JPH01118144A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain a single layer type photosensitive body superior in positive chargeability, high in sensitivity and small in residual potential by forming a photosensitive layer composed of a specified perylene derivative, a diamine derivative, and a binder resin. CONSTITUTION:The single layer type photosensitive layer comprises as an electric charge generating material, the perylene derivative represented by formula I, each of R<1>-R<4> being lower alkyl, as a charge transfer material, the diamine derivative represented by formula II, each of R<5>-R<8> being H, lower alkyl, or the like; Y being H, lower alkoxy, or the like; l being an integer of 1-3, and each of m, n, o, and p being is an integer of 0-2, and the binder resin, thus permitting the obtained single layer type photosensitive body to be superior in positive chargeability, high in sensitivity, and small in residual potential.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an electrophotographic photoreceptor suitably used in an image forming apparatus such as a copying machine.

<Problems to be solved by conventional technology and inventions> In recent years,
As a photoreceptor for electrophotography, there is a large degree of freedom in functional design.In particular, a laminated type photoreceptor that separates each function by a charge-generating material that generates charges when exposed to light and a charge-transporting material that transports the generated charges. Electrophotographic photoreceptors having layers have been proposed. For example, a charge generation layer containing a squaric acid derivative as a charge generation material and a diamine derivative such as 4,4'-bis[N-phenyl-N-(3-methylphenyl)aminococyphenyl] are formed on a conductive substrate. Electrophotographic photoreceptor laminated with a charge transport layer containing
038), a cyanine compound, an azo compound, N.

N'-bis(2,4,6-drimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N
, N'-diphenylperylene-3,4゜9.10-tetracarboxydiimide, N,N'-dimethylperylene-3,4,9,10-tetracarboxydiimide, and other perylene compounds for electrophotography. Photoreceptor (Unexamined Japanese Patent Publication No. 5
7-144558, JP 57-144557, JP 80-207148, JP 81-
275848, Japanese Patent Laid-Open No. 132955/1983), etc. have been proposed.

In the photoreceptor having the laminated photosensitive layer described above, the charge generation function and the generated charge transport function can be separated by the charge generation layer and the charge transport layer as described above, so that the photoreceptor generally has a high sensitivity. This method has the advantage that not only a photoreceptor for electrophotography can be obtained, but also a wide range of photosensitive and photosensitive materials can be selected. However, since the charge transport material is generally a hole transport material, it is difficult to positively charge the photoreceptor, and it is also difficult to obtain a positively charged toner that develops the electrostatic latent image formed on the photoreceptor. The selection range of materials becomes narrower.

In addition, when negatively charged by corona discharge, ozone is generated, which is not only undesirable from a safety and health perspective, but also requires an exhaust passage to exhaust ozone in image forming devices such as copying machines, which makes the device large. become Furthermore,
Since the charge generation layer has a thin layer thickness of 1 to 2 μm, it is not only necessary to form the charge generation layer with high precision, but also a charge transport layer must be formed on the charge generation layer, which makes it difficult to manufacture the photoreceptor. There are problems such as the number of steps increases, work efficiency decreases, yields decrease, and costs increase.

On the other hand, an electrophotographic photoreceptor having a single-layer photoreceptor layer containing a charge-generating material, a charge-transporting material, and a binder resin is also known, and the photoreceptor can be positively charged and can prevent the generation of ozone. In addition, it has advantages such as a wide selection range of toner materials and good manufacturing workability. In order to take advantage of these advantages, when the charge generating material and charge transporting material used in the laminated photosensitive layer are applied to the single layer photosensitive layer, the photoreceptor having the single layer photosensitive layer can be There is a problem in that it does not exhibit suitable electrophotographic characteristics. More specifically, unlike the laminated photosensitive layer, in a single layer photosensitive layer, a charge generation material and a charge transport material are mixed in the photosensitive layer, and the charge generation function and the charge transport function are combined. Since it is difficult to separate these materials, the selection range for each material is not only narrow, but also the sensitivity is low and the residual potential is high.

Moreover, the electrophotographic properties described above are greatly influenced by the combination of the charge generating material and the charge transporting material.

For example, since the diamine derivative used as a charge transport material has a small dependence of drift mobility on electric field intensity, a photoreceptor having a single-layer photosensitive layer containing the diamine derivative is expected to exhibit a small residual potential. However, when a single-layer photosensitive layer is constructed by combining the above-mentioned various perylene compounds as charge-generating materials, the residual potential of the photoreceptor having the single-layer photosensitive layer is still high and the sensitivity is insufficient.
There is a problem in that it does not exhibit sufficient electrophotographic properties.

Regarding the photoreceptor having a single layer type photoreceptor mentioned above, the photoreceptor having a single layer type photoreceptor (specially JP-A No. 5G-143438) has been proposed.

However, in the above-mentioned photoreceptor, not only does it not have sufficient positive chargeability, but also the drift mobility of polyvinylcarbazole as a charge transporting material is small, and the drift mobility shows a large dependence on electric field intensity, so the residual potential is large. In addition, the sensitivity is low and it still does not exhibit sufficient electrophotographic properties.

In view of the above points, in order to provide an electrophotographic photoreceptor that has excellent chargeability and sensitivity and has a small residual potential while taking advantage of the advantages of the single-layer type photosensitive layer, the present applicant first developed N, Perylene compounds such as N'-bis(3,5-dimethylphenyl)perylene-3,4,9,, 10-tetracarboxydiimide, N-methyl-3-carbazolyl aldehyde, N,N-diphenylhydrazone, etc. proposed a photoreceptor having a single-layer type photoreceptor layer consisting of a combination of hydrazone-based compounds (Japanese Patent Application No. 107780/1982).
.

However, the above-mentioned hydrazone-based compounds still have a large dependence of drift mobility on electric field strength, a high residual potential, and insufficient sensitivity. Moreover, although the above-mentioned hydrazone-based compounds have a smaller degree of photoisomerization upon light irradiation than 4-(N,N-diethylamino)benzaldehyde N,N-diphenylhydrazone, etc., their photostability is still insufficient, so they can be repeatedly used. There are problems in that sensitivity decreases and residual potential increases with use.

<Object of the Invention> The present invention has been made in view of the above-mentioned problems, and provides an inexpensive single-layer photosensitive layer that has excellent positive chargeability and photostability, has high sensitivity and surface potential, and has a small residual potential. An object of the present invention is to provide an electrophotographic photoreceptor having the following characteristics.

Means and Effects for Solving the Problems> In order to achieve the above object, the electrophotographic photoreceptor of the present invention has a single-layer type photoreceptor layer containing a charge generation material, a charge transport material, and a binder resin. In the photoreceptor having the above-mentioned charge generating material, the following -
It is a perylene compound represented by Formation (1), and is characterized in that the charge transport material is a diamine derivative represented by Formation (2) below.

