JPS60111252A - Photosensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body high in sensitivity, low in residual potential, unchangeable in these characteristics even in repeated uses, and superior in durability by incorporating in a photosensitive layer a specified bisazo compd. stable against heat and light and superior in carrier generating ability. CONSTITUTION:A carrier generating layer 2 composed essentially of a bisazo compd. represented by general formula [ I ], and a carrier transfer layer 3 composed essentially of a carrier transfer material are laminated on a conductive substrate 1 to form a photosensitive layer 4. In formula [ I ], A is optionally substd. alkyl or aryl; R is H, alkyl, alkoxy, or halogen; and Cp is one of groups of formulae II-V. An electrophotographic sensitive body having the best electrophotographic characteristics can be obtained by thus forming the photosensitive layer composed of 2-layer structure. When the bisazo compd. of this invention is used for a carrier generating material, as a carrier transfer material to be used in combination with it, an electron acceptor capable of easily transferring electrons, such as trinitrofluorenone or tetranitrofluorenone, as well as an electron donor capable of transferring positive holes, such as polymers having on the side chains a heterocyclic compd. typified by poly-N-vinylcarbazole, are favorably used.

Description

[Detailed Description of the Invention] (Industrial Application Field) The present invention relates to a photoreceptor, and more specifically to an azo compound. i! The present invention relates to a novel electrophotographic photoreceptor having a photosensitive layer containing I.

(Prior Art) Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, or cadmium sulfide as a main component have been widely used as photoreceptors. However, these are not necessarily satisfactory in terms of sensitivity, mature quality, 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. Additionally, 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 Kfl poly-19-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning carrier-generating functions, carrier-transporting functions, and materials to metals. Such a so-called functionally separated electrophotographic photoreceptor has been the subject of much research because each material can be selected from a wide range and a photoreceptor with arbitrary performance can be produced relatively easily. has been done.

Many compounds have been proposed as carrier-generating substances in such a functionally separated photoreceptor. An example of using an inorganic compound as a carrier generating substance is amorphous selenium, which is described in Japanese Patent Publication No. 16198/1982, and is used in combination with an organic photoconductive compound. The disadvantage that the carrier generation layer made of regular selenium crystallizes due to heat and deteriorates the characteristics as a photoreceptor has not been improved.

Furthermore, many electrophotographic photoreceptors using organic dyes or organic pigments as carrier-generating substances have been proposed. For example, as an electrophotographic photoreceptor containing a bisazo compound or a trisazo compound in the photosensitive layer, JP-A-54-12742, JP-A-57-74746, JP-A-53-9
No. 5033, etc. are already known. However, these bisazo compounds or trisazo compounds are not necessarily satisfactory in terms of sensitivity, residual potential, or stability during repeated use, and the selection range of carrier transport substances is also limited. It does not fully satisfy the wide range of process requirements.

Furthermore, in recent years, Ar laser, He −
Gas lasers such as Nθ lasers and semiconductor lasers are beginning to be used. A feature of these lasers is that they can be turned on and off in chronological order, and if! It is particularly promising as a light source for copiers and computer output printers that have 1iflJ processing functions. Among these, semiconductor lasers are attracting attention because their nature does not require electrical signal/original signal conversion elements such as acousto-optic elements, and they can be made smaller and more compact. However, this semiconductor laser has a low output power compared to a gas laser, and the oscillation wavelength is also long (approximately 780 nm or more), so the spectral sensitivity of conventional photoreceptors is too high on the short and long sides, and this remains the case. Therefore, it is impossible to use it as a photoreceptor using a semiconductor laser as a light source.

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

An 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.

A further object of the present invention is to provide an electrophotographic photoreceptor containing a disazo compound which can effectively act as a carrier generating substance even in combination with a wide variety of carrier transporting substances.

A further object of the present invention is to provide a photoreceptor that has sufficient practical sensitivity even to surface wavelength light sources such as semiconductor lasers.

