JPS62123469A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain the titled body having a high sensitivity by incorporating a specific hydrazone compd. to the titled body as the electron transfer substance. CONSTITUTION:The photosensitive layer contains the hydrazone compd. shown by formulas I, II or III, as the electron transfer substance. In the formulas, X is O, S or an imino group, R<1> is an alkoxy, an aralkyloxy or a substd. amino group, R<2> and R<3> are each H, a halogen atom or an alkyl group, R<4> is H, an alkyl or a phenyl group, R<6>-R<9> are each an alkyl, a phenyl or an alkoxy group, etc., A is a group shown by formulas IV, V or VI (wherein Y and Z are each S, O or N-R<17>, R<14> and R<15> are each H, an alkyl or an alkoxy group, etc., R<16> is H, an alkyl or an alkoxy group, etc., R<17> is 1-4C an alkyl group), B is an aryl group. When the compd. shown by formulas I-III is used, the titled body having a high sensitivity and a small residual potential is obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a charge transporting substance and a charge generating substance in the same layer.

[Conventional technology and problems]

The photoconductive process of electrophotographic photoreceptors is (1) Process of generating electric charge by exposure to light (2) ? ! ! process of transporting cargo That's what happens.

A selenium photosensitive plate is an example of performing (1) and (2) using the same material. On the other hand, as an example of performing (1) and (2) using separate substances, a combination of amorphous selenium and poly-N-vinylcarbazole is known as a good combination. It has the advantage of expanding the selection range of materials used for photoreceptors, thereby improving the electrophotographic properties of the photoreceptor such as sensitivity and acceptance potential, and allowing the selection of materials convenient for photoreceptor coating from a wide range. are doing.

Conventionally, inorganic substances such as selenium, cadmium sulfide, and zinc oxide have been used as photoconductive materials for photoreceptors used in electrophotography.

Electrophotography has already been published by Carlson in US Patent No. 2.297.
, 691, uses a photoconductive material consisting of a support coated with a dark insulating substance whose electrical resistance changes depending on the amount of radiation received during image exposure. The photoconductive material is generally first given a uniform surface charge in the dark after dark adaptation for a suitable period of time. The material is then imagewise exposed with a pattern of radiation that has the effect of reducing the surface charge depending on the relative energy contained in different parts of the radiation pattern. The surface charge or electrostatic latent image thus left on the surface of the photoconductive material layer (photosensitive layer) then becomes a visible image when that surface is contacted with a suitable electrometric indicator material, ie, toner. Toner, whether contained in an insulating liquid or in a dry carrier, can be deposited on the surface of the photosensitive layer depending on the charge pattern. The deposited display material can be fixed by known means such as heat, pressure, and solvent vapor. The electrostatic latent image can also be transferred to a second support (eg, paper, film, etc.).

It is likewise possible to transfer the electrostatic latent image to a second support and develop it there. Electrophotography is one of the image forming methods in which images are formed in this manner.

The basic characteristics required of a photoreceptor in such an electrophotographic method are (1) ability to be charged to an appropriate potential in a dark place, (2) less dissipation of charge in a dark place,
(3) Examples include scales that quickly dissipate charge when irradiated with light. It is true that the inorganic substances conventionally used have many advantages and at the same time various disadvantages. For example, selenium, which is currently widely used, has the above-mentioned (1) to ( Condition 3) is fully satisfied, but the manufacturing conditions are difficult, the manufacturing cost is high (it is not flexible, it is difficult to process it into a belt shape, and it is sensitive to heat and mechanical shock). Cadmium sulfide and zinc oxide are dispersed in a resin as a binder and used as a photoreceptor, but they have a hardness of 1 tensile strength, abrasion resistance, etc. Due to its mechanical drawbacks, it cannot be used repeatedly as it is.

In recent years, in order to eliminate the drawbacks of these inorganic materials, photoreceptors for T-photography using various organic materials have been proposed, and some of them have been put into practical use. For example, ytrlJ-N-
Vinylcal, 6sol! =2,4,7-dolinitrofluoren-9-one (U.S. Pat.
, 484.237), poly-N-vinylcarbazole sensitized with biryllium base dye (Japanese Patent Publication No. 48-25
658), and a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (Japanese Unexamined Patent Publication No. 10735/1983).

