JPH10213915A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an electrophotographic photoreceptor improving the film quality, having superior stability even after repeated use, preventing the occurrence of an abnormal image due to the deterioration of the photosensitive layer and maintaining high sensitivity by forming a photosensitive layer contg. two kinds of specified compds. on an electrically conductive substrate. SOLUTION: A photosensitive layer contg. a compd. represented by formula I and a compd. represented by formula II is formed on an electrically conductive substrate to obtain the objective electrophotographic photoreceptor improving the film quality, having superior stability even after repeated use, preventing the occurrence of an abnormal image due to the deterioration of the photosensitive layer and maintaining high sensitivity. In the formula I, each of R1 and R3 is H, lower alkly, di-lower alkylamino, etc., R2 is H, lower alkyl, halogen, etc., and (n) is 0 or 1. In the formula II, R is carbazolyl, pyridyl, thienyl, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor using a combination of specific charge transport materials and having excellent photosensitivity, printing characteristics and repetitive use characteristics.

[0002]

2. Description of the Related Art In an organic electrophotographic photosensitive member, a function-separated type photosensitive member in which a charge generation layer and a charge transport layer are laminated in order to enhance the sensitivity has attracted attention and has been put to practical use. The mechanism of electrostatic latent image formation in this function-separated type photoreceptor is as follows. When the photoreceptor is charged and irradiated with light, the light is absorbed by the charge generation layer, and the charge generation layer that absorbed the light generates charge carriers. The charge carriers are injected into the charge transport layer, move in the charge transport layer (or the photosensitive layer) according to the electric field generated by the charge, and form an electrostatic latent image by neutralizing the charge on the surface of the photoreceptor. Is what you do.

[0003]

Various photoreceptor materials have been developed in the past, but in order to produce an excellent electrophotographic photoreceptor which can be practically used, sensitivity, receptive potential, potential holding property, and potential Various characteristics are required, such as stability, residual potential, electrophotographic characteristics represented by spectral characteristics, mechanical durability such as abrasion resistance, and chemical stability against heat, light, and discharge products. In particular, it is important to have high sensitivity and excellent repetition stability, but as described above, some high sensitivity characteristics can be achieved by a suitable combination of a charge generation material and a charge transport material. is there.

On the other hand, studies have also been made on combining mechanical durability with the above. However, depending on the combination of a charge generation material and a charge transport material conventionally proposed, all of the above conditions are satisfied. Things were not obtained. Accordingly, there has been a strong demand for an electrophotographic photoreceptor that maintains high sensitivity and is excellent in stability by repeated use using a charge generation material and a charge transport material that have been conventionally proposed.

An object of the present invention is to improve the film quality of a photoreceptor and to prevent the occurrence of abnormal images due to the deterioration of the photosensitive layer film, thereby exhibiting excellent stability even after repeated use and maintaining high sensitivity. It is an object of the present invention to provide an electrophotographic photoreceptor capable of performing the following.

[0006]

According to the present invention, first, at least a compound represented by the following general formula (1) and a compound represented by the following general formula (2) are contained on a conductive support. An electrophotographic photoreceptor comprising a photosensitive layer is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group or an anthryl group (provided that 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). Secondly, an electrophotographic photoreceptor comprising a conductive support and a photosensitive layer containing at least the compound represented by the general formula (1) and the compound represented by the following general formula (3) provided on the conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

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. Third, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (4) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ is a hydrogen atom, a halogen atom, a cyano group or a lower alkyl group, and Ar is

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 , A lower alkoxy group or a di-lower alkylamino group.). Fourth, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (5) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ is a hydrogen atom, a lower alkyl group, a chloroethyl group or a hydroxyethyl group, R ₂ is a hydrogen atom or a halogen atom, and R ₃ is a lower alkyl group, a di-lower alkylamino group, a diarylamino group. Substituted or unsubstituted styryl group, substituted or unsubstituted aromatic ring residue (aromatic ring is benzene ring, naphthalene ring or anthracene ring) or substituted or unsubstituted heterocyclic residue (heterocycle is pyridine ring, quinoxaline ring Or a carbazole ring). Fifth, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (6) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ is a lower alkyl group, R ₂ is a lower alkyl group, a di-lower alkylamino group, a diarylamino group, a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue (where the aromatic ring is A benzene ring, a naphthalene ring or an anthracene ring) or a substituted or unsubstituted heterocyclic residue (a heterocyclic ring is a pyridine ring, a quinoxaline ring or a carbazole ring). Sixth, an electrophotographic photoreceptor comprising a conductive support and a photosensitive layer containing at least the compound represented by the general formula (1) and the compound represented by the following general formula (7). Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ and R ₂ may be the same or different, and represent a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group, a chloro lower alkyl group, an alkyl acyl group having 1 to 2 carbon atoms, and an alkyl carbon number. 5 to 6 cycloalkyl groups or substituted or unsubstituted aralkyl groups. Seventh, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (8) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ , 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, or a substituted or unsubstituted An aryl group of
R ₂ represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. However,
Except when R ₁ , R ₂ , R ₃ and R ₄ are all hydrogen atoms. K, l, m and n are 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.
Eighth, at least the above general formula (1) is formed on the conductive support.
And an electrophotographic photosensitive member comprising a photosensitive layer containing a compound represented by the following general formula (9) and a compound represented by the following general formula (9).

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, Ar ₁ represents a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and A represents a substituted or unsubstituted N-
Substituted carbazolyl group or

Embedded image (However, Ar ₂ represents a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) . Ninth, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (10) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ is a hydrogen atom, an alkyl group, an alkoxy group,
An aryloxy group, a dialkylamino group, a diarylamino group or a halogen atom, R ₂ and R ₃ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and Ar is an aromatic hydrocarbon group or a heterocyclic group To n
Represents an integer of 1 or 2. Tenth, an electrophotographic photoreceptor comprising a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (11) on a conductive support. Is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ and R ₂ represent 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 In the substituted aryl group, R ₃ and R ₄ represent a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. Ar represents a substituted or unsubstituted monocyclic aromatic hydrocarbon group, a substituted or unsubstituted non-fused polycyclic aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic group. Eleventh, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (12) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image Wherein A is an N-substituted carbazolyl group or

Embedded image (Where Ar is an aromatic hydrocarbon group or a heterocyclic group, and R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group),
R is any one of an alkyl group, an alkoxy group and a halogen atom, n is an integer of 0 to 4, and when n ≧ 2, R may be the same or different. Twelfth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (13) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, A is a 9-anthryl group, substituted or unsubstituted N
A substituted carbazolyl group, a substituted or unsubstituted N-substituted phenothiazinyl group or

Embedded image (In the formula, Ar represents a substituted or unsubstituted arylene group; R ₁ and R ₂ represent a substituted or unsubstituted alkyl group;
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. Represent. m represents an integer of 2 to 8, and n represents an integer of 0 or 1. Thirteenth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (14) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, A is a 9-anthryl group, substituted or unsubstituted N
A substituted carbazolyl group, a substituted or unsubstituted N-substituted phenothiazinyl group or

Embedded image (In the formula, Ar represents a substituted or unsubstituted arylene group; R ₁ and R ₂ represent a substituted or unsubstituted alkyl group;
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. Represent. n represents the integer of 0-8. Fourteenth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (15) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different. Fifteenth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (16) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image (In the formula, R ₁ and R ₂ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, R ₁
And at least one of R ₂ represents a substituted or unsubstituted aryl group. Sixteenth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (17) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image (Wherein R ₁ and R ₂ are a substituted or unsubstituted alkyl group,
Represents a substituted or unsubstituted aryl group, R ₁ and R ₂
May be the same or different. R ₃ and R ₄ are hydrogen atoms,
Represents an alkyl group, an alkoxy group or a halogen atom,
Further, m is an integer of 1, 2, 3 and n is an integer of 1, 2, ₃ , _{4. When} m and n are respectively plural, R ₃ and R ₄ may be the same or different. Seventeenth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (18) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, m is an integer of 0 or 1, and when m = 1, X
Is an oxygen atom, a sulfur atom,

Embedded image Wherein R ₁ and R ₂ are an alkyl group, an aralkyl group,
Represents a carbocyclic aromatic group or a double-ring group. 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 double-ring group. n is an integer of 0 or 1. R ₃ may form a benzene ring together with X. Eighteenthly, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (19) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

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,
An alkyl group which may have a cyano group or a substituent, an alkoxy group, an aryloxy group, an alkyl mercapto group,
Represents a methylenedioxy group, a methylenedithio group or an aryl group, and R ₁ , R ₂ and R ₃ may be the same or different. L, m, and n each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₁ , R _2, and R ₃ may be the same or different. Nineteenthly, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (20) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, Ar represents a phenylene group or a biphenylene group;
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. Twentieth, an electrophotographic photosensitive method comprising providing a photosensitive layer containing at least a compound represented by the general formula (1) and a compound represented by the following general formula (21) on a conductive support. A body is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, A ₁ and A ₂ 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 group. Twenty-first, an electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (22) on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

