JPS60209740A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To provide an electrophotographic sensitive body having high sensitivity and low residual potential, undergoing no change in the characteristics even after repeated use, and showing superior durability by incorporating an azo compound having stability to heat and light and superior carrier generating capacity. CONSTITUTION:An azo compound represented by general formula I (where A is a bivalent residue bonding to azo forming N atoms through C atoms, X is a naphthalene reing, a carbazol ring, a benzofuran ring or a substitution product thereof, and each of R1 and R2 is H, alkyl which may have a substituent, phenyl which may have a substituent, halogen, nitro or furyl) generates charge carrier with very high efficiency when the compound absorbs light. The generated carrier may be transferred with the azo compound as a medium, but it is preferable that the carrier is transferred with a known charge transferring substance as a medium. Charge transferring substances are generally classified into two kinds, electron and hole transferring substances. Both the substances can be used in the photosensitive layer of an electrophotographic sensitive body of this invention.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to a novel electrophotographic photoreceptor having a photosensitive layer containing an azo compound. More specifically, the present invention relates to a highly durable electrophotographic photoreceptor that has high sensitivity and is suitable for repeated use.

- Conventionally, electrophotographic photoreceptors include selenium, zinc oxide,
Those having a photosensitive layer mainly composed of an inorganic photoconductor such as cadmium sulfide were widely known.

However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc., and there are also restrictions in production and handling, especially since cerium and cadmium sulfide are toxic. On the other hand, electrophotographic photoreceptors having a photosensitive layer containing an organic photoconductive compound as a main component are relatively easy to manufacture, inexpensive, and easy to handle, and are generally more expensive than selenium photoreceptors. Poly-N-vinylcarbazole is a well-known organic photoconductive compound that has attracted much attention in recent years due to its many advantages such as excellent thermal stability. and 2.4.7-) Lewis acid such as dinitro-9-fluorenone. Electrophotographic photoreceptors having a photosensitive layer mainly composed of a charge transfer complex formed from a Lewis acid such as dinitro-9-fluorenone are not necessarily satisfactory in terms of sensitivity and durability. .

On the other hand, in laminated or dispersed function-separated photoreceptors, in which the carrier generation function and the carrier transport function are assigned to separate substances, each material has a wide selection range, and the charging characteristics, sensitivity, and durability are It has the advantage that an electrophotographic photoreceptor having arbitrary properties can be produced relatively easily in terms of electrophotographic properties such as properties.

Conventionally, various carrier-generating substances or carrier-transferring substances have been proposed.

For example, an electrophotographic photoreceptor has been put into practical use that has a photosensitive layer that combines a carrier generation layer made of amorphous selenium and a carrier transfer layer mainly composed of poly-N-vinylcarbazole.

However, a carrier generation layer made of amorphous selenium has a drawback of poor durability.

In addition, various proposals have been made to use organic dyes and pigments as carrier-generating substances. Showa 52-4
No. 241, JP-A-54-46558, JP-B-Sho 56-11945, etc. are already known.

However, these azo compounds are not necessarily satisfactory in terms of sensitivity, residual potential, or stability when used repeatedly (and the selection range of carrier transfer substances is also limited, etc.). The reality is that nothing that fully satisfies the wide range of demands of electrophotographic processes has yet to be obtained.

The object of the present invention is to be stable to heat and light.

Another object of the present invention is to provide an electrophotographic photoreceptor containing an azo compound having excellent carrier generation ability.

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

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

As a result of intensive research to achieve the above objectives, the present inventor has
The present invention was completed based on the discovery that an azo compound represented by the following general formula (1) can function as an active ingredient of a photoreceptor.

(In the formula, A is a divalent residue bonded to the N atom forming an azo with the C atom, and X is a naphthalene ring, a carbazole ring, a benzofuran ring, or a substituted product thereof,
R,, R, is hydrogen, an alkyl group that may have a substituent,
Phenyl group which may have a substituent, halogen, nitro,
It is a frill group. ) That is, in the present invention, by using the azo compound represented by the general formula (I) as a photoconductive substance constituting the photosensitive layer of an electrophotographic photoreceptor, the azo compound of the present invention can be used as an excellent carrier. By utilizing only the generation ability and using it as a carrier generation material in a so-called function-separated electrophotographic photoreceptor, in which carrier generation and transfer are performed using separate substances, the physical properties of the film can be surpassed, and the charge retention ability and sensitivity can be improved. , which has excellent electrophotographic properties such as residual potential, has little fatigue deterioration even after repeated use, and exhibits stable properties without changing the above-mentioned properties even when exposed to heat or light. Photographic photoreceptors can be created.

