JPS587147A - Electrophotographic receptor - Google Patents

Abstract

PURPOSE:To provide high sensitivity and high endurance to a receptor and to enhance the heat resistance (Se crystallization) and the moisture resistance by adding anazo pigment having an azo group bonded to a specified coupler residue to the molecule. CONSTITUTION:To the molecule of the photosensitive layer of an electrophotographic receptor is added an azo pigment having an azo group bonded to a coupler residue expressed by formulaI(where R is optionally substituted alkyl or aryl, and R1 is optionally substituted aryl). The especially preferred azo pigment used in this invention is a bisazo or trisazo pigment expressed by formula II.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor using two specific azo pigments.

Conventional photoreceptors containing organic pigments on the conductive layer and I7 are (1)! (11) Japanese Unexamined Patent Application, First Publication No. 1973-1667 (electronic page plate), in which a layer of pigment dispersed in an insulating binder is formed on a conductive layer as disclosed in 1667 (electronic page plate). 30328 (electrophotographic imaging method)) and JP-A-47-18545 (electrophotographic imaging method), or the material and the insulating binder (the binder itself may be a charge transport material). (iii) a conductive layer as disclosed in the Japanese Patent Application Publication No. 49-105537 (by Amai Yoshinban); Layer, frost containing turret;
A charge-generating layer and a charge-transporting layer, GV) A charge-transfer complex as disclosed in JP-A-49-91648 (photoconductive phase), in which a shoulder-transferring pigment is added ( Vn There are others.

Pigments used in such photoreceptors include phthalocyanine pigments, polyquinone pigments, and attenuated pigments (rarely).

The reason is that the organic photoconductive pigment is inorganic Se.

This is because it is inferior to CCTs and ZnO in terms of sensitivity and invagination.

On the other hand, there are also problems with inorganic photoreceptors. If it exceeds 8e, crystallization will be noticeable, and there will be disadvantages such as a decrease in the quality of the 9th grade and the appearance of white rice in the image.8e
Although it is said that the lifespan of the photoreceptor is approximately 30,000 to 50,000 copies, since environmental conditions vary widely depending on the region and location where the copying machine is installed, there are many photoreceptors that cannot complete the lifespan mentioned above. This is the current situation.

In the case of a CJS photoconductor coated with a P3 edge layer, the lifetime dSe;
+, same level as the sensitive body, but with CdS
1. The current situation is that it is extremely difficult to overcome poor humidity, and auxiliary stages such as heaters are required to prevent dust from being absorbed into the photoreceptor.

In the case of ZnO photoreceptors, they are sensitized with dyes such as rose bengal, so there are problems with current deterioration due to corona fluorescence and photofading of the dye, and currently the lifespan of the photoreceptor is limited to 1,000 copies. When expressed as , the unsensitized Se-based photoreceptor is around 151 ux * sec, the sensitized one is about 4 to 8 Iux @ fl, and the CdS thread photoreceptor and sensitized Se are about the same level. The sensitivity of ZnO thread is about 7~12Iux11.

As for the sensitivity of the photoreceptor for emergency purposes, it is desirable that the El/2 value be 20 htx-(8) or less for a PPC copying machine, and more preferably 15 lux-(8) or less for a PPC copying machine with a fast copying speed. However, depending on the application, it may be possible to use it even if the sensitivity is less than the above-mentioned sensitivity.

The misfires have overcome the drawbacks of conventional inorganic photoreceptors,
In addition, as a result of intensive research to improve the drawbacks of organic electrophotographic photoreceptors that have been proposed so far, it has been found that at least one azo group bonded to the coupler residue represented by the above general formula is added to the molecule with a brightness of 1 or 2 mV. The photoreceptor containing three azo pigments has high sensitivity and high durability that can be put to practical use, and it also has heat resistance (Se
The inventors have discovered that this method provides an excellent electrophotographic photoreceptor that solves problems such as crystallization), surface = 1 wettability, and photobleaching, and has arrived at the present invention.