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 n represents 1 or 2
Represents an integer. R ₃ represents a hydrogen atom, a substituted or unsubstituted alkyl group or 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 or 3, l represents an integer of 1, 2, 3 or 4, and R ₄ and R ₅ may be the same or different when m and l are integers of 2 or more. . Twenty-second, an electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (23) on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. n is 1, 2, 3
Or, represents an integer of 4, and m represents an integer of 4-n. When m is 2 or more, R ₁ may be the same or different. 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 or a substituted or unsubstituted aryl group. Represent. H is an integer of 1, 2, 3 or 4, k and l are 1,
Represents an integer of 2, 3, 4, or 5, and when h, k, and l are 2 or more, R ₂ , R ₃ , and R ₄ may be the same or different. Twenty-third, an electrophotographic method characterized in that a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (24) is provided on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

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 alkyl group. Represents a group or a substituted or unsubstituted aryl group. m and n are integers of 1 or 2, and m + n = 3. Where m or n is 2
In this case, A ₁ , A ₃ or A ₂ may be the same or different. Twenty-fourth, on a conductive support, at least a compound represented by the above general formula (1) and a compound represented by the following general formula (25)
An electrophotographic photosensitive member comprising a photosensitive layer containing a compound represented by the formula (1):

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, RI and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different. However, 1,6-diaminopyrene compounds are excluded. Twenty-fifth, an electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (26) on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Twenty-sixth, an electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (27) on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, R is a lower alkyl group or a pendyl group, X is 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 pendyl group; Is an integer of 1 or 2. Twenty-seventh, an electrophotographic method comprising providing a photosensitive layer containing at least a compound represented by the above general formula (1) and a compound represented by the following general formula (28) on a conductive support. A photoreceptor is provided.

Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1.

Embedded image In the formula, 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,
R ₃ and R ₄ represent a hydrogen atom, a cyano group, an alkoxycarbonyl group or a substituted or unsubstituted alkyl group, and R ₅ represents a hydrogen atom, a lower alkyl group or an alkoxy group. W is a hydrogen atom or a substituted or unsubstituted alkyl group, j is 1 to 5, k is 1 to 4, l is 0 to 2, m is 1 or 2, n
Represents an integer of 1 to 3. Twenty-eighth, there is provided an electrophotographic photosensitive member characterized in that a charge generation layer mainly composed of a charge generation material and a small number of transport layers are laminated on a conductive support. 1. 1. Compound represented by general formula (1) and compound represented by general formula (2) 2. Compound represented by general formula (1) and compound represented by general formula (3) 3. Compound represented by general formula (1) and compound represented by general formula (4) 4. Compound represented by general formula (1) and compound represented by general formula (5) 5. Compound represented by general formula (1) and compound represented by general formula (6) 6. Compound represented by general formula (1) and compound represented by general formula (7) 7. Compound represented by general formula (1) and compound represented by general formula (8) 8. Compound represented by general formula (1) and compound represented by general formula (9) 9. Compound represented by general formula (1) and compound represented by general formula (10) Compound represented by general formula (1) and general formula (11)
10. The compound represented by Compound represented by general formula (1) and general formula (12)
12. A compound represented by the formula Compound represented by general formula (1) and general formula (13)
12. A compound represented by the formula: Compound represented by general formula (1) and general formula (14)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (15)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (16)
15. A compound represented by the formula: Compound represented by general formula (1) and general formula (17)
17. A compound represented by the formula: Compound represented by general formula (1) and general formula (18)
18. A compound represented by the formula: Compound represented by general formula (1) and general formula (19)
19. A compound represented by the formula: Compound represented by general formula (1) and general formula (20)
20. A compound represented by the formula: Compound represented by general formula (1) and general formula (21)
21. Compound represented by Compound represented by general formula (1) and general formula (22)
22. A compound represented by the formula: Compound represented by general formula (1) and general formula (23)
23. Compound represented by Compound represented by general formula (1) and general formula (24)
24. A compound represented by the formula: Compound represented by general formula (1) and general formula (25)
25. A compound represented by the formula: The compound represented by the general formula (1) and the general formula (26)
26. Compound represented by Compound represented by general formula (1) and general formula (27)
Compound represented by the following formula: 27. Compound represented by general formula (1) and general formula (28)
A compound represented by the formula (29), a single-layer photosensitive layer containing at least a set selected from the group consisting of a compound represented by the following 1 to 27 and a charge generating material on a conductive support An electrophotographic photosensitive member is provided. 1. 1. Compound represented by general formula (1) and compound represented by general formula (2) 2. Compound represented by general formula (1) and compound represented by general formula (3) 3. Compound represented by general formula (1) and compound represented by general formula (4) 4. Compound represented by general formula (1) and compound represented by general formula (5) 5. Compound represented by general formula (1) and compound represented by general formula (6) 6. Compound represented by general formula (1) and compound represented by general formula (7) 7. Compound represented by general formula (1) and compound represented by general formula (8) 8. Compound represented by general formula (1) and compound represented by general formula (9) 9. Compound represented by general formula (1) and compound represented by general formula (10) Compound represented by general formula (1) and general formula (11)
10. The compound represented by Compound represented by general formula (1) and general formula (12)
12. A compound represented by the formula Compound represented by general formula (1) and general formula (13)
12. A compound represented by the formula: Compound represented by general formula (1) and general formula (14)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (15)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (16)
15. A compound represented by the formula: Compound represented by general formula (1) and general formula (17)
17. A compound represented by the formula: Compound represented by general formula (1) and general formula (18)
18. A compound represented by the formula: Compound represented by general formula (1) and general formula (19)
19. A compound represented by the formula: Compound represented by general formula (1) and general formula (20)
20. A compound represented by the formula: Compound represented by general formula (1) and general formula (21)
21. Compound represented by Compound represented by general formula (1) and general formula (22)
22. A compound represented by the formula: Compound represented by general formula (1) and general formula (23)
23. Compound represented by Compound represented by general formula (1) and general formula (24)
24. A compound represented by the formula: Compound represented by general formula (1) and general formula (25)
25. A compound represented by the formula: The compound represented by the general formula (1) and the general formula (26)
26. Compound represented by Compound represented by general formula (1) and general formula (27)
Compound represented by the following formula: 27. Compound represented by general formula (1) and general formula (28)
Compound represented by

Hereinafter, the present invention will be described in detail. As a result of repeated studies on the above problems, the inventors of the present invention have found that the use of the above-described specific combination of charge transport materials in the photosensitive layer suppresses the occurrence of image quality defects even after repeated use, and also provides excellent electrophotographic characteristics. The present inventors have found that an electrophotographic photoreceptor having the following characteristics can be obtained, leading to the present invention.

The electrophotographic photosensitive member of the present invention will be described with reference to the drawings. FIG. 1 is a cross-sectional view showing a single-layer photosensitive member of the present invention, in which a photosensitive layer 15 is provided on a conductive support 11. Have been. FIG. 2 and FIG. 3 are cross-sectional views showing a configuration example of the laminated photoreceptor according to the present invention, in which a charge generation layer 17 mainly composed of a charge generation material, a charge transport layer 19 mainly composed of a charge transport material, and Has a stacked configuration.
In such a single-layer or laminated photoreceptor, a charge transport material comprising the compound represented by the general formula (1) and at least one selected from the compounds represented by the general formulas (2) to (28) is used. Used in combination.

[0009]

Embodiments of the present invention will be described below. The conductive support 11 has a volume resistance of 10 ¹⁰ Ω.
cm or less, for example, aluminum,
Metals such as nickel, chromium, nichrome, copper, silver, gold, platinum, and metal oxides such as tin oxide and indium oxide,
Film or cylindrical plastic or paper coated by vapor deposition or sputtering, or plates of aluminum, aluminum alloy, nickel, stainless steel, etc., and after making them into a tube, surface treatment by cutting, super finishing, polishing, etc. Pipes or the like can be used.

Next, the photosensitive layer 15 will be described. For convenience of explanation, the case where the charge generation layer 17 and the charge transport layer 19 are stacked will be described first. The charge generation layer 17 is a layer containing a charge generation material as a main component. Inorganic and organic materials are used as the charge generating material, and representative examples thereof include monoazo pigments, disazo pigments, trisazo pigments, perylene pigments, perinone pigments, quinacridone pigments, quinone condensed polycyclic compounds, and squaric acid dyes. Phthalocyanine pigments, naphthalocyanine pigments, azulhenium salt dyes, selenium, selenium-tellurium, selenium-arsenic alloys, amorphous silicon, and the like.

The charge generating materials may be used alone or as a mixture of two or more. The charge generation layer 17 is dispersed with a suitable resin such as tetrahydrofuran, cyclohexanone, dioxane, 2-butanone, and dichloroethane by a ball mill, an attritor, a sand mill, or the like, together with a binder resin appropriately using a charge generation material. It can be formed by coating. The coating can be performed by a dip coating method, a spray coating method, a bead coating method, or the like.

[0012] As the binder resin used as appropriate,
Polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate, silicone resin,
Acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polyacrylamide and the like are used. The amount of the binder resin appropriately used is 0 to 1 part by weight of the charge generation material.
~ 2 parts by weight is suitable.

The charge generation layer 17 can also be provided 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 preferably 0.1 to 2 μm.

The charge transport layer 19 can be formed by dissolving or dispersing a charge transport material and a binder resin in a suitable solvent, and applying and drying this. If necessary, a plasticizer or a leveling agent can be added.

