JPS60214365A - Photosensitive body - Google Patents

Abstract

PURPOSE:To retain high sensitivity, small residual potential, light and heat stability, and superior durability by forming a photosensitive layer contg. a specified azo compd. CONSTITUTION:An azo compd. represented by the formula is used as a photoconductor for constituting the photosensitive layer of the photosensitive body. The carrier generating layer 2 essentially consisting of the azo compd. represented by the formula and a carrier transfer layer 3 essentially consisting of a carrier transfer material are formed on a conductive substrate 1 to form a laminate type photosensitive layer 4. As the conductive substrate 1, a metal plate including foil, a metal drum, or paper or plastic film made conductive by applying, vapor-depositing, or laminating a conductive material, such as a conductive polymer or indium oxide, or a metallic thin layer of Al, Pd, Au, or the like are enumerated. As the carrier transfer material, electron acceptors, such as trinitrofluorenone, tending to easily transfer electron, as well as polymers having on the side chains. heterocyclic compds., such as poly-N-vinylcarbazole, tending to easily transfer positive holes are enumerated.

Description

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

(Prior Art) Conventionally, as electrophotographic photoreceptors, inorganic photoreceptors having photosensitive layers mainly composed of conductive compounds such as selenium, zinc oxide, cadmium sulfide, and silicon have been widely used. , these 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, and or fingerprints, etc., resulting in crystallization and deterioration of its performance as a photoreceptor.

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 nihapo-17-N-vinylcarbazole and 2.4.7-)linitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these shortcomings, attempts have been made to develop a higher performance optical material by sharing the carrier generation function and the carrier transport function with different materials. Many studies have been conducted on photoreceptors because each material can be selected from a wide range of materials and a photoreceptor having arbitrary performance can be produced relatively easily.

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

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 in the photosensitive layer, Japanese Patent Application Laid-open No. 14-1989-228:34, JP-A-55-
Publication No. 73057, Japanese Unexamined Patent Publication No. 117151/1983,
Japanese Unexamined Patent Publication No. 56-46237 is already known.

However, these azo compounds have low sensitivity, residual potential,
The properties of stability during repeated use are not necessarily satisfactory, and the selection range of carrier transporting substances is also limited, so that they do not fully satisfy the wide demands of electrophotographic processes.

Furthermore, in recent years Ar laser, 1-(e
Gas lasers such as Ne lasers and semiconductor lasers are beginning to be used. These lasers are characterized by being capable of 0N10FF in time series, and are particularly promising as a light source for printers for output from computers and multiplex printers with image processing functions, including intelligent severe. Among these, semiconductor lasers are attracting attention because of their properties such as the fact that they do not require electrical (H/optical signal conversion elements) such as acoustic engineering elements, and can be made smaller and lighter. Because the output power is lower than that of gas lasers, and the oscillation wavelength is long (approximately 78 On In or more), the spectral sensitivity of conventional photoreceptors is too high on the short wavelength side. It cannot be used as a photoreceptor as a light source.

(Objective of the Invention) An object of the present invention is to provide a photoreceptor containing a specific azo compound that is stable against heat and light and has an excellent ability to generate Kygiria.

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

Still another object of the present invention is to provide a photoreceptor containing an azo compound that can effectively act as a carrier generating substance even in combination with a wide variety of carrier transporting substances.

Still another object of the present invention is to provide a photoreceptor having sufficient practical sensitivity even to long wavelength light sources such as semiconductor lasers.

Still other objects of the present invention will become apparent from the description in the specification.

(Structure of the Invention) The present invention is based on the discovery, as a result of intensive research to achieve the above object, that an azo compound represented by the following general formula [1] can act as an active ingredient of a photoreceptor, This completes the present invention.

General formula [I] In the above formula, Q alkyl group (C is preferably 1-5)
, a phenyl group, an alkoxy group, a hydrogen atom, an amide group, an alkylamino group, a phenylamino group, or a hydroquine group which may have a substituent, Q2 is a hydrogen atom, a halogen atom, an alkyl group (C is 1 to 5 Desirable), alkoxy group, cya7 group, phenyl group which may have a substituent, ester group, acyl group, acetylamide group, alkyl sulfone group or vinyl group, Y and Y2 are hydrogen atoms, halogen atoms, cyano represents a group, a hydroxy group, an alkyl group, or an alkoxy group, +1 and 11 are integers of O to 2, provided that m and n are not both 0.

