JPH02146048A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To prevent deterioration of chargeability due to preexposure fatigue and delay in rising of charging potential due to repeated uses by incorporating a specified electron acceptor in an electric charge generating layer. CONSTITUTION:At least a charge transfer layer and the charge generating layer containing at least one kind of the electron acceptors represented by formulae I - IV are formed on a conductive substrate. In formulae I - IV, R is alkyl, alkoxy, or the like, and each of p, q, m, and n is an integer of 0 - 4, thus permitting the obtained electrophotographic sensitive body to be small in deterioration of chargeability due to preexposure fatigue and freed of delay in rising of charging potential even after repeating cycles of charging and exposure.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to improvements in electrophotographic photoreceptors.

[Conventional technology]

In recent years, organic photosensitive materials, which have advantages such as low cost, productivity, and non-pollution, have become popular as photoconductors used in electrophotographic copying machines.

Organic electrophotographic photoreceptors include photoconductive resins such as polyvinylcarbazole (PVK), and PVK-TNF.
(2,4,7-dolinitrofluorenone), a pigment-dispersed type such as a phthalocyanine binder, and a functionally separated type photoreceptor using a combination of a charge-generating substance and a charge-transporting substance, etc. is known, and in particular, functionally separated photoreceptors are attracting attention.

When such a functionally separated high-sensitivity photoreceptor is applied to the Carlson process, it has low chargeability, poor charge retention characteristics (large dark decay), and is subject to repeated use. The deterioration of these characteristics is large on the two images.

It has the drawbacks of density unevenness, fogging, and background smearing in the case of reversal development.

Furthermore, in general, high-sensitivity photoreceptors have reduced chargeability due to pre-exposure fatigue. This pre-exposure fatigue is mainly caused by light absorbed by charge-generating materials, so the longer the charges generated by light absorption remain in the photoconductor in a mobile state, the greater the number of charges. It is thought that the lower the chargeability becomes, the more the chargeability decreases due to pre-exposure fatigue. In other words, even if a charging operation is performed while the charge generated by light absorption remains, the surface charge will be neutralized by the movement of the remaining carriers, so the surface potential will not increase until the residual charge is consumed. Therefore, the rise in surface potential is delayed by the amount of pre-exposure fatigue, and the apparent A;F potential becomes low.

For the above-mentioned drawbacks, for example, Japanese Patent Application Laid-Open No. 47-6341.
Nos. 48-3544 and 48-12034 have cellulose nitrate resin intermediate layers, as disclosed in JP-A No. 48-47344.52.
-25638.58-30757.58-63945.
58-95351.58-98739 and 60-66
No. 258 has a nylon resin intermediate layer, which is disclosed in Japanese Patent Application Laid-Open No. 49-6
Nos. 9332 and 52-10138 disclose a maleic acid resin intermediate layer, and JP-A-58-105155 discloses a polyvinyl alcohol resin intermediate layer. In addition, intermediate layers have been proposed in which various conductive additives are contained in a resin in order to control the electrical resistance of the intermediate layer.

For example, JP-A-51-65942 discloses an intermediate layer in which carbon or chalcogen-based substances are dispersed in a curable resin, and JP-A-52-82238 discloses an incyanate-based curing agent by adding a quaternary ammonium salt. The thermopolymer intermediate layer used is a resin intermediate layer containing a resistance modifier in JP-A-55-1180451, and a resin intermediate layer in which aluminum or tin oxide is dispersed in JP-A-58-58556. but,
JP-A No. 58-93062 discloses a resin intermediate layer containing an organometallic compound;
Nos. 363 and 60-111255 have a resin intermediate layer in which conductive particles are dispersed, and JP-A-59-84257.
Nos. 59-93453 and 60-32054 include Tie
, and SnO.

A resin intermediate layer in which powder is dispersed is disclosed.

However, it is still insufficient in terms of the deterioration in chargeability due to repeated use, especially the delay in the rise of the 4th charge, and further improvements have been desired.

Also, JP-A-53-26128 and 54-10943
No. 8 discloses an electrophotographic photoreceptor containing an electron-accepting substance in a charge generation layer, but these are fundamentally different from the present invention in one structure or effect.

Furthermore, based on the idea of controlling charge mobility instead of electrical resistance, a resin intermediate layer containing an electron-accepting organic compound as a negative charge mobility substance has been proposed. For example, JP-A No. 53-89433 discloses an organic polymer photoconductor intermediate layer containing a polycyclic aromatic nitro compound;
No. 47 and No. 59-170846 disclose resin interlayers containing electron-accepting organic substances. The above requirements were not necessarily met.

[Problem to be solved by the invention]

SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photoreceptor that is highly sensitive, exhibits significantly less deterioration in chargeability due to pre-exposure fatigue, and has no delay in the rise of charging potential even after repeated charging and exposure. do.

[Means to solve the problem]

According to the present invention, in a laminated organic electrophotographic photoreceptor having at least a charge generation layer and a charge transport layer on a conductive support, the charge generation layer contains the following - maximum (1) to general formula (r
There is provided an electrophotographic photoreceptor comprising at least one electron-accepting compound represented by V).

(In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and m and n represent integers of 0 to 4.) (In the formula, R
represents an alkyl group, alkoxy group or halogen atom, ρ
+ Q + l Hn represents an integer from 0 to 4. ) (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and m and n represent integers of 0 to 4.) (In the formula, R represents an integer of 0 to 4.
Alkyl group, alkoxy group or halogen atom, ■, n
represents an integer from 0 to 4.) As mentioned above, a highly sensitive laminated organic electrophotographic photoreceptor can be used repeatedly.
This causes a delay in the rise of electrification, resulting in a decrease in electrification properties. It was discovered that an electrophotographic photoreceptor with no delay in the rise of the electrification level after use could be obtained, and the present invention was completed.

The present invention will be described below with reference to the drawings.

FIG. 1 is a sectional view showing an example of the structure of the electrophotographic photoreceptor of the present invention, in which a photosensitive layer 15 consisting of a charge generation layer 21 and then a charge transport layer 22 is provided on a conductive support 11. .

FIG. 2 is a sectional view showing another example of the structure of the present invention, in which a photosensitive layer 15 consisting of a charge transport layer 22 and then a charge generation layer 21 is provided on a conductive support 11.

3 and 4 are cross-sectional views showing still another example of the structure, in which a subbing layer 13 is provided between the conductive support 11 and the photosensitive layer 15; Figure 4 shows the photosensitive layer 15.
A protective layer 17 is provided thereon.