Further objects of the present invention will become clear from the description in the specification.

(Structure of the Invention) As a result of intensive research to achieve the above object, the present inventors discovered that a disazo compound represented by the general formula [I] 'F can function as an active ingredient of a photoreceptor. , has completed the present invention.

In the formula, the person represents a substituted or unsubstituted alkyl group (e.g. ethyl group,
globyl group, pentyl group, methoxyethyl group, hydroxyethyl group, benzyl group, phenethyl group, etc.) or substituted/substituted aryl group (e.g. evaphenyl group, p-methylphenyl group, 2,4-dimethylphenyl group, methoxy phenyl group, chlorophenyl group, etc.), and R represents a hydrogen atom, an alkyl group (e.g., methyl group, ethyl group, etc.), an alkoxy group (e.g., methoxy group, ethoxy group, etc.), or a halogen atom (e.g., fluorine, chlorine, bromine). represents.

R4: a hydrogen atom, a substituted/unsubstituted alkyl group with a carbon number of ~4, a substituted/unsubstituted aralkyl group, a substituted/unsubstituted phenyl group, R6: a hydrogen atom, a carbon number of J~4 Substituted/unsubstituted alkyl groups, substituted/unsubstituted aromatic carbocyclic groups (e.g., substituted/unsubstituted phenyl groups, substituted/unsubstituted naphthyl groups, substituted/unsubstituted anthryl groups, etc.), and 1- Fit-substituted/unsubstituted aromatic groups (e.g. substituted/unsubstituted aromatic groups)
unsubstituted carbazolyl group, substituted/unsubstituted dibenzofuryl group, etc.].

Substituents for these groups include, for example, substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., methyl group, ethyl group,
Inglovir group, tertiary buty/l'&, trifluoromethyl group, etc.), substituted/unsubstituted aralkyl groups (e.g. benzyl group, phenethyl group, etc.), halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom) ), carbon number] to 4 substituted/unsubstituted alkoxy groups (e.g. methoxy group, ethoxy group, impropoxy group, tertiary butoxy group, 2-chloroethoxy group, etc.), hydroxy group, substituted/unsubstituted aryloxy groups (e.g., p-chlorophenoxy group, 1-naphthoxy group, etc.), acyloxy groups (e.g., acetyloxy group, p-cyanobenzoyloxy group, etc.), carboxyl groups, ester groups thereof (e.g., ethoxycarbonyl group, m -bromophenoxycarbonyl group, etc.), carbamoyl group (e.g., aminocarbonyl group, tertiary butylaminocarbonyl group, anilinocarbonyl group, etc.), acyl group (
(e.g., acetyl group, 0-nitrobenzoyl group, etc.), sulfo group, sulfamoyl group (e.g., aminesulfonyl group, tertiary butylaminosulfonyl group, p-tolylaminosulfonyl group, etc.), amino group, acylamino group (e.g., acetyl amino group, benzoylamino group, etc.), sulfonamide group (e.g., methanesulfonamide s, p
-) a sulfonamide group, etc.), a cyano group, a nitro group, etc., but preferably a substituted group having 1 to 4 carbon atoms,
Unsubstituted alkyl group (e.g. methyl group, ethyl group, isopropyl group, n-butyl group, trifluoromethyl group, etc.)
, halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (
For example, methoxy group, ethoxy group, tertiary butoxy group, 2
-chloroethoxy group, etc.) cyano group, nitro group.

2 is an atomic group necessary to form a substituted/unsubstituted aromatic carbocycle or a substituted/unsubstituted aromatic heterocyclic it shadow,
Specifically, it represents an atom # forming a substituted/unsubstituted benzene ring, a substituted/unsubstituted naphthalene ring, a substituted/unsubstituted indole ring, a substituted/unsubstituted carbazole ring, etc.

