JPH07179427A - Homophthalic derivative and electrophotographic photoreceptor containing the same - Google Patents

Abstract

PURPOSE:To obtain a new homophthalic acid derivative which is useful as an acceptor compound used for the electrophotographic material and gives an electrophotographic photoreceptor of high sensitivity and high durability. CONSTITUTION:A compound of formula I (R1 is an alkyl, halogen, CN, NO2; R2 are an alkyl, cycloalkyl or phenyl each of which may be unsubstituted or substituted; n is 0 to 4), or a compound of formula II (Ars are substituted or unsubstituted phenyl, polycyclic aromatic group or heterocyclic group, respectively). The compound of formula I is obtained by reaction of a homophthalic anhydride with an amine of formula IV. Further, a compound of formula I is allowed to react with an aldehyde of formula V in the presence of a basic catalyst to give a compound of formula II. The photosensitive layer is formed with an electric charge generating layer and an electric charge transporting layer on a conductive support, a compound of formula II is included in the electric charge transporting layer to give an electrophotographic photoreceptor of high sensitivity and high durability.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel homophthalic acid derivative useful as an acceptor compound used in an electrophotographic photoreceptor, an intermediate for the production thereof, and electrophotography containing the homophthalic acid derivative as a charge transporting substance. Regarding the photoconductor.

[0002]

2. Description of the Related Art Conventionally, as a photosensitive layer of an electrophotographic photoreceptor,
Inorganic photoconductive substances such as selenium, selenium-tellurium alloy, and zinc oxide have been widely used, but in recent years, research on electrophotographic photoreceptors using organic photoconductive substances has progressed, and some of them have been put to practical use. ing. Here, most of the photoconductors that have been put into practical use are laminated electrophotographic photoconductors that are composed of a photoconductive layer having a charge-generating layer and a charge-transporting layer, and a photoconductive layer made of an inorganic photoconductive material. The electrophotographic photoconductor is actively designed, which is improved in terms of sensitivity and photoconductor life, which are inferior to those of the human body, and is low in cost, and takes advantage of organic photoconductive substances such as safety and versatility. It became so.

This type of laminated electrophotographic photosensitive member is generally a charge generating layer made of a charge generating substance such as a pigment and a dye, and a charge transporting layer made of a charge transporting substance such as hydrazone and pyrazoline on a conductive support. Are sequentially formed. Due to the property of the electron transporting charge transport material, they are of the hole transfer type and have sensitivity when negatively charged on the surface of the photoreceptor. However, with negative charging, the corona discharge used during charging is more unstable than with positive charging, and ozone is about 10 times as much as during positive charging.
There is a problem that nitrogen oxides are generated, and it is easy to cause physical deterioration such as adsorption on the surface of the photoconductor and chemical deterioration, and that it worsens the environment. The toner of positive polarity has a problem that it is difficult to manufacture in view of the triboelectrification series with respect to the ferromagnetic carrier particles. In the two-component high resistance magnetic brush developing method, negatively charged toner / developing toner is used. The agent is more stable and has more flexibility in selection and use conditions, and in this respect as well, the range of application to the positive charging type photoreceptor is wide and advantageous.

Therefore, it has been proposed to use a photoreceptor using an organic photoconductive positive substance with positive charging. For example, when a charge transport layer is laminated on the charge generation layer to form a photoreceptor, the charge transport layer has a large electron transport ability, for example, 2,
Although 4,7-trinitro-9-fluorenone and the like are used, there is a problem that the substance has carcinogenicity and is extremely unsuitable for occupational health. Further, as the electron transport compound, a fluorenidene methane compound is used in JP-A-60-69657 and an anthraquinodimethane and an anron derivative are used in JP-A-61-233750. Both have a problem in repeatability, and a naphthalene dicarboxylic acid imide compound is used in JP-A-5-25136 and a naphthalenetetracarboxylic acid diimide is used in JP-A-5-25174. There is a problem that should be improved, such as poor compatibility. Further, as a positively charged photoreceptor, US Pat.
5,414, thiapyrylium salt (charge generating substance)
Is included so as to form a eutectic complex with polycarbonate (binder resin). However, this known photoconductor has a drawback that a memory phenomenon is large and a ghost is likely to occur.