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

Exemplary Compound fl+ \self (2) 〈H\゛' The bisazo compound represented by the above general formula (1) has the general formula H*NA-NHI (in the formula, the person has the same meaning as above).

) is tetrazotized by a conventional method, and then the corresponding coupler is camped in the presence of an alkali, or the tetrazonium salt of the diamine is once separated in the form of a borofluoride salt or zinc chloride double salt, etc. Thereafter, the compound can be easily synthesized by campling with a coupler in a suitable solvent such as N,N-dimethylformamide or dimethylsulfoxide in the presence of an alkali.

Next, a method for synthesizing a representative example of the azo compound used in the present invention will be shown.

Synthesis Example (Exemplary Compound 7) 3.3'-dichlorobenzine dihydrochloride 13.04&(4
0 mm014) was added to a mixture of 20 mm of concentrated hydrochloric acid and 40 mm of water to disperse it, and then added dropwise to a bath solution containing 5.52 # (80 mm mole) of sodium nitrite dissolved in water under cooling. The reaction was allowed to proceed for 1 hour. Next, activated carbon was added and treated to obtain a tetrazonium aqueous solution.

N-(2-thiazolyl)-2- as a coupling component
Hydroxy-11H benzocarbazole-3-carbozamide 10.3g (30mmole) (melting point 350C
(above) Triethanolamine 10.5 as an organic amine
g (70 mmole) of dimethyl sulfoxide 500
- and dimethylformamide 300 - and cooled to 0 to 5C.

Next, the above diazonium salt solution was added dropwise into the coupler solution, and the resulting dark black base material was kept at 0 to 10C and stirred for an additional 3 hours. The precipitate formed was filtered, thoroughly washed with acetone and then water, and finally washed again with acetone to obtain 7.6 g of black red powder after drying. The melting point was 350C or higher. It was insoluble in ordinary water, alcohol, ketones, esters, etc., except for being slightly soluble in dimethylformamide.

Other azo compounds of the present invention can also be obtained according to the above synthesis example.

The electrophotographic photoreceptor of the present invention has a photosensitive layer containing one or more azo compounds represented by the above general formula.

Various forms of the photosensitive layer are well known, and the photosensitive layer of the electrophotographic photoreceptor of the present invention may be in any of them. Usually, the photosensitive layer is of the type exemplified below.

■A photosensitive layer made of an azo compound ■A photosensitive layer in which an azo compound is dispersed in a binder ■A photosensitive layer in which an azo compound is dispersed in a well-known charge transfer substance The azo compound represented by the above general formula generates charge carriers with extremely high efficiency when it absorbs light. Although the generated carriers can be transferred using an azo compound as a medium, it is preferable to transfer the generated carriers using a known charge transfer substance as a medium. From this point, the photosensitive layer of the form ■ and ■ is (
preferred.

Charge transfer substances are generally classified into two types: electron transfer substances and hole transfer substances, and both can be used in the photosensitive layer of the photoreceptor of the present invention, and a mixture of substances having the same function can be used. Also, mixtures of materials having different functions can be used. Examples of substances having electron transfer include electron-withdrawing compounds having electron-withdrawing groups such as nitro groups, cyano groups, and ester groups; examples of these include 2.
4.7-) Nitrated fluorenone such as linitrofluorenone, 2,4.5.7-titranitrofluorenone, or tetracyanoquinodimethane, tetracyanoethylene, 2.4.5.7-tetranitroxanthone, 2 .4
．． 8-) Compounds such as IJ nidrothioxanthone,
Examples include polymerized electron-absorbing compounds.

Furthermore, examples of electron-donating organic photoconductive compounds that can be used as hole transport media include the following.