Examples of substituents for the atomic group forming these monkeys include a series of substituents such as those listed as substituents for R, R, and preferably halogen atoms (chlorine, bromine, fluorine, etc.). atom, iodine atom), a sulfo group, and a sulfamoyl group (for example, an aminosulfonyl group, a p·-tolylaminosulfonyl group, etc.).

R, d, hydrogen atom, substituted/unsubstituted alkyl group, substituted/
An unsubstituted amino group, a carboxyne group, an ester group thereof, a substituted/unsubstituted carbamoyl group, a cyano group, preferably a water purple atom, a substituted/unsubstituted alkyl group having 1 to 4 carbon atoms (for example, a methyl group) , ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), and cyano group.

A' is a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, and examples of substituents for these groups include a series of substituents such as those for R, R, and the like. Preferably, halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms (for example, methyl group, ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), and substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (eg, methoxy group, ethoxy group, ingropoxy group, tertiary butoxy group, 2-chloroethoxy group).

R7 and R8 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralgyl group, or a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms (for example, methyl group, ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted
Represents an unsubstituted phenyl group (eg, phenyl group, p-methoxyphenyl group, m-chlorophenyl group, etc.).

That is, in the present invention, by using the disazo compound represented by the above general formula / [■] as a photoconductive substance constituting the photosensitive layer of the photoreceptor, the object of the present invention is to achieve stability against heat and light. It also has excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and shows little fatigue change even after repeated use.
An excellent photoreceptor having sufficient g even in a long wavelength region of 80 nm or more can be produced.

Among the disazo compounds represented by the general formula CI) used in the present invention, the following general formula [11
) is the general formula [■] λ Specific examples of the disazo compound useful in the present invention represented by the general formula CI) and [I[] include those having the following structural formula. However, the disazo compound of the present invention is not limited thereby.

A-(11 to (33) General formula [■] 4 (Formula [■] I and the table below (In R of Al, the number indicates the bonding position of the substituent R.) Table -(A) A -(33' ) to (37) Table - (El These compounds can be synthesized by a combination of conventional and well-known methods. Synthesis examples are shown below.

Synthesis Example 1 (Synthesis of Exemplified Compound A-(2)) 1] Intermediate Synthesis of Dinitrophenothiazine 0, Bodea,
M, Ra1leau's method (C!hem, Abst, V
o154゜22657 F (Synthesized according to 1960. That is, dissolve in a mixed solution of 2511 ft of phenothiazine, 600 d of chloroform, and 50 ml of glacial acetic acid,
To this was added 25 g of sodium nitrite in portions over 1 hour.

After the addition, the mixture was further stirred for 2 hours, and the resulting crystals were collected by filtration and thoroughly washed with methanol and then water. This thing i DMF
Recrystallized from (N,N-dimethylformamide),
Intermediate dinitrofetch adi/14 g was obtained. (yield 3
8,6) 2) Synthesis of medium INI form N-P-tolyldinitrophenothiazine Dinitrophenothiazine 8.71 and p-iodotoluene 10.9? Mix with 50 parts of nitrobenzene, add 0.5 parts of potassium carbonate 8I copper powder,! ? was added and reacted at 210°C to 220°C for 10 hours. After the reaction, steam distillation ICj removes nitrobenzene and the remaining p-
The iodotoluene was distilled off, and then the crude crystals were collected by filtration.

Chloroform]651 was added thereto, and the O2 extract extracted while hot was filtered through silica gel (200 mesh) 50F, and the filtrate was evaporated to dryness. Suspension and wash the remaining residue with ethyl acetate, then purify with methanol and fc. Further washing with water and then methanol yields the desired intermediate N-p-)
Red crystals of lyldinitrophenothiazine 5.1Fe were obtained.

Yield 45% Melting point 185-188°C 3) Intermediate Synthesis of 2.7-diami2-10-tolylphenothiazine Exemplary Compound (2) The mixture became cloudy, and 40 g of gold stannous chloride (dihydrate) was added thereto, and the mixture was heated under reflux for 3 hours.