The charge transport material is a mixture of the compound represented by the general formula (1) and at least one selected from the compounds represented by the general formulas (2) to (28). Specific examples of these compounds are shown in Tables 1 and 2 below.
05.

[0016]

[Table 1]

[0017]

[Table 2]

[0018]

[Table 3]

[0019]

[Table 4]

[0020]

[Table 5]

[0021]

[Table 6]

[0022]

[Table 7]

[0023]

[Table 8]

[0024]

[Table 9]

[0025]

[Table 10]

[0026]

[Table 11]

[0027]

[Table 12]

[0028]

[Table 13]

[0029]

[Table 14]

[0030]

[Table 15]

[0031]

[Table 16]

[0032]

[Table 17]

[0033]

[Table 18]

[0034]

[Table 19]

[0035]

[Table 20]

[0036]

[Table 21]

[0037]

[Table 22]

[0038]

[Table 23]

[0039]

[Table 24]

[0040]

[Table 25]

[0041]

[Table 26]

[0042]

[Table 27]

[0043]

[Table 28]

[0044]

[Table 29]

[0045]

[Table 30]

[0046]

[Table 31]

[0047]

[Table 32]

[0048]

[Table 33]

[0049]

[Table 34]

[0050]

[Table 35]

[0051]

[Table 36]

[0052]

[Table 37]

[0053]

[Table 38]

[0054]

[Table 39]

[0055]

[Table 40]

[0056]

[Table 41]

[0057]

[Table 42]

[0058]

[Table 43]

[0059]

[Table 44]

[0060]

[Table 45]

[0061]

[Table 46]

[0062]

[Table 47]

[0063]

[Table 48]

[0064]

[Table 49]

[0065]

[Table 50]

[0066]

[Table 51]

[0067]

[Table 52]

[0068]

[Table 53]

[0069]

[Table 54]

[0070]

[Table 55]

[0071]

[Table 56]

[0072]

[Table 57]

[0073]

[Table 58]

[0074]

[Table 59]

[0075]

[Table 60]

[0076]

[Table 61]

[0077]

[Table 62]

[0078]

[Table 63]

[0079]

[Table 64]

[0080]

[Table 65]

[0081]

[Table 66]

[0082]

[Table 67]

[0083]

[Table 68]

[0084]

[Table 69]

[0085]

[Table 70]

[0086]

[Table 71]

[0087]

[Table 72]

[0088]

[Table 73]

[0089]

[Table 74]

[0090]

[Table 75]

[0091]

[Table 76]

[0092]

[Table 77]

[0093]

[Table 78]

[0094]

[Table 79]

[0095]

[Table 80]

[0096]

[Table 81]

[0097]

[Table 82]

[0098]

[Table 83]

[0099]

[Table 84]

[0100]

[Table 85]

[0101]

[Table 86]

[0102]

[Table 87]

[0103]

[Table 88]

[0104]

[Table 89]

[0105]

[Table 90]

[0106]

[Table 91]

[0107]

[Table 92]

[0108]

[Table 93]

[0109]

[Table 94]

[0110]

[Table 95]

[0111]

[Table 96]

[0112]

[Table 97]

[0113]

[Table 98]

[0114]

[Table 99]

[0115]

[Table 100]

[0116]

[Table 101]

[0117]

[Table 102]

[0118]

[Table 103]

[0119]

[Table 104]

[0120]

[Table 105]

[0121]

[Table 106]

[0122]

[Table 107]

[0123]

[Table 108]

[0124]

[Table 109]

[0125]

[Table 110]

[0126]

[Table 111]

[0127]

[Table 112]

[0128]

[Table 113]

[0129]

[Table 114]

[0130]

[Table 115]

[0131]

[Table 116]

[0132]

[Table 117]

[0133]

[Table 118]

[0134]

[Table 119]

[0135]

[Table 120]

[0136]

[Table 121]

[0137]

[Table 122]

[0138]

[Table 123]

[0139]

[Table 124]

[0140]

[Table 125]

[0141]

[Table 126]

[0142]

[Table 127]

[0143]

[Table 128]

[0144]

[Table 129]

[0145]

[Table 130]

[0146]

[Table 131]

[0147]

[Table 132]

[0148]

[Table 133]

[0149]

[Table 134]

[0150]

[Table 135]

[0151]

[Table 136]

[0152]

[Table 137]

[0153]

[Table 138]

[0154]

[Table 139]

[0155]

[Table 140]

[0156]

[Table 141]

[0157]

[Table 142]

[0158]

[Table 143]

[0159]

[Table 144]

[0160]

[Table 145]

[0161]

[Table 146]

[0162]

[Table 147]

[0163]

[Table 148]

[0164]

[Table 149]

[0165]

[Table 150]

[0166]

[Table 151]

[0167]

[Table 152]

[0168]

[Table 153]

[0169]

[Table 154]

[0170]

[Table 155]

[0171]

[Table 156]

[0172]

[Table 157]

[0173]

[Table 158]

[0174]

[Table 159]

[0175]

[Table 160]

[0176]

[Table 161]

[0177]

[Table 162]

[0178]

[Table 163]

[0179]

[Table 164]

[0180]

[Table 165]

[0181]

[Table 166]

[0182]

[Table 167]

[0183]

[Table 168]

[0184]

[Table 169]

[0185]

[Table 170]

[0186]

[Table 171]

[0187]

[Table 172]

[0188]

[Table 173]

[0189]

[Table 174]

[0190]

[Table 175]

[0191]

[Table 176]

[0192]

[Table 177]

[0193]

[Table 178]

[0194]

[Table 179]

[0195]

[Table 180]

[0196]

[Table 181]

[0197]

[Table 182]

[0198]

[Table 183]

[0199]

[Table 184]

[0200]

[Table 185]

[0201]

[Table 186]

[0202]

[Table 187]

[0203]

[Table 188]

[0204]

[Table 189]

[0205]

[Table 190]

[0206]

[Table 191]

[0207]

[Table 192]

[0208]

[Table 193]

[0209]

[Table 194]

[0210]

[Table 195]

[0211]

[Table 196]

[0212]

[Table 197]

[0213]

[Table 198]

[0214]

[Table 199]

[0215]

[Table 200]

[0216]

[Table 201]

[0219]

[Table 202]

[0218]

[Table 203]

[0219]

[Table 204]

[0220]

[Table 205]

The mixing ratio of these compounds is such that the compound represented by the general formula (1) and at least one compound selected from the compounds represented by the general formulas (2) to (28) are 5:
Good results are obtained when the ratio is in the range of 95 to 95: 5.
The charge transporting material is used in an amount of 15 to 75% by weight, preferably 25 to 65% by weight, based on the total material of the charge transporting layer in the laminated photoreceptor.

Further, in addition to a charge transporting material comprising a compound represented by the general formula (1) and at least one selected from the compounds represented by the general formulas (2) to (28), a further known electron A transportable charge transporting material and / or a hole transporting charge transporting material may be used in combination.

Examples of the binder resin used in the charge transport layer 19 together with the charge transport material include polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, and polyvinyl chloride. , 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,
Thermoplastic or thermosetting resins such as acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenol resin, and alkyd resin can be used.

As the solvent, tetrahydrofuran, dioxane, toluene, 2-butanone, monochlorobenzene, dichloroethane, methylene chloride and the like are used.

The thickness of the charge transport layer 19 is 5 to 100 μm
Is appropriate.

In the present invention, a plasticizer or a leveling agent may be added to the charge transport layer 19. As a plasticizer,
Those used as plasticizers for general resins such as dibutyl phthalate and dioctyl phthalate can be used as they are.
A suitable amount is about weight%. As the leveling agent, silicone oils such as dimethyl silicone oil and methyl phenyl silicone oil, and polymers or oligomers having a perfluoroalkyl group in a side chain are used. % Is appropriate.

Next, the case where the photosensitive layer has a single-layer structure (FIG. 1) will be described. Many of the materials used in this case are the same as those used in the function separation type comprising a charge generation material and a charge transport material.

That is, a charge transporting material comprising at least a charge generating material and a compound represented by the general formula (1) and at least one compound selected from the compounds represented by the general formulas (2) to (28) is added to a binder. It can be formed by dissolving or dispersing in a suitable solvent together with the resin, coating and drying. If necessary, a plasticizer or a leveling agent can be added. 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 mixed.

A eutectic complex formed from a pyrylium-based dye and bisphenol A-based polycarbonate has the general formula (1)
A photosensitive layer to which a charge transporting material comprising a compound represented by formula (1) and at least one compound selected from the compounds represented by formulas (2) to (28) is also usable.

Further, a charge transport material comprising a compound represented by the general formula (1) and at least one selected from the compounds represented by the general formulas (2) to (28) and a binder resin are used as main components. A single-layer photosensitive layer containing no charge-generating material as an active ingredient is also useful as a photosensitive member having sensitivity to blue light to ultraviolet light.

The mixing ratio of the above two specific charge transporting materials in the single-layer photosensitive layer was 5: 5 as in the case of the laminated photosensitive layer.
It is preferably in the range of 95 to 95: 5, and the amount used is 5 to 75% by weight, preferably 10 to 65% by weight, based on all the constituent materials of the single-layer photosensitive layer. The thickness of the single-layer photosensitive layer is suitably from 5 to 100 μm.

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.