Hydrazones Pyrazolines><Diarylalkane> -C3H7 -C3H7 -C3H7 fH11 n-03H? CH8 c6H13 Alkylene diamines><Dibenzylanilines>Triphenylamines><Diphenylbenzylamines>Triarylalkanes> Hs 1 Oxadiazoles> 4) N-N (<Oxazoles>, etc.) Other polymer compounds include poly-N-vinylcarbazole, halogenated poly-N-
Vinyl carbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, polyglycidylcarbazole, polyvinylacenaphthylene, ethylcarbazole-formaldehyde resin, etc. can also be used.

The carrier transfer substances are not limited to those described herein, and when used, one type or a mixture of two or more types of carrier transfer substances can be used.

The electrophotographic photoreceptor of the present invention can be manufactured according to a conventional method.

For example, an electrophotographic photoreceptor having a photosensitive layer of type (2) above is prepared by coating a coating solution obtained by dissolving or dispersing the azo pigment of the present invention in a suitable medium on a conductive support and drying it. . It can be manufactured by forming a photosensitive layer with a thickness of m to several μm.

Examples of media for preparing the coating solution include basic solvents that dissolve bisazo compounds such as n-butylamine, ethylene, and diamine; ethers such as tetrahydrofuran 1,4-dioxane; ketones such as methyl ethyl ketone and cyclohexanone; toluene and xylene. Aromatic hydrocarbons such as: N, N-dimethylformamide, acetonitrile, N
- Aprotic polar solvents such as methylpyrrolidone and dimethyl sulfoxide; Alcohols such as methanol, ethanol, and ingropanol; Esters such as ethyl acetate, methyl acetate, and methyl cellosolve acetate; Chlorinated hydrocarbons such as dichloroethane and chloroform; Examples include a medium for dispersing the azo compound.

When using a medium for dispersing the azo pigment, the particle size of the azo pigment is 5 μm or less, preferably 3 μm or less, and optimally 1 μm or less.
It is necessary to make the particles smaller than μm.

Furthermore, as the conductive support on which the photosensitive layer is formed, any of those employed in well-known electrophotographic photoreceptors can be used.

Specifically, examples include metal drum sheets made of aluminum, copper, etc., and laminates and vapor deposits of these metal foils.

Further examples include plastic films, plastic drum paper, etc. which are coated with a conductive substance such as metal powder, carbon black, copper iodide, or polymer electrolyte together with a suitable binder to conductivity treatment.

Also included are plastic sheets and drums that contain conductive substances such as metal powder, carbon black, and carbon fibers and are made conductive.

If a binder is dissolved in the coating liquid used to form the photosensitive layer of the type (2) above, an electrophotographic photoreceptor having the photosensitive layer of the type (2) above can be produced. In this case, the medium of the coating liquid is preferably one that dissolves the binder.

As binders, polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, acrylic esters, methacrylic esters, phenoxy resins, polysulfone,
Examples include various polymers such as arylate resin, polycarbonate, polyester, cellulose ester, cellulose ether, urethane resin, epoxy resin, and acrylic polyol resin.

The amount of binder used is usually 0.1 to 0.1 to the amount of azo pigment.
The range is 5 times the weight.

In addition, in forming this type of photosensitive layer,
Disazo pigment in a binder with a fine particle size, e.g. 3μ
It is preferable that the particles exist in the form of fine particles of 1 μm or less, particularly 1 μm or less. Similarly, by dissolving a charge transfer medium in the coating liquid used to form the photosensitive layer of the type (2) above, an electrophotographic photoreceptor having the photosensitive layer of the type (2) above can be manufactured.

As the charge transfer medium, any of those exemplified above can be used.

In addition to charge transfer media that can themselves be used as binders, such as polyvinylcarbazole and polyglycidylcarbazole, it is preferable to use other binders as binders.

As the binder, any of those exemplified above can be used. In this case, the amount of binder used is usually 5 to 10 times the weight of the azo pigment, and the amount of charge transfer medium used is usually 0.2 to 1.5 times the weight of the binder.
times the weight, preferably in the range of 0.3 to 1.2 times the weight.

In the case of a charge transport medium which itself can be used as a binder, it is usually used in an amount of 5 to 10 times the weight of the azo pigment. In this type of photosensitive layer, it is preferable that the disazo pigment is present in the charge transport medium and the binder in the form of fine particles, similar to the photosensitive layer of type (1) above.