After cooling, the crystals were filtered and washed with dilute hydrochloric acid to obtain a 2,7-diami2-10-tolylphenothiazine-tin complex. (
(Melting point 195-200°C) All of the above diamino body-tin complex fil Hydrochloric acid 20m Water 15
A solution prepared by dissolving 1.5 g of sodium nitrite in 10 yards of water was added dropwise at -5°C.

After the dropwise addition was completed, the mixture was stirred at the same temperature for 1 minute, and immediately filtered.
To the obtained filtrate was added hexafluorophosphorus ammonium 1011' (
f and the resulting crystals were collected by filtration to obtain tetrazonium hexafluorophosphate. The crystals were dissolved in 100 i/l of N,N-dimethylformamide and used as a dropwise solution for the next coupling reaction.

Next, 17.0 g of 2-hydroxy-3'-(4-methoxyphenylcarbamoyl)-benzo[a]carbasol (naphthol As-8G, manufactured by Hoechst) and 1 liter of triethanolamine (300 a of N,N-dimethyl The solution was dissolved in formamide, and the above tetrazonium salt solution was added dropwise thereto while cooling with ice at 5'C.

After stirring at the same temperature for 2 hours, the mixture was allowed to stand overnight at room temperature, and the resulting crystals were collected by filtration. This crystal was heated to 300-〇N,
After washing twice with N-dimethylformamide and twice with acetone No. 11, it was dried to obtain Exemplified Compound A-(2).
4.8#″f!: Obtained.

The yield of this compound was 43% (from the dinitro form), which was confirmed by photometric analysis.

(Chemical formula is C1l? H4? HO06S 1 element C
HNS Actual value (%) 72.49 4.36 11.35 3
．． 15 Calculated value (%) 72,74 4.2B 11.4
0 2.90 Synthesis Example 2 (Synthesis of Exemplified Compound A-(3)) 1) Synthesis of Intermediate N-Ethyldinitrophenothiazine 5.8 g of dinitrophenothiazine was suspended in 200 g of A7, and 8 g of potassium carbonate was added to it. .4 Il diethyl sulfate 7.2.9'Th was added, and the mixture was heated under reflux for 10 hours. After the reaction, 10,011 L of acetone was distilled off, then 100 L of water was added, and the crystals were collected by filtration. Wash with water, then methanol 1
Sufficient suspension washing was carried out in a mixture of 00 ml, water, 201 nl, and 5 I of sodium hydroxide to obtain 5.8.91 N-ethyldinitrophenothiazine, excluding unreacted raw materials. (Melting point 2
15-216°C Yield 91%) 2) Intermediate Synthesis of 0-ethyl-2,7-diamitphenothiazine N-ethyldinitrophenothiazine 6.34Ii'tN
, dissolved in 100 rttl of N-dimethylformamide,
To this was added 10 Ii of iron, 10 -5 water and 2 mJ = Jy of hydrochloric acid, and the mixture was heated at 105 to 110°C for 1 hour. After the reaction, a suspension of IJum 3I in 15 m/Ic of water was added and filtered while hot.

To the filtrate were added 500 grams of ice water, 10 grams of ice water, and 40 grams of water. The resulting crystals were collected by filtration, washed with water, and then evaporated to dryness with the addition of hydrochloric acid to give a hydrochloride.

Yield i3 & (yield 42% as ternate salt) Melting point 250'C
(Decomposition) 3) Synthesis of Exemplary Compound A-(3) 10-ethyl-2,7-diamitufenothiazine hydrochloride 3.68#t'' hydrochloric acid 10 FILl, water 60111
Step 7: Dispersion, add 1.7 g of sodium nitrite to 1 liter of water.
- was added dropwise at -5°C. After the dripping is finished,
The mixture was stirred at the same temperature for 10 minutes, and immediately filtered. 1 (l) of ammonium hexafluorophosphate was added to the resulting filtrate, and the resulting crystals were collected by filtration to obtain tetrazonium hexafluorophos 7ate. This crystal was dissolved in N,N-dimethylformamide ioo 1 nJ! to obtain a dropwise solution for the next coupling reaction.

