JPH0520743B2 - - Google Patents

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 the prior art and the invention> In recent years, electrophotographic photoreceptors have been developed that have a greater degree of freedom in functional design.In particular, charge-generating materials that generate electric charges when irradiated with light and electric charges that are generated An electrophotographic photoreceptor has been proposed that has a laminated photosensitive layer in which each function is separated by a charge transporting material. 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)amino]diphenyl are formed on a conductive substrate. An electrophotographic photoreceptor laminated with a charge transport layer (see JP-A-57-144558, JP-A-61-62038), cyanine-based compounds, azo-based compound, N,
N'-bis(2,4,6-trimethylphenyl)
perylene-3,4,9,10-tetracarboxydiimide, N,N'-diphenylperylene-3,4,
9,10-tetracarboxydiimide, N,
Electrophotographic photoreceptors using perylene compounds such as N'-dimethylperylene-3,4,9,10-tetracarboxydiimide (JP-A-57-144556, JP-A-57-144557, Kaisho 60-207148
Publication No. 61-275848, Japanese Patent Publication No. 61-275848
(see Publication No. 132955) have been proposed. In the case of a photoreceptor having the above laminated photosensitive layer,
As described above, since the charge generation function and the charge transport function can be separated by the charge generation layer and the charge transport layer, it is possible to generally obtain a highly sensitive electrophotographic photoreceptor and also to facilitate the selection of photosensitive materials. It has the advantage of being wide. 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 and the layer thickness are as thin as 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. The number of body manufacturing processes increases, workability decreases,
There are problems such as low yield and high cost. 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,
It has advantages such as being able to prevent the generation of ozone, having a wide range of toner materials to choose from, and having 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 described above, in a single layer photosensitive layer, a charge generation material and a charge transport material are mixed in the photosensitive layer, and it is difficult to separate the charge generation function and the charge transport function. Therefore, not only the selection range for each material is 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 photosensitive layer, the photoreceptor having a single-layer photosensitive layer containing a polycyclic aromatic hydrocarbon as a charge-generating material and polyvinylcaribazole as a charge-transporting material ( JP-A No. 56-143438) has been proposed. However, in the case of the above-mentioned photoreceptor, not only does it not have sufficient positive chargeability, but also the drift mobility of polyvinylcarbazole as a charge transport material is small, and the drift mobility shows a large dependence on electric field strength, 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, while taking advantage of the advantages of the single-layer photosensitive layer, it has excellent chargeability and sensitivity, and
In order to provide an electrophotographic photoreceptor with a small residual potential, the applicant first developed N,N'-bis(3,5
-dimethylphenyl)perylene-3,4,9,10
- We proposed a photoreceptor having a single-layer photosensitive layer consisting of a combination of a perylene compound such as tetracarboxydiimide and a hydrazone compound such as N-methyl-3-carbazolylaldehyde N,N-diphenylhydrazone. (Special 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, the above hydrazone compound is 4-(N,N-
Although the degree of photoisomerization caused by light irradiation is smaller than that of diethylamino)benzaldehyde, N,N-diphenylhydrazone, etc., the photostability is still insufficient, so repeated use will reduce sensitivity and increase residual potential. There's a problem. <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. The photoreceptor is characterized in that the charge generating material is a perylene compound represented by the following general formula (1), and the charge transporting material is a diamine derivative represented by the following general formula (2). (In the formula, R ¹ , R ² , R ³ and R ⁴ represent a lower alkyl group) (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, a lower alkyl group, a lower alkoxy group, or a halogen atom. represents a group or a halogen atom. l represents an integer of 1 to 3.
m, n, o and p represent integers of 0 to 2. However, R ⁵ , R ⁶ , R ⁷ and R ⁸ are not hydrogen atoms at the same time, and the above R ⁵ , R ⁶ , R ⁷ which are not hydrogen atoms
and at least one of m, n, o and p in R ⁸ is 2. ) The present invention will be explained in detail below. The electrophotographic photoreceptor of the present invention has a single-layer photosensitive layer, and the photosensitive layer contains a perylene compound represented by the above general formula (1) as a charge-generating material and a charge-transporting material. It contains a diamine derivative represented by the above general formula (2) 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. In addition, as the lower alkoxy group in the above general formula (2), methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-
Examples include alkoxy groups having 1 to 6 carbon atoms such as butoxy, pentyloxy, and hexyloxy groups.
Among the lower alkoxy groups mentioned above, alkoxy groups having 1 to 4 carbon atoms are preferred. In addition, halogen atoms include fluorine, chlorine,
Mention may be made of bromine and iodine atoms. The above substituents R ⁵ , R ⁶ , R ⁷ and R ⁸ may be substituted at any of the o-position, m-position and p-position of the benzene ring, and the substituent Y is the substituent on the benzene ring. may be substituted at an appropriate position. As the perylene compound represented by the above general formula (1), 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-dipentylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,N'-di(3,5-dihexylphenyl)perylene-3,4, Examples include 9,10-tetracarboxydiimide. Among the above perylene compounds, carbon number is 1 to 4
those having an alkyl group of 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. In addition, among the diamine derivatives represented by the above general formula (2), among the p-phenylenediamine derivatives where l=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-phenylamino]benzene, 1,4-bis[N-(2,6-dimethylphenyl)-N-phenylamino]benzene, 1,
4-bis[N-(3,5-dimethylphenyl)-N
-phenylamino]benzene, 1,4-bis[N,N-bis(3,5-dimethylphenyl)amino]benzene, 1-[N,N-di(2,4-dimethylphenyl)amino]-4 -[N,N-di(2,6-dimethylphenyl)amino]benzene,
1-[N,N-di(2,4-dimethylphenyl)
amino]-4-[N,N-di(3,5-dimethylphenyl)amino]benzene, 1-[N,N-di(2,6-dimethylphenyl)amino]-4-[N,
N-di(3,5-dimethylphenyl)amino]benzene, 1-[N,N-di(3,5-dimethylphenyl)amino]-4-(N,N-diphenylamino)-2-methylbenzene , 1,4-bis[N-
(3,5-dimethylphenyl)-N-phenylamino]-2-methylbenzene, 1,4-bis(3,
5-dimethylphenyl)amino]-2-methylbenzene, 1,4-bis[N-(3,5-dimethylphenyl)-N-phenylamino]-2-methoxybenzene, 1,4-bis[N, N-bis(3,5
-dimethylphenyl)amino]-2-methoxybenzene, 1,4-bis[N-(3,5-dimethylphenyl)-N-phenylamino]-2-chlorobenzene, 1,4-bis[N,N- Bis(3,5-
dimethylphenyl)amino]-2-chlorobenzene, 1,4-bis[N-(3,5-dimethylphenyl)-N-phenylamino]-2-bromobenzene, 1,4-bis[N-(2, 4-diethylphenyl)-N-phenylamino]benzene, 1,4
-bis[N-(3,5-diethylphenyl)-N-
phenylamino]benzene, 1,4-bis[N,
N-bis(3,5-diethylphenyl)amino]
Benzene, 1,4-bis[N-(3,5-dipropylphenyl)-N-phenylamino]benzene,
1,4-bis[N,N-bis(3,5-dipropylphenyl)amino]benzene, 1-[N,N-
di(3,5-diisopropylphenyl)amino]
-4-(N,N-diphenylamino)benzene,
1,4-bis[N-(3,5-diisopropylphenyl)-N-phenylamino]benzene, 1,
4-bis[N,N-bis(3,5-diisopropylphenyl)amino]benzene, 1,4-bis[N-(3,5-dibutylphenyl)-N-phenylamino]benzene, 1,4-bis[ N,N-bis(3,5-dibutylphenyl)amino]benzene, 1,4-bis[N-(3,5-diisobutylphenyl)-N-phenylamino]benzene, 1,
4-bis[N,N-bis(3,5-diisobutylphenyl)amino]benzene, 1-[N,N-di(3,5-di-tert-butylphenyl)amino]-
4-(N,N-diphenylamino)benzene, 1,
4-bis[N-(3,5-di-tert-butylphenyl)-N-phenylamino]benzene, 1,4
-bis[N,N-bis(3,5-di-tert-butylphenyl)amino]benzene, 1-[N-(3,
5-dimethylphenyl)-N-phenylamino]-
4-[N-(3,5-diethylphenyl)-N-phenylamino]benzene, 1-[N,N-di(3,
5-dimethylphenyl)amino]-4-[N,N-
di(3,5-diethylphenyl)amino]benzene, 1-[N-(3,5-dimethylphenyl)-N
-phenylamino]-4-[N-(3,5-diisopropylphenyl)-N-phenylamino]benzene, 1-[N,N-di(3,5-dimethylphenyl)amino]-4-[N, N-di(3,5-diisopropylphenyl)amino]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-phenylamino]
Benzene, 1,4-bis[N-(3,5-dimethoxyphenyl)-N-phenylamino]benzene,
1,4-bis[N-(2,6-dimethoxyphenyl)-N-phenylamino]benzene, 1,4-
Bis[N,N-bis(3,5-dimethoxyphenyl)amino]benzene, 1-[N,N-di(2,
4-dimethoxyphenyl)amino]-4-[N,N
-di(2,6-dimethoxyphenyl)amino]benzene, 1-[N,N-di(2,4-dimethoxyphenyl)amino]-4-[N,N-di(3,5-
dimethoxyphenyl)amino]benzene, 1-
[N,N-di(2,6-dimethoxyphenyl)amino]-4-[N,N-di(3,5-dimethoxyphenyl)amino]benzene, 1,4-bis[N-
(3,5-diethoxyphenyl)-N-phenylamino]benzene, 1,4-bis[N,N-di(3,5-diethoxyphenyl)amino]benzene, 1,4-bis[N- (3,5-dipropoxyphenyl)-N-phenylamino]benzene, 1,
4-bis[N,N-di(3,5-dipropoxyphenyl)amino]benzene, 1-[N,N-di(3,5-diisopropoxyphenyl)amino]-
4-(N,N-diphenylamino)benzene, 1,
4-bis[N-(3,5-diisopropoxyphenyl)-N-phenylamino]benzene, 1,4
-bis[N,N-bis(3,5-diisopropoxyphenyl)amino]benzene, 1,4-bis[N-(3,5-dibutoxyphenyl)-N-phenylamino]benzene, 1, 4-bis[N,N-
Bis(3,5-dibutoxyphenyl)amino]benzene, 1,4-bis[N-(3,5-diisobutoxyphenyl)-N-phenylamino]benzene, 1,4-bis[N,N- Bis(3,5-diisobutoxyphenyl)amino]benzene, 1-
[N-(3,5-di-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-phenylamino]benzene, 1,4
-bis[N,N-bis(3,5-di-tert-butoxyphenyl)amino]benzene, 1-[N-
(3,5-dimethoxyphenyl)-N-phenylamino]-4-[N-(3,5-diethoxyphenyl)
-N-phenylamino]benzene, 1-[N,N
-di(3,5-dimethoxyphenyl)amino]-
4-[N,N-di(3,5-diethoxyphenyl)
amino]benzene, 1-[N-(3,5-dimethoxyphenyl)-N-phenylamino]-4-[N-
(3,5-diisopropoxyphenyl)-N-phenylamino]benzene, 1-[N,N-di(3,
5-dimethoxyphenyl)amino]-4-[N,N
-di(3,5-diisopropoxyphenyl)amino]benzene, 1-[N-(3,5-dichlorophenyl)-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-phenylamino]benzene, 1,4-bis[N-(2,
6-dichlorophenyl)-N-phenylamino]
Benzene, 1,4-bis[N-(3,5-dichlorophenyl)-N-phenylamino]benzene,
1-[N,N-di(2,4-dichlorophenyl)
amino]-4-[N,N-di(2,6-dichlorophenyl)amino]benzene, 1-[N,N-di(2,4-dichlorophenyl)amino]-4-[N,
N-di(3,5-dichlorophenyl)amino]benzene, 1-[N,N-di(2,6-dichlorophenyl)amino]-4-[N,N-di(3,5-dichloro phenyl)amino]benzene, 1,4-bis[N-(3,5-dichlorophenyl)-N-phenylamino]-2-chlorobenzene, 1,4-bis[N,N-bis(3,5- dichlorophenyl)
amino]-2-chlorobenzene, 1,4-bis[N-(3,5-dibromophenyl)-N-phenylamino]benzene, 1,4-bis[N,N-bis(3,5-dibromophenyl) ) amino]benzene and the like. Among the benzidine derivatives where l=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-phenylamino]diphenyl,
4,4'-bis[N-(2,6-dimethylphenyl)
-N-phenylamino]diphenyl, 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]diphenyl, 4-[N,N-di(2,
4-dimethylphenyl)amino]-4'-[N,N-
di(2,6-dimethylphenyl)amino]diphenyl, 4-[N,N-di(2,4-dimethylphenyl)amino]-4'-[N,N-di(3,5-dimethylphenyl) enyl)amino]diphenyl, 4-[N,
N-di(2,6-dimethylphenyl)amino]-
4'-[N,N-di(3,5-dimethylphenyl)
amino]diphenyl, 4-[N-(3,5-dimethylphenyl)-N-phenylamino]-4'-(N,
N-diphenylamino)-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-phenylamino]-2,2'-dimethoxydiphenyl,4,4'-bis[N-di(3,5
-dimethylphenyl)amino]-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-phenylamino]diphenyl, 4,4'-bis[N,N-di(3,5-diethylphenyl)amino]diphenyl, 4,4'-bis[N- (3,5-dipropylphenyl)-N-phenylamino]diphenyl, 4,
4'-bis[N,N-di(3,5-dipropylphenyl)amino]diphenyl, 4-[N,N-di(3,5-diisopropylphenyl)amino]-
4'-(N,N-diphenylamino)diphenyl,
4,4'-bis[N-(3,5-diisopropylphenyl)-N-phenylamino]diphenyl, 4,
4'-bis[N,N-di(3,5-diisopropylphenyl)amino]diphenyl, 4,4'-bis[N-(3,5-dibutylphenyl)-N-phenylamino]diphenyl, 4,4' -Bis[N,N-
di(3,5-dibutylphenyl)amino]diphenyl, 4,4'-bis[N-(3,5-diisobutylphenyl)-N-phenylamino]diphenyl,
4,4'-bis[N,N-di(3,5-diisobutylphenyl)amino]diphenyl, 4-[N,N
-di(3,5-di-tert-butylphenyl)amino]-4'-(N,N-diphenylamino)diphenyl, 4,4'-bis[N-(3,5-di-tert-butylphenyl)-N -phenylamino]diphenyl,
4,4'-bis[N,N-di(3,5-di-tert-
butylphenyl)amino]diphenyl, 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-phenylamino]
Diphenyl, 4,4'-bis[N-(2,6-dimethoxyphenyl)-N-phenylamino]diphenyl, 4,4'-bis[N-(3,5-dimethoxyphenyl)-N-phenylamino] diphenyl,
4,4'-bis[N,N-di(3,5-dimethoxyphenyl)amino]diphenyl, 4-[N,N-
di(2,4-dimethoxyphenyl)amino]-
4'-[N,N-di(2,6-dimethoxyphenyl)
amino] diphenyl, 4-[N,N-di(2,4
-dimethoxyphenyl)amino]-4'-[N,N-
di(3,5-dimethoxyphenyl)amino]diphenyl, 4-[N,N-di(2,6-dimethoxyphenyl)amino]-4'-[N,N-di(3,5-
dimethoxyphenyl)amino]diphenyl, 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)amino]-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]-2,2'-dichlorodiphenyl, 4,4'-bis[N-(3,5-diethoxyphenyl)-N-phenylamino]diphenyl, 4,4'-bis[N , N-di(3,5-diethoxyphenyl)amino]diphenyl, 4,
4'-bis[N-(3,5-dipropoxyphenyl)
-N-phenylamino]diphenyl, 4,4'-bis[N,N-di(3,5-dipropoxyphenyl)amino]diphenyl, 4-[N,N-di(3,
5-diisopropoxyphenyl)amino]-4'-
(N,N-diphenylamino)diphenyl, 4,
4'-bis[N-(3,5-diisopropoxyphenyl)-N-phenylamino]diphenyl, 4,
4'-bis[N,N-di(3,5-diisopropoxyphenyl)amino]diphenyl, 4,4'-bis[N-(3,5-dibutoxyphenyl)-N-phenylamino]diphenyl , 4,4′-bis[N,N
-di(3,5-dibutoxyphenyl)amino]diphenyl, 4,4'-bis[N-(3,5-diisobutoxyphenyl)-N-phenylamino]diphenyl, 4,4'-bis[N , N-di(3,5-diisobutoxyphenyl)amino]diphenyl, 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-phenylamino]diphenyl, 4,4'-bis[N,N-di(3,5-di-tert-butoxyphenyl)amino]
Diphenyl, 4-[N,N-di(3,5-dichlorophenyl)amino]-4'-(N,N-diphenylamino)diphenyl, 4,4'-bis[N-(2,
4-dichlorophenyl)-N-phenylamino]
Diphenyl, 4,4'-bis[N-(2,6-dichlorophenyl)-N-phenylamino]diphenyl, 4,4'-bis[N-(3,5-dichlorophenyl)-N-phenylamino] diphenyl, 4,
4'-bis[N,N-di(3,5-dichlorophenyl)amino]diphenyl, 4-[N,N-di(2,
4-dichlorophenyl)amino]-4'-[N,N-
di(2,6-dichlorophenyl)amino]diphenyl, 4-[N,N-di(2,4-dichlorophenyl)amino]-4'-[N,N-di(3,5-dichlorophenyl) enyl)amino]diphenyl, 4-[N,
N-di(2,6-dichlorophenyl)amino]-
4'-[N,N-di(3,5-dichlorophenyl)
amino] diphenyl, 4-[N,N-di(3,5
-dibromophenyl)amino]-4'-(N,N-diphenylamino)diphenyl, 4,4'-bis[N
-(3,5-dibromophenyl)-N-phenylamino]diphenyl, 4,4'-bis[N,N-di(3,5-dibromophenyl)amino]diphenyl, 4,4'-bis[N -(3,5-dichlorophenyl)-N-phenylamino]-2,2'-dichlorodiphenyl, 4,4'-bis[N,N-di(3,5
-dichlorophenyl)amino]-2,2'-dichlorodiphenyl and the like. Further, among the 4,4″-terphenyldiamine derivatives where l=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-phenylamino]-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) amino]-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]-
3,3′,3″-trimethyl-1,1′:4′,1″-terphenyl, 4,4″-bis[N,N-di(3,5-
dimethylphenyl)amino]-3,3′,3″-trimethyl-1,1′:4′,1″-terphenyl, 4,
4″-bis[N-(3,5-dimethylphenyl)-N
-phenylamino]-3,3′,3″-trimethoxy-1,1′:4′,1″-terphenyl, 4,4″-bis[N,N-di(3,5-dimethylphenyl)amino] -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]-3,3′,3″-trichloro-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″-terphenyl, 4,4″-bis[N-(3,5 -diethoxyphenyl)-N-phenylamino]-1,1':4',
1″-terphenyl, 4,4″-bis[N,N-di(3,5-diethoxyphenyl)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-(3,5- diisopropoxyphenyl)-N-phenylamino]-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)amino]-1,1′: 4′,1″-terphenyl, 4,4″-bis[N-(3, 5-diisobutoxyphenyl)-N-phenylamino]-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':4',
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)amino]-4″-[N,N-di(2,6-dichlorophenyl)amino]-1,1′: 4′,1″-terphenyl, 4-[N,N-di(2,4-dichlorophenyl)amino]-4″-[N,N-di(3,5-dichlorophenyl)amino]-1 , 1′:4′,1″-terphenyl, 4-[N,N-di(2,6-dichlorophenyl)amino]-4″-[N,N-di(3,5-
Examples include dichlorophenyl)amino]-1,1':4',1''-terphenyl.The above diamine derivatives may be used alone or in combination of two or more.The above diamine derivatives are
The molecules have good symmetry and are photosensitive, such as conventional 4-(N,N-diethylamino)benzaldehyde N,N-diphenylhydrazone and N-methyl-3-carbazolyl aldehyde N,N-diphenylhydrazone. Not only does it not cause any isomerization reaction upon irradiation and has excellent photostability, but also has high drift mobility and low dependence of drift mobility on electric field strength. More specifically, 4,
4'-bis[N-(3,5-dimethylphenyl)-N
-phenylamino]diphenyl (compound A) as an example, the electric field is 2.0×10 ⁵ V/cm ²
(low electric field) and 5.0×10 ⁵ V/cm ² (high electric field), conventional charge transport materials such as polyvinylcarbazole (compound B), N-ethyl-
3-carbazolyl aldehyde N,N-diphenylhydrazone (compound C) and 1-phenyl-3
-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline (Compound D)
Compared to , the drift mobility is large and the dependence on electric field strength is small, as shown in the table below.

[Table] Diamine derivatives having the above characteristics,
By combining with the perylene compound,
Even if the photoreceptor has a single-layer type photoreceptor layer, a photoreceptor with high sensitivity and a small residual potential can be obtained. The compound represented by the above general formula (2) can be obtained by various methods, for example, by simultaneously combining the compound represented by the following general formula (3) and the compounds represented by general formulas (4) to (7). Alternatively, they can be produced by sequential reactions.

【formula】

【formula】

【formula】

【formula】

[Formula] (In the formula, R ⁵ , R ⁶ , R ⁷ , R ⁸ , Y, l, m, n, o
and p are the same as above. X represents a halogen atom. ) Compounds represented by the above general formula (3) and general formulas (4) to (7)
The reaction with the compound represented by 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, Examples include organic solvents such as N-dimethylformamide, N-methylpyrrolidone, and dimethylsulfoxide. The reaction is usually carried out in the presence of a catalyst such as copper powder, copper oxide, or copper halide, or a basic substance such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate. It is carried out at a temperature of ~250°C. Furthermore, in the compound represented by general formula (2), the substitution positions of substituents R ⁵ , R ⁶ , R ⁷ and R ⁸ are controlled, and the compound represented by general formula (2a) has a symmetrical structure. For example, the compound represented by the following general formula
After obtaining the compound represented by general formula (9) by the reaction of the compound represented by (8) with the compound represented by general formulas (4) and (6), the compound represented by general formula (9) is then obtained. It can be produced by hydrolyzing and deacylating a compound represented by general formula (10) to obtain a compound represented by general formula (10), and then reacting it with a compound represented by general formula (5) (7). can.

【formula】

【formula】 【formula】

【formula】 【formula】

(In the formula, R ¹⁰ and R ¹¹ represent a lower alkyl group,
R ⁵ , R ⁶ , R ⁷ , R ⁸ , Y, l, m, n, o and p
is the same as above. ) The reaction between the compound represented by the above general formula (8) and the compound represented by the general formulas (4)(6) is the reaction between the compound represented by the above general formula (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). general formula
The deacylation reaction by hydrolysis of the compound represented by (9) can be carried out by a conventional method in the presence of a basic catalyst. Furthermore, the reaction between the compound represented by the above general formula (10) and the compound represented by the general formulas (5) and (7) is as follows:
Compounds represented by the above general formula (3) and general formulas (4)(5)(6)(7)
It can be carried out in the same manner as the reaction with the compound represented by. After the reaction is completed, the reaction mixture can be concentrated and easily separated and purified by conventional means such as recrystallization, solvent extraction, column chromatography, etc. 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 copolymers, polyesters, alkyd resins, polyamides, polyurethanes, epoxy resins, etc.
Polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin,
Various polymers can be used, such as ketone resins, polyvinyl butyral resins, polyether resins, phenolic resins, and photocurable resins such as epoxy acrylates, but these polymers can be used to increase the sensitivity of the photoreceptor and to improve compatibility with the diamine derivatives mentioned above. Preferred is poly(4,4'-cyclohexylidene diphenyl) carbonate, which has excellent abrasion resistance and repeatability of the photoreceptor and can be used in a wide range of solvents for dissolving the binder resin. When using the above poly(4,4'-cyclohexylidene diphenyl) carbonate, bisphenol A, which conventionally could only be used with chlorinated solvents such as dichloromethane and monochlorobenzene, due to solution stability etc.
Unlike type polycarbonate, it is also possible to use ketone solvents such as tetrahydrofuran and methyl ethyl ketone, which is preferable from the viewpoint of safety and hygiene, and is easy to handle. In addition, the above poly(4,
There are various types of 4'-cyclohexylidene diphenyl) carbonates, such as those with a degree of polymerization of 50 to
About 5000 can be used. 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 to be used is not particularly limited and can be appropriately selected depending on the desired characteristics of the electrophotographic photoreceptor. The perylene compound is used in an amount of 2 to 20 parts by weight, preferably 3 to 15 parts by weight, and the diamine derivative is used in an amount of 40 to 200 parts by weight, preferably 50 to 100 parts by weight. 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, it is possible to obtain an electrophotographic photoreceptor that has high sensitivity and surface potential even if the amount of perylene compound is small, and has excellent positive chargeability with a small residual potential. 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, so it exhibits sufficient electrophotographic properties, but 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. When the average particle size of the metal-free phthalocyanine exceeds 0.1 μm, the sensitivity of the photoreceptor decreases. Further, the phthalocyanine compound can be used in an appropriate amount, but from 0 to 100 parts by weight based on 100 parts by weight of the above binder resin.
It is preferable to add 2 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. Examples of the charge generating material include selenium, selenium-
Tellurium, amorphous silicon, pyrylium salt,
Examples include azo compounds, disazo compounds, anthanthrone compounds, indigo compounds, triphenylmethane compounds, threne compounds, toluidine compounds, pyrazoline compounds, other perylene compounds, and quinacridone compounds. Further, examples of the charge transport material include tetracyanoethylene, 2,4,7-trinitro-9-
Fluorenone compounds such as fluorenone, 2,
Nitrated compounds such as 4,8-trinitrothioxanthone and dinitroanthracene, succinic anhydride,
Maleic anhydride, dibromomaleic anhydride, 2,
5-di(4-dimethylaminophenyl)-1,3,
Oxadiazole compounds such as 4-oxadiazole, styryl compounds such as 9-(4-diethylaminostyryl)anthracene, carbazole compounds such as polyvinylcarbazole, 1-phenyl-3-(p-dimethylaminophenyl) Nitrogen-containing cyclic compounds such as pyrazoline compounds such as pyrazoline, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, triazole compounds, and fused polycycles Examples include compounds of the above group. In addition, the photosensitive layer may contain conventionally known sensitizers such as terphenyl, halonaphthoquinones, acenaphthylene, etc.
Contains various additives such as fluorene compounds such as 9-(N,N-diphenylhydrazino)fluorene and 9-carbazolyliminofluorene, deterioration inhibitors such as plasticizers, antioxidants, and ultraviolet absorbers. You may do so. The single-layer type photosensitive layer containing the above-mentioned perylene compound, diamine derivative, binder resin, etc. may have an appropriate thickness, but is preferably 10 to 50 μm, particularly 15 μm.
Those having a thickness of ~25 μm are preferred. 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 conductive base material may be in the form of a sheet or a drum, and either the base material itself is conductive or the surface of the base material is conductive and has sufficient mechanical strength when used. Preferably. Various conductive materials can be used as the conductive base material, such as aluminum, copper, tin, platinum,
Single metals such as gold, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless copper, and brass, plastic materials in which the above metals are vapor-deposited or laminated, aluminum iodide, tin oxide, and indium oxide. An example is glass coated with . Among the above conductive base materials, aluminum, especially aluminum crystal grains, are not present on the surface, preventing black spots and pinholes from occurring in copied images, etc., and containing the above perylene compounds and diamine derivatives. In order to improve the adhesion between the photosensitive layer and the substrate, alumite-treated aluminum, especially alumite-treated aluminum with an alumite layer thickness of 5 to 12 μm and a surface roughness of 1.5S or less, is preferable. . 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. Examples of the solvent 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, dimethyl ether, Ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, cyclohexanone, esters such as ethyl acetate, methyl acetate, dimethyl formamide, dimethyl sulfoxide, etc. Examples include solvents, which may be used singly or in combination of two or more. 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 a conventional method, for example, 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 applying the photoreceptor to a solvent and heating it to remove the solvent. Incidentally, 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 about 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 usually formed by drying the various binder resins or a mixture of the binder resin and additives such as anti-deterioration agents to a film thickness of 0.1~
It is formed by coating to a thickness of about 10 μm, preferably about 0.2 to 5 μm. The electrophotographic photoreceptor of the present invention has a photoreceptor layer containing a specific perylene compound and a diamine derivative, so it has excellent positive chargeability and photostability, and is a photoreceptor having a single-layer type photoreceptor layer. However, it has high sensitivity and surface potential, and low 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,
8 parts by weight of 9,10-tetracarboxydiimide, 0.6 parts by weight of metal-free phthalocyanine, 4,4'-
100 parts by weight of bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl and a predetermined amount of tetrahydrofuran are charged into a ball mill and mixed and dispersed for 24 hours to prepare a dispersion for a single-layer photosensitive layer. At the same time, an electrophotographic photoreceptor having a photosensitive layer having a thickness of about 20 μm was prepared by coating it on an alumite-treated aluminum plate. Example 2 4,4'-bis[N-(3,5-dimethoxy) was used instead of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1. An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using N-phenylaminobiphenyl). Example 3 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1, 4,4'-bis[N-(3,5-dichloro An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using N-phenylaminobiphenyl). Example 4 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1, 4,4'-bis[N-(3,5-dimethyl An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using phenyl)-N-(3-methylphenyl)amino]biphenyl. Example 5 4-[N-(2,4-dimethylphenyl)- N-phenylamino]-4'-[N-(3,5-
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using dimethylphenyl)-N-phenylamino]biphenyl. Example 6 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1, 1,4-bis[N-(3,5-dimethylphenyl) An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using (enyl)-N-phenylamino]benzene. Example 7 4,4″-bis[N-(3,5-dimethyl phenyl)-N-phenylamino]-1,1':
An electrophotographic photoreceptor was prepared using 4',1''-terphenyl in the same manner as in Example 1. Comparative Example 1 4,4'-bis[N-(3,5-dimethylphenyl) of Example 1 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that N-ethyl-3-carbazolylaldehyde N,N-diphenylhydrazone was used in place of N-ethyl-3-carbazolyl aldehyde N,N-diphenylhydrazone. Comparative Example 2 In place of N,N'-di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide in Example 1, N,N'-di(4-methoxyphenyl) was used. Example 1 above using perylene-3,4,9,10-tetracarboxydiimide
An electrophotographic photoreceptor was produced in the same manner as described above. Comparative Example 3 N,N'-di(2,4,
6-trimethylphenyl)perylene-3,4,
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using 9,10-tetracarboxydiimide. Comparative Example 4 In place of N,N'-di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide in Example 1, dibromoanthanthrone was used to produce the same result as in Example 1. An electrophotographic photoreceptor was produced in the same manner as described above. Comparative Example 5 Example 1 was prepared using metal-free phthalocyanine in place of N,N'-di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide in Example 1. An electrophotographic photoreceptor was produced in the same manner as described above. Comparative Example 6 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1, 4-(N,N-diethylamino)benzaldehyde N,N-diphenyl was used. An electrophotographic photoreceptor was produced in the same manner as in Example 1 using enylhydrazone. Comparative Example 7 In place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1, 1-phenyl-3-(4-diethylaminostyryl)-5- An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using (4-diethylaminophenyl) prazoline. Comparative Example 8 Using polyvinylcarbazole in place of 4,4'-bis[N-(3,5-dimethylphenyl)-N-phenylamino]biphenyl in Example 1,