Therefore, the charge generation layer containing a charge generation substance that generates holes and electrons at the time of light irradiation is used as an upper layer (surface layer), and the charge transport layer containing a charge transport substance having a hole transport ability is used as a lower layer. It is conceivable to use a photoreceptor having a laminated photosensitive layer for positive charging. However, since the positive charging photoreceptor is formed with a layer containing a charge generating substance as a surface layer, it is exposed to external effects such as irradiation of short wavelength light such as ultraviolet rays, corona discharge, humidity, mechanical friction, etc. Since the fragile charge generating substance is present in the vicinity of the surface layer, the electrophotographic performance is deteriorated during storage of the photoconductor and during the image formation process, and the image quality is deteriorated. In the conventional negative charging photoreceptor having the charge transport layer as the surface layer, the influence of the various external effects is extremely small, and rather the charge transport layer has a function of protecting the lower charge generating layer.

Therefore, for example, a thin protective layer made of an insulating and transparent resin may be provided to protect the layer containing the charge generating substance from an external action. However, the charge generated during light irradiation is the protective layer. The light irradiation effect is lost due to blocking, and the sensitivity is lowered when the thickness of the protective layer serving as the surface layer is large. Although various attempts have been made to obtain a photoconductor for positive charging as described above, there are many problems to be solved in terms of photosensitivity, memory phenomenon, occupational health and the like.

[0007]

DISCLOSURE OF THE INVENTION The present invention provides a novel homophthalic acid derivative useful as an acceptor compound or the like used in an electrophotographic photoreceptor, a production intermediate thereof, and a charge generating substance and charge transporting material on a conductive support. An electrophotographic photoreceptor provided with a photosensitive layer containing a substance, which is characterized by using the homophthalic acid derivative as a high-performance charge transporting substance having particularly good compatibility with a binder resin, and having high sensitivity and durability. The object is to provide a good electrophotographic photoreceptor.

[0008]

Means for Solving the Problems The inventors of the present invention have conducted research to solve the above-mentioned problems, and as a result, have found a specific group of compounds and completed the present invention. That is, according to the present invention, a homophthalic acid derivative represented by the following general formula (I),

[Chemical 1] (In the formula, R ₁ represents an alkyl group, a halogen atom, a cyano group, and a nitro group, R ₂ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group,
Alternatively, it represents a substituted or unsubstituted phenyl group, and n represents an integer of 0-4. ) And a homophthalic acid derivative represented by the following general formula (II) are provided.

[Chemical 2] (In the formula, R ₁ represents an alkyl group, a halogen atom, a cyano group, and a nitro group, R ₂ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group,
Alternatively, it represents a substituted or unsubstituted phenyl group, Ar
Represents a substituted or unsubstituted phenyl group, a substituted or polycyclic aromatic group, or a substituted or unsubstituted heterocyclic group,
n represents an integer of 0 to 4. ) Also, according to the invention,
An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon as an essential component, wherein the photosensitive layer contains a homophthalic acid derivative represented by the general formula (II). An electrophotographic photoreceptor is provided which further comprises a photosensitive layer comprising a charge generating layer and a charge transporting layer, and at least the homophthalic acid derivative represented by the general formula (II) is contained in the charge transporting layer. Also provided is an electrophotographic photoreceptor characterized by further comprising the photosensitive layer as a single layer containing at least a charge-generating substance and a charge-transporting substance as essential components, and the charge-transporting substance represented by the general formula (II) There is provided an electrophotographic photosensitive member characterized by containing a homophthalic acid derivative represented by

The present invention will be described in more detail below. In the general formula (I) and R ₁ in the general formula (II), as the alkyl group, an alkyl group such as an alkyl group such as a methyl group, an ethyl group, a butyl group, a hexyl group and an octyl group is halogen, Examples of the atom include a fluorine atom, a chlorine atom and a bromine atom.

