JPS6010256A - Photoconductive film - Google Patents

Abstract

PURPOSE:To obtain a photoconductive film high in sensitivity and durability by using an azo pigment having at least one azo group combined with a specified coupler residue as a photoconductive film suitable for an electrophotographic sensitive material. CONSTITUTION:A photoconductive film contains an azo pigment having at least one azo group combined with a coupler residue represented by the general formula shown on the right in which R1-R7 are each H, halogen, or univalent org. residue, and at least one couple of R1 and R2, R3 and R4, R4 and R5, R5 and R6, R6 and R7 may form an optionally substd. aromatic ring. As a result, the obtained electrophotographic sensitive material has high sensitivity and high durability each in a practicable degree, and no problem in resistances to heat, humidity, light fading, etc., and superior characteristics.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photoconductive coating suitable for an electrophotographic photoreceptor, and more particularly to a photoconductive coating suitable for an electrophotographic photoreceptor using a specific azo pigment. It is something.

Conventional photoreceptors containing organic pigments on a conductive layer include: (1) A layer in which a pigment is dispersed in an insulating binder on a conductive layer as disclosed in Japanese Patent Publication No. 52-1667 (electrophotographic plate); (11) JP-A-47-
Publication No. 30328 (electrophotographic plate), JP-A-47-
A layer in which pigments are dispersed in a charge transporting medium consisting of a charge transporting material or the material and an insulating binder (the binder itself may be a charge transporting material) as disclosed in Publication No. 18545 (electrophotographic imaging method) is formed on the conductive layer. A device comprising a conductive layer, a charge generating core containing an organic pigment, and a charge transport layer as disclosed in JP-A-49-105567 (electrophotographic plate) (V) JP-A-49-105567 (electrophotographic plate) -9164
There are also those in which an organic pigment is added to a charge transfer complex as disclosed in Publication No. 8 (Photoconductive Coating), (V) and others.

Pigments used in such photoreceptors include phthalocyanine pigments, polycyclic quinone pigments, azo pigments, and quinac 4
A number of pigments have been proposed, including lydone pigments.
It is rare to find something so scary that it has been put into practical use.

The reason is that organic photoconductive pigments are inorganic Se + Cd
This is because it is inferior to S, ZnO, etc. in terms of sensitivity and durability.

On the other hand, inorganic photoreceptors also have problems; Se-based photoreceptors easily crystallize due to factors such as temperature, humidity, dust, and fingerprints, and crystallization occurs particularly when the ambient temperature of the photoreceptor exceeds around 40°C. There are drawbacks such as a noticeable decrease in charging properties and white spots appearing on images. Although the lifespan of Se-based photoreceptors is said to be around 30,000 to 50,000 copies, because environmental conditions vary widely depending on the region and location where the copier is installed, many photoreceptors do not live up to the aforementioned lifespan. This is the current situation.

In the case of a CdS photoconductor cut into a plate with an insulating layer, the lifespan is comparable to that of a Se-based photoconductor, but it is extremely difficult to overcome the poor moisture resistance caused by CdS by using a solid layer, which prevents the photoconductor from absorbing moisture. The current situation is that supplementary means such as heaters are required to do this.

In the case of the Zn012 photoreceptor, it is sensitized with a dye such as rose bengal, so there are problems such as deterioration due to energization due to corona charging and photofading of the dye, so the lifespan of the photoreceptor is currently limited to around 1000 copies. has been done.

The sensitivity of conventional photoreceptors is half-attenuated 7'h'l light u (El/2
) is an unsensitized Se-based photoreceptor with 1
57ux-around Qi, sensitized 4-81ux-5Q
The CdS photoconductor has a sensitivity comparable to that of sensitized Se, and the ZnO photoconductor has a sensitivity of 7 to 12 A'.
It is about ux-dew.

As for the sensitivity of a practical photoreceptor, the E1/2 value is 20 j? for a PPC copying machine. It is desirable that it be ux-sec or less, and for PPC copiers with high copying speeds, it is more desirable that it be 151 uycsm or less. However, depending on the application, it may be possible to use it even if the sensitivity is less than the above-mentioned sensitivity.