In the general formula, R1 represents an aryl group (eg, phenyl group, α-naphthyl group, β-naphthyl group, etc.).

As a substituent or atom for R1, 0, an alkyl group (e.g., methyl group, ethyl group, propyl group, 1so-
propyl group, butyl group, t-butyl:&, etc.), alkoxy group (e.g., metquine group, ethoxy group, propoxy group, butoxy group, etc.), dialkylamino group (e.g.
dimethylamino group, diethylamine group, diarylamino group, digtylamino group, dibenzylamino group, etc.),
Examples include a diarylamino group (diphenylamino group, ditolylamino group, diarylamino group, etc.), a halogen atom (for example, a chlorine atom, a bromine atom, an iodine atom, etc.), a nitrogen atom, or a cyano group. R is an optionally substituted alkyl group (e.g., methyl group, ethyl group, propyl group, 1SO-propyl group, butyl group, L-butyl group,
Benzyl group, phenethyl group, chlorobenzyl group, dichlorobenzyl group, methylbenzyl group, ethylbenzyl group,
Methoxyhensyl group, 2-methoxyethyl group, 3-methoxyno group, 2-chloroethyl group, (:, 3-talolobrobi residue, 2-human "" xy L thi residue, etc.) or terio-residue ( Example (par r1 phenylno 11.-
, tolyl water, xylyl group, hyphenyl group, mortarophenyl residue, dichlorophenyl At-, toIJ chlorophenyl group, nitrophenyl hanawa, Soj] "noenyl group, methoxyphenyl group, 1 dimethoxyphenyl group, dichlorophenyl group, 10 methoxyphenyl z+1, α-naphthyl group, β-zaftel residue, etc.).

Among the azo compounds 1 included in the present invention, the most important ones are bisazo pigments or trisazo pigments represented by the following formula 1).

General formula (1) In the formula, p ba 2 sweet or 3 is 'L L, R1 is made Ril!
Synonymous with Mi Nishi Maenishi n7) R, + &-, I', 16':
+ Indicates a good aryl group. R,Lj'
iM1′: an alkyl group 4L<6. Showing 14 units. A Iti', (a, l hydration with at least one benzene + fJ 5-) A: ,
(+)) has at least two benzene rings and at least one heterocycle with at least two benzene rings, Indicates a hydrocarbon group. It may be condensed with one or more benzene rings in (a) $ and (bH'?') as described above = it t++: to form a joint abbreviation <, -+ (c) f'r benzene h Q1 other one or more benzene a < +
k: condenses with f heteromonkey to form condensation t + i,
7 is fine. Portion 1■, 1['' (a) hydrocarbon group, (b
) and the hydrocarbon group in (c) are '
1β1 A suitable element f1 For example, an oxygen atom, a chlorine atom (salt; , ethyl group,
propyl)7. , iso-propyl group, butyl group, t-butyl group, etc.), alkoxy thickness (methoxy group,
ethoxy group, propoxy group, butoxy group, etc.), dialkylamino group (menalamino group, diethylamino group,
dipropyl-fmi, ) (5, /butylamino group, dibenzylamine group, etc.), diglylamino group (dialkylamino group, dialkylamino group, dibenzylamine group, etc.), phunrylamino group ((dialkylamino group, dialkylamino group, dibenzylamine group, etc.) Ryo Minono, (
, propionylamino structure, butyrylamino group, pennoyl amino group 9, trimeylamino left 4: 2), nido rI group 4 (fJ hydrogia group, etc.) by VC (4-converted t1-1- and +, :1- j-kiru.

To explain in detail, Saku 1 rt ``i (aJ
+ J46 in (b) and (C): ul is 1512
It is as follows.

Examples of (a) include (1) 乃-it, R5, etc.13 In the formula, R2 is hydrogen atom -i'? :J Cyano, Tsubaki Keishi.