Furthermore, a highly sensitive electrophotographic photoreceptor has been proposed that combines a substance that generates electric charges when exposed to light (called a charge-generating substance) and a substance that can transport the generated charges (called a charge-transporting substance). has been done. For example, U.S. Patent No.
No. 791,826 discloses a photoreceptor in which a charge transport layer is provided on a charge generation layer, and U.S. Pat. No. 3,573,906 discloses a photoreceptor in which a charge generation layer is provided on a charge transport layer. Photoreceptors are also described in U.S. Pat. No. 3,764,315 each having a photosensitive layer having a charge generating material dispersed in a charge transporting material. Although many useful charge-generating substances have been proposed for this type of photoreceptor, the current situation is that very few truly useful charge-transporting substances have been proposed. A good charge-transporting material is one that sufficiently transmits light of a wavelength that causes charge generation from the charge-generating material, that has scales that maintain sufficient potential when charged, and that the charge-generating material It has the ability to quickly transport the charges generated by

The present inventors conducted studies to obtain a hydrazone compound that can be used as an excellent charge transport material as described above.

An example of using a certain hydrazone compound as an organic photoconductor in place of zinc oxide or the like in an electrophotographic photoreceptor is disclosed in, for example, US Pat. No. 3,765,884. However, this document only discloses that hydrazone compounds are used as organic photoconductors in combination with sensitizing dyes, and does not disclose that these hydrazone compounds are used as charge transport materials in combination with charge generating substances. Some parts are not listed.

Further, an example of using a hydrazone compound in an electrophotographic photoreceptor as a charge transport material in combination with a charge generating agent is described in U.S. Pat.
, 7 i 7,462, (Specification of Japanese Patent Publication No. 48-813
7), JP-A-54-59143 (corresponding to U.S. Patent No. 4,150,987), JP-A-55-52063, JP-A-55-52064, etc. Can be seen.

However, all of the hydrazone compounds described in these patents use fused polycyclic compounds or N-alkylamino substituted compounds, and are susceptible to oxidation by ozone generated by corona charging, which can be said to be a fatal drawback for electrophotographic photoreceptors. light,
Thermal stability and dark decay were poor, and the sensitivity was also insufficient.

The present inventors have previously discovered that an electrophotographic photoreceptor having a photosensitive layer in which an N-arylamino substituted product is used as a charge transport material in combination with a charge generation material is free from the above-mentioned drawbacks, has high sensitivity, and is a cause of fogging. It was discovered that the residual potential and sensitivity of
It was proposed as No. 7-11350 and Japanese Unexamined Patent Publication No. 104144/1983.

The present inventors further conducted intensive research on hydrazone compounds having similar properties to the compounds of the present invention and different chemical structures, and found that the general formula CI), (n) or The present invention was achieved by discovering that the hydrazone compound represented by (1[1) is a truly useful charge transport material for electrophotographic photoreceptors.

Therefore, an object of the present invention is to provide an electrophotographic photoreceptor having an electrophotographic photosensitive layer containing an excellent charge transport material together with a charge generating material.

Another object of the present invention is to provide an electrophotographic photoreceptor having an electrophotographic photosensitive layer with high sensitivity and low residual potential.

Still other objects of the present invention are that the present invention is stable against oxidation caused by ozone generated by corona charging, light, and heat, has little dark decay of potential (and has little increase or fluctuation in residual potential due to repeated use, and has low fluctuation in sensitivity). It is an object of the present invention to provide an electrophotographic photoreceptor having a stable electrophotographic photosensitive layer with low irradiation.

Still another object of the present invention is to provide an electronic compound that can be synthesized using non-toxic or less toxic raw material compounds and that contains a non-toxic or less toxic charge transport substance together with a charge generating substance. An object of the present invention is to provide an electrophotographic photoreceptor having a photosensitive layer that is safe to handle and dispose of.

Still another object of the present invention is to provide a stable charge transport layer that has high film strength, excellent uniformity, and less fatigue deterioration.

The present invention relates to the following general formula (I), (n) or (II)
The present invention relates to an electrophotographic photoreceptor characterized by having a photosensitive layer containing the compound represented by I).

