JPH0943879A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a photoreceptor having high sensitivity and high stability at the time of repetitive use by using an electric charge generating material contg. a specified compd. and an electric charge transferring material contg. a specified compd. SOLUTION: This electrophotographic photoreceptor contains an electric charge generating material contg. a reactional product of an oxytitanium phthalocyanine compd. with (2R,3R)-2,3-butanediol and/or (2S,3S)-2,3-butanediol and an electric charge transferring material contg. one or more kinds of compds. selected from among hydrazone compds. represented by formulae I, II, wherein (n) is 0 or 1, Ar is an arom. cyclic group or a heterocyclic group, each of R<1> -R<3> is H, halogen, alkyl, etc., or a heterocyclic group, each of R<4> and R<5> is H, alkyl, etc., or a heterocyclic group, each of R<6> -R<10> is H, halogen, alkyl, etc., or a heterocyclic group and Z is a group of atoms required to form a hetero ring in combination with the benzene ring and N.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photoconductor for electrophotography used in copying machines, LD printers, LED printers and the like.

[0002]

2. Description of the Related Art In recent years, with the increasing demand for higher sensitivity and higher durability for electrophotographic photoreceptors, a function in which the charge generating function and the charge transporting function of the electrophotographic photoreceptor are shared by different materials. Development of a separation type electrophotographic photoconductor has been active.

In addition, semiconductor lasers (LDs) and light emitting diodes (LEDs) have been developed along with the development of the electronics industry.
Phthalocyanine compounds sensitive to these light sources have been attracting attention as materials used for electrophotographic photoreceptors such as copying machines, LD printers, LED printers, etc., which use a long-wavelength light source near 00 nm.

Among these, the phthalocyanine compound having titanium as a central metal has attracted attention as a material capable of increasing the sensitivity, and various researches and developments such as searching for various crystal forms and synthesizing derivatives have been actively conducted.

An electrophotographic photosensitive member using a titanium-based phthalocyanine compound is disclosed in, for example, JP-A-61-109.
Japanese Laid-Open Patent Publication No. 056 discloses an electrophotographic photoreceptor in which a charge transport layer containing a hydrazone compound and a binder polymer is laminated on a charge generating layer containing a titanium phthalocyanine compound and a binder polymer. .

Further, JP-A-5-273774 discloses an electrophotographic photoreceptor having a photosensitive layer containing a titanyl phthalocyanine crystal which is an adduct with an acyclic organic compound having an adjacent hydroxyl group and having 5 to 10 carbon atoms. Is disclosed.

However, even these electrophotographic photoreceptors cannot be said to be necessarily satisfactory because of insufficient points such as sensitivity and stability upon repeated use, and further improvement is required. .

Further, in the function-separated type electrophotographic photoreceptor, it is generally known that a combination of a specific charge-transporting material and a specific charge-generating material is effective in terms of sensitivity, stability, durability and the like. However, the charge-transporting material that was effective in combination with a specific charge-generating material does not always provide an electrophotographic photoreceptor that exhibits excellent characteristics in combination with another charge-generating material. If the combination of the charge-generating material and the charge-transporting material is inappropriate, not only the functions of the charge-generating material and the charge-transporting material cannot be fully exerted, but also the performance as an electrophotographic photoreceptor is deteriorated. However, the universal law in selecting the combination of the charge generating material and the charge transporting material is not always clear, and it has been difficult to find a combination of the specific charge transporting materials effective for the specific charge generating material.

[0009]

The problem to be solved by the present invention is that it has a high sensitivity to a long-wavelength light source near 700 nm, and has a semiconductor laser (LD) or a light emitting diode (LED).
It is an object of the present invention to provide an electrophotographic photosensitive member which can be used in an electrophotographic printer or a copying machine using a light source as a light source and has high sensitivity and high stability during repeated use.

[0010]

DISCLOSURE OF THE INVENTION The inventors of the present invention have made extensive studies in view of the above-mentioned circumstances, and as a result, have been found that an electrophotographic photosensitive member provided with a photosensitive layer containing a specific charge generating material and a specific charge transporting material. They have found that the body exhibits excellent sensitivity and potential stability, and have completed the present invention.

That is, to solve the above-mentioned problems, the present invention provides an electrophotographic photoreceptor having a photosensitive layer comprising a charge-generating material and a charge-transporting material on a conductive substrate.
The charge generation material is a reaction product of an oxytitanium phthalocyanine compound and (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol (hereinafter referred to as phthalocyanine used in the present invention. Reaction product), and the charge transport material is represented by the general formula (1)

[0012]

[Chemical 7]

(In the formula, n represents 0 or 1, Ar represents an aromatic ring group or a heterocyclic group. R ¹ , R ² and R ³ are each independently a hydrogen atom, a halogen atom, an alkyl group, And R ⁴ and R ⁵ each independently represent a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a heterocyclic group, and an aryl group, an aralkyl group or a heterocyclic group. May have a substituent) and a hydrazone compound represented by the general formula (2)

[0014]

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(In the formula, n represents 0 or 1, Ar represents an aromatic ring group or a heterocyclic group. R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom or halogen. Represents an atom, an alkyl group, an aryl group, an aralkyl group or a heterocyclic group, Z is a group of atoms necessary for forming a heterocyclic ring with a nitrogen atom and a benzene ring, and these groups have a substituent The present invention provides an electrophotographic photoconductor characterized by containing at least one compound selected from the group consisting of hydrazone compounds represented by the formula (1).

The method for producing the phthalocyanine reaction product used in the present invention is not particularly limited. For example, (1) an oxytitanium phthalocyanine compound and an optically active (2R, 3R) -2,3-butane are used. Production method by reaction with diol and / or (2S, 3S) -2,3-butanediol, (2) dihalotitanium phthalocyanine compound such as dichlorotitanium phthalocyanine and optically active (2R, 3R) -2,3- Production method by reaction with butanediol and / or (2S, 3S) -2,3-butanediol, (3) optically active (2R, 3R)-
2,3-butanediol and / or (2S, 3S)-
A production method by a coupling reaction between a titanium salt such as titanium tetrachloride and an orthophthalonitrile derivative in the presence of 2,3-butanediol, and the like, and the like.
The reaction product obtained by any of the production methods can be used.