The present inventors have made extensive efforts to overcome the drawbacks of conventional inorganic photoreceptors and improve the drawbacks of organic electrophotographic photoreceptors that have been proposed so far, and as a result, the following general formula (1) has been found in the molecule. At least one azo group bonded to the coupler residue represented by
A photoreceptor containing all azo pigments, preferably two or three types, has high sensitivity and high durability for practical use, and also has heat resistance (8
The present invention has been achieved based on the discovery that an excellent electrophotographic photoreceptor can be obtained which solves problems such as crystallization (crystallization of e), moisture resistance, and photobleaching resistance.

General formula (1) In the general formula (υ), R1-R2 represent a hydrogen atom, a halogen atom (chlorine atom, bromine atom, iodine atom) or a monovalent tangential residue.As a monovalent organic residue can be selected from a wide range of options, but especially alkyl groups (
Methyl, ethyl, n-propinoheisoprovil, n-butyl, t-butyl, n-amyl, n-hexyl, n-octyl, 2-ethylhexyl, t-octylnato), alkoxy groups (methoxy, ethoxy, propoxy, butoxy ), J: substituted or un14-substituted aryl group (phenyl, tolyl, xylyl, ethylphenyl, methoxyphenyl, ethoxyphenyl, chlorophenyl, nitrophenyl, dimethylaminophenyl, α-naphthyl, β
-naphthyl), substituted or unsubstituted aralkyl groups (benzyl, 2-phenylethyl, 2-phenyl-1-
methylethyl, bromobenzyl, 2-bromophenylethyl, methylbenzyl, methoxybenzyl, nitrobenzyl)1. Acyl groups (acetyl, gropionyl, butyryl, valeryl, benzoyl, triooyl, naphthoyl,
phthaloyl, furoyl, etc.), substituted or unsubstituted amino groups (amino, dimethylamino, diethylamino, dipropylamino, acetylamino, benzoylamino, etc.), ii'\: substituted or unsubstituted styryl group (styryl, dimethylaminostyryl, diethylamino), Styril,
diethylaminostyryl, methoxystyryl, ethoxystyryl, methylstyryl, etc.), nitro group, hydroxy group, carboxyl group, cyano group or]? Mono-substituted or unsubstituted arylazo group (phenylazo, α-naphthylazo, β-naphthylazo, dimethylaminophenylazo,
chlorophenylazo, nitrophenylazo, methoxyphenylazo, tolylazo, etc.).

Also, R1 and R2, R3 and R4, R4 and R6, R7 and Ro
and ■ aromatic rings substituted or unsubstituted with at least one combination of the combinations of import and R7 (benzene, naphthalene, chlorobenzene, bromobenzene, methylbenzene,
ethylbenzene, methoxybenzene, ethoxybenzene, etc.).

The azo pigments used in the present invention are monoazo pigments, disazo pigments, and trisazo pigments represented by the following general formula (2).

where R1-R7 have the same definitions as defined above.

A represents monovalent, divalent, and trivalent organic residues having at least one conjugated double bond. 0 These organic residues include hydrocarbon groups having a double bond system, Examples include a hydrocarbon group having a nitrogen atom or an organic residue having an aromatic ring and a heterocycle. Further, the organic residue having an aromatic ring and a heterocycle may have the aromatic ring bonded to the heterocycle, or may have the aromatic ring condensed with the heterocycle. n is 1,2
or 3.

A specific example of the above-mentioned organic residue is υ as shown below.

(12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24). 2H5 (25) (26) (28) Specific examples of the azo pigment represented by the general formula (2) are as follows.

M-(2) M-(3) M-(4) M-(s) CH.

Disazo pigment represented by general formula (2) D-(2) D-(3) D-(4) D-(5) D-(6) Trisazo pigment represented by general formula (2)＼ CH3 T -(2) T -(3) The electrophotographic photoreceptor of the present invention is characterized by having a photosensitive layer containing an azo pigment represented by the above general formula (2), and is characterized in that it has a photosensitive layer containing an azo pigment represented by the above general formula (2), and has the following characteristics: Although it can be applied to any type of electrophotographic photoreceptor, in order to increase the transport efficiency of charge carriers generated by light absorption of the azo pigment represented by general formula (2), (11), 011), 4V) It is desirable to use it as a type of photoreceptor.