A is a hydrogen atom, a substituted/unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted/unsubstituted 7-ralkyl group, a substituted/unsubstituted phenyl group, R7 is a hydrogen atom, a carbon number 1 to 4 (a (negative/unsubstituted alkyl group, substituted/unsubstituted aromatic carbocyclic group (e.g., substituted/unsubstituted phenyl group, substituted/unsubstituted 7-tyl group,
represents a substituted or unsubstituted anthryl group, etc.), or a substituted or unsubstituted aromatic heterocyclic group (for example, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted nobenzofuryl group, etc.).

Substituted/unsubstituted groups include, for example, carbon atoms of 1
~4 alkyl groups (e.g. methyl group, methyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.),
Replacement/not i+! substituted aralkyl groups (examples include benol group, 7enethyl, etc.), lodene atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted or unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g. methoxy group, ethoxy group,
(impropoxy group, tertiary butoxy group, 2-chloroethoxy group), hydroxy group, substituted/unsubstituted aryloxy group (e.g. p-chloro7e/oxy group, 1-su7toxy group, etc.), acyloxy group ( For example, acetyloxy group, p-
cyanobenzoyloxy group, etc.), carboxy group, its ester group (e.g., ethoxycarbonyl group, l11-bromophenoxycarbonyl group, etc.), carbamoyl group (e.g., ami7carbonyl group, tertiary butylaminocarbonyl group, anilinocarbonyl group) etc.), acyl groups (e.g.
acetyl group, 0-nitrobenzoyl group, etc.), sulfo group,
Sulfamoyl convex (e.g., ami/sul7 amoyl group, tertiary butylaminosulfonyl group, U-)lylaminosulfonyl group, etc.), ami7 group, acylamino7 group (e.g., acetylamino group, benzoylamino group) etc.), sulfonamide groups (e.g. methanesulfonamide groups, p
-toluenesulfonamide group, etc.), cyano group, nitro group, etc., but preferably substituted or unsubstituted furkyl group having 1 to 4 carbon atoms) 16 (for example, methyl group, ethyl group, isopropyl group, n- butyl group, trifluoromethyl group, etc.), halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted or unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g. methoxy group, nidoxy group, tertiary butoxy group, 2-chloroethoxy group, etc.) sia/group, nitro group.

Z is an atomic group necessary to form a substituted/unsubstituted aromatic carbocycle or a substituted/unsubstituted aromatic heterocycle,
Specifically, it represents an atomic group forming a substituted/unsubstituted benzene ring, a substituted/unsubstituted 7talene ring, a substituted/unsubstituted indole ring, a substituted/unsubstituted carbazole ring, etc.

Examples of substituents for the atomic group forming these rings include a series of substituents such as those listed as substituents for R4-Rs, but halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), sulfo group, sulfamoyl group (e.g. aminosulfonyl group, R-)dylaminium/
Sulfonyl.

R1 is a hydrogen atom, a substituted or unsubstituted alkyl substituted or unsubstituted ami7 group, a carboxyl ester group, a substituted or unsubstituted carrenocumyl group, or a sia7 group, preferably a hydrogen atom or a carbon i1-4 group. These include substituted/unsubstituted alkyl groups (eg, methyl lake, ethyl group, isopropyl group, tertiary butyl group, 1/3-fluoromethyl group, etc.), and cyano group.

A' is a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, and examples of these substituents include R. , the ability to enumerate a series of substituents such as those listed as substituents for RS? , halogen atoms (chlorine atom, bromine atom, lido 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.), substituted/unsubstituted alkoxy groups with 1 to 4 J atoms (e.g., methoxy group, ethoxy group, iso7).

Roboxy group, tertiary butoxy group, 2-chloro7e/oxy group, ).

