JPS60118843A - Photosensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body high in sensitivity, low in residual potential, and superior in durability, etc., by forming a photosensitive layer contg. a specified azo compd. stable against heat and light and superior in carrier generating ability on a conductive substrate. CONSTITUTION:An objective photosensitive body is obtained by forming on a conductive substrate a photosensitive layer contg. an azo compd. represented by formula I in which R1-R4 are each H, alkyl, or alkoxy; n is 0 or 1; Cp is one of formulae II, III, etc.; Z is an aromatic carbon ring or the like; Y is carbamoyl or the like; R5 is alkyl or the like; and A is aryl. Said compd. of formula I is embodied by formula IV in which Cp is formula V, and the compd. of formula IVis synthesized by diazotizing tetra-p-aminophenylethylene, and coupling the product with 2-hydroxy-3-(2-mehyl-4-methoxyphenylcarbamoyl)benzocarbazole.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a photoreceptor, and more particularly to a novel electrophotographic photoreceptor having a photosensitive layer containing an azo compound.

(Prior Art) Conventionally, inorganic photoreceptors having a photoconductive layer mainly composed of an inorganic photoconductive compound such as selenium, zinc oxide, sulfuric acid, etc. have been widely used. I came. However, the blades are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. In addition, cadmium sulfide has problems with moisture resistance and durability, and zinc oxide has problems with durability, etc.

In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinylcarba:/--#t2.4.7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in terms of sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with better performance by assigning the carrier generation function and the carrier transport function to different substances. Many studies have been conducted on such so-called functionally separated electrophotographic photoreceptors because each material can be selected from a wide range and a photoreceptor with arbitrary performance can be produced relatively easily. Ta.

Many compounds have been proposed as carrier generating substances for such functionally separated electrophotographic photoreceptors. An example of using an inorganic compound as a carrier generating substance is amorphous selenium described in Japanese Patent Publication No. 43-16198, which is used in combination with an organic photoconductive compound. However, the drawback that the carrier generation layer crystallizes due to heat and deteriorates the characteristics as a photoreceptor has not been improved.

(Object of the Invention) An object of the present invention is to provide a photoreceptor containing a specific azo compound that is stable to heat and light and has excellent carrier generation ability.

Another object of the present invention is to provide an electrophotographic photoreceptor with high sensitivity, low residual potential, and excellent durability whose characteristics do not change even after repeated use.

As a result of extensive research to achieve the above object, the present inventors have discovered that the azo compound represented by the following general formula [I] can function as an active ingredient of a photoreceptor, and have completed the present invention. be.

General formula [I] 3 In the formula, Bl l R2+ R4 and R4 are respectively a water purple atom, a chlorine atom (for example, a chlorine atom, a fluorine atom, a bromine atom,
iodine), an alkyl group (e.g. methyl group, ethyl group), or an alkoxy group (e.g. methoxy group, ethoxy group, etc.), where n represents an integer of 0 or 1, and in the case of 0, it is substituted with a hydrogen atom. It is assumed that there is

Cpl'1' R, R7 11 , Ra: hydrogen atom, substituted/unsubstituted alkyl group having 1 to 4 bromine atoms, substituted/unsubstituted aralkyl group, substituted/unsubstituted phenyl group, R11: Hydrogen, atoms, substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted/unsubstituted aromatic carbocyclic groups (e.g., substituted/unsubstituted phenyl groups, substituted/unsubstituted naphthyl groups, substituted/unsubstituted Anthryl group or substituted/unsubstituted aromatic heterocyclic group (e.g. substituted/unsubstituted carbazolyl group,
Represents a substituted or unsubstituted dibenzofuryl group.