R3 represents a hydrogen atom or an alkoxy group (methoxy group, ethoxy group, propochine group, gutgisif, mochi nato). +14 and R5, hydrogen atom, halogen atom (chlorine atom, bromine atom, and 21, elementary atom), alkyl group (methyl group, ethyl group, propyl group, 1so-propyl group, butyl group, t-butyl group, etc.) , an alkoxy group (methoxy group, ethoxy group, propoxy group, butoxy group, etc.) 1st order indicates a 21-mouth group. Further, R4 and R5 may be the same group at a position symmetrical to '13L, or may be a base group except when both are hydrogen atoms.

As an example of (b), etc. can be mentioned.

An example of (c) is (1,1 2Hs (4) (6) N-N N-N Wo RI2RI3
RI4(8) The atom became t.

(9) (10) etc. can be praised.

R and R7 each represent a hydrogen atom, lower alkyl (e.g.
methyl group, ethyl group, propyl group, iso-propyl group, butyl group, t-butyl group, etc.) or halogen atom (
For example, chlorine atom, bromine atom, iodine atom, etc.).

2 represents an oxygen atom, a sulfur atom, or N-Rts. R16 is a hydrogen atom or a lower alkyl group (for example,
methyl group, ethyl group, propyl group, iso-7'robyl group, butyl group, t-butyl group, etc.). R8 is a hydrogen atom, a halogen atom (for example, a chlorine atom, a bromine atom,
iodine atom, etc.) or lower alkyl groups (e.g., methyl group, ethyl group, fluorobi residue, iso-propyl group, butyl group, L-butyl group, etc.), and islands represent hydrogen atoms, halogen atoms (e.g., chlorine atom). , bromine atom, iodine atom, etc.), lower alkyl groups (e.g. methyl group, ethyl group, propyl group, iso-solopyl group, butyl group, t-butyl group, etc.), alkoxy groups (e.g. methoxy group, ethoxy group, propoxy group) group, butoxy group, etc.), hydroxy group, nitro group, dialkylamino group (e.g., dimethylamino group, diethylamino group, diglobylamino group, etc.)
Or all acylamino groups (eg, acenalylamino group, propionylamino group, butyrylamino group, benzoylamino group, trioylamino group) are shown. Further, n is 0 or 1, and ml is an integer of 1 to 4.

R + or r, I, ffL bond, each indicates a C- group or -CH=CH- group which may be substituted. odor *atom, iodine atom, etc.), alkyl notch (
ψ1j For example, methyl group, ethyl group, furoyl group t 1
(80-furoyl group, butyl group, butyl group, etc.), alkoxy group (for example, methoxy group, etoxy group, zoloboxy group, butoxy group), cyan group, etc.

Rh and R12 & Ni1, hydrogen atom, halogen atom (chlorine atom, bromine atom, iodine atom, etc.) or lower alkyl group (methyl group, ethyl group, propyl group, 1so-propyl group, butyl group, t-butyl group, etc.) ) is shown.

IL+3 and RI4 are a hydrogen atom, a halogen atom (Bu* atom, Kengi atom, iodine atom, etc.), a monovalent alkyl group (methyl group, ethyl group, propyl group, t8o-propyl culm, butyl group, t-butyl alkoxy groups (methoxy group, nidoxime 10 poxy group, butoxy group, etc.)
, nido zero group size or anruamino group (acetylamino group, propionylamino group, butyrylamino group, benzoylamino group, trioylamino group, etc.).

The azo pigment represented by the general formula (1) is a starting compound of 6 /, :) general formula A + Ni-12) n (in the formula n
and A have the same meanings as before) is tetrazotized or hexazated by a conventional method, and then the coupler -C 1 shown in the following &l general formula (wherein R and R1 are the general formula (1 )) and in the presence of an alkali, the coupler or the amine is tetnozonium or hexazonium, and the form of fluoridation is the same as that of alkali. Vc is easy to couple with the canoler before Mjj in the presence of an alkali in mDk such as N-dimethylformamide, dimethyl sulfoxide, etc.
can be manufactured.