R2 and R represent substituted/unsubstituted alkyl groups, substituted/unsubstituted aralkyl groups, and IY (substituted/unsubstituted aryl groups, preferably substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms) (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl convex, trifluoromethyl group, etc.), substituted
Represents an unsubstituted phenyl group (eg, phenyl group, ;)-methoxyphenyl group, 1fl-chlorophenyl group, etc.).

Among the azo compounds represented by the general formula [1] used in the present invention, particularly preferred compounds have the structure represented by the following general formula [■] in terms of sensitivity and stability against heat and light. It is something.

The present invention represented by the general formula [■1 [wherein A, Y, , Y2, and Ql are the same as the general formula [11], and Q2 is a hydrogen atom, a cyano group, an acyl group, or an ester group 1 [the above general formula II]] Examples of useful azo compounds include those having the following structural formula:
However, as a result, it has the structure of general formula [II] of the present invention.

General formula Lll] Those having the structure of general formula [111] General formula [111 Other ones.

B-(2:34) It-(z3s) +1- (2: Kei) B-(239J Answer the above classification methods for azo compounds □.

Easy VC synthesis. A specific example will be shown below.

↓ Σ B -(11 In other words, 2,7-sinitrofluorenone 1 (Tokyo Chemical, manufactured by our company) is reacted with cya/acetone 2 to form dinitro compound 3
This was reduced with stannous chloride to give Sheamite body 4. (Journal of chemical 5o
ciety, 870 (1954)) This noami body 4
27.5 g (0.1 mol) was added to a mixture of concentrated hydrochloric acid (No. 11) and water (No. 11) and dispersed, and a solution of 13.88 (0.2 mol) sodium nitrite dissolved in water 1e was stirred under water cooling for 5 minutes. The mixture was added dropwise at .degree. C., and after the completion of the addition, the reaction solution was filtered, 50% aqueous ammonium hexafluoride phosphorus ammonium fluoride (8 parts, 11) was added to the filtrate, and the resulting precipitate was collected by filtration, washed with water, and thoroughly dried. 4 of the obtained salt
6 no N, N-7 mef-/l rumchi 7 mil' (DMF)
1.51 times of the solution was dissolved to obtain a tetrazonium salt solution to be used in the next reaction.

Next, 2-hydroxy-3-(4-71xy-2-methylphenylcarbamoyl)-benzo[,]-carbazole (naphthol AS-3R, manufactured by Hoechst) 79.3
g (0.2 mol), triethanolamine 608, 4
1 in N,N-methylformamide, and the tetrazonium salt solution prepared above was added dropwise while cooling with water, followed by a further 2 hours of a! I made a reaction. The resulting crystals were collected by filtration and heated to 51N.

2 times with N-methylformamide and 2 times with 51 acetone.
After washing twice and drying, the desired bisazo compound B-(
1) 68.7g (f33%) was obtained. Melting point 300° or higher, vn/z 10891 in FD-MS spectrum
The elemental analysis shows that C=7.
3.72%, N=11.47%, ■(=4.37%(
The calculated values are C=73.81%, N=11.56%, H=
4.35%), it is understood that the target substance was synthesized.

The azo compound of the present invention has excellent photoconductivity, and when a photoreceptor is manufactured using the azo compound, a photosensitive layer in which the azo compound of the present invention is dispersed in a binder is provided on a conductive support. However, among the photoconductivity of the azo compound of the present invention, it can be used as a carrier-generating substance by taking advantage of its particularly excellent carrier-generating ability, and can be effectively produced in combination with this. Particularly excellent results can be obtained when used together with a transport substance to form a so-called functionally separated photosensitive layer. The functionally separated photoreceptor may be of a separate type, but it is more preferably a laminated type photoreceptor in which a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transporting substance are laminated.

Further, the azo compound used in the present invention has the general formula [11
The azo compounds represented by can be used alone or in combination of two or more, and can also be used in combination with other azo compounds. However, the photoreceptor of the present invention can take any of these forms.