However, X represents an oxygen atom, a sulfur atom, a selenium atom, an imino group with or without a substituent, or a methylene group with or without a substituent. R is an alkoxy group, an aralkyloxy group. n1111 and R1
1 represents an alkyl group with or without a substituent, a phenyl group with or without a substituent, or a group in which Hlo and R11 can be linked to form a nitrogen atom-containing heterocycle; R11 may be the same or different.

R2 and R3 represent a hydrogen atom, a hydrogen atom, an alkyl group or a lower alkoxy group, and these may be the same or different groups.

R4 represents a hydrogen atom, an alkyl group, or a phenyl group with or without a substituent.

R5 represents an alkyl group with or without a substituent.

R6, R7, R8 and R9 represent an alkyl group, a phenyl group, an alkoxy group, an aralkyloxy group, each with or without a substituent, or a hydrated amine group. R12 and R15 are hydrogen atoms, or the above-mentioned R1
It is the same as the group represented by 0 and R11. R6, R7,
R8 and R9 may be the same or different from each other (or may be linked to form a fused carbocycle or fused heterocycle).

A represents a monocyclic, fused 5-membered heterocyclic ring, or fused 6-membered heterocyclic ring represented by the following structural formula.

Y and 2 are S, O, N-RCR&! Carbon number 1 to 4
(alkyl group), and may be the same or different atoms. R and R are the same or different groups, and represent a hydrogen atom, an alkyl group, or an alkoxy group, or a group in which R and R can be linked to form a benzene ring or a naphthalene ring.

R16 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a halogen atom, a monoalkylamino group, a dialkylamino group, an amine) group, or a nitro group. These may or may not have a substituent.

B represents an aryl group with or without a substituent.

Note that some of the hydrazone compounds represented by the general formula (I) used in the present invention are disclosed in the above-mentioned U.S. Patent No. 3,765,88.
The hydrazone compounds described in this US patent are related to organic photoconductors used in combination with sensitizing dyes, although most of the hydrazone compounds described in the specification of No. 4 are related to so-called charge transport. It has been found that only substances that do not have a function as a substance and are included in the general formula (I) of the present invention exhibit the above-mentioned excellent function as a charge transport substance when used in combination with a charge generation substance. It is.

Specific examples of X, which will be described in detail in the present invention below, include an oxygen atom, a sulfur atom, a selenium atom, an alkylimino group, and a dimethylmethylene group.

The alkyl group of the alkylimino group is an alkyl group having 1 to 8 carbon atoms. As X, a sulfur atom is particularly preferable.

The alkoxy group or aralkyloxy group of R1 includes an alkoxy group having 1 to 12 carbon atoms and an aralkyloxy group having 1 to 12 carbon atoms, and specific examples thereof include methoxy group, ethoxy group, zolopoxy group, cytoxy group, and octyloxy group. group, benzyloxy group.

In this case, Rjo and R11 are an alkyl group having 1 to 12 carbon atoms without a substituent such as a methyl group, ethyl group, propyl group, or butyl group, or an alkyl group having 1 to 12 carbon atoms and having a substituent as shown below. It has an alkyl group.

Substituents for the alkyl group having a substituent represented by R10 and R11 include an alkoxy group having 1 to 4 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, a hydroxy group, an aryl group having 6 to 12 carbon atoms, These include cyano groups and halogen atoms. Specific examples of the alkyl group having a substituent represented by R10 and R11 include a) alkoxyalkyl such as methoxymethyl, methoxyethyl, ethoxymethyl, ethoxymethyl, ethoxypropyl, methoxybutyl, propoxymethyl, b) phenoxymethyl , phenoxyethyl, naphthoxymethyl, aryloxyalkyl such as phenoxypentyl, C) hydroxymethyl, hydroxypropyl,
hydroxyoctyl, hyP-roxyalkyl such as hyP-roxymethyl, d) heptaralkyl such as benzyl, phenethyl, ω, ω-diphenylalkyl, e) cyanomethyl,
cyanoalkyl such as cyanoethyl, cyanopropyl, cyanobutyl, cyanoethyl and f) chloromethyl,
Noroalkyl such as bromomethyl, chloroethyl, bromopentyl, chlorooctyl, etc. are preferred.