2-Hydroxy-3-naphthoic acid anilide (naphthol As) 5.2711'fry was dissolved in 200a of N-dimethylformamide, and to this was added 6Og of triethanolamine. Next, this liquid-resistant liquid was cooled to 5° C., and while stirring vigorously, the above-mentioned dripping liquid was fractionated thereto. After the dropwise addition was completed, the mixture was stirred for about 1 hour, then warmed to room temperature and left overnight. The resulting crystals were collected by filtration, washed twice with 500 ml of dimethylformamide and once with 1 ml of acetone, and then dried to obtain 3.1 g of an evening-colored compound. Yield: 19% This compound was confirmed by photometric analysis.

Elemental analysis results (chemical formula: 04.H,, 048N, )
Element CHN S Actual value (ch) 71.35 4.5i 12.38 4
．． 10 Calculated value (%) 7], 53 4.38 12.1
7 3.98 The disazo compound of the present invention has excellent photoconductivity, and when it is used to manufacture an electrophotographic photoreceptor f,
It can be produced by providing on a conductive support a photosensitive layer in which the disazo compound of the present invention is dispersed in a total binder. Another method is to use the disazo compound of the present invention as a carrier-generating substance that takes advantage of its particularly excellent carrier-generating ability among its photoconductivity, and to use it together with a carrier-transporting substance that can effectively act in combination with this. Accordingly, it is also possible to make a so-called functionally separated electrophotographic photoreceptor, such as a laminated type or a dispersed type. Further, the disazo compound used in the present invention can be used alone or in combination of two or more of the disazo compounds represented by the general formula (I), and can also be used in combination with a disazo or triazo compound. Good too.

Various mechanical configurations of electrophotographic photoreceptors are known, and the electrophotographic photoreceptor of the present invention can be based on any of them.

Usually, the configuration is as shown in FIGS. 1 to 6. In FIGS. 1 and 3, a carrier generation layer 2 containing the above-mentioned disazo compound as a main component and a carrier transport layer 3 containing a carrier transport substance as a main component are formed on a conductive support 1. A photosensitive layer 4 made of a dipping layer is provided. As shown in FIGS. 2 and 4, this photosensitive layer 4 may be provided via an intermediate layer 5 provided on a conductive support. When the photosensitive layer has a two-layer structure with a thickness of 4'ft, an electrophotographic photoreceptor having the most excellent electrophotographic properties can be obtained. In addition, in the present invention, the fifth
As shown in FIG. 6 and FIG. 6, a photosensitive layer 4 consisting of a carrier-generating substance 7 dispersed in a layer 6 containing a carrier-transporting substance as a main component is deposited directly on a conductive support 1 or as an intermediate layer 5' ( When the disazo compound of the present invention is used as a carrier-generating substance, an electron-accepting substance that easily transports electrons such as trinitrofluorenone or tetranitrofluorenone can be used as a carrier-transporting substance to be used in combination with the disazo compound of the present invention. In addition to chemical substances, polymers having a heterocyclic compound in the side chain such as -N-vinylcarbazole, triazole derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, polyarylalkane derivatives, and phenylenediamines - conductor, hydrazone derivative,
Examples include electron-accepting substances that easily transport holes, such as amine-substituted alkone derivatives, triarylamine derivatives, carbazole derivatives, and stilbene derivatives, but the carrier-transporting substances used in the present invention are not limited to these. .

Two-layer photosensitive layer 4'ff - carrier generation layer 2
can be formed directly on the conductive support 1 or the carrier transport layer 3, or on an intermediate layer such as an adhesive layer or a barrier layer as required, for example, by the following method.

M-1) A method of coating a solution of a disazo compound in an appropriate solvent, or a solution prepared by adding a binder as necessary and dissolving the mixture.