If a coating solution obtained by dissolving a charge transfer medium in a suitable medium is applied onto the photosensitive layer of the types ① to ① above and dried to form a charge transfer layer, the electron Photographic photoreceptors can be manufactured.

In this case, the photosensitive layers of types (1) to (4) above serve as charge generation layers.

The charge transfer layer is not necessarily provided above the charge generation layer, but may be provided between the charge generation layer and the tetraelectric support.

However, the former is preferable in terms of durability.

The charge transfer layer is formed in the same manner as the photosensitive layer described in (2) above.

That is, the coating liquid for forming the photosensitive layer described in (1) above, except that the azo pigment is removed, may be used as the coating liquid. Typically, the charge-generating jilt is 5 to 50 microns thick.

Of course, the photosensitive layer of the electrophotographic photoreceptor of the present invention may contain a known sensitizer.

Suitable sensitizers include Lewis acids that form charge transfer complexes with organic photoconductive substances and dyes. Examples of Lewis acids include chloranil, 2,3-dichloro-
1,4-naphthoquinone, 2-methylanthraquinone, 1
- quinones such as nitroanthraquinone, 1-chloro-5-nitroanthraquinone, 2-chloroanthraquinone, phenanthrenequinone% aldehydes such as 4-nitrobenzaldehyde, 9-benzoylanthracene, indanedione, 3,5-dinitrobenzophenone, 3,
3;5,5'-f) Ketones such as dinitrobenzophenone, acid anhydrides such as phthalic anhydride and 4-chloronaphthalic anhydride, tetracyanoethylene, tele7 tarmalone nitrile, 4-nitrobenzalmalone nitrile, etc. cyano compound, 3-benzalphthalide, 3-(α-cyano-p-nitrobenzal)phthalide, 3-(α-cyano-
Examples include electron-withdrawing compounds such as p-nitrobenzal) phthalides.

Examples of dyes include triphenylmethane dyes such as methyl violet, brilliant green, and crystal violet, thiazine dyes such as methylene blue, quinone dyes such as quinizarin, cyanine dyes, and pyrylium salts, thiapyrylium salts, and benzobyrylium salts.

In addition, inorganic photoconductive fine particles such as selenium and selenium-arsenic alloys, and organic photoconductive pigments such as copper phthalocyanine pigments and perylene pigments may also be contained.

Further, the photosensitive layer of the electrophotographic photoreceptor of the present invention may contain a known plasticizer in order to improve film formability, flexibility, and mechanical strength.

As plasticizers, phthalate esters, phosphate esters,
Examples include aromatic compounds such as epoxy compounds, chlorinated paraffins, chlorinated fatty acid esters, and methylnaphthalene. Moreover, it goes without saying that an adhesive layer, an intermediate layer, and a transparent insulating layer may be included as necessary.

The photoreceptor using the azo pigment of the present invention has high sensitivity and good color sensitivity, and when used repeatedly, there is little change in sensitivity and chargeability, and there is little optical fatigue, and it is extremely durable. .

Furthermore, the photoreceptor of the present invention can be used not only in electrophotographic copying machines but also in lasers, cathode ray tubes (CRT), and light emitting diodes (LEDs).
It can also be widely used in electrophotographic applications, such as photoreceptors in printers that use light as a light source.

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

Example 1 Polyester film laminated with aluminum foil (Alvet 85 manufactured by Daido Kako Co., Ltd., aluminum film thickness 10 μm)
) on a conductive support consisting of vinyl chloride: vinyl acetate:
Maleic anhydride copolymer (Sekisui Chemical Co., Ltd. S-LEC MF)
-10) Form an intermediate layer with a thickness of 0.05μ consisting of,
2I of Exemplified Compound Incisor 1 and 2 g of polyarylate resin (Unitika My-100) were combined into
In addition to 100 d, an azo compound dispersion obtained by dispersing in a paint conditioner for about 1 hour is applied onto the intermediate layer so that the film thickness after drying is 0.5 μm and dried to form a carrier generation layer. and further carrier transfer substance N, N-dibenzylaminobenzaldehyde-1
, 1-diphenylhydrazone 5y dissolved in 12-dichloroethane 5o- along with 7 g of polyarylate resin is coated and dried to form a carrier transfer layer, and dried to form a carrier transfer layer. My body exploded. After storing this photoreceptor in a dark place at a room temperature of 30°C for one week,
This electrophotographic photoreceptor was tested using an electrostatic paper tester [5P-428J (
(newly manufactured by Kawaguchi Electric) and conducted the following characteristic tests.