An electrophotographic photoreceptor was produced in the same manner as in Example 1 above. For reference, in order to compare the characteristics of a photoconductor having a laminated photosensitive layer using the charge generation materials and charge transport materials of Examples 1 to 3 above, the charge generation materials and charge transport materials used in the above Examples A photoreceptor having a laminated photosensitive layer was produced using the materials in the following manner. To 100 parts by weight of polyvinyl butyral (manufactured by Sekisui Chemical Co., Ltd., trade name Eslec C), 100 parts by weight of the charge-generating material of each of the above examples, 0.6 parts by weight of metal-free phthalocyanine, and a predetermined amount of benzene were charged into a ball mill. A dispersion liquid for a charge generation layer was prepared by time-mixing and dispersion. The charge generation layer dispersion was applied to the conductive substrate used in Example 1 to a dry film thickness of about 0.5 μm to form a charge generation layer. Further, 70 parts by weight of the charge transport material used in each of the above examples and a predetermined amount of tetrahydrofuran were mixed with 100 parts by weight of polyester (manufactured by Toyobo Co., Ltd., trade name: Vylon 200), and the charge transport layer was A photoreceptor for electrophotography having a laminated photosensitive layer corresponding to the above example was prepared by preparing a coating solution and forming a charge transport layer having a thickness of about 18 μm after drying on the charge generation layer. did. In order to investigate 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., SP-
428 type), conduct corona discharge under +6.0KV conditions for electrophotographic photoreceptors with a single-layer type photosensitive layer, and under -6.0KV conditions for electrophotographic photoreceptors with laminated type photoreceptors. The electrophotographic photoreceptors of each of the Examples and Comparative Examples were charged. In addition, while measuring the surface potential Vs.p. (V) of each photoreceptor, the surface of the photoreceptor was exposed to light using a tungsten lamp with an illuminance of 10 lux, and the surface potential Vs.p.
Find the time until p. becomes 1/2, and calculate the halved exposure amount E.
1/2 (μJ/cm ² ) was calculated. Also, after exposure, 0.15
The surface potential after seconds had elapsed was defined as the residual potential Vr.p. (V). Table 1 shows the charging characteristics and photosensitive characteristics of each electrophotographic photoreceptor obtained in the above Examples and Comparative Examples.

【table】

[Table] As is clear from Table 1, the photoreceptor of the comparative example was
In either case, the sensitivity was insufficient and the residual potential was high. In contrast, the electrophotographic photoreceptor of the example
In both cases, it was found that the half-life exposure was small, the sensitivity was good, and the residual potential was small. In order to investigate changes in the characteristics of the photoreceptors due to light irradiation, the electrophotographic photoreceptors of Example 1 and Comparative Example 1 were irradiated with light for 5 minutes using a light source with an illuminance of 1000 lux, and then the characteristics of each photoreceptor were was investigated in the same manner as above to determine the difference from the original characteristics, and the results shown in Table 2 were obtained.

[Table] As is clear from Table 2 above, the electrophotographic photoreceptor of Comparative Example 1 not only significantly increases its surface potential and residual potential but also greatly decreases its sensitivity and does not have sufficient repeatability due to light irradiation. It turned out not to be. 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 a single-layer structure, it has 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 photoconductor having a single-layer photoconductor layer containing a charge-generating material, a charge-transporting material, and a binder resin,
The above charge generating material is a perylene compound represented by the following general formula (1), and the charge transporting material is a perylene compound represented by the following general formula (1).
An electrophotographic photoreceptor characterized by being a diamine derivative represented by (2). (In the formula, R ¹ , R ² , R ³ and R ⁴ represent a lower alkyl group) (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, a lower alkyl group, a lower alkoxy group, or a halogen atom. represents a group or a halogen atom. l represents an integer of 1 to 3.
m, n, o and p represent integers of 0 to 2. However, R ⁵ , R ⁶ , R ⁷ and R ⁸ are not hydrogen atoms at the same time, and the above R ⁵ , R ⁶ , R ⁷ which are not hydrogen atoms
and m, n, o and p of R ⁸ shall be at least 1 or 2. ) 2 The electrophotographic photoreceptor according to claim 1, wherein R ¹ , R ² , R ³ and R ⁴ are alkyl groups having 1 to 4 carbon atoms. 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, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom, according to claim 1 above. photoreceptor for electrophotography. 4 Y is an alkyl group having 1 to 4 carbon atoms, 1 carbon number
The electrophotographic photoreceptor according to claim 1, which is an alkoxy group or a halogen atom of -4. 5 The perylene compound is N,N'-bis(3,
5-dimethylphenyl)perylene-3,4,9,
The electrophotographic photoreceptor according to claim 1, which is 10-tetracarboxydiimide. 6. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer contains 2 to 20 parts by weight of a perylene compound and 40 to 200 parts by weight of a diamine derivative based on 100 parts by weight of a binder resin. 7. The electrophotographic photoreceptor according to claim 1 or 6, wherein the photosensitive layer contains metal-free phthalocyanine or titanyl phthalocyanine.