The 'Ichikosha p-photoreceptor of the present invention has a photosensitive layer containing an azo pigment represented by the above general formula (1).
-, and can be used on any type of electronic '-I-i- page photoreceptor of the above-mentioned (1) to (V), but - gauze type (
The cage caused by the light absorption of the Azo face shown in 1)
In order to increase the transport efficiency of
It is preferable to use it as a photoreceptor of type (iii) or (iv).

Furthermore, the generation function and the supporting function of the charge ratio body are separated (7.
i) type of photoreceptor takes advantage of the characteristics of the pigment,
Mo Desi 1 (7i.

The details of the 7'ζ-type capacitor and photoreceptor will be described in detail.

As for the layer structure, a conductive layer, a charge generation layer, and a charge transport layer are essential, and the charge generation layer may be the second part or the lower part of the charge transport layer. For the type 1, which is used repeatedly for IFP, in the case of a high-quality light body, it is mainly from the aspect of physical strength, and in the case of a non-conductor, from the aspect of chargeability. Music delivery;
It is preferable to stack the areas in the order of -. In order to improve the contact layer (<1) between the 2nd layer and the 11th charge generation layer, an absorbing layer can be provided as necessary.

As a single layer of cotton, a metal sheet such as aluminum or a metal strip, a metal sheet such as aluminum, a plastic film or a sheet of aluminum foil glued together with paper, and a metal sheet made of aluminum or other metals such as aluminum foil are used. ! Full paper is used.

Effective materials for the adhesive layer include resins such as casein, polyvinyl alcohol, water-soluble polyethylene, and nitrocellulose. The thickness of the adhesive layer is 01-5μ, preferably 0
5~3μ is appropriate.

On the conductive layer 5 or the dipping layer applied to the Noshima electric helmet, as shown by the general formula (1): 1], it is possible to apply it without a binder or without a binder after it has been made into particles. Separate it into a suitable binder tray, apply it and dry it.

For dispersing the azo pigment, known methods such as ball milling and attritor can be used, and the particle size is preferably 5 μm or less, preferably 2 μm or less, and most preferably 0.5 μm or less.

AzoIt spear) can also be applied by dissolving it in an amine solvent such as Eboureni/diamine. Conventional methods such as blade, Mayer bar, and spray dipping are used for dispensing.

The thickness of the charge generating jml is preferably 5μ or less, preferably 001 to 1
μ is desirable. When a binder is used in the charge generation layer, a large amount of binder will affect the sensitivity, so the ratio of the binder in the charge generation layer is preferably 80% or less.
Desirably 0% or less.

1. Binters that have been used include polyhinyl butyral, vinyl briacetate, polyester, polycarbonate,
Resins such as phenoxy resin, acrylic resin, polyacrylamide, polyamide, polyvinyl-lepyridine resin, cellulose resin, urethane resin, ebony tree), casein, polyvinyl alcohol, etc. are required.

On the charge generation layer provided in this manner,
j Provide a feeding layer.

If the transport material does not have film-forming ability (17), a solution prepared by diluting the binder in a suitable organic solvent is applied and dried in the same manner as described above to form a charge transport lω.

Charge transporting substances include electron transporting substances and stamp transporting substances.

Examples of electron transporting substances include chloranil, pulmoanil, tetracyanoethylene, tetracyanoquinodimethane,
2,4.7-) IJ nitro-9-fluorenone, 2
, 4,5.7-titranitrofluorenone, 2,4.7
-1-Lietro 9-dicyanomethylenefluorenone,
2,4,5.7-titranitroxanthone, 2,4,8
．． - Electron-withdrawing substances such as trinidrothioxanthone and polymerized versions of these electron-withdrawing substances are available.

Examples of suitable substances for transporting real tags include (11) (12) 2 Hs pyrazolines (1) ■-Phenyl-3-(4-N, N-shenamyl acinosnaryl)-5 to (4-N, N-diethylaminophenyl) pilaf IJ no(2)l-phenyl-3
-(4-N,N-nno"robilsnaril) -5-(4
-N, N-diethylaminophenyl) pyrazoline (3) ■-phenyl-3- (4-N,
dibennol)'minofuconinyl 9hyfusoline (4)]-
(bilinru(21'J -3-C4-N, N-diethylaminostyryl)-!>-(4-N.