(In the formula, R1, R2, R3 and R4 represent a lower alkyl group) (In the formula, R5, Re, R7 and R8 are the same or different and are a hydrogen atom, a child, a lower alkyl group, a lower alkoxy group or represents a halogen atom.Y represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom) represents an integer of 1 to 3. m, nSo and p are 0
Indicates an integer between ~2.

However, R5, R6, R7 and R8 are not hydrogen atoms at the same time, and the above-mentioned R5, R6, R7 which are not hydrogen atoms
and at least 21 of m, n, o and p of R8 shall be 2. ) The present invention will be explained in detail below.

The electrophotographic photoreceptor of the present invention has a single-layer type photosensitive layer, and the photosensitive layer has the above-mentioned formation (1) as a charge generating material.
), a diamine derivative represented by the above general formula (2) as a charge transport material, and a binder resin.

The lower alkyl group in the above general formula (1) and general formula (2) includes an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, and hexyl group. Illustrated. Among the lower alkyl groups mentioned above, alkyl groups having 1 to 4 carbon atoms are preferred.

Further, as the lower alkoxy group in the above general formula (2), methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy,
1 to 6 carbon atoms such as pentyloxy and hexyloxy groups
An example is an alkoxy group.

Among the lower alkoxy groups mentioned above, alkoxy groups having 1 to 4 carbon atoms are preferred.

Furthermore, examples of the halogen atom include fluorine, chlorine, bromine, and iodine atoms.

The above substituents R5, R6, R7, and R8 may be substituted at any of the ○-position, m-position, and p-position of the benzene ring, and the substituent Y may be substituted at any appropriate position of the benzene ring. may be replaced with

The perylene compounds represented by the above general formula (1) include N,N'-di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,
N'-di(3-methyl-5-ethylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,
N'-di(3,5-diethylphenyl)perylene-3,
4,9,10-tetracarboxydiimide, N,N'-
Di(3,5-dipropylphenyl)perylene-3,4,
9,10-tetracarboxydiimide, N,N'-di(
3゜5-diisopropylphenyl)perylene-3,4゜9.10-tetracarboxydiimide, N,N'-di(3-methyl-5-isopropylphenyl)perylene-
3,4,9,10-tetracarboxydiimide, N, N
'-di(3-ethyl-5-isopropylphenyl)perylene-3,4,9,10-tetracarboxydiimide,
N,N'-di(3,5-dibutylphenyl)perylene-
3,4,9,10-tetracarboxydiimide, N, N
'-di(3゜5-di-tert-butylphenyl)perylene-3゜4, 9.10-tetracarboxydiimide, N+N'-di(3,5-diethylphenyl)perylene-3,4,9,10- Tetracarboxydiimide, N,
N'-di(3,5-diethylphenyl)perylene-3,
Examples include 4,9,10-tetracarboxydiimide.

Among the above perylene compounds, those having an alkyl group having 1 to 4 carbon atoms, especially N,N'-di(3,5-
Dimethylphenyl)perylene-3°4,9.10-tetracarboxydiimide is preferred. The above perylene compounds may be used alone or in combination of two or more.

Further, in the diamine derivative represented by the above general formula (2), among the p-phenylenediamine derivatives of J-1,
Preferred compounds include, for example, 1-[N-(3,
5-dimethylphenyl)-N-phenylamino] -4
-(N,N-diphenylamino)benzene, 1-[N
, N-di(3,5-dimethylphenyl)amino]-4-
(N,N-diphenylamino)benzene, 1.4-bis[N-(2゜4-dimethylphenyl)-N-phenylaminocobenzene, 1.4-bis[N-(2,6-dimethylphenyl) -N-phenylaminocobenzene, 1.4
-bis[N-(3,5-dimethylphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-bis(
3,5-dimethylphenyl)aminocobenzene, 1-
[N,N-di(2,4-dimethylphenyl)amino]-
4-[N,N-di(2,6-dimethylphenyl)aminocobenzene, 1-[N,N-di(2,4-dimethylphenyl)amino]-4-[N,N-di(3, 5-dimethylphenyl)aminocobenzene, 1-[N,N-di(
2,6-dimethylphenyl)amino]-4-[N,N-
Di(3,5-dimethylphenyl)aminocobenzene, 1
-[N,N-di(3,5-dimethylphenyl)amino]
-4-(N,N-diphenylamino)-2-methylbenzene, 1,4-bis[N-(3,5-dimethylphenyl)-N-phenyl-amino]-2-methylbenzene,
1.4-bis(3,5-dimethylphenyl)aminoco-
2-Methylbenzene, 1,4-bis[N-(3,5=dimethylphenyl)-N-phenylaminoco-2-methoxybenzene, 1,4-bis[N,N-bis(3,5- dimethylphenyl)aminoco-2-methoxybenzene, 1
,4-bis[N-(3゜5-dimethylphenyl)-N-
Phenylaminoco-2-chlorobenzene, 1,4-bis[N,N-bis(3,5-dimethylphenyl)aminoco-2-chlorobenzene, 1,4-bis[N-(3,5-
dimethylphenyl)-N-phenylaminoco-2-bromobenzene, 1,4-bis[N-(2゜4-diethylphenyl)-N-phenylaminocobenzene, 1,4-bis[N-(3, 5-diethylphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-bis(3,
5-diethylphenyl)aminocobenzene, 1,4-bis[N-(3,5-dipropylphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-bis(3
,5-dipropylphenyl)aminocobenzene, 1-
[N,N-di(3,5-diisopropylphenyl)amino]-4-(N,N-diphenylamino)benzene,
1,4-bis[N-(3゜5-diisopropylphenyl)-N-phenylaminocobenzene, 1,4-bis[N
, N-bis(3,5-diisopropylphenyl)aminocobenzene, 1,4-bis[N-(3,5-dibutylphenyl)-N-phenylaminocobenzene, 1゜4-bis[N,N- Bis(3,5-dibutylphenyl)aminocobenzene, 1,4-bis[N-(3,5-diisobutylphenyl)-N-phenylaminocobenzene, 1,4
-bis[N,N-bis(3,5-diisobutylphenyl)aminocobenzene, 1-[N,N-di(3,5-ditart-butylphenyl)amino]-4-(N
, N-diphenylamino)benzene, 1,4-bis[N
-(3,5-di-tert-butylphenyl)-N-phenylami, nocobenzene, 1,4-bis[N, N
-bis(3,5-di-tert-butylphenyl)aminocobenzene, 1-[N-(3,5-dimethylphenyl)-N-phenylamino] -4-[N-(3,5-
diethylphenyl)-N-phenylaminocobenzene,
1-[N,N-di(3,5-dimethylphenyl)amino] -4-[N,N-di(3,5-diethylphenyl)
Aminocobenzene, 1-[N-(3,5-dimethylphenyl)-N-phenylamino]-4-[N-(3,
5-diisopropylphenyl)-N-phenylaminocobenzene, 1-[N,N-di(3,5-dimethylphenyl)amino]-4-[N,N-di(3,5-diisopropylphenyl)aminocobenzene Benzene, 1-[N-(3
,5-dimethoxyphenyl)-N-phenylamino]
-4-(N,N-diphenylamino)benzene, 1-
[N,N-di(3,5-dimethoxyphenyl)amino]
-4-(N,N-diphenylamino)benzene, 1.
4-bis[N-(2,4-dimethoxyphenyl)-N-
Phenylaminocobenzene, 1,4-bis[N-(3;
5-dimethoxyphenyl)-N-phenylaminocobenzene, 1,4-bis[N-(2,6-dimethoxyphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-bis(3 ,5-dimethoxyphenyl)aminocobenzene, 1-[N,N-di(2,4-dimethoxyphenyl)aminoco-4-[N,N-di(2,6-dimethoxyphenyl)aminocobenzene, 1- [N, N-
Di(2,4-dimethoxyphenyl)amino L-4-[N
, N-di(3,5-dimethoxyphenyl)aminocobenzene, 1-[N,N-di(2,6-dimethoxyphenyl)amino] -4-[N,N-di(3,5-dimethoxyphenyl) ) aminocobenzene, 1,4-bis[N-(
3,5-jethoxyphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-di(3,5-jethoxyphenyl)aminocobenzene, 1,4-bis[N-
(3,5-diproboxydiphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-di(3,5-
dipropoxyphenyl)aminocobenzene, 1-[N,
N-di(3,5-diisopropoxyphenyl)amino]
-4-(N,N-diphenylamino)benzene, 1.
4-bis[N-(3,5-diisopropoxyphenyl)
-N-phenylaminocobenzene, 1,4-bis[N,
N-bis(3,5-diisopropoxyphenyl)aminocobenzene, 1.4-bis[N-(3,5-dibutoxyphenyl)-N-phenylaminocobenzene, 1.4-
Bis[N,N-bis(3,5-dibutoxyphenyl)aminocobenzene, 1,4-bis[N-(3゜5-diisobutoxyphenyl)-N-phenylaminocobenzene,
1,4-bis[N,N-bis(3,5-diisobutoxyphenyl)aminocobenzene, 1-[N-(3,5-
tert-butoxyphenyl)-N-phenylamino]-4-(N.