The phenyl group represented by 110 and R11 may have a substituent, and specific examples of the substituent in the case of a phenyl group having a substituent include a) an alkyl group having 1 to 12 carbon atoms, b) a carbon an alkoxy group having 1 to 4 carbon atoms; c) an aryloxy group having 6 to 7 carbon atoms;

d) Acyl group having 2 to 8 carbon atoms, e) Alkoxycarbonyl group having 2 to 5 carbon atoms, r) /.rogen atom, g) Monoalkylamino group substituted with an alkyl group having 1 to 4 carbon atoms, h ) a dialkylamino group substituted with an alkyl group having 1 to 4 carbon atoms, i) an amide group having 2 to 4 carbon atoms, and j
) and nitro groups.

a) Methyl group, ethyl group, linear or branched propyl group, butyl group, pentyl group, hexyl group as an alkyl group having 1 to 12 carbon atoms; b) methoxy as an alkoxy group having 1 to 4 carbon atoms group, ethoxy group, propoxy group,
butoxy group, C) phenoxy 2 as aryloxy group
%, o +, m - or p-) lyloxy group, d)
As an acyl group, an acetyl group, a propionyl group, a benzoyl group, 0-lm- or p-toluoyl group%e) As an alkoxycarbonyl group having 2 to 5 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a flopoxycarbonyl group, a butoxycarbonyl group group, f) chlorine atom, bromine atom, fluorine atom as norogen atom, g) Roasted Z
A methylamine group, ethylamino group, butylamino group as a monoalkylamino group substituted with an alkyl group having 1 to 4 carbon atoms; dimethylamine group as a dialkylamino group substituted with an alkyl group having 1 to 4 carbon atoms; , diethylamino group, dipropylamino group, dibutylamino group, N-methyl-N-ethylamino group, l) amide group such as acetamido group, propionamide group, j) other substituents include nitro group.

The heterocycle formed by connecting R10 and R11 is preferably a heterocycle represented by the following structural formula.

R1 is preferably a substituted amino group, and R10 and R1j
is preferably a substituted amino group in which is a methyl group, ethyl group, benzyl group, phenyl group, or tolyl group. In particular, substitution with dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, N-ethyl-N-phenylamino group, etc. is particularly preferred.

R2 and R3 include hydrogen atom: salt: 2 atom, bromine atom, fluorine atom, etc.; alkyl group having 1 to 4 carbon atoms such as methyl, ethyl group, propyl group, butyl group; methoxy group, Examples include alkoxy groups having 1 to 4 carbon atoms such as ethoxy group, propoxy group, and butoxy group. Among them, hydrogen atoms, methyl groups, methoxy groups, etc. are preferred.

Specific examples of R4 include hydrogen atom; methyl group, ethyl group,
Examples include alkyl groups having 1 to 4 carbon atoms such as propyl and butyl groups, and phenyl groups with or without substituents. The phenyl group having a substituent is the above-mentioned R10
Alternatively, it is a group similar to the phenyl group having a substituent represented by R11.

Among R4, preferred are a hydrogen atom, a methyl group, an ethyl group, a phenyl group, and a p-()methylamine)phenyl group.

The alkyl group with or without a substituent represented by R5 is the same as the alkyl group with or without a substituent represented by R or R described above.

R6, R7, R8 and R9 include an alkyl group with or without a substituent or a phenyl group with or without a substituent, which is similar to the above-mentioned R10 or R1.
This is a group similar to the group represented by 1.

Hydrogen atoms; halogen atoms such as chlorine, bromine, and fluorine atoms; alkoxy groups with 1 to 12 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, octyl, and benzyloxy groups; benzyloxy groups , aralkyloxy group having 1 to 12 carbon atoms such as phenethyloxy group, and R12 and R15 are hydrogen atoms and R1
It is a group similar to the alkyl group with or without a substituent represented by 0 or R11, and the phenyl group.

R6, R7, R8 and R9 may be the same or different from each other, or may be linked to form a fused carbocycle or fused heterocycle such as naphthalene.