N-7 aminophenyl) to lasolin (5)]-
]4quinolyl2) J-3-(4-N, N-diethylaminostyryl)-5-(4,-N.

N-diethylaminophenyl)pyrazoline (6) 1-(
Gynolylu(4))-a-(4-N, N-diethylaminostyryl)-s-(4-N.

So゛N-shi:rniej-ruaminoneenyl)pifrinha(711-(3-7togyshibilisol(2))-3-
(4-N,N-diethylaminostyryl)-5-(4-
li, N-diethylaminophenyl)pyrazoline (811-[Levidyl(2):) -3-(4-N
, N-diethylaminostyryl) -ri-(
4-N,N-diethylaminophenyl)pyrazoline (9) 1-phenyl-3-(4-N,N-diethylaminostyryl)-4-methyl-5-(4-N.

N-diethylaminophenyl) human (111-
Phenyl-3-(α-methyl-4-N.

N-diethylaminostyryl, )-5-(4-N.

N-diethylaminophenyl) Bia So! J N (11
)1-4 Virigirou (3) ) -3...(4-N,N
-diethylaminostyryl) -5-(4,-N,
N-diethyl aminophenyl) pyrazoline (2) 1-
Phenyl-3-(α-benzyl-4-N.

N-diethylaminostyryl)-5-(4-N.

N-diethylaminophenyl)pyrazoline (1) 1
．． 1-bis(4-N,N-dimethylaminophenyl)propane (2) 1.1-bis(4-N,N-diethylaminophenyl)propane (3) 1.1-bis(4-pr, N- chevruamino-2-y'f-ruphenyl) furopane (4) 1.1-bis(4-N,N-di'ninalamino-2-methoxyphenyl) soropane (5) 1.1-bis(4-N,N-dibenzyl) Amino
2-methylphenyl)-2-nolpropane (6) L
1-Bis(4-N,N-diethylamino-2-methylphenyl)-2-phenylpropane(7)1,1-his(4-N,N-diethylamino-2-methylphenyl)
He7ta7 (8) 1.1-bis(4-N,N-dibenzylamino-
2-Methylphenyl) -1-synchrohexylmethane (9) 1,1-bis(4-N,N-dimethylaminophenyl)pentane (111,1-bis(4-N,N-dibenzylamiturphenyl) Normasifthane triarylalkanes (1) 1,1-bis(4-N,N-dimethylaminophenyl)-1-phenylmethane (2J1,1-bis(4-N,N-diethylaminophenyl)-1-phenyl Methane (3) 1,1-bis(4-N,N-diethylamino-2
-methylphenyl)-1-phenylmethane (4) 1,1
-bis(4-N,N-diethylamine-2-etherphenyl)-2-phenylethane(511,1-bis(4-
N,N-diethylamine-2-methylphenyl)-3-
Phenylpropane (6) 1,1-bis(4-N,N-diethylamino-2,5-dimethoxyphenyl)-3-phenylpropananyl) -1,3,4,,-oxadylzole (2) 2
,5-bis(4-N,N-diethylamine phenyl-1
,3,4-oxadiazole(412,5-bis(4-
N,N-diethylaminophenyl) -1,3,4-oxadiazole (5) 2,5-bis(4-N,N-dibenzylaminophenyl) -1,a,4-oxadiazole (6) 2-Methyl-5-(3-carbazolyl)-
1゜3.4-oxadiazole (7) 2-ethyl-5-(3-carbazolyl)-1゜3
．． 4-Oxadiazole (8) 2-ethyl-5-(9-ethyl-3-carbazolyl) -1,a, 4-oxadiazole (9) 2-N
, N-diethylamino-5-(9-ethyl-3-carbazolyl)-1,3,4-oxadiazole(112-styryl-5-(3-carbazolyl)-1,
3,4-Oxadiazole (1) 9-styrylanthracene (2) 9- (4-N , N-dimethylaminosteryl) anthracene (3) 9- (4-N , N-diethylaminosteryl) anthracene ( 4) 9-(4-N, N-dibenzylaminostyryl)anthracene (5) 4-bromo-9-(4-N,N-diethylaminostyryl)anthracene (6) α-(9-anthryl)-β- (3-carbazolyl)ethylene (7) α-(9-anthryl)-β-(9-ethyl-3-carbazolyl)ethylene oxazole (1) 2- (4-N, N-diethylaminophenyl)-4- (4-N,N-dimethylaminophenyl)-S-(2-chlorophenyl)oxazole (2)
2- (4-N, N-diethylaminophenyl)
-5-Phenyloxazole (3) 4- (4-N, N-dimethylaminophenyl)-5-(2-, l/fluorophenyl)oxazole (4) 2- (4-N, N-dimethylaminophenyl)- 4,5-diphenyloxazole is) 2-(4-N,N-dimethylaminophenyl)-4-(4-N,N-diethylaminophenyl)-5-(2-chlorophenyl)oxazole (s)
2.5-di(2-chlorophenyl)-4-(4-N
, N-diethylaminotubonyl)Axazole, and the like. Others include pyrene, N-ethylcarbasol, trinoenyl 7mine, poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinyl acridine, poly-9-vinylphenyl anthracene, Pyrene-formaldehyde at II+, ethyl carbazole formaldehyde resin, etc. can also be used. The charge transport material is not limited to those described here, and when used, heavy charge transport materials or a mixture of two or more kinds of charge transport materials can be used.