Furthermore, the charge carrier generation function and transport function are separated 011)
This type of photoreceptor is most desirable in taking advantage of the characteristics of the pigment.

Therefore, this type of electrophotographic 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 either above or below the charge transport layer, but in an electrophotographic photoreceptor of the type that is used repeatedly. Mainly from the viewpoint of physical strength, and in some cases from the viewpoint of chargeability, it is preferable to form a conductive layer, a charge generation layer, and a charge transport layer in this order [9 layers]. An adhesive layer may be provided as necessary for the purpose of improving the adhesiveness between the conductive layer and the charge generation layer.

As the conductive layer, a metal plate such as aluminum, a metal foil, a plastic film on which metal such as aluminum is vapor-deposited, aluminum foil laminated with paper, paper treated with conductivity, etc. are used.

Effective materials for the adhesive layer include resins such as casein, polyvinyl alcohol, water-bathable polyethylene, and nitrocellulose. The thickness of the adhesive layer is suitably 0.1 to 5 microns, preferably 0.5 to 3 microns.

The general formula (2
) The azo pigment shown in ) is made into fine particles, and then dispersed without a binder or, if necessary, in a suitable binder solution, and then applied and dried.

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

The azo pigment can also be applied by dissolving it in an amine solvent such as ethylenediamine. Conventional methods such as blade, Mayer bar, and spray dipping are used for application.

The thickness of the charge generation layer is preferably 5μ or less, preferably o, oi to 1μ.
is desirable. When a binder is used in the charge generation layer, the sensitivity is affected if the binder content is large, so the proportion of the binder in the charge generation layer is preferably 80% or less, preferably 4 (1
The following are desirable.

The binder used is polyvinyl butyral,
Polyvinyl acetate, polyester, polycarbonate, phenoxy resin, acrylic resin, polyacrylamide,
Various resins such as polyamide, polyvinylpyridine resin, cellulose resin, urethane resin, epoxy resin, casein, and polyvinyl alcohol are used.

A charge transport layer is provided on the charge generation layer provided in this manner.

If the charge transport material does not have film-forming ability, a solution prepared by dissolving the binder in a suitable solvent is coated and dried in a conventional manner to form a charge transport layer.

There are charge transporting materials, electron transporting materials and hole transporting materials.

Examples of electron transporting substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane,
2,4.7-)IJ2)I:1-9-fluorenone, 2
, 4,5.7-titranitrofluorenone, 2.4.7
-) dinitro-9-dicyanomethylenefluorenone,
Examples include electron-withdrawing substances such as 2,4,5,7-titranitrone, and polymerization of these electron-withdrawing properties.

Examples of suitable hole-transporting substances include a]1 (1) 1-phenyl-3-(4-N,N-diethylaminostyryl)-5-(4-N,N-diethylaminophenyl)viraso (2) 1-phenyl-3-'(4-N,N-dipropylstyryl)-5-(4-N,N-diethylaminophenyl)pyrazoline (3)1-phenyl-3-(4-N,N -dibenzylstyryl)-5-(4-N, H-dibenzylaminophenyl)pyrazoline (4) 1-(pyridyl-(2):] -3-(4-N,
N-diethylaminostyryl)-5-(4-N.

N-diethylaminophenyl)pyrazoline (5) 1-(
Quinolyl-(2)) -3-(4-N, N-1diethylaminostyryl)-5-(4-N.

N-diethylaminophenyl)pyrazoline (6) 1-[
: quinolyl(4))-3-C4-N, N-diethylaminostyryl)-5-(4-N.

N-diethylaminophenyl)pyrazoline (7) 1-[
3-Methoxy-pyridyl-(2) ) -3-(4-N
, N-diethylaminostyryl)-5-(4-N,N-
diethylaminophenyl) pyrazoline (8) 1-4 revidyl (2))-3-(4-N, N
-diethylaminostyryl) -5-(4N.

Page ethylaminophenyl) pyrazoline (9) l-phenyl-3-(4-N,N-diethylaminostyryl)
-4-Methyl-5-(4-N,N-diethyladanophenyl)pyrazoline ((Q 1-phenyl-3-(α-methyl-4-N.

N-diethylaminostyryl)-5-(4-one α111-Cpyridyl-(3):l
N-diethylaminostyryl') -5-(4-N.