That is, the photosensitive layer is charged by corona discharge for 5 seconds by applying a voltage of d% -6kv, and the potential Vo at that time is
(-V), then the illuminance at the surface of the photosensitive layer is 30 lu
Exposure amount E÷ required to reduce the surface potential of the photosensitive layer to % by irradiating light from a halogen lamp in a state where x
(lux・sec). Also, the surface potential after exposure with an exposure amount of 301 ux·sec, that is, the residual potential E. (−■
) was repeated 500 times.

Further exposure was carried out for 0.3 seconds at 3001 ux using a tungsten lamp as a light source for residual potential neutralization to completely reduce the residual potential to zero.

The results are shown in Table 1.

Table 1 Examples 2 to 5 Exemplary compounds 7.9.1 as carrier generating substances, respectively
A total of 4 was prepared in the same manner as in Example 1 except that 6.24 was used.
Various types of electrophotographic photoreceptors of the present invention were prepared, and similar characteristic tests were conducted on each of them. The results are shown in Table 2.

Table 2 Example 6 External drum 1110 made of aluminum and having a diameter of 80 mm
On the surface, an intermediate layer with a thickness of 0.04μ made of vinyl chloride: vinyl acetate (87:13) copolymer (VYHH manufactured by UCIC) was formed, and 704 g of the exemplary compound was added to 400 g of 1,2-dichloroethane. A dispersion obtained by dispersing for about 3 hours using a Heint condenser was applied and dried on the intermediate layer so that the film thickness after drying was 0.5 μm to form a carrier generation layer. The carrier transfer substance N,N-diallylaminobenzaldehyde-1-phenyl-1-methylhuman2 indicated by this carrier generation
A solution prepared by dissolving Shin 10# and 12 g of polycarbonate resin (Kijin Panrai L-1250) in 1,2-dichloroethane 100 was dried to a film thickness of 15 μm.
A carrier moving layer was formed by coating and drying to produce a drum-type electrophotographic photoreceptor according to the present invention.
When this electrophotographic photoreceptor was installed in our modified commercially available cartridge-type electrophotographic copying machine and a copied image was formed, a clear visible image with high contrast and faithful to the original was obtained.

The copying process was repeated 1000 times, and until the end, a visible image equivalent to that of the first copy was obtained.

Example 7 The reflection spectrum of the drum-type electrophotographic photoreceptor obtained in Example 6 was measured using a spectrophotometer equipped with an integrating sphere (Shimadzu UV-365).
), and the graph is shown in Figure 1. From this graph, the maximum absorption wavelength in the visible region of this photoreceptor is 66
It turned out to be around 5 nm. Furthermore, 660 nm,
When the spectral sensitivity at 670 nm was measured using a monochrome meter, the energy required to halve the potential was 4.5 nm for both wavelengths. It was found that the photoconductor has a very high OJrei.OJrei., and can be used in practical use even when a light emitting diode (LED) is used as a light source.

Examples 8 to 12 An intermediate layer with a thickness of 0.05μ made of vinyl chloride: vinyl acetate copolymer (Kanepiraku L-CP manufactured by Kaneka Co., Ltd.) was formed on a conductive support made of a polyester film on which aluminum was vapor-deposited, Exemplary compound 7.12.31.42.5
A solution of No. 9 dissolved in n-butylamine, which is an azo compound, was applied onto the intermediate layer to form a carrier generation layer having a thickness of 0.1 μm. Then, 1-
A solution of diethylaminophenyl-3-phenyl-5-styrylpyrazoline 5I and polyester resin (Vylon-200 manufactured by Toyobo Co., Ltd.) dissolved in 1.2-dichloroethane 40-5 was prepared so that the film thickness after drying was 14μ. A carrier transfer layer was formed by coating and drying, thereby producing an electrophotographic photoreceptor of the present invention. The maximum absorption wavelength in the visible to near-infrared range and the energy required to reduce the potential by half at that wavelength were determined according to Example 7 based on the reflection and absorption curves of the photoreceptors having a total length of 5 meters. The results are shown in Table 3. The initial potential VO of all photoreceptors exceeded 500 (-v). Furthermore, all maximum absorption wavelengths are rounded up within the range of 0 to 5 nm.

