represents a substituted or unsubstituted fused polycyclic hydrocarbon. Represents a group.) 25. An electrophotographic method comprising: providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (26) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 55] (Wherein R ₁ and R ₂ are a substituted or unsubstituted alkyl group,
Represents a substituted or unsubstituted aryl group, wherein n is 1 or 2
Represents an integer. R ₃ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group,
R ₄ and R ₅ represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a substituted or unsubstituted alkyl group, or a halogen atom. m represents an integer of 1, 2, and 3, and 1 represents an integer of 1, 2, 3, and 4. l, m
Is an integer of 2 or more, R ₄ and R ₅ may be the same or different. ) 26. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (27) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 57] (Wherein, R ₁ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R ₂ , R ₃ , and R ₄ represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group , A methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, a substituted or unsubstituted aryl group, h represents an integer of 1, 2, 3, and 4, and k and l represent 1, 2, 3 Represents an integer of 4, 5;
When h, k, and l are integers of 2 or more, R ₂ , R ₃ , and R ₄ may be the same or different. n represents an integer of 1, 2, 3, and 4, and m represents an integer of 4-n. When m is 2 or more, R
₁ may be the same or different. ) 27. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (28) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, A ₁ represents a substituted or unsubstituted aromatic hydrocarbon group, A ₂ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and A ₃ represents a hydrogen atom, a substituted or unsubstituted group. Represents a substituted alkyl group or a substituted or unsubstituted aryl group, m and n represent an integer of 1 or 2, and m + n is 3, provided that m or n is 2
At this time, A ₁ , A ₃ or A ₂ may be the same or different. ) 28. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (29) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different, except for a 1,6-diaminopyrene compound. ) 29. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (30) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) [Formula 63] (In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) 30. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (31) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein, R represents a lower alkyl group or a benzyl group;
Represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, or an amino group substituted with a lower alkyl group or a benzyl group. n represents an integer of 1 or 2. ) 31. An electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the following general formula (1) and a compound represented by the following general formula (32) on a conductive support. Photoconductor. Embedded image Wherein, R ₁ represents a hydrogen atom or a halogen atom, R ₂
Is a substituted or unsubstituted aromatic or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, a lower alkoxy group And a nitro group.) Embedded image (Wherein, R ₁ and R ₂ represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a substituted or unsubstituted alkyl group, and R ₃ and R ₄ represent a hydrogen atom, a cyano group, an alkoxycarbonyl group, It represents an unsubstituted alkyl group, R ₅
Represents a hydrogen atom, a lower alkyl group or an alkoxy group.
W represents a hydrogen atom or a substituted or unsubstituted alkyl group. j is an integer of 1 to 5, k is an integer of 1 to 4, l is 0 to 2
M represents an integer of 1 or 2, and n represents an integer of 1 to 3. ) 32. A photosensitive layer comprising at least a charge transport layer and a charge generation layer containing a charge generation material as a main component, wherein the charge transport layer comprises at least a compound represented by the general formula (1) and a compound represented by the general formulas (2) to (2). 32. The electrophotographic photosensitive member according to claim 1, further comprising one of the compounds represented by (32). 33. A photosensitive layer comprising a single-layer photosensitive layer containing at least a charge generating material and a compound represented by the general formula (1) and one of the compounds represented by the general formulas (2) to (32). The electrophotographic photosensitive member according to any one of claims 1 to 31, wherein [0001]