M-2) A method in which a disazo compound is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a binder is added as necessary to mix and disperse the resulting dispersion and then applied.

U, n-butylamine, diethylamine, ethylenediamine, inglobanolamine, triethanolamine, triethylenediamine, N,N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, as a solvent or dispersion medium used for forming the carrier generation layer. Benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, etc.

When using a binder in the carrier generation layer or the carrier transporting layer, it is necessary to use Ninhui's binder, which is an electrically insulating film-forming polymer that is hydrophobic and has a high dielectric constant. It is preferable to use Examples of such high molecular weight polymers include the following:
It is not limited to these.

P-1) Polycarbonate P-2) Polyester P-3) Methacrylic resin P-4) Acrylic resin P-5) Polyvinyl chloride P-61 Polyvinylidene chloride P-71 Polystyrene P-8) Polyvinyl acetate P-9) Styrene -Butadiene copolymer P-101
Vinylidene chloride-acrylonitrile copolymer P-111 Vinyl chloride-vinyl acetate copolymer P-1
21 Vinyl chloride-vinyl acetate-maleic anhydride copolymer P -131 Silicone resin P -14+ Silicone-alkyd resin P -, 15
) phenol-formaldehy)” It fat p −
161 Styrene-Alkyd Resin P-171 Poly-N
-Vinylcarbazole p-18) Polyvinyl butyral These binders can be used alone or as a mixture of two or more.

The thickness of the carrier generation layer 2 formed in this way [,
It is preferably 0.01 μm to 20 μm, more preferably Fio, 0.05 μm to 5 μm. Further, when the carrier generation layer or the photosensitive layer is a dispersed type, the particle size of the azo compound is preferably 5 μm or less, more preferably 1 μm or less.

The conductive compounds used in the electrophotographic photoreceptor of the present invention include metal plates, metal drums, or conductive polymers including two alloys, metals such as aluminum, palladium, and gold including conductive compounds and alloys such as indium oxide. Apply a thin layer,
Examples include paper, glass film, etc. that have been made conductive by vapor deposition or lamination. As an intermediate layer such as an adhesive layer or a barrier layer, organic polymer materials such as polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, aluminum oxide, etc. are used in addition to the polymer used as the binder.

The Seiko photosensitive body of the present invention has the above structure,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and planning formation characteristics, and particularly shows little fatigue deterioration even after repeated use, and has poor durability.

The present invention will be specifically explained below using Examples, but the embodiments of the present invention are not limited thereto.

(Example) Example 1 Exemplary compound A- (312 g and polycarbonate fat
Panlite L-1250J (Hitsuiri Kaseisha W) 2g and 11
．． The mixture was added to 110 ml of 2-dichloroethane and dispersed in a ball mill for 12 hours. This dispersion was applied as a heel carrier generation layer on a polyester film fully deposited with aluminum so that the dry film thickness was 1 μm, and further on top of this was applied as a carrier transport layer (in the following structural formula -(1 )16g
Polycarbonate resin "Panlite L-1250J"
1. A solution prepared by dissolving Og and 1,2-dichloroethane in 110 ml of 1,2-dichloroethane was coated to give a film thickness of 15 μm after drying to form carrier transport l-, thereby producing an electrophotographic photoreceptor of the present invention.

K-(]) The photoreceptor obtained as described above was subjected to the following temporal evaluation using an electrostatic paper tester SP-428, m manufactured by Kawaguchi Electric Seisakusho. After charging for 5 seconds at a charging voltage of −□KV,
Leave it in the dark for 5 seconds, then reduce the illuminance on the photoreceptor surface to 351u.
Exposure amount required to attenuate the surface potential by half by irradiating the source of the halogen lamp so that x (half-reduced exposure amount) E
I hung up my knife. In addition, the surface potential (residual position) VR'ir after exposure with an exposure amount of 301 and ux-sec was determined. Further, similar measurements were repeated 100 times. The results are shown in Table 1.