Table 3 Example 13 Styrene: methyl methacrylate: methacrylic acid copolymer (styrene: methyl methacrylate = 2:1 weight ratio, acid value 185), Exemplary Compound 20 and Tonitro Florenone 1.5:1:
Mixed at a weight ratio of 0.3 and dissolved in dioxane (
Resin component, trinitrofluorenone) dispersion (azo compound)
A single-layer photoreceptor with a film thickness of 6 μm was prepared by applying and drying the stain solution.

The photoreceptor of the present invention thus prepared was subjected to an electrophotographic property test using the electrostatic paper tester described above.

Applied voltage was +6 kV Vo-450 (+v) Er=s (lux·sec).

The photoreceptor was visualized with a developer (toner) and then treated with an alkaline processing solution (e.g. 35A, 10% ammonium carbonate, and 20% polyethylene glycol with an average molecular weight of 19()-210). After the treatment, the toner-free layer was easily removed from the bath, and then washed with water containing sodium silicate, thereby making it possible to easily prepare a printing original plate.

When offset printing was performed using this original plate, it was found that it could withstand printing of about 100,000 sheets.

In addition, in order to obtain a toner visible image (light source: halogen lamp)
The optimal exposure was 13 lux at 501 ux.

In addition, when creating the original printing plate, direct plate making was performed without using any base material.

[Brief explanation of drawings]