Substituents for these groups include, for example, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., methyl group, ethyl group,
isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted aralkyl group (e.g. benzyl group, phenethyl group, etc.), halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom, carbon number 1 to 4 substituted/unsubstituted alkoxy groups (e.g. methoxy group, ethoxy group, impropoxy group, 5.tertiary butoxy group, 2-chloroethoxy group, etc.), hydroxy group, substituted/unsubstituted acyloxy group ( For example, p-chlorophenoxy group, l-naphthoxy group, etc.), acyloxy group (e.g., acetyloxy group, p-cyanobenzoyloxy group, etc.), carboxyl group, and its ester group (e.g., eva, ethoxycarbonyl group, m- 7” romophenoxy carbonyl group, etc.), carbamoyl group (e.g. ami7carbonyl group, tertiary butylaminocarbonyl group, anilinocarbonyl group, etc.), acyl group (
(e.g., acetyl group, 0-nitrobenzoyl group, etc.), sulfo group, sulfamoyl group (e.g., aminosulfonyl group, tertiary butylaminosulfonyl group, p-tolylaminosulfonyl group, etc.), amine group, acylamino group (e.g., acetyl (amino group, benzoylamino group, etc.), sulfonamide group (for example, methanesulfonamide group, p-toluenesulfonamide group, etc.), cyan group, nitro group, etc.; Substituted/unsubstituted argyl group (e.g., methyl group, ethyl group, isopropyl, !, n-butyl, trifluoromethyl group, etc.), halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom), number of carbon atoms 1 to 4 substituted/unsubstituted alkoxy groups (e.g., methoxy group, ethoxy group, tertiary butoxy group,
2-chloroethoxy group, etc.) cyano group, nitro group.

2 is substituted/unsubstituted aromatic carbocycle, substituted/unsubstituted w
, a group of atoms essential to form a substituted aromatic carbon ring, specifically, for example, a substituted or unsubstituted benzene ring, a substituted or substituted benzene ring,
Unsubstituted naphthalene ring, substituted unsubstituted indole ring,
Represents a group of atoms forming a substituted/unsubstituted carbazole ring, etc.

Substituents for the atomic group forming these rings include a series of substituents such as those listed as substituents for Ra + RO, but preferably halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), sulfo group, sulfo7
It is an amoyl group (for example, an aminosulfonyl group, a p-to')ylaminosulfonyl group, etc.).

Kamoke~, hydrogen atom, substituted/unsubstituted alkyl group, substituted/unsubstituted alkyl group,
Unsubstituted amino groups, carboxy groups, ester groups thereof, substituted/unsubstituted carbamoyl groups, and cyano groups, preferably hydrogen atoms, substituted/unsubstituted alkyl groups having 1 to 4 bromine atoms (for example, methyl groups, ethyl groups). /l/ group, isopropyl group,
These are a tertiary butyl group, a trifluoromethyl group, and a cyano group.

A is a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, and substituents for these groups include, for example, a series of substituted groups such as those listed as substituents for Ra+R*. However, preferably a halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom), a substituted or unsubstituted alkyl i1 having 1 to 4 carbon atoms! (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g., methquine group, ethoxy group, impropyl group) , tertiary butoxy group, 2-chloroethoxy group).

R6 and R7 are substituted/unsubstituted alkyl groups, substituted/unsubstituted Ift? A represents an aralkyl group and a substituted/unsubstituted aryl group, preferably a substituted/unsubstituted alkyl group having 1 to 4 carbon atoms (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl group, trifluoro methyl group, etc.),
Substituted/unsubstituted 7-group = A/group (e.g. Eva, phenyl group, p-methoxyphenyl group, m-chlorophenyl group, etc.)
represents.

Specific examples of the azo compound useful in the present invention represented by the general formula (1) include those having the following structural formula, but the azo compound of the present invention is not limited by this. .

a) Compound C2C having a coupler group of the following Table-A in the general formula below Table-A b) Compound having a coupler group of the following general formula cut': + followed by i-B General formula CIll) Table-B C) Compounds having the following general formula (IV) with the coupler group shown in the following Table-C General formula (■) Table-〇d) Compounds having the following general formula LV) with the coupler group shown in the following Table-D C2C A General formula [■] Table-D e) Adding the coupler group of the following Table-E to the general formula [Vl] in 1
R,OCH.