Table 1 Comparative Example 1 The following -disaso compound (G-
1+ was used in the same manner as in Example 1 (G-11) This comparative photoreceptor was measured in the same manner as in Example, and the results are shown in Table 2. Got the results.

As is clear from the results in Table 2 and above, the electrophotographic photoreceptor of the present invention is extremely superior in sensitivity, residual potential, and stability over 9 cycles compared to the comparative electrophotographic photoreceptor.

Example 2 Vinyl chloride-vinyl acetate-
A 0.05 μm thick intermediate layer made of maleic anhydride copolymer [S-LEC MF-1og (manufactured by Tanezu Kagaku Co., Ltd.) was provided, and exemplified compound A-(9) 2g'l-1.2-dichloro The dispersion was mixed with 110 ml of ether and dispersed in a ball mill for a while and then dried and coated to a film thickness of 0.5 μm to form a carrier generation layer. On this carrier generation layer, 4-methothenthicitriphenylamine 69 and methacrylic resin "Acrivet" (Mitsubishi Rayon Co., Ltd. ff) 1019 and '? ], 2-dichloroethane 70
A carrier transport layer was formed by coating a solution obtained by fermenting M into a film having a dry film thickness of 10 μm, thereby completing the entire electrophotographic photoreceptor of the present invention.

The same measurements as in Example 1 were performed on this electrophotographic photoreceptor, and for the first time, E+ = 2.51ux -
sea, VR=OV results were obtained.

Example 3 On the conductive support provided with the intermediate layer used in Example 2,
A 1% ethylenediamine solution of Exemplified Compound A-(29) was applied so that the film thickness after drying was 0.3 μm to form a carrier generation layer.

Next, the above compound (x-216g and polyester resin [Pylon 200J (manufactured by Toyobo Co., Ltd.) 10g and a tube] was then placed on top of it.

The electrophotographic photoreceptor of the present invention was prepared by dissolving 2-dichloroethane at 70 mJK and applying this solution to a dry film thickness of 12 μm to form a carrier transport layer.

Regarding this electrophotographic photoreceptor, Table 3 is similar to Example 1. Example 4 A carrier generation layer was formed in the same manner as in Example 3 except that Exemplified Compound A-(29) was replaced with Exemplified Compound A-(111). On top of this, 6.9 g of (K-31 compound (K-3)) and 10 g of polycarbonate [Panlite I, -1250J (manufactured by Yondai Kasei Co., Ltd.) were added.
A carrier transport layer was formed by coating a solution dissolved in 70 ml Km of 1,2-dichloroethane so that the film thickness after drying was 10 μm, and the entire electrophotographic photoreceptor of the present invention was prepared.

When this electrophotographic photoreceptor was measured in the same manner as in Example 1, y = 3.11 uX-8et and VR = OV.

Example 5 A vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC my-10J (manufactured by A-Sui Kagaku Co., Ltd.) with a thickness of 0.05 mm was coated on the surface of an aluminum drum with a diameter of 100 mm.
A μm-thick intermediate layer is provided thereon, and exemplified compound (2) 4I!
mixed with 400 IIL of 1,2-dichloroethane,
A dispersion obtained by dispersing the latent time using a ball mill was applied so that the film thickness after drying was 0.6 μm to form a carrier generation layer.

Furthermore, on top of this, (the following compound K-430F and polycarbonate resin [Corbilon s-]ooo J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 5011 and t-1,2-dichloro 4oo
A carrier transport layer was formed by dissolving mtvc and coating it to a film thickness of 13 μm after drying, thereby producing a drum-shaped electrophotographic photoreceptor.

The photoreceptor produced in this way was used in an electrophotographic copying machine "U".
-BIX vz" (manufactured by Konishiroku Photo Industry Co., Ltd.), and when the entire image was copied, a copy with high contrast, faithful to the original, and clear was obtained.