Usually, the configuration is as shown in FIGS. 1 to 6. Figures 1 and 3
In the figure, a photosensitive layer 4 consisting of an MtJrI structure consisting 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 is provided on a conductive support l. As shown in FIGS. 2 and 4, this photosensitive WJ 4 may be provided via an intermediate 15 provided on a conductive support. In this way, when the photosensitive layer 4 has a two-layer structure, a photosensitive member having the most immersed electron q true characteristic can be obtained. In addition, in the present invention, FIG. 5 and f56
As shown in the figure, a photosensitive layer 4 comprising the carrier-generating substance 7 dispersed in a layer 6 mainly composed of a carrier-transporting substance.
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 as a carrier-generating substance, the carrier-transporting substance to be used in combination with the azo compound is preferably an electron-accepting substance that easily transports electrons, such as 1-linitrofluorenone or tetranitrofluorenene. vol) Polymers having a heterocyclic compound in the side chain as represented by -N-vinylcarbazole, triazole derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, polyarylalkane derivatives,
7! Nylennoamine derivatives, hydrazone derivatives, ami7
Examples include electron-accepting substances that easily transport holes, such as substituent lucon derivatives, triarylamine derivatives, carbazole derivatives, stilbene derivatives, and 7-functional/thiazine derivatives, but the carrier transporting substances used in the present invention are limited to these. It is not something that will be done.

The carrier generation layer 2 constituting the two-layered photosensitive layer 4 may be applied directly to the conductive support 1 or the carrier transport layer 3, or if necessary, provided with an intermediate layer such as an adhesive layer or a single barrier layer, for example. It can be formed by the following method.

M-1) Dissolve the azo compound in a suitable solvent and 1. A method of applying a mixed solution or a solution mixed and dissolved with a binder added if necessary.

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 as necessary to mix and disperse the resulting dispersion.

Examples of the solvent or dispersion medium used for forming the carrier generation layer include 11-butylamine, diethylamine, ethyleneamine, inpropaturamine, triethanolamine, triethylenediamine, N,N-trimethylformamide, acetone, and methylethylamine. Examples include reketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, nooxane, methanol, ethanol, inpropyl, 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, but a film-forming polymer that is hydrophobic, has a high dielectric constant, and is electrically insulating is used. is preferable. 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-6) Polyvinylidene chloride P-7) Polystyrene P-8) Polyvinyl acetate P-9 ) Styrene-butadiene copolymer P-10)
Vinylidene chloride-acrylonitrile copolymer P-11) Vinyl chloride-vinyl acetate copolymer P-12
) Vinyl chloride-vinyl acetate-maleic anhydride copolymer P-13) Silicone U fat P-14) Silicone-alkyd f% fat P-15)
72/-rubomaldehyde 41 (fat p-ie)
Styrene Fluid Jiffel P-17) Poly-N-vinylcarbazole P-18) Polyvinyl butyral P-19) Polyvinyl 7olmar These binders can be used alone or in a mixture of two or more.

The thickness of the carrier generation layer 2 formed in this way is
It is preferably 0.01 μm to 20 μm, more preferably 0.05 μm to 5 μW. 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 support used in the photoreceptor of the present invention includes a metal plate including an alloy, a metal drum, a conductive polymer,
Al including conductive compounds and alloys such as indium oxide;
Paper that has been coated, vapor-deposited or laminated with metal WJ)vi such as aluminum, palladium, and gold to achieve conductivity and ratio;
Examples include plastic film. As an intermediate layer such as an adhesive layer or a barrier layer, in addition to the high molecular weight polymer used as the binder, polyvinyl alcohol,
Organic polymer substances such as polymer cellulose and carboxymethyl cellulose, or aluminum oxide are used.

The photoreceptor of the present invention has the above-mentioned structure, and as is clear from the examples described later, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and especially when it is revived and used. It has low fatigue deterioration and excellent 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 B-(109) 2 g and polycarbonate resin "Panrai" L-1250J (manufactured by Yondai Kasei Co., Ltd.) 2
B,! :41. In addition to 110 mQ of 2-nochloroethane,
It was released in a ball mill for 12 hours. This dispersion was applied onto a polyester film on which aluminum had been vapor-deposited so that the dry film thickness was 1 μm to form a carrier generation layer, and then a carrier transport layer was formed on top of this to form a carrier transport layer having the following structural formula K.
-(1) 6 g of polycarbonate (4j of fat "Panlite L-1250Jlog" and 1,2-dichloroethane
The film thickness after drying the solution dissolved in 1, O, n11 is 15
A carrier transport layer was formed by coating the photoreceptor so as to have a particle diameter of μm 0, thereby producing a photoreceptor of the present invention.