General Formula [VI] Table-E These compounds can be synthesized by well-known methods.

Synthesis Example 1 Synthesis of compound s-(1) Synthesis of iuj diphenyldichloromethane Org, Syn, Co11ective Vol. Il
, 573 (1943). Pentuphenone 136.59 (0.75 mol) and phosphorus pentachloride 1
63i (0.80 mol) was mixed and gradually heated in an oil bath. When the temperature exceeded 140°C, a sudden fever occurred. The mixture was heated as it was at a bath temperature of 140 to 150°C for 1 hour. The phosphorus oxychloride produced by the reaction was distilled off under reduced pressure, and the residue was distilled under reduced pressure. 12 degrees H9bp 169~172°
Fractions C were collected to obtain diphenyldichloroethane. 1
87g, yield 92% Synthesis of s-(l[) intermediate tetraphenylethylene O
rg, Syn, Colactive Vol, IV9
14 (1963).

Dichlorodiphenylmethane 118g (0.5mol)
and copper powder 79 jj (1.25 mol) were dispersed in benzene 400 - which had just been distilled and dehydrated, and heated under reflux for 8 hours.
Extracted with 00 rnl. The distilled liquid and the extract were combined, concentrated under reduced pressure to about 250 ml, and 500 ml of ethanol was added.

After cooling, the precipitated crystals were collected by filtration to obtain 58p of the desired intermediate tetraphenylethylene. Yield 69.8%mp2
20-222°C 8-(III) Synthesis of intermediate tetrap-nitrophenylethylene Method of John H, Gorvin (J, Chem.
Soc, 679 (1959)).

Fuming nitric acid (d=1.52) 10 ('1v, and wood vinegar m
100 mA was mixed, and tetraphenylethylene 11 was added little by little at 5 to 10°C. After reacting at room temperature for one hour, the resulting crystals were poured into ice water and allowed to crystallize from individual pieces of 〇shioki length, yielding 9.69'c of the desired tetrap-nitrophenylethylene. Yield 162% Melting point 297~
298°C Synthesis of s-(IV') Intermediate Tetra-p-aminophenylethylene Tetranyl-nitrophenylethyl: y7.75fl(
0,015 mol) was dispersed in 20 o 11 Ll of ethanol, and 15.39 (0,235 mol) of zinc powder was added to this.
I added 45 drops of concentrated hydrochloric acid. A fever developed. After the dropwise addition was completed, the mixture was further fractionated, heated under reflux, and filtered to remove insoluble matter (zinc dust). The filtrate was evaporated to dryness under reduced pressure, and the residue contained 6N-salt 11! 1t) Od to 7111. t, suspension 1. the law of nature. dM and swallowed 8.0 g of white needle crystals.

Synthesis of S-(V) Compound 1, yield 98% considering 4 HC/field of tetra-p-aminophenylethylene Tetra-p-aminophenylethylene 4HCJ salt 2.
20. A solution prepared by dissolving 1.5J7 of IJum in 10TL of water was added dropwise. After stirring for 1 hour at IAI temperature, it was quickly filtered, and 7 g of ammonium phosphorus hexafluoride was added to the filtrate. The resulting crystals were collected by filtration, washed with a small amount of water, and cooled (dissolved in 50 mA' of N,N-dimethylformamide at 0°C to -5°C and used as a dropwise solution for the coupling reaction described below). .

2-Hydroxy-3-(2-methyl-4-methoxyphenylcarbamoyl)benz(, E carbazole (naphthol ASSR manufactured by Hoechst) 6.247°triethanolamine lOp to N,N-dimethylbormamide 200m
1, and the above-mentioned dropping solution was gradually added thereto at 5°C. The mixture was stirred at the same temperature for 2 hours, returned to room temperature, and the precipitated crystals were collected. Add this to N,N-dimethylformamide 3
After washing twice with 00WLl and once with acetone 11,
Compound (1) 5. Obtained Sl. Yield 64.3%
This was confirmed by elemental analysis.