The undercoat layer may be added with a fine powder of a metal oxide exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide or the like in order to prevent moire and reduce residual potential. Good. These undercoat layers can be formed using an appropriate solvent and a coating method as in the above-described photosensitive layer.

Further, as the undercoat layer of the present invention, a metal oxide layer formed by, for example, 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 to the above, the undercoat layer of the present invention contains Al ₂ O ₃
Provided by anodic oxidation, organic substances such as polyparaxylylene (parylene), SiO, SnO ₂ , TiO ₂ , I
An inorganic substance such as TO or CeO ₂ provided by a vacuum thin film manufacturing method can also be used favorably. The thickness of the undercoat layer is 0 to 5 μm
Is appropriate.

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 are ABS resin, AC
S resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallyl sulfone, polybutylene, polybutylene terephthalate, polycarbonate, polyether sulfone, polyethylene, polyethylene terephthalate,
Polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide, polysulfone,
Examples of resins include AS resin, AB resin, BS resin, polyurethane, polyvinyl chloride, polyvinylidene chloride, and epoxy resin.

For the purpose of improving the abrasion resistance, a fluorine resin such as polytetrafluoroethylene, a silicone resin, and an inorganic material such as titanium oxide, tin oxide, and potassium titanate are dispersed in these resins. And the like 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.

In the present invention, another intermediate layer can be provided between the photosensitive layer and the protective layer. In the middle layer,
Generally, a binder resin is used as a main component. These resins include polyamide, alcohol-soluble nylon,
Water-soluble polyvinyl butyral, polyvinyl butyral,
Polyvinyl alcohol and the like. As a method for forming the intermediate layer, a normal coating method is employed as described above.
The thickness of the intermediate layer is suitably about 0.05 to 2 μm.

[0239]

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. First, when the compounds represented by the general formulas (1) and (2) are used in combination as the charge transporting material,
This will be described with reference to Examples 1 to 4 and Comparative Examples 1 to 4.

Example 1 An undercoating layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following compositions were sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to a thickness of 3 μm. An undercoat layer, a 0.2 μm charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention. [Coating solution for undercoat layer] 15 parts of oil-free alkyd resin (manufactured by Dainippon Ink and Chemicals, Inc .: Beckolite M6401) 10 parts melamine resin (manufactured by Dainippon Ink and Chemicals, Inc .: Super Beckamine G-821) 10 parts Titanium dioxide (Ishihara Sangyo) 50 parts 2-butanone 40 parts [Coating solution for charge generating layer] 5 parts of a charge generating material having the following structural formula

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 [Charge transport layer coating solution] Compound NO. Compound No. 2-5 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 1 An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 2-5 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 2 After the surface of an aluminum cylinder was anodized, a sealing treatment was performed. On top of this,
The following charge generation layer coating solution and charge transport layer coating solution are sequentially applied.
After drying, a charge generation layer of 0.2 μm and a charge transport layer of 20 μm were formed to prepare an electrophotographic photoreceptor of the present invention. [Charge Generating Layer Coating Solution] X-type metal-free phthalocyanine (manufactured by Dainippon Ink & Chemicals, Inc .: Fastgen Blue 8120B) 3 parts Polyvinyl butyral resin (manufactured by Sekisui Chemical Co., Ltd .: Eslec BL-S) 1 part Cyclohexanone 250 parts Tetrahydrofuran 50 Part [Coating solution for charge transport layer] Compound NO. Compound No. 2-22 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 2] The compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 2 except that the compound of No. 2-22 was not added.

Example 3 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 and dried on an aluminum cylinder to form a 2 μm undercoat layer. , A 0.2 μm charge generation layer and a 20 μm charge transport layer, to thereby prepare an electrophotographic photoreceptor of the present invention. [Coating solution for undercoat layer] Alcohol-soluble nylon (Toray: Amilan CM-8000) 10 parts Titanium dioxide (Ishihara Sangyo: Taipaque CR-EL) 40 parts Methanol 120 parts n-butanol 60 parts [Charge generating layer Coating liquid] 3 parts of charge generation material of the following structural formula

Embedded image Polyester (manufactured by Toyobo: Byron 200) 1 part Cyclohexanone 150 parts Cyclohexane 100 parts [Coating solution for charge transport layer] Compound NO. Compound No. 2-32 4 parts Compound NO. 1-8 compound 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 3 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 8-32 compound 8 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 4 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 26 μm.
To form an electrophotographic photoreceptor of the present invention. 3 parts of charge generation material of the following structural formula

Embedded image Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 21 parts Compound NO. Compound No. 2-5 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrafuran 200 parts

[Comparative Example 4] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 µm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 4 3 parts Polycarbonate (Panlite K-1300, manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 18 parts of the compound of 2-5 200 parts of tetrahydrofuran

The respective photoreceptors of Examples 1 to 4 and Comparative Examples 1 to 4 were subjected to the following measurements using an evaluation apparatus disclosed in Japanese Patent Application Laid-Open No. 60-100167. Potential Vm (V) after charging for 20 seconds at a corona discharge voltage of -6.0 kV (or +5.6 kV), and potential V after dark decay for 20 seconds
o (V), the residual potential VR (V) after 20 seconds of exposure with white light having an intensity of 6 lux, and the exposure amount E1 / 2 [lux · sec] required to attenuate the potential Vo to １ ／ were measured. . The potential holding ratio is defined as Vo / Vm. Each photoconductor was mounted on a Ricoh copier FT-3300 (or a photoconductor modified so that the photoconductor could be positively charged) and 30,000 copies were continuously made, and the presence or absence of an abnormal image was visually determined. After completion of the copying test, the characteristics of the photoconductors were measured by the same method as described above. The test results are shown in Table 206.

[0249]

[Table 206]

Next, the case where the compounds represented by the general formulas (1) and (3) are used in combination as the charge transporting material will be described with reference to Examples 5 to 8 and Comparative Examples 5 to 8.

Example 5 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 3-2 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 5 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 5, except that the coating solution for the charge transport layer in Example 5 had the following composition. [Coating solution for charge transport layer] Compound NO. 9 parts of compound of 3-2 Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts 75 parts of tetrahydrofuran

Example 6 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 3-7 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Methylene chloride 80 parts

[Comparative Example 6] In the coating liquid for the charge transport layer of Example 6, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 6, except that the compound of No. 3-7 was not added.

Example 7 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 3-18 4 parts Compound NO. Compound 1-8 4 parts Polycarbonate (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Comparative Example 7 An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 7, except that the coating solution for the charge transport layer in Example 7 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 3-18 compound 8 parts Polycarbonate (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 8 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23
A single-layer photosensitive layer having a thickness of μm was formed to prepare an electrophotographic photosensitive member of the present invention. [Coating solution for photosensitive layer] The same charge generation material as in Example 4 3 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 21 parts Compound NO. Compound No. 3-2 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

Comparative Example 8 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
An electrophotographic photoreceptor of Comparative Example was prepared by forming a single-layer photosensitive layer having a thickness of μm. [Coating solution for photosensitive layer] The same charge generation material as in Example 4 3 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 21 parts Compound NO. 18 parts of the compound of 3-2 200 parts of tetrahydrofuran

The above Examples 5 to 8 and Comparative Examples 5 to 8
The photoconductor characteristics of each photoconductor were measured in the same manner as described above.
The test results are shown in Table 207.

[0260]

[Table 207]

Next, the case where the compound represented by the general formula (1) and the compound represented by the general formula (4) are used in combination as the charge transporting material will be described with reference to Examples 9 to 12 and Comparative Examples 9 to 12.

Example 9 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 4-32 Compound 3 Compound No. 4-32 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 9 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 9 except that the coating liquid for the charge transport layer in Example 9 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 4-32 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 10 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 4-13 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 10] In the coating liquid for the charge transporting layer of Example 10, the compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 10 except that the compound of No. 4-13 was not added.

Example 11 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound 4 of compound NO4-37 4 parts of compound NO. 1-8 compound 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 11 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 11, except that the coating solution for the charge transport layer in Example 11 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 4-37 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 12 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 8 parts of the compound of No. 4-32 Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

Comparative Example 12 A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 4-32 compound 18 parts Tetrahydrofuran 200 parts

The above Examples 9 to 12 and Comparative Examples 9 to 12
Photoreceptor characteristics of each of the twelve photoreceptors were measured in the same manner as described above. The test results are shown in Table 208.

[0271]

[Table 208]

Next, Examples 13 to 16 and Comparative Example 13 were described for the case where the compound represented by the general formula (1) and the compound represented by the general formula (5) were used in combination as the charge transporting material.
This will be described with reference to FIGS.

Example 13 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 5-38 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 13 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 9 except that the coating liquid for the charge transport layer in Example 9 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 5-38 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 14 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 5-52 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 14] In the coating liquid for the charge transporting layer of Example 14, the compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 14 except that the compound of No. 5-52 was not added.

Example 15 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound 4 of Compound NO5-44 Compound NO. 1-8 compound 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 15 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 15 except that the coating liquid for the charge transport layer in Example 15 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 5-44 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 16 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 5-38 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

Comparative Example 16 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 5-38 compound 18 parts Tetrahydrofuran 200 parts

The above Examples 13 to 16 and Comparative Example 1
Photoconductor characteristics of each of the photoconductors 3 to 16 were measured in the same manner as described above. The test results are shown in Table 209.