N-diphenylamino)benzene, 1-[N,N-di(3,5-di-tert-butoxyphenyl)amino]
-4-(N,N-diphenylamino)benzene, 1,
4-bis[N-(3,5-di-tert-butoxyphenyl)-N-phenylaminocobenzene, 1,4-bis[N,N-bis(3,5-di-tert-butoxyphenyl)aminocobenzene , 1-[N-(3,5-
dimethoxyphenyl)-N-phenylamino] -4-
[N-(3,5-jethoxyphenyl)-N-phenylaminocobenzene, 1-[N,N-di(3,5-dimethoxyphenyl)amino]-4-[N,N-di(3,
5-jethoxyphenyl)aminocobenzene, 1-[N
-(3,5-dimethoxyphenyl)-N-phenylamino] -4-[N-(3,5-diisopropoxyphenyl)=N-phenylaminoconzene, 1-[N,N
-di(3,5-dimethoxyphenyl)amino] -4-
[N,N-di(3,5-diisopropoxyphenyl)aminocobenzene, 1-[N-(3,5-')chlorophenyl)-N-phenylamino] -4-(N,N-diphenylamino ) benzene, 1-[N,N-di(3,5
-dichlorophenyl)amino] -4-(N,N-diphenylamino)benzene, 1,4-bis[N-(2,4
-dichlorophenyl)-N-phenylaminocobenzene, 1,4-bis[N-(2,6-dichlorophenyl)-
N-phenylaminocobenzene, 1°4-bis[N-(
3,5-dichlorophenyl)-N-phenylaminocobenzene, 1-[N,N-di(2,4-dichlorophenyl)amino]-4-[N,N-di(2,6-dichlorophenyl)aminocobenzene , 1-[N, N-di(2,4
-dichlorophenyl)aminoco-4-IN, N-di(3
゜5-dichlorophenyl)aminocobenzene, 1-[N
, N-di(2,6-dichlorophenyl)amino] -4
-[N,N-di(3,5-dichlorophenyl)amino2
]Benzene, 1,4-bis[N-(3,5-')'10
lophenyl)-N-phenylaminoco-2-chlorobenzene, 1,4-bis[N.

N-bis(3,5-dichlorophenyl)aminoco-2-
Chlorobenzene, 1,4-bis[N-(3゜5-dibromophenyl)-N-phenylaminocobenzene, 1,4
-bis[N,N-bis(3,5-dibromophenyl)aminocobenzene and the like are exemplified.

Among the benzidine derivatives of J-2, preferred compounds include, for example, 4-[N,-(3゜5-dimethylphenyl)-N-phenylamino]-4'-(N,
N-diphenylamino)diphenyl, 4-[N,N-
di(3,5-dimethylphenyl)amino] -4' -
(N,N-diphenylamino)diphenyl, 4,4'-
Bis[N-(2,4-dimethylphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N-(2,6
-dimethylphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminococyphenyl, 4-[N,
N-di(2,4-dimethylphenyl)amino] -4'
-[N,N-di(2,6-dimethylphenyl)aminococyphenyl, 4-[N,N-di(2,4-dimethylphenyl)amino]-4'-[N,N-di(3, 5-dimethylphenyl)aminococyphenyl, 4-[N,N
-di(2,6-dimethylphenyl)amino] -4'
-[N,N-di(3,5-dimethylphenyl)aminococyphenyl, 4-[N-(3,5-dimethylphenyl)-N-phenylaminoco-4' -(N,N-diphininylamino )-2,2'-dimethyldiphenyl, 4-
[N,N-di(3,5-dimethylphenyl)amino]
-4' = (N,N-diphenylamino)-2,2'
-dimethyldiphenyl, 4,4' -bis[N-(3,
5-dimethylphenyl)-N-phenylamino]-2,
2'-dimethyldiphenyl, 4,4'-bis[N-
(3,5-dimethylphenyl)-N-phenylamino]
-3,3'-dimethyldiphenyl, 4,4'-bis[
N,N-di(3゜5-dimethylphenyl)amino] -
2,2'-dimethyldiphenyl, 4,4'-bis[N
-(3゜5-dimethylphenyl)-N-phenylaminoco-2,2'-dimethoxydiphenyl, 4,4'-bis[N,N-di(3,5-dimethylphenyl)aminoco-2,2 '-dimethoxydiphenyl, 4゜4'-bis[
N-(3,5-dimethylphenyl)-N-phenylamino]-2,2'-dichlorodiphenyl, 4,4'-bis[N,N-di(3,5-dimethylphenyl)amino]
-2,2'-dichlorodiphenyl, 4,4'-bis[
N-(3,5-diethylphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N-di(3,5
-diethylphenyl)aminococyphenyl, 4°4'
-bis[N-(3,5-dipropylphenyl)-N-phenylaminococyphenyl, 4.4' -bis[N,N
-di(3,5-dipropylphenyl)aminococyphenyl, 4- [N,N-di(3,5-diisopropylphenyl)amino] -4' -(N,N-diphenylamino)diphenyl, 4゜4 ' -bis[N-(3,5-
diisopropylphenyl)-N-phenylaminococyphenyl, 4゜4'-bis[N,N-di(3,5-diisopropylphenyl)aminococyphenyl, 4.4'-
Bis[N-(3,5-dibutylphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N.