Elemental analysis (chemical formula is c+ta I91 N16 0+!
C) I N Actual value 74.68 4.72 11.15 Calculated value 7
4.85 4.58 11.08 Synthesis Example 2 Compound (7
) Synthesis of 2-hydroxy-3-(2,4-dimethylphenylcarbamoyl)naphthalene (naphthol ASMX) 4.
7 & and triethanolamine 109 to 200 N,
A coupler solution was prepared by dissolving it in N-dimethylformamide. Add to this the same dropping solution for coupling reaction (tetraaminophenylethylene 4H
2.2 oy of C7 salt (N adjustment) was poured down at 5°C. The mixture was stirred at the same temperature for 2 hours, then warmed to room temperature and left to stand. The resulting crystals were collected by filtration, washed twice with 300μ of N,N-dimethylformamide and once with 17% of acetone, and dried to obtain the desired product. 4.1 Jy+ Yield 64% This product was confirmed by elemental analysis.

Elemental analysis (Chemical formula is ClO2H, NI2 on) Element CHN Actual value 7 (i, 35 5.18 10.56 Calculated value
76.49 5. (1310,49 Synthesis Example 3 Compound (
Synthesis of 27) Synthesis of 111-dinitrotetraphenylethylene in S-(I) 10.9 of tetraphenylethylene was dispersed in 100 ml of glacial acetic acid, and nitric acid (d=1.42) 10.7 was added at room temperature.
! i' was added dropwise. Thereafter, the reaction was completed by further heating to 80°C, and 50 m2 of cooled drained water was added, and the precipitated crystals were collected by filtration and washed with a small amount of ethanol. Acquisition: 9.7F Acquisition:
Synthesis of Intermediate Diaminotetraphenylethylene 6.3% s-(11) Intermediate Dispersed in 8.44 g' of dinitrotetraphenylethylene (i=ethanol 200) and mixed with zinc powder 10. : Add l,
Concentrated hydrochloric acid AJ was added dropwise to this. A fever developed. Addition: il! to complete the reaction. After the solution was poured and allowed to cool, unreacted zinc powder was removed by filtration. Concentrate the filtrate and add 3 parts of ammonia water.
Pour into 00 ml. The precipitated crystals were collected by filtration, washed with water, and then washed with 150 ml of methanol.

Then, it is recrystallized from 250 IfLl of benzene to obtain the desired diaminotetraphenylethylene3. Obtained Og.

Yield: 41% Melting point: 253-258°C S-(111) Synthesis of compound (27) Diaminotetraphenylethylene (1.448.9%) was added to 10 ml of concentrated hydrochloric acid.
Dispersed in ice rio-. This includes 0.0% sodium nitrite.
A solution of 67p dissolved in water 5a was added dropwise. 5 after completion of dripping
The mixture was stirred for an additional 1 c''3 fJ at ~0°C and quickly filtered. 5 g of phosphorus ammonium hexafluoride was added to the filtrate, and the resulting crystals were collected by filtration to obtain a tetrazonium salt. After cooling, N- Dimethylformamide (-5~00G)
The solution was dissolved in 50ml of water and used as a dropping liquid for the coupling reaction.

8 g of 2-hydroxy-3-phenylcarbamoylnaphthalene (naphthol As, 12.J, 9.triethanolamine was dissolved in N,N-dimethylformamide 15ON to obtain a coupler solution. To this was added the above dropwise solution at 5°C. The mixture was further stirred for 2 hours at a temperature of 100°C, and then left to stand at room temperature.

The precipitated crystals were separated by dα, washed twice with 300 d of N,N-dimethylpolamide, then once with 500 d of acetone, and dried to obtain the desired product. 2.6g Yield 71% This was confirmed by elemental analysis.