N-diethylaminophenyl)pyrazoline 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-dienalaminophenyl)propane (3) 1.1-bis(4-N,N- diethylamino-
2-MeF-ruphenyl)propane (4) 1.1-bis(4-N,N-diethylamino-
2-methoxyphenyl)propane (5) 1.1-bis(4-N,N-dibeny/dylamilopane (6) 1.'1-bis(4-N,N-diethylamiyi2-methylphenyl)-2- Phenylpropane (7) 1.1-bis(4-N,N-diethylamino'
-2-ethylphenyl)hebutane (8) 1.1-bis(4,-N,N-dibenzylami/-2-ethylphenyl)-1-cyclohexylmethane (9) 1.1-bis(4-N, N-dimethylaminophenyl)pentane (tO) 1,1-bis(4-N,N-dibenzylaminophenyl)n-butane triarylalkane (1) 1.1-bis(4-N,N-dimethylamino phenyl)-1-phenylmethane (2) 1.1-bis(4-N,N-diethylaminophenyl)-1-phenylmethane (3) 1.1-bis(4-N,N-diethylamino-
2-methylphenyl)-1-phenylmethane (4) 1.1-bis(4-N,N-diethylamino-
2-ethylphenyl)-2-phenylethane (5) 1.1-bis(4-N,N-diethylamino-
2-methylphenyl)-3-phenylpropane (6) 1.1-bis(4-N,N-diethylamino-
2,s-dimethoxyphenyl)-3-phenylpropane (1) 2,5-bis(4-N,N-dimethylaminophenyl)-1,3,4-oxadiazole (2) 2
．． 5-bis(4-N,N-diethylaminophenyl)
-1,3,4-oxadiazole (3) 2,5-bis(4-N,N-dipropylaminophenyl) -1,3
,4-oxadiazole (4) 2.5-bis(4-N
, N-dibenzylaminophenyl) -1,3,4-oxadiazole (5) 2-methyl-5-(3-power, luno(zolyl)-1,3,4-oxadiazole (6) 2 - Ethyl -5-(3-cal) 21,3.4-oxadiazole (7) 2-ethyl-5-(9-ethyl-3-carbazolyl) -1,3 ,4-oxadiazole(8)2-N,
N-diethylamino-5-(9-ethyl-3-carno(
zolyl) -1,3,4-oxadiazole (9) 2-styryl-5-(3-cal)(solyl)-
1,3,4-Oxadiazole (1) 9-styrylanthracene (2) 9-(,4-N,'N-dimethylaminostyryl)anthracene (3) 9-(4-N,N-diethylaminostyryl)
Anthracene<4) 9-(4-N,N-dibenzylaminostyryl)anthracene (5) 4-promo g-(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)-5-
(2-10lophenyl)oxazole (2) 2-(4-N,N-diethylaminophenyl)
-5-phenyloxazole (a) 4-(4-N,N-dimethylaminophenyl)
-5-(2-chlorophenyl)oxazole (4) 2-(4-N,N-dimethylaminophenyl) -4,5-diphenyloxazole (5) 2-(
4-N, N-dimethylaminophenyl)-4-(4-N
, N-diethylaminophenyl)-5-(2-chlorophenyl)oxazole (6) 2.5-di(2-chlorophenyl)-4-(
Examples include 4-N,N-diethylaminophenyl)oxazole. Others include pyrene, N-ethylcarbasol, triphenylamine, phoIJ-N-pi, nylcarbasol, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene. , pyrene-formaldehyde li￥, j fat,
Ethyl carbazole formaldehyde resin and the like can also be used.

The charge transport substance is not limited to those described here, and when used, one type or a mixture of two or more types of charge transport substances can be used. however,
When an electron-transporting substance and a hole-transporting substance are mixed,
Charge transfer absorption may occur in the visible region, and even when exposed to light, light may not reach the charge generation layer located below the charge transport layer. The thickness of the charge transport layer is 5 to 30 microns, preferably 8 to 20 microns.

As the binder, acrylic resin mipolystyrene, polyester, polycarbonate, etc. can be used. The binder for the low-molecular hole-transporting substance is poly, -N-, as described above. Hole-transporting polymers such as vinylcarbazole and binders for electron-transporting substances have US
A polymer of an electron transporting monomer such as that shown in No. 4,122,113 can be used.