In R ₂ of the above general formula (I) and the above general formula (II), the alkyl group represents an alkyl group such as a methyl group, an ethyl group, a butyl group, a hexyl group and an octyl group. As the substituent, a fluorine atom,
A halogen atom such as a chlorine atom, a methoxy group, an alkoxy group such as an ethoxy group, a cyclohexyl group, a 4-butoxycarbonylcyclohexyl group, a cycloalkyl group such as a 4-hexyloxycarbonylcyclohexyl group, and a cyclopentyl group as a cycloalkyl group, Examples thereof include a cyclohexyl group and the like, and examples of the substituent include an alkyl group such as a methyl group and an ethyl group, an butoxycarbonyl group, an alkoxycarbonyl group such as a hexyloxycarbonyl group, and a substituent for the phenyl group. Is an alkyl group such as a methyl group, an ethyl group, a butyl group, a t-butyl group or a hexyl group, a substituted alkyl group such as a trifluoromethyl group, a halogen atom such as a fluorine atom or a chlorine atom, an alkoxy such as a methoxy group or an ethoxy group. Group, methoxycarbonyl group An ethoxycarbonyl group, an alkoxycarbonyl group such as butoxycarbonyl group, a cyano group, and a nitro group.

In the general formula (II), the polycyclic aromatic group of Ar is a naphthyl group, anthracenyl group, phenanthrenyl group or pyrenyl group, and the heterocyclic group is a pyridyl group, a furanyl group or a quinolyl group. Can be mentioned. Further, as a substituent of the phenyl group, the polycyclic aromatic group or the heterocyclic group in Ar, a methoxy group,
Alternatively, an alkoxy group such as an ethoxy group, an alkyl group such as a methyl group, a propyl group, a butyl group, or a t-butyl group, a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom, and a halogenated alkyl group such as a trifluoromethyl group. , A methoxycarbonyl group, an ethoxylcarbonyl group, an alkoxycarbonyl group such as a butoxycarbonyl group, a cyano group, a nitro group, and the like.

Specific examples of the homophthalic acid derivative represented by the general formula (I) and the general formula (II) are shown in Tables 1 and 2 below.
However, the present invention is not limited to these.

[0013]

[Table 1- (1)]

[0014]

[Table 1- (2)]

[0015]

[Table 1- (3)]

[0016]

[Table 1- (4)]

[0017]

[Table 1- (5)]

[0018]

[Table 2- (1)]

[0019]

[Table 2- (2)]

[0020]

[Table 2- (3)]

[0021]

[Table 2- (4)]

[0022]

[Table 2- (5)]

[0023]

[Table 2- (6)]

[0024]

[Table 2- (7)]

[0025]

[Table 2- (8)]

[0026]

[Table 2- (9)]

[0027]

[Table 2- (10)]

[0028]

[Table 2- (11)]

Next, a method for producing the homophthalic acid derivative represented by the general formula (I) or the general formula (II) of the present invention will be described. The reaction formulas for producing the homophthalic acid derivative represented by the general formula (I) are shown in Table 3 below. The compound of the general formula (I) can be generally obtained by reacting the following homophthalic anhydride (III) with the following amine compound (IV). In the reaction, if necessary, sulfuric acid, an acid catalyst such as paratoluenesulfonic acid, pyridine,
A base catalyst such as quinoline can be used. In addition, the reaction is usually carried out without solvent, or an aromatic solvent such as toluene or xylene, or a polar solvent such as tetrahydrofuran, 1,4-dioxane or N, N-dimethylformamide, and the reaction temperature is from room temperature to 200 ° C.

Next, the compound of the general formula (II) can be generally obtained by reacting the following homophthalic acid derivative (I) with the following aldehyde compound (V) in the presence of a basic catalyst. Examples of the catalyst used in the reaction include organic bases such as pyridine, piperidine or triethylamine, acetate salts such as sodium acetate, potassium acetate or ammonium acetate, inorganic bases such as caustic soda, caustic potassium, sodium carbonate or potassium carbonate. be able to. The reaction can usually be carried out without solvent or in a polar solvent such as methanol, ethanol, butanol, tetrahydrofuran, 1,4-dioxane, or N, N-dimethylformamide. The reaction temperature is room temperature to 150 ° C, preferably -100 ° C.