Among them, hydrogen atoms are particularly preferred.

and R is a hydrogen atom; an alkyl group having 1 to 4 carbon atoms such as a methyl group, ethyl group, propyl group, butyl group; an alkyl group having 1 to 4 carbon atoms such as a methoxy group, ethoxy group, propoxy group, butoxy group; and a group capable of forming a benzene ring or a naphthalene ring by linking R14 and R15.

an alkyl group with or without a substituent similar to the alkyl group with or without a substituent represented by R or R described above, an alkoxy group having 1 to 4 carbon atoms, an aryloxy group having 6 to 10 carbon atoms; group, acyl group having 2 to 11 carbon atoms, alkoxycarbonyl group having 2 to 5 carbon atoms, aryloxycarbonyl group having 7 to 11 carbon atoms, 1 to 11 carbon atoms
Examples include a monoalkylamino group having 4 carbon atoms, a dialkylamino group having 1 to 4 carbon atoms, an amide group having 2 to 9 carbon atoms, and a nitro group. These may or may not have a substituent.

a methoxy group as an alkoxy group having 1 to 4 carbon atoms;
Ethoxy group, propoxy group, butoxy group; As aryloxy group, phenoxy group, o-, m- or -)lyloyl group; As acyl group, acetyl group, flopionyl group, - toluoyl group;
As an alkoxycarbonyl group having 2 to 5 carbon atoms, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group; 7 to 11 carbon atoms
As an aryloxycarbonyl group, phenoxycarbonyl M, 0-lm- or p-) IJ oxycarbonyl group; mono substituted with a salt A atom, a bromine atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms as a halogen atom; As an alkylamino group, a methylamine group, an ethylamino group, a butylamino group, as a dialkylamino group substituted with an alkyl group having 1 to 4 carbon atoms, a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, N -Methyl-N-dithylamino group, an amide group such as an acetamide P group or a propionamide group, and other substituents include a nitro group.

2-furyl group, 2-chenyl group, 1-methyl-2-pyrrolyl group, 5-methyl-
2-chenyl group; as a fused 5-membered hetero ring, 2-benzo[
b] chenyl group, 2-nat[2,3-b) chenyl group, 9-ethylcarbasol-z-yh group s,,y benzothiophen-2-yl group, as a fused 6-membered heterocyclic ring,
2-phenoxathiinyl group, 10-ethylphenoxazin-3-yl group, and 10-ethylphenothiazin-3-yl group. Et■ Zin-3-ylt 10-ethylphenothiazin-3-yl Among these, preferred are 5-methyl-2-chenyl group, 2--
<Nso [1)] chenyl group, 9-ethylcarbazole-
2-yl group, dibenzothiophen-2-yl group, 10-
It is an ethylphenothiazin-3-yl group.

A specific example of B is a phenyl group and a 7fka.

When a substituent is present, the substituent is the same group as R2 or R5.

Specific examples of the hydrazone compound represented by the general formula (I), ([) or (ITI) are shown below.

CH.

CH.

CH3 ■ CH3 CH3 CH.

CH.

CH3CH3 CH3 ■ CH3 〒H3 ■ CH.

The compounds represented by the general formula CI), (II) or (III) can be easily produced by known methods.

That is, it is obtained by dehydrating and condensing the heterocyclic hylazone and the corresponding aldehyde r or ketone in a solvent by adding a small amount of acid (acetic acid or inorganic acid) as a condensing agent if necessary. Solvents include alcohols such as methanol and ethanol, aromatics such as benzene and xylene,
Hydrocarbons, dioxane, tetrahydrofuran, N, N
- Dimethylformamide etc. can be used alone or in combination.

By using a compound represented by the general formula CI), (II) or (III) as a charge transport material, the film properties, durability, charging properties and residual potential properties of the electrophotographic photosensitive layer are improved. Also, general formulas (I), (II)
Or the compound represented by (III) can be used for various polymers,
Since the electrophotographic photosensitive layer does not become cloudy or opaque even if a large amount of the charge transport material is contained in the polymer binder, it is highly compatible with the charge transport material. Since the selection range and the range of the amount used of the molecular inder can be widened, it is possible to produce an electrophotographic photoreceptor having preferable charge transport performance and film physical properties depending on the purpose and use.

It is said that when the compound represented by the general formula (I), (n) or (III) is used as a charge transport material in combination with any charge generating material, it can constitute an electrophotographic photoreceptor having the above-mentioned excellent properties. has advantages.

Examples of charge generating substances used in the present invention include the following.

(1) Selenium and selenium alloys (2) CdS, CdSe, Cd5Se,
Inorganic photoconductors such as Zr+O and ZnS (3) Phthalocyanine pigments such as gold FA phthalocyanine and metal-free phthalocyanine nato (4) Azo dyes such as monoazo dyes and disazo dyes (5) Perylenes such as perylenic anhydride and perylenic acid imide Pigments (6) Indigoi P dyes (7) Quinacridone pigments (8) Polycyclic quinones such as anthraquinones, pyrenequinones, anthantrone and furano9antrone (9) Bisbenzimitazole pigment (M) cyanine Pigment (U) Square menane dye (12) Indanthrone pigment (13) Xanthine dye (14) Charge consisting of an electron-donating substance such as poly N-vinyl carnosol and an electron-accepting substance such as trinitrofluorenone Transfer complexes (15) Eutectic complexes formed from biryllium salt dyes and polycarbonate resins, and (16) amorphous silicon etal.

In the present invention, general formula (I), CII) or (III
The polymeric inder used with the compound represented by ) is a hydrophobic, electrically insulating film-forming polymer or copolymer with high octaconductivity.

Examples of such high molecular weight polymers or copolymers include the following.

(1) Polystyrene resin (2) Tetravinyl chloride resin (3) Polyvinylidene chloride resin (4),! ? Rivinyl acetate resin (5) Acrylic resin (6) Methacrylic resin (7) Styrene-butadiene copolymer (8) Vinylidene chloride-acrylonitrile copolymer (9)
) Vinyl chloride-vinyl acetate copolymer (10) Silicone resin (n) Polyester resin (12) Polycarbonate resin (13) Styrene-alkyd resin (14) Silicone-alkyd resin (15) Phenol-formaldehyde F' [fat Polymer) ζ Ingu can be used alone or in a mixture of two or more types, but the polymer binders that can be used in the present invention are:
It is not limited to these.

The photoreceptor of the present invention can be obtained by dispersing or dissolving a charge-generating substance together with a charge-transporting substance in a polymer/ζingo and providing it as a uniform layer on a conductive support. However, an organic dye may be used as the charge-generating substance. in case of,
A photoreceptor obtained by using an organic dye in an aggregated state and mixing it with a charge transport material in a non-uniform state is preferable because it has high sensitivity and excellent durability. Furthermore, a photoreceptor obtained by dispersing fine particles of a charge generating substance in a charge transport layer provided on a conductive support via an intermediate layer if necessary can also be effectively used in the present invention.

A charge generating material and a charge transporting material are used in the same layer,
0.0 parts by weight of the polymer binder per 1 part by weight of the compound of the present invention.
Preferably, 8 to 4 parts by weight and 0.1 to 2 parts by weight of the charge generating substance are used.

Further, when the charge generation layer is a dispersion system of a charge generation substance and a polymer/zeta-ing group, it is preferable to use the polymer binder in an amount of 10 parts by weight or less per 1 part by weight of the charge generation substance.

The conductive support constituting the photoreceptor of the present invention may be a paper or plastic support made conductive by adding a conductive compound or a thin metal layer to the surface, or if necessary geladium, aluminum, etc. Any material such as a silver-gold or vacuum-deposited metal plate, or an aluminum plate can be used.

In addition to the above-mentioned polymer 2-inder, casein,
Gelatin, starch, polyvinyl alcohol 1. T? Organic polymer compounds such as IJ vinegar 11 vinyl, ethyl cellulose, and calxoxymethyl cellulose, or metal oxides such as aluminum oxide are used.

〔Example〕

Next, the present invention will be explained in more detail with reference to synthesis examples and examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.

In the following examples, all parts indicate parts by weight. Synthesis Examples 1 to 7 Synthesis examples of the compound (1) of the present invention are shown.

3-methyl-2-benzothiazolinone hydrazone 30,
3,! ? ,! :, 30.9 oz of p-(diethylamino)benzaldehyde was mixed with 50 od of ethanol and 100 od of acetic acid (
! It was dissolved in a mixed solvent with c and refluxed for 2 hours. After cooling,
The obtained yellow precipitate was collected by filtration, dried, and then recrystallized from an ethanol solution to obtain N-(p-(diethylamino)pen)I)yn)-N'-(3-methyl-2- Benzothiazolylidene)hydrazine compound (1) CFI.