N-di(3,5-dibutylphenyl)aminococyphenyl, 4,4'-bis[N-(3,5-diisobutylphenyl)-N-phenylaminococyphenyl, 4,4'-
Bis[N,N-di(3,5-diisobutylphenyl)aminococyphenyl, 4-[N,N-di(3,5-dit)
ert-butylphenyl)amino] -4' -(N,
N-diphenylamino)diphenyl, 4,4'-bis[N-(3゜5-di-tert-butylphenyl)-N
-phenylaminococyphenyl, 4,4'-bis[N,
N-di(3,5-di-tert-butylphenyl)aminococyphenyl, 4-[N-(3,5-dimethoxyphenyl)-N-phenylamino]-4'-(N.

N-diphenylamino)diphenyl, 4-[N.

N-di(3,5-dimethoxyphenyl)amino]-4'
-(N,N-diphenylamino)diphenyl, 4,4
' -bis[N-(2,4-dimethoxyphenyl)-N
-phenylaminococyphenyl, 4,4'-bis[N-
(2,6-dimethoxyphenyl)-N-phenylaminococyphenyl, 4゜4'-bis[N-(3,5-dimethoxyphenyl)-N-phenylaminococyphenyl,
4.4'-bis[N,N-di(3,5-dimethoxyphenyl)aminococyphenyl, 4-[N,N-di(2
,4-dimethoxyphenyl)amino] -4' -[
N.

N-di(2,6-dimethoxyphenyl)aminococyphenyl, 4-[N,N-di(2,4-dimethoxyphenyl)amino]-4'-[N,N-di(3,5-dimethoxyphenyl) ) aminococyphenyl, 4-[N,N
-di(2,6-dimethoxyphenyl)amino] -4'
-[N,N-di(3,5-dimethoxyphenyl)aminococyphenyl, 4゜4'-bis[N-(3,5-dimethoxyphenyl)-N-phenylamino]-2,2'
-dimethyldiphenyl, 4,4'-bis[N-(3,5
-dimethoxyphenyl)-N-phenylamino]-3°3'-dimethyldiphenyl, 4,4'-bis[N.

N-di(3,5-dimethoxyphenyl)aminoco-2,
2'-dimethyldiphenyl, 4,4'-bis[N-(3
,5-dimethoxyphenyl)-N-phenylamino]-
2,2'-dimethoxydiphenyl, 4,4'-bis[
N,N-di(3,5-dimethoxyphenyl)amino]-
2,2'-dimethoxydiphenyl, 4,4'-bis[
N-(3,5-dimethoxyphenyl)-N-phenylamino]-2,2'-dichlorodiphenyl, 4,4'-bis[N,N-di(3,5-dimethoxyphenyl)amino 1-2. 2'-dichlorodiphenyl, 4゜4'-bis[
N-(3,5-jethoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N-di(3
,5-jethoxyphenyl)aminocodiphenyl, 4
,4'-bisCN-(3゜5-dipropoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N-di(3,5-dipropoxyphenyl)aminococyphenyl, 4 - [N,N-di(3,5-diisopropoxyphenyl)amino] -4' -(N,N-diphenylamino)diphenyl, 4,4' -bis[N-
(3,5-diisopropoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N-di(
3,5-diisopropoxyphenyl)aminococyphenyl, 4,4'-bis[N-(3,5-dibutoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N, N- Di(3,5-dibutoxyphenyl)aminococyphenyl, 4,4'-bis[N-(3,5-diisobutoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N -di(3,5-diisobutoxyphenyl)aminococyphenyl, 4-[N,N
-di(3,5-di-tert-butoxyphenyl)amino] -4'-(N,N-diphenylamino)diphenyl, 4,4'-bis[N-(3,5-di-tert-
butoxyphenyl)-N-phenylaminococyphenyl, 4,4'-bis[N,N-di(3,5-di-ter
t-butoxyphenyl)aminococyphenyl, 4-[N
, N-di(3,5-dichlorophenyl)amino] -4
' -(N,N-diphenylamino)diphenyl, 4°4'-bis[N-(2,4-dichlorophenyl)-N-
Phenylaminococyphenyl, 4,4'-bis[N-
(2,6-dichlorophenyl)-N-phenylaminococyphenyl, 4.4'-bis[N-(3,5-dichlorophenyl)-N-phenylaminococyphenyl, 4.
4'-bis[N.

N-di(3,5-dichlorophenyl)aminococyphenyl, 4-[N,N-di(2,4-dichlorophenyl)
amino] -4' -CN, N-di(2゜6-dichlorophenyl)aminococyphenyl, 4-[N,N-di(
2,4-dichlorophenyl)aminoco-4'-[N,
N-di(3,5-dichlorophenyl)aminococyphenyl, 4-[N,N-di(2,6-dichlorophenyl)
amino]-4'-[N,N-di(3,5-dichlorophenyl)aminococyphenyl, 4-[N,N-di(3,
5-dibromophenyl)amino] -4' -(N,N
-diphenylamino)diphenyl, 4,4'-bis[
N-(3,5-dibromophenyl)-N-phenylaminococyphenyl, 4,4'-bis[N.

N-di(3,5-dibromophenyl)aminococyphenyl, 4,4'-bis[N-(3,5-dichlorophenyl)-N-phenylami/] -2゜2'-dichlorodiphenyl, 4,4' -Bis[N.

N-di(3,5-dichlorophenyl)amino]-2,2
'-Dichlorodiphenyl and the like are exemplified.

Further, among the 4,4'-terphenyldiamine derivatives of J-3, preferred compounds include, for example, 4-[N
-(3,5-dimethylphenyl)-N-phenylamino] -4' -(N,N-diphenylamino)-1,1
':4', 1'-terphenyl, 4-[N,
N-bis(3,5-dimethylphenyl)amino] -4
'-(N,N-diphenylamino)-1,1':
4', 1'-terphenyl, 4,4'-bis[N-(
'2,4-dimethylphenyl)-N-phenylamino]
-1,1':4'.

