JPH089579B2 - M-phenylenediamine compound and electrophotographic photoreceptor using the same - Google Patents

Description

TECHNICAL FIELD The present invention relates to an m-phenylenediamine compound suitable as a charge transport material in an electrophotographic photoreceptor and an electrophotographic photoreceptor using the same.

[Prior Art] In recent years, as an electrophotographic photoreceptor in an image forming apparatus such as a copying machine, an organic photoreceptor having excellent processability and advantageous in terms of manufacturing cost and having a large degree of freedom in functional design has been used. There is.

The Carlson process is widely used to form a copied image using an electrophotographic photosensitive member. The Carlson process includes a charging step of uniformly charging a photoconductor by corona discharge, an exposure step of exposing a document image on the charged photoconductor to form an electrostatic latent image corresponding to the document image,
Developing the electrostatic latent image with a developer containing toner to form a toner image, transferring the toner image to a base material such as paper, and fixing the toner image transferred to the base material It includes a fixing step and a cleaning step of removing the toner remaining on the photoconductor after the transfer step. In order to form a high-quality image in the Carlson process, the electrophotographic photosensitive member is required to have excellent charging characteristics and photosensitive characteristics and to have a low residual potential after exposure.

One of the means for achieving these properties is the selection of an appropriate charge transport material. Many compounds such as polyvinyl carbazole, oxadiazole compounds, pyrazoline compounds, and hydrazone compounds have been proposed as the charge transport material.

[Problems to be Solved by the Invention] However, the charge transport material described above has a relatively low drift mobility indicating a charge transport capability. Further, since the drift mobility has a large electric field strength dependency, there is a problem that the movement of charges in a low electric field is small and the residual potential is hard to pass through. Further, there is a problem that it is easily deteriorated by irradiation with ultraviolet rays.

In view of these problems, N, N, N ′, N′-tetraphenyl-containing m-phenylenediamine compounds, which have low electric field dependence of drift mobility and have good compatibility with resins.
1,3-Phenylenediamine has been proposed (Japanese Patent Application No. 62-
No. 301703). This m-phenylenediamine compound has good light resistance to ultraviolet light and the like, and exhibits stable characteristics even when used in an actual copying machine. However, there is a problem in that when the copying machine is broken down or the light is exposed to light for a long time or at a high temperature, it is irreparably damaged.

The present invention solves the above problems, and an object of the present invention is to provide an m-phenylenediamine compound having more light resistance and excellent photostability, and an electrophotographic photoreceptor using the same.

[Means and Actions for Solving the Problems] Generally, the cause of deterioration of the characteristics of the photoconductor due to photodegradation is that impurities serving as traps for the charge transport material are generated in the photoconductor. In the case of an m-phenylenediamine compound, such a photodegradation reaction is considered to be a ring-closing reaction that occurs between the central benzene ring and another phenyl group. It is considered that this reaction is likely to occur because the electron density of the molecule of the phenylenediamine compound is biased to the central benzene ring. In particular, the 5th position of the central benzene ring has a molecular structure that is easily attacked by an oxidizing substance such as oxygen during photoexcitation due to its steric configuration, and it is considered that a ring-closing reaction occurs because an electron is withdrawn from this part. Therefore,
It is thought that it is possible to suppress the reactivity and improve the stability by substituting and protecting this part with a substituent,
As a result of various experiments, by substituting this position with a predetermined substituent such as an alkyl group, an alkoxyl group, an amino group, an N-substituted amino group, an allyl group and an aryl group, charge transport properties such as drift mobility are impaired. It has been found that the light stability of the photoconductor can be effectively improved without the above.

The m-phenylenediamine compound of the present invention has the following general formula [I]: (In the formula, R ¹ , R ² , R ³ and R ⁴ are the same or different and each represents an alkyl group, an alkoxyl group, a halogen atom, an amino group, N-
Represents a substituted amino group, l, m, o, p are the same or different,
R ⁵ is an integer of 0 to ⁵ and R ⁵ is an alkyl group, an alkoxyl group, an amino group, an allyl group or an aryl group).

In the m-phenylenediamine compound, the 5th position of the central benzene ring is a substituent (alkyl group, alkoxyl group,
Amino group, N-substituted amino group, allyl group, aryl group)
By being protected by, it becomes difficult to be attacked by an oxidant or the like, the photodegradation reaction is significantly suppressed, and the stability to light is improved.

Further, the photoconductor containing the m-phenylenediamine-based compound is less likely to suffer damage than conventional photoconductors when exposed to light for a long time or under high temperature, and is excellent in light stability. There is.

[Preferred Embodiment of the Invention] In the m-phenylenediamine compound of the present invention represented by the general formula [I], the alkyl group of R ¹ , R ² , R ³ and R ⁴ is a methyl group or an ethyl group. , Propyl group,
Examples thereof include lower alkyl groups having 1 to 6 carbon atoms such as isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group and hexyl group.

As the alkoxyl group, a methoxy group, an ethoxy group,
Propoxy group, isopropoxy group, pentyloxy group,
The number of carbon atoms in the alkyl moiety such as a hexyloxy group is 1 to 6
The lower alkoxyl group of is exemplified.

The R ¹ , R ² , R ³ and R ⁴ may be the same or different from each other.

Specific examples of the m-phenylenediamine compound represented by the general formula [I] include the following compounds.

The compound represented by the above general formula [I] of the present invention can be synthesized by various methods, for example, the following series of reaction formulas [A] or [B].

[In the formula, R ⁿ and R ^s are the same or different and each represents an alkyl group, an alkoxyl group, a halogen atom, an amino group or an N-substituted amino group, and R ^a and R ^b are the same or different and each is a hydrogen atom. , An alkyl group, an alkoxy group, a halogen atom, an amino group, an N-substituted amino group, an allyl group, and an aryl group. That is, in the reaction step of the above [A], the resorcinol derivative represented by the formula (1) and the aniline derivative represented by the formula (2) are reacted with iodine by refluxing in a nitrogen stream to obtain the compound represented by the formula (3). ) The phenylenediamine compound represented by Then, the compound of the formula (3) and the iodobenzene derivative represented by the formula (4) are refluxed in a solvent (for example, nitrobenzene) in the presence of potassium carbonate and copper powder to give a compound represented by the general formula [I]. In, an m-phenylenediamine compound of the compound of the present invention having the same R ¹ and R ³ , and R ² and R ⁴ is obtained.

In the compound represented by the general formula [I], the substituent R ⁵ such as an alkyl group can be introduced into resorcinol in advance as described above, and R ⁿ (that is, R ² , R ⁴ ) can be pre-introduced into aniline, and further R ⁵ (ie R ¹ , R ³ ) can be pre-introduced into iodobenzene.

The compound represented by the general formula [I] can also be synthesized by the reaction shown in the above reaction formula [B]. That is, the phloroglysin represented by the above formula (5) and the aniline derivative represented by the formula (6) are added in the presence of iodine,
The reaction is carried out by refluxing in a nitrogen stream to obtain a phenylenediamine compound represented by the formula (7). Then, the compound of the formula (7) and the iodobenzene derivative represented by the formula (8) are added to a solvent (for example, nitrobenzene) together with potassium carbonate and copper powder and refluxed to give R in the general formula [I]. ⁵ is an N-substituted amino group, R ¹ and
It is possible to obtain the compound of the present invention in which R ³ , R ² and R ⁴ are the same. Substituents such as R ⁵ can be introduced into each starting material in advance as described above.

Further, in order to synthesize the compound of the present invention other than the compound obtained by the above reaction formula [A] or [B], for example, a compound in which R ^{1 to} R ⁴ are all different substituents, the above reaction formula [A] or By appropriately adjusting the molar ratio of the starting materials in [B],
A method is to introduce each phenyl group having the substituents R ^{1 to} R ⁴ stepwise. Further, after introducing a phenyl group having no substituent, the substituents R ^{1 to} R ⁴ and R ⁵ may be introduced successively.

The compound represented by the above general formula [I] of the present invention can be used in combination with other known charge transport materials. As the charge transport material in this case, various known electron-withdrawing compounds and electron-donating compounds can be used.

Examples of the electron-withdrawing compound include diphenoquinone derivatives such as 2,6-dimethyl-2 ′, 6′-ditert-dibutyldiphenoquinone, malononitrile, thiopyran-based compounds, tetracyanoethylene, 2,4,8- Examples include trinitrothioxanthone, 3,4,5,7-tetranitro-9-fluorenone, dinitrobenzene, dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride and dibromomaleic anhydride. It

Examples of the electron-donating compound include oxadiazole compounds such as 2,5-di (4-methylaminophenyl) and 1,3,4-oxadiazole, and 9- (4-diethylaminostyryl) anthracene. Styryl compounds, carbazole compounds such as polyvinylcarbazole, pyrazoline compounds such as 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, hydrazone compounds, triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds , Thiazole compounds, thiadiazole compounds, imidazole compounds,
Examples thereof include nitrogen-containing cyclic compounds such as pyrazole compounds and triazole compounds, and condensed polycyclic compounds.

These charge transport materials are used alone or in combination of two or more. Note that the binder resin is not always necessary when using a charge transporting material having film-forming properties such as polyvinylcarbazole.

The compound represented by the general formula [I] can be applied to both so-called single-layer type and multi-layer type electrophotographic photoreceptors.

In order to obtain a single-layer type electrophotographic photoreceptor, a photosensitive layer containing a compound represented by the above general formula [I] which is a charge transport material, a charge generating material, a binder resin and the like is provided on a conductive substrate. It may be formed.

Further, in order to obtain a laminated type electrophotographic photosensitive member, a charge generation layer containing a charge generation material is formed on a conductive substrate by means such as vapor deposition or coating, and on this charge generation layer,
The charge transport layer containing the compound represented by the general formula [I] and the binder resin may be formed. On the contrary to the above, a charge transport layer similar to the above is formed on the conductive substrate,
Then, a charge generating layer containing a charge generating material may be formed by means such as vapor deposition or coating. Further, the charge generation layer may be formed by dispersing a charge generation material and a charge transport material in a binder resin and coating the resin.

Examples of the charge generation material include selenium, selenium-tellurium, amorphous silicon, pyrylium salt, azo pigments, disazo pigments, ansanthuron pigments, phthalocyanine pigments, indigo pigments, triphenylmethane pigments, and slene pigments. Examples thereof include pigments, toluidine pigments, pyrazoline pigments, perylene pigments, quinacridone pigments, and pyrrole pigments. One kind or a mixture of two or more kinds is used so as to have an absorption wavelength range in a desired range.

Various resins can be used as the binder resin in the photosensitive layer, charge generation layer and charge transport layer. For example, styrene-based polymer, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, acrylic polymer, styrene-acrylic copolymer, polyethylene, ethylene vinyl acetate copolymer , Chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, polycarbonate, polyacrylate, polystyrene, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin And other thermoplastic resins, silicone resins, epoxy resins, phenol resins, urea resins, melamine resins, other crosslinkable thermosetting resins, and photocurable resins such as epoxy acrylate and urethane-acrylate. Of the polymer are exemplified. These binder resins may be used alone or in combination of two or more.

A solvent is used when the charge generation layer and the charge transport layer are formed by a coating method. As this solvent,
It is possible to use various organic solvents, alcohols such as methanol, ethanol, isopropanol and butanol, aliphatic hydrocarbons such as n-hexane, octane and cyclohexane, aromatic carbonization such as benzene, toluene and xylene. Hydrogen, dichloromethane, dichloroethane, carbon tetrachloride, halogenated hydrocarbons such as chlorobenzene, dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, ethers such as diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, cyclohexanone, ethyl acetate, acetic acid Examples include various solvents such as esters such as methyl, dimethylformaldehyde, dimethylformamide, dimethylsulfoxide and the like. These can be used alone or in combination of two or more.

In order to improve the sensitivity of the charge generation layer, known sensitizers such as terphenyl, halonaphthoquinones and acenaphthylene may be used together with the charge generation material. Further, a surfactant, a leveling agent, etc. may be used to improve the dispersibility of the charge transport material or the charge generating material, the dyeing property and the like.

As the conductive substrate, various materials having conductivity can be used, for example, aluminum, copper, tin, platinum, gold, silver, vanadium, molybdenum, chromium,
Examples include cadmium, titanium, nickel, palladium, indium, stainless copper, brass, and other simple metals, plastic materials in which the above metals are vapor-deposited or laminated, aluminum iodide, tin oxide, glass coated with indium oxide, or the like. It The conductive base material may be in the form of a sheet or a drum, and the base material itself may be conductive, or the surface of the base material may be conductive. As the base material, a base material having sufficient mechanical strength when used is preferable.

The compound of the present invention as the charge transport material and the binder resin can be used in various proportions within a range that does not inhibit charge transport and a range that does not crystallize, but with respect to 100 parts by weight of the binder resin. It is preferable to use 125 parts by weight to 200 parts by weight of the compound represented by the general formula [I].

The charge transport layer containing the compound represented by the general formula [I] is preferably formed to have a layer thickness of 2 to 100 μm, particularly 5 to 30 μm.

When the charge generating material is used together with a binder resin, the charge generating material and the binder resin can be used in various ratios, but the binder resin is 1 to 150 parts by weight with respect to 10 parts by weight of the charge generating material. It is desirable to use it in the ratio of.

Further, the charge generation layer containing the above charge generation material, the film thickness can be arbitrarily selected, 0.01 ~ 20μ
It is desirable that the thickness is set to m, particularly 0.1 to 10 μm.

In addition, the film thickness of the single-layer type photosensitive layer in which the compound represented by the general formula [I] and the charge generation material are present in a single layer can be arbitrarily selected, but is 2 to 100 μm, and particularly 5
The layer thickness is preferably about 30 μm.

Further, in the case of a single-layer type electrophotographic photoreceptor, between the base material and the photosensitive layer, and in the case of a laminated type electrophotographic photoreceptor, between the base material and the charge generation layer. A barrier layer may be formed between the base material and the charge transport layer and between the charge generation layer and the charge transport layer to the extent that the characteristics of the photoreceptor are not impaired. A layer may be formed.

When the charge generation layer and the charge transport layer are formed by a coating method, the charge generation material and the binder resin are known methods, for example, roll mill, ball mill, attritor, paint shaker or ultrasonic disperser. It may be prepared by dispersing and mixing using, and applying and drying this by a known means. As described above, the charge generation layer may be formed by depositing the above charge generation material.

 Hereinafter, the present invention will be described in detail with reference to examples.

Examples (1) Synthesis Example of Charge Transport Material First Synthesis Example (Synthesis of N, N, N ′, N′-tetrakis (3-tolyl) -5-methyl-1,3-phenylenediamine) 5 12.5 g (88 mmol) of -methylresorcinol (orcin) and 22.6 g of m-toluidine were reacted in the presence of 0.5 g of iodine by refluxing in a nitrogen stream for 3 days. After the reaction,
After cooling to room temperature, the resulting solid was washed with 500 ml of methanol to obtain N, N'-bis (3-tolyl) -5-methyl-1,3-phenylenediamine. Next, this N, N'-bis (3-
Tolyl) -5-methyl-1,3-phenylenediamine 15.1 g
And iodotoluene 21.8g, potassium carbonate 9.7g, copper powder 2
In the presence of g, it was added to 100 ml of nitrobenzene and refluxed for 24 hours to react. After the reaction, nitrobenzene and iodotoluene were removed by steam distillation, and the residue was washed with water and methanol. Next, the residue is added to 900 ml of benzene, the water-soluble matter is filtered off, and the 1st fraction is taken with an activated alumina column chromatography developing solution (benzene-hexane 1: 1). Further, this fraction was added to benzene-hexane 1:
Separated by activated alumina cam chromatography using 2 as the developing solution,
Take the st fraction. The solvent was distilled off, and 1 part thereof was dissolved in acetonitrile at room temperature, and the resulting crystals were used as seeds.
Crystallization from acetonitrile gave the title compound N, N, N ', N'-tetrakis (3-tolyl) -5-methyl-1,3-phenylenediamine (Compound 1 of the invention). The reaction in the above-mentioned synthesis step complies with the above-mentioned series of reaction formulas [A].

 The elemental analysis results of this compound are shown below.

C ₃₅ H ₃₄ N ₂ as an experimental value H: 7.13%, C: 87.08 %, N: 5.83% Calculated H: 7.10%, C: 87.10 %, N: 5.80% The melting point of this compound 156-157 ° C. Met.

Second Synthesis Example (Synthesis of N, N, N ', N'-tetrakis (3-tolyl) -5-methoxy-1,3-phenylenediamine) 5-methylresorcinol (orcin In the same manner as in the above-mentioned first synthetic example, except that 12.3 g of 5-methoxyresorcinol was used instead of)), N, N'-bis (3-tolyl) -5-methoxy-1,3-phenylenediamine was obtained. . This N, N'-bis (3-tolyl) -5-methoxy-1,3-phenylenediamine 15.9 g and iodotoluene 21.8 g were added in the presence of potassium carbonate 9.7 g and copper powder 2 g.
It was added to 100 ml of nitrobenzene and refluxed for 24 hours for reaction. Hereinafter, in the same manner as in the first synthesis example, the title compound N, N,
N ', N'-tetrakis (3-tolyl) -5-methoxy-
1,3-Phenylenediamine (Compound 2 of the invention) was obtained.
The melting point of this compound was 169 to 170 ° C.

Third Synthesis Example (Synthesis of N, N, N ′, N′-tetrakis (3-tolyl) -5-allyl-1,3-phenylenediamine) 5-methylresorcinol (orcin ) Was used in place of 13.2 g of 5-allylresorcinol, and N, N'-bis (3
-Tolyl) -5-allyl-1,3-phenylenediamine was obtained. This N, N'-bis (3-tolyl) -5-allyl-
1,3-Phenylenediamine 16.4 g and iodotoluene 21.8 g
And were added to 100 ml of nitrobenzene in the presence of 9.7 g of potassium carbonate and 2 g of copper powder, and the mixture was refluxed for 24 hours for reaction. Less than,
The title compound N, N, N ′, N′− was prepared in the same manner as in the first synthesis example.
Tetrakis (3-tolyl) -5-allyl-1,3-phenylenediamine (inventive compound 3) was obtained. The melting point of this compound was 128-129 ° C.

Fourth Synthesis Example (Synthesis of N, N, N ′, N′-tetrakis (3-tolyl) -5-phenyl-1,3-phenylenediamine) 5-methylresorcinol (orcin ) Was used in the same manner as in the first synthesis example described above, except that 16.4 g of 5-phenylresorcinol was used to obtain N, N'-bis (3-tolyl) -5-phenyl-1,3-phenylenediamine. . This N, N′-bis (3-tolyl) -5-phenyl-1,3-phenylenediamine 18.2 g and iodotoluene 21.8 g were added in the presence of potassium carbonate 9.7 g and copper powder 2 g,
The mixture was added to 100 ml of nitrobenzene and refluxed for 24 hours for reaction. Hereinafter, in the same manner as in the first synthesis example, the title compound N, N,
N ', N'-tetrakis (3-tolyl) -5-phenyl-
1,3-Phenylenediamine (Compound 4 of the invention) was obtained.
The melting point of this compound was 176 to 177 ° C.

(2) Preparation of Electrophotographic Photoreceptor Preparation of Single-Layer Electrophotographic Photoreceptor N, N′-di (3,5-dimethylphenyl) perylene-3,4,9,10-tetracarboxydiimide 8 as charge generating material
Parts by weight, 100 parts by weight of the compound of the present invention synthesized in Synthesis Examples 1 to 4 as the charge transport material, and poly- as the binder resin.
100 parts by weight of (4,4'-cyclohexyldendiphenyl) carbonate (polycarbonate Z200 manufactured by Mitsubishi Gas Chemical Co., Inc.) and a predetermined amount of tetrahydrofuran are combined and dispersed by an ultrasonic disperser, and applied for a single-layer type photosensitive layer. A liquid was prepared. This coating solution is applied on an aluminum tube with an outer diameter of 78 mm and a length of 340 mm, then it is heated and dried at 100 ° C for 30 minutes in the dark, and a drum-type electrophotography having a single-layer photosensitive layer with a thickness of 24 μm A photoconductor was created.

Preparation of Laminated Electrophotographic Photosensitive Material 100 parts by weight of polyvinyl butyral (manufactured by Sekisui Chemical Co., Ltd., trade name Esretta BL1) as a binder resin, 100 parts by weight of oxotitanyl phthalocyanine as a charge generating material, and a predetermined amount of tetrahydrofuran in a ball mill. Preparation, 24
A charge generation layer coating solution is prepared by stirring and mixing for a period of time, and the prepared solution is applied to an aluminum drum by a dipping method.
A film thickness of 0.5 is obtained by curing with hot air drying at 0 ° C for 30 minutes.
A charge generation layer of μm was formed.

Then, 100 parts by weight of a polycarbonate resin (trade name: Iupilon, manufactured by Mitsubishi Gas Chemical Co., Inc.) as a binder resin, 100 parts by weight of each compound synthesized in the above Synthesis Examples 1 to 4 as a charge transport layer, and a predetermined amount of toluene. Was mixed by stirring with a homomixer to prepare a charge transport layer coating. This coating solution is applied to the surface of the charge generation layer by a dipping method,
A charge transport layer having a film thickness of about 20 μm was formed by drying with hot air at 0 ° C. for 30 minutes to prepare a laminated electrophotographic photoreceptor.

Comparative Example (N, N, N ′, N′-tetrakis (3
-Tolyl) -1,3-phenylenediamine Single-layer type and multi-layer type electrophotographic photoconductors were prepared in the same manner as in the above Preparation Example except that 100 parts by weight was used.

(3) Evaluation of electrophotographic photoconductor Single-layer electrophotographic photoconductor (measurement of initial surface potential V _SP ) Each of the above single-layer electrophotographic photoconductors was subjected to an electrostatic copying tester (Gentec Cynthia 30M manufactured by Gentec). ), The surface potential of each photoconductor whose surface is positively charged.
V _SP (V) was measured.

(Measurement of half-dose exposure amount and residual potential) Each of the electrophotographic photoconductors in the charged state was set to a halogen lamp (exposure intensity 0.92
mW / cm ² ) was used for exposure, the time until the surface potential V _SP became 1/2 was calculated, and the half-exposure amount E _1/2 (μJ / cm ² ) was calculated.

Further, the surface potential after 0.15 seconds has elapsed from the start of the exposure is _defined as the residual potential V _rp (V).

Laminated electrophotographic photoreceptor Monochromatic light obtained by passing Xe lamp light through a spectroscope as an exposure light source (λ = 780 nm, exposure intensity = 10 μW / cm ² , exposure time = 1
Second) to expose each laminated electrophotographic photoreceptor, and after exposure
The surface potential after 0.5 second was measured as the residual potential V _rp . Others were measured in the same manner as in the case of the single-layer type electrophotographic photosensitive member.

Tables 1 and 2 show the measurement results of