[0031]

[Table 3]

The homophthalic acid derivative represented by the above general formula (II) of the present invention can be used not only as a charge transporting material for an electrophotographic photoreceptor, but also as an electronic device such as a solar cell and an organic EL element in the electronics field. Can be used for

Next, the structure of the photoconductor of the present invention will be described with reference to the drawings. As the photoreceptor, for example, as shown in FIG. 1, a layer containing a charge generating substance and optionally a binder resin on a support 1 (a conductive support or a sheet on which a conductive layer is provided) (charge generating layer). ) 2 as a lower layer, containing a charge transport material and optionally a binder resin (charge transport layer)
3, a photosensitive layer 4 having a laminated structure having 3 as an upper layer, a protective layer 5 provided on the photosensitive layer 4 of FIG. 1 as shown in FIG. 2, and a support as shown in FIG. A single-layered photosensitive layer 6 containing a charge-generating substance, a charge-transporting substance and, if necessary, a binder resin may be provided. A protective layer may be provided on the upper layer, and an intermediate layer may be provided between the support and the photoreceptor layer.

As the charge generating substance used in the present invention, either an inorganic substance or an organic substance can be used as long as it absorbs visible light and generates a free charge. For example, amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide,
Inorganic substances such as cadmium selenide, cadmium sulfur selenide, mercury sulfide, lead oxide, lead sulfide, and amorphous silicon, or bisazo dyes, polyazo dyes, triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes Dyes, cyanine dyes, styryl dyes, pyrylium dyes, quinacridone dyes, indigo dyes, perylene dyes, polycyclic quinone dyes, bisbenzimidazole dyes, indanthrone dyes, squarylium dyes, anthraquinone dyes Examples include dyes and organic substances such as phthalocyanine dyes.

Examples of the binder resin usable in the photoreceptor layer in the present invention include polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin,
Vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, polycarbonate resin, silicon resin, addition resin such as melamine resin, polyaddition resin, polycondensation resin, and repetition of these resins Copolymer resins containing two or more units, such as vinyl chloride-vinyl acetate copolymers, vinyl chloride-vinyl acetate-maleic anhydride copolymer resins, and other insulating resins, as well as poly-N-vinylcarbazole. Polymer organic semiconductors such as

As the conductive support for supporting the photosensitive layer, a metal plate such as aluminum or nickel, a metal drum or a metal foil, a plastic film on which aluminum, tin oxide, indium oxide or the like is deposited, or a conductive substance is applied. Films such as paper, plastic, or drums can be used.

In the case where the photoconductor according to the present invention is formed with a laminated structure of a charge generating layer and a charge transporting layer, that is, in the case of FIGS. 1 and 2, the charge generating layer is formed by vacuumizing a charge generating substance on a conductive support. It can be formed by vapor deposition, or by coating and drying a suitable solvent alone or dissolved or dispersed with a suitable binder resin, and drying. When the charge-generating layer is formed by dispersing the charge-generating substance, the charge-generating substance is preferably a powder having an average particle diameter of 2 μm or less, preferably 1 μm or less. That is, if the particle size is too large, the dispersion in the layer becomes poor, and the particles partially project on the surface and the surface smoothness deteriorates. Toner filming phenomenon tends to occur due to particles adhering. However, if the above-mentioned particle size is too small, it tends to agglomerate rather, the resistance of the layer increases, the crystal defects increase and the sensitivity and repeatability deteriorate, or there is a limit on fineness. The lower limit of the diameter is preferably 0.01 μm.

The charge generation layer can be provided by the following method. That is, the charge generating substance is made into fine particles in a dispersion medium by a ball mill, a homomixer, etc.,
It is a method of applying a binder resin and mixing and dispersing to obtain a dispersion liquid. In this method, if the particles are dispersed under the action of ultrasonic waves, uniform dispersion is possible. In the charge generation layer, the proportion of the charge generation substance contained in the binder resin is 20 to 200 parts by weight with respect to 100 parts by weight of the binder resin. The film thickness of the charge generation layer formed as described above is preferably 0.1 to 10 μm, particularly preferably 0.5 to 5 μm.

Next, the charge-transporting layer of the present invention is obtained by applying a homophthalic acid derivative represented by the general formula (II) dissolved or dispersed in a suitable solvent alone or together with a suitable binder resin, and then drying it. It is provided in the same manner as the charge generation layer by the method. Examples of the solvent used for the charge transport layer include N, N-dimethylformamide, toluene, xylene, monochlorobenzene, 1,2-dichloroethane, dichloromethane, 1,1,1-trichloroethane, 1,1,2-trichloroethylene. , Tetrahydrofuran, methyl ethyl ketone, cyclohexanone, ethyl acetate, butyl acetate and the like. In the charge transport layer, the charge transport material is contained in the binder resin in a proportion of 20 to 200 parts by weight with respect to 100 parts by weight of the binder resin. At this time, the thickness of the charge transport layer is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.

Next, when the photoreceptor of the present invention is formed in a single layer structure, that is, in FIG. 3, the ratio of the charge generating substance and the charge transporting substance contained in the binder resin is 100 parts by weight of the binder resin. The charge generation material is used in a proportion of 20 to 200 parts by weight, and the charge transport material is used in a proportion of 20 to 200 parts by weight. The film thickness of the single-layer photosensitive member is 7 to 50 μm, more preferably 10 to 30 μm.

Further, the intermediate layer functions as an adhesive layer or a barrier layer, and in addition to the above binder resin, for example, polyvinyl alcohol, ethyl cellulose,
Resins such as carboxymethyl cellulose, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, casein, N-alkoxymethyl nylon as they are, or those in which tin oxide or indium is dispersed, Aluminum oxide, zinc oxide,
Alternatively, a vapor deposition film of silicon oxide or the like is used. The thickness of the intermediate layer is preferably 1 μm or less. As the material used for the protective layer, it is suitable to use the above-mentioned resin as it is or to disperse a low resistance substance such as tin oxide or indium oxide. Further, an organic plasma-polymerized film can also be used, and the organic plasma-polymerized film is appropriately oxygen, nitrogen, halogen, or III in the periodic table as needed.
It may contain a group or group V atom.

[0042]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. In the examples, "parts" are "parts by weight" unless otherwise specified.

Synthesis Example 1 A commercially available homophthalic anhydride represented by the general formula (III) (36.03 g) and toluene (500 ml) were dissolved in the solution, and 20.24 g of n-hexylamine was added dropwise with stirring, and the mixture was gradually heated. The reaction was performed for 8 hours while removing water under reflux. After the reaction, toluene was distilled off, and then the residue was subjected to column chromatography using toluene as a developing solvent, and the obtained crude target product was recrystallized from n-hexane to obtain 33.95 g of the pure target product. Obtained. Melting point: 39.0 to 39.5 ° C. Elemental analysis: C (%) H (%) N (%) Measured value 73.49 7.85 5.71 Calculated value 73.44 7.81 5.71

Synthesis Examples 2 to 4 Homophthalic anhydride represented by the general formula (III),
Using the amine compound represented by the general formula (IV), a pure target product was obtained in the same manner as in Synthesis Example 1. Table 4 shows the melting points and elemental analysis results of the compounds obtained as described above.

[0045]

[Table 4]

Synthesis Example 5 2.94 g of N-hexyl homophthalic acid imide obtained in Synthesis Example 1 and 1.51 g of p-nitrobenzaldehyde were dissolved in 100 ml of ethanol, and 2 drops of piperidine were added with stirring, and the mixture was refluxed. The reaction was carried out for 6 hours. After the reaction, ethanol was distilled off, and then the residue was subjected to column chromatography using toluene as a developing solvent, and the obtained crude target product was recrystallized from ethanol to obtain 1.90 g of the pure target product. . Melting point: 125.0 to 125.8 ° C Elemental analysis: C (%) H (%) N (%) Measured value 69.85 5.90 7.41 Calculated value 69.83 5.86 7.40

Synthesis Examples 6 to 7 Using the homophthalic acid derivative represented by the general formula (I) and the aldehyde compound represented by the general formula (V), a pure target product was obtained in the same manner as in Synthesis example 5. Obtained. Table 5 shows the melting points and the results of elemental analysis of the compounds obtained as described above.

[0048]

[Table 5]

Example 1 5 parts of a bisazo dye represented by the following chemical formula (P-1) and a butyral resin (Denka butyral resin # 3000-2:
Denki Kagaku Kogyo) 2.5 parts, and tetrahydrofuran 9
2.5 parts were dispersed in a ball mill for 12 hours, and then tetrahydrofuran was added so that the concentration of the dispersion liquid was 2% by weight and redispersed to prepare a coating liquid. The prepared dispersion liquid was cast and coated on a 100 μm-thick polyester film on which aluminum was vapor-deposited by a doctor blade to form a charge generation layer having a film thickness after drying of 1.0 μm.

[Chemical 3] On the charge generation layer thus obtained, 6 parts of the exemplified compound (Compound No. II-12), 10 parts of a polycarbonate resin (K-1300: manufactured by Teijin Chemicals), methyl phenyl silicon (KF50-100 cps: Shin-Etsu Chemical). Made)
A coating solution having a composition of 0.002 parts and tetrahydrofuran (94 parts) was prepared and cast-coated with a doctor blade to form a charge-transporting layer having a thickness of 20.0 μm after drying. Aluminum electrode / charge generation A laminated electrophotographic photoreceptor (photoreceptor No. 1) composed of a layer / charge transport layer was prepared.

Examples 2 to 12 Photosensitive members were prepared in the same manner as in Example 1 except that the compounds shown in Table 6 were used instead of the exemplified compound (Compound No. II-12) of Example 1. .

Example 13 The same as Example 1 except that 6 parts of the trisazo dye represented by the following chemical formula (P-2) was used in place of 5 parts of the bisazo dye represented by the following chemical formula (P-1). The charge generation layer was prepared by the method.

[Chemical 4] On the charge generation layer thus obtained, 6 parts of the exemplified compound (Compound No. II-12), 10 parts of a polycarbonate resin (K-1300: manufactured by Teijin Chemicals), methyl phenyl silicon (KF50-100 cps: Shin-Etsu Chemical). Made)
A coating solution consisting of 0.002 parts and 94 parts of tetrahydrofuran was prepared, and a charge transport layer having a film thickness after drying of 20.0 μm was formed in the same manner as in Example 1, and aluminum electrode / charge generation layer / charge was formed. A laminated electrophotographic photosensitive member (photosensitive member No. 13) including a transport layer was prepared.

Examples 14 to 24 Photoreceptors were prepared in the same manner as in Example 13 except that the compounds shown in Table 5 were used in place of the exemplified compound of Example 13 (Compound No. II-12). .

Example 25 5 parts of x-type phthalocyanine (P-3), 5 parts of polyvinyl butyral resin (S-Rex BLS: Sekisui Chemical Co., Ltd.),
And 90 parts of tetrahydrofuran were dispersed in a ball mill for 12 hours, and then tetrahydrofuran was added so as to have a dispersion liquid concentration of 2% by weight and redispersed to prepare a coating liquid. The prepared dispersion liquid was vapor-deposited with aluminum to 100 μm.
The polyester film having a thickness of m was cast and coated with a doctor blade to form a charge generation layer having a thickness of 0.5 μm after drying. On the charge generation layer thus obtained, a coating liquid having a formulation consisting of 6 parts of the exemplified compound (Compound No. II-12), 10 parts of a polycarbonate resin (K-1300: manufactured by Teijin Chemicals), and 94 parts of tetrahydrofuran. And a charge transport layer having a thickness of 20.0 μm after dried by flow casting coating with a doctor blade, and an aluminum electrode / charge generating layer / charge transport layer It was created.

Examples 26 to 36 Photoreceptors were prepared in the same manner as in Example 25, except that the compounds shown in Table 6 were used instead of the exemplified compound of Example 25 (Compound No. II-12). .

The electrophotographic photoreceptor thus obtained was subjected to +6 KV corona charging using an electrostatic copying paper tester (SP-42: Kawaguchi Denki Seisakusho), and after being positively charged, for 20 seconds. Left in the dark, the surface potential V at that time
o was measured, and then light irradiation was performed using a tungsten lamp so that the illuminance on the surface was 40 lux, and the half-exposure amount E1 / 2 (lux · sec) was measured. The results are shown in Table 6.

[0056]

[Table 6]

Example 37 0.09 g of the compound (P-1), 15 g of a 10 wt% tetrahydrofuran solution of a polycarbonate resin (PC-Z: manufactured by Teijin Chemicals), and a donor compound (D-1) 0.9.
g, 0.6 g of the exemplified compound (Compound No. II-12),
0.3 g of a 1 wt% tetrahydrofuran solution of silicon oil (KF50: manufactured by Shin-Etsu Chemical Co., Ltd.) was weighed in a ball mill pot and ball-milled for 24 hours to prepare a coating solution. The coating liquid thus prepared was vapor-deposited with aluminum to 100
A single-layer type electrophotographic photosensitive member having a film thickness after drying was cast and coated on a polyester film having a thickness of μm with a doctor blade to prepare a single-layer type electrophotographic photosensitive member.

Examples 38 to 43 Photoreceptors were prepared in the same manner as in Example 37, except that the compounds shown in Table 7 were used instead of the exemplified compound of Example 37 (Compound No. II-12). .

Comparative Example 1 A single-layer type electrophotographic photosensitive member was prepared in the same manner as in Example 37 except that the acceptor compound of the present invention was not added.

The electrophotographic photosensitive member obtained as described above was subjected to a corona charging of +6 KV using an electrostatic copying paper tester (SP-428: Kawaguchi Denki Seisakusho), and after being positively charged, for 20 seconds. Leave in a dark place, measure the surface potential Vo at that time, and then irradiate light with a tungsten lamp so that the illuminance on the surface is 40 lux, half-exposure amount E1 / 2 (lux · sec), and light irradiation The surface potential Vr after 30 seconds was measured. Next, VO, E1 / 2, and Vr were measured after the above operation was repeated 5000 times, and the results are shown in Table 7.

[0061]

[Table 7]

[0062]

INDUSTRIAL APPLICABILITY The novel homophthalic acid derivative excellent as an acceptor compound and the intermediate for producing the same according to the present invention can be produced by a relatively simple and high yield method. It has excellent solubility or dispersibility in the binder resin. In addition, the homophthalic acid derivative of the present invention functions as a charge transporting substance having an excellent ability to accept and transport a charge generated from a charge generating substance, and an electron containing this homophthalic acid derivative as a charge transporting substance. When a photographic photoreceptor is produced, it has high sensitivity and high durability.

[0063]

[Brief description of drawings]

FIG. 1 is a cross-sectional view of a laminated electrophotographic photoreceptor of the present invention in which a charge generation layer and a charge transport layer are sequentially provided on a support.

FIG. 2 is a cross-sectional view of an electrophotographic photosensitive member according to the present invention, in which an electrophotographic photosensitive member having the cross section shown in FIG.

FIG. 3 is a cross-sectional view of a single-layer type electrophotographic photosensitive member of the present invention in which a photosensitive layer is provided on a support.

[Explanation of symbols]

 1 Support 2 Charge Generation Layer 3 Charge Transport Layer 4 Photoreceptor Layer (Layered Structure) 5 Protective Layer 6 Photoreceptor Layer (Single Layered Structure)

Claims (5)

[Claims] 1. A homophthalic acid derivative represented by the following general formula (I). [Chemical 1] (In the formula, R ₁ represents an alkyl group, a halogen atom, a cyano group, and a nitro group, R ₂ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group,
Alternatively, it represents a substituted or unsubstituted phenyl group, and n is 0.
Represents an integer of ~ 4. ) 2. A homophthalic acid derivative represented by the following general formula (II). [Chemical 2] (In the formula, R ₁ represents an alkyl group, a halogen atom, a cyano group, and a nitro group, R ₂ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group,
Alternatively, it represents a substituted or unsubstituted phenyl group, Ar
Represents a substituted or unsubstituted phenyl group, a substituted or polycyclic aromatic group, or a substituted or unsubstituted heterocyclic group,
n represents an integer of 0 to 4. ) 3. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon as an essential component, wherein the homophthalic acid represented by the general formula (II) according to claim 2 is contained in the photosensitive layer. An electrophotographic photosensitive member comprising a derivative. 4. The photosensitive layer is composed of a charge generating layer and a charge transporting layer, and at least the homophthalic acid derivative represented by the general formula (II) according to claim 2 is contained in the charge transporting layer. The electrophotographic photosensitive member according to claim 3. 5. The photosensitive layer comprises at least a charge generating substance,
4. A single layer comprising a charge transporting substance as an essential component, and the homophthalic acid derivative represented by the general formula (II) according to claim 2 is contained as the charge transporting substance. Electrophotographic photoreceptor.