1'-terphenyl, 4,4'-bis[N-(,2゜6
-dimethylphenyl)-N-phenylaminoco-1,1
':4', 1'-terphenyl, 4°4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]-1,1':4', 1'-terphenyl,
4.4'-bis[N,N-di(3,5-dimethylphenyl)amino]-1°1': 4',1'-terphenyl, 4-[N,N-di(2,4- dimethylphenyl)amino]-4'-[N,N-di(2,6-dimethylphenyl)amino]-1,1':4',1'-terphenyl,4-[N,N-di(2 ,4-dimethylphenyl)amino]-4'-[N,N-di(3,5-
dimethylphenyl)amino]-1,1':4',
1'-terphenyl, 4-[N,N-di(2,6-
dimethylphenyl)amino] -4'-[N,N-di(
3,5-dimethylphenyl)amino]-1°1':
4', 1'-terphenyl, 4,4'-bis[N-(
3,5-dimethylphenyl)-N-(3,5-diethylphenyl)aminoco-1゜1',4/,1'-terphenyl, 4,4'-bis[N-(3,5-dimethylphenyl) )-N-(3,5-diisopropylphenyl)
amino]-1,1':4', 1'-terphenyl, 4,4'-bis[N-(3,5-dimethylphenyl)
-N-phenylamino]-3,3'-dimethyl-1゜1
': 4', 1'-terphenyl, 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino] 73+ 3', 3'-trimethyl-1,
1', 4/, 1'-terphenyl, 4,4'-bis[N,N-di(3,5-dimethylphenyl)amino]
-3,3',3'-)dimethyl-1゜1':4
', 1'-terphenyl, 4,4'-bis[N-(3
,5-dimethylphenyl)-N-phenylamino]-3
,3'3'-1rimethoxy-1,1':4'
, 1'-terphenyl, 4,4'-bis[N,N-di(
3,5-dimethylphenyl)aminoco-3,3'-dimethoxy-1,1': 4',1'-terphenyl, 4
,4'-bis[N-(3,5-dimethylphenyl)-N
-phenylamino]-3,3',3'-trichloro-
1°1': 4', 1'-terphenyl, 4,4'
-bis[N,N-di(3,5-dimethylphenyl)amino co-3. 3',
3' - Tori Ro Ro - 1.
1': 4', 1'-terphenyl, 4.4'
-bis[N-(2,4-dimethoxyphenyl)-N-phenylamino]-1,1': 4', 1'-terphenyl, 4,4'-bis[N-(2,6-dimethoxyphenyl) )-N-phenylamino]-1,1':4'
, 1'-terphenyl, 4,4'-bis[N-(3,5
-dimethoxyphenyl)-N-phenylamino]-1,
1':4', 1'-terphenyl, 4.4'-
Bis[N,N-di(3,5-dimethoxyphenyl)amino]-1,1':4'.

1'-terphenyl, 4-[N,N-di(2,4-dimethoxyphenyl)amino] -'4' -[N.

N-di(2,6-dimethoxyphenyl)amino]-1,
1':4', 1'-terphenyl, 4-[N, N
-di(2,4-dimethoxyphenyl)amino] -4'
-[N,N-di(3,5-dimethoxyphenyl)amino]-1,1':4',1'-terphenyl,
4-[N,N-di(2,6-dimethoxyphenyl)amino-4'-[N,N-di(3,5-dimethoxyphenyl)amino]-1°1':4',1'-tel Phenyl, 4,4'-bis[N-(3,5-jethoxyphenyl)-N=phenylamino]-1,1':4
', 1'-terphenyl, 4,4'-bis[N,N-
di(3,5-jethoxyphenyl)amino]-1,1'
:4',1'-terphenyl, 4,4'-bis[N
-(3,5-dipropoxyphenyl)-N-phenylamino]-1,1',4/,1'-terphenyl,
4,4'-bis[N,N-di(3,5-dipropoxyphenyl)amino]-1,1':4'.

1'-terphenyl, 4,4'-bis[N-(35-diisopropoxyphenyl)-N-phenylaminoco-1
,1':4',1'-terphenyl,4.4'-
Bis[N,N-di(3,5-diisopropoxyphenyl)amino]-1,1':4'.

1'-terphenyl, 4,4'-bis[N-(3゜5-
dibutoxyphenyl)-N-phenylamino]-1,1
':4', 1'-terphenyl, 4゜4'-bis[N,N-di(3,5-dibutoxyphenyl)aminoco-1,1':4', 1'-terphenyl, 4, 4
'-bis[N-(3,5-diisobutoxyphenyl)-
N-phenylaminoco-1,1': 4', 1'-
Terphenyl, 4,4'-bis[N,N-di(3,5-
diisobutoxyphenyl)amino]-1,1' :4
', 1'-terphenyl, 4,4'-bis[N-(3,
5-di-tert-butoxyphenyl)-N-phenylamino]-1,1': 4',1'-terphenyl,
4゜4'-bis[N,N-di(3,5-di-tert-
butoxyphenyl)amino]-1,1'24'.

1'-terphenyl, 4,4'-bis[N-(2゜4-
dichlorophenyl)-N-phenylamino]-1,1'
:4/, 1'-terphenyl, 4゜4''-bis[
N-(2,6-dichlorophenyl)-N-phenylamino]-1,1':4', 1'-terphenyl,
4,4'-bis[N-(3,5-dichlorophenyl)-
N-phenylamino]-1,1':4',1'-
Terphenyl, 4,4'-bis[N,N-di(3,5-
dichlorophenyl)amino]-1,1':4',
1'-terphenyl, 4-[N,N-di(2,4-dichlorophenyl)aminoco-4'-[N,N-di(2
,6-dichlorophenyl)aminoco-1,1' :4
',1'-terphenyl, 4-[N,N-di(2
14-dichlorophenyl)amino] -4' -[N,
N-di(3,5-dichlorophenyl)aminoco-1゜1
':4', 1'-terphenyl, 4-[N, N
-di(2,6-dichlorophenyl)aminoco-4' -
[N,N-di(3,5-dichlorophenyl)aminoco-
Examples include 1,1', 4/, and 1'-terphenyl.

The above diamine derivatives may be used alone or in combination of two or more. The above diamine derivatives have good molecular symmetry, and are similar to conventional 4-(N,N-diethylamino)benzaldehyde N,N-diphenylhydrazone and N-methyl-3-carbazolylaldehyde N,N-diphenylhydrazone. As shown in FIG. 1, no isomerization reaction occurs upon irradiation with 1 beam of light, and not only is the photostability excellent, but the drift mobility is large, and the dependence of the drift mobility on electric field strength is small. More specifically, taking 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminococyphenyl (compound A) as an example, the electric field is 2.0X105V/- (low electric field ) and 5.0×10 V/cIA (high electric field), conventional charge transport materials such as polyvinylcarbazole (compound B), N-ethyl-3-carbazolyl aldehyde N.

N-diphenylhydrazone (compound C), 1-phenyl-3-(4-diethylaminostyryl)-5-(4-
Diethylaminophenyl) pyrazoline (compound D), as shown in the table below, a photoreceptor having a single-layer type photosensitive layer can be produced by combining a diamine derivative having the above-mentioned characteristics with the above-mentioned perylene compound. Even though
High sensitivity and low residual potential can be obtained.

In addition, the compound represented by the above-mentioned -formation (2) can be prepared by various methods, for example, the compound represented by the following -formation (3) and the compounds represented by general formulas (4) to (7) may be simultaneously or It can be produced by sequential reactions.

(In the formula, R5, R6, R7, Re, Ys Js m.

nSo and p are the same as above. X represents a halogen atom. ) The compound represented by the above-formation (3) and the general formulas (4) to (
The reaction with the compound represented by the compound is usually carried out in an organic solvent, and any solvent can be used as long as it does not adversely affect this reaction. For example, nitrobenzene, dichlorobenzene, quinoline, N , N-dimethylformamide, N-methylpyrrolidone, and dimethylsulfoxide. The reaction is usually carried out using a catalyst such as copper powder, copper oxide, or copper halide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
It is carried out at a temperature of 150 to 250°C in the presence of a basic substance such as sodium carbonate or potassium hydrogen carbonate.

In addition, in the compound represented by the -formation (2), the substitution positions of the substituents R5, R6, R7, and R8 are controlled, and the compound represented by the general formula (2a) has a symmetrical structure, For example, after obtaining the compound represented by general formula (9) by the reaction of the compound represented by -formation (8) below with the compound represented by general formula (4) (6), then -formation After hydrolyzing and deacylating the compound represented by (9) to obtain the compound represented by -formation (10),
Furthermore, it can be produced by reacting with a compound represented by -Formation (5) (7).

(9) < 10 ) (5)
(7) (2a) (wherein,
R10 and R1+ represent a lower alkyl group, R5, R
6, R', R8, Y SJ Sm % n % O and p are the same as above. ) The compound represented by the above-formation (8) and the general formula (4) (
The reaction with the compound represented by 6) is carried out in the same manner as the reaction between the compound represented by -formation (3) and the compound represented by the general formula (4) (5) (6) (force). The deacylation reaction by hydrolysis of the compound represented by -formation (9) can be carried out by a conventional method in the presence of a basic catalyst. The reaction between the compound represented by the general formula (5) and the compound represented by the general formula (7) is the reaction between the compound represented by the above-mentioned -formation (3) and the general formula (
4) (5) (6) It can be carried out in the same manner as the reaction with the compounds represented by (7).

After the reaction is completed, the reaction mixture is concentrated, recrystallized, solvent extracted,
``It can be easily separated and purified by conventional means such as column chromatography.

In addition, various binder resins can be used, such as styrene polymers, acrylic polymers, styrene-acrylic copolymers, polyethylene, ethylene-vinyl acetate copolymers, chlorinated polyethylene, polypropylene, and ionomers. Olefin polymers such as polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, epoxy resin, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl Butyral resin, polyether resin, phenol resin, photocurable resin such as epoxy acrylate, etc.
Various polymers can be used, but polymers that increase the sensitivity of the photoreceptor, are compatible with the above-mentioned diamine derivatives, have excellent abrasion resistance and repeatability of the photoreceptor, and have a wide selection of solvents that dissolve the binder resin are preferred. (4,4'-cyclohexylidene diphenyl) carbonate is preferred. The above poly(4,4
'-Cyclohexylidene diphenyl) carbonate allows the use of tetrahydrofuran, methyl ethyl ketone, etc., unlike bisphenol A polycarbonate, which could only use chlorinated solvents such as dichloromethane and monochlorobenzene due to solution stability. It is also possible to use a ketone-based solvent, which is preferable in terms of safety and hygiene, and is easy to handle. In addition, the above poly(44'-
Various types of cyclohexylidene diphenyl) carbonate can be used, for example, those having a degree of polymerization of about 50 to 5,000. Further, the above-mentioned binder resins may be used alone or in combination of two or more.

The ratio of the perylene compound, diamine derivative, and binder resin used is not particularly limited, and can be appropriately selected depending on the desired characteristics of the electrophotographic photoreceptor.
Perylene compound 2 to 100 parts by weight of binder resin
20 parts by weight, preferably 3 to 15 parts by weight, and 40 to 200 parts by weight, preferably 50 to 100 parts by weight of the diamine derivative are used. If the amount of perylene compound and diamine derivative used is less than the above-mentioned amount, not only the sensitivity of the photoreceptor will not be sufficient, but also the residual potential will increase.

Further, if the amount exceeds the above range, the abrasion resistance of the photoreceptor will not be sufficient.

Note that normally, if a large amount of the above perylene compound is used, the positive charging property will not be sufficient, and if a small amount is used, the sensitivity etc. will decrease, but in the electrophotographic photoreceptor of the present invention, a specific perylene compound and a diamine Since it is combined with a derivative, even if the amount of perylene compound is small, it is possible to obtain an electrophotographic photoreceptor that has high sensitivity and surface potential, has a small residual potential, and is excellent in positive chargeability.

Note that even a photoreceptor having a single-layer type photosensitive layer with the above composition and structure has high sensitivity and a small residual potential, and thus exhibits sufficient electrophotographic properties. However, in order to increase the spectral sensitivity, various spectral sensitizers are It is preferable to use phthalocyanine-based compounds which function as charge-generating materials, such as aluminum phthalocyanine, copper phthalocyanine having various crystal forms such as α-type, β-type, γ-type, among others metal-free phthalocyanine and/or titanyl. Preference is given to using phthalocyanines.

The phthalocyanine compound may have an appropriate particle size, but preferably has an average particle size of 0.1 μm or less. The average particle size of metal-free phthalocyanine is 0.1μm
If it exceeds this, the sensitivity of the photoreceptor decreases. In addition, the phthalocyanine compound can be used in an appropriate amount, but the binder resin 10
It is preferable to add 0 to 2 parts by weight relative to 0 parts by weight.

If the amount added exceeds 2 parts by weight, the phthalocyanine compound has spectral sensitivity in a long wavelength region, resulting in insufficient red reproducibility.

The single-layer type photosensitive layer having the above composition may contain other charge-generating materials, charge-transporting materials, etc., as long as the photosensitive properties etc. are not impaired. The above charge generating materials include:
For example, selenium, selenium-tellurium, amorphous silicon, biryllium salts, azo compounds, disazo compounds,
Examples include anthanthrone compounds, indigo compounds, triphenylmethane compounds, threne compounds, toluidine compounds, pyrazoline compounds, other perylene compounds, and quinacridone compounds. In addition, examples of the charge transport material include tetracyanoethylene, 2,
Fluorenone compounds such as 4.7-dolinitro-9-fluorenone, 2,4.8-trinidrothioxanthone,
Nitrated compounds such as dinitroanthracene, succinic anhydride, maleic anhydride, dibromomaleic anhydride, 2.5
-Oxadiazole compounds such as di(4-dimethylaminophenyl)-1,3,4-oxadiazole, 9-(
Styryl compounds such as 4-diethylaminostyryl)anthracene, carbazole compounds such as polyvinylcarbazole, pyrazoline compounds such as 1-phenyl-3-<p-dimethylaminophenyl)pyrazoline, indole compounds, oxazole compounds, isoxazole Examples include nitrogen-containing cyclic compounds such as thiazole-based compounds, thiazole-based compounds, thiadiazole-based compounds, imidazole-based compounds, pyrazole-based compounds, and triazole-based compounds, and fused polycyclic compounds.

In addition, the photosensitive layer includes terphenyl, halonaphthoquinones,
Conventionally known sensitizers such as acenaphthylene, 9-(N, N-
Fluorene compounds such as diphenylhydrazino)fluorene and 9-carbazolyliminofluorene, plasticizers,
It may contain various additives such as antioxidants, anti-deterioration agents such as ultraviolet absorbers, and the like.

The single-layer type photosensitive layer containing the above-mentioned perylene compound, diamine derivative, binder resin, etc. may have an appropriate thickness, but it is preferable to have a thickness of 10 to 50 μl, especially 15 to 2′ll. preferable.

The electrophotographic photoreceptor can be formed by preparing a dispersion of the perylene compound, applying the dispersion to a conductive substrate, and removing the solvent.

The above-mentioned conductive base material may be in the form of a sheet or a drum, and either the base material itself has conductivity or the surface of the base material has conductivity and has sufficient mechanical strength when used. Preferably. As the conductive base material, various conductive materials can be used, such as aluminum, copper,
tin, platinum, gold, silver, vanadium, molybdenum, chromium,
Examples include simple metals such as cadmium, titanium, nickel, palladium, indium, stainless steel, and brass, plastic materials on which the above metals are vapor-deposited or laminated, and glass coated with aluminum iodide, tin oxide, indium oxide, etc. Ru. Among the conductive substrates mentioned above, aluminum, especially aluminum crystal grains, are not present on the surface, preventing the occurrence of black spots and pinholes in copied images, etc., and the above-mentioned perylene compounds, diamine derivatives, etc. In order to improve the adhesion between the photosensitive layer and the base material, anodized aluminum is used, and the alumite layer has a thickness of 5 to 12 μm and a surface roughness of 1.5S.
The following anodized aluminum is preferred.

Further, when preparing the above-mentioned dispersion liquid, various organic solvents can be used depending on the type of binder resin and the like used. The above-mentioned solvents include aliphatic hydrocarbons such as n-hexane, octane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, and chlorobenzene, and dimethyl ether. , diethyl ether,
Ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, esters such as ethyl acetate and methyl acetate, dimethyl formamide, and dimethyl ether.

Various solvents such as tylsulfoxide are exemplified, and one species or a mixture of two or more species may be used. In addition, when preparing the above-mentioned dispersion, a surfactant, a leveling agent, etc. may be used in combination in order to improve dispersibility, coating properties, etc.

Further, the above-mentioned dispersion liquid can be prepared using conventional methods such as a ball mill, a paint shaker, a sand mill, an attritor, an ultrasonic disperser, etc., and the obtained dispersion liquid is applied to the conductive substrate. The electrophotographic photoreceptor of the present invention can be obtained by coating and heating to remove the solvent.

Note that - in order to improve the adhesion between the conductive base material and the photosensitive layer, an undercoat layer may be formed between the conductive base material and the photosensitive layer. The undercoat layer is formed by applying a solution containing a natural or synthetic polymer so that the film thickness after drying is approximately 0.01 to 1 μm.

Further, in order to protect the photosensitive layer, a surface protective layer may be formed on the photosensitive layer. The surface protective layer is made of a binder resin for the pillars or a mixed solution of the binder resin and an additive such as a deterioration inhibitor, and the film thickness after drying is usually 0.1 to 10 μm, preferably 0.2 to 10 μm. It is formed by coating to a thickness of about 5 μm.

In the electrophotographic photoreceptor of the present invention, since the photosensitive layer contains a specific perylene compound and a diamine derivative,
It has excellent positive chargeability and photostability, and although it is a photoreceptor having a single-layer type photosensitive layer, it has high sensitivity and surface potential, and has a small residual potential. Furthermore, since the photoreceptor has a single-layer type photoreceptor layer, an inexpensive electrophotographic photoreceptor can be easily manufactured with high yield. Therefore, the electrophotographic photoreceptor of the present invention is useful as a photoreceptor used in copying machines, laser beam printers, and the like.

<Examples> The present invention will be described in more detail below based on Examples.

Example 1 100 parts by weight of poly(4,4'-cyclohexylidene diphenyl) carbonate (manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name Polycarbonate Z), N,N'-di(3,5-dimethylphenyl)perylene-3 , 4゜9.10-tetracarboxydiimide 8 parts by weight, metal-free phthalocyanine 0.6 parts by weight, 4゜4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocobiphenyl 10
0 parts by weight and a predetermined amount of tetrahydrofuran were charged into a ball mill and mixed and dispersed for 24 hours to prepare a dispersion liquid for a single-layer type photosensitive layer. An electrophotographic photoreceptor having the following was fabricated.

Example 2 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1,
4,4'-bis[N-(3,5-dimethoxyphenyl)
An electrophotographic photoreceptor was produced in the same manner as in Example 1 using -N-phenylaminocopiphenyl.

Example 3 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl in Example 1,
4,4'-bis[N-(3,5-dichlorophenyl)-
Using N-phenylaminocopiphenyl, the above Example 1
An electrophotographic photoreceptor was produced in the same manner as described above.

Example 4 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl in Example 1,
4.4'-bis[N-(3,5-dimethylphenyl)-
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using N-(3-methylphenyl)aminocobiphenyl.

Example 5 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl in Example 1,
4-[N-(2,4-dimethylphenyl)diN-phenylamino] -4'-[N-(3,5-dimethylphenyl)-N-phenylaminocopyphenyl, same as in Example 1 above An electrophotographic photoreceptor was produced.

Example 6 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl in Example 1,
1,4-bis[N-(3,5-dimethylphenyl)-N
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using -phenylaminocobenzene.

Example 7 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl in Example 1,
4,4'-bis[N-(3,5-dimethylphenyl)-
N-phenylaminoco-1゜1', 4/, 1'-
An electrophotographic photoreceptor was produced in the same manner as in Example 1 using terphenyl.

Comparative Example 1 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl of Example 1,
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using N-ethyl-3-carbazolylaldehyde N,N-diphenylhydrazone.

Comparative Example 2 N,N'-di(3,5-dimethylphenyl) of Example 1
The above Example 1 was prepared by using N,N'-di(4-methoxyphenyl)perylene-3,4,9,to-tetracarboxydiimide in place of perylene-3,4,9,10-tetracarboxydiimide. An electrophotographic photoreceptor was produced in the same manner as described above.

Comparative Example 3 N,N'-di(3,5-dimethylphenyl) of Example 1
Instead of perylene-3,4,9,10-tetracarboxydiimide, N,N'-di(2,4°6-drimethylphenyl)perylene-3,4,9°10-tetracarboxydiimide was used. An electrophotographic photoreceptor was produced in the same manner as in Example 1 above.

Comparative Example 4 N,N'-di(3,5-dimethylphenyl) of Example 1
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that dibromoanthanthrone was used in place of perylene-3,4,9,10-tetracarboxydiimide.

Comparative Example 5 N,N'-di(3,5-dimethylphenyl) of Example 1
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that metal-free phthalocyanine was used in place of perylene-3,4,9,10-tetracarboxydiimide.

Comparative Example 6 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl of Example 1,
4-(N,N-diethylamino)benzaldehyde
Example 1 above using N,N-diphenylhydrazone
An electrophotographic photoreceptor was prepared in the same manner as described above.

Comparative Example 7 In place of 4,4′-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl of Example 1,
1-phenyl-3-(4-diethylaminostyryl)-
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using 5-(4-diethylaminophenyl)pyrazoline.

Comparative Example 8 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylaminocopiphenyl of Example 1,
An electrophotographic photoreceptor was produced in the same manner as in Example 1 using polyvinylcarbazole.

For reference, in order to compare the characteristics of the photoreceptor having a laminated photosensitive layer using the charge generation material and charge transport material of Examples 1 to 3 above, the charge generation material and charge transport material used in the above Examples A photoreceptor having a laminated photosensitive layer was produced using a transport material in the following manner.

100 parts by weight of the charge generating material of each of the above examples, 0 parts by weight of metal-free phthalocyanine, per 100 parts by weight of polyvinyl butyral (manufactured by Block Chemical Co., Ltd., trade name Kosuretsuku C)
．． 6 parts by weight and a predetermined amount of benzene were charged into a ball mill and mixed and dispersed for 24 hours to prepare a charge generation layer dispersion. The charge generation layer dispersion was applied to the conductive substrate used in Example 1 to form a charge generation layer to a dry film thickness of 0.5 μm.

In addition, polyester (manufactured by Toyobo Co., Ltd., product name Byron 20)
0) To 100 parts by weight, 70 parts by weight of the charge transporting material used in each of the above examples and a predetermined amount of tetrahydrofuran were stirred and mixed to prepare the coating liquid for the charge transport layer, and the coating liquid for the charge transport layer was prepared. A charge transport layer having a thickness of 18 μm after drying was formed thereon to produce an electrophotographic photoreceptor having a laminated photosensitive layer corresponding to the above example.

Then, in order to examine the charging characteristics and photosensitivity characteristics of the electrophotographic photoreceptors obtained in the above Examples and Comparative Examples, an electrostatic copying paper tester (manufactured by Kawaguchi Electric Co., Ltd., Model 5P-428) was used.
+6 for an electrophotographic photoreceptor having a single-layer type photoreceptor layer. OK
The electrophotographic photoreceptors of each of the Examples and Comparative Examples were charged by performing corona discharge under the conditions of -6.0 KV for electrophotographic photoreceptors having laminated photosensitive layers.

Note that the surface potentials Vs, p, and m of each photoreceptor were measured, and the surface of the photoreceptor was exposed to light using a tungsten lamp with an illuminance of 10 lux, so that the surface potentials Vs, p, were reduced to 1/2. Find the time until half-exposure QEL/2 (
μJ/cot) was calculated. Also, after exposure, 0.
The surface potential after 15 seconds is the residual potential v r,p.

(V).

Table 1 shows the charging characteristics and photosensitive characteristics of each electrophotographic photoreceptor obtained in the above Examples and Comparative Examples.

(Hereafter, blank space) As is clear from Table 1, the photoreceptors of the comparative examples all had insufficient sensitivity and high residual potential.

On the other hand, it was found that all of the electrophotographic photoreceptors of Examples had a small half-life exposure, good sensitivity, and a small residual potential.

In addition, in order to investigate changes in the characteristics of the photoreceptor due to light irradiation,
After irradiating the electrophotographic photoreceptors of Example 1 and Comparative Example 1 with light for 5 minutes using a light source with an illuminance of 1000 lux, the characteristics of each photoreceptor were examined in the same manner as above, and the differences from the original characteristics were determined. The results shown in Table 2 were obtained.

Table 2 As is clear from Table 2 above, the electrophotographic photoreceptor of Comparative Example 1 not only has a significantly increased surface potential and residual potential when exposed to light, but also a significant decrease in sensitivity and insufficient repeatability. It has been found.

On the other hand, it was found that the photoreceptor of Example 1 shows little change in charging characteristics and sensitivity characteristics even when irradiated with light, and exhibits stable characteristics even when used repeatedly.

<Effects of the Invention> As described above, according to the electrophotographic photoreceptor of the present invention, since the photosensitive layer is composed of a specific perylene compound, a diamine derivative, and a binder resin, positive chargeability and photostability are improved. Although it is a photoreceptor with excellent performance and has a single-layer structure,
High sensitivity and surface potential, and low residual potential.

Furthermore, since it is a single-layer type photoreceptor, it has the unique advantage of being easily manufactured with a high yield and being inexpensive.

Claims (1)

[Scope of Claims] 1. A photoreceptor having a single-layer photosensitive layer containing a charge-generating material, a charge-transporting material, and a binder resin, wherein the charge-generating material is perylene represented by the following general formula (1). 1. A photoreceptor for electrophotography, wherein the charge transport material is a diamine derivative represented by the following general formula (2). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1, R^2, R^3, and R^4 represent lower alkyl groups) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (2) (In the formula, R^5, R^6, R^7 and R^8 are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. Y is a hydrogen atom ,
Indicates a lower alkyl group, lower alkoxy group, or halogen atom. l represents an integer of 1 to 3. m, n, o and p
represents an integer from 0 to 2. However, R^5, R^6, R^7
and R^8 shall not be hydrogen atoms at the same time, and at least one of m, n, o and p of R^5, R^6, R^7 and R^8 which are not hydrogen atoms shall be 2. do. ) 2, R^1, R^2, R^3 and R^4 have a carbon number of 1
The electrophotographic photoreceptor according to claim 1, which is an alkyl group of -4. 3. R^5, R^6, R^7 and R^8 are the same or different and are an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms;
The electrophotographic photoreceptor according to claim 1, which is an alkoxy group or a halogen atom. 4. The electrophotographic photoreceptor according to claim 1, wherein Y is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. 5. The electrophotographic photosensitive material according to claim 1, wherein the perylene compound is N,N'-bis(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide. body. 6. The photosensitive layer contains 2 to 20 parts by weight of a perylene compound and 40 to 40 parts by weight of a diamine derivative based on 100 parts by weight of the binder resin.
The electrophotographic photoreceptor according to claim 1, which contains 200 parts by weight. 7. Claim 1 above, wherein the photosensitive layer contains metal-free phthalocyanine or titanyl phthalocyanine
6. The electrophotographic photoreceptor according to item 6.