Elemental analysis (Chemical formula (d C, oH42N6 04 ) Element CHN Actual value 78.93 4,84 9.33 Calculated value 79
．． 11 4.65 9.22 Among the azo compounds of the present invention, tetraazo compounds are more preferably used than diazo compounds in terms of sensitivity and stability. The formula [■] above is particularly clever.

The azo compound of the present invention has excellent photoconductivity, and when an electrophotographic photoreceptor is manufactured using the azo compound, a photosensitive layer containing the azo compound of the present invention dispersed in a binder is formed on a conductive support. It can be manufactured by providing. Another method is to use the azo compound of the present invention as a carrier-generating substance that takes advantage of its particularly excellent carrier-generating ability among its photoconductivity properties, and to use it together with a carrier-transporting substance that can effectively act in combination with the photoconductivity. It is also possible to make a so-called functionally separated electrophotographic photoreceptor, such as a laminated type or a dispersed type. Further, the azo compound used in the present invention can be used alone or in combination of I'i2,9 or more from among the azo compounds represented by the above general formula [I], and
It may also be used in combination with other azo compounds.

Various mechanical configurations of electrophotographic photoreceptors are known, and the electrophotographic photoreceptor of the present invention can take any of these forms.

Usually, the configuration is as shown in FIGS. 1 to 6. In FIGS. 1 and 3, a laminate is formed of a carrier generation layer 2 containing the above-mentioned azo compound as a main component and a carrier transport layer 3 containing a carrier transport substance as a main component on a conductive support l. A photosensitive layer 4 is provided.

As shown in FIG. 2 and FIG. 4, this photosensitive layer 4 has dl
= May be provided via an intermediate N5 provided on the bloody support. When the photosensitive layer 4 has a two-layer structure as described above, an electrophotographic photosensitive material having the best electrophotographic A% property can be obtained. In the present invention, as shown in Figures #J5 and 6, the carrier generating substance 7 is dispersed in JWt 6 whose main component is a carrier transporting substance. The photosensitive layer 4 may be provided directly on the conductive support 1 or via an intermediate layer 5.

When the azo compound of the present invention is used together with a carrier-generating substance, examples of the carrier-transporting substance used in combination with the azo compound include electron-accepting substances that easily transport electrons, such as trinitrofluorenone or detranitrofluorenone, as well as photoIJ- Polymers having a chain of heterocyclic compounds such as N-vinylcarbazole, triazole conductors, oxadiazole derivatives, imitazole derivatives,
Electron-donating materials that easily transport holes, such as pyrazoline derivatives, polyarylars, lucan derivatives, phenylenediamine derivatives, hydrazone conductors, amino-substituted chalcone conductors, triarylamine conductors, carbazole derivatives, stilbene derivatives, etc. However, the carrier transporting material used in the present invention is not limited to these materials. It can be formed directly or, if necessary, by providing an intermediate layer such as an adhesive base or a barrier layer, for example, by the following method.

M-i) A solution of an azo compound dissolved in a suitable solvent,
Alternatively, a binder may be added as necessary and a mixed and dissolved solution may be applied.

M-2) A method in which an azo compound is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a binder is added thereto as required to ensure safety. A mixed and dispersed dispersion is applied.

The wetting medium or dispersion medium used for forming the carrier generation layer includes n-butylamine, diethylamine, ethylenediamine, impropaturamine, triethanolamine, triethylenediamine, N,N-dimethylpolamide, acetone, methylethylketone, and cyclohexanone. , benzene, toluene, quinolene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, ethanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, and the like.