However, when an electron-transporting substance and a hole-transporting substance are mixed, charge transfer absorption occurs in the visible region, and even when exposed to light, the light may not reach the charge-generating layer located below the charge-transporting layer. be. The thickness of the charge transport layer is preferably 5 to 30μ, and IcJ:
8=2oμ.

As the binder, acrylic resin, polystyrene, polyester, polycarbonate, etc. can be used. As the binder for the low-molecular hole-transporting substance, a hole-blocking polymer such as the aforementioned boIJ-N-vinylcarbazole may be used as the binder. - USP 4122 for Bansei Molecule's electron-transporting substance Banku
This can be achieved by using a conjugate of electron-transporting monomers as shown in No. 113.

When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, if the charge transport material is made of an electron transport material, the surface of the charge transport layer must be actively charged. When post-exposure, the charge generation layer forms in the exposed area.
The generated/jin blood cells are injected into the charge transport layer, and then
When the positive charge reaches the surface of the middle ear 1, the surface potential attenuates and an electrostatic contrast occurs between it and the unexposed area. A visible image can be obtained by developing the electrostatic latent image thus formed with a negatively charged toner. This is directly fixed at Mf, or the toner image is transferred to paper, plastic twill J, etc., and then developed.
It is also possible to stay in place for a certain amount of time.

A method for transferring the static WC latent image on the shredded photoreceptor onto the insulating layer of transfer paper, then developing and fixing it! Sign. Any of the developer ridges, developing method, fixing method (d), and known methods may be used without being limited to a specific method.

On the other hand, if the charge transport material is a hole-transporting material, the surface of the charge transport layer must be negatively banded, and when imagewise exposed after charging, the holes generated in the charge generation layer in the exposed area become t.
[#I neutralizes the negative charge that is injected into the transport layer and then reaches the interlayer, and a 1-square reduction occurs on the surface, creating a 1-4P charge contrast with the unexposed area. arise. There are 14 cases in which a positively charged toner is used during development, contrary to the case where an electron transporting substance is used.

(1) Type 11 The photoreceptor is an insulating binder solution such as that used in the charge transport layer of type (iii) photoreceptors, and an azo pigment represented by the general formula (1) is added to it.17 Dispersion wave conduction It is obtained by coating and drying on a support.