[0282]

[Table 209]

Next, Examples 17 to 20 and Comparative Example 17 were carried out in the case where the compound represented by the general formula (1) and the compound represented by the general formula (6) were used in combination as the charge transporting material.
This will be described with reference to FIGS.

Example 17 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 6-24 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 17 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 17 except that the coating solution for the charge transport layer in Example 17 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 6-24 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 18 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 6-22 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 18] In the coating liquid for the charge transporting layer of Example 18, the compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 18 except that the compound of No. 6-22 was not added.

Example 19 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound 4 of Compound NO6-15 Compound NO. 1-8 compound 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 19 An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 19 except that the coating solution for the charge transport layer in Example 19 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 6-15 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 20 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 6-24 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 20] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 6-24 compound 18 parts Tetrahydrofuran 200 parts

The above Examples 17 to 20 and Comparative Example 1
Photoconductor characteristics of each of the photoconductors 7 to 20 were measured in the same manner as described above. The test results are shown in Table 210.

[0293]

[Table 210]

Next, Examples 21 to 24 and Comparative Example 21 were described for the case where the compound represented by the general formula (1) and the compound represented by the general formula (7) were used in combination as the charge transporting material.
To 24.

Example 21 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 7-6 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 21 An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 21, except that the coating liquid for the charge transport layer in Example 21 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 7-6 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 22 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 7-1 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 22] In the coating liquid for the charge transport layer of Example 22, the compound No. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 22 except that the compound of No. 7-1 was not added.

Example 23 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound 4 of compound NO7-8 Compound NO. 1-8 compound 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 23 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 23 except that the coating liquid for the charge transport layer in Example 23 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 7-8 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 24 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 7-6 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

Comparative Example 24 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 7-6 18 parts Tetrahydrofuran 200 parts

The above Examples 21 to 24 and Comparative Example 2
Photoconductor characteristics of each of the photoconductors 1 to 24 were measured in the same manner as described above. The test results are shown in Table 211.

[0304]

[Table 211]

Next, Examples 25 to 28 and Comparative Example 25 were applied to a case where the compound represented by the general formula (1) and the compound represented by the general formula (8) were used in combination as the charge transporting material.
To 28.

Example 25 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1, except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 8-60 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 25] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 25 except that the coating liquid for the charge transport layer in Example 25 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 8-60 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 26 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 8-36 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 26] In the coating solution for the charge transport layer of Example 26, compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 26 except that the compound of 8-36 was not added.

Example 27 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound 4 of compound NO8-21 Compound NO. 1-8 compound 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 27 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 27 except that the coating solution for the charge transport layer in Example 27 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 8-21 Compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 28 A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 8-60 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 28] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 8-60 18 parts Tetrahydrofuran 200 parts

The above Examples 25 to 28 and Comparative Example 2
Photoconductor characteristics of each of the photoconductors 5 to 28 were measured in the same manner as described above. The test results are shown in Table 212.

[0315]

[Table 212]

Next, Examples 29 to 32 and Comparative Example 29 are described for the case where the compound represented by the general formula (1) and the compound represented by the general formula (9) are used in combination as the charge transporting material.
To 32.

Example 29 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of No. 9-10 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 29 An electrophotographic photosensitive member of Comparative Example was produced in the same manner as in Example 29, except that the coating liquid for the charge transport layer in Example 29 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 9-10 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 30 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 9-11 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 30] In the coating liquid for the charge transporting layer of Example 30, the compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 30, except that the compound of No. 9-11 was not added.

Example 31 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Charge Transport Layer Coating Solution] Compound No. 9-23 Compound 4 parts Compound NO. 1-8 compound 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 31 An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 31, except that the coating liquid for the charge transport layer in Example 31 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 9-23 Compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 32 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 9-10 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

Comparative Example 32 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 9-10 18 parts Tetrahydrofuran 200 parts

In the above Examples 29 to 32 and Comparative Example 2,
Photoconductor characteristics of each of the photoconductors 9 to 32 were measured in the same manner as described above. The test results are shown in Table 213.

[0326]

[Table 213]

Next, Examples 33 to 36 and Comparative Example 3 were conducted in the case where the compound represented by the general formula (1) and the compound represented by the general formula (10) were used in combination as the charge transporting material.
This will be described with reference to 3 to 36.

Example 33 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1, except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 10-6 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 33 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 33 except that the coating liquid for the charge transport layer in Example 33 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 10-6 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 34 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 10-23 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 34] In the coating liquid for the charge transporting layer of Example 34, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 34 except that the compound of No. 10-23 was not added.

Example 35 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 10-19 4 parts Compound NO. 1-8 compound 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 35 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 35 except that the coating solution for the charge transport layer in Example 35 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 10-19 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 36 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 10-6 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 36] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 10-6 18 parts Tetrahydrofuran 200 parts

The above Examples 33 to 36 and Comparative Example 3
Photoconductor characteristics of each of the photoconductors Nos. 3 to 36 were measured in the same manner as described above. The test results are shown in Table 214.

[0337]

[Table 214]

Next, Examples 37 to 40 and Comparative Example 3 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (11) were used in combination as the charge transporting material.
This will be described with reference to 7 to 40.

Example 37 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 11-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 37 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 37, except that the coating solution for the charge transport layer in Example 37 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 11-1 Compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 38 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 11-7 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 38] In the coating liquid for the charge transporting layer of Example 38, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 38 except that the compound of No. 11-7 was not added.

Example 39 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 11-92 4 parts Compound NO. 1-8 compound 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 39 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 39, except that the coating solution for the charge transport layer in Example 39 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 11-92 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 40 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 11-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 40] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 11-1 18 parts Tetrahydrofuran 200 parts

The above Examples 37 to 40 and Comparative Example 3
Photoconductor characteristics of each of the photoconductors 7 to 40 were measured in the same manner as described above. The test results are shown in Table 215.

[0348]

[Table 215]

Next, Examples 41 to 44 and Comparative Example 4 were conducted in the case where the compound represented by the general formula (1) and the compound represented by the general formula (12) were used in combination as the charge transporting material.
This will be described with reference to 1 to 44.

Example 41 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 12-2 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 41] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 41, except that the coating solution for the charge transport layer in Example 41 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 12-2 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 42 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 12-82 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 42] In the coating liquid for the charge transport layer of Example 42, compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 42 except that the compound of No. 12-82 was not added.

Example 43 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 12-12 4 parts Compound NO. 1-8 compound 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 43] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 43, except that the coating solution for the charge transport layer in Example 43 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 12-12 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 44 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 12-2 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 44] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 12-2 18 parts Tetrahydrofuran 200 parts

The above Examples 41 to 44 and Comparative Example 4
Photoconductor characteristics of each of the photoconductors 1 to 44 were measured in the same manner as described above. The test results are shown in Table 216.

[0359]

[Table 216]

Next, Examples 45 to 48 and Comparative Example 4 were conducted in the case where the compound represented by the general formula (1) and the compound represented by the general formula (13) were used in combination as the charge transporting material.
This will be described with reference to 5 to 48.

Example 45 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 13-2 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 45 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 45, except that the coating liquid for the charge transport layer in Example 45 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 13-2 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 46 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compounds Nos. 13-19 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 46] In the coating solution for the charge transport layer of Example 46, compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 46 except that the compound of No. 13-19 was not added.

Example 47 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 13-52 4 parts Compound NO. 1-8 compound 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 47 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 47, except that the coating liquid for the charge transport layer in Example 47 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 13-52 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 48 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 13-2 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 48] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 13-2 Compound 18 parts Tetrahydrofuran 200 parts

The above Examples 45 to 48 and Comparative Example 4
Photoconductor characteristics of each of the photoconductors 5 to 48 were measured in the same manner as described above. The test results are shown in Table 217.

[0370]

[Table 217]

Next, Examples 49 to 52 and Comparative Example 4 were conducted in the case where the compound represented by the general formula (1) and the compound represented by the general formula (14) were used in combination as the charge transporting material.
This will be described with reference to 9 to 52.

Example 49 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 14-2 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 49] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 49, except that the coating liquid for the charge transport layer in Example 49 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 14-2 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 50 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 14-21 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 50] In the coating liquid for the charge transport layer of Example 50, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 50 except that the compound of No. 14-21 was not added.

Example 51 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 14-44 4 parts Compound NO. 1-8 compound 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 51] An electrophotographic photosensitive member of Comparative Example was produced in the same manner as in Example 51 except that the coating liquid for the charge transport layer in Example 51 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound 14-44 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 52 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 14-2 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 52] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 14-2 compound 18 parts tetrahydrofuran 200 parts

The above Examples 49 to 52 and Comparative Example 4
Photoconductor characteristics of each of the photoconductors 9 to 52 were measured in the same manner as described above. The test results are shown in Table 218.

[0381]

[Table 218]

Next, Examples 53 to 56 and Comparative Example 5 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (15) were used in combination as the charge transporting material.
This will be described with reference to 3 to 56.

Example 53 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 15-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 53 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 53, except that the coating liquid for the charge transport layer in Example 53 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 15-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 54 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 15-5 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 54] In the coating liquid for the charge transport layer of Example 54, compound NO. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 54 except that the compound of No. 15-5 was not added.

Example 55 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 15-9 4 parts Compound NO. 1-8 compound 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 55] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 55, except that the coating liquid for the charge transport layer in Example 55 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 15-9 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 56 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 15-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 56] A coating solution for a photosensitive layer having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 15-1 Compound 18 parts Tetrahydrofuran 200 parts

[0391] The above Examples 53 to 56 and Comparative Example 5
Photoconductor characteristics of each of the photoconductors 3 to 56 were measured in the same manner as described above. The test results are shown in Table 219.

[0392]

[Table 219]

Next, Examples 57 to 60 and Comparative Example 5 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (16) were used in combination as the charge transporting material.
This will be described with reference to 7 to 60.

Example 57 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 16-10 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 57] An electrophotographic photosensitive member of Comparative Example was produced in the same manner as in Example 57 except that the coating liquid for the charge transport layer in Example 57 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 16-10 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 58 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 16-7 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 58] In the coating liquid for the charge transporting layer of Example 58, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 58 except that the compound of No. 16-7 was not added.

Example 59 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 16-27 4 parts Compound No. 1-8 compound 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 59] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 59, except that the coating solution for the charge transport layer in Example 59 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 16-27 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Company: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 60 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 16-10 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 60] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 16-10 18 parts Tetrahydrofuran 200 parts

The above Examples 57 to 60 and Comparative Example 5
Photoconductor characteristics of each of the photoconductors 7 to 60 were measured in the same manner as described above. The test results are shown in Table 220.

[0403]

[Table 220]

Next, Examples 61 to 64 and Comparative Example 6 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (17) were used in combination as the charge transporting material.
This will be described with reference to 1 to 64.

Example 61 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 17-10 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 61] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 61 except that the coating liquid for the charge transport layer in Example 61 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 17-10 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 62 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 17-7 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 62] In the coating solution for the charge transport layer of Example 62, compound NO. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 62 except that the compound of No. 17-7 was not added.

Example 63 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 17-27 4 parts Compound NO. 1-8 compound 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 63 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 63, except that the coating liquid for the charge transport layer in Example 63 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 17-27 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Company: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 64 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 17-10 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 64] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 17-10 18 parts Tetrahydrofuran 200 parts

The above Examples 61 to 64 and Comparative Example 6
Photoconductor characteristics of each of the photoconductors 1 to 64 were measured in the same manner as described above. The test results are shown in Table 221.

[0414]

[Table 221]

Next, Examples 65 to 68 and Comparative Example 6 were described for the case where the compound represented by the general formula (1) and the compound represented by the general formula (18) were used in combination as the charge transporting material.
This will be described with reference to 5 to 68.

Example 65 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 18-11 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 65 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 65 except that the coating liquid for the charge transport layer in Example 65 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 18-11 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 66 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 18-4 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 66] In the coating liquid for the charge transport layer of Example 66, compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 66 except that the compound of No. 18-4 was not added.

Example 67 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 18-63 4 parts Compound NO. 1-8 compound 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 67 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 67, except that the coating solution for the charge transport layer in Example 67 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 18-63 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 68 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 18-11 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 68] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 18-11 compound 18 parts tetrahydrofuran 200 parts

The above Examples 65 to 68 and Comparative Example 6
Photoconductor characteristics of each of the photoconductors 5 to 68 were measured in the same manner as described above. The test results are shown in Table 222.

[0425]

[Table 222]

Next, Examples 69 to 72 and Comparative Example 6 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (19) were used in combination as the charge transporting material.
This will be described with reference to 9 to 72.

Example 69 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1, except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 19-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 69 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 69, except that the coating solution for the charge transport layer in Example 69 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 19-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 70 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 19-8 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 70] In the coating liquid for the charge transport layer of Example 70, the compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 70 except that the compound of No. 19-8 was not added.

Example 71 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 19-20 4 parts Compound NO. 1-8 compound 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 71] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 71 except that the coating solution for the charge transport layer in Example 71 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 19-20 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 72 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 19-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 72] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 19-1 18 parts Tetrahydrofuran 200 parts

The above Examples 69 to 72 and Comparative Example 6
Photoconductor characteristics of each of the photoconductors 9 to 72 were measured in the same manner as described above. The test results are shown in Table 223.

[0436]

[Table 223]

Next, Examples 73 to 76 and Comparative Example 7 were described for the case where the compound represented by the general formula (1) and the compound represented by the general formula (20) were used in combination as the charge transporting material.
This will be described with reference to 3 to 76.

Example 73 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 20-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 73 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 73 except that the coating liquid for the charge transport layer in Example 73 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 20-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 74 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 20-5 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 74] In the coating solution for the charge transport layer of Example 74, compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 74 except that the compound of No. 20-5 was not added.

Example 75 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 20-12 4 parts Compound NO. 1-8 compound 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 75 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 75, except that the coating liquid for the charge transport layer in Example 75 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 20-12 9 parts Polycarbonate resin (manufactured by Mitsubishi Gas Chemical Company: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 76 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 20-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 76] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge as in Example 4

The above Examples 73 to 76 and Comparative Example 7
Photoconductor characteristics of each of the photoconductors 3 to 76 were measured in the same manner as described above. The test results are shown in Table 224.

[0447]

[Table 224]

Next, Examples 77 to 80 and Comparative Example 7 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (21) were used in combination as the charge transporting material.
7 to 80.

Example 77 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 21-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 77 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 77, except that the coating solution for the charge transport layer in Example 77 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 21-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 78 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 21-19 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 78] The compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 78 except that the compound of No. 21-19 was not added.

Example 79 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 21-25 4 parts Compound NO. 1-8 compound 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 79] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 79, except that the coating liquid for the charge transport layer in Example 79 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 21-25 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 80 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 21-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 80] A coating liquid for a photosensitive layer having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 21-1 18 parts Tetrahydrofuran 200 parts

The above Examples 77 to 80 and Comparative Example 7
Photoconductor characteristics of each of the photoconductors 7 to 80 were measured in the same manner as described above. The test results are shown in Table 225.

[0458]

[Table 225]

Next, Examples 81 to 84 and Comparative Example 8 were applied to a case where the compound represented by the general formula (1) and the compound represented by the general formula (22) were used in combination as the charge transporting material.
This will be described with reference to 1 to 84.

Example 81 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 22-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 81] An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 81, except that the coating liquid for the charge transport layer in Example 81 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 22-1 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 82 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compounds Nos. 22-31 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 82] In the coating liquid for the charge transport layer of Example 82, compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 82 except that the compound of No. 22-31 was not added.

Example 83 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 3 except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 22-8 4 parts Compound NO. 1-8 compound 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 83 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 83 except that the coating liquid for the charge transport layer in Example 83 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 22-8 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 84 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 22-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 84] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 22-1 18 parts Tetrahydrofuran 200 parts

The above Examples 81 to 84 and Comparative Example 8
Photoconductor characteristics of each of the photoconductors 1 to 84 were measured in the same manner as described above. The test results are shown in Table 226.

[0469]

[Table 226]

Next, Examples 85 to 88 and Comparative Example 8 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (23) were used in combination as the charge transporting material.
This will be described with reference to 5 to 88.

Example 85 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1, except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 23-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 85 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 85, except that the coating liquid for the charge transport layer in Example 85 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 23-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 86 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 23-50 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 86] In the coating liquid for the charge transport layer of Example 86, Compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 86 except that the compound of No. 23-50 was not added.

Example 87 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 23-8 4 parts Compound NO. 1-8 compound 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 87] An electrophotographic photosensitive member of Comparative Example was produced in the same manner as in Example 87 except that the coating liquid for the charge transport layer in Example 87 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 23-8 compound 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 88 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 23-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 88] A coating solution for a photosensitive layer having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 23-1 18 parts Tetrahydrofuran 200 parts

[0479] The above Examples 85 to 88 and Comparative Example 8
Photoconductor characteristics of each of the photoconductors 5 to 88 were measured in the same manner as described above. The test results are shown in Table 227.

[0480]

[Table 227]

Next, Examples 89 to 92 and Comparative Example 8 were applied to the case where the compound represented by the general formula (1) and the compound represented by the general formula (24) were used in combination as the charge transporting material.
This will be described with reference to 9 to 92.

Example 89 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1, except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 24-8 3 parts Compound No. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

[Comparative Example 89] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 89 except that the coating liquid for the charge transport layer in Example 89 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 24-8 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 90 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compounds Nos. 24-15 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 90] In the coating solution for the charge transport layer of Example 90, compound No. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 90 except that the compound of No. 24-15 was not added.

Example 91 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 24-17 4 parts Compound No. 1-8 compound 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 91] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 91 except that the coating liquid for the charge transport layer in Example 91 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 24-17 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 92 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 24-8 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 92] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. 24-8 compound 18 parts tetrahydrofuran 200 parts

The above Examples 89 to 92 and Comparative Example 8
Photoconductor characteristics of each of the photoconductors 9 to 92 were measured in the same manner as described above. The test results are shown in Table 228.

[0490]

[Table 228]

Next, Examples 93 to 96 and Comparative Example 9 were conducted when the compound represented by the general formula (1) and the compound represented by the general formula (25) were used in combination as the charge transporting material.
This will be described with reference to 3 to 96.