K-(1) The VJ-treated photoreceptor was tested as described above using an electrostatic paper tester manufactured by Denki Seisakusho, SP-428,
The characteristics of the board were evaluated. After charging for 5 seconds with a charging voltage of -6K V, leave it in the dark for 5 seconds, then irradiate it with a halogen lamp so that the illumination intensity on the photoreceptor surface is 351 ux to destroy the surface potential in half. Required exposure amount (
Half-reduced exposure amount) E% was reduced. In addition, the surface potential (residual potential) VR after exposure with an exposure amount of 301ux''See was measured.

Furthermore, the same 4 m measurement was repeated 100 times. The results are shown in Table 1.

Table 1 Comparative Example 1 The following bisazo compound G-(1) was used as a carrier generating substance.
A comparative photoreceptor was prepared in the same manner as in Example 1, except that .

G-(1) When this comparative photoreceptor was measured in the same manner as in Example 1, the results shown in Table 2 were obtained.

As is clear from the results in the fIS2 table, the photoreceptor of the present invention has
Compared to the comparative photoreceptor, the sensitivity, residual potential, and repetition stability were extremely improved.

Example 2-4 Exemplary compound B-(231) as a carrier generating substance,
Using B-(130) and 13-(5), the following compounds K-(2) and 13-(5) were used as carrier transport substances, respectively.
A photoreceptor of the present invention was prepared using the following compound K-(3) and the following compound K-(4) in the same manner as in Example 1, and the same measurements were performed.The results shown in the ft53 table were obtained. Obtained.

K - (2) and K - (6) were dissolved in 70 mQ of 1,2-chloromethane, and this solution was applied to a dry film thickness of 2μ+n to form a carrier transport layer. A photoreceptor was created.

The same measurements as in Example 1 were performed on this photoreceptor, and the results shown in Table 4 were obtained.

Comparative Example 2 A comparative photoreceptor was prepared in the same manner as in Example 6 except that exemplified compound B-(123) was replaced with bisazo compound G-(2) represented by the following structural formula.

The same measurements as in Example 1 were carried out on this photoreceptor.
(2) Table 4 Example 7 A carrier generation layer was formed in the same manner as in Example 5 except that Exemplified Compound B-(207) was replaced with Exemplified Compound B-(196). On top of this, add the following compound =-(7)6
g and polycarbonate "Panlite L 1250J (manufactured by Yondai Kasei Co., Ltd.) 10g and 1.2-nochloroethane 70TI
A carrier transport layer was formed by applying a solution dissolved in IQ so that the film thickness after drying was 10 μm, thereby producing a photoreceptor of the present invention.

K - (7) Regarding this photoreceptor, measurements were performed in the same manner as in Example 1, and E% = 1. (i 1ux-see and ■, =
It was Ov.

Example 8 Vinyl chloride-vinyl acetate-maleic anhydride) (polymer [
An intermediate layer with a thickness of 0.05 μm made of Eslenc M
0 tnQ and dispersed in a ball mill for 24 hours, the dispersion was coated so that the film thickness after drying was 0.6 μto to form a carrier generation layer.

Furthermore, on top of this, 30 g of the following compound K-(8) and polycarbonate resin "Niepilon S-10004 (manufactured by Nisubishi Gas Chemical Co., Ltd.) 50" and 112E'chloroethane 40
A drum-shaped electrophotographic photoreceptor was prepared by dissolving K - (8) in 01ηΩ and applying the solution to a film thickness of 13 μm after drying to form a carrier transport layer.