(11) type photoreceptor is an insulating film such as that used for the charge transport material and charge transport layer of type (III) photoreceptor.
Under each attack - 11 f6i agent 2'5 Rikikawa A, jA,
-N'' After adding the azo pigment represented by formula (1), the dispersion plate was coated on a conductive support and dried.

J (ml type photoreceptor Δ111) When the electron transport material and hole transport material described for the type photoreceptor are combined, a charge transfer complex is formed, so the general formula (
It is obtained by adding the azo pigment shown in 1), dispersing it, coating it on a conductive support and drying it.

The azo dye 8+ used in any photoreceptor has the general formula (
At least 1 selected from 1) Azo fA4 different
Contains all of Ochi's pigments, and if necessary, combines pigments with different light absorption to make a photoreceptor, which can be used to create a photoreceptor with increased density, non-chromatin, etc. For this purpose, it is also possible to use a combination of two or more azo pigments represented by the general formula (1), or to use them in combination with a charge-generating material selected from known dyes and pigments.

Akira's Kameko photographic photoreceptor can be used in electrophotographic copying machines.

Next, the azo pigment used in the present invention will be specifically explained in synthesis examples.

2.5-di(araminophenyl)-1,3,4-oxadiazole, 4.52 g ((1,0179 mol)
Water 55ml1. After cooling the separation solution consisting of concentrated W ('V iO,o ml) to 4°C,
g (0,0376 mol) in 9 rJ of water was reduced for 15 minutes, and then the solution r14. The mixture was kept at 3-6°C and stirred for 30 minutes, then activated carbon was added and filtered to obtain a tetrazonium solution.

Next, add 17.8 g of sodium hydroxide to 3.80 ml of water.
.

8-(ethylbenzoyl-amino)-naphthol (2)
11.5 g (0,0395 mol) was dissolved in #, and while keeping this solution at 6 to 8°C, the tetrazonium aqueous solution synthesized earlier was completely dissolved in 30 minutes, and after stirring for 2 hours,
It was left at room temperature overnight.

After filtering the reaction solution and washing the resulting pigment with water,
(135 g of Japanese pigment obtained from Shichiton Shujo, Dry House).

Using DM, F", THF, Yoguchi Shio,
Washed elemental content (high IR absorption spectrum tertiary amide 1645 teeth-1) Above, we have described the synthesis method of 1 pigment, but the general formula (1
) Other azo pigments shown are also synthesized in the same manner.

Next, implementation i+ll of the present invention will be shown.

Example 1 An aqueous polyvinyl alcohol solution was completely coated on an aluminum plate having a thickness of 100 μm and dried to form an adhesive layer of 0.8 g/m” per 11 coats.

Next, add 5 g of the cup 1 face and polyester (Adhesive 4).
9.000 manufactured by Tejubon, solid content 20%)” gz T
80 ml of HF was applied by IRC onto the above adhesive layer, and the coating amount after drying was 0.20 g/m''.

Next K, 4-N, N-diethylaminobenzaldehyde-N, N-diphenyl human 2 fufu 5gs polymethyl methacrylate tree 11 pieces (number average molecular weight 100,000) 5 g
kTHF 7 Cxre bath was coated on top of the heavy layer and the weight after drying was 10 g/m''.

The electrophotographic photoreceptor created in this way was tested using Kawaguchi Electric Co., Ltd.'s Seiden Copying Paper Testing Equipment! t Model 5P-428i was used for corona charging at θ5 Kv using a static method,
After being kept in a dark place for 10 seconds, it was exposed to light at an illuminance of 5 lux to examine the charging characteristics.

The initial potential is Vo (V), the potential retention rate for 10 seconds in the dark is 1 vB'l, and the half-attenuation exposure amount is 'c El/2 (lux・
8eo) This photoreceptor's band' shows all its characteristics.

Vo: θ520, Vk: 91%, El/2: 7
．． 81ux-1a Examples 2 to 22 P and A in the azo pigment represented by general formula (1).