Example 93 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 25-6 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 93 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 93, except that the coating liquid for the charge transport layer in Example 93 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. 25-6 compound 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 94 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 25-2 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 94] In the coating liquid for the charge transport layer of Example 94, compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 94 except that the compound of No. 25-2 was not added.

Example 95 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 25-16 4 parts Compound NO. 1-8 compound 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 95] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 95 except that the coating liquid for the charge transport layer in Example 95 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 25-16 9 parts Polycarbonate resin (manufactured by Mitsubishi Gas Chemical Company: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 96 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 25-6 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 96] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to a thickness of 23 μm.
To form an electrophotographic photoreceptor of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 25-6 18 parts Tetrahydrofuran 200 parts

The above Examples 93 to 96 and Comparative Example 9
Photoconductor characteristics of each of the photoconductors 3 to 96 were measured in the same manner as described above. The test results are shown in Table 229.

[0502]

[Table 229]

Next, the case where the compound represented by the general formula (1) and the compound represented by the general formula (26) are used in combination as the charge transporting material will be described with reference to Examples 97 to 100 and Comparative Examples 97 to 100.

Example 97 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 26-6 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 97 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 97, except that the coating liquid for the charge transport layer in Example 97 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 26-6 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 98 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 26-15 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 98] In the charge transport layer coating solution of Example 98, Compound No. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 98 except that the compound of No. 26-15 was not added.

Example 99 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 3, except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 26-21 4 parts Compound NO. 1-8 compound 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 99] An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 99, except that the coating liquid for the charge transport layer in Example 99 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound of 26-21 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

Example 100 A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
A single-layer photosensitive layer having a thickness of μ was formed to prepare an electrophotographic photosensitive member of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 26-6 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 100] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
A single-layer photosensitive layer was formed to prepare an electrophotographic photosensitive member of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 26-6 18 parts Tetrahydrofuran 200 parts

The photoreceptor characteristics of each of the photoreceptors of Examples 97 to 100 and Comparative Examples 97 to 100 were measured in the same manner as described above. The test results are shown in Table 230.

[0513]

[Table 230]

Next, the case where the compound represented by the general formula (1) and the compound represented by the general formula (27) are used in combination as the charge transporting material will be described with reference to Examples 101 to 104 and Comparative Examples 101 to 104.

Example 101 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 27-70 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 101 Example 101 was repeated except that the coating liquid for the charge transport layer in Example 101 was changed to one having the following composition.
In the same manner as in the above, an electrophotographic photosensitive member of a comparative example was produced. [Coating solution for charge transport layer] Compound NO. Compound 27-70 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 102 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2 except that the coating liquid for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compounds Nos. 27-92 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 102] In the coating liquid for the charge transport layer of Example 102, the compound NO. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 102 except that the compound of Nos. 27-92 was not added.

Example 103 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 3, except that the coating solution for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 27-192 4 parts Compound NO. 1-8 compound 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 103 Example 103 was repeated except that the coating liquid for the charge transport layer in Example 103 was changed to the one having the following composition.
In the same manner as in the above, an electrophotographic photosensitive member of a comparative example was produced. [Coating solution for charge transport layer] Compound NO. Compound 27-192 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

[Example 104] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
A single-layer photosensitive layer having a thickness of μ was formed to prepare an electrophotographic photosensitive member of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 27-70 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 104] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
A single-layer photosensitive layer was formed to prepare an electrophotographic photosensitive member of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 27-70 18 parts Tetrahydrofuran 200 parts

The photoreceptor characteristics of each of the photoreceptors of Examples 101 to 104 and Comparative Examples 101 to 104 were measured in the same manner as described above. The test results are shown in Table 231.

[0524]

[Table 231]

Next, the case where the compound represented by the general formula (1) and the compound represented by the general formula (28) are used in combination as the charge transporting material will be described with reference to Examples 105 to 108 and Comparative Examples 105 to 108.

Example 105 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 1 except that the coating liquid for the charge transport layer in Example 1 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 28-1 3 parts Compound NO. 1-1 compound 6 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Comparative Example 105 Example 105 was repeated except that the coating liquid for the charge transport layer in Example 105 was changed to the one having the following composition.
In the same manner as in the above, an electrophotographic photosensitive member of a comparative example was produced. [Coating solution for charge transport layer] Compound NO. Compound of 28-1 9 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300) 10 parts Tetrahydrofuran 75 parts

Example 106 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 2, except that the coating solution for the charge transport layer in Example 2 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 28-5 2 parts Compound NO. 1-6 compound 8 parts Polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite L-1250) 10 parts Methylene chloride 80 parts

[Comparative Example 106] In the coating liquid for the charge transporting layer of Example 106, Compound No. An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 106 except that the compound of No. 28-5 was not added.

Example 107 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating liquid for the charge transport layer in Example 3 was changed to the one having the following composition. [Coating solution for charge transport layer] Compound NO. Compound No. 28-30 4 parts Compound NO. 1-8 compound 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 107 Example 107 was repeated except that the coating liquid for the charge transport layer in Example 107 was changed to the one having the following composition.
In the same manner as in the above, an electrophotographic photosensitive member of a comparative example was produced. [Coating solution for charge transport layer] Compound NO. Compound of 28-30 9 parts Polycarbonate resin (Mitsubishi Gas Chemical Co., Ltd .: Iupilon Z-300) 10 parts Methylene chloride 50 parts 1,2-dichloroethane 35 parts

[Example 108] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to obtain a film having a thickness of 23.
A single-layer photosensitive layer having a thickness of μ was formed to prepare an electrophotographic photosensitive member of the present invention. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound No. 28-1 8 parts Compound NO. 1-1 compound 10 parts Tetrahydrofuran 200 parts

[Comparative Example 108] A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder and dried to give a thickness of 23.
A single-layer photosensitive layer was formed to prepare an electrophotographic photosensitive member of Comparative Example. [Coating solution for photosensitive layer] The same charge generating material as in Example 3 3 parts Polycarbonate (Panlite K-1300 manufactured by Teijin Chemicals Ltd.) 21 parts Compound NO. Compound of 28-1 18 parts Tetrahydrofuran 200 parts

The photoreceptor characteristics of each of the photoreceptors of Examples 105 to 108 and Comparative Examples 105 to 108 were measured in the same manner as described above. The test results are shown in Table 232.

[0535]

[Table 232]

[Comparative Example 109] The compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 1 except that the compound of 2-5 was changed to the following compound.

[0537]

Embedded image

[Comparative Example 110] The compound NO. An electrophotographic photosensitive member of a comparative example was prepared in the same manner as in Example 3, except that the compound of No. 2-32 was changed to the following compound.

[0539]

Embedded image

The test results of Comparative Examples 109 to 110 are shown in Table 233.

[0541]

[Table 233]

[0542]

As described above, by using a specific charge transporting material in combination, an abnormal image is not generated due to deterioration of the photosensitive layer due to cracks or the like even after repeated use without losing high sensitivity. Thus, an electrophotographic photosensitive member exhibiting excellent stability can be obtained.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view of a single-layer photoreceptor.

FIG. 2 is a cross-sectional view illustrating a configuration example of a laminated photoconductor.

FIG. 3 is a cross-sectional view illustrating a configuration example of a laminated photoconductor.

[Explanation of symbols]

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

 ──────────────────────────────────────────────────の Continued on the front page (72) Inventor Satoshi Kurimoto 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Co., Ltd.

Claims (29)

[Claims] 1. 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 (2) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group (where the substituent is a di-lower alkylamino group; Lower alkyl group, lower alkoxy group, halogen atom, aralkylamino group and amino group). 2. 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 (3) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. 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. 3. 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 (4) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ is a hydrogen atom, a halogen atom, a cyano group or a lower alkyl group, and Ar is (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 , A lower alkoxy group or a di-lower alkylamino group.). 4. 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 (5) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ is a hydrogen atom, a lower alkyl group, a chloroethyl group or a hydroxyethyl group, R ₂ is a hydrogen atom or a halogen atom, and R ₃ is a lower alkyl group, a di-lower alkylamino group, a diarylamino group. Substituted or unsubstituted styryl group, substituted or unsubstituted aromatic ring residue (aromatic ring is benzene ring, naphthalene ring or anthracene ring) or substituted or unsubstituted heterocyclic residue (heterocycle is pyridine ring, quinoxaline ring Or a carbazole ring). 5. 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 (6) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ is a lower alkyl group, R ₂ is a lower alkyl group, a di-lower alkylamino group, a diarylamino group, a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue (where the aromatic ring is A benzene ring, a naphthalene ring or an anthracene ring) or a substituted or unsubstituted heterocyclic residue (a heterocyclic ring is a pyridine ring, a quinoxaline ring or a carbazole ring). 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 In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ and R ₂ may be the same or different, and represent a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group, a chloro lower alkyl group, an alkyl acyl group having 1 to 2 carbon atoms, and an alkyl carbon number. 5 to 6 cycloalkyl groups or substituted or unsubstituted aralkyl groups. 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 In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ , 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, or a substituted or unsubstituted An aryl group of
R ₂ represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. However,
Except when R ₁ , R ₂ , R ₃ and R ₄ are all hydrogen atoms. K, l, m and n are 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. 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 In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, Ar ₁ represents a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and A represents a substituted or unsubstituted N-
A substituted carbazolyl group or (However, Ar ₂ represents a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) . 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 In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ is a hydrogen atom, an alkyl group, an alkoxy group,
An aryloxy group, a dialkylamino group, a diarylamino group or a halogen atom, R ₂ and R ₃ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and Ar is an aromatic hydrocarbon group or a heterocyclic group To n
Represents an integer of 1 or 2. 10. 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 (11) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ and R ₂ represent 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 In the substituted aryl group, R ₃ and R ₄ represent a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. Ar represents a substituted or unsubstituted monocyclic aromatic hydrocarbon group, a substituted or unsubstituted non-fused polycyclic aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic group. 11. 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 (12) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, A represents an N-substituted carbazolyl group or (Where Ar is an aromatic hydrocarbon group or a heterocyclic group, and R ₁ and R ₂ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group),
R is any one of an alkyl group, an alkoxy group and a halogen atom, n is an integer of 0 to 4, and when n ≧ 2, R may be the same or different. 12. 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 (13) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, A is a 9-anthryl group, substituted or unsubstituted N
A substituted carbazolyl group, a substituted or unsubstituted N-substituted phenothiazinyl group or (In the formula, Ar represents a substituted or unsubstituted arylene group; R ₁ and R ₂ represent a substituted or unsubstituted alkyl group;
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. Represent. m represents an integer of 2 to 8, and n represents an integer of 0 or 1. 13. 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 (14) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, A is a 9-anthryl group, substituted or unsubstituted N
A substituted carbazolyl group, a substituted or unsubstituted N-substituted phenothiazinyl group or (In the formula, Ar represents a substituted or unsubstituted arylene group; R ₁ and R ₂ represent a substituted or unsubstituted alkyl group;
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), and R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. Represent. n represents the integer of 0-8. 14. 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 (15) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different. 15. 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 (16) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image (In the formula, R ₁ and R ₂ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, R ₁
And at least one of R ₂ represents a substituted or unsubstituted aryl group. 16. 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 (17) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image (Wherein R ₁ and R ₂ are a substituted or unsubstituted alkyl group,
Represents a substituted or unsubstituted aryl group, R ₁ and R ₂
May be the same or different. R ₃ and R ₄ are hydrogen atoms,
Represents an alkyl group, an alkoxy group or a halogen atom,
Further, m is an integer of 1, 2, 3 and n is an integer of 1, 2, ₃ , _{4. When} m and n are respectively plural, R ₃ and R ₄ may be the same or different. 17. 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 (18) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, m is an integer of 0 or 1, and when m = 1, X
Is an oxygen atom, a sulfur atom, Wherein R ₁ and R ₂ are an alkyl group, an aralkyl group,
Represents a carbocyclic aromatic group or a double-ring group. 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 double-ring group. n is an integer of 0 or 1. R ₃ may form a benzene ring together with X. 18. 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 (19) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. 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,
An alkyl group which may have a cyano group or a substituent, an alkoxy group, an aryloxy group, an alkyl mercapto group,
Represents a methylenedioxy group, a methylenedithio group or an aryl group, and R ₁ , R ₂ and R ₃ may be the same or different. L, m, and n each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₁ , R _2, and R ₃ may be the same or different. 19. 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 (20) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, Ar represents a phenylene group or a biphenylene group;
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. 20. 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 (21) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, A ₁ and A ₂ 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 group. 21. 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 (22) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. 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 n represents 1 or 2
Represents an integer. R ₃ represents a hydrogen atom, a substituted or unsubstituted alkyl group or 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 or 3, l represents an integer of 1, 2, 3 or 4, and R ₄ and R ₅ may be the same or different when m and l are integers of 2 or more. . 22. 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 (23) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. n is 1, 2, 3
Or, represents an integer of 4, and m represents an integer of 4-n. When m is 2 or more, R ₁ may be the same or different. 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 or a substituted or unsubstituted aryl group. Represent. H is an integer of 1, 2, 3 or 4, k and l are 1,
Represents an integer of 2, 3, 4, or 5, and when h, k, and l are 2 or more, R ₂ , R ₃ , and R ₄ may be the same or different. 23. 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 (24) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. 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 alkyl group. Represents a group or a substituted or unsubstituted aryl group. m and n are integers of 1 or 2, and m + n = 3. However, when m or n is 2, A ₁ , A ₃ or A ₂ may be the same or different. 24. 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 (25) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, RI and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different. However, 1,6-diaminopyrene compounds are excluded. 25. 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 (26) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R ₁ and R ₂ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. 26. 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 (27) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, R is a lower alkyl group or a pendyl group, X is 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 pendyl group; Is an integer of 1 or 2. 27. 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 (28) on a conductive support. body. Embedded image In the formula, R ₁ and R ₃ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R ₂ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group. N is an integer of 0 or 1. Embedded image In the formula, 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,
R ₃ and R ₄ represent a hydrogen atom, a cyano group, an alkoxycarbonyl group or a substituted or unsubstituted alkyl group, and R ₅ represents a hydrogen atom, a lower alkyl group or an alkoxy group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, j is 1 to
5, k is 1-4, l is 0-2, m is 1 or 2, n is 1
Represents an integer of 1 to 3. 28. A charge generating layer containing a charge generating material as a main component and a charge transporting layer containing at least one set selected from the following compounds represented by 1 to 27 on a conductive support. An electrophotographic photoreceptor, comprising: 1. 1. Compound represented by general formula (1) and compound represented by general formula (2) 2. Compound represented by general formula (1) and compound represented by general formula (3) 3. Compound represented by general formula (1) and compound represented by general formula (4) 4. Compound represented by general formula (1) and compound represented by general formula (5) 5. Compound represented by general formula (1) and compound represented by general formula (6) 6. Compound represented by general formula (1) and compound represented by general formula (7) 7. Compound represented by general formula (1) and compound represented by general formula (8) 8. Compound represented by general formula (1) and compound represented by general formula (9) 9. Compound represented by general formula (1) and compound represented by general formula (10) Compound represented by general formula (1) and general formula (11)
10. The compound represented by Compound represented by general formula (1) and general formula (12)
12. A compound represented by the formula Compound represented by general formula (1) and general formula (13)
12. A compound represented by the formula: Compound represented by general formula (1) and general formula (14)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (15)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (16)
15. A compound represented by the formula: Compound represented by general formula (1) and general formula (17)
17. A compound represented by the formula: Compound represented by general formula (1) and general formula (18)
18. A compound represented by the formula: Compound represented by general formula (1) and general formula (19)
19. A compound represented by the formula: Compound represented by general formula (1) and general formula (20)
20. A compound represented by the formula: Compound represented by general formula (1) and general formula (21)
21. Compound represented by Compound represented by general formula (1) and general formula (22)
22. A compound represented by the formula: Compound represented by general formula (1) and general formula (23)
23. Compound represented by Compound represented by general formula (1) and general formula (24)
24. A compound represented by the formula: Compound represented by general formula (1) and general formula (25)
25. A compound represented by the formula: The compound represented by the general formula (1) and the general formula (26)
26. Compound represented by Compound represented by general formula (1) and general formula (27)
Compound represented by the following formula: 27. Compound represented by general formula (1) and general formula (28)
Compound represented by 29. An electron comprising a conductive support and a single photosensitive layer containing at least one selected from the group consisting of a charge generating material and a compound represented by the following formulas (1) to (27). Photoreceptor. 1. 1. Compound represented by general formula (1) and compound represented by general formula (2) 2. Compound represented by general formula (1) and compound represented by general formula (3) 3. Compound represented by general formula (1) and compound represented by general formula (4) 4. Compound represented by general formula (1) and compound represented by general formula (5) 5. Compound represented by general formula (1) and compound represented by general formula (6) 6. Compound represented by general formula (1) and compound represented by general formula (7) 7. Compound represented by general formula (1) and compound represented by general formula (8) 8. Compound represented by general formula (1) and compound represented by general formula (9) 9. Compound represented by general formula (1) and compound represented by general formula (10) Compound represented by general formula (1) and general formula (11)
10. The compound represented by Compound represented by general formula (1) and general formula (12)
12. A compound represented by the formula Compound represented by general formula (1) and general formula (13)
12. A compound represented by the formula: Compound represented by general formula (1) and general formula (14)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (15)
14. A compound represented by the formula: Compound represented by general formula (1) and general formula (16)
15. A compound represented by the formula: Compound represented by general formula (1) and general formula (17)
17. A compound represented by the formula: Compound represented by general formula (1) and general formula (18)
18. A compound represented by the formula: Compound represented by general formula (1) and general formula (19)
19. A compound represented by the formula: Compound represented by general formula (1) and general formula (20)
20. A compound represented by the formula: Compound represented by general formula (1) and general formula (21)
21. Compound represented by Compound represented by general formula (1) and general formula (22)
22. A compound represented by the formula: Compound represented by general formula (1) and general formula (23)
23. Compound represented by Compound represented by general formula (1) and general formula (24)
24. A compound represented by the formula: Compound represented by general formula (1) and general formula (25)
25. A compound represented by the formula: The compound represented by the general formula (1) and the general formula (26)
26. Compound represented by Compound represented by general formula (1) and general formula (27)
Compound represented by the following formula: 27. Compound represented by general formula (1) and general formula (28)
Compound represented by