The photoreceptor produced in this way is used as an electrophotographic copying plate.
When I attached it to the U Bix 1600 M RJ (Roku Konishi Photos) (manufactured by Nikshasha) and copied the image, I obtained a clear duplicate image with high contrast and faithful to the original. Moreover, this did not change even after repeating 10,000 times.6 In Comparative Example 3 Example 8, Exemplified Compound B-(200) was replaced with a bisazo compound (G-(3)) represented by the following structural formula. Other than that, a comparative photoreceptor in the form of a C drum was prepared in the same manner as in Example 8, and when the copied images were evaluated in the same manner as in Example 8, only images with a lot of fog were observed. or,
As copying was repeated, the contrast of the copied image decreased, and after 2,000 repetitions, it was almost impossible to obtain a copied 1f image.

G-(3) Roofing Example 9 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer “S-LEC MF-10J
(manufactured by Block Chemical Co., Ltd.) with a thickness of 0.05 μm, and on top of that, exemplified compound B-(72)58 and polycarbonate resin [Panlite L-1250J (manufactured by Ryotaikasei Co., Ltd.) 3. 3g and dichloroethane 100TIIQ
In addition, a photoreceptor was prepared by applying a dispersion that had been dispersed for 24 hours using a ball mill so that the coating had a coating thickness of 0μI11 on each side when dried.

The photoreceptor obtained as above was charged with a voltage of -1-6K.
T knee % and ■ were measured in the same manner as in Example 1 except that v was replaced. The first result is 8%” 1.8 lux・s
ec and ■R=+5v.

Example 10 The following compound -(9)6 and polyester resin "Vylon 200 J (manufactured by Toyobo Co., Ltd.) 10 were added as a carrier transport layer on a polyester film on which aluminum was vapor-deposited.
8 and dissolved in 1.2->chloroecune 70mQ, K
-(9) This solution was applied so that the film thickness after drying was 10/7+n.

Next, 1 g of exemplified compound B-(141) and B--(142)Ig were added to this in 11 g of 1,2-dichloroethane.
0. Q and dispersed in a ball mill for 24 hours, and the dispersion was applied to a dry film thickness of 0.5 μm to form a carrier generation layer. ! They formed nine bodies.

The thus obtained photoreceptor was evaluated in the same manner as in Example 9, and it was found that E% = 2.0'1ux-see and VB'' +7v.

Example 11 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer [Stric MF-10
An intermediate layer with a thickness of 0.05 μm made of J (manufactured by Block Chemical Co., Ltd.) was provided, and on top of that, 4 g of exemplified compound I3- (181), 8 g of the following compound -(10), and polycarbonate K-
(10) Resin “Panrai” L-1250J (manufactured by Kijin Kasei Co., Ltd.)
3Fi in 100J of dichloroethane and dispersed with a sand grinder for 24 hours. Dry the dispersion with 1N! A photoreceptor was prepared by coating the film to a film thickness of 10 μm.

E% and VR of the photoreceptor obtained as described above were measured in the same manner as in Example 1 except that the charging voltage was changed to +6 Kv. The first result is E%”1.5 lux・see and V
R=Ov.

Example 12 A 2% ethylenediamine solution of the exemplified compound Compound B-(95) was applied onto a polyester film laminated with aluminum so that the dry film thickness was 0.5 μm0 to form a carrier generation layer.

Furthermore, the following compound -(
11), the following compound K-(12) or the following compound K-(13) was separately added for about 10 hours each to Polycar K-(11) K-(12) K-(13) Bonate resin (Kijin Kasei Co., Ltd.) Manufactured by Panlite L-125
A solution prepared by dissolving 14 g of 1,2-dichloroethane in 140 ml of 1,2-dichloroethane was coated and dried to give a film thickness of 12 μm after drying, thereby obtaining photoreceptors containing three different carrier transport substances.

The characteristics of these three types of photoreceptors were evaluated as follows using SP-428 type electrostatic paper tester manufactured by Kawaguchi Electric Seisakusho (Hayashi) and Iso. Charged for 5 seconds at a charging voltage of -6Kv,
After leaving this in the dark for 5 seconds, irradiate it with 10-density light so that the material surface illuminance is 35 lux, and calculate the exposure amount required to halve the surface potential (half-reduced exposure amount, E%). It was measured. In addition, the surface potential (residual potential) VR after exposure with an exposure amount of 30 lux SeC was measured. Results As shown in Table 6, the combination with any carrier transport substance was good.