5 g of an azo pigment in which R and R are as shown in Table 1 t/7m
and butyral resin (degree of butyralization 65 mol% 12 g'
The mixture was dispersed in a ball mill with a solution containing 95 ml of 1K of ethanol, and then coated on the adhesive layer using a Mayer bar to form a coating layer with a coating weight of 2 ft/m after drying.

The M solution for the cargo transport layer was applied using a Baker abplicator to give a dry and pulse wave film thickness of 10 g/g, slightly as used in Example 1. The charge 1 measurement of the photoreceptor was carried out in the same manner as in Example 1.

Table 1 shows the structure of the pigment used, and Table 2 shows the charging characteristics.

Table 2 Tei'zan: t+! J property Example 23 5 g of 2.4.7-ton trinitrofluoreno A and poly-4,4'-dioxydiphenyl-2,2-carbonate (viscous average molecule [30,000) 67 and 10 liters of tetrahydrofuran
In general terms, the coating area after application and drying was set to 12 t/m''. Charge measurement was carried out in the same manner as in Example P111, and the characteristic values were as follows. However, the charge characteristics were omitted.

Vo: 520v Vk: 88% El/2: 1B, 71txx-aec Example 24 100 μ thick aluminum 4 with ammonia solution of casein on top 711] Dry, [11 stops, 0 q-/
A contact layer of m'' was formed.

Next, 2-(4-N',N-ethylaminophenanyl)-4-(4-N,iN-dimetalaminophenyll-5-(2-ly(1ruphenyl)oxasol 5y)
-TopoIJ-N-Vinylcarbasol 57 (number average molecular weight 30 h) i Used in Example 5 in a solution dissolved in 10 ml of tetrahydrofuran, 45 Fisheries 1. After applying and dispersing Og to the full depth, it was applied to the above adhesive layer and dried, resulting in a coating of 1, 12 and 9 coats.

The photoreceptor thus prepared was subjected to band measurement in the same manner as in 1, and the measurements were as follows. However, it is yellowish and the polarity is ■ and lζ.

Vo □ Q) 500 V Vk:91]%ノE]1/2 2 20.4 1 uXl;+,
<Example 25 1-phenyl-3(D-diethyl-diminosti(4-noconinyl-inphthalate-terephthalate) (isophthalic acid prephthalic acid molar ratio l:1) 5!i''k tetrahydronorane TOml(r After dissolving this, 1.Of the 1C&1BF4 material used in Example 1 was added, and after dispersion, it was coated on the adhesive layer used in Example 9 and dried.
It was set to Δn9.

Ivy. 114 shi belt 114. It was the first time for tj.

V'o: IEI 525
■vk: 91%E1/2
2 To 1781uXa8ec Example 26・3
0 Pigment 5 of 1% 11 that was J]1 in Example 11? and butyral 1 fat (butyralization degree 63 mol%) 2 ft. ethanol 95 ntg (dissolved liquid and 4 VC-dispersed), coated on the aluminum surface of aluminum vapor-deposited isophthalic acid, and after drying. (1,2Vfn,'') Next, add the electrical lamp shaft material 5J shown in S3 and the phenoxy resin (Bakelite P K HH manufactured by UCC) 5y- to T.
A solution containing HF70 and Litholytic L7 was applied to the charge generation layer and dried to form a charge transport layer having a coated area of lt Vm''.

The photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1, and its characteristics are shown in Table 4.

Table 3 Charge transport materials luri4　　’＄　’＠　　June’ire.

Applicant: Gyanon Co., Ltd. 331-

Claims (1)

[Scope of Claims] An electrophotographic photoreceptor having an entire photosensitive layer, wherein the photosensitive layer contains an azo pigment having at least one azo group bonded to a coupler residue represented by the following general formula in the molecule. Characteristic electrophotographic photoreceptor. General formula (wherein R represents an optionally substituted alkyl group (~ represents an aryl group; R1 represents an optionally substituted aryl group).