When using a binder in the carrier generation layer or carrier transport layer, any binder can be used. It is preferable to use Examples of such high molecular weight polymers include, but are not limited to, the following.

p-1) Polycarbonate p-2) Polyester p-3 Methacrylic resin p-4) Acrylic resin p-5) Polyvinyl chloride p-6) Polyvinylidene chloride p-7) Polystyrene p-8) Polyvinyl acetate p-9 ) Styrene-butadiene copolymer p-10) Pinyritene chloride-acryloni)! Jru copolymer-11) Vinyl chloride-vinyl acetate copolymer p-12)
For conversion to m: Ni-vinyl acetate-maleic anhydride copolymer p-13) Silicone side material P-14) Silicone-alkyd resin p 15) 7
'-1-Nol-formaldehyde side fat p-16) Styrene-alkyd resin p-17) Poly-N-vinylcarbazole p-18) Polyvinyl butyranano These binders may be used alone or in a mixture of two or more. It can be used as

The thickness of the carrier generation layer 2 formed in this way is
Although it is convenient that the thickness is from 0.01 μm to 20 μm, it is more preferably from 0.05 μm to 5 μm. Also, if the carrier generation layer or photosensitive layer is a dispersion system, what is the particle size of the azo compound? 'i is preferably 5 μm or less, more preferably 1 μm or less.

Examples of the conductive support used in the Haji photographic photoreceptor of the present invention include gold striped plates including alloys, metal drums or conductive polymers, aluminum including conductive compounds and alloys such as indium oxide, palladium, gold, etc. Apply a thin metal layer of
Examples include plastic films and plastic films that have been made conductive by vapor deposition or lamination. For the intermediate layer such as the adhesive or rear layer, in addition to the polymer monomer used as the binder, a flexible polymer material such as polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, or aluminum oxide is used. .

The electrophotographic A photoreceptor of the present invention has the above configuration,
As is clear from the examples described later, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and particularly shows little deterioration even after repeated use and is excellent in durability.

The azo compound of the present invention is Ichikawa's compound whose conductivity changes upon irradiation with light, and it can be used not only in electrophotographic Ag photoreceptors but also in any photoreceptor that utilizes this property.

Examples of the present invention will be specifically described below, but the embodiments of the present invention are not limited to kneading.

Example 1 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer “Eslec MF-10J”
(manufactured by Tanezu Kagaku Co., Ltd.) with a thickness of 0.05 μm, and 1.2-
Dichloroethane 110ILL7! After drying the dispersion, which was mixed with
A carrier-generating layer was formed by coating the film in such a manner as to form a carrier-generating layer. On top of this carrier generation layer, a solution of 6 g of 4-methoxy-4'-styryltriphenylamine and 1 M of methacrylic resin (Mitsubishi Rayon Co., Ltd.) in 70 rnl of 1,2-dichloroethane was applied to the film after drying. Thickness is 1
A carrier transport layer is formed by coating to a thickness of 0 μm,
An electrophotographic photoreceptor of the present invention was prepared.

The photoconductor produced in this way was used in an electrophotographic copying machine (U
-Bix 20 (HJ tt J (manufactured by Konishiroku Photo Industry)
When the device was installed on a modified machine and the image was copied, a clear copy image was obtained. This did not change even after repeating 5000 times.

Example 2 On the conductive support provided with the intermediate layer used in Example 1, 2 g of exemplified compound (3) and 10 g of 1,2-dichloroethane were placed.
0rn7! are well dispersed and mixed so that the film thickness after drying is 0.
A carrier generation layer was created by coating the film to a thickness of 3 μm.

Next, as a carrier transport substance, a solution prepared by bathing 611 (compound CK-1 below) and polycarbonate 1 Panlite L-1250J (manufactured by Kijin Kasei Co., Ltd.)-1 10p in 90 g of 1,2-dichloroethane was then added as a carrier transport substance. A carrier transport layer was formed by coating to a film thickness of 10 μrnVC after drying, and an electrophotographic photoreceptor of the present invention was prepared.

The electrophotographic properties of this electrophotographic photoreceptor at room temperatures of 23° C. and 60° C. were measured using a 5P-428 type IL paper tester (manufactured by Kawaguchi Denki Seisakusho), and the results are shown below.

As is clear from the results in Table 1 and above, the electrophotographic photoreceptor of the present invention has good sensitivity and residual potential characteristics even when exposed to high temperatures, and is stable against heat.