Table 5 Comparative Example 4 Exemplary compound B-(95) was converted into the following bisazo compound (G
(N.

Comparative photoreceptors were prepared in the same manner as in Example 12, except that (4)) was used, and the characteristics were evaluated. As shown in Table 6, results varied depending on the carrier transport material.

Table 6 Example 13 Exemplary compound B (195)2B and 100 ynQ of 1,2-dichloroethane were well dispersed and mixed on the conductive support provided with the intermediate layer used in Example 5, and after drying is 0
．． A carrier generation layer was created by coating to a thickness of 3 μm.

Then, as a carrier transport substance, the following compound -(14>68 and polycarbonate [Pamphui] L
-1250J (manufactured by Ondai Kasei Co., Ltd.) and 1.2-NK-(14) were dissolved in 90g of chloroethane. After drying, the membrane 17 was 1.
Coat it so that it has a thickness of 0 μm to form an A Yaria transport layer,
A photoreceptor of the present invention was prepared. Regarding this photoreceptor, 25
The electron-'lj true characteristics at J5 at room temperature of 60° C. and 60° C. were measured in the same manner as in Example 7.

The results are shown in Table 7.

As is clear from the results shown in Table 7, the electrophotographic photoreceptor of the present invention has good sensitivity and residual potential characteristics even at high temperatures;
It can be seen that it is stable against heat.

Example 14 Exemplary compound B-(18[3) was deposited on the conductive support provided with the intermediate layer used in Example 5. and 110 mQ of 1,2-dichloroethane were well dispersed and mixed until the film thickness after drying was 0.
．． A carrier generation layer was prepared by coating to a thickness of 3 μmo.

In order to test the durability of this carrier generation layer against UV light, an ultra-high pressure mercury lamp (manufactured by Tokyo Niura Denki Co., Ltd.) was placed at a position 30 mm apart, and 1500 cd/i UV light was irradiated for 10 minutes.

Next, as a carrier transport substance, the following compound -(15)7Fi and 10 g of polycarbonate [Panlite L-12501 (manufactured by Ondai Kasei Co., Ltd.)] were added to the carrier generation layer that had been irradiated with UV light, and 1.2- A carrier transport layer was formed by coating a solution dissolved in 90 g of dichloroethane so that the film thickness after drying would be 12 μIn, thereby producing a photoreceptor of the present invention.

The same measurements as in Example 5 were performed on this photoreceptor.

The results are shown in the ttSB table.

Example 15 A photoreceptor of the present invention was prepared in the same manner as in Example 14, except that UV light was not irradiated after the carrier generation layer was formed.
The same measurements were carried out. The results are shown in Table 8.

No. 8'& As is clear from the above results, the electrophotographic photoreceptor of the present invention has excellent sensitivity and residual potential characteristics to UV light irradiation,
It can be seen that the amount of fluctuation in the acceptance potential is small, and it is reasonably stable.

Comparative Example 5 Compound 13- (18B) was converted into the following bisazo compound (G
A photoreceptor was prepared in the same manner as in Examples 14 and 15 except that G -(5)) was changed, and the same measurements as in Example 5 and 47) were performed. The results are shown in Table 9.

As is clear from the results shown in Table 9, the photoreceptor prepared using the above compound was able to absorb UV light j! ! tn(niJ), the sensitivity/residual potential characteristics deteriorate, and the amount of fluctuation in the accepted potential is large.

Example 16 In Example 5, exemplary compound B-(123) was converted to B-(
A drum-shaped photoreceptor was fabricated using the same camphor except for 1). The spectral sensitivity of this photoreceptor at 790 nm is 920
vol↑-crl-μW-'-5ec-' (light extinction rate). The semiconductor laser ('7
A live-action test was conducted using an experimental machine that was a MKf version of the 90 old n.

When the surface of the photoreceptor was charged to -6 KV, exposed to laser light, and reverse developed at a bias voltage of -250 V, a good image without fog was obtained.

Comparative Example 6 In Example 16, the following Comparative Example Bisazo Compound G-(6) was used in place of Exemplified Compound B-(1).
(6) The spectral sensitivity of this photoreceptor at 790 old Ro is 70 V.
oljod・μW−1・5ec−′ (photoattenuation rate). Using this comparative photoreceptor, an actual photographic test using a semiconductor laser was conducted in the same manner as in Example 14, but there was a lot of fog and good images could not be obtained.

As is clear from the results of the above Examples and Comparative Examples, the photoreceptor of the present invention is superior to the comparative photoreceptor in terms of properties such as stability, sensitivity, durability, and compatibility with a wide range of carrier transport substances. It is very good.

Example 16-29 A 1″ ram was prepared in the same manner as in Example 5, except that the exemplary compound B-(123) (charge-generating substance) and the compound K-(5) (charge-transporting substance) were changed as shown in Table IO. The spectral sensitivity of this photoconductor at 790II+□ is as shown in Table 10, and the photoconductor (Example 1B-
In a live-action test similar to Example 16 using 29),
Good images with no fog were obtained in all cases.

ni-(1・ ni-(17) -f181 ni-(11 K-4 C.HII K. Monk Ja K Seven K - (c) K-(2■ HIICζゝC,H.

K-(2)) It is extremely excellent in terms of characteristics VC such as a K-bad combination.

(Effects of the Invention) According to the present invention, an azo compound represented by the above general formula CI is used as a photoconductive material constituting the photosensitive layer of a photoreceptor. It also has excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and exhibits little fatigue deterioration even after repeated use. A photoreceptor with excellent sensitivity can be created.

[Brief explanation of drawings]

1 to 6 are sectional views respectively showing examples of the mechanical configuration of the photoreceptor according to the present invention, and 1 to 7 in the figures represent the following, respectively.・. 2...Carrier generation layer, 3...Carrier transport layer, 4...Photosensitive layer, 5...Intermediate layer, 6...Carrier layer containing a transport substance, 7...
...Carrier-generating substance. Agent Patent Attorney No 1) Parents-in-law are also 1, 3, and 3

Claims (1)

[Scope of Claims] (1) A photoreceptor comprising a photosensitive layer containing an azo compound represented by the following general formula [11] on a conductive support. General formula [I] 1 [wherein, Ql is an alkyl group (C is preferably 1 to 5),
A phenyl group, an alkoxy group, a hydrogen atom, an amine 7 group, an alkylamino group, a phenyl amine 7 group, or a hydroxyl group, which may have a substituent, Q2 is a hydrogen atom, a halogen atom, an alkyl group (C is 1-
5), an alkoxy group, a sia7 group, a phenyl group which may have a substituent, an ester group, an acyl store, an acetylamide group, an alkylsulfone group or a vinyl group, Yl and Y2 are hydrogen atoms, halogen atoms, It represents a cyano group, a hydroxy group, an alkyl group, or an alkoxy group, and Λ and 11 each represent an integer from 0 to 2. However, m and 11 are never both 0. A is a substituent formula, where Z is a group of atoms necessary to constitute an unsubstituted aromatic carbocyclic ring, or a substituted or unsubstituted aromatic polycyclic ring, and Q3 is a substituted or unsubstituted aromatic ring. carlenochumoyl group, or substituted or unsubstituted sulfamoyl group, R1 is a hydrogen atom,
Substituted or unsubstituted alkyl group, substituted or unsubstituted amide group 1. Substituted or unsubstituted amino group, substituted or unsubstituted carbamoyl group, carboxyl group and its ester group or cyano group, A' is substituted or unsubstituted aryl group, R2 and R3
represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. 1(2) The photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance has the general formula [
Claim i@1 which is an azo compound represented by I]
Photoreceptor described in section. (3) The photosensitive layer according to claim 1 or 12, wherein the +1ij ad photosensitive layer is constituted by a laminate of a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier generation substance. body.