JPH0830904B2 - Electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Field of Industrial Application> The present invention relates to an electrophotographic photosensitive member that is preferably used in an image forming apparatus such as a copying machine.

<Problems to be Solved by Conventional Techniques and Inventions> In recent years, as a photoreceptor for electrophotography, a photoreceptor having a large degree of freedom in functional design, in particular, a charge generation material that generates a charge by light irradiation, and a generated charge There has been proposed an electrophotographic photoreceptor having a laminated type photosensitive layer in which each function is separated by a transporting charge transporting material. For example, on a conductive substrate,
A charge generation layer containing a squaric acid derivative as a charge generation material, and 4,4′-bis [N-phenyl-N- (3
-Methylphenyl) amino] diphenyl and the like, a charge transport layer containing a diamine derivative, and a photoreceptor for electrophotography (see JP-A-57-144558 and JP-A-61-62038), and the above-mentioned charge Cyanine compounds, azo compounds, N, N'-bis (2,4,6-trimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide, N, N'-diphenyl instead of generating materials Perylene-3,4,9,10-tetracarboxydiimide and N, N'-dimethylperylene-3,
Electrophotographic photoreceptor using a perylene compound such as 4,9,10-tetracarboxydiimide (JP-A-57-144556, JP-A-57-144557, JP-A-60-207148, JP-A-61-275848 and JP-A-61-132955) have been proposed.

In the photoreceptor having the laminated photosensitive layer, as described above, the charge generation function and the generated charge transport function,
Since it can be separated by the charge generation layer and the charge transport layer,
Generally, a high-sensitivity electrophotographic photoreceptor is obtained,
There is an advantage that the selection range of the photosensitive material is wide. However, since the charge transport material is generally a hole transport material, it is difficult to positively charge the photoconductor, and
Since it is difficult to obtain positively charged toner that develops the electrostatic latent image formed on the photoconductor, the selection range of toner materials is narrowed. Further, when negatively charged by corona discharge, ozone is generated, which is not preferable for safety and hygiene. In addition, it is necessary to provide an exhaust passage for exhausting ozone in an image forming apparatus such as a copying machine. Turn into. Furthermore, since the thickness of the charge generation layer is as thin as 1 to 2 μm, not only the charge generation layer has to be formed accurately, but also the charge transport layer has to be formed on the charge generation layer. There are problems that the manufacturing process of the body is increased, the workability is reduced, the yield is lowered, and the cost is increased.

On the other hand, an electrophotographic photosensitive member having a single-layer type photosensitive layer containing a charge generating material, a charge transporting material and a binder resin is also known, and the photosensitive member can be positively charged and can prevent generation of ozone. At the same time, there are advantages that the selection range of the toner material is wide and the manufacturing workability is good. In order to take advantage of such an advantage, when the charge generating material and the charge transporting material used in the laminate type photosensitive layer are applied to the above single layer type photosensitive layer, the photoreceptor having the single layer type photosensitive layer is sufficiently There is a problem that it does not exhibit excellent electrophotographic characteristics. More specifically, unlike the laminated type photosensitive layer, in the single-layer type photosensitive layer, the charge generating material and the charge transporting material are mixed in the photosensitive layer, and the charge generating function and the charge transporting function are provided. Since it is difficult to separate and from each other, not only the selection range of each material is narrow, but also the sensitivity is low and the residual potential is high. Moreover, the electrophotographic characteristics are greatly influenced by the combination of the charge generating material and the charge transporting material. For example, since the diamine derivative as a charge transport material has a small electric field strength dependency on drift mobility, a photoreceptor having a single-layer type photosensitive layer containing the diamine derivative is expected to exhibit a small residual potential. However, when a single-layer type photosensitive layer is formed by combining the above-mentioned various perylene compounds as a charge generating material, the residual potential of the photoreceptor having the single-layer type photosensitive layer is still high, and the sensitivity is not sufficient. There is a problem that it does not exhibit sufficient electrophotographic characteristics.

Further, regarding the photoreceptor having the above-mentioned single-layer type photosensitive layer, the photoreceptor having the single-layer type photosensitive layer containing a polycyclic aromatic hydrocarbon as a charge generating material and polyvinyl carbazole as a charge transporting material (special (Kaisho 56-143438) is proposed.

However, in the above-mentioned photoconductor, not only the positive charging property is insufficient, but also the drift mobility of polyvinylcarbazole as a charge transport material is small, and the drift mobility shows a large electric field strength dependency, so that the residual potential is large. In addition, it has low sensitivity and does not yet exhibit sufficient electrophotographic characteristics.

In view of the above points, while utilizing the advantages of the single-layer type photosensitive layer, while having excellent charging properties and sensitivity, in order to provide a small residual potential electrophotographic photoreceptor, the present applicant, N, N'-bis (3,5-dimethylphenyl) perylene-
Perylene-based compounds such as 3,4,9,10-tetracarboxydiimide and N-methyl-3-carbazolyl aldehyde
We have proposed a photoreceptor having a single-layer type photosensitive layer composed of a combination with a hydrazone compound such as N, N-diphenylhydrazone (Japanese Patent Application No. 62-107780).

However, the above-mentioned hydrazone-based compound still has a large electric field strength dependency on drift mobility, a high residual potential, and insufficient sensitivity. Moreover, although the hydrazone-based compound has a smaller degree of photoisomerization by light irradiation than 4- (N, N-diethylamino) benzaldehyde N, N-diphenylhydrazone and the like, its photostability is still insufficient, and therefore it can be used repeatedly. Therefore, there is a problem that the sensitivity decreases and the residual potential increases.

<Purpose of the Invention> The present invention has been made in view of the above problems, and is excellent in positive charging property and light stability, high in sensitivity and surface potential, small in residual potential, and inexpensive single-layer type photosensitive layer. It is an object of the present invention to provide an electrophotographic photosensitive member having.

<Means and Actions for Solving Problems> To achieve the above object, the electrophotographic photoreceptor of the present invention comprises a single-layer type photosensitive layer containing a charge generating material, a charge transporting material and a binder resin. In the photoreceptor, the charge generation material is a perylene compound represented by the following general formula (1), and the charge transport material is a triphenylamine derivative represented by the following general formula (2). To do.