Among these production methods, an oxytitanium phthalocyanine compound and an optically active (2R, 3R)-
2,3-butanediol and / or (2S, 3S)-
The reaction with 2,3-butanediol is preferable because the operation is simple.

The phthalocyanine reaction product used in the present invention is obtained by the above production method, and its structure is represented by the formula (7).

[0019]

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Or equation (8)

[0021]

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It is presumed that it is in a crystalline state containing a phthalocyanine reaction product having a specific isomer structure represented by:

The phthalocyanine reaction product used in the present invention is preferably in a crystalline state, and Cu--Kα is particularly preferable.
In the X-ray diffraction spectrum for, the crystalline state having a main peak at 9.5 ° of Bragg angle (2θ ± 0.2 °), or 8.3 °, 24.7 °, 2
More preferably, it is in a crystalline state having a peak at 5.1 °.

The electrophotographic photoreceptor of the present invention has a photosensitive layer comprising a charge generating material containing the above-mentioned crystals of the phthalocyanine reaction product used in the present invention.
In the X-ray diffraction spectrum for Cu-Kα of the photosensitive layer, the photosensitive layer having a main peak at a Bragg angle (2θ ± 0.2 °) of 9.5 °, 8.3 °, 24.7 °, 2
A photosensitive layer having a peak at 5.1 ° and a photosensitive layer having a main peak at 8.3 ° are preferable, and particularly, the Bragg angle (2θ).
A photosensitive layer having a main peak at 8.3 ° of ± 0.2 °) is more preferable.

An oxytitanium phthalocyanine compound and an optically active (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butane for obtaining a phthalocyanine reaction product used in the present invention. The reaction with the diol is preferably carried out under heating conditions, and the reaction temperature is preferably in the range of 30 to 300 ° C, and 50 to 250 ° C.
Is particularly preferred.

The oxytitanium phthalocyanine compound used as a raw material for synthesizing the phthalocyanine reaction product used in the present invention contains oxytitanium at the center of the phthalocyanine skeleton which may have a substituent, as long as the effect of the present invention is not impaired. Any crystal type may be used as long as it has, and may be a crystal type such as α type, β type, α, β mixed type, γ type, Y type, and amorphous type as long as the effect of the present invention is not impaired. When the phthalocyanine skeleton has a substituent, the substituent includes a lower alkyl group such as a methyl group and an ethyl group; an alkoxy group such as a methoxy group; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; and a nitro group. Can be mentioned. The number of these substituents can range from 1 to 16,
Combinations of one or more substituents are also possible.

The molar ratio of the reaction between the oxytitanium phthalocyanine compound and the optically active (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol is oxytitanium. Optically active (2R, 3R) -2, per mol of the phthalocyanine compound,
3-butanediol and / or (2S, 3S) -2,3
-Butanediol is preferably 0.25 mol or more,
The range of 5 to 1.5 mol is more preferable.

The (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol used as the starting material for synthesizing the phthalocyanine reaction product used in the present invention is optically active. , (2R, 3R) -2,3-butanediol or (2S, 3S) -2,3-butanediol, or an optically active threo-type 2,3-butanediol having different contents of both Is preferably used.

As the charge generating material for the electrophotographic photoreceptor of the present invention, one optical isomer of the phthalocyanine reaction product used in the present invention may be used alone, or two or more thereof may be mixed and used. You may use. That is, a reaction product of an oxytitanium phthalocyanine compound and (2R, 3R) -2,3-butanediol and a reaction product of an oxytitanium phthalocyanine compound and (2S, 3S) -2,3-butanediol are prepared. You may mix and use it.

For the reaction of the oxytitanium phthalocyanine compound with (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol, various known and commonly used compounds can be used, if necessary. These organic solvents can be used together. Examples of the organic solvent include aromatic organic solvents such as benzene, nitrobenzene, dichlorobenzene, trichlorobenzene, and α-chloronaphthalene; ketone organic solvents such as cyclohexanone, methyl ethyl ketone, and methyl isobutyl ketone; tetrahydrofuran, dimethyl cellosolve. Ether-based organic solvents such as; Butyl ester, butyl lactate and other ester-based organic solvents; Dimethylformamide, dimethylsulfoxide and other aprotic polar organic solvents; Trichloroethane and other halogen-based organic solvents; Amyl alcohol, dodecanol, etc. Examples thereof include alcoholic organic solvents. These solvents may be used alone or in combination of two or more.

After synthesizing the phthalocyanine reaction product used in the present invention, it may be purified if necessary.

As described above, in the synthesis of the phthalocyanine reaction product used in the present invention, the respective production conditions such as reaction molar ratio, reaction temperature, reaction time, solvent, catalyst, purification method, crystallization method, etc. are appropriately selected. Can be adopted.

In the present invention, the charge generating material used in the electrophotographic photoreceptor contains the phthalocyanine reaction product used in the present invention as an essential component, but other known charge generating materials may be used in combination if necessary. It is also possible.

Other charge generating materials that can be used in combination include, for example, metal-free phthalocyanine compounds and various metal phthalocyanine compounds, for example, α type, β type, α, β mixed type, and γ.
Examples thereof include crystalline type or amorphous type oxytitanium phthalocyanine compounds such as type and Y type. Further, charge generating materials other than phthalocyanine, for example, 1) azo pigments such as monoazo pigments, disazo pigments and trisazo pigments,
2) Various metal phthalocyanines, metal-free phthalocyanines,
Phthalocyanine pigments such as naphthalocyanine, 3) condensed polycyclic pigments such as perinone pigments, perylene pigments, anthraquinone pigments, quinacridone pigments, indigo pigments and thioindigo pigments, 4) squalium pigments, 5) azulene pigments, 6) pyrylium pigments Pyrylium salt dyes such as salts and thiapyrylium salts, 7) cyanine dyes, 8) triphenylmethane dyes, 9) selenium, selenium tellurium, selenium
Selenium compounds such as arsenic, zinc oxide, cadmium sulfide,
Inorganic materials such as cadmium selenide and amorphous silicon can be used together. Any other material that absorbs light and efficiently generates charge carriers can be used. The charge generating materials that can be used in combination are not limited to those described here, and may be used alone or in combination of two or more when used.

The specific charge transporting material used in the electrophotographic photoreceptor of the present invention is selected from the group consisting of the hydrazone compound represented by the general formula (1) and the hydrazone compound represented by the general formula (2). At least one compound is used. Representative examples are shown below by structural formulas, but the present invention is not necessarily limited to these examples.

In the structural formulas below, Me is a methyl group, Et is an ethyl group, n-Pr is an n-propyl group, and B is
zl is a benzyl group, Ph is a phenyl group, and p-Tol is p.
Represents a tolyl group, and the number below the structural formula is the compound No.
Represents

[0037]

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[0038]

[Chemical 12]

[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

[Chemical 21]

[0048]

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[0049]

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[0050]

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[0051]

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[0052]

[Chemical formula 26]

[0053]

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[0054]

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[0055]

[Chemical 29]

[0056]

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[0057]

[Chemical 31]

[0058]

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[0059]

[Chemical 33]

The electrophotographic photoreceptor of the present invention can have various structures. Examples thereof are shown in FIGS. 1 to 5.

The electrophotographic photoreceptor of FIGS. 1 and 2 has a charge generation layer 2 mainly composed of a charge generation material on a conductive substrate 1.
And a charge-transporting material 3 and a charge-transporting layer 3 made of a binder resin as necessary for forming the photosensitive layer.

The electrophotographic photosensitive member of FIG. 3 has a conductive substrate 1
A photosensitive layer in which the charge generating material 7 and the charge transporting material 8 are dissolved or dispersed in a binder resin is provided thereon.

The electrophotographic photoconductor of FIG. 4 is designed for the purpose of protecting the conductive substrate, improving the adhesiveness, improving the coating property, controlling the charge injection amount from the conductive substrate to the photosensitive layer, and the like. The intermediate layer 5 is provided between the electroconductive substrate 1 and the charge generation layer 2 of the electrophotographic photosensitive member 1.

The electrophotographic photoconductor of FIG. 5 further has a surface protective layer 6 on the surface of the electrophotographic photoconductor of FIG. 1 in order to protect the electrophotographic photoconductor from physical or chemical external factors. Is provided.

The intermediate layer and the surface protective layer shown in the electrophotographic photoconductors of FIGS. 4 and 5 can be provided to the electrophotographic photoconductors other than those shown in FIG. 1 if necessary.

In the case of the electrophotographic photoconductors shown in FIGS. 1, 2, 4 and 5, the charge generating material contained in the charge generating layer 2 generates charges, while the charge transporting layer 3 generates charges. Receive the injection and carry out the transportation. That is, the charge required for light attenuation is generated in the charge generating material, and the charge is transported in the charge transport medium. In the electrophotographic photosensitive member of FIG. 3, the charge generating material generates an electric charge with respect to light, and the charge transfer material and the binder resin cause the electric charge to move.

The electrophotographic photoreceptor of FIG. 1 is dispersed on the charge generation layer formed of a vapor deposition film of the charge generation material, or fine particles of the charge generation material are dispersed in a solvent in which a binder resin is dissolved, if necessary. The charge-transporting material alone is applied onto the charge-generating layer obtained by applying the dispersion obtained above and then drying.
Alternatively, it can be manufactured by providing a charge transport layer obtained by applying a solution in which a binder resin is used in combination and dissolving it, if necessary, and then drying.

The electrophotographic photoreceptor of FIG. 2 is obtained by applying a solution prepared by dissolving a charge transport material alone or, if necessary, a binder resin together, onto a conductive substrate and then drying. On the charge transport layer, a charge generation layer composed of a vapor-deposited film of the charge generation material or a dispersion obtained by dispersing fine particles of the charge generation material in a solvent or a binder resin solution is applied and then dried. It can be manufactured by providing a charge generation layer obtained by.

In the electrophotographic photoreceptor of FIG. 3, fine particles of the charge generating material are dispersed in a solution in which the charge transporting material is used alone or, if necessary, a binder resin is also used in combination to dissolve the charge transporting material. It can be produced by providing a photosensitive layer obtained by applying the composition on a substrate and then drying it.

In the case of the electrophotographic photoreceptors of FIGS. 1, 2, 4 and 5, the thickness of the charge generation layer is preferably 5 μm or less, particularly preferably in the range of 0.01 to 2 μm, and the thickness of the charge transport layer is preferably. The thickness is preferably in the range of 3 to 50 μm, 5 to 30 μm
The range of m is particularly preferred. In the case of the electrophotographic photoreceptor of FIG. 3, the thickness of the photosensitive layer is preferably in the range of 3 to 50 μm,
A range of 5 to 30 μm is particularly preferred. The thickness of the intermediate layer in the electrophotographic photoreceptor of FIG. 4 is preferably 5 μm or less, and particularly preferably in the range of 0.1 to 1 μm. The thickness of the surface protective layer in the electrophotographic photoreceptor of FIG. 5 is 2 μm.
The following is preferable, and the range of 0.01 to 1 μm is particularly preferable.

The ratio of the charge transport material in the charge transport layer in the electrophotographic photoreceptor of FIGS. 1, 2, 4 and 5 is 5
Is preferably in the range of 100 to 100% by weight, particularly preferably in the range of 40 to 80% by weight. Further, the proportion of the charge generating material in the charge generating layer is preferably in the range of 5 to 100% by weight, and 40
A range of ˜80% by weight is particularly preferred. The ratio of the charge transport material in the photosensitive layer of the electrophotographic photoreceptor of FIG.
The range of 99% by weight is preferable, and the ratio of the charge generating material is
A range of 1 to 50% by weight is preferable, and a range of 3 to 20% by weight is particularly preferable.

A plasticizer and a sensitizer can be used together with the binder resin in the production of any of the electrophotographic photoreceptors shown in FIGS.

In the electrophotographic photoreceptor of the present invention, as the charge transport material, at least one compound of the hydrazone compounds represented by the general formula (1) or (2) is used. Other known charge transport materials may be used together.

Examples of the charge transport material of a low molecular weight compound which can be used in combination include, for example, 1) carbazols such as N-ethylcarbazol, N-isopropylcarbazol and N-phenylcarbazol; 2) N-methyl-N-phenylhydrazino-3-methylidene-9-ethylcarbazol,
N, N-diphenylhydrazino-3-methylidene-9-
Ethylcarbazol, p- (N, N-dimethylamino)
Benzaldehyde diphenylhydrazone, p- (N, N
-Diethylamino) benzaldehyde diphenylhydrazone, p- (N, N-diphenylamino) benzaldehyde diphenylhydrazone, 1- [4- (N, N-diphenylamino) benzylideneimino] -2,3-dimethylindoline, N-ethylcarbazol -3-Methylidene-N-aminoindoline, N-ethylcarbazol-
Hydrazones such as 3-methylidene-N-aminotetrahydroquinoline; 3) Oxadiazoles such as 2,5-bis (p-diethylaminophenyl) -1,3,4-oxadiazole; 4) 1-phenyl- 3- (p-diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazoline, 1- [quinolyl- (2)]-3- (p
-Pyrazolines such as diethylaminophenyl) pyrazolin; 5) tri-p-tolylamine, N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1 '.
-Arylamines such as biphenyl-4,4'-diamine; 6) 1,1-bis (p-diethylaminophenyl)
Butadienes such as -4,4-diphenyl-1,3-butadiene; 7) 4- (2,2-diphenylethenyl)-
N, N-diphenylbenzenamine, 4- (1,2,2)
Examples thereof include styryls such as -triphenylethenyl) -N, N-diphenylbenzenamine.

Examples of the charge transporting material of the polymer compound which can be used in combination include poly-N-vinylcarbazol, halogenated poly-N-vinylcarbazol, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, and the like.
Examples thereof include poly-9-vinylphenylanthracene, pyrene-formamide resin, ethylcarbazole-formaldehyde resin, triphenylmethane polymer, and polyphenylalkylsilane.

The charge transport materials that can be used in combination are not limited to those described here, and may be used alone or in combination of two or more when used.

When these charge transporting materials are used in combination, the content of the hydrazone compound represented by the general formula (1) and the hydrazone compound represented by the general formula (2) in the total charge transporting material is 20% by weight. The above is preferable, and 50% or more is particularly preferable.

Any known sensitizer can be used as the sensitizer which is optionally used in the photosensitive layer.

Examples of the sensitizer include chloranil, tetracyanoethylene, methyl violet, rhodamine B, cyanine dye, merocyanine dye, pyrylium dye and thiapyrylium dye.

Further, in the electrophotographic photoreceptor of the present invention, in order to improve storage stability, durability and environmental resistance, if necessary, an antioxidant, an ultraviolet absorber and a light stabilizer are added in the photosensitive layer. A deterioration preventing agent such as an agent may be contained. Examples of these substances include a phenol compound, a hydroquinone compound, and an amine compound.

As the binder resin for dissolving the charge transporting material of the present invention, various kinds can be mentioned, but it is preferable to use a hydrophobic and electrically insulating film-forming polymer compound. As such a high-molecular polymer, for example,
Polycarbonate resin, polyester resin, methacrylic resin, acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyarylate resin, polystyrene resin, polyvinyl acetate resin, polyvinyl butyral resin, diallyl phthalate Resin, styrene-butadiene copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone-alkyd resin, phenolic resin, epoxy resin, styrene-alkyd resin, poly-N-vinylcarbazole Resin, urea resin, polysulfone resin and the like can be mentioned.

Of these binder resins, polycarbonate and polyarylate are preferable because they form a photosensitive layer having high durability, and are particularly preferably those represented by the general formula (3).

[0083]

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(In the formula, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and R ¹¹ and R ¹² each independently represent a hydrogen atom, an alkyl group or an aromatic group. , These groups may have a substituent), a polycarbonate having a repeating unit represented by the general formula (4)

[0085]

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(In the formulae, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and W represents a group of atoms necessary for forming a carbocycle and a heterocycle. May have a substituent), a polycarbonate having a repeating unit represented by the general formula (3), a repeating unit represented by the general formula (3) and a general formula (5).

[0087]

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(Wherein, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and these groups may have a substituent). Polymerized polycarbonate and general formula (6)

[0089]

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(Wherein the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and these groups may have a substituent). Arylate is more preferable as a resin that dissolves the charge transport material of the present invention because it has high electrical stability.

The binder resin is not limited to the ones described here, and may be used alone or in combination with the binder resin.
You may use it as a mixture of 2 or more types.

Further, in order to improve the film-forming property, flexibility and mechanical strength of the electrophotographic photoreceptor, well-known additives such as a plasticizer and a surface modifier are added together with these binder resins. It can also be used.

Examples of the plasticizer include biphenyl, biphenyl chloride, o-ta-phenyl, p-ta-phenyl,
Dibutyl phthalate, diethyl glycol phthalate,
Dioctyl phthalate, triphenyl phosphoric acid, dimethylnaphthalene, benzophenone, chlorinated paraffin, polypropylene, polystyrene, various fluorohydrocarbons and the like can be mentioned.

Examples of the surface modifier include silicon oil and fluorine resin. In addition, as the material that can be used when the intermediate layer is provided in the electrophotographic photoreceptor of the present invention, in addition to the polymer compound used for the binder resin, casein, gelatin, ethyl cellulose, nitrocellulose , Carboxy-methylcellulose
Polymer, vinylidene chloride-based polymer latex, styrene-
Butadiene-based polymer latex, polyvinyl alcohol
And polyamide, polyurethane, phenol resin, aluminum oxide, tin oxide, titanium oxide and the like.

Materials that can be used when the surface protective layer layer is provided in the electrophotographic photoreceptor of the present invention include, in addition to the polymer compound used for the binder resin,
Casein, gelatin, ethyl cellulose, nitrocellulose, carboxy-methyl cellulose, vinylidene chloride polymer latex, styrene-butadiene polymer latex, polyvinyl alcohol, polyamide, polyurethane, phenol resin, aluminum oxide, Examples thereof include tin oxide and titanium oxide.

When the laminated type electrophotographic photoreceptor is formed by coating, the solvent for dissolving the binder resin varies depending on the kind of the binder resin, but it is desirable to select from those which do not dissolve the lower layer. . Specific examples of the organic solvent include alcohols such as methanol, ethanol and n-propanol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; N, N-dimethylformamide and N. , Amides such as N-dimethylacetamide; ethers such as tetrahydrofuran, dioxane and methyl cellosolve; esters such as methyl acetate and ethyl acetate; sulfoxides and sulfones such as dimethyl sulfoxide and sulfolane; dichloromethane, chloroform, tetrachloride Aliphatic halogenated hydrocarbons such as carbon and trichloroethane; aromatics such as benzene, toluene, xylene, monochlorobenzene, and dichlorobenzene.

Examples of the conductive substrate used in the electrophotographic photoreceptor of the present invention are 1) metals such as aluminum, copper, zinc, stainless steel, chromium, titanium, nickel, molybdenum, vanadium, indium, gold and platinum. Or alloy, 2) conductive compound such as conductive polymer, indium oxide and tin oxide, or 3) metal, alloy such as aluminum, palladium, rhodium, gold and platinum, coating, vapor deposition, laminating, etc. Examples include glass, paper, plastic film, and ceramics that have been subjected to the above treatment. Further, the surface of these conductive substrates may be subjected to chemical or physical treatment, if necessary.

The shape of the electrophotographic photosensitive member of the present invention varies depending on the shape of the conductive substrate used, but various shapes such as a drum shape, a flat plate shape, a sheet shape, and a belt shape are possible.

Various methods can be used for forming the photosensitive layer, and examples of the coating method include a dip coating method, a spray coating method, a spinner coating method and a bead coating method. A coating method such as a coating method, a curtain coating method, a wire bar coating method, a blade coating method and a roller coating method can be used.

[0100]

EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples, "part" means "part by weight".

<Synthesis Example 1> An oxytitanium phthalocyanine compound obtained by a reaction between titanium tetrachloride and o-phthalonitrile, which is an oxytitanium phthalocyanine compound showing a powder X-ray diffraction spectrum by CuKα line shown in FIG. 20 parts, (2R, 3R) -2,
1. While stirring 4.4 parts of 3-butanediol and 240 parts of α-chloronaphthalene at 195 to 205 ° C.
The reaction was performed for 5 hours.

After cooling the reaction mixture to room temperature, it was filtered off, the residue was washed with benzene, methanol, dimethylformamide (hereinafter abbreviated as DMF) and water in this order, and then dried under reduced pressure. A phthalocyanine reaction product was obtained.

This reaction product showed a peak at m / Z = 648 in the mass spectrum. The result of measurement of powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 7. Further, the results of elemental analysis of this reaction product are shown in Table 1.

[0104]

[Table 1]

<Example 1> 2 parts of the phthalocyanine reaction product obtained in Synthesis Example 1 and 2 parts of butyral resin ("S-REC BH-3" manufactured by Sekisui Chemical Co., Ltd.) were mixed with 6 parts of methylene chloride.
Add to a mixed solvent consisting of 6 parts and 99 parts of 1,1,2-trichloroethane and disperse with a paint conditioner,
A charge generating material dispersion liquid was obtained by mixing.

FIG. 8 shows the X-ray diffraction spectrum of a thin film having a thickness of 5 μm obtained by dip coating the dispersion liquid of the charge generating material thus obtained on a thin metal plate.

Next, the charge generation material dispersion thus obtained was applied onto a polyester film on which aluminum was vapor-deposited using a wire bar so that the film thickness after drying would be 0.3 μm, and then dried. To form a charge generation layer.

On the charge generation layer, 8 parts of the charge transport material of Exemplified Compound No. 183 described above and the following structural formula (9)

[0109]

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Polycarbonate having a repeating unit represented by "(Iupilon Z20 manufactured by Mitsubishi Gas Chemical Co., Inc.
0 ") 10 parts were dissolved in a mixed solvent consisting of 54 parts of methylene chloride and 36 parts of chlorobenzene to be applied with a wire bar so that the film thickness after drying was 20 μm, and then dried. A charge transport layer was formed to obtain an electrophotographic photoreceptor having the layer structure shown in FIG.

<Synthesis Example 2> In Synthesis Example 1, (2R,
Instead of 3R) -2,3-butanediol, (2S, 3
A phthalocyanine reaction product was obtained in the same manner as in Synthesis Example 1 except that S) -2,3-butanediol was used.

This reaction product showed a peak at m / Z = 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 9.

<Example 2> Synthesis Example 1 in Example 1
An electrophotographic photoconductor was obtained in the same manner as in Example 1 except that the phthalocyanine reaction product obtained in Synthesis Example 2 was used instead of the phthalocyanine reaction product obtained in.

<Example 3> Synthesis Example 1 in Example 1
The same procedure as in Example 1 was repeated except that 1 part of the phthalocyanine reaction product obtained in Synthesis Example 1 and 1 part of the phthalocyanine reaction product obtained in Synthesis Example 2 were used instead of 2 parts of the phthalocyanine reaction product obtained in 1. To obtain an electrophotographic photoreceptor.

<Synthesis Example 3> In Synthesis Example 1, (2R,
3R) -2,3-butanediol instead of 4.4 parts,
A phthalocyanine reaction product was obtained in the same manner as in Synthesis Example 1 except that 2.2 parts of (2R, 3R) -2,3-butanediol was used.

This reaction product showed peaks at m / Z = 576 and 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 10.

<Example 4> Synthesis example 1 in Example 1
An electrophotographic photoconductor was obtained in the same manner as in Example 1, except that the phthalocyanine reaction product obtained in Synthesis Example 3 was used in place of the phthalocyanine reaction product obtained in 1.

Also, the X-ray diffraction spectrum of the thin film obtained by dip-coating the dispersion liquid of the charge generating material used in Example 4 on a thin metal plate so that the film thickness after drying was 5 μm, was obtained. 11 shows.

<Synthesis Example 4> An oxytitanium phthalocyanine compound obtained by subjecting oxytitanium phthalocyanine obtained from titanium tetraisopropoxide and 1,3-diiminoisoindoline to acid paste treatment with concentrated sulfuric acid. 20 parts of oxytitanium phthalocyanine compound showing powder X-ray diffraction spectrum by CuKα ray shown in 12 and (2R, 3R) -2,3
-Butanediol (4.7 parts) was reacted in 240 parts of α-chloronaphthalene at 195 to 205 ° C under stirring for 1.5 hours.

After cooling the reaction mixture to room temperature, it was filtered off, and the residue was washed with benzene, methanol, DMF and water in this order and then dried under reduced pressure to obtain a phthalocyanine reaction product.

This reaction product showed peaks at m / Z = 576 and 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 13.

<Example 5> Synthesis example 1 in Example 1
An electrophotographic photoconductor was obtained in the same manner as in Example 1 except that the phthalocyanine reaction product obtained in Synthesis Example 4 was used in place of the phthalocyanine reaction product obtained in.

Further, the X-ray diffraction spectrum of the thin film obtained by dip-coating the dispersion liquid of the charge-generating material used in Example 5 on a thin metal plate so that the film thickness after drying was 5 μm, was obtained. Shown in 14.

Example 6 In Example 1, instead of the polycarbonate having the repeating unit represented by the structural formula (9), the structural formula (10) was used.

[0125]

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The repeating unit represented by and the structural formula (1
1)

[0127]

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A copolymerized polycarbonate having a repeating unit represented by the following formula in a ratio of 86:14 was used, and 2,6 parts together with 8 parts of the charge transport material of Exemplified Compound No. 183 described above were used.
An electrophotographic photoreceptor was obtained in the same manner as in Example 1 except that 1 part of -di-t-butyl-p-cresol was used.

<Example 7> In Example 1, the charge transport layer was formed using the charge transport material 8 of Exemplified Compound No. 183 described above.
Part, 2,6-di-t-butyl-p-cresol 1 part and structural formula (11)

[0130]

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Polycarbonate having a repeating unit represented by (“Panlite C140 manufactured by Teijin Chemicals Ltd.
0 ") 10 parts with 80 parts of methylene chloride and 1,1,2-
The same procedure as in Example 1 was carried out except that a coating solution dissolved in a mixed solution of 20 parts of trichloroethane was applied so that the film thickness after drying was 20 μm, and then dried to obtain a charge transport layer. A photoconductor for electrophotography was obtained.

<Example 8> In Example 1, the charge transport layer was formed by using the charge transport material 8 of Exemplified Compound No. 183 described above.
Part, 2,6-di-t-butyl-p-cresol 1 part and structural formula (12)

[0133]

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A coating solution prepared by dissolving 10 parts of a polyarylate having a repeating unit represented by (trade name "ISARYL25S" manufactured by ISONOVA) in 100 parts of 1,4-dioxane has a film thickness after drying of 20 μm. As described above, except that the charge transport layer is obtained by drying.
An electrophotographic photosensitive member was obtained in the same manner as in Example 1.

<Synthesis Example 5> In Synthesis Example 1, (2R,
3R) -2,3-butanediol instead of 4.4 parts,
A phthalocyanine reaction product was obtained in the same manner as in Synthesis Example 1 except that 3.1 parts of (2R, 3R) -2,3-butanediol was used.

The reaction product showed peaks at m / Z = 576 and 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG.

<Example 9> Synthesis Example 1 in Example 1
An electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the phthalocyanine reaction product obtained in Synthesis Example 5 was used in place of the phthalocyanine reaction product obtained in.

Further, the X-ray diffraction spectrum of the thin film obtained by dip-coating the dispersion liquid of the charge generating material used in Example 9 on a thin metal plate so that the film thickness after drying was 5 μm, was obtained. 16 shows.

<Example 10> In Example 1, instead of the phthalocyanine reaction product obtained in Synthesis Example 1, Synthesis Example 3 was used.
Using 2 parts of the phthalocyanine reaction product obtained in 1., instead of the polycarbonate having the repeating unit represented by the structural formula (9), a polycarbonate having the repeating unit represented by the structural formula (10) (manufactured by Teijin Chemicals Ltd. Trade name "Panlite C1400") is used, and 40 parts of methylene chloride and 1,1,2-trichloroethane 1 are used instead of the mixed solvent consisting of methylene chloride and chlorobenzene.
A mixed solvent composed of 0 parts was used, and further, 8 parts of the charge transport material of Exemplified Compound No. 183 described above was used for 2,6
An electrophotographic photoreceptor was obtained in the same manner as in Example 1 except that 1 part of -di-t-butyl-p-cresol was used.

<Comparative Synthesis Example 1> In Synthesis Example 1, (2
R, 3R) -2,3-butanediol instead of meso-
A phthalocyanine reaction product was obtained in the same manner as in Synthesis Example 1 except that 2,3-butanediol was used.

The reaction product showed a peak at m / Z = 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG.

Comparative Example 1 Synthesis Example 1 in Example 1
An electrophotographic photoreceptor was obtained in the same manner as in Example 1, except that the phthalocyanine reaction product obtained in Comparative Synthesis Example 1 was used in place of the phthalocyanine reaction product obtained in 1.

Further, the X-ray diffraction spectrum of the thin film obtained by dip-coating the dispersion liquid of the charge generation material used in Comparative Example 1 on a thin metal plate so that the film thickness after drying was 5 μm, was obtained. 18 shows.

<Comparative Synthesis Example 2> In Synthesis Example 1, (2
R, 3R) -2,3-butanediol was replaced with ethylene glycol in the same manner as in Synthesis Example 1, except that ethylene glycol was used.
A phthalocyanine reaction product was obtained.

The reaction product showed a peak at m / Z = 620 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 19.

<Comparative Example 2> Synthesis Example 1 in Example 1
An electrophotographic photoconductor was obtained in the same manner as in Example 1, except that the phthalocyanine reaction product obtained in Comparative Synthesis Example 2 was used in place of the phthalocyanine reaction product obtained in.

Further, the X-ray diffraction spectrum of the thin film obtained by dip-coating the dispersion liquid of the charge generation material used in Comparative Example 2 on a thin metal plate so that the film thickness after drying was 5 μm, was obtained. Shown in 20.

<Comparative Example 3> In Example 1, instead of the charge transporting material of Exemplified Compound No. 183 described above, the structural formula (13) was used.

[0149]

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An electrophotographic photoreceptor was obtained in the same manner as in Example 1 except that the charge transport material represented by

<Electrophotographic Characteristics> The electrophotographic photoconductors obtained in Examples 1 to 10 and Comparative Examples 1 to 3 were subjected to an electrostatic copying paper test apparatus (“SP428” manufactured by Kawaguchi Electric Co., Ltd.). The electrophotographic photosensitive member was charged in the dark by corona discharge of −6 KV, and the surface potential V ₀ (V) of the electrophotographic photosensitive member at this time was measured. Next, the surface potential V ₁₀ (V) of the electrophotographic photoreceptor when left as it is for 10 seconds in the dark.
Was measured. V ₀ and the potential retention of the surface potential of the electrophotographic photoreceptor than V ₁₀ (%): was calculated _{((V 10 / V 0)} × 100). Further, with respect to the surface potential V ₁₀ , a wavelength of 780 nm,
Exposure is performed with light having an exposure energy of 1 μW / cm ^{2, and} the exposure amount E is halved from the time until the surface potential becomes half of V _10.
1/2 (μJ / cm ² ) was determined. Furthermore, the surface potential 15 seconds after the start of exposure, that is, the residual potential V _R (V) was measured. Table 2 shows the measurement results of dark decay and light decay of the surface potential.
And shown in Table 3 collectively.

Also, the measurement results immediately after repeating the process of charging, leaving in the dark for 1 second, exposure for 1 second, and static elimination for 0.1 second by 300 lux of white light 500 times were the same.
And shown in Table 3 collectively.

[0153]

[Table 2]

[0154]

[Table 3]

<Examples 11 to 20> In Example 10, except that 10 parts of the charge transport materials shown in Tables 4 and 5 were used instead of 8 parts of the charge transport material of Exemplified Compound No. 183. An electrophotographic photoreceptor was obtained in the same manner as in Example 10.

Tables 4 and 5 show the electrophotographic characteristics of these electrophotographic photoconductors by the same methods as those evaluated in Examples 1 to 10.

[0157]

[Table 4]

[0158]

[Table 5]

Example 21 A resin solution was prepared by dissolving 1 part of a polyamide resin (“Amilan CM-8000” manufactured by Toray Industries, Inc.) in a mixed solvent consisting of 7 parts of methanol and 7 parts of n-butanol. This resin solution was applied by dip coating to the outer peripheral surface of an aluminum drum having a diameter of 30 mm and a wall thickness of 1 mm so that the film thickness after drying would be 1 μm, and then dried to form a barrier layer.

Next, 2 parts of the phthalocyanine reaction product obtained in Synthesis Example 3 and 2 parts of butyral resin (“S-REC BH-3” manufactured by Sekisui Chemical Co., Ltd.) were added to 66 parts of methylene chloride and 1,1,2-trichloroethane. It was added to 99 parts of the mixed solvent and dispersed and mixed with a paint conditioner to obtain a charge generating material dispersion liquid. The charge-generating material dispersion thus obtained is applied onto the barrier layer by dip coating,
After coating so that the film thickness after drying would be 0.4 μm, it was dried to provide a charge generation layer.

Next, 8 parts of the charge-transporting material of Exemplified Compound No. 183 described above, 1 part of 2,6-di-t-butyl-p-cresol and the repeating unit represented by the above structural formula (9) were used. 10 parts of the polycarbonate (trade name “UPILON Z200” manufactured by Mitsubishi Gas Chemical Co., Inc.) was dissolved in a mixed solvent of 54 parts of methylene chloride and 36 parts of chlorobenzene to obtain a charge transport layer forming coating material. The charge transport layer-forming coating material thus obtained is applied onto the charge generation layer by dip coating so that the film thickness after drying is 20 μm, and then dried to form the charge transport layer. A drum-shaped electrophotographic photosensitive member was obtained.

<Examples 22 to 24> Example 22 to 24 was carried out except that 10 parts of the charge transport material shown in Table 6 below was used instead of 8 parts of the charge transport material of Exemplified Compound No. 183. An electrophotographic photoreceptor was obtained in the same manner as in Example 21.

Comparative Example 4 The procedure of Example 21 was repeated except that 10 parts of the charge transport material represented by the structural formula (13) was used instead of 8 parts of the charge transport material of Exemplified Compound No. 183. An electrophotographic photoreceptor was obtained in the same manner as in Example 21.

<Image characteristics> The drum-shaped electrophotographic photoreceptors obtained in Examples 21 to 24 and Comparative Example 4 were mounted on a commercially available laser printer (trade name "Laser Jet 4" manufactured by Hewlett-Packard Co.), and toner was attached. Continuous printing was performed while replenishing, and the image condition was evaluated.

Table 6 shows a list of the evaluation results at the initial stage and after the printing test on 10,000 sheets.

[0166]

[Table 6]

[0167]

The electrophotographic photoreceptor of the present invention has a thickness of 700 nm.
It has a high sensitivity to long-wavelength light sources in the vicinity and maintains a high stability during repeated use, which is extremely effective in practice.

[Brief description of drawings]

FIG. 1 is a schematic cross-sectional view showing an example of a layer structure that can be taken by an electrophotographic photoreceptor of the present invention.

FIG. 2 is a schematic cross-sectional view showing an example of a layer structure that the electrophotographic photoreceptor of the present invention can have.

FIG. 3 is a schematic cross-sectional view showing an example of a layer structure that can be taken by the electrophotographic photoreceptor of the present invention.

FIG. 4 is a schematic cross-sectional view showing an example of a layer structure that the electrophotographic photoreceptor of the present invention can have.

FIG. 5 is a schematic cross-sectional view showing an example of a layer structure that can be taken by the electrophotographic photoreceptor of the present invention.

FIG. 6 is a powder X of an oxytitanium phthalocyanine compound used as a manufacturing raw material in Synthesis Example 1 by CuKα ray.
It is a line diffraction spectrum figure.

FIG. 7: C of the phthalocyanine reaction product obtained in Synthesis Example 1
It is a powder X-ray-diffraction spectrum figure by uK (alpha) ray.

FIG. 8 is an X-ray diffraction spectrum diagram of a thin film obtained by dip-coating a resin dispersion of the phthalocyanine reaction product produced in Example 1 on a thin metal plate.

FIG. 9: C of phthalocyanine reaction product obtained in Synthesis Example 2
It is a powder X-ray-diffraction spectrum figure by uK (alpha) ray.

10 is a powder X-ray diffraction spectrum diagram of a phthalocyanine reaction product obtained in Synthesis Example 3 by CuKα ray.

FIG. 11 is an X-ray diffraction spectrum diagram of a thin film obtained by dip-coating a resin dispersion of the phthalocyanine reaction product produced in Example 4 on a thin metal plate.

FIG. 12 is a powder X-ray diffraction spectrum diagram of a CuKα ray of an oxytitanium phthalocyanine compound used as a manufacturing raw material in Synthesis Example 4.

FIG. 13 is a powder X-ray diffraction spectrum diagram by a CuKα ray of a phthalocyanine reaction product obtained in Synthesis Example 4.

FIG. 14 is an X-ray diffraction spectrum diagram of a thin film obtained by dipping and coating a resin dispersion of the phthalocyanine reaction product produced in Example 5 on a thin metal plate.

FIG. 15 is a powder X-ray diffraction spectrum diagram by a CuKα ray of a phthalocyanine reaction product obtained in Synthesis Example 5.

16 is an X-ray diffraction spectrum diagram of a thin film obtained by dipping and coating a resin dispersion of the phthalocyanine reaction product prepared in Example 9 on a thin metal plate.

17 is a powder X-ray diffraction spectrum of a phthalocyanine reaction product obtained in Comparative Synthesis Example 1, using CuKα radiation.

FIG. 18 is an X-ray diffraction spectrum diagram of a thin film obtained by dipping and coating a resin dispersion of the phthalocyanine reaction product produced in Comparative Example 1 on a thin metal plate.

FIG. 19 is a powder X-ray diffraction spectrum of a phthalocyanine reaction product obtained in Comparative Synthesis Example 2 by CuKα ray.

FIG. 20: A resin dispersion of the phthalocyanine reaction product prepared in Comparative Example 2 was immersed in a thin metal plate.

[Explanation of symbols]

 1 Conductive Substrate 2 Charge Generation Layer 3 Charge Transport Layer 4 Charge Generation and Transport Layer 5 Intermediate Layer 6 Surface Protection Layer 7 Charge Generation Material 8 Charge Transport Material

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[Procedure amendment]

[Submission date] August 1, 1995

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0103

[Correction method] Change

[Correction contents]

This reaction product showed a peak at m / Z = 648 in the mass spectrum. The result of measuring the powder X-ray diffraction spectrum of this reaction product by CuKα ray is shown in FIG. 7. Further, the results of elemental analysis of this reaction product are shown in Table 1.

Claims (6)

[Claims] 1. An electrophotographic photoreceptor having a photosensitive layer formed by using a charge generating material and a charge transporting material on a conductive substrate, wherein the charge generating material is an oxytitanium phthalocyanine compound and (2R, 3R) -2, The charge transport material contains a reaction product with 3-butanediol and / or (2S, 3S) -2,3-butanediol, and has a general formula (1): (In the formula, n represents 0 or 1, Ar represents an aromatic ring group or a heterocyclic group. R ¹ , R ² and R ³ are each independently a hydrogen atom, a halogen atom, an alkyl group or an aryl group. Group, an aralkyl group or a heterocyclic group, R ⁴ and R ⁵ each independently represent a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a heterocyclic group. And a hydrazone compound represented by the general formula (2): (In the formula, n represents 0 or 1, Ar represents an aromatic ring group or a heterocyclic group. R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a halogen atom or an alkyl group. Group, ant
Represents an alkyl group, an aralkyl group or a heterocyclic group. Z is an atomic group necessary for forming a heterocycle with a nitrogen atom and a benzene ring. Moreover, these groups may have a substituent. ) A photoconductor for electrophotography, comprising at least one compound selected from the group consisting of hydrazone compounds represented by 2. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer has a charge generating layer made of a charge generating material and a charge transporting layer having a charge transporting material dispersed in a binder resin. . 3. A reaction product of an oxytitanium phthalocyanine compound with (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol is an X-ray diffraction pattern for Cu-Kα. 3. The electrophotographic photoreceptor according to claim 1, which has a main peak in a spectrum at a Bragg angle (2θ ± 0.2 °) of 9.5 °. 4. A reaction product of an oxytitanium phthalocyanine compound with (2R, 3R) -2,3-butanediol and / or (2S, 3S) -2,3-butanediol is X-ray diffraction on Cu-Kα. 3. The electrophotographic photoconductor according to claim 1, which has peaks at 8.3 °, 24.7 ° and 25.1 ° of Bragg angle (2θ ± 0.2 °) in the spectrum. 5. The photosensitive layer containing a charge generating material is Cu--
The electrophotographic photoreceptor according to claim 1, which has a main peak at 8.3 ° of a Bragg angle (2θ ± 0.2 °) in an X-ray diffraction spectrum with respect to Kα. 6. The binder resin used as the charge transport material is represented by the general formula (3): (In the formula, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and R ¹¹ and R ¹² are each independently
Represents a hydrogen atom, an alkyl group or an aromatic group. Moreover, these groups may have a substituent. ) A polycarbonate having a repeating unit represented by the general formula (4): (In the formula, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and W represents a group of atoms necessary for forming a carbocycle and a heterocycle. A polycarbonate having a repeating unit represented by the general formula (3), a repeating unit represented by the general formula (3) and a general formula (5) (In the formula, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and these groups may have a substituent). General formula (6) (In the formula, the hydrogen atom on the aromatic ring may be substituted with a halogen atom or an alkyl group, and these groups may have a substituent.) A polyarylate having a repeating unit 6. The electrophotographic photoconductor according to claim 1, comprising at least one or more types of polycarbonate or polyarylate selected from the group.