When using a photoreceptor in which a conductive layer, a charge 1 generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged. Electrons generated in the charge-generating layer are injected into the charge transport layer in the exposed area and then reach the surface to neutralize the positive charge and attenuate the surface potential between the exposed area and the unexposed area. Electrostatic contrast occurs. A visible image can be obtained by developing the electrostatic latent @ created in this way with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper or plastic film and then developed and fixed.

Alternatively, a method may be used in which the electrostatic Zd image on the Ii & light body is transferred onto an insulating layer of transfer paper, then developed and fixed. The formulation, developing method, and fixing method may be any known method or methods and are not limited to any particular method.

On the other hand, when the charge transport material is made of a hole transport material, it is necessary to charge the surface of the charge transport layer negatively, and when exposure is performed after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , then neutralizes the negative charges that have reached the surface, increasing the surface potential of ? Ijj, attenuation occurs and electrostatic contrast occurs between the exposed area and the unexposed area. In the present case, it is necessary to use a positively charged toner, contrary to the case where an electron transport material is used.

The (1) type photoreceptor is made by adding an azo pigment represented by the general formula (2) to an insulating binder solution such as that used for the charge transport layer of the 011) type photoreceptor, and dispersing it onto a conductive support. Obtained by coating and drying.

(11) type photoreceptor is made by dissolving the charge transport material of the OID type photoreceptor and an insulating binder such as that used in the charge transport layer in a suitable solvent, and then adding four additives to the azo compound represented by the general formula (2). After adding and dispersing, it is obtained by coating and drying on a conductive support.

When the electron transport material and hole transport material described in the 011) type photoreceptor are combined, a charge transfer complex is formed.
It is obtained by adding the azo pigment shown in 2), dispersing it, coating it on a conductive support and drying it.

The azo pigment used in any photoreceptor has the general formula (2
) Contains at least one type of pigment selected from the azo pigments shown in A combination of 45 or more two kinds of azo pigments represented by the general formula (2), or a known dye,
It is also possible to use it in combination with charge-generating materials selected from pigments.

The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in electrophotographic applications such as laser printers and CRT printers.

In addition, the photoconductive film of the present invention can also be used for solar cells, optical sensors, and the like.

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

Synthesis Example 1: Disazo pigment of D-(1)] After cooling a dispersion consisting of 12.2 f of 3.3″-dimethoxybenzidine, 200 ml of water, and 30 ml of concentrated hydrochloric acid to 5°C,
A solution prepared by dissolving 7.22 of sodium nitrite in 15 ml of water was added dropwise into the above solution over a period of 30 minutes.Then, the temperature of the solution was maintained at 4 to 7°C and stirred for 30 minutes.Activated carbon was then added and filtered to obtain a tetrazonium solution. Ta. , 662% of 42-thioborfluoric acid was added to this tetrazonium solution, and the precipitate was suction-filtered.
After washing twice with cold water, the product was vacuum dried to obtain a tetrazonium salt of i5.4f.

Next, a liquid consisting of 5.7 t of guaiazulene and 450 ml of dimethylformamide was cooled to 2°C.

Tetrazonium salt obtained above 6. Of 'f: After adding to the solution and dissolving it, keep this solution at 4-8°C. The mixture was added dropwise to the LC liquid over 10 minutes, stirred for 2 hours, and left overnight at room temperature.

The crystals obtained by filtering the reaction solution were sequentially washed with DMF, benzene and ethanol, and then dried to obtain a purified pigment of 3.82. Yield based on tetrazonium salt: 43% Melting point = 22
Absorption spectrum of decomposed solution at 3℃: Xmax in dichloromethane solution
= 537 nm Elemental analysis: Calculated value of C44H4eN40 Analysis value C79,7179,61 H7,017,18 N 8.45 8.40 The synthesis method of the disazo pigment of D-(1) has been described above, but the general formula (2 ) Other azo pigments shown are also synthesized in the same manner.

Examples 1 to 12 Next, examples of the present invention will be described.Examples 1 to 12 A polyvinyl alcohol aqueous solution was applied and dried on an aluminum plate having a thickness of 100μ to form an adhesive layer with a coating amount of o, s S' /m2.

Next, 2 g of the azo pigment shown in Table 1 and a butyral resin (degree of butyralization 63 mol%) 1. Or ethanol 577
After dispersing the solution, it was coated on the contact M layer to form a charge generation layer having a coating weight of 0.2 f/m2 after drying.

Then 4-N,N-diethylaminobenzaldehyde-N
, N-diphenylhydrazone 52 and polymethyl methacrylate resin (number average molecular weight 100,000) 52 were dissolved in 70 ml of tetrahydrofuran and coated on the charge generation layer,
The coating amount after drying was 1217 m2.

The electrophotographic photoreceptor thus prepared was statically charged with corona at e5KV using an electrostatic printing paper testing device Model SP-'42B manufactured by Kawaguchi Denki ■, and held in a dark place for 10 seconds. It was exposed to light at an illuminance of 5 lux and its charging characteristics were investigated.

The initial potential is Vo (V), the potential holding rate for 10 seconds in the dark is Vk (%), and the half-attenuation exposure ht is E 1/2 (l!
Table 1 shows the charging characteristics of this photoreceptor.

Example 13 2,4-trinitrofluorenone 52 and poly-4,4'-dioxydiphenyl-2,2-carbonate (viscosity average molecular weight 30.0
00) 59 was bath-dissolved in 70 ml of tetrahydrofuran, and the coating amount after coating and drying was set to 187/rn2. Charge measurement was carried out in the same manner as in Example 1, and the characteristic values were as follows. However, the iY polarity was set as ■.

■o: 510v Vl (: 82% El/2: 21.51ux-x Example 14 An ammonia aqueous solution of casein was applied onto a 100μ thick aluminum plate and dried, resulting in adhesion with a coating weight of 1.0 g/m2. formed a layer.

Then, 2-(4-N,N-diethylaminophenyl)-
4-(4-N,N-dimethylaminophenyl)-5-(
2-10 ruphenyl) oxazole 5ri and poly N-vinyl carno (sol 52 (number average molecular fi 300,000),
Example 7 was dissolved in 70 ml of tetrahydrofuran.
After adding and dispersing 1.07 g of the pigment D-(5) used in Example 1, it was coated on the adhesive layer and dried to give a coating weight of 121/m2.

The photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1, and the measured values were as follows. However, the charging polarity was set to ■.

vo: 480V Vk: 82cmF; 1/2: 26.51ux-sv Example 15 1-phenyl-3(4-N,N-diethylaminostyryl)-5-(4N,N=-diethylaminophenyl)pyrazoline 51 and poly-2,2-furopane bis(
4-phenylisophthalic acid, terephthalic acid ester) (
After dissolving 5f (isophthalic acid, terephthalic acid molar ratio 1:1) in 70 ml of tetrahydrofuran, 1.07 g of the pigment of Todoroki D-(6) used in Example 8 was added, and after dispersion, the pigment used in Example 14 was added. Apply on the adhesive layer, dry, and apply a coating amount of 12
v/m2.

The photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1, and the measured values were as follows. However, the charging polarity was set to ■, ■o: ■520■ Vk: 89 t El/2: 21.51 ux-sw Examples 16 to 20 Pigment 22 of Tsubame D-(8) used in Example 9 and butyral After dispersing resin (butyralization degree 63 mol%) 1.02 with a solution dissolved in ethanol 572, it was applied to the aluminum surface of an aluminum vapor-deposited Mylar film, and the coating after drying (1r) was 0.21 i / m2. . Next, charge transport material 52 shown in Table 2 and phenoxy resin Bakelite (manufactured by CUCC) PKH,H)5ri';c T HF 70
A 4'6M solution was applied to the charge generation layer and dried.
A charge transport layer with a coating weight of 11 f/m2 was formed.

The photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1, and its characteristics are shown in Table 3.

Claims (1)

[Scope of Claims] A photoconductive broken film characterized by containing an azo pigment having at least one azo group bonded to a coupler residue represented by the following general formula (1). (In the formula, R, %R2, R3, R4, R1, R11 and R7 are hydrogen atoms, the parent halogen atom is a monovalent organic residue, and R7 and R, , R, and Ri, R= and Ri , R
At least one combination of s and R6 and R6 and R9 may form a substituted or unsubstituted aromatic ring. )