Moreover, this did not change even after repeating 10,000 times.

Comparative Example 2 Except for replacing the exemplified compound A-(2)' with an azo compound (()-2) represented by the following structural formula in Example 5,
A drum-shaped comparative sensory body was prepared in the same manner as in Actual IM Example 5, and the copied image IJP'lk was evaluated in the same manner as in Example 5. As a result, there were many capri Ii! 1 illll! In addition, as the copying was repeated, the contrast of the copied image decreased, and after 2000 repetitions (G-2
i (Example 6) A 0.0-thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC MP-10J (manufactured by Block Chemical Co., Ltd.) was coated on the surface of an aluminum drum with a diameter of 100 mm.
A 5 μm middle layer was provided, and the exemplified compound (A-
(2) 149 was mixed with 1,2-dichloroethane 400-, and a dispersion of dead time dispersed using a ball mill disperser was applied so that the film thickness after drying was 0.5 μm,
A carrier generation layer was formed.

Furthermore, 4-methyl-4'-styryltriphenylamine 3019 and polycarbonate resin [Hanlite L-1250j (manufactured by Yondai Kasei Co., Ltd. 150.9) were added on top.
A carrier transport layer was formed by dissolving 2-dichloroethane in 400 rrtl VC and coating it to a film thickness of 12 μm after drying, thereby producing an electrophotographic photoreceptor on a drum.

The spectral sensitivity of this photoreceptor at 780 nm is 1. o9μ
J/cr1. (Half-reduced light cover).

Next, this photoreceptor is heated so that the laser light intensity on the surface of the photoreceptor is 0.
Semiconductor laser (780 nm l') with 85 mW
A live-action test was conducted using an experimental machine installed in

After the surface of the photoreceptor was charged to t--6KV, it was exposed to laser light and subjected to inversion development at a bias voltage of -350V, and a good image without capri was obtained.

Further, even if this was repeated fl 10,000 times, there was no change.

Example 7 A drum-shaped photoreceptor was obtained in the same manner as in Example (6) Vc using Exemplified Compound A-(1) instead of Exemplified Compound A-(2)ic.

The spectral sensitivity of each photoreceptor at 780 am is 1.
It was 30 μJ/cze (half-exposure violet).

The results of a live-action test using an experimental machine gave a good image with no capri, and there was no change even after 10,000 repeated tests.

[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 1 to 7 in the figures represent the following, respectively. DESCRIPTION OF SYMBOLS 1... Conductive support, 2... No carrier generation, 3... Carrier transport layer, 4... Photosensitive layer, 5... Intermediate layer, 6... Contains carrier@containing substance Layer 7... carrier generating substance. Agent Yoshimi Kuwahara Figure 1 Figure 2 Figure 5 Ru-4-Figure

Claims (1)

[Scope of Claims] 1) A photoreceptor having the general formula [■], which is characterized by having a photosensitive layer containing a disazo compound represented by the following general formula [■] on a conductive support; a substituted alkyl group, or a substituted
It is represented by an unsubstituted aryl group 1, R is a hydrogen atom, an alkyl group, an alkoxy group"1'fc is a halogen atom, and 2 is a substituted or unsubstituted aromatic carbocycle or a substituted or unsubstituted Atom group necessary to constitute an aromatic heterocycle, Y: substituted/unsubstituted carbamoyl group or substituted/unsubstituted sulfamoyl group, R1: pilot atom, substituted/unsubstituted alkyl group, substituted/unsubstituted Amine group, substituted/unsubstituted carbamoyl group, carboxy group and its ester group, or cyano group, A': substituted/unsubstituted aryl group, R2 and R3: substituted/unsubstituted alkyl group, substituted/unsubstituted represents an aralkyl group or a substituted/unsubstituted aryl group.] 2) The photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance is the general formula CI]
The electrophotographic photoreceptor 0 according to item 1, WfBli, which is a disazo compound represented by