Example 3 Exemplary compound (8) 2 & and 1,2-dichloroethane 110 were placed on the conductive support provided with the intermediate layer used in Example 2.
A carrier generation layer was prepared by thoroughly dispersing and mixing and applying the mixture so that the film thickness after drying was 0.3 μmK.

For this carrier generation layer, place an ultra-high pressure mercury lamp (manufactured by Tokyo Shibaura Electric Co., Ltd.) at a position 3 ocIILM apart, and
UV light of 1500 cdΔ was applied for a minute. Next, the following compound (K-2) 7&, polycarbonate [Hanlite L-1250'], (Teijin Kasei M) 11 was applied as a carrier transport substance on the carrier generation layer that had been irradiated with UV light. 1.2~Dichloroethane (K-2) A solution dissolved in 90y was coated to form a carrier transport layer so that the film thickness after drying was 12 μm, thereby producing an electrophotographic photoreceptor of the present invention.

The same measurements as in Example 2 were performed on this electrophotographic photoreceptor. The results are shown in Table 2.

Example 4 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 3, except that UV light was not irradiated after the carrier generation layer was formed.
The same measurements as in Example 3 were performed.

The results are shown in Table 2.

As is clear from the results shown in Table 2, the electrophotographic photoreceptor of the present invention has excellent sensitivity and residual potential characteristics to UV light irradiation, small fluctuations in acceptance potential, and high resistance to light. It can be understood that it is stable.

Example 5 Diameter with the intermediate layer used in Example 1 provided on the surface] 00
1 of compound (23) on an aluminum drum of VRA.
% ethylenediamine/Film thickness after drying the solution is 0.3μm
A carrier-generating layer was formed by layering the two layers to form a carrier generation layer. Next, the following compound CK-3) 61/ and 10 g of polyester resin "Vylon 200J (manufactured by Toyo iVjM)" were added thereon.
was dissolved in 70 d of 1,2-dichloroethane, and this solution was coated to form a carrier transport layer such that the film thickness after drying was 11 μm, thereby producing an electrophotographic photoreceptor of the present invention.

When the drum-shaped photoreceptor thus obtained was installed in a modified electrophotographic copying machine r U-BIX v2J (manufactured by Konishi Rokuyoshin Kogyo) and an image was copied, a clear image with high contrast was obtained. It was done.

(K-3)

[Brief explanation of drawings]

1 to 6 are sectional views showing examples of the mechanical structure of the electrophotographic photoreceptor of the present invention, and numbers 1 to 7 in the figures represent the following, respectively. 1... Conductive support, 2... No carrier generation, 3... Carrier transport layer, 4... Photosensitive layer, 5... - Intermediate layer, 6... Layer containing a carrier transport substance, 7...
...Carrier-generating substance. Agent Yoshimi Kuwahara

Claims (1)

[Scope of Claims] ]) A photoreceptor having a photosensitive layer containing an azo compound represented by the following general formula (1) on an electrostatic support. General formula [■] [In the formula, RI + "2 + R3 + R4 each represents a hydrogen atom, an alkyl group, or an alkoxy group,
n represents an integer of O or 1, and in the case of O, water C
p is 8R, R) 1 H, 2: atomic group necessary to constitute a substituted/unsubstituted aromatic carbocycle or substituted/unsubstituted aromatic heterocycle, y: i-substituted/unsubstituted Carbamoyl base or substitution/non-i!
sulfamoyl group, Rs dihydrogen atom substituted/unsubstituted alkyl group, substituted/unsubstituted amine group, substituted/unsubstituted carbamoyl group, carboxy group and its ester group, or cyano group, ^: substituted/unsubstituted Substituted aryl group, R6 and at: Represents a substituted/unsubstituted alkyl group, substituted/unsubstituted aral, kyl group, or substituted/unsubstituted aryl group. ] 2) The photosensitive layer contains a carrier-transporting substance and a carrier-generating substance, and the carrier-generating substance is represented by the general formula [■]
The photoreceptor according to claim 1, which is an azo compound represented by: