JP2000137339A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enhance the sensitivity to light in the wavelength region from visible wavelengths to near infrared ones and to reduce deterioration of chargeability characteristics even in the case of being exposed to white light or the like by incorporating a specified trisazo pigment and a specified disazo pigment and a specified compound in a photosensitive layer. SOLUTION: The photosensitive layer contains a trisazo pigment represented by formula I and the disazo pigment represented by formula II and the compound represented by formula III or the like, and in formulae I-III, each of Ar1-Ar5 is, independently, a coupler residue; each of R1 and R2 is an alkyl, alkoxy, hydroxy, amino, or cyano group or the like; (l) is an integer of 0-4 and (m) is 0, 1, or 2, thus permitting the obtained electrophotographic photoreceptor to be high in sensitivity to light in the wide range of visible light to the near infrared rays and small in deterioration of chargeability characteristics even in the case of being exposed to white light or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly, to a photoreceptor having high sensitivity in a wide wavelength range from a visible light region to a near-infrared region, and further having a charging characteristic even when exposed to white light or the like. The present invention relates to an electrophotographic photoreceptor having little deterioration of the image.

[0002]

2. Description of the Related Art In recent years, there has been remarkable development of information processing system equipment using an electrophotographic system. In particular, some optical printers that convert information into digital signals and record information by light have excellent print quality and reliability. This digital recording technique is applied not only to printers but also to ordinary copying machines, and so-called digital copying machines have been developed. In addition, since a variety of information processing functions are conventionally added to a copier equipped with this digital recording technology in an analog copier, its demand is expected to increase in the future.

As a light source of an optical printer, a small, inexpensive and highly reliable semiconductor laser (LD) or light emitting diode (LED) is currently used in many cases. However, the emission wavelength of the LED that is currently widely used is 660 nm, while the emission wavelength range of the LD is in the near infrared region. Therefore, development of an electrophotographic photosensitive member having high sensitivity from a visible region to a near-infrared light region is desired.

However, the photosensitive wavelength of an electrophotographic photosensitive member is as follows.
It is almost determined by the photosensitive wavelength region of the charge generating substance used for the photoconductor. For this reason, many charge-generating substances have been developed in the past, but a single charge-generating substance with sufficiently high sensitivity in a wide photosensitive wavelength range from the visible light wavelength range to the near-infrared light wavelength range has been developed. Not.

Therefore, conventionally, it is necessary to design a photoreceptor having a wide photosensitive wavelength range by mixing a charge generating substance having high sensitivity to visible light wavelength and a charge generating substance having sensitivity to near infrared light. Various attempts have been made. Among them, an electrophotographic photoreceptor containing one or more specific trisazo pigments and one or more specific disazo pigments has high sensitivity from a visible light wavelength region to a near infrared light wavelength region. −49
No. 433. However, a photoreceptor having high sensitivity to visible light has a drawback that when the photoreceptor is exposed to white light during maintenance of a copying machine or the like, charging characteristics are deteriorated and sufficient charging cannot be obtained.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems, to provide high sensitivity from the visible light wavelength region to the near infrared light wavelength region, and to further reduce the exposure to white light. An object of the present invention is to provide an electrophotographic photoreceptor in which the charging characteristics are less deteriorated even if it is performed.

[0007]

An object of the present invention is to provide an electrophotographic photosensitive member having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, wherein the photosensitive layer is represented by the following general formula (1). A trisazo pigment represented by the following general formula (2) and a disazo pigment represented by the following general formula (2)
And / or an electrophotographic photosensitive member characterized by containing a compound represented by the following general formula (4).

[0008]

Embedded image (In the formula, Ar ₁ , Ar ₂ , and Ar ₃ represent coupler residues, which may be the same or different.)

[0009]

Embedded image (In the formula, Ar ₄ and Ar ₅ each represent a coupler residue and may be the same or different.)

[0010]

Embedded image (In the formula, R ₁ and R ₂ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. And m represents an integer of 0 to 2.)

[0011]

Embedded image (Wherein, R ₃ and R ₄ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. Represents an integer of to 4.)

More preferably, the photosensitive layer is a trisazo pigment represented by the following formula (5), a disazo pigment represented by the following formula (6) or (7), and the general formula (3) and / or the general formula (3). The electrophotographic photoreceptor is characterized by containing a compound represented by the formula (4) and a stilbene compound represented by the following general formula (8).

[0013]

Embedded image

[0014]

Embedded image

[0015]

Embedded image

[0016]

Embedded image (Wherein, Ar ₆ and Ar ₇ are a substituted or unsubstituted aryl group,
Represents a substituted or unsubstituted heterocyclic group, wherein R ₅ , R ₆ and R ₇ are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted It represents a substituted heterocyclic group, but R ₆ and R ₇ may combine with each other to form a ring. Ar ₈ represents a substituted or unsubstituted arylene group, and q represents 0 or 1. )

According to the present invention, it is possible to obtain an electrophotographic photosensitive member having high sensitivity from a visible light wavelength region to a near-infrared light wavelength region and having little deterioration of charging characteristics even when exposed to white light or the like. Can be.

Hereinafter, the present invention will be described in detail. The photosensitive layer in the electrophotographic photoreceptor of the present invention contains a trisazo pigment represented by the general formula (1) and a disazo pigment represented by the general formula (2) as charge generating substances, and further includes a charge transport material and the general formula The photosensitive layer may contain (3) or / and the compound represented by the general formula (4), and may be either a dispersion type or a function separation type.

In the case of the dispersion type, for example, a single-layer photosensitive material in which the charge generating substance, the charge transporting substance and the compound represented by the general formula (3) or / and the general formula (4) are dispersed in a binder resin. The layer is provided on a conductive support, and in the case of a function-separated type, for example, a charge generation layer containing the charge generation material and the binder resin is formed on the conductive support, and a charge transport material thereon, What is necessary is just to provide a charge transport layer containing the compound represented by the general formula (3) or / and the general formula (4) and a binder resin. In order to form a positively charged electrophotographic photosensitive member, a charge generation layer may be formed on the charge transport layer. In the case of the function-separated type, a charge transporting material may be contained in the charge generating layer. By doing so, the sensitivity particularly in a positively charged type electrophotographic photoreceptor can be improved.

The mixing ratio of the trisazo pigment represented by the general formula (1) to the disazo pigment represented by the general formula (2) depends on the kind of the pigment to be mixed, for example, the required characteristics of the electrophotographic photoreceptor. The optimum value can be individually selected in consideration of sensitivity, chargeability, gas resistance, etc., but generally, 0.01 ≦ disazo pigment / (disazo pigment + trisazo pigment) by weight ratio. It is preferable to set the range of ≦ 0.99. When this ratio is smaller than 0.01, the effect of improving sensitivity is reduced, and when it is larger than 0.99, the effect of improving sensitivity is reduced, and furthermore, the gas resistance becomes poor. Furthermore, considering the uniformity of spectral sensitivity from the visible light wavelength range to the near infrared light wavelength range,
The range of 0.1 ≦ disazo pigment / (disazo pigment + trisazo pigment) ≦ 0.9 is particularly preferable. The trisazo pigment represented by the general formula (1) is represented by the formula (5):
The specific disazo pigment represented by the general formula (2)
By using a specific disazo pigment represented by the formula (6) or (7) as the disazo pigment represented by the formula (1), higher sensitivity can be achieved.

The compounds represented by the general formulas (3) and (4) are preferably contained in a charge-transporting layer in a dispersed single-layer photosensitive layer or a function-separated photosensitive layer. When it is added to the dispersion type single layer photosensitive layer, it is preferably added in an amount of 0.1 to 10% by weight based on the binder resin, and when it is added to the charge transport layer, it is added to the binder resin. It is preferable to add 0.1 to 10% by weight. When the addition amount is less than the lower limit, the effect of preventing the deterioration of the charging characteristics due to exposure of the electrophotographic photoreceptor to white light or the like becomes insufficient, and when the addition amount is larger than the upper limit,
Although it has the effect of preventing the deterioration of the charging characteristics, the electrostatic characteristics such as sensitivity deteriorate.

As the charge transporting substance used for forming the dispersion type single-layer photoreceptor or the charge transporting layer, any conventionally known charge transporting substance having high mobility and high chargeability can be used. be able to. Among them, it is preferable to use the distilbene compound represented by the general formula (8). Further, as the binder resin used when forming the dispersion type single-layer photosensitive layer, or the charge generation layer or the charge transport layer, a conventionally known binder resin for an electrophotographic photosensitive member having good insulation properties is used. Anything can be used as long as it is not particularly limited.

Examples of the binder resin include polycarbonate (bisphenol A type, bisphenol Z type), polyester, methacrylic resin, acrylic resin,
Polyethylene, polyvinyl chloride, polyvinyl acetate, polystyrene, phenolic resin, epoxy resin, polyurethane, polyvinylidene chloride, alkyd resin, silicone resin, polyvinyl carbazole, polyvinyl butyral,
Examples include polyvinyl formal, polyarylate, polyacrylamide, polyamide phenoxy resin and the like.
These binder resins can be used alone or as a mixture of two or more.

The electrophotographic photoreceptor is formed by the constitution of the photosensitive layer as described above, the charge generating substance, the charge transporting substance, the compounds represented by the general formulas (3) and (4) and the binder resin. In the case of forming, there is a preferred range in the thickness and composition ratio of the photosensitive layer, in the case of a negatively charged electrophotographic photosensitive member in which a charge generation layer and a charge transport layer are formed in this order on a conductive support. The ratio of the charge generating substance in the charge generating layer is preferably 20% by weight or more based on the binder resin.
The ratio of the charge transport material in the charge transport layer is preferably 20 to 200% by weight based on the binder resin. The thickness of the charge generation layer is preferably 0.01 to 5 μm, and the thickness of the charge transport layer is preferably 5 to 100 μm.

In the case of a positively charged electrophotographic photosensitive member in which a charge transport layer and a charge generation layer are formed on a conductive support in this order, the ratio of the charge transport material in the charge transport layer to the binder resin is determined. Preferably it is 20 to 200% by weight,
Further, it is preferable that the ratio of the charge generation material in the charge generation layer is 20% by weight or more based on the binder resin. The thickness of the charge transport layer is preferably 5 to 100 μm, and the thickness of the charge generation layer is preferably 0.1 to 1.0 μm.

Further, it is preferable that the charge generating layer contains a charge transporting material. By including the charge transporting material, an increase in residual potential can be suppressed and sensitivity can be improved. In this case, the content of the charge transporting material is preferably 20 to 200% by weight based on the binder.
In the case of a so-called dispersion-type single-layer photosensitive layer in which the charge generation material, the charge transport material, and the compounds represented by the general formulas (3) and (4) are dispersed in a binder resin, The proportion of the charge generating substance in the photosensitive layer is preferably from 5 to 95% by weight based on the binder resin, and the proportion of the charge transporting substance is preferably from 30 to 200% by weight based on the binder resin.
The thickness of the photosensitive layer is preferably from 10 to 100 μm.

Further, a phenol compound, a hydroquinone compound, a hindered phenol compound, a phenol compound, a hindered phenol compound, or the like may be added to the dispersion type single-layer photosensitive layer or the function separation type charge generation layer or the charge transport layer in order to improve chargeability and gas resistance. A so-called antioxidant, such as a hindered amine compound or a compound in which hindered amine and hindered phenol are present in the same molecule, can be added.

As the conductive support in the present invention, a conductive support having a volume resistance of 10 ¹⁰ Ω · cm or less, for example, aluminum, nickel, chromium, nichrome, copper,
Metals such as silver, gold or platinum, or metals or metal oxides such as indium oxide and tin oxide, copper iodide and the like were coated on a film or cylindrical drum, belt-like film, paper, etc. by vapor deposition or sputtering. Or belts and belts made of aluminum, aluminum alloy, nickel, stainless steel, etc. I. , I. I. ,
After forming into a tube by a method such as extrusion or drawing, a tube subjected to surface treatment by cutting, superfinishing, polishing, or the like can be used. Further, a conductive powder such as carbon black, indium oxide, tin oxide or the like may be dispersed in a suitable resin and coated on a plastic or the like.

Further, in the electrophotographic photoreceptor of the present invention, an intermediate layer may be provided between the photosensitive layer and the conductive support in order to improve adhesion, charge blocking property and the like. Further, a protective layer may be provided on the photosensitive layer in order to improve mechanical durability such as abrasion resistance.

The trisazo pigment represented by the general formula (1) in the present invention is, for example, disclosed in JP-A-53-13234.
The disazo pigment represented by the general formula (2) can be produced by the method described in JP-A No.
It can be produced by the method described in JP-A-22834.

The coupler residues Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , A in the trisazo pigment represented by the general formula (1) or the disazo pigment represented by the general formula (2)
r ₅ is, for example, be introduced by coupler shown below, but the invention is not limited thereto.

[0032]

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[0033]

[Table 1-1]

[0034]

[Table 1-2]

[0035]

Embedded image

[0036]

[Table 2-1]

[0037]

[Table 2-2]

[0038]

Embedded image

[0039]

[Table 3]

[0040]

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[0041]

[Table 4-1]

[0042]

[Table 4-2]

[0043]

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[0044]

[Table 5]

[0045]

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[0046]

[Table 6]

[0047]

Embedded image

[0048]

[Table 7]

[0049]

Embedded image

[0050]

[Table 8]

[0051]

Embedded image

[0052]

[Table 9]

[0053]

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[0054]

[Table 10]

[0055]

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[0056]

[Table 11-1]

[0057]

[Table 11-2]

[0058]

[Table 11-3]

[0059]

[Table 11-4]

[0060]

[Table 11-5]

[0061]

Embedded image

[0062]

[Table 12-1]

[0063]

[Table 12-2]

[0064]

[Table 12-3]

[0065]

[Table 12-4]

[0066]

Embedded image

[0067]

[Table 13]

[0068]

Embedded image

[0069]

[Table 14]

In the present invention, by including a compound represented by the following general formula (3) and / or the following general formula (4) in the photosensitive layer, the charging characteristics deteriorated by exposure to white light or the like can be obtained. Can be improved.

[0071]

Embedded image (In the formula, R ₁ and R ₂ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. And m represents an integer of 0 to 2.)

[0072]

Embedded image (Wherein, R ₃ and R ₄ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. Specific examples of the compounds represented by the general formulas (3) and (4) are shown in the following table, but are not limited thereto.

[0073]

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[0074]

[Table 15-1]

[0075]

[Table 15-2]

[0076]

[Table 15-3]

[0077]

[Table 15-4]

[0078]

[Table 15-5]

[0079]

[Table 15-6]

[0080]

[Table 15-7]

[0081]

[Table 15-8]

[0082]

[Table 15-9]

[0083]

[Table 15-10]

[0084]

[Table 15-11]

[0085]

Embedded image

[0086]

[Table 16-1]

[0087]

[Table 16-2]

[0088]

[Table 16-3]

[0089]

[Table 16-4]

[0090]

[Table 16-5]

[0091]

[Table 16-6]

[0092]

[Table 16-7]

[0093]

[Table 16-8]

[0094]

[Table 16-9]

[0095]

[Table 16-10]

[0096]

[Table 16-11]

[0097]

[Table 16-12]

[0098]

[Table 16-13]

Next, the charge transport material used in the present invention will be described. As the charge transporting substance, a known substance as a hole transporting substance or an electron transporting substance can be used. Examples of the hole transport material include poly-N-carbazole and derivatives thereof, poly-γ-carbazolylethyl glutamate and derivatives thereof, pyrene-formaldehyde condensates and derivatives thereof, polyvinylpyrene, polyvinylphenanthrene, oxazole derivatives, and imidazole derivatives. ,
Triphenylamine derivative or the following general formula (9)
To (26). (1) JP-A-55-154955, JP-A-55-15
Compound represented by the following general formula (9) disclosed in JP-A-6954

[0100]

Embedded image (Wherein, R ¹⁰¹ represents a methyl group, an ethyl group, a 2-hydroxyethyl group or a 2-chloroethyl group, R ¹⁰² represents a methyl group, an ethyl group, a benzyl group or a phenyl group, R ¹⁰³ represents a hydrogen atom, a chlorine atom Atom, bromine atom, carbon number 1
Represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group or a nitro group. (2) Compound represented by the following general formula (10) disclosed in JP-A-55-52063.

[0101]

Embedded image (In the formula, Ar ¹⁰¹ represents a naphthalene ring, an anthracene ring, a styryl ring, or a substituent thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R ¹⁰⁴ represents an alkyl group or a benzyl group.) Compounds represented by the following general formula (11) disclosed in Japanese Unexamined Patent Publication No. 56-81850

[0102]

Embedded image (Wherein, R ¹⁰⁵ represents an alkyl group, a benzyl group, a phenyl group, or a naphthyl group, and R ¹⁰⁶ represents a hydrogen atom,
Represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, a diaralkylamino group or a diarylamino group, r represents an integer of 1 to 4, and when n is 2 or more, R ¹⁰⁶ represents They may be the same or different. R ¹⁰⁷
Represents a hydrogen atom or a methoxy group. (4) A compound represented by the following general formula (12) disclosed in JP-B-51-10983.

[0103]

Embedded image (Wherein ¹⁰⁸ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group,
R ¹⁰⁹ and R ¹¹⁰ may be the same or different,
Represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group or a substituted or unsubstituted aralkyl group, and R ¹⁰⁹ and R ¹¹⁰ are bonded to each other to form a nitrogen-containing heterocyclic ring. May be. R ¹¹¹ may be the same or different and include a hydrogen atom,
Represents an alkoxy group or a halogen atom. (5) A compound represented by the following general formula (13) disclosed in JP-A-51-94829.

[0104]

Embedded image (Wherein, R ¹¹² represents a hydrogen atom or a halogen atom,
Ar ¹⁰² represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group or carbazolyl group. (6) Compound represented by the following general formula (14) disclosed in JP-A-52-128373.

[0105]

Embedded image (Wherein, R ¹¹³ represents a hydrogen atom, a halogen atom, a cyano group,
Represents an alkoxy group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and Ar ¹⁰³ represents a group represented by the following general formula. )

[0106]

Embedded image (R ¹¹⁴ represents an alkyl group having 1 to 4 carbon atoms, R ¹¹⁵ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a dialkylamino group; 1 or 2, when s is 2, R ¹¹⁵
May be the same or different, and R ¹¹⁶ and R ¹¹⁷ represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group. (7) A compound represented by the following general formula (15) disclosed in JP-A-56-29245.

[0107]

Embedded image (Wherein, R ^{118 is a} carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, and these substituents are dialkylamino groups , An alkyl group, an alkoxy group, a carboxy group or an ester thereof, a halogen atom, a cyano group, an aralkylamino group, an N-alkyl-N-aralkylamino group, an amino group, a nitro group and an acetylamino group. (8) A compound represented by the following general formula (16) disclosed in JP-A-58-58552.

[0108]

Embedded image (In the formula, R ¹¹⁹ represents a lower alkyl group, a substituted or unsubstituted phenyl group or a benzyl group, and R ¹²⁰ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group or a lower alkyl group. Or an amino group substituted with a benzyl group, and s is 1 or 2
Represents an integer. (9) A compound represented by the following general formula (17) disclosed in JP-A-57-73075.

[0109]

Embedded image (Wherein, R ¹²¹ represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, R ¹²² and R ¹²³ represents an alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group, R ¹²⁴ is A hydrogen atom, a lower alkyl group or a substituted or unsubstituted phenyl group, and Ar ¹⁰⁴ represents a substituted or unsubstituted phenyl group or a naphthyl group.) (10) As disclosed in JP-A-58-198043. Compound represented by the following general formula (18)

[0110]

Embedded image (Where t is an integer of 0 or 1, R ¹²⁵ represents a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group, Ar ¹⁰⁵ represents a substituted or unsubstituted aryl group, and R ¹²⁶ represents a substituted alkyl group Represents an alkyl group or a substituted or unsubstituted aryl group, and A represents a 9-anthryl group, a substituted or unsubstituted carbazolyl group or a group represented by the following general formula.)

[0111]

Embedded image (R ¹²⁷ is a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or —N (R ¹²⁸ , R ¹²⁹ ) (provided that R ¹²⁸
And R ¹²⁹ represent an alkyl group, a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group,
R ¹²⁸ and R ¹²⁹ may be the same or different, R ¹²⁸
And R ¹²⁹ may form a ring), and v is 0, 1,
An integer of 2 or 3, and when v is 2 or more, R
¹²⁷ may be the same or different. Also, when t is 0,
A and R ¹²⁵ may form a ring together. (11) A compound represented by the following general formula (19) disclosed in JP-A-49-105537.

[0112]

Embedded image (Wherein R ¹³⁰ , R ¹³¹ and R ¹³² represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a dialkylamino group or a halogen atom, and t represents 0 or 1). Compound represented by the following general formula (20) disclosed in 139066

[0113]

Embedded image (Wherein, R ¹³³ and R ¹³⁴ represent an alkyl group including a substituted alkyl group, or a substituted or unsubstituted aryl group;
A ¹ represents a substituted amino group, a substituted or unsubstituted aryl group or an allyl group. (13) Compound represented by the following general formula (21) disclosed in JP-A-52-1390065.

[0114]

Embedded image (Wherein X ² represents a hydrogen atom, a lower alkyl group or a halogen atom, R ¹³⁵ represents an alkyl group containing a substituted alkyl group, or a substituted or unsubstituted aryl group;
² represents a substituted amino group or a substituted or unsubstituted aryl group. (14) A compound represented by the following general formula (22) disclosed in JP-A-58-32372.

[0115]

Embedded image (Wherein, R ¹³⁶ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n represents an integer of 0 to 4,
¹³⁷ and R ¹³⁸ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. (15) A compound represented by the following general formula (23) disclosed in JP-A-2-178669.

[0116]

Embedded image (Wherein R ¹³⁹ , R ¹⁴¹ and R ¹⁴² represent a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom or a substituted or unsubstituted R ¹⁴⁰ represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, provided that R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ and R ¹⁴² are all hydrogen atoms. K, l, r and w are 1, 2, 3
Or, when each is an integer of 2, 3 or 4, R ¹³⁹ , R ¹⁴⁰ , R ¹⁴¹ and R ¹⁴² may be the same or different. (16) A compound represented by the following general formula (24) disclosed in JP-A-1-77839.

[0117]

Embedded image (In the formula, Ar ¹⁰⁶ represents a condensed polycyclic hydrocarbon group having 18 or less carbon atoms, and R ¹⁴³ and R ¹⁴⁴ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted or unsubstituted group. (17) A substituted phenyl group, which may be the same or different.) (17) A compound represented by the following formula (25) disclosed in JP-A-62-98394

[0118]

Embedded image (Wherein, Ar ¹⁰⁷ represents a substituted or unsubstituted aromatic hydrocarbon group, and A ³ represents -Ar ¹⁰⁷ ′ -N (R ¹⁴⁵ , R ¹⁴⁶ )
(However, Ar ¹⁰⁷ represents a substituted or unsubstituted aromatic hydrocarbon group, and R ¹⁴⁵ and R ¹⁴⁶ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group). (18) A compound represented by the following general formula (26) disclosed in JP-A-4-230764

[0119]

Embedded image (In the formula, Ar ¹⁰⁸ represents an aromatic hydrocarbon group, R ¹⁴⁷ represents a hydrogen atom, a substituted or unsubstituted alkyl group or an aryl group. T is 0 or 1, s is 1 or 2, and t is When = 0 and s = 1, Ar ¹⁰⁸ and R ¹⁴⁷ may form a ring together.)

Specific examples of the compound represented by the general formula (9) include 9-ethylcarbazole-3-aldehyde-
Examples thereof include 1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1-benzyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1,1-diphenylhitrazone and the like.

Specific examples of the compound represented by the general formula (10) include, for example, 4-diethylaminostyryl-β-aldehyde-1-methyl-1-phenylhydrazone, 4-methoxynaphthalene-1-aldehyde-1 −
Benzyl-1-phenylhydrazone and the like.

Specific examples of the compound represented by the general formula (11) include, for example, 4-methoxybenzaldehyde-
1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde-1-benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde-1,
1-diphenylhydrazone, 4-methoxybenzaldehyde-1-benzyl-1- (4-methoxy) phenylhydrazone, 4-diphenylaminobenzaldehyde-1
-Benzyl-1-phenylhydrazone, 4-dibenzylaminobenzaldehyde-1,1-diphenylhydrazone and the like.

Specific examples of the compound represented by the general formula (12) include, for example, 1,1-bis (4-dibenzylaminophenyl) propane, tris (4-diethylaminophenyl) methane, 1,1- Bis (4-dibenzylaminophenyl) propane, 2,2′-dimethyl-
4,4'-bis (diethylamino) -triphenylmethane and the like.

Specific examples of the compound represented by the general formula (13) include 9- (4-diethylaminostyryl) anthracene and 9-bromo-10- (4-diethylaminostyryl) anthracene.

Specific examples of the compound represented by the general formula (14) include, for example, 9- (4-dimethylaminobenzylidene) fluorene, 3- (9-fluorenylidene) -9-ethylcarbazole and the like. .

Further, specific examples of the compound represented by the general formula (15) include, for example, 1,2-bis (4-diethylaminostyryl) benzene, 1,2-bis (2,4-
Dimethoxystyryl) benzene and the like.

Specific examples of the compound represented by the general formula (16) include 3-styryl-9-ethylcarbazole, 3- (4methoxystyryl) -9-ethylcarbazole and the like.

Specific examples of the compound represented by the general formula (17) include, for example, 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolylaminostilbene, 1- (4-diphenylaminostyryl) ) Naphthalene, 1- (4-diethylaminostyryl) naphthalene and the like.

Further, specific examples of the compound represented by the general formula (8) are shown in the following Tables.

[0130]

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[0131]

[Table 17-1]

[0132]

[Table 17-2]

[0133]

[Table 17-3]

[0134]

[Table 17-4]

[0135]

[Table 17-5]

[0136]

[Table 17-6]

[0137]

[Table 17-7]

[0138]

[Table 17-8]

[0139]

[Table 17-9]

[0140]

[Table 17-10]

[0141]

[Table 17-11]

[0142]

[Table 17-12]

[0143]

[Table 17-13]

Specific examples of the diarylaminostyrene compound when q = 1 in the general formula (8) are shown in the following table.

[0145]

[Table 18]

Specific examples of the compound represented by the general formula (19) include, for example, 1-phenyl-3- (4-
Diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazolin, 1-phenyl-3- (4-dimethylaminostyryl) -5- (4-dimethylaminophenyl) pyrazolin and the like.

Specific examples of the compound represented by the general formula (20) include, for example, 2,5-bis (4-diethylaminophenyl-1,3,4-oxadiazole, 2-N,
N-diphenylamino-5- (4-diethylaminophenyl) -1,3,4-oxadiazole, 2- (4-dimethylaminophenyl) -5- (4-diethylaminophenyl) -1,3,4-oxa Diazole and the like.

Specific examples of the compound represented by the general formula (21) include, for example, 2-N, N'-diphenylamino-5- (N-ethylcarbazol-3-yl)-
1,3,4-oxadiazole, 2- (4-diethylaminophenyl) -5- (N-ethylcarbazole-3-
Yl) -1,3,4-oxadiazole and the like.

Specific examples of the compound represented by the general formula (22) include, for example, N, N'-diphenyl-N, N '
-Bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine, 3,3'-dimethyl-N,
N, N ', N'-tetrakis (4-methylphenyl)-
[1,1′-biphenyl] -4,4′-diamine and the like.

Specific examples of the compound represented by the general formula (23) include, for example, 4'-methoxy-N, N '
-Diphenyl- [1,1'-biphenyl] -4-amine, 4'-methyl-N, N-bis (4-methylphenyl)-[1,1'-biphenyl] -4-amine, 4'-
Methoxy-N, N-bis (4-methylphenyl)-
[1,1′-biphenyl] -4-amine and the like.

Specific examples of the compound represented by the general formula (24) include, for example, 1-diphenylaminopyrene, 1
-Di (p-tolylamino) pyrene;

Further, specific examples of the compound represented by the general formula (25) include, for example, 1,4-bis (4-diphenylaminostyryl) benzene, 1,4- [bis (4-
Di (p-tolyl) aminostyryl] benzene and the like.

Specific examples of the compound represented by the general formula (26) include 1- (4-diphenylaminostyryl) pyrene and 1- [4-di (p-tolyl) aminostyryl] pyrene. No.

Examples of the electron transporting substance include chloranil, bromanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,
4,8-trinitrothioxanthone, 2,6,8-trinitro-indeno 4H-indeno [1,2-b] thiophen-4-one, 1,3,7-trinitrodibenzothiophene-5,5-dioxide , 3,5-dimethyl-
3 ', 5'-di-tert-butyl-4,4'-diphenoquinone and the like. These charge transport materials can be used alone or in combination of two or more.

The electrophotographic photosensitive member of the present invention can be easily prepared, for example, as follows. That is, at least one kind of the trisazo pigment represented by the general formula (1) and at least one kind of the disazo pigment represented by the general formula (2), the charge transport material, and the general formula (3) or / and the general formula A compound represented by (4) is added together in an appropriate dispersion medium, and a binder resin is added thereto, if necessary, using a ball mill, a vibration mill, a disk vibration mill, an attritor, a sand mill, an ultrasonic dispersion device, or the like. The pigment is pulverized and dispersed into particles having a particle size of 1 μm or less, and the resulting dispersion is applied on a conductive support and dried to prepare an electrophotographic photoreceptor having a dispersive single-layer photosensitive layer. .

In addition, at least one kind of the trisazo pigment represented by the general formula (1) and at least one kind of the disazo pigment represented by the general formula (2) are optionally added together in an appropriate dispersion medium, if necessary. Ball mill with binder resin
Vibration mill, disk vibration mill, attritor, sand mill,
Using an ultrasonic dispersing device or the like, the pigment is pulverized and dispersed into particles having a particle size of 1 μm or less, the dispersion is applied on a conductive support, and dried to form a charge generation layer. A transport substance, the compound represented by the general formula (3) or / and the general formula (4), and a binder resin are added as required, and the mixture is dissolved in an appropriate solvent, and the solution is coated on the charge generation layer. After drying, an electrophotographic photosensitive member having a layered photosensitive layer of a function separation type can be prepared.

[0157]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited to the following Examples. Example 1 25 parts by weight of a trisazo pigment represented by the following chemical formula (A) and 25 parts by weight of a disazo pigment represented by the following chemical formula (B) were dispersed together with 250 parts by weight of tetrahydrofuran in a ball mill for 5 days as a charge generating material. Molecular weight 4
250 parts by weight of Z-type polycarbonate resin (Z-200, manufactured by Mitsubishi Gas Chemical Company), tetrahydrofuran 1500
Parts by weight, 200 parts by weight of a hydrazone compound represented by the following chemical formula (C) as a charge transport material, and N shown in Table 15 above.
o. To a solution consisting of 0.1 part by weight of compound No. 21 and 0.25 part by weight of silicone oil (KF-50, manufactured by Shin-Etsu Chemical Co., Ltd.), the mixture was further dispersed for 1 day by a ball mill, and the coating liquid for a photoconductive layer was prepared. Prepared. This photoconductive layer coating liquid was applied on an aluminum cylinder having a diameter of 80 mm,
Drying was performed at 20 ° C. for 20 minutes to form a photoconductive layer having a thickness of 28 μm. On the other hand, the photoconductive coating solution was applied on an Al plate and dried at 130 ° C. for 20 minutes to form a photoconductive layer having a thickness of 28 μm.

[0158]

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[0159]

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[0160]

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Example 2 In Example 1, the preparation of the coating solution for the photoconductive layer was carried out in the same manner as described in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 1, except that 40 parts by weight of the compound No. 21 was added.

Example 3 In Example 1, the preparation of the coating solution for the photoconductive layer was performed using An electrophotographic photosensitive member was prepared in the same manner as in Example 1, except that 1 part by weight of the compound No. 21 was added.

Example 4 The procedure of Example 1 was repeated to prepare a coating solution for the photoconductive layer. Table 16
No. shown in FIG. An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.1 part by weight of the compound No. 261 was added.

Example 5 In Example 4, No. 5 shown in Table 16 was used. An electrophotographic photosensitive member was prepared in the same manner as in Example 4, except that 40 parts by weight of the compound No. 261 was added.

Example 6 In Example 4, No. 6 shown in Table 16 was used. An electrophotographic photosensitive member was prepared in the same manner as in Example 4 except that 1 part by weight of the compound No. 261 was added.

Example 7 160 parts by weight of titanium oxide (TM-1, manufactured by Fuji Titanium Co., Ltd.) and an alkyd resin (Beccolite M6401-50)
-S, manufactured by Dainippon Ink and Chemicals, Inc.), 36 parts by weight of melamine resin (Super Beckamine L-121-60, manufactured by Dainippon Ink and Chemicals, Inc.) and 100 parts by weight of methyl ethyl ketone were mixed with alumina balls having a diameter of 10 mm. Place in a 15 cm diameter glass pot, half filled by volume,
Ball milling was performed for an hour, and then 80 parts by weight of methyl ethyl ketone was added, followed by dispersion for 2 hours to prepare a coating solution for an intermediate layer. This intermediate layer coating solution was applied on an aluminum cylinder having a diameter of 80 mm and dried at 130 ° C. for 20 minutes to form an intermediate layer having a thickness of 4.5 μm. Next, 25 parts by weight of the trisazo pigment of the chemical formula (A) and the compound (B)
25 parts by weight of disazo pigment, 200 parts by weight of cyclohexanone and 200 parts by weight of methyl ethyl ketone
m PSZ balls (partially stabilized zirconia) were placed in a 15 cm diameter glass pot half-filled by volume, and ball milling (primary dispersion) was performed for 10 days. Thereafter, 300 parts by weight of cyclohexanone and 300 parts by weight of methyl ethyl ketone were added. Ball milling (secondary dispersion) was performed for 2 hours. Next, 25 parts by weight of polyvinyl butyral (BM-2, manufactured by Sekisui Chemical Co., Ltd.) was added to cyclohexanone 500.
Parts by weight and a diluent dissolved in 500 parts by weight of methyl ethyl ketone are added to the secondary dispersion to prepare a charge generation coating liquid,
The coating solution was applied on the intermediate layer and dried at 120 ° C. for 20 minutes to form a 0.2 μm-thick charge generating layer.

Next, 7 parts by weight of the charge transport material of the chemical formula (C), bisphenol Z type polycarbonate (TS205)
0, manufactured by Teijin Chemicals Limited) 10 parts by weight, N shown in Table 15 above
o. Compound No. 21 was dissolved in 0.005 parts by weight and 0.002 parts by weight of silicone oil (KF-50, manufactured by Shin-Etsu Chemical Co., Ltd.) in 100 parts by weight of tetrahydrofuran to prepare a coating liquid for a charge transport layer. The working solution was applied on the charge generation layer, and dried at 110 ° C. for 20 minutes to form a charge transport layer having a thickness of 25 μm, thereby producing an electrophotographic photosensitive member.

Example 8 In Example 7, the preparation of the coating solution for the charge transport layer was carried out in the same manner as in Example 7.
No. shown in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 7, except that 2 parts by weight of the compound No. 21 was added.

Example 9 In Example 7, the preparation of the coating solution for the charge transport layer was carried out by the following steps.
No. shown in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 7, except that 0.05 part by weight of the compound No. 21 was added.

Example 10 In Example 7, the preparation of the coating solution for the charge transport layer was carried out.
No. shown in Table 15 above. No. 21 shown in Table 16 in place of compound No. 21 An electrophotographic photosensitive member was prepared in the same manner as in Example 7, except that 0.05 parts by weight of the compound No. 261 was added.

Example 11 In Example 10, the preparation of the coating solution for the charge transport layer was carried out in the same manner as in Table 16 except that An electrophotographic photosensitive member was prepared in the same manner as in Example 10, except that 2 parts by weight of the compound No. 261 was added.

Example 12 In Example 10, the preparation of the coating solution for the charge transport layer was carried out in the same manner as described in Table 16 above. 261 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 10 except that the weight part was added.

Example 13 In Example 9, the preparation of the coating solution for the charge transport layer was carried out by the following steps.
An electrophotographic photoreceptor was prepared in the same manner as in Example 9, except that the following chemical formula (D) was used instead of the chemical formula (A), and the following chemical formula (E) was used instead of the chemical formula (B).

[0174]

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[0175]

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Example 14 In Example 12, in preparing the coating solution for the charge generation layer, the chemical formula (D) was used instead of the chemical formula (A), and the chemical formula (E) was used instead of the chemical formula (B). An electrophotographic photoreceptor was prepared in the same manner as in Example 12 except for using.

Example 15 The procedure of Example 9 was repeated to prepare a coating solution for the charge generation layer.
An electrophotographic photoreceptor was produced in the same manner as in Example 9, except that the chemical formula (D) was used instead of the chemical formula (A), and the following chemical formula (F) was used instead of the chemical formula (B).

[0178]

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Example 16 In Example 12, in preparing the coating solution for the charge generation layer, the chemical formula (D) was used instead of the chemical formula (A), and the chemical formula (F) was used instead of the chemical formula (B). An electrophotographic photoreceptor was prepared in the same manner as in Example 12 except for using.

Example 17 In Example 13, 7 parts by weight of a charge-transporting substance represented by the following chemical formula (G) and a no. An electrophotographic photosensitive member was prepared in the same manner as in Example 13, except that 0.05 part by weight of the compound No. 51 was added.

[0181]

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Example 18 In Example 17, the preparation of the coating solution for the charge transport layer was carried out in the same manner as described in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 17, except that 0.05 part by weight of the compound No. 31 was added.

Example 19 In Example 17, the preparation of a coating solution for a charge transport layer was carried out in the same manner as described in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 17, except that 0.05 parts by weight of the compound of No. 69 was added.

Example 20 In Example 17, the preparation of a coating solution for a charge transport layer was carried out in the same manner as in Table 15 except that 152 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 21 The procedure of Example 17 was repeated, except that no. 226 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 22 In Example 17, the preparation of the coating solution for the charge transport layer was carried out in the same manner as described in Table 16 above. 265 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 23 In Example 17, the preparation of a coating solution for a charge transport layer was carried out in the same manner as described in Table 16 above. 281 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 24 In Example 17, the preparation of a coating solution for a charge transport layer was carried out in the same manner as in No. 16 shown in Table 16 above. 292 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 25 In Example 17, the preparation of a coating solution for a charge transport layer was carried out in the same manner as in Table 16 except that 485 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 17 except that the weight part was added.

Example 26 In Example 15, when preparing the coating solution for the charge transport layer, 7 parts by weight of the charge transport material of the chemical formula (G) and No. 6 shown in Table 15 were used. An electrophotographic photoreceptor was prepared in the same manner as in Example 15 except that 0.05 part by weight of the compound No. 51 was added.

Example 27 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out using the No. 1 liquid shown in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 26 except that 0.05 part by weight of the compound No. 31 was added.

Example 28 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out using the No. 3 liquid as shown in Table 15 above. An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that 0.05 parts by weight of the compound of No. 69 was added.

Example 29 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out in the same manner as in Table 15 except that 152 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Example 30 In Example 26, the preparation of a coating liquid for a charge transporting layer was carried out by using Nos. 226 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Example 31 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out in the same manner as in Table 16 except that 265 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Example 32 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out using the No. 3 liquid as shown in Table 16 above. 281 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Example 33 In Example 26, the preparation of a coating solution for a charge transport layer was carried out using the preparations of Nos. 292 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Example 34 In Example 26, the preparation of a coating liquid for a charge transport layer was carried out in the same manner as in No. 16 shown in Table 16 above. 485 compounds at 0.05
An electrophotographic photoreceptor was prepared in the same manner as in Example 26 except that the weight part was added.

Comparative Example 1 The procedure of Example 1 was repeated except that, in preparing the coating solution for the photoconductive layer, the trisazo pigment of the chemical formula (A) was used and the disazo pigment of the chemical formula (B) was 50 parts by weight. An electrophotographic photoreceptor was produced in the same manner as described above.

Comparative Example 2 The procedure of Example 1 was repeated except that, in preparing the coating liquid for the photoconductive layer, the disazo pigment of the chemical formula (B) was used and the trisazo pigment of the chemical formula (A) was changed to 50 parts by weight. An electrophotographic photoreceptor was produced in the same manner as described above.

Comparative Example 3 In preparing the coating solution for the photoconductive layer in Example 1, 50 parts by weight of the X-type metal-free phthalocyanine was used instead of the trisazo pigment of the chemical formula (A) and the disazo pigment of the chemical formula (B). An electrophotographic photoreceptor was produced in the same manner as in Example 1, except for the above.

Comparative Example 4 In Example 1, the preparation of the coating solution for the charge transport layer
No. shown in Table 15 above. An electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that Compound 21 was not used.

Examples 1 to 3 obtained as described above
4. The electrophotographic photoreceptors of Comparative Examples 1-4 were subjected to 25 ° C / 50% R
In an environment of H, an electrostatic copying paper test apparatus (EPA-810)
0, manufactured by Kawaguchi Electric Manufacturing Co., Ltd.) to evaluate the electrostatic characteristics in the dynamic mode. Examples 1 to 6 and Comparative Examples 1 to 4
In the electrophotographic photoreceptor, the corona discharge of +6 (KV)
The surface potential V2 (V) after 2 seconds was measured and the surface potential V2 (V) after 2 seconds was measured. When the surface potential reached 800 (V), the light (2.5 μW / cm) was dispersed to 780 nm using a band-pass filter. ² ) Exposure to a surface potential of 80
(V) Exposure E1 / 10 (μJ
/ Cm ² ) and the surface potential V30 (V) 30 seconds after exposure. Further, the same characteristics as described above were measured after repeating the irradiation of the tungsten lamp 5 (lux) with the color temperature of 2856 ° K and the charging at +6 (KV) 30,000 times (after fatigue).

Next, the above-mentioned electrophotographic photosensitive member was mounted on an electrophotographic copying machine (Imagio MF530 modified machine, manufactured by Ricoh Company) to evaluate the image. Further, the electrophotographic photosensitive member evaluated above was exposed to white light whose light amount was adjusted to 500 lux for 30 minutes, and then the electrostatic characteristics and the image were evaluated in the same manner as above.

Further, in the electrophotographic photosensitive members of Examples 7 to 34, a corona discharge of -6 (KV) was performed for 5 seconds, negative charging was performed, and a surface potential V2 (-V) after 2 seconds was measured. When the potential reached 800 (V), light (2.5 μW / cm) was dispersed at 780 nm using a bandpass filter.
² ) Exposure, exposure amount E1 / 10 (μJ / cm ² ) necessary for light attenuating the surface potential to 80 (−V) and exposure 3
The surface potential V30 (−V) after 0 seconds was measured. Further, the same characteristics as described above were measured after repeating the irradiation of the tungsten lamp 5 (lux) with the color temperature of 2856 ° K and the charging at −6 (KV) 30,000 times (after fatigue).

Next, the above-described electrophotographic photosensitive member was mounted on an electrophotographic copying machine (Imagio MF530 modified machine, manufactured by Ricoh Company) to evaluate the image. Further, the electrophotographic photosensitive member evaluated above was exposed to white light whose light amount was adjusted to 500 lux for 30 minutes, and then the electrostatic characteristics and the image were evaluated in the same manner as above. The results are shown in the table.

[0207]

[Table 19] As is clear from the above results, the electrophotographic photosensitive members of Examples 1 to 34 have high sensitivity in the near-infrared light wavelength region,
In addition, the electrophotographic photoreceptor has less deterioration in charging characteristics even when exposed to white light or the like.

[0208]

As described above, according to the present invention, the present invention has high sensitivity from the visible light wavelength region to the near infrared light wavelength region and is exposed to white light or the like. An electrophotographic photoreceptor with little deterioration in charging characteristics can be obtained, and when an image is formed using the electrophotographic photoreceptor of the present invention, no white spots, black spots or background stains are generated, High quality images can always be obtained.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) G03G 5/05 104 G03G 5/05 104B

Claims (11)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, wherein the photosensitive layer comprises a trisazo pigment represented by the following general formula (1): An electrophotographic photoreceptor comprising a disazo pigment represented by the formula (2) and a compound represented by the following general formula (3). Embedded image (In the formula, Ar ₁ , Ar ₂ , and Ar ₃ each represent a coupler residue and may be the same or different.) (In the formula, Ar ₄ and Ar ₅ each represent a coupler residue, and may be the same or different.) (In the formula, R ₁ and R ₂ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. And m represents an integer of 0 to 2.) 2. An electrophotographic photosensitive member having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, wherein the photosensitive layer comprises a trisazo pigment represented by the following general formula (1): An electrophotographic photoreceptor comprising a disazo pigment represented by the formula (2) and a compound represented by the following general formula (4). Embedded image (Wherein, Ar ₁ , Ar ₂ , and Ar ₃ each represent a coupler residue, and may be the same or different.) (In the formula, Ar ₄ and Ar ₅ each represent a coupler residue, and may be the same or different.) (Wherein, R ₃ and R ₄ represent an alkyl group, an alkoxy group, a hydroxy group, an amino group, a cyano group, a nitro group, a dialkylamino group, an aralkylamino group, an acetylamino group, and a halogen atom. Represents an integer of to 4.) 3. A charge-generating layer in which a photosensitive layer contains a trisazo pigment represented by the general formula (1), a disazo pigment represented by the general formula (2), a charge transport material, and the general formula (3) 2. The electrophotographic photoreceptor according to claim 1, comprising a charge transport layer containing a compound represented by the formula: wherein the charge transport layer is provided on the charge generation layer. 4. A charge-generating layer in which a photosensitive layer contains a trisazo pigment represented by the general formula (1), a disazo pigment represented by the general formula (2), a charge transport material, and the general formula (4) 3. The electrophotographic photoreceptor according to claim 2, comprising a charge transport layer containing a compound represented by the formula: wherein the charge transport layer is provided on the charge generation layer. 5. The photosensitive layer contains a binder resin, and the ratio of the compound represented by the general formula (3) to the binder resin is 0.1 / 1.
2. The electrophotographic photoreceptor according to claim 1, wherein the ratio is from 00 to 100/100. 6. The photosensitive layer contains a binder resin, and the ratio of the compound represented by the general formula (4) to the binder resin is 0.1 / 1.
3. The electrophotographic photosensitive member according to claim 2, wherein the ratio is from 00 to 100/100. 7. The charge transport layer contains a binder resin, and the ratio of the compound represented by the general formula (3) to the binder resin is 0.1.
The electrophotographic photoreceptor according to claim 3, wherein the ratio is in the range of / 100 to 10/100. 8. The charge transport layer contains a binder resin, and the ratio of the compound represented by the general formula (4) to the binder resin is 0.1.
The electrophotographic photosensitive member according to claim 4, wherein the ratio is in the range of / 100 to 100/100. 9. An electrophotographic photosensitive member having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, wherein the charge generating substance in the photosensitive layer is represented by the following formula (5): The electrophotographic photosensitive member according to claim 1, further comprising a disazo pigment represented by the following formula (6). Embedded image Embedded image 10. The electron according to claim 9, wherein the charge generating substance in the photosensitive layer contains a trisazo pigment represented by the formula (5) and a disazo pigment represented by the following formula (7). Photoreceptor. Embedded image 11. The electrophotographic photoconductor according to claim 1, wherein the charge transporting substance in the photosensitive layer is a stilbene compound represented by the following general formula (8). Embedded image (Wherein, Ar ₆ and Ar ₇ are a substituted or unsubstituted aryl group,
Represents a substituted or unsubstituted heterocyclic group, wherein R ₅ , R ₆ and R ₇ are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted It represents a substituted heterocyclic group, but R ₆ and R ₇ may combine with each other to form a ring. Ar ₈ represents a substituted or unsubstituted arylene group, and q represents 0 or 1. )