FIG. 1 shows the reflection spectrum of the photoreceptor obtained in Example 6. Figure 1 L Female (9L9L) Procedural amendment (voluntary) ■, “1-Indication Sho fn59Q-127 permission +1: IFI No. 38158 2, Name of the invention Electrophotographic photoreceptor 3, Consideration for amendment = I ;f'l゛to n+21 section 4Qf creation 1 (irl
Appointment Location: Tokyo Shimo-dai 111-ku Marunouchi 3-chome 2-114-2 Name (?1;
．． Ceremony (14, Agent address: Marunouchi 2-chome I, 111-ku, Tokyo, 100)
4 No. 2 Mitsubishi Paper Mills Co., Ltd. 6, Number of inventions increased by amendment None 7, Amendment t
=j (1) Page 24, line 15 of the specification. r13.04f (40mmole) J ir 3.3
Corrected to f (10 mmole) J. (2) Same page 24, line 16. Corrected 120mZJ to 12-”. (3) Same page 24, line 17. r5.52F (80mmole) J l:r 1
．． Corrected to 5F (22mmole) J. (4) Same page 25, line 5. rlO,5f(70mmole)Jir5.3f(3
5m mole) Corrected to J. (5) Same as No. 25, lines 5 to 7. "Dissolved in a mixed bath agent of 500 parts of dimethyl sulfoxide and 300 parts of dimethylformamide," was corrected to "Dissolved in 300 parts of dimethylformamide." (6) Same page 45, line 10. "Ethylene, diamine" was corrected to "ethylenediamine". (7) Same page 46, line 11. "Drum sheet" was corrected to "drum, sheet". (8) Same page 46, line 16. Corrected "plastic drum paper" to "plastic, drum, paper". (9) Same page 48, line 13. r5~10μmJ kr 1~10. c+m Corrected to J〇('10) Same page 49, line 18. "Charge generation layer" was corrected to "charge transfer layer j." (11) Same page 50, line 14. "4-chlorna7tal enemy" was corrected to "4-chlorophthalic acid." (12) Negative No. 51, line 4 - Corrected "quinone such as quinizarin" to "quinoline such as quinoline red." It is characterized by having a photosensitive layer containing all of the compounds.
i4 child photographic photoreceptor. (In the formula, A is a 211nI residue bonded to the N atom forming an azo with 0JJA, and X is a naphthalene ring, a carbazole ring, a benzofuran ring or
R1 and 2 are hydrogen, an alkyl group which may have a chiral group, a phenyl group which may contain a substituent, a halogen, a nitro group, a furyl group 't'; ) The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer contains a carrier transfer substance and a carrier generation substance, and the carrier generation substance is an azo compound represented by the general formula (11). (3 ) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (11) is a compound represented by the following structural formula: (wherein m and n are 0 or 1, and R5 is hydrogen, lower alkyl, or halogen, and X% "1" and "2" are synonymous with the first term.) (4) The azo compound represented by the general formula (11) is a compound represented by the following structural formula. An electrophotographic photoreceptor according to claim 1. (wherein X is hydrogen, methoxy, halogen, lower alkyl,
nitro, carboxy) s W-R1 and 几2 have the same meanings as in the first term. ) (5) A single copy A-photoreceptor according to claim 1, wherein the azo compound represented by the general formula (11) is a compound represented by the following structural formula. (In the formula, Y is hydrogen, halogen, Cyan, and %X%TL
+s几2 has the same meaning as the first term. ) (6) The above general formula (
The electrophotographic photoreceptor according to claim 8g1, wherein the azo compound represented by 11 is a compound represented by the following structural formula. (In the formula, Z is 10-1-s-1-NH-1-8e-, and Xs Rls R2 has the same meaning as the first term.) (7)
The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (1) is a compound represented by the following structural formula. (In the formula, FL4 is hydrogen, allyl, propargyl, alkyl which may have a substituent, benzyl which may have a substituent, phenyl which may have a substituent, and s
%R1sR2 has the same meaning as the first term. ) (8) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (11) is a compound represented by the following structural formula. It has the same meaning as paragraph 1.) (9
) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (11) is a compound represented by the following structural formula. Substituent 1r
It is benzyl which may have an alkyl Lm group which may be tA, and Xs 几1 and kL2 have the same meanings as in the first term. ) (10) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (11) is a compound represented by the following structural formula. may be benzyl, alkyl, allyl, propargyl, hydrogen, and X1R1, R
2 is synonymous with the first term. ) (11) Claim 1, wherein the bisazo compound represented by the general formula (1) is a compound represented by the following structural formula:
The electrophotographic photoreceptor described in . 2 (wherein R7 and 8 are hydrogen, halogen, lower alkyl,
In methoxy and nitro, y, x, 几1, and R2 have the same meanings as in the first term. )

Claims (1)

[Scope of Claims] (1) An electrophotographic photoreceptor comprising a photosensitive layer containing an azo compound represented by the following general formula (1) on a conductive support. (In the formula, A is a residue of 2ilIIi bonded to the N atom forming an azo at the C atom, X is a naphthalene ring, a carbazole ring, a benzofuran ring, or a substituted product thereof, is hydrogen, an alkyl group which may have a substituent, a phenyl group which may have a substituent, halogen, nitro, or a furyl group. 2. The electrophotographic photoreceptor according to claim 1, wherein the carrier-generating substance is an azo compound represented by the general formula (I). (3) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (I) is a compound represented by the following structural formula. 1 Akebono・1 (In the formula, mS n is O or 1, Karasu is hydrogen, lower alkyl, halogen, and X , R + , R1 are the first
Synonymous with term. ) (4) vflff claims, wherein the azo compound represented by the general formula (I) is a compound represented by the following structural formula (wherein, X, R, and R2 have the same meanings as in Item 1). ) The electrophotographic photoreceptor according to claim 1, wherein the azo compound represented by the general formula (I) is a compound represented by the following structural formula. benzyl which may have an alkyl substituent which may have a group, and X, R, and R1 have the same meanings as in item 1) H an azo compound represented by the above general formula (1) The electrophotographic photoreceptor according to claim 1, wherein is a compound represented by the following structural formula. 4=pR(,R
, is synonymous with the first term. )aυ A patent claim in which the bisazo compound represented by the general formula (1) is a compound represented by the following structural formula (×・ (wherein, 2+ RA is hydrogen, halogen, lower alkinope methoxy, nitro, X, R ,,R,. is synonymous with the first term.)