(In the formula, R ¹ , R ² , R ³ and R ⁴ represent a lower alkyl group) (In the formula, R ⁵ is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkyl group on the phenyl ring, a lower alkoxy group or a diphenylamino group optionally having a halogen atom, a dialkylamino group. R ⁶ and R ⁷ are the same or different and each represents a lower alkyl group, a lower alkoxy group or a diphenylamino group which may have a halogen atom on the phenyl ring.) Explained.

The electrophotographic photoreceptor of the present invention has a single-layer type photosensitive layer, and the photosensitive layer comprises a perylene compound represented by the general formula (1) as a charge generating material and a charge transporting material. The triphenylamine derivative represented by the above general formula (2) and a binder resin.

Examples of the lower alkyl group in the general formulas (1) and (2) include an alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and hexyl groups. It is illustrated. Among the above lower alkyl groups, alkyl groups having 1 to 4 carbon atoms are preferable.

Examples of the lower alkoxy group in the general formula (2) include alkoxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy groups. To be done. Among the above lower alkoxy groups, an alkoxy group having 1 to 4 carbon atoms is preferable.

Examples of the halogen atom include a fluorine, chlorine, bromine and iodine atom.

Examples of the dialkylamino group include dimethylamino, diethylamino, methylethylamino, dipropylamino,
Diisopropylamino, dibutylamino, diisobutylamino, di-tert-butylamino, dipentylamino,
A dialkylamino group having an alkyl group having 1 to 6 carbon atoms such as a dihexylamino group is exemplified. Of the above dialkylamino groups, a dialkylamino group having an alkyl group having 1 to 4 carbon atoms is preferable.

When R ⁵ , R ⁶ and R ⁷ are diphenylamino groups having a substituent, the substituent is the o-position of the phenyl ring, m
It may have a substituent at either the -position or the p-position.

Examples of the perylene-based compound represented by the 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-dipentylphenyl) perylene-3,4,9,10-
Tetracarboxydiimide, N, N'-di (3,5-di (3,5
Examples include -dihexylphenyl) perylene-3,4,9,10-tetracarboxydiimide.

Among the above-mentioned perylene compounds, those having an alkyl group having 1 to 4 carbon atoms, among which N, N'-di (3,5-dimethylphenyl) perylene-3,4,9,10-tetracarboxy Diimide is preferred. The above perylene compounds may be used alone or in combination of two or more.

In the compound represented by the general formula (2),
Among triphenylamine derivatives in which R ⁵ is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, preferred compounds include, for example, 4,4′-bis (N, N-diphenylamino) triphenylamine, 4,4'-bis (N, N-diphenylamino) -4 "-methyltriphenylamine, 4,4'-bis (N, N-diphenylamino)-
4 ″ -ethyltriphenylamine, 4,4′-bis (N, N-
Diphenylamino) -4 "-propyltriphenylamine, 4,4'-bis (N, N-diphenylamino) -4" -isopropyltriphenylamine, 4,4'-bis (N, N-diphenylamino)- 4 ″ -isobutyltriphenylamine, 4,4′-bis (N, N-diphenylamino) -4 ″ -te
rt-Butyltriphenylamine, 4,4'-bis (N, N-diphenylamino) -4 "-methoxytriphenylamine, 4,4'-bis (N, N-diphenylamino) -4" -ethoxytri Phenylamine, 4,4'-bis (N, N-diphenylamino) -4 "-propoxytriphenylamine,
4,4'-bis (N, N-diphenylamino) -4 "-isopropoxytriphenylamine, 4,4'-bis (N, N-diphenylamino) -4" -isobutoxytriphenylamine, 4, 4'-bis (N, N-diphenylamino) -4 "-te
rt-Butoxytriphenylamine, 4,4'-bis (N, N-
Diphenylamino) -4 ″ -chlorotriphenylamine, 4,4′-bis (N, N-diphenylamino) -4 ″ -bromotriphenylamine, 4- [N- (4-mephenyl) -N-phenylamino ] -4 '-(N, N-Diphenylamino) triphenylamine, 4- [N- (4-ethylphenyl) -N-phenylamino] -4'-(N, N-
Diphenylamino) triphenylamine, 4- [N-
(4-Isopropylphenyl) -N-phenylamino]
-4 '-(N, N-diphenylamino) triphenylamine, 4- [N- (4-isobutylphenyl) -N-phenylamino] -4'-(N, N-diphenylamino) triphenylamine, 4 -[N- (4-methoxyphenyl)
-N-phenylamino] -4 '-(N, N-diphenylamino) triphenylamine, 4- [N- (4-ethoxyphenyl) -N-phenylamino] -4'-(N, N-diphenylamino) ) Triphenylamine, 4- [N- (4
-Isopropoxyphenyl) -N-phenylamino]-
4 '-(N, N-diphenylamino) triphenylamine, 4- [N- (4-isobutoxyphenyl) -N-phenylamino] -4'-(N, N-diphenylamino) triphenylamine, 4 -[N- (4-chlorophenyl)
-N-phenylamino] -4 '-(N, N-diphenylamino) triphenylamine, 4- [N- (4-bromophenyl) -N-phenylamino] -4'-(N, N-diphenylamino) ) Triphenylamine, 4,4'-bis [N
-(2-methylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (3-methylphenyl) -N-phenylamino] triphenylamine, 4,
4'-bis [N- (4-methylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N-
(2-Ethylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (3-ethylphenyl) -N-phenylamino] triphenylamine, 4,
4'-bis [N- (4-ethylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N-
(4-Isopropylphenyl) -N-phenylamino]
Triphenylamine, 4,4'-bis [N- (4-isobutylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4-tert-butylphenyl) -N-phenyl Amino] triphenylamine, 4,
4'-bis [N- (2-methoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N-
(3-methoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4-methoxyphenyl) -N-phenylamino] triphenylamine,
4,4'-bis [N- (2-ethoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N
-(3-Ethoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4-ethoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N -(4-isopropoxyphenyl) -N-phenylamino] triphenylamine, 4,
4'-bis [N- (4-isobutoxyphenyl) -N-
Phenylamino] triphenylamine, 4,4'-bis [N- (4-tert-butoxyphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (2
-Chlorophenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (3-chlorophenyl)
-N-phenylamino] triphenylamine, 4,4'-
Bis [N- (4-chlorophenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4-bromophenyl) -N-phenylamino] triphenylamine, 4- [N- ( 2-Methylphenyl) -N-phenylamino] -4 '-[N- (3-methylphenyl) -N
-Phenylamino] triphenylamine, 4- [N-
(2-Methylphenyl) -N-phenylamino] -4 '
-[N- (4-methylphenyl) -N-phenylamino] triphenylamine, 4- [N- (3-methylphenyl) -N-phenylamino] -4 '-[N- (4-methylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (2-methylphenyl) -N
-Phenylamino] -4 "-methyltriphenylamine, 4,4'-bis [N- (3-methylphenyl) -N-
Phenylamino] -4 "-methyltriphenylamine,
4,4′-bis [N- (4-methylphenyl) -N-phenylamino] -4 ″ -methyltriphenylamine, 4,
4'-bis [N- (2-ethylphenyl) -N-phenylamino] -4 "-methyltriphenylamine, 4,4 '
-Bis [N- (3-ethylphenyl) -N-phenylamino] -4 "-methyltriphenylamine, 4,4'-bis [N- (4-ethylphenyl) -N-phenylamino] -4" -Methyltriphenylamine, 4,4'-bis [N- (4-isopropylphenyl) -N-phenylamino] -4 "-methyltriphenylamine, 4,4'-bis [N- (4-isobutylphenyl) ) -N-Phenylamino] -4 "-methyltriphenylamine, 4,4'-bis [N- (4-tert-butylphenyl) -N-phenylamino] -4" -methyltriphenylamine, 4, 4'-
Bis [N- (4-ethylphenyl) -N-phenylamino] -4 ″ -ethyltriphenylamine, 4,4′-bis [N- (2-methoxyphenyl) -N-phenylamino] -4 ″- Methoxytriphenylamine, 4,4'-bis [N- (3-methoxyphenyl) -N-phenylamino] -4 "-methoxytriphenylamine, 4,4'-bis [N- (4-methoxyphenyl) -N-phenylamino] -4 "-methoxytriphenylamine, 4,4'-bis [N- (4-ethoxyphenyl) -N-phenylamino] -4" -methoxytriphenylamine, 4,4'- Bis [N- (4-isopropoxyphenyl) -N-phenylamino] -4 ″ -methoxytriphenylamine, 4,
4'-bis [N- (4-isobutoxyphenyl) -N-
Phenylamino] -4 ″ -methoxytriphenylamine, 4,4′-bis [N- (4-tert-butoxyphenyl) -N-phenylamino] -4 ″ -methoxytriphenylamine, 4,4′-bis [N- (4-methoxyphenyl) -N-phenylamino] -4 "-ethoxytriphenylamine, 4,4'-bis [N- (4-ethoxyphenyl) -N-phenylamino] -4" --- Ethoxytriphenylamine, 4,4'-bis [N- (4-methoxyphenyl) -N-phenylamino] -4 "-methyltriphenylamine, 4,4'-bis [N- (4-methoxyphenyl) -N-phenylamino] -4 "-ethyltriphenylamine, 4,4'-bis [N- (2-chlorophenyl)
-N-phenylamino] -4 "-chlorotriphenylamine, 4,4'-bis [N- (3-chlorophenyl) -N
-Phenylamino] -4 "-chlorotriphenylamine, 4,4'-bis [N- (4-chlorophenyl) -N-
Phenylamino] -4 "-chlorotriphenylamine,
4,4′-bis [N- (2-bromophenyl) -N-phenylamino] -4 ″ -chlorotriphenylamine, 4,
4'-bis [N- (3-bromophenyl) -N-phenylamino] -4 "-bromotriphenylamine, 4,4 '
-Bis [N- (4-bromophenyl) -N-phenylamino] -4 "-bromotriphenylamine, 4,4'-bis [N- (4-chlorophenyl) -N-phenylamino] -4"- Methyltriphenylamine, 4,4'-bis [N- (4-chlorophenyl) -N-phenylamino]
-4 "-methoxytriphenylamine, 4- [N- (2
-Methylphenyl) -N-phenylamino] -4'-
[N- (3-methylphenyl) -N-phenylamino]
-4 ″ -methyltriphenylamine, 4- [N- (2-
Methylphenyl) -N-phenylamino] -4 '-[N
-(4-Methylphenyl) -N-phenylamino]-
4 "-methyltriphenylamine, 4- [N- (3-methylphenyl) -N-phenylamino] -4 '-[N-
(4-Methylphenyl) -N-phenylamino] -4 ″
-Methyltriphenylamine, 4- [N- (3-methylphenyl) -N-phenylamino] -4 '-[N- (4
-Methylphenyl) -N-phenylamino] -4 "-ethyltriphenylamine, 4- [N- (2-ethylphenyl) -N-phenylamino] -4 '-[N- (4-ethylphenyl)- N-phenylamino] -4 ″ -methyltriphenylamine, 4- [N-3-ethylphenyl)
-N-phenylamino] -4 '-[N- (4-ethylphenyl) -N-phenylamino] -4 "-methyltriphenylamine, 4- [N- (3-ethylphenyl) -N
-Phenylamino] -4 '-[N- (4-ethylphenyl) -N-phenylamino] -4 "-ethyltriphenylamine, 4- [N- (2-methoxyphenyl) -N-
Phenylamino] -4 ′-[N- (3-methoxyphenyl2-N-phenylamino] -4 ″ -methoxytriphenylamine, 4- [N- (2-methoxyphenyl) -N
-Phenylamino] -4 '-[N- (4-methoxyphenyl) -N-phenylamino] -4 "-methoxytriphenylamine, 4- [N- (3-methoxyphenyl)-
N-phenylamino] -4 ′-[N- (4-methoxyphenyl) -N-phenylamino] -4 ″ -methoxytriphenylamine, 4- [N- (2-ethoxyphenyl)
-N-phenylamino] -4 '-[N- (3-ethoxyphenyl) -N-phenylamino] -4 "-methoxytriphenylamine, 4- [N- (2-chlorophenyl)
-N-phenylamino] -4 '-[N- (3-chlorophenyl-N-phenylamino] -4 "-chlorotriphenylamine, 4- [N- (2-chlorophenyl) -N-
Phenylamino] -4 '-[N- (4-chlorophenyl) -N-phenylamino] -4 "-chlorotriphenylamine, 4- [N- (3-chlorophenyl) -N-phenylamino] -4'- [N- (4-chlorophenyl)
Examples include —N-phenylamino] -4 ″ -chlorotriphenylamine and the like.

Further, among the triphenylamine derivatives in which R ⁵ is a lower alkyl group, a lower alkoxy group, or a diphenylamino group which may have a halogen atom on the phenyl ring, preferable compounds include, for example, 4,4 ′ , 4 "-tris (N, N-diphenylamino) triphenylamine, 4,
4 ', 4 "-Tris [N- (2-methylphenyl) -N-
Phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine, 4,4', 4" -tris [N-
(4-Methylphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (2-ethylphenyl) -N-phenylamino] triphenylamine, 4,4', 4 ″ -Tris [N- (3-ethylphenyl)
-N-phenylamino] triphenylamine, 4,4 ',
4 "-tris [N- (4-ethylphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4" -tris [N- (4-propylphenyl) -N-phenylamino] triphenylamine , 4,4 ', 4 "-Tris [N-
(4-Isopropylphenyl) -N-phenylamino]
Triphenylamine, 4,4 ', 4 "-tris [N- (4-
Butylphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (4-isobutylphenyl) -N-phenylamino] triphenylamine,
4,4 ', 4 "-tris [N- (4-tert-butylphenyl) -N-phenylamino] triphenylamine, 4,
4 ', 4 "-Tris [N- (2-methoxyphenyl) -N
-Phenylamino] triphenylamine, 4,4 ', 4 "-
Tris [N- (3-methoxyphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -Tris [N
-(4-Methoxyphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (2-ethoxyphenyl) -N-phenylamino] triphenylamine, 4,4', 4 "-tris [N- (3-ethoxyphenyl) -N-phenylamino] triphenylamine, 4,
4 ', 4 "-Tris [N- (4-ethoxyphenyl) -N
-Phenylamino] triphenylamine, 4,4 ', 4 "-
Tris [N- (4-propoxyphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4 "-Tris [N- (4-isopropoxyphenyl) -N-phenylamino] triphenylamine, 4 , 4 ', 4 "-Tris [N
-(4-Butoxyphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (4-isobutoxyphenyl) -N-phenylamino] triphenylamine, 4,4' , 4 "-Tris [N- (4-tert-butoxyphenyl) -N-phenylamino] triphenylamine, 4,4 ', 4" -Tris [N- (2-chlorophenyl) -N-phenylamino] tri Phenylamine, 4,
4 ', 4 "-Tris [N- (3-chlorophenyl) -N-
Phenylamino] triphenylamine, 4,4 ', 4 "-tris [N- (4-chlorophenyl) -N-phenylamino] triphenylamine, 4,4', 4" -tris [N-
(4-Bromophenyl) -N-phenylamino] triphenylamine, 4- [N- (2-methylphenyl) -N
-Phenylamino] -4 '-[N- (3-methylphenyl) -N-phenylamino] -4 "-[N- (4-methylphenyl) -N-phenylamino] triphenylamine, 4,4' -Bis [N- (2-methylphenyl) -N-
Phenylamino] -4 "-[N- (3-methylphenyl) -N-phenylamino] triphenylamine, 4,
4'-bis [N- (2-methylphenyl) -N-phenylamino] -4 "-[N- (4-methylphenyl) -N
-Phenylamino] triphenylamine, 4,4'-bis [N- (3-methylphenyl) -N-phenylamino]
-4 "-[N- (2-methylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4
-Methylphenyl) -N-phenylamino] -4 "-
[N- (2-methylphenyl) -N-phenylamino]
Triphenylamine, 4,4'-bis [N- (3-methylphenyl) -N-phenylamino] -4 "-[N- (4
-Methylphenyl) -N-phenylamino] triphenylamine, 4,4'-bis [N- (4-methylphenyl)
-N-phenylamino] -4 "-[N- (3-methylphenyl) -N-phenylamino] triphenylamine,
4,4 ', 4 "-Tris [N, N-di (2-methylphenyl) amino] triphenylamine, 4,4', 4" -Tris [N, N-
Di (3-methylphenyl) amino] triphenylamine, 4,4 ′, 4 ″ -tris [N, N-di (4-methylphenyl) amino] triphenylamine, 4- [N- (2-methylphenyl) ) -N- (3-Methylphenyl) amino]
-4 '-[N- (2-methylphenyl) -N- (4-methylphenyl) amino] -4 "-[N- (3-methylphenyl) -N- (4-methylphenyl) amino] triphenyl Amine, 4- [N, N-di (2-methylphenyl)
Amino] -4 '-[N- (2-methylphenyl) -N-
(3-Methylphenyl) amino] -4 ″-[N- (2-
Methylphenyl) -N- (4-methylphenyl) amino] triphenylamine, 4- [N, N-di (2-methylphenyl) amino] -4 '-[N, N-di (4-methylphenyl) Amino] -4 "-[N- (3-methylphenyl) -N- (4-methylphenyl) amino] triphenylamine, 4- [N, N-di (2-methylphenyl) amino] 4 ', 4 ″ -Bis [N- (2-methylphenyl) -N
-(4-Methylphenyl) amino] triphenylamine, 4- [N, N-di (2-methylphenyl) amino]-
4 '-[N, N-di (4-methylphenyl) amino]-
4 "-[N- (3-methylphenyl) -N- (4-methylphenyl) amino] triphenylamine, 4- [N, N
-Di (2-methylphenyl) amino] -4 '-[N-
(2-methylphenyl) -N- (4-methylphenyl)
Amino] -4 "-[N- (3-methylphenyl) -N-
(4-methylphenyl) amino] triphenylamine,
4- [N, N-di (3-methylphenyl) amino] -4 '
-[N- (2-methylphenyl) -N- (4-methylphenyl) amino] -4 "-[N- (3-methylphenyl) -N- (4-methylphenyl) amino] triphenylamine, 4 , 4 ', 4 "-Tris [N, N-di (2-methoxyphenyl) amino] triphenylamine, 4,4', 4"-
Tris [N, N-di (3-methoxyphenyl) amino] triphenylamine, 4,4 ′, 4 ″ -Tris [N, N-di (4-
Methoxyphenyl) amino] triphenylamine, 4,
4 ', 4 "-tris [N, N-di (2-chlorophenyl) amino] triphenylamine, 4,4', 4" -tris [N, N-di (3-chlorophenyl) amino] triphenylamine,
Examples include 4,4 ′, 4 ″ -tris [N, N-di (4-chlorophenyl) amino] triphenylamine.

Further, among the triphenylamine derivatives in which R ⁵ is a dialkylamino group, preferred compounds include, for example, 4,4′-bis (N, N-diphenylamino) -4 ″ -dimethylaminotriphenylamine, 4 , 4'-bis (N, N-
Diphenylamino) -4 ″ -diethylaminotriphenylamine, 4,4′-bis (N, N-diphenylamino)-
4 ″ -dipropylaminotriphenylamine, 4,4′-
Bis (N, N-diphenylamino) -4 ″ -diisopropylaminotriphenylamine, 4,4′-bis (N, N-diphenylamino) -4 ″ -dibutylaminotriphenylamine, 4,4′-bis ( N, N-diphenylamino) -4 ″-
Diisobutylaminotriphenylamine, 4,4'-bis (N, N-diphenylamino) -4 "-di-tert-butylaminotriphenylamine, 4,4'-bis [N, N-di (2
-Methylphenyl) amino] -4 "-dimethylaminotriphenylamine, 4,4'-bis [N, N-di (3-methylphenyl) amino] -4" -dimethylaminotriphenylamine, 4,4 ' -Bis [N, N-di (4-methylphenyl) amino] -4 "-dimethylaminotriphenylamine, 4,4'-bis [N- (4-methylphenyl) -N-
Phenylamino] -4 ″ -dimethylaminotriphenylamine, 4- [N- (2-methylphenyl) -N-phenylamino] -4 ′-[N- (3-methylphenyl)-
N-phenylamino] -4 ″ -dimethylaminotriphenylamine, 4- [N- (2-methylphenyl) -N-
Phenylamino] -4 ′-[N- (4-methylphenyl) -N-phenylamino] -4 ″ -dimethylaminotriphenylamine, 4- [N- (3-methylphenyl)
-N-phenylamino] -4 '-[N- (4-methylphenyl) -N-phenylamino] -4 "-dimethylaminotriphenylamine, 4,4'-bis [N, N-di (2- Methoxyphenyl) amino] -4 ″ -dimethylaminotriphenylamine, 4,4′-bis [N, N-di (3-methoxyphenyl) amino] -4 ″ -dimethylaminotriphenylamine, 4,4′- Bis [N, N-di (4-methoxyphenyl) amino] -4 ″ -dimethylaminotriphenylamine, 4,4′-bis [N- (4-methoxyphenyl) -N
-Phenylamino] -4 "-dimethylaminotriphenylamine, 4- [N- (2-methoxyphenyl) -N-
Phenylamino] -4 '-[N- (3-methoxyphenyl) -N-phenylamino] -4 "-dimethylaminotriphenylamine, 4- [N- (2-methoxyphenyl) -N-phenylamino]- 4 '-[N- (4-methoxyphenyl) -N-phenylamino] -4 "-dimethylaminotriphenylamine, 4- [N- (3-methoxyphenyl) -N-phenylamino] -4'-[ N-
(4-Methoxyphenyl) -N-phenylamino]-
4 "-dimethylaminotriphenylamine, 4,4'-bis [N, N-di (2-chlorophenyl) amino] -4"-
Dimethylaminotriphenylamine, 4,4'-bis [N, N
-Di (3-chlorophenyl) amino] -4 "-dimethylaminotriphenylamine, 4,4'-bis [N, N-di (4
-Chlorophenyl) amino] -4 "-dimethylaminotriphenylamine, 4,4'-bis [N- (4-chlorophenyl) -N-phenylamino] -4" -dimethylaminotriphenylamine, 4- [N- (2-chlorophenyl) -N-phenylamino] -4 ′-[N- (3-chlorophenyl) -N-phenylamino] -4 ″ -dimethylaminotriphenylamine, 4- [N- (2-chlorophenyl-N -Phenylamino] -4 '-[N- (4-chlorophenyl) -N-phenylamino] -4 "-dimethylaminotriphenylamine, 4- [N- (3-chlorophenyl) -N-phenylamino] -4 ′-[N- (4
Examples include -chlorophenyl) -N-phenylamino] -4 "-dimethylaminotriphenylamine.

The above triphenylamine derivatives may be used alone or in combination of two or more. The above-mentioned triphenylamine derivative has good molecular symmetry, and it is a conventional 4- (N, N-diethylamino) benzaldehyde N, N-diphenylhydrazone or N-methyl-3-carbazolylaldehyde.
Unlike N, N-diphenylhydrazone, light irradiation does not cause an isomerization reaction and the like, and not only has excellent photostability, but also has a large drift mobility and a small electric field strength dependency on the drift mobility. More specifically, 4,
Taking 4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (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. ^{When a 2} (high electric field) is applied, conventional charge transport materials such as polyvinylcarbazole (Compound B), N-ethyl-3
-Carbazolyl aldehyde Compared to N, N-diphenylhydrazone (Compound C) and 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazolin (Compound D), As shown, the drift mobility is large and the electric field strength dependency is small.

By combining the triphenylamine derivative having the above characteristics and the perylene-based compound,
Even a photoreceptor having a single-layer type photosensitive layer can be obtained with high sensitivity and small residual potential.

The compound represented by the general formula (2) can be produced by various methods. The compound in which R ⁵ is a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom is, for example, a compound represented by the following general formula (3) and a compound represented by the general formulas (4) and (5). Can be produced by reacting simultaneously or sequentially.

(In the formula, R ⁵ ′ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. R ⁸ and R ⁹ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group and a halogen atom. X is a halogen atom. The compound represented by the general formula (3) and the general formula (4),
The reaction with the compound represented by (5) is usually carried out in an organic solvent, and any solvent can be used as long as it does not adversely affect the reaction, and examples thereof include nitrobenzene, dichlorobenzene and quinoline. , N-N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like are exemplified. The reaction is usually carried out in the presence of a catalyst such as copper powder, copper oxide, copper halide, etc., and a basic substance such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, etc. It is carried out at a temperature of ~ 250 ° C.

Further, in the compound represented by the general formula (2), substitution
When R ⁵ is a lower alkyl group, a lower alkoxy group, a diphenylamino group having a halogen atom or a dialkylamino group on the phenyl ring, for example, a compound represented by the following general formula (6) and a general formula (7) It can be produced by reacting the compound represented by and the compound represented by the general formula (4) or (5) simultaneously or sequentially.

(In the formula, R ¹⁰ represents a lower alkyl group, a lower alkoxy group, a phenyl group having a halogen atom, or an alkyl group,
R ⁸ , R ⁹ and X are the same as above. ) The compound represented by the general formula (6) and the general formula (7)
(4) The reaction with the compound represented by (5) can be carried out in the same manner as the reaction between the compound represented by the general formula (3) and the compound represented by the general formula (4) or (5). it can.

After completion of the reaction, the reaction mixture can be concentrated and easily separated and purified by a conventional means such as recrystallization, solvent extraction, column chromatography and the like.

Further, as the binder resin, various ones, for example,
Styrene polymers, acrylic polymers, styrene-acrylic copolymers, polyethylene, ethylene-vinyl acetate copolymers, olefin polymers such as chlorinated polyethylene, polypropylene and ionomers, polyvinyl chloride, vinyl chloride-acetic acid Vinyl copolymer, polyester, alkyd resin, polyamide, polyurethane, epoxy resin,
Polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin,
Various polymers such as polyvinyl butyral resin, polyether resin, phenyl resin, and photocurable resin such as epoxy acrylate can be used, but the sensitivity of the photoconductor is increased and the compatibility with the above-mentioned triphenylamine derivative, etc. Poly (4,4'-cyclohexylidenediphenyl) carbonate, which has excellent wear resistance and repetitive properties of the body and has a wide selection range of solvents for dissolving the binder resin, is preferable. When poly (4,4′-cyclohexylidenediphenyl) carbonate is used, tetrahydrofuran is different from bisphenol A type polycarbonate, which has conventionally been able to use only chlorine-based solvents such as dichloromethane and monochlorobenzene from the viewpoint of solution stability. Since a ketone solvent such as methyl ethyl ketone can also be used, it is preferable in terms of stable hygiene and is easy to handle. As the poly (4,4'-cyclohexylidenediphenyl) carbonate, various ones, for example, those having a degree of polymerization of about 50 to 5,000 can be used. The binder resin is used alone or in combination of two or more.

The use ratio of the perylene-based compound, the triphenylamine derivative and the binder resin is not particularly limited and can be appropriately selected depending on the desired characteristics of the electrophotographic photoreceptor, and the like. 2 to 20 parts by weight, preferably 3 to 15 parts by weight, and 40 to 200 parts by weight of the triphenylamine derivative, preferably 50 to 100 parts by weight.
Used up to 100 parts by weight. If the amount of the perylene-based compound and the triphenylamine derivative used is less than the above-mentioned amount, not only the sensitivity of the photoreceptor is insufficient but also the residual potential becomes large. On the other hand, if it exceeds the above range, the abrasion resistance of the photoconductor becomes insufficient.

Usually, when the above-mentioned perylene-based compound is used in a large amount, the normal voltage becomes insufficient, and when it is a small amount, the sensitivity and the like decrease, but in the electrophotographic photoreceptor of the present invention, the specific perylene-based compound and triphenyl compound are used. Since it is combined with an amine derivative, it is possible to obtain an electrophotographic photoreceptor having a high sensitivity and a high surface potential and a small residual potential and an excellent positive charging property even if the amount of the perylene compound is small.

It should be noted that even a photoreceptor having a single-layer type photosensitive layer having the above composition and structure has high sensitivity and a small residual potential, and thus exhibits sufficient electrophotographic characteristics, but various spectral sensitizers are used to enhance spectral sensitivity. It is preferable to use a phthalocyanine compound that functions as a charge generating material, for example, α-type, β-type
It is preferable to use aluminum phthalocyanine and copper phthalocyanine having various crystal types such as γ-type and γ-type, and among them, metal-free phthalocyanine and / or titanyl phthalocyanine.

The phthalocyanine compound may have an appropriate particle size, but an average particle size of 0.1 μm or less is preferable. The average particle size of metal-free phthalocyanine is 0.1 μm
If it exceeds the range, the sensitivity of the photoreceptor is lowered. 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 to 0 parts by weight. If the amount added exceeds 2 parts by weight, the phthalocyanine compound has spectral sensitivity in the long wavelength region, and red reproducibility becomes insufficient.

The single-layer type photosensitive layer having the above composition may use other charge generating material, charge transporting material or the like within a range that does not impair the photosensitive characteristics and the like. Examples of the charge generation material include selenium, selenium-tellurium, amorphous silicon, pyrylium salts, azo compounds, disazo compounds, ansanthrone compounds, isodigo compounds, triphenylmethane compounds, threnic compounds, toluidine compounds. Examples thereof include compounds, pyrazoline compounds, other perylene compounds, and quinacridone compounds. Examples of the charge transport material include tetracyanoethylene, fluorenone compounds such as 2,4,7-trinitro-9-fluorenone, 2,4,8-trinitrothioxanthone,
Nitro compounds such as dinitroanthracene, succinic anhydride, maleic anhydride, dibromomaleic anhydride, 2,5-
Oxadiazole compounds such as di (4-dimethylaminophenyl) -1,3,4-oxadiazole, styrene compounds such as 9- (4-diethylaminostyrin) anthracene, carbazole compounds such as polyvinylcarbazole, Pyrazoline compounds such as 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds,
Examples thereof include nitrogen-containing cyclic compounds such as imidazole compounds, pyrazole compounds, and triazole compounds, condensed polycyclic compounds, and the like.

The photosensitive layer is made of a conventionally known sensitizer such as terphenyl, halonaphthoquinones, acenaphthylene, and 9- (N, N
Various additives such as a fluorene compound such as -diphenylhydrazino) fluorene and 9-carbazolyliminofluorene, a plasticizer, an antioxidant, an antiaging agent such as an ultraviolet absorber and the like may be contained.

The single-layer type photosensitive layer containing the above-mentioned perylene compound, triphenylamine derivative, binder resin and the like may have an appropriate thickness, but is 10 to 50 μm, particularly 15 to 25 μm.
Those having a thickness of are preferable.

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

The conductive substrate may be in the form of a sheet or a drum, or the substrate itself has conductivity, or the surface of the substrate has conductivity, and has sufficient mechanical strength when used. Are preferred. As the conductive base material, various materials having conductivity can be used, for example, aluminum,
Single metals such as copper, tin, platinum, gold, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, isodium, stainless steel, and brass, plastic materials in which the above metals are vapor-deposited or laminated, aluminum iodide Examples thereof include glass coated with tin oxide, indium oxide, or the like. Of the conductive substrate, aluminum, particularly, no aluminum crystal grains are present on the surface,
In order to prevent the generation of black spots and pinholes in a copied image and to improve the adhesion between the photosensitive layer containing the above-mentioned perylene compound, triphenylamine derivative and the like and the substrate, anodized Aluminum, in particular, alumite-treated aluminum having a film thickness of the alumite treatment layer of 5 to 12 μm and a surface roughness of 1.5 S or less is preferable.

In preparing the dispersion, various organic solvents can be used depending on the type of the binder resin used. Examples of the solvent include n-hexane, octane,
Aliphatic hydrocarbons such as cyclohexane, benzene, toluene, aromatic hydrocarbons such as xylene, dichloromethane,
Dichloroethane, carbon tetrachloride, halogenated hydrocarbons such as chlorobenzene, dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethers such as diethylene glycol dimethyl ether, acetone, ketones such as methyl ethyl ketone, cyclohexanone, ethyl acetate, Examples of various solvents include esters such as methyl acetate, dimethylformamide, dimethylsulfoxide, and the like, and one kind or a mixture of two or more kinds is used. In preparing the dispersion, a surfactant, a leveling agent, and the like may be used in combination in order to improve dispersibility, coatability, and the like.

Further, the dispersion can be prepared using a conventional method, for example, a ball mill, a paint shaker, a sand mill, an attritor, an ultrasonic disperser or the like, and the obtained dispersion is used as the conductive substrate. By coating and heating to remove the solvent, the electrophotographic photoreceptor of the present invention can be obtained.

In order to increase the adhesion between the conductive substrate and the photosensitive layer, an undercoat layer may be formed between the conductive substrate and the photosensitive layer. The pulling layer is formed by applying a solution containing a natural or synthetic polymer and having a film thickness after drying of 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 layer protective layer, the various binder resin, or a mixed solution of the binder resin and an additive such as a deterioration inhibitor is usually 0.1 to 10 μm in thickness after drying.
m, preferably about 0.2 to 5 μm.

In the electrophotographic photoreceptor of the present invention, the photosensitive layer contains a specific perylene compound and a triphenylamine derivative, and thus, is excellent in positive charging property and light stability,
Although it is a photoreceptor having a single-layer type photosensitive layer, it has high sensitivity and high surface potential and a small residual potential. Further, since it is a photoreceptor having a single-layer type photosensitive layer, an inexpensive electrophotographic photoreceptor can be easily manufactured with a 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> Hereinafter, the present invention will be described in more detail with reference to Examples.

Example 1 100 parts by weight of poly (4,4′-cyclohexylidenediphenyl) carbonate (trade name Polycarbonate Z, manufactured by Mitsubishi Gas Chemical Co., Inc.), 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 ', 4 "
-Tris (N, N-diphenylamino) triphenylamine 100 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, which was then anodized. It was applied onto an aluminum plate to prepare an electrophotographic photoreceptor having a photosensitive layer having a thickness of about 20 μm.

Example 2 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4 ′, 4 ″ -tris [N, N-di (4-methyl) was used. Using (phenyl) amino] triphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Example 3 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4 ′, 4 ″ -tris [N- (4-methylphenyl)- N-phenylamino]
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that triphenylamine was used.

Example 4 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4 ′, 4 ″ -tris [N- (4-methoxyphenyl)- Using N-phenylamino] triphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1.

Example 5 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4 ′, 4 ″ -tris [N- (4-chlorophenyl) -N was used. -Phenylamino]
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that triphenylamine was used.

Example 6 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4- [N- (2-methylphenyl) -N- (4-methylphenyl) was used. )amino]
-4 '-[N- (3-methylphenyl) -N- (4-methylphenyl) amino] -4 "-[N, N-di (3-methylphenyl) amino] triphenylamine An electrophotographic photoreceptor was prepared in the same manner as in Example 1.

Example 7 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4′-bis (N, N-
Using diphenylamino) triphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Example 8 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4-4′-bis (N,
Using N-diphenylamino) -4 ″ -methyltriphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Example 9 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4′-bis (N, N-
Using diphenylamino) -4 ″ -methoxytriphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1.

Example 10 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4′-bis (N, N-
Using diphenylamino) -4 ″ -chlorotriphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Example 11 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 4,4′-bis (N, N-
Using diphenylamino) -4 ″ -dimethylaminotriphenylamine, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Comparative Example 1 N-Ethyl-3-carbazolylaldehyde N, N-diphenylhydrazone was used in place of 4,4 ', 4 "-tris (N, N-diphenylamino) triphenylamine of Example 1. An electrophotographic photoreceptor was prepared in the same manner as in Example 1.