43.9 was obtained. Melting point: 139.5-140.3°C Yield: 77% Other compounds were similarly synthesized from the corresponding hydrazine and aldehyde or ketone.

Example 1 After adding 15 parts of β-type copper phthalocyanide to 660 parts of dichloromethane and performing ultrasonic dispersion, 40 parts of bisphenol A polycarbonate and 40 parts of compound (1) were added to this dispersion and dissolved. A coating solution was prepared.

This coating solution was applied onto a conductive transparent support (a 100 μm polyethylene terephthalate film with a vapor-deposited film of indium oxide and dium on the surface; surface electrical resistance ioSΩ) using a wire-row P rod, and dried. An electrophotographic photoreceptor having an electrophotographic photosensitive layer having a thickness of 9.5 μm was prepared.

After this photoreceptor was positively charged by +5KV corona discharge, the half-decreased exposure amount was measured, and F, 5) was 18 (
Lux-gpc).

Examples 2 to 9 Compound (2) was substituted for compound (1) in Example 1, respectively.
Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that ) to (9) were used, and E5 was similarly measured for each sample. The results obtained are shown in the table below.

Example Compound fIlh E5(7[
Lux＊s@c〕2 2 1
7.53 4 14.24
7 14.85
8 17.96 10
21.27 11
18.48 17 15.
39 18 18.6 Comparative Examples 1 to 3 Comparative photoreceptors were prepared in exactly the same manner as in Example 1 except that the following compounds were used instead of compound (1), and E50
was measured.

Comparative Compound Comparative Example Comparative Compound E50 (Lux-s)
2C-2154 3C-3209 [Effects of the Invention] As is clear from the above results, it can be seen that an extremely highly sensitive electrophotographic photoreceptor can be obtained according to the present invention.

Claims (1)

[Scope of Claims] An electrophotographic photoreceptor provided with a photosensitive layer containing an electron-generating substance and an electron-transporting substance in the same layer, wherein the electron-transporting substance is represented by the following general formula (I), (II) or (III). An electrophotographic photoreceptor characterized by having a photosensitive layer containing a compound that contains: ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(II) ▲Mathematical formulas, chemical formulas, There are tables, etc. ▼ (III) However, X represents an oxygen atom, a sulfur atom, a selenium atom, an imino group with or without a substituent, or a methylene group with or without a substituent; R^1 is an alkoxy R^
1^0 and R^1^1 are an alkyl group with or without a substituent or a phenyl group with or without a substituent,
Alternatively, R^1^0 and R^1^1 represent a group that can be linked to form a heterocycle containing a nitrogen atom, and R^1^0 and R
^1^1 may be the same or different; R^2 and R^3 represent a hydrogen atom, a halogen atom, an alkyl group, or a lower alkoxy group, and these may be the same or different groups. Good; R^4 represents a hydrogen atom, an alkyl group, a phenyl group with or without a substituent; R^5 represents an alkyl group with or without a substituent; R^6, R^7, R^8 and R^9 are alkyl groups, phenyl groups, alkoxy groups, aralkyloxy groups with or without substituents, hydrogen atoms, halogen atoms, or ▲mathematical formulas, chemical formulas, tables, etc.▼ represents an amino group represented by; R^1^2, R^1^3 are hydrogen atoms, or the above-mentioned R
^1^0 is the same as the group represented by R^1^1; R^6, R^7, R^8 and R^9 may be the same or different from each other, or they may be connected , fused carbocycle,
A fused heterocyclic ring may be formed; A represents a monocyclic or fused 5-membered heterocyclic ring or a fused 6-membered heterocyclic ring represented by the following structural formula; ▲ Numerical formula, chemical formula,
There are tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Y and Z are S, O, N-R^1^7 (R^1^7 is the number of carbon atoms 1 to 4 alkyl groups) and may be the same or different atoms; R^1^4 and R^1^5 are the same or different groups and represent a hydrogen atom, an alkyl group, or an alkoxy group or represents a group in which R^1^4 and R^1^5 can be linked to form a benzene ring or a naphthalene ring; R^1^6 is a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group , acyl group, alkoxycarbonyl group,
Represents an aryloxycarbonyl group, a halogen atom, a monoalkylamino group, a dialkylamino group, an amide group, or a nitro group, which may or may not have a substituent; B has a substituent represents an aryl group with or without