JPS63244045A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain a sensitive body having high sensitivity and superior potential stability during repeated use by using a specified azo pigment in a photosensitive layer. CONSTITUTION:A photosensitive layer contg. a disazo pigment represented by formula I is formed. In formula, R1 is H, alkyl or aryl, each of R2 and R3 is H, alkyl, alkoxy, halogen, cyano or nitro, and R2 and R3 may be the same or different; each of A and A' is coupler residue having phenolic OH, and the residues A, A; may be the same residues. Thus, an electrophotographic sensitive body usable for all of existing electrophotographic processes and having practical high sensitivity and stable potential characteristics during repeated use is obtd.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a disazo pigment having a specific molecular structure in its photosensitive layer. It is related to.

[Conventional technology]

Conventionally, electrophotographic photoreceptors using inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide as main components of the photosensitive layer are widely known.

On the other hand, since the discovery that certain organic compounds exhibit photoconductivity, many organic photoconductors have been developed. In particular, regarding electrophotographic photoreceptors using pigments or dyes that act as photoconductors, for example, US Pat.
Electrophotographic photoreceptors using phthalocyanine pigments as shown in US Pat. No. 4,315,983, US Pat. 3824
Electrophotographic photoreceptor using methine squaric acid dye disclosed in Publication No. 099 etc., US Pat. No. 425161
Examples include electrophotographic photoreceptors using disazo pigments as disclosed in Publications No. 3, No. 4278747, and No. 4293628.

Electrophotographic photoreceptors using such organic photoconductors can be produced by a coating method by selecting an appropriate binder, so compared to those using inorganic photoconductors, they are inexpensive and extremely easy to photoconduct. It has the advantage that it can be manufactured in various colors and that the wavelength range of light sensitivity can be controlled by selecting the organic pigment. However, such photoreceptors have poor sensitivity and durability.

Only a few have been put into practical use so far.

[Problem that the invention seeks to solve]

It is an object of the present invention to provide a new photoconductive material.

Another object of the present invention is to provide an electrophotographic photoreceptor that can be used in all existing electrophotographic processes and has practical high sensitivity characteristics and stable potential characteristics during repeated use. be.

A second object of the present invention is to provide an electrophotographic photoreceptor having a wide spectral sensitivity ranging from the visible region to the near-infrared region and the infrared region.

[Means for solving problems]

The present invention comprises a photoconductive coating containing a disazo pigment represented by the following general formula (1).

A-N=N N=N-A' General formula (1)
R1 represents hydrogen, an alkyl group (methyl, ethyl, propyl, butyl, 5ec-butyl, t-butyl), an aryl group (e.g. phenyl, naphthyl), and R2 and R
3 is hydrogen, an alkyl group (e.g. methyl, ethyl, propyl, isopropyl, butyl, 5ee-butyl, t-butyl), an alkoxy group (e.g. methoxy, ethoxy, propoxy, phenoxy), a halogen group (e.g. fluorine, chlorine, bromine, iodine), cyano group, nitro group, and R2
and R3 may be the same or different.

A and A' in general formula (1) represent coupler residues having a phenolic OH group, and more preferred specific examples of coupler residues representing A and A' include general formulas (2) to (8).
A and A' may be the same or different.

In formula (2), X is fused with a benzene ring to form a polycyclic aromatic ring such as a naphthalene ring, an anthracene ring, a carbazole ring, a benzcarbazole ring, a dibenzofuran ring, a dibenzonaphthofuran ring, a diphenylene sulfide ring, or a hetero ring. Residues required for formation are shown.

The ring to which X is bonded is more preferably a naphthalene ring, an anthracene ring, a carbazole ring, or a benzcarbazole ring.

R4 and R in formula (2) represent hydrogen, an alkyl group which may have a substituent, an aryl group, an aralkyl group, a heterocyclic group, or a cyclic amino group together with the nitrogen atom to which R4 and R5 are bonded.

Specific examples of alkyl groups include methyl, ethyl, propyl, butyl, etc. Specific examples of aralkyl groups include benzyl, phenethyl, naphthylmethyl, etc. Specific examples of aryl groups include phenyl, diphenyl, naphthyl, anthryl, etc. Specific examples of the heterocyclic group include carbazole, dibenzofuran, benzimidacylone, benzthiazole, thiazole, and pyridine.

R6 and R in the general formulas (3) and (4) represent hydrogen, an alkyl group that may have a substituent, an aryl group, or an aralkyl group. A specific example of R,, R7 is shown by the same example as R4°RlI above.

Substituents R4, R? in formulas (2) to (4)? The alkyl group, aryl group, aralkyl group, alkoxy group, and heterocyclic group represented by may further include other substituents such as halogen groups such as fluorine, chlorine, iodine, and bromine, alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, methoxy, ethoxy,
Alkoxy groups such as propoxy and phenoxy, nitro groups,
It may be substituted with a substituted amino group such as a cyano group, dimethylamino, dibenzylamino, diphenylamino, morpholino, piperidino, and pyrrolidino.

Y in the general formulas (5) and (6) represents a divalent aromatic hydrocarbon group or a heterocyclic divalent group containing a nitrogen atom in the ring.

Examples of divalent groups of aromatic hydrocarbons include divalent groups of monocyclic aromatic hydrocarbons such as O-phenylene, fused polyesters such as 0-naphthylene, perinaphthylene, ■, 2-antrylene, 9, 1O-phenanthrylene, etc. Divalent groups of cyclic aromatic hydrocarbons are mentioned. Also, 2 of a heterocycle containing a nitrogen atom in the ring
As the valent group, 3,4-pyrazolediyl group, 2,3
-pyridinediyl group, 4,5-pyrimidinediyl group, 6
, 7-indazolediyl group, and 6,7-chiralindiyl group.

R8 in the general formula (7) represents an aryl group or a heterocyclic group which may have a substituent, and specifically represents a phenyl, naphthyl, anthryl, pyrenyl, vizylyl, chenyl, furyl, or carbazolyl group. .

Substituents for the aryl group and heterocyclic group represented by R8 include halogen groups such as fluorine, chlorine, iodine, and bromine, alkyl groups such as methyl, ethyl, propyl, isopropyl, and butyl, methoxy, ethoxy, propoxy, and phenoxy. alkoxy group, nitro group, cyano group, dimethylamino,
Examples include substituted amino groups such as dibenzylamino, diphenylamino, morpholino, piperidino, and pyrrolidino.

R9r RI in formula (8). represents an alkyl group, aryl group, aralkyl group, or heterocyclic group which may have a substituent, specifically methyl, ethyl, propyl, butyl, benzyl, phenethyl, naphthylmethyl, phenyl, naphthyl, anthryl. , diphenyl, carbazole, dibenzofuran, benzimidasilone, benzthiazole, thiazole, pyridine.

R9*RI in formula (8). Substituents for alkyl groups, aryl groups, aralkyl groups, and heterocyclic groups include halogen groups such as fluorine, chlorine, iodine, and bromine, alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, methoxy, ethoxy, and propoxy. , alkoxy groups such as phenoxy, nitro groups, cyano groups, substituted amino groups such as dimethylamino, dibenzylamino, diphenylamino, morpholino, piperidino, and pyrrolidino.

Next, a general method for producing the disazo pigment used in the present invention will be described.

When A and A' are the same in the disazo pigment represented by the general formula (1), the triamine represented by the general formula (9) is converted into a tetrazonium salt using a conventional method such as sodium nitrite or nitrosyl sulfuric acid as a coupler component. It can be obtained by performing aqueous coupling with A and A', or by extracting the general formula or the obtained tetrazonium salt as a stable salt such as a borofluoride salt and then performing coupling in an organic solvent such as DMF. If A and A' are different, in the coupling reaction, first couple with the first coupler component to form a monoazo pigment, and then couple with the second coupler component to form a disazo pigment, or Although it can be obtained by mixing coupler components and performing a coupling reaction, the former method is preferred in order to reliably obtain an asymmetric pigment.

Next, specific examples of the disazo pigments used in the present invention are listed in Table 1. However, the disazo pigments shown in the specific examples in Table 1 do not limit the scope of the claims of the present invention.

Table 1 Table 1 Table 1 Table 1 Table 1 Table 1 Table 1 The coating containing the disazo pigment described in Table 1 exhibits photoconductivity,
Therefore, it can be used in the photosensitive layer of an electrophotographic photoreceptor.

That is, in a specific example of the present invention, an electrophotographic photoreceptor is prepared by forming a film of the above-mentioned disazo pigment on a conductive support by vacuum evaporation, or by dispersing it in a suitable binder and forming a film. can do.

In a preferred embodiment of the present invention, the photoconductive coating described above can be applied as a charge generation layer in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer.

The charge generation layer contains as much of the above-mentioned photoconductive compound as possible in order to obtain sufficient absorbance, and a thin film layer to shorten the range of the generated charge carriers.
For example, it is preferable to use a thin film layer having a thickness of 5 μm or less, preferably 0.01 to 1 μm. This means that most of the incident light is absorbed by the charge generation layer, producing a large number of charge carriers, and that the generated charge carriers are not deactivated by recombination or trapping (charge transport This is due to the need to inject into the layer.

The charge generation layer can be formed by dispersing the above-mentioned compound in a suitable binder and coating it on the substrate, or can be obtained by forming a vapor deposited film using a vacuum vapor deposition apparatus. The binder used in forming the charge generating layer by coating can be selected from a wide variety of insulating resins and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene. Preferably, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.) polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin, Epoxy resin,
Examples include insulating resins such as casein, polyvinyl alcohol, and polyvinylpyrrolidone. The resin contained in the charge generation layer is 80% by weight or less, preferably 40% by weight or less.
A value of less than 2% is suitable.

The solvent that dissolves these resins varies depending on the type of resin, and is preferably selected from those that do not dissolve the underlying charge transport layer or subbing layer.

Specific organic solvents include methanol, ethanol,
Alcohols such as isopropanol, ketones such as acetone, methyl ethyl ketone, cyclohexanone, N
, amides such as N-dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, tetrahydrofuran, dioxane,
Ethers such as ethylene glycol and monomethyl ether, esters such as methyl acetate and ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene, or benzene, toluene, and xylene. Aromatics such as , ligroin, monochlorobenzene, and dichlorobenzene can be used.

Coating can be performed using a coating method such as a dip coating method or a spray coating method. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying at a temperature of 30°C to 200°C for 5 minutes to 2
It can be done stationary or under a draft for a range of hours.

The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field, and transporting these charge carriers to the surface. have. At this time, this charge transport layer may be laminated on or under the charge generation layer.

When the charge transport layer is formed on the charge generation layer, charge transport materials include electron transport materials and hole transport materials, and electron transport materials include chloranyl, bromoanil, tetracyanoethylene, and tetracyanyl. Cyanoquinodimethane, 2,4.7-dolinitro-9-fluorenone, 2.
4. 5. 7-tetranitro-9-fluorenone,
2. 4. 7-Dolinitro 9-dicyanomethylenefluorenone, 2, 4.5. There are electron-withdrawing substances such as 7-tetranitroxanthone and 2,4°8-trinidrothioxanthone, and polymerized versions of these electron-withdrawing substances.

Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isobrovir carbazole, and N-methyl-N
-Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N+N- Diphenylhydrazino-3-methylidene-10-ethylphenoxazine, ρ-diethylaminobenzaldehyde-N, N-diphenylhydrazone, ρ-
Diethylaminobenzaldehyde-N-α-naphthyl-
Hydrazones such as N-phenylhydrazone, ρ-pyrodininobenzaldehyde N, N-diphenylhydrazone, 2.5-bis(ρ-diethylaminophenyl) -
1,3,4-oxadiazole, 1-[quinolyl (2)
) -3-(ρ-diethylaminostyryl)-5-(ρ
-diethylaminophenyl)pyrazoline, 1-[6-
Medoxypyridyl (2)) -3-(ρ-diethylaminostyryl')-5-(ρ-diethylaminophenyl)pyrazoline, 1-(Levidyl (2)) -3-(ρ-
pyrazolines such as diethylaminostyryl)-5-(ρ-diethylaminophenyl)pyrazoline, 1-phenyl-3-(ρ-diethylaminostyryl)-4-methyl-5(ρ-diethylaminophenyl)pyrazoline, and spiropyrazoline; -diethylaminostyryl)-
Oxazole compounds such as 6-dinithylaminobenzoxazole, 2-(ρ-diethylaminophenyl)-4-(ρ-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, 2-(ρ-diethylaminostyryl)- Thiazole compounds such as 6-dinithylaminobenzothiazole, triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, ■, l-bis(4-N).

N-diethylamino-2-methylphenyl)hebutane,
1. 1.2.2-Tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane and other polyarylalkanes, triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, Examples include poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethylcarbazole formaldehyde resin.

In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium amorphous silicon, and cadmium sulfide can also be used.

Further, these charge transport substances can be used alone or in combination of two or more.

When the charge transport material does not have film-forming properties, a film can be formed by selecting an appropriate binder. Examples of resins that can be used as binders include acrylic resin,
polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer,
Insulating resins such as acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, or organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, polyvinylpyrene, etc. be able to.

Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, it is 5 to 30 μm, but the preferred range is 8 to 20 μm.
It is μm. When forming the charge transport layer by coating, an appropriate coating method as described above can be used.

A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Examples of substrates having a conductive layer include those in which the substrate itself is conductive;
For example, aluminum, aluminum alloy, copper, zinc, stainless steel, vanadium, molybdenum, chromium, titanium,
Nickel, indium, gold, platinum, etc. can be used, and plastics (for example, polyethylene , polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin,
(polyfluorinated ethylene, etc.), substrates made of plastic coated with conductive particles (e.g. carbon black, silver particles, etc.) together with a suitable binder, substrates made of plastic or paper impregnated with conductive particles, and plastics with conductive polymers. etc. can be used.

A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer is casein,
Polyvinyl alcohol, nitrocellulose, ethylene-
It can be formed from acrylic acid copolymer, polyamide (nylon 6', nylon 66, nylon 61O1 copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc.

The thickness of the subbing layer is 0.1 to 5 μm, preferably 0.5 to 5 μm.
3 μm is appropriate.

When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged, and exposure after charging is required. Then, in the exposed area, electrons generated in the charge generation layer are injected into the charge transport layer, and then reach the surface and neutralize the positive charge, causing a decrease in surface potential and creating an electrostatic contrast with the unexposed area. . A visible image can be obtained by developing the electrostatic latent image thus formed with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper, plastic film, etc. and then developed and fixed.

Alternatively, a method may be used in which the electrostatic latent image on the photoreceptor is transferred onto an insulating layer of transfer paper, and then visually imaged and fixed. The type of developer, the developing method, and the fixing method may be any known ones or known methods, and are not limited to specific ones.

On the other hand, when the charge transport material consists of a hole transport material, the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , which then reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the surface potential and the unexposed area. During development, it is necessary to use a positively charged toner, contrary to the case where an electron transporting substance is used.

Another specific example is a photoreceptor in which a conductive layer, a charge transport layer, and a charge generation layer are laminated in this order.

Further, in another specific example of the present invention, the above-mentioned hydrazones,
Organic photoconductive substances such as pyrazolines, oxazoles, thiazoles, triarylmethanes, polyarylalkanes, triphenylamine, poly-N-vinylcarbazoles, and inorganic photoconductive substances such as zinc oxide, cadmium sulfide, and selenium. A photosensitive film may be prepared containing the above-mentioned disazo pigment as a sensitizer. This photosensitive film is formed by coating these photoconductive substances and the above-mentioned disazo pigment together with a binder.

Another specific example of the present invention is an electrophotographic photoreceptor containing the above-mentioned disazo pigment and a charge transport material in the same layer. At this time, a charge transfer complex compound consisting of poly-N-vinylcarbazole and trinitrofluorenone can be used in addition to the above-mentioned charge transport substance. The electrophotographic photoreceptor of this example can be prepared by dispersing the aforementioned disazo pigment and charge transfer complex compound in a polyester solution dissolved in tetrahydrofuran, and then forming a film thereon.

The pigment used in any of the photoreceptors contains one type of pigment selected from disazo pigments represented by the general formula (1), and its crystal form may be amorphous or crystalline. .

In addition, if necessary, two or more types of disazo pigments represented by the general formula (1) may be used in combination for the purpose of increasing the sensitivity of the photoreceptor or obtaining a panchromatic photoreceptor by using a combination of pigments with different light absorption. It is also possible to use them in combination or in combination with a charge generating substance selected from known dyes and pigments.

The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers, CRT printers, L
It can also be widely used in electrophotographic applications such as ED printers, liquid crystal printers, and laser engraving.

Hereinafter, the present invention will be explained by examples.

Examples 1 to 25 Ammonia aqueous solution of casein (casein 1
1.2% ammonia water, 1 g of aqueous ammonia, and 222 mj of water were applied using a Mayer bar so that the film thickness after drying was 1.0 μm, and then dried.

Next, 15 g of the above-mentioned disazo pigment No. was added to 95 ml of ethanol with butyral resin (butyralization degree 63).
mol%) was added to the dissolved liquid and dispersed for 2 hours using a sand mill. This dispersion was applied onto the previously formed casein layer using a Mayer bar so that the film thickness after drying was 0.5 μm, and dried to form a charge generation layer. Next, 5 g of the hydrazone compound with the structural formula and 5 g of polymethyl methacrylate resin (number average molecular weight 100,000) were mixed with 70 g of benzene.
The photoreceptor of Example 1 was prepared by dissolving this in ml and applying it onto the charge generation layer using a Mayer bar so that the dry film thickness was 12 μm and drying to form a charge transport layer. All photoreceptors corresponding to Examples 2 to 25 were prepared in the same manner using other exemplary pigments shown in Table 1 in place of disazo pigment No. 1.

The electrophotographic photoreceptor produced in this way was manufactured by Kawaguchi Electric Co., Ltd.
Using an electrostatic copying paper tester Model 5P-428, it was statically charged with corona at 15Kv, and after being held in a dark place for 1 second, the illuminance was 2Jl! It was exposed to UV light and its charging characteristics were examined.

As for the charging characteristics, the photoreceptor of the present invention has a surface potential (Vo) and the exposure required to attenuate the potential when dark decayed for 1 second to % from the results shown in Table 2. It is clear that it has good sensitivity and potential characteristics.

Examples 26-30 Examples 1.2.9. 14. Using the photoreceptor used in Example No. 22, fluctuations in bright area potential and dark area potential during repeated use were measured. The method is to attach the photoreceptor to the cylinder of an electrophotographic copying machine equipped with a -5.6KV corona charger, exposure optical system, developer, transfer charger, static elimination exposure optical system, and cleaner. The structure is such that an image is obtained on the transfer paper as the transfer unit is driven. Using this copying machine, the initial bright area potential (Vt, ) and dark area potential (Vo) were each set to -100V.

The bright area potential (Vt) and dark area potential (Vo) were measured after being set at around -600V and used 5000 times. Example 31: On the charge generation layer prepared in Example 1, 5 g of 2.4.7-dolinitro-9-fluorenone and poly-4,4'-dioxydiphenyl-2,2'-propane carbonate (
5g (molecular weight: 300,000) in tetrahydrofuran (70%)
The coating amount after drying of the coating solution prepared by dissolving it in ml is 10
It was applied so that it became g/rrr and dried.

The electrostatic charge of the electrophotographic photoreceptor thus produced was measured in the same manner as in Example 1. At this time, the charging polarity was set to ten.

The results are shown below.

vo: 600 volts EIA: 3.31ux-8eC Example 32 A polyvinyl alcohol film having a thickness of 0.5 μm was formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film. Next, the disazo pigment dispersion used in Example 1 was applied onto the previously formed polyvinyl alcohol layer using a Mayer bar so that the film thickness after drying was 0.5μ, and dried to form a charge generation layer. did.

Next, 5 g of a pyrazoline compound with the structural formula and polyarylate resin (condensation polymer of bisphenol A and terephthalic acid-isophthalic acid)
A solution obtained by dissolving 5 g of the solution in 70 ml of tetrahydrofuran was applied onto the charge generation layer so that the film thickness after drying was 10 μm, and dried to form a charge transport layer.

The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 31. The results are shown in Table 4.

Table 4 Vow0610 Volt E14 + 3.71! As shown in Table 4 of ux-sec durability characteristics, the sensitivity is good (potential stability during durable use is also good).

Example 33 An ammonia aqueous solution of casein was coated on an aluminum plate with a thickness of 100 μm and dried to form a subbing layer with a thickness of 0.5 μm.

Next 2.4. 7-1-Linitro 9-Fluorenone 5
g and poly-N-vinylcarbazole (number average molecule: 13
00000) 5g to 70m of tetrahydrofuran! ! to form a charge transfer complex. This charge transfer complex compound and 1 g of the above-exemplified disazo pigment No. 2 were added to and dispersed in a solution in which 5 g of polyester resin (Vylon, manufactured by Toyobo Co., Ltd.) was dissolved in 70 ml of tetrahydrofuran. This dispersion was applied onto the undercoat layer and dried to prepare a 12 μm photoreceptor.

The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results are shown below. However, the charging polarity was set to ■.

vo: ■610V E+4: 4.1 fax-sec Example 34 The charge transport layer and charge generation layer of Example 1 were sequentially laminated on the casein layer of the aluminum base coated with the casein layer used in Example 33. A photoreceptor was formed in the same manner as in Example 1, except for the difference, and the charging characteristics were measured in the same manner as in Example 1. However, the charging polarity was set to ■.

The results are shown below.

■o20605v E each: 3.6 I! ux・sec [Effects of the Invention] The present invention uses a specific azo pigment in a photosensitive layer to improve carrier generation efficiency and/or carrier transport efficiency within the photosensitive layer containing the azo pigment. As a result, a photoreceptor with high sensitivity and excellent potential stability during long-term use can be obtained.

Claims (8)

[Claims] (1) An electrophotographic photoreceptor having a photosensitive layer on a conductive substrate, characterized in that the photosensitive layer contains a disazo pigment represented by general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) However, in the formula, R_1 represents hydrogen, an alkyl group, or an aryl group, and R_2 and R_3 represent hydrogen, an alkyl group, an alkoxy group, a halogen group, a cyano group, or a nitro group. Show, R
_2 and R_3 may be the same or different. In the formula, A and A' represent coupler residues having a phenolic OH group, and A and A' may be the same or different. (2) Claim No. (1) in which A and A' in general formula (1) of Claim No. (1) are represented by the following general formula (2):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (2) In formula (2), X is fused with a benzene ring to form a naphthalene ring, anthracene ring, carbazole ring, benzcarbazole ring, dibenzofuran ring, dibenzonaphthofuran ring, diphthalene ring, Indicates a residue necessary to form a polycyclic aromatic ring such as an enylene sulfite ring or a heterocycle. In formula (2), R_4 and R_5 represent hydrogen, an alkyl group that may have a substituent, an aryl group, an aralkyl group, a heterocyclic group, or a cyclic amino group together with the nitrogen atom to which R_4 and R_5 are bonded. (3) Claims No. (1) in which A and A' in general formula (1) of claim No. (1) are represented by the following general formula (3):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (3) R_6 in formula (3) represents an alkyl group, aryl group, or aralkyl group that may have a substituent. (4) Claims No. (1) in which A and A' in general formula (1) of claim No. (1) are represented by the following general formula (4):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (4), R_7 in formula (4) represents an alkyl group, aryl group, or aralkyl group that may have a substituent. (5) Claim No. (1) in which A and A' in general formula (1) of Claim No. (1) are represented by the following general formula (5):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (5) Y in formula (5) represents a divalent group of an aromatic hydrocarbon or a divalent group of a heterocyclic ring containing a nitrogen atom in the ring. (6) Claim No. (1) in which A and A' in general formula (1) of Claim No. (1) are represented by the following general formula (6):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (6) Y in formula (6) represents a divalent group of an aromatic hydrocarbon or a divalent group of a heterocyclic ring containing a nitrogen atom in the ring. (7) Claim No. (1) in which A and A' in general formula (1) of Claim No. (1) are represented by the following general formula (7):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (7) R_8 in formula (7) represents an aryl group or a heterocyclic group that may have a substituent, and X is X in general formula (2)
expresses the same meaning as (8) Claim No. (1) in which A and A' in general formula (1) of Claim No. (1) are represented by the following general formula (8):
The electrophotographic photoreceptor described in item 1). General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (8) In formula (8), R_9 and R_1_0 represent an alkyl group, an aryl group, an aralkyl group, or a heterocyclic group which may have a substituent. X represents the same meaning as X in general formula (2).