Comparative Example 2 Instead of N, N'-di (3,5-dimethylphenyl) perylene-3,4-9,10-tetracarboxydiimide of Example 1, N, N'-di (4-methoxyphenyl) ) Perylene-3,
Using 4,9,10-tetracarboxydiimide, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Comparative Example 3 Instead of N, N′-di (3,5-dimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide of Example 1,
N, N-di (2,4,6-trimethylphenyl) perylene-3,4,
Using 9,10-tetracarboxydiimide, an electrophotographic photoreceptor was prepared in the same manner as in Example 1 above.

Comparative Example 4 Instead of N, N′-di (3,5-dimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide of Example 1,
An electrophotographic photosensitive member was produced in the same manner as in Example 1 using dibromoanthanthrone.

Comparative Example 5 Instead of N, N'-di (3,5-dimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide of Example 1,
An electrophotographic photosensitive member was produced in the same manner as in Example 1 using metal-free phthalocyanine.

Comparative Example 6 4- (N, N-diethylamino) benzaldehyde N, N-diphenylhydrazone was used in place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1. An electrophotographic photoreceptor was prepared in the same manner as in Example 1.

Comparative Example 7 In place of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine of Example 1, 1-phenyl-3-
Using (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline, a photoreceptor for electrophotography was prepared in the same manner as in Example 1 above.

Comparative Example 8 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that polyvinylcarbazole was used instead of 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine in Example 1. Was produced.

Also, for reference, the charge generating material and the charge used in the above examples are compared with the characteristics of the photoreceptor having the laminated photosensitive layer using the charge generating material and the charge transporting material of the above examples 1, 4 and 5. A photoreceptor having a laminated photosensitive layer was produced as follows using the transport material.

Polyvinyl butyral (manufactured by Sekisui Chemical Co., Ltd., trade name S-REC (C) 100 parts by weight, 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, twenty four
A dispersion liquid for a charge generation layer was prepared by mixing and dispersing for a time. The above charge generation layer dispersion was applied onto the conductive base material used in Example 1 so that the film thickness after drying was about 0.5 μm to form a charge generation layer.

In addition, polyester (manufactured by Toyobo Co., Ltd., product name Byron 20
0) With respect 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 used and mixed by stirring to prepare the above coating liquid for the charge transporting layer,
A charge transport layer having a thickness of about 18 μm after drying was formed on the charge generation layer to prepare an electrophotographic photoreceptor having a laminated type photosensitive layer corresponding to the above example.

Then, in order to examine the charging characteristics and the photosensitive characteristics of the electrophotographic photoreceptors obtained in the above Examples and Comparative Examples, a single layer was prepared using an electrostatic copying machine test apparatus (Kawaguchi Electric Co., SP-428 type). +6.0 KV for electrophotographic photoconductors having a photosensitive layer, and -6 for electrophotographic photoconductors having a laminated photosensitive layer.
Corona discharge was performed under the condition of 0 KV to charge the electrophotographic photoconductors of the respective Examples and Comparative Examples.

The surface potential Vsp (V) of each photoconductor was measured, and a tungsten lamp with an illuminance of 10 lux was used.
The surface of the photoreceptor was exposed to light, the time until the surface potential Vsp became 1/2 was calculated, and the half-exposure amount E1 / 2 (μJ / cm ² ) was calculated. The surface potential 0.15 seconds after the exposure was taken as the residual potential Vrp (V).

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

As is clear from Table 1, all the photoreceptors of Comparative Examples had insufficient sensitivity and high residual potential.

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

Further, in order to examine the change in the characteristics of the photoconductor due to the light irradiation, the electrophotographic photoconductors of Example 1 and Comparative Example 1 were irradiated with a light source having an illuminance of 1000 lux for 5 minutes, and then the properties of the respective photoconductors were measured. Was examined in the same manner as above, and the difference from the initial characteristics was obtained. The results shown in Table 2 were obtained.

As is clear from Table 2 above, the electrophotographic photosensitive member of Comparative Example 1 not only has a significantly increased surface potential and residual potential, but also has a significant decrease in sensitivity due to light irradiation, and thus has insufficient repeating characteristics. found.

On the other hand, the photoconductor of Example 1 is
It was found that the charging characteristics and the sensitivity characteristics did not change so much and that they showed stable characteristics even after repeated use.

<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 triphenylamine derivative and a binder resin, the photosensitive layer is excellent in positive charging property and light stability, and the sensitivity and High surface potential and low residual potential. Further, since it is a single-layer type photoreceptor, it has a unique effect that it can be easily manufactured with a high yield and is inexpensive.

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Claims (7)

[Claims] 1. A photoreceptor having a single-layer type photosensitive layer containing a charge generating material, a charge transporting material, and a binder resin, wherein the charge generating material is a perylene compound represented by the following general formula (1). And a charge transporting material is a triphenylamine 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 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkyl group on the phenyl ring, a lower alkoxy group or a diphenylamino group optionally having a halogen atom, a dialkylamino group. R ⁶ and R ⁷ are the same or different and each represents a lower alkyl group, a lower alkoxy group or a diphenylamino group which may have a halogen atom on the phenyl ring.) 2. The electrophotographic photoconductor 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 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a halogen atom,
C1-C4 alkyl group on the phenyl ring, C1-C1
4 alkoxy group or diphenylamino group which may have a halogen atom, and the number of carbon atoms in the alkyl group is 1 to
The above-mentioned claim 1 which is 4 dialkylamino groups.
The electrophotographic photoreceptor according to the item 1. 4. R ⁶ and R ^{7, which} may be the same or different, may each have an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a diphenylamino which may have a halogen atom on the phenyl ring. The electrophotographic photoreceptor according to claim 1, which is a base. 5. A perylene-based compound is N, N'-bis (3,5-
The electrophotographic photoreceptor according to claim 1, which is dimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide. 6. A photosensitive layer, based on 100 parts by weight of a binder resin,
The electrophotographic photoreceptor according to claim 1, containing 2 to 20 parts by weight of the perylene compound and 40 to 200 parts by weight of the triphenylamine derivative. 7. The electrophotographic photoreceptor according to claim 1 or 6, wherein the photosensitive layer contains metal-free phthalocyanine or titanyl phthalocyanine.