As the conductive support 11, materials exhibiting conductivity with a volume resistance of 1010 Ω or less are used, such as metals such as aluminum, nickel, chromium, nichrome, copper, silver, gold, and platinum, and metal oxides such as tin oxide and indium oxide. Products coated on film-like or cylindrical plastics, paper, etc. by vapor deposition or sputtering, or plates made of aluminum, aluminum alloy, nickel, stainless steel, etc., and their adhesives.1. ．． 1.1. It is possible to use pipes that have been made into blank pipes by methods such as , extrusion, and drawing, and then surface-treated by cutting, superfinishing, polishing, and the like.

Next, the charge generation layer 21 will be explained.

The charge generation layer 21 includes a charge generation substance and at least one electron-accepting compound represented by the general formula (1) to general formula IV).
This layer is mainly composed of seeds, and a binder resin may be used if necessary.

Binder resins include polyamide, polyurethane,
Polyester, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone,
Polystyrene, poly-N-vinylcarbazole, etc. are used.

As the electron-accepting compounds represented by general formulas (1) to -general formula IV), those having the following chemical structural formulas are preferably used.

[-Specific examples of maximum (1) compounds] [-maximum (III) Specific examples of compounds of [-Max (TI) Specific examples of compounds of ~IJ.

[-Specific examples of maximum (1v) compounds] (However, Cp is a coupler residue, Same below) As a charge generating substance, Using known materials Although it is possible to Among others, there are the following disazo Alternatively, trisazo pigments are preferably used.

(However, R.

hydrogen atom, substituted or unsubstituted Represents an alkyl group.

(However, R is hydrogen atom, alkyl group, Halo Represents a gen atom.

(However, A is -Nl! -, It, -S-.

(However, n is Represents an integer between 1 and 5.

11.

N-('0ri)1 These coupler residues Cp include, for example, compounds having a phenolic hydroxyl group such as phenols and naphthols, aromatic amino compounds having an amino group, or amino compounds having an amino group and a phenolic hydroxyl group. Naphthols, compounds having an aliphatic or aromatic enolic ketone group (compounds having an active methylene group), etc. are used, and preferably those represented by the following maximum (1) to (11) are used.

X: -011, -N or -Nl(SQ,
-R.

(1 (1 and R2 represent hydrogen or a substituted or unsubstituted alkyl group, R3 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted 1-7 substituted aryl group.) Yl; hydrogen, halogen, substituted or an unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a carboxy group, a sulfone group, a substituted or unsubstituted sulfamoyl group, or -CON-'/2 (R4 is hydrogen, an alkyl group or a substituent thereof, a phenyl group, or represents its substituted form,
Y2 is a hydrocarbon ring group or a substituted product thereof, a heterocyclic group or [
In the above formulas (1), (2), (3) and (4), X,'
/, , Z, m and n each represent the following.

R6 is a hydrocarbon ring group or a substituent thereof, a heterocyclic group or a substituent thereof, a styryl group or a substituent thereof, RG
represents hydrogen, an alkyl group, a phenyl group, or a substituent thereof, or R6 and R6 may form a ring together with the carbon atoms bonded to them. ) is shown. ) Z: hydrocarbon ring or its substituted product, or heterocycle or its substituted product n: an integer of 1 or 2 m: an integer of 1 or 2] [In formulas (5) and (6), R1 is a substituted or unsubstituted It represents a hydrocarbon group, and X is the same as above. ]λ1
, [wherein R represents an alkyl group, a carbamoyl group, a carboxy group or an ester thereof, Ar1 represents a hydrocarbon ring group or a substitute thereof, and x is the same as above.

] [In the above formulas (8) and (9), R9 represents hydrogen or a substituted or unsubstituted hydrocarbon group, and Ar2 represents a hydrocarbon ring group or a substituted product thereof. ] Said general formula (1)
Examples of the hydrocarbon ring of Z in (2), (3) or (4) include a benzene ring and a naphthalene ring, and examples of the heterocycle (which may have substitutions) include an indole ring,
Examples include a carbazole ring, benzolane ring, and dibenzofuran ring. Examples of the substituent in ring 2 include halogen atoms such as chlorine atom and bromine atom.

Examples of the hydrocarbon ring group in Y2 or R5 include phenyl group, naphthyl group, anthryl group, pyrenyl group, etc.
Examples of the heterocyclic group include a pyridyl group, a thienyl group, a furyl group, an indolyl group, a benzofuranyl group, a carbazolyl group, and a dibenzofuranyl group.
Examples of the ring formed by combining R5 and R5 include a fluorene ring and the like.

(2) Substituents on the hydrocarbon ring group or heterocyclic group of 2 or R5 or the ring formed by R6 and R6 include methyl J, (, alkyl groups such as ethyl group, propyl group, butyl group, methoxy group, ethoxy alkoxy groups such as propoxy groups and butoxy groups, halogen atoms such as chlorine atoms and bromine atoms, dialkylamino groups such as dimethylamino groups and diethylamino groups, halomethyl groups such as trifluoromethyl groups, nitro groups, cyano groups, and carboxyl groups. group or its ester, hydroxyl group, -5o3Na
Examples include sulfonic acid groups such as.

Examples of substituents for the phenyl group of R4 include halogen atoms such as chlorine atoms and bromine atoms.

Representative examples of the hydrocarbon group in R7 or R9 are:
Examples include alkyl groups such as methyl, ethyl, propyl and butyl groups, aryl groups such as phenyl, and substituted products thereof.

1) In the hydrocarbon group of 7 or R1; a substituent includes an alkyl group such as methyl group, ethyl group, propyl group, butyl group, alkoxy group such as methoxy group, ethoxy group, propoxy group, butoxy group, Halogen atoms such as chlorine atoms and bromine atoms, and hydroxyl groups.

Examples include nitro groups.

Typical examples of the hydrocarbon ring group in Ar or Ar are phenyl group, naphthyl group, etc.
Substituents for these groups include alkyl groups such as methyl, ethyl, propyl, and butyl, alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy, nitro, chlorine, bromine, etc. Examples include halogen atoms, dialkylamino groups such as cyano groups, dimethylamino groups, and diethylamino groups.

Furthermore, among X, a hydroxyl group is particularly suitable.

Among the above coupler residues, the above-mentioned - maximum (
2) , (5) , (6) , (7) , (8
) and (9), and among these, those in which X in the general formula is a hydroxyl group are preferred. Also, among these, a coupler residue represented by the general formula (10)"-z-' (v4 and 2 are the same as above) is preferable, and more preferably a coupler residue represented by the general formula (Z, Y2 and R2 are the same as above). It is a coupler residue represented by .

Furthermore, among the above-mentioned preferred coupler residues, the general formula (12) or (13) ゛・z・Paz゛(Z, R2, Rs and RG are the same as above, and Ro.

Examples of such substituents include the above-mentioned substituent Y2. ).

The electron-accepting compounds and charge-generating substances shown above may be used alone or in combination of two or more.

The electron-accepting compound represented by the above-mentioned maximum (1) to general formula IV) is used in an amount of 0.01 to 1 part by weight per 1 part by weight of the charge generating substance.
It is applicable to use 0.00 parts by weight, preferably 0.1 to 0.00 parts by weight.
Parts by weight of IO.

The binder resin is suitably used in an amount of 0 to 100 parts by weight, preferably 0 to 100 parts by weight, based on 100 parts by weight of the charge generating substance.
-50 parts by weight.

The charge generation layer is formed by using at least one electron-accepting compound represented by formulas (1) to (V), a charge generation substance, a binder resin if necessary, and a solvent such as tetrahydrofuran, cyclohexanone, dioxane, or dichloroethane. It can be formed by dispersing using a ball mill, attritor, sand mill, etc., diluting the dispersion liquid appropriately and applying it.

Application can be performed using a dip coating method, a spray coating method, a bead coating method, or the like.

The thickness of the charge generation layer is approximately 0.01 to 5 m, preferably 0.1 to 27 m.

The charge transport layer 22 can be formed by dissolving or dispersing a charge transport substance and a binder resin in a suitable solvent, applying the solution, and drying the solution.

Charge transport materials include hole transport materials and electron transport materials.

Examples of the electron transport substance include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinone dimethane, 2,4,7-dolinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone,
2,4,5.7-tetranitroxanthone, 2,4°8
- trinidrothioxanthone, 2,6.8-trinitro-4toindeno(t,z-b)thiophen-4-one,
1,3,7-trinitrodibenzothiophenone-5,5
-Electron-accepting substances such as dioxide.

Examples of the hole-transporting substance include electron-donating substances represented by the following general formula, which are suitably used.

(In the formula, R1, R2, R3 and R4 represent a hydrogen atom or a substituted or unsubstituted aryl group, Ar represents a substituted or unsubstituted aryl group, and Ar and R1 are used together to form a ring. and n is an integer of 0 or 1.

) (However, R8 represents a lower alkyl group, a lower alkoxy group, or a halogen atom, n represents an integer of 0 to 4, and R
2 and R3 may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. ) (In the formula, R1 represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic residue, and R□
IRI may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a C8-C4 hydroxyalkyl group, a 01-C4 chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R2 and R1 are They may jointly form a nitrogen-containing heterocycle, and R4 and R3 may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom. ) (wherein R is a carbazolyl group, pyridyl group, thienyl group, indolyl group, or furyl group, or a substituted or unsubstituted phenyl group, styryl group, naphthyl group, or anthryl group (however, the above substituent is a di-lower alkylamino group, lower alkyl group, lower alkoxy group, halogen atom, aralkylamino group, or amino group) (wherein R1 and R are hydrogen atoms, lower alkyl groups, lower alkoxy group or di-lower alkylamino group, R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group, and n represents O or l. They may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenoxy group, or a halogen atom.) (In the formula, R represents a hydrogen atom, a halogen atom, a cyano group, or a lower alkyl represents a group, R,, R,, RG are hydrogen atoms,
It represents a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted benzyl group, and R41R5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, or a di-lower alkylamino group. ) (In the formula, Ar represents a naphthalene ring, an anthracene ring, a styryl group, or a substituent thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents a lower alkyl group or a benzyl group.) (In the formula, R represents a lower alkyl group or a benzyl group. □ is a lower alkyl group,
2-hydroxyethyl group or 2-chloroethyl group, R2 represents a lower alkyl group, benzyl group or phenyl group, R1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a di-lower alkylamino group or a nitro represents a group. ) (In the formula, R,, R2, R,, R,, R represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted di-lower alkylamino group, or a dibenzylamino group. , R6 represents a lower alkyl group or a benzyl group.) Ar-CH:N is ○ (wherein, R1 represents a hydrogen atom, a lower alkyl group, a chloroethyl group, or a hydroxyethyl group, and R2 represents a hydrogen atom or a halogen atom. R3 is a lower alkyl group, di-lower alkylamino group, diarylamino group, substituted or unsubstituted styryl group, substituted or unsubstituted aromatic ring residue (aromatic ring or benzene ring, naphthalene ring, anthracene ring, etc.), A substituted or unsubstituted heterocyclic residue (heterocycle represents a pyridine ring, a quinoxaline ring, a carbazole ring, etc.) (In the formula, Ro represents a lower alkyl group, and R2 represents a lower alkyl group, a di-lower alkylamino group. , diarylamino group, substituted or unsubstituted styryl group, substituted or unsubstituted aromatic ring residue (aromatic ring is a benzene ring, naphthalene ring, anthracene ring, etc.), substituted or unsubstituted heterocyclic residue (heterocycle is pyridine ring, quinoxaline ring, carbazole ring, etc.) (In the formula, R1 and R may be the same or different, and represent a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group,
It represents a chloro lower alkyl group, an acyl group having 1 to 2 carbon atoms in alkyl, a cycloalkyl group having 5 to 6 carbon atoms in alkyl, or a substituted or unsubstituted aralkyl group. ) These charge transport substances may be used alone or in combination of two or more.

Binder resins include polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester,
Polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral.

Polyvinyl formal, polyvinyltoluene, poly-N
- Thermoplastic or thermosetting resins such as vinyl carbazole, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin, phenol resin, and alkyd resin.

As the solvent, tetrahydrofuran, dioxane, toluene, monochlorobenzene, dichloroethane, methylene chloride, etc. are used.

The appropriate thickness of the charge transport layer 22 is about 5 to 100 μl. Furthermore, in the present invention, a plasticizer or a leveling agent may be added to the charge transport layer 22. As the plasticizer, those used as plasticizers for general resins, such as dibutyl phthalate and dioctyl phthalate, can be used as they are, and the appropriate amount to be used is about 0 to 30% by weight based on the binder resin.

Silicone oils such as dimethyl silicone oil and methylphenyl silicone oil are used as leveling agents, and the amount used is based on the binder resin.
Approximately 0 to 1 weight 2 is appropriate.

Undercoat layer 13 provided between support 11 and photosensitive layer 15
is provided for the purpose of further improving the effects of the present invention and improving adhesiveness, and its materials include Sin, [
1,03, inorganic materials such as silane coupling agents, titanium coupling agents, chromium coupling agents, and binder resins with good adhesiveness such as polyamide resins, alcohol-soluble polyamide resins, water-soluble polyvinyl butyral, polyvinyl butyral, and PVA. used. In addition, it is also possible to use a resin in which ZnO, TiO□, Z-port S, etc. are dispersed in the resin with good adhesive properties. As a method for forming the undercoat layer, methods such as sputtering and vapor deposition are used when an inorganic material alone is used, and when an organic material is used, a normal coating method is used.

Note that the thickness of the undercoat layer is suitably 5 μm or less.

The protective layer 17 is provided for the purpose of protecting the surface of the photoreceptor, and materials used for this include ABS resin, AC5 resin, olefin rubinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, and polyamide. , polyamideimide, polyacrylate, polyallylsulfone, polybutylene, polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate, polyimide,
Acrylic resin, polymethylpentene, polypropylene,
Examples include resins such as polyphenylene oxide, polysulfone, polystyrene, AS resin, butadiene-styrene copolymer, polyurethane, polyvinyl chloride, polyvinidene chloride, and epoxy resin. In addition, the protective layer may include fluororesins such as polytetrafluoroethylene, silicone resins, and inorganic materials such as titanium oxide, tin oxide, potassium titanate, etc. dispersed in these resins for the purpose of improving wear resistance. Can be added. A normal coating method is adopted as a method for forming the protective layer. The thickness of the protective layer is 0.
Approximately 5 to 10 μm is appropriate.

Furthermore, in the present invention, it is also possible to provide another intermediate layer (not shown) between the photosensitive layer 15 and the protective WJ 17.

〔Example〕

Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples.

Note that all parts used in the examples represent heavy foot parts.

Example 1 A charge generation layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied onto a polyethylene terephthalate film on which aluminum was vapor-deposited, and dried to form a charge generation layer with a thickness of 0.2 μm and a charge generation layer with a thickness of 22 μm, respectively. A charge transport layer was formed to produce an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

5 parts of a charge-generating substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula 150 parts of cyclohexanone 2-
Butanone 100 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula 10 parts Methanol 200 parts [Charge generation layer coating liquid] 2 parts charge generating substance having the following structural formula 1 part electron-accepting substance having the following structural formula Tetrahydrofuran 80 parts Example 2 On the same support as in Example 1, a subbing layer coating solution having the following composition,
A charge generation layer coating solution and a charge transport layer coating solution are sequentially applied and dried to form a subbing layer of 0.3 μm, a charge generation layer of 0.2 μm, and a charge transport layer of 20 μm, respectively. An electrophotographic photoreceptor was created.

[Subbing layer coating liquid]

↓ Cyclohexanone 2-butanone [Charge transport layer coating liquid] 200 parts of charge transport material with the following structural formula 100 parts 10 parts Water 150 parts Tetrahydrofuran 85 parts A subbing layer coating liquid, a charge generation layer coating liquid, and a charge transport layer coating liquid are sequentially applied and dried.
An electrophotographic photoreceptor of the present invention was prepared by forming a subbing layer of two parts each, a charge generation layer of 3 μlm, and a charge transport layer of 18 μm.

[Subbing layer coating liquid]

Titanium dioxide 10 parts Toluylene-2,4-diisocyanate 0.2 parts 2-butanone 100 parts 4-methyl-2-pentanone 70 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula 2 parts 1 part of electron-accepting substance Cyclohexanone tetrahydrofuran [Charge transport layer coating liquid] 120 parts of charge transport substance having the following structural formula 40 parts 9 parts Tetrahydrofuran 80 parts Example 4 On an aluminum plate with a thickness of 0.2 cm, a film having the following composition was coated on an aluminum plate with the following composition. A charge generation layer coating solution and a charge transport layer coating solution were sequentially applied and dried to form a charge generation layer of 0.2-m and a charge transport layer of 17 μm, respectively, to prepare an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

3 parts of a charge-generating substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula 9 parts of polycarbonate (GE
Lexan-141) Methylene chloride 82 parts Example 5 On an electroformed nickel plate with a thickness of 0.1 mm, a subbing layer coating liquid, a charge generation layer coating liquid, a charge transport layer coating liquid and A protective layer coating solution was sequentially applied and dried to form a subbing layer of 0.3 μl, a charge generation layer of 0.2 μl, a charge transport JPJ of 18 μl, and a protective layer of 3 μl. An electrophotographic photoreceptor was created.

[Undercoat layer coating liquid] 100 parts of tetrahydrofuran [Charge transport layer coating liquid] Charge transport substance having the following structural formula 9 parts water
,. . 1 part methanol
00 parts [Charge generation layer coating liquid] Charge generating substance having the following structural formula 5 parts Electron accepting substance having the following structural formula Part 3 Polysulfone (P-1700 manufactured by Nissan Chemical Co., Ltd.) Cyclohexanone tetrahydrofuran [Charge transport layer coating liquid] 2 parts of a charge transport material having the following structural formula: 100 parts: 90 parts: 12 parts: 2-butanone: 100 parts
A charge transport layer coating liquid and a charge generation layer coating liquid were sequentially coated and dried to form a 2 μm subbing layer, a 22-layer charge transport layer, and a 0.4 μs charge generation layer, respectively. A photographic photoreceptor was created.

[Subbing layer coating liquid]

Titanium dioxide 10 parts Methylene chloride [Protective layer coating solution] 100 parts 2-butanone 80 parts Ethyl acetate 80 parts [Charge transport layer coating solution] Charge transport substance with the following structural formula 10 parts Tin oxide 80 parts Toluene 170 parts Methylene chloride 40 parts 1,2-dichloroethane [Charge generation layer coating liquid] 40 parts of charge generation substance having the following structural formula; 3 parts; 20 μm charge transport Jt; 0.2 μm charge generation layer;
An intermediate layer of 0.2 μm and a protective layer of 5 μm were formed to produce an electrophotographic photoreceptor of the present invention.

[Charge transport layer coating liquid]

8 parts of a charge transporting substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula 0.5 parts of toluylene-2,4-diisocyanate 100 parts of tetrahydrofuran 4-
Methyl-2-pentanone 100 parts Example 7 On the same support as in Example 4, a charge transport layer coating solution, a charge generation layer coating solution, an intermediate layer coating solution and a protective layer coating solution having the following compositions were sequentially applied. , coated and dried, and then mixed with methylene chloride [Charge generation layer coating liquid] 80 parts of a charge generating substance with the following structural formula, 2 parts of an electron-accepting substance with the following structural formula, 1 part of an electron-accepting substance with the following structural formula, 70 parts of cyclohexanone 4-methyl-2-pentanone, 30 parts Part [Intermediate layer coating solution] 1 solution was applied and dried in order to form a charge transport layer of 19 μm each,
A charge generation layer of 0.3 μm and a protective layer of 2 μm were formed to prepare an electrophotographic photoreceptor of the present invention.

[Charge transport layer coating liquid]

Charge transport material having the following structural formula 10 parts Methanol n-butanol 70 parts 40 parts [Protective layer coating liquid] Tetrahydrofuran 70 parts [Charge generation layer coating liquid] Charge generating substance having the following structural formula 3 parts Conductive titanium oxide 90 parts toluene
220 parts n-butanol
60 parts Example 8 On a nichrome plate with a thickness of 0.2+n++, a charge transport layer coating solution having the following composition, a charge generation layer coating solution and a protective layer were all coated with an electron-accepting substance having the following structural formula: 1 part toluylene-2
, 4-diisocyanate 0.5 parts cyclohexanone 150 parts 2-butanone
50 parts [Protective layer coating solution] Tin oxide 90 parts Toluene 250 parts 2-butanone 70 parts Comparative Examples 1 to 8 In the photoreceptors of Examples 1 to 8 prepared as described above, each charge generation layer had an electron receiving layer. A photoreceptor was formed in the same manner as in Examples 1 to 8 except that no sexual substance was contained, and a photoreceptor was used as a photoreceptor in Comparative Example 1 to 8.

The characteristics of each photoreceptor described above were evaluated as follows using an electrostatic copying paper tester (newly manufactured by Kawaguchi Electric, Model 5P-428).

First, -5.2KV (or +5.6KV) (7
) After a long discharge, corona charging is performed for 20 seconds, and then dark decay is performed until the surface potential reaches 1800 VC or +800 VC.
When the temperature reached V), 4Qux tungsten light was irradiated.

The surface potential V at 1 second and 20 seconds after the start of charging at this time,
(V), V-O (V) Also, when irradiated with light, the surface potential is 2
The exposure amount E200 ((lux-sec) required to reach 00V or +200V) was measured.

Furthermore, this photoreceptor was irradiated with 50,000 Qux-sees of tungsten light having a color temperature of 2856"K to cause optical fatigue, and then Vo, v2°, and Eza were measured again in the same manner as above.

The evaluation results are shown in Table-1.

Table 1 Example 9 A charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially coated on a polyethylene terephthalate film on which aluminum was vapor-deposited, and dried to form a charge generation layer with an impression thickness of 0°2μ. Then, a charge transport layer having a thickness of 22 μm was formed to prepare an electrophotographic photoreceptor of the present invention.

[Charge generation 1-day coating solution] 5 parts of a charge generation substance with the following structural formula 2 parts of an electron-accepting substance with the following structural formula * Cannot be measured because it does not carry 800V 250 parts of cyclohexanone 100 parts of 2-butanone [Charge transport layer coating solution ] 9 parts of a charge transporting substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula 80 parts of tetrahydrofuran Example 10 On the same support as in Example 9, a subbing layer coating solution having the following composition,
A charge generation J coating solution and a charge transport layer coating solution are sequentially applied and dried to form a subbing layer of 0.3 threshold, a charge generation layer of 0.2 μm and a charge transport layer of 20 lines, respectively. An electrophotographic photoreceptor of the present invention was prepared.

[Subbing layer coating liquid]

Cyclohexanone 2-butanone [Charge transport layer coating liquid] Charge transport substance having the following structural formula: 70 parts 30 parts 10 parts water
150 parts methanol
200 parts [Charge generating layer coating liquid] Charge generating substance having the following structural formula 2 parts Tetrahydrofuran 75 parts Example 11 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, a subbing layer coating liquid having the following composition and a charge generating layer Apply coating solution and charge transport layer coating solution sequentially.

Coating and drying were performed to form a subbing layer of two types, a charge generation layer of 0.3 μm, and a charge transport layer of 18 μm, thereby producing an electrophotographic photoreceptor of the present invention.

(Undercoat layer coating liquid) Titanium dioxide 10 parts Cyclohexanone tetrahydrofuran [Charge transport layer coating liquid] Charge transport material having the following structural formula 100 parts 100 parts 7 parts Toluylene-2,4-diisocyanate 0.2 parts 2-butanone 100 Part 4
-Methyl-2-pentanone 70 parts [
Charge generation layer coating liquid] 2 parts of a charge generation substance having the following structural formula. 1 part of an electron accepting substance having the following structural formula. 70 parts of tetrahydrofuran. Example 12 A charge generation layer having the following composition was coated on an aluminum plate having a thickness of 0.211I11 The coating solution and the charge transport layer coating solution were sequentially applied and dried to form a charge generation layer of 0.2/a and a charge generation layer of 17 μm, respectively.
A charge transport layer was formed to produce an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

4 parts of a charge-generating substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula - 1 liquid and a protective layer coating liquid were sequentially applied and dried to give 0.
．． An electrophotographic photoreceptor of the present invention was prepared by forming a 3 μl subbing layer, a 0.2 μm charge generation layer, an 18-tile charge transport layer, and a 3 μm protective layer.

[Subbing layer coating liquid]

Tetrahydrofuran [Charge transport layer coating liquid] 200 parts of charge transport substance having the following structural formula: 10 parts water
100 parts methanol
100 parts [Charge generating layer coating liquid] Charge generating substance having the following structural formula 4 parts Methylene chloride 82 parts Example 13 A subbing layer coating liquid having the following composition was applied on an electroformed nickel plate having a thickness of 0.1 part wi. , charge generation layer coating liquid, charge transport layer coating: 3 parts of electron-accepting substance with the above structural formula; 1 part of polysulfone (P-1700 manufactured by Nissan Chemical Co., Ltd.); 1 part of cyclohexanone tetrahydrofuran [charge transport layer coating liquid]: with the following structural formula: forming a charge transport layer of 300 parts, 200 parts, and 9 parts of a charge transport material and a charge generation layer of 0.4 μm;
An electrophotographic photoreceptor of the present invention was prepared.

[Subbing layer coating liquid]

Titanium dioxide 1 part Methylene chloride [Protective layer coating solution] 80 parts 2-Butanone Ethyl acetate [Charge transport layer coating solution] Charge transport material with the following structural formula 10 parts 20 parts 10 parts Oxidation g 80 parts Toluene 170 parts 2- Butanone 100 parts Example 14 On the same support as in Example 9, a subbing 1d coating solution, a charge transport layer coating solution, and a charge generation layer coating solution having the following compositions were sequentially coated and dried to give 2 μl of each. Undercoat layer, 22-density methylene chloride 1,2-dichloroethane [charge generation layer coating liquid] 40 parts of a charge generation substance with the following structural formula 40 parts of an electron-accepting substance with the following structural formula 1 part methylene chloride [charge generation layer coating] Liquid] 80 parts of a charge generating substance having the following structural formula 0.2 parts of toluylene-2,4-diisocyanate 100 parts of tetrahydrofuran 4-methyl-
2-Pentanone 85 parts Example 15 On the same support as in Example 12, a charge transport layer coating solution, a charge generation layer coating solution, an intermediate layer coating solution, and a protective layer coating solution having the following compositions were sequentially applied. - A charge transport layer of 20 .mu.l, a charge generation layer of 0.2 .mu.l, an intermediate layer of 0.2 IA and a protective layer of 5 .mu.l were each formed by drying, thereby producing an electrophotographic photoreceptor of the present invention.

[Charge transport layer coating liquid]

Charge transport substance of the following structural formula 8 parts Electron accepting substance of the following structural formula Cyclohexanone 4-methyl-2-pentanone [Intermediate layer coating liquid] Methanol n-butanol 200 parts 150 parts 70 parts 40 parts [Protective layer coating liquid ] Charge generating material conductive titanium oxide having the following structural formula 90 parts Toluene 220 parts n-butanol 60 parts Example 16 A charge transport layer coating liquid having the following composition and a charge generating layer were coated on a nichrome plate having a thickness of 0.2 parts wn. The R1J coating solution and the protective layer coating solution were sequentially applied and dried to form a charge transport layer of 19 μI and a charge transport layer of 0.0 μI.
A charge generation layer of 3 μm and a protective layer of 2 μm were formed to prepare an electrophotographic photoreceptor of the present invention.

[Charge transport layer coating liquid]

Charge transport substance of the following structural formula 9 parts Electron accepting substance of the following structural formula Toluylene-2,4-diisocyanate cyclohexanone 2-butanone [Protective layer coating solution] 0.2 parts 60 parts 40 parts Tetrahydrofuran 100 parts [Charge generation layer Coating liquid] Tin oxide toluene 2-butanone Comparative Examples 9 to 16 90 parts 250 parts 70 parts In the photoreceptors of Examples 9 to 16 prepared as above,
Photoreceptors were formed in the same manner as in Examples 9 to 16, except that each charge generation layer did not contain an electron-accepting substance, and were used as photoreceptors of Comparative Examples 9 to 16.

The characteristics of each photoreceptor described above were evaluated as follows using an electrostatic copying paper tester (newly manufactured by Kawaguchi Electric, Model 5P-428).

First, corona charging is performed for 15 seconds at a discharge pressure of -5.5KV (or ÷5.4KV), and then dark decay is performed to reduce the surface potential to 1800V (or +800V).
When the temperature was reached, tungsten light of 6Qux was irradiated.

At this time, the surface potential V2 (2 seconds and 15 seconds after the start of charging)
v), Vl, (V) Also, when irradiated with light, the surface potential is -40
Exposure fE required to reach 0v or +400V)
406 (12ux-sec) was measured.

Further, this photoreceptor was irradiated with 7000012 ux-see of tungsten light having a color temperature of 2856° to cause photofatigue, and then the same procedure as above was carried out again. was measured.

The evaluation results are shown in Table-2.

*00V Table-2 Unable to measure because it does not ride Example 17 A charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried on a polyethylene terephthalate film on which aluminum was vapor deposited, and each was O0! A charge generation layer with a thickness of μm and a charge transport layer with a thickness of 22 μm were formed to produce an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

5 parts of a charge-generating substance with the following structural formula 1 part of an electron-accepting substance with the following structural formula [Charge transport layer coating liquid] 9 parts of a charge-transporting substance with the following structural formula 75 parts of tetrahydrofuran Example 18 On the same support as Example 17 Then, a subbing layer coating solution, a charge generation J-coating solution, and a charge transport layer coating solution having the following compositions were sequentially applied.
After coating and drying, a subbing layer of 0 and 3 pm, respectively, 0.2/
An electrophotographic photoreceptor of the present invention was prepared by comprising a charge generation layer of Js and a charge transport layer of 20IJm.

[Subbing layer coating liquid]

Cyclohexanone 2-butanone 200 parts 50 parts water
150 parts methanol
200 parts [Charge generation layer coating liquid] 3 parts of a charge generating substance having the following structural formula 1 part of an electron accepting substance having the following structural formula Example 19 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, a subbing layer having the following composition. The coating solution, the charge generation layer coating solution, and the charge transport layer coating solution are sequentially applied and dried.
Subbing layer in each corner, 0.3 tone charge generation layer and 18μ
A charge transport layer of m was formed to produce an electrophotographic photoreceptor of the present invention.

[Subbing layer coating liquid]

Titanium dioxide 10 parts Cyclohexanone 2-butanone [charge transport layer coating liquid] 60 parts 40 parts 7 parts et al.
-Methyl-2-pentanone 70 parts [
Charge generating layer coating liquid] 2 parts of a charge generating substance having the following structural formula 70 parts of tetrahydrofuran υ II] Sushi 113 1 part of an electron accepting substance having the following structural formula was applied and dried to form a charge generating layer with a density of 0.2 each and 11 part m
A charge transport layer was formed to produce an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

Charge generating substance with the following structural formula 2 parts cyclohexanone tetrahydrofuran [Charge transport layer coating liquid] 40 parts of charge transporting substance with the following structural formula 40 parts 10 parts Electron accepting substance with the following structural formula 1 part NO - Tetrahydrofuran 80 parts Example 20 On an aluminum plate with a thickness of 0.2 m, a charge generation layer coating solution and a charge transport layer coating solution having the following composition were sequentially applied: 90 parts of tetrahydrofuran [Charge transport layer coating solution] 10 parts of a charge transport substance having the following structural formula. Methylene chloride 100 parts Example 2F On an electroformed nickel plate with a thickness of 00 lIII+, a subbing layer coating solution, a charge generation 7M coating solution, a charge transport layer coating solution and a protective layer coating solution having the following composition were applied in sequence. Coating and drying each 0.
3μm subbing layer, 0.2μm charge generation layer and 18μm
A charge transport layer of m and a protective layer of 3 μnl were formed to produce an electrophotographic photoreceptor of the present invention.

[Subbiki J111 coating liquid] Water
100 parts methanol
100 parts [Charge generation layer coating liquid] 5 parts of a charge generating substance with the following structural formula 2 parts of an electron-accepting substance with the following structural formula Polysulfone (P-1700 manufactured by Nissan Chemical Co., Ltd.) Cyclohexanone tetrahydrofuran [Charge transport layer coating liquid] The following 2 parts of charge transport material with structural formula 300 parts 200 parts 10 parts Methylene chloride 80 parts [protection/('7 coating solution)] Tin oxide 80 parts Toluene 170 parts 2-butanone 100 parts Example 22 Same support as Example 17 On top, a subbing layer coating liquid, a charge transport layer coating liquid and a charge generation layer coating liquid having the following compositions were sequentially applied and dried to form a subbing layer of 2 μm each, a charge transport layer of 22 lines, and a charge transport layer of 0.0 μm. A charge generation layer of 4 pm was formed.

An electrophotographic photoreceptor of the present invention was prepared.

[Subbing layer coating liquid]

Titanium dioxide 1 part Methylene chloride 1,2-dichloroethane [Charge generation layer coating solution] Charge generating substance with the following structural formula Electron accepting substance with the following structural formula 60 parts 20 parts 15 parts 2-butanone 10 parts Ethyl acetate 20 parts [ Charge Transport Layer Coating Liquid] Charge transport substance having the following structural formula 9 parts Toluylene-2,4-diisocyanate 1 part Tetrahydrofuran 200 parts 4-Methyl-2-pentanone 500 parts Example 23 On the same support as Example 20, A charge transport layer coating liquid, a charge generation layer coating liquid, an intermediate layer coating liquid, and a protective layer coating liquid having the following compositions were coated and dried to form a charge transport layer of 20 pII+ and a charge of 0.2 μm, respectively. Generation layer, middle Jf of 0.2 voice
A protective layer of f, I and 5 μm was formed to prepare an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

Charge transport substance with the following structural formula IO part Electron-accepting substance with the following structural formula ~0- Cyclohexanone 4-methyl-2-pentanone [Interlayer coating liquid] Alcohol-soluble polyamide (Amilan CM-8000 manufactured by Toshi ■) Methanol n -Butanol [Protective layer coating solution] 400 parts 100 parts 70 parts 40 parts Methylene chloride [Charge generation layer coating solution] 160 parts of charge generating substance with the following structural formula 5 parts Conductive titanium oxide Toluene n-Butanol Example 24 Thickness On a nichrome plate with a diameter of 0.2 mm.

90 parts, 220 parts, and 60 parts of the following compositions: ``Import transport layer coating liquid'', charge generation FT4 coating liquid, and protective layer coating liquid were sequentially coated and dried to form a charge transport J cape having a thickness of 19 μm.

A charge generation layer of 0.3 μm and a protective layer of 2 μm were formed to prepare an electrophotographic photoreceptor of the present invention.

['r4i 4 parts transport layer coating liquid] Charge transport material having the following structural formula 10 parts Toluylene-2,4-diisocyanate cyclohexanone 2-butanone [Protective layer coating liquid] 1 part 75 parts 20 parts Tetrahydrofuran 100 parts [Charge generation layer Coating liquid] Charge-generating substance with the following structural formula 2 parts Electron-accepting substance with the following structural formula 1 part Tin oxide
90 parts toluene
250 parts 2-butanone
70 parts Comparative Examples 17 to 24 In the photoconductors of Examples 17 to 24 prepared as described above, photoconductors were prepared in the same manner as in Examples 17 to 24 except that each charge generation layer did not contain an electron-accepting substance. were formed to provide photoreceptors of Comparative Examples 17 to 24.

The characteristics of each photoreceptor described above were evaluated as follows using an electrostatic copying paper tester (newly manufactured by Kawaguchi Electric, Model 5P-428).

First, a -5.2KV (or +5.6KV) discharge is applied to the corona 91 for 20 seconds, and then the surface potential is 1800V (or +800V) after dark decay.
When the temperature reached V), tungsten light of 6Qux was irradiated.

At this time, the surface potential V at 1 second and 20 seconds after the start of 4HF electricity
, (V), VZ. m Also, when irradiated with light, the surface potential is 14
00V or +400V) was determined to be 411 times.

Furthermore, after irradiating this photoreceptor with tungsten light having a color temperature of 2856° (81) OOOQux-see to cause optical fatigue, vl, V, o, and El/2 are determined in the same manner as above.
ll! I decided.

The evaluation results are shown in Table-3.

Table 3 *AOOV No charging and no Okiyodomi Example 25 On a polyethylene terephthalate film deposited with aluminum, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried. A charge generation layer with a thickness of 0.2 μm and a charge transport layer with a thickness of 22 μm were formed to produce an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

3 parts of a charge-generating substance having the following structural formula 1 part of an electron-accepting substance having the following structural formula 1 part of a charge-transporting substance having the following structural formula A layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution are sequentially coated and dried, and each layer is coated with a 0.3μ peak of Jt'? ,0.2μ
... constitutes a charge generation layer and a charge transport J+4 of 20 tones,
An electrophotographic photoreceptor of the present invention was prepared.

[Subbing layer coating liquid]

Cyclohexanone 2-butanone [charge transport layer coating liquid] 100 parts 50 parts water
150 parts methanol
200 parts [Charge generation layer coating liquid] 2 parts of a charge generation substance having the following structural formula 1 part of an electron accepting substance having the following structural formula Example 27 On a polyethylene terephthalate film provided with a Hastelloy core layer, a subbing layer having the following composition. The coating solution, the charge generation layer coating solution, and the charge transport layer coating solution are sequentially applied and dried.
2 μl each of subbing layer, 0.3 μm charge generation layer and 1
A charge transport layer having a thickness of 8 μm was formed to produce an electrophotographic photoreceptor of the present invention.

[Subbing layer coating liquid]

Titanium dioxide 10 parts Cyclohexanone 2-butanone [charge transport Jt4 coating liquid] Charge transport substance having the following structural formula 70 parts 30 parts 10 parts Toluylene-2,4-diisocyanate 0.2 parts 2-butanone 100 parts 4
-Methyl-2-pentanone 70 parts [
Charge Generation Layer Coating Liquid] A charge transport layer was formed using 5 parts of a charge generation substance having the following structural formula: 75 parts of tetrahydrofuran and 1 part of an electron accepting substance having the following structural formula to prepare an electrophotographic photoreceptor of the present invention.

[Charge generation layer coating liquid]

Charge generating substance with the following structural formula: 4 parts cyclohexanone tetrahydrofuran (Coating liquid for heavy transport layer) Charge transporting substance with the following structural formula: 100 parts 100 parts 15 parts Electron-accepting substance with the following structural formula: tetrahydrofuran 100 parts Example 28 Thickness: 0 A charge generation layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried on an aluminum plate containing 0.2 parts wn of a charge generation layer having a thickness of 0.2 μm and a charge transport layer containing 11 parts m tetrahydrofuran [charge transport layer]. Coating liquid] 150 parts of a charge transport material with the following structural formula (Lexan-141, manufactured by GE Co., Ltd.) 10 parts of methylene chloride 100 parts Example 29 A subbing layer of the following composition was coated on an electroformed nickel plate with a thickness of 0.1+ nm. The coating solution, the charge generation layer coating solution, the charge transport layer coating solution, and the protective layer coating solution were sequentially applied and dried to a thickness of 0.3 μm each.
An electrophotographic photoreceptor of the present invention was prepared by forming a subbing layer, a charge generation layer of 0.2 .mu.m, a charge transport layer of 18 .mu.m, and a protective layer of 3 ptn.

[Subbing layer coating liquid]

Polysulfone (cyclohexanonetetrahydrofuran manufactured by Nissan Chemical ■ [charge transport layer coating liquid] charge transport substance P-1700 with the following structural formula) 400 parts 200 parts water
100 parts methanol
100 parts [Charge generating M coating liquid] Charge generating substance having the following structural formula 10 parts Methylene chloride [Protective layer coating liquid] 81 parts Electron accepting substance having the following structural formula 3 parts Tin oxide Toluene 2-butanone Example 30 80 170 parts 100 parts On the same support as in Example 25, a subbing layer coating liquid, a charge transport layer coating liquid, and a charge generation layer coating liquid having the following compositions were sequentially coated and dried to form a 2 μm thick layer each. An attracting layer, a charge transport layer of 22 μm and a charge generation layer of 0°4 were formed.

An electrophotographic photoreceptor of the present invention was prepared.

[Subbing layer coating liquid]

Titanium dioxide 10 parts [Charge generation layer coating liquid] Charge generating substance having the following structural formula Electron accepting substance having the following structural formula 30 parts 10 parts 2-butanone ethyl acetate [Charge transport J ~ Coating liquid] Charge having the following structural formula Transport substance Methylene chloride 1,2-Dichloroethane 70 parts 70 parts 8 parts 45 parts 50 parts Toluylene-2,4-diisocyanate 1 part Tetrahydrofuran 500 parts 4-Methyl-2-pentanone 300 parts Example 31 Same support as Example 28 A charge transport layer coating liquid, a charge generation layer coating liquid, an intermediate layer coating liquid, and a protective layer coating liquid having the following compositions were sequentially applied and dried on the top to form a charge transport layer of 20 μl and a charge transport layer of 0.2 μl each. Form a wrinkled charge generation layer, a 0.2 μl intermediate J- and a 5 μm protective layer.

A child photographic photoreceptor was created.

[Charge transport layer coating liquid]

Charge transport substance C11 of the following structural formula - Electrocyclohexanone of the present invention 10 parts 4-methyl-2-pentanone [intermediate layer coating solution] Methanol n-butanol [protective layer coating solution] 80 parts 20 parts 70 parts 40 parts Chloride Methylene [Charge generating layer coating liquid] Charge generating substance with the following structural formula Electron accepting substance with the following structural formula 200 parts 3 parts 1 part Conductive titanium oxide 90 parts Toluene 220 parts n-butanol 60 parts Example 32 Thickness 0 A charge transport layer coating solution, a charge generation layer coating solution, and a protective layer coating solution having the following compositions were sequentially applied and dried on a No. 2 nichrome plate to form a charge transport layer of 19 tones each.

A charge generation layer of 0.3 μm and a protective layer of 2pI11 were formed to produce an electrophotographic photoreceptor of the present invention.

[Charge transport R1 coating liquid] Charge transport substance having the following structural formula: 12 parts Toluylene-2,4-sicyclohexanone 2-butanone [Protective layer coating liquid] Socyanate 1 part 300 parts 100 parts Tetrahydrofuran [Charge generation layer coating Liquid] Charge-generating substance with the following structural formula Electron-accepting substance with the following structural formula (Kansui Kajiko Kuri ■ Saki Eslec BM-3) 80 parts 12 parts 6 parts Oxidation '8 90 parts Toluene 250 parts 2-butanone 70 parts Comparative example 25
~32 In the photoconductors of Examples 25 to 32 prepared as described above, photoconductors were formed in the same manner as in Examples 25 to 32 except that each charge generation layer did not contain an electron-accepting substance, and a comparison was made. Photoreceptors of Examples 25 to 32 were prepared.

The characteristics of each photoreceptor above were measured using a static 'f+L copy paper tester (
The evaluation was made as follows using a new model 5P-428 manufactured by Kawaguchi Electric.

First, corona charging was performed for 15 seconds at a discharge pressure of -6.0 V (or +6.0 irradiated with tungsten light.

The surface potential v at 1 second and 15 seconds after the start of charging at this time,
(v), V, ... (V) Also, during light irradiation, the exposure amount E1/2 (Qux-see) required for the surface potential to become -400 V or +400 V) was measured.

Further, this photoreceptor was irradiated with 30,000 Qux-8ec of tungsten light with a color temperature of 2,856° to cause optical fatigue, and then the vl, VIS, and E1/2 were set to 81 in the same manner as above.
It was fixed at 11.

The evaluation results are shown in Table-4.

Table-4 *00V Not charged and unmeasurable [Effects of the invention] The laminated organic electrophotographic photoreceptor with high sensitivity of the present invention has the following characteristics:
It is possible to prevent a delay in the rise of the charged potential after repeated use.

Therefore, according to the present invention, it is possible to obtain a good image without background stains when the image density decreases, the image density becomes uneven, the image is fogged, or the image is reversed in a copying machine, a printer, etc.

[Brief explanation of the drawing]

1 to 4 are schematic cross-sectional views of electrophotographic photoreceptors according to the present invention. Figure 2 Figure 3 Figure 4

Claims (1)

[Claims] (1) In a laminated organic electrophotographic photoreceptor having at least a charge generation layer and a charge transport layer on a conductive support, electrons represented by the following general formulas (I) to (IV) are present in the charge generation layer. An electrophotographic photoreceptor comprising at least one receptor compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and m and n represent integers from 0 to 4.) ▲Mathematical formulas, chemical formulas, tables, etc. ▼(II) (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and p, q, m, and n represent integers from 0 to 4.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and m and n represent integers from 0 to 4.) ▲There are numerical formulas, chemical formulas, tables, etc.▼(IV) (In the formula, R represents an alkyl group, an alkoxy group, or a halogen atom, and m and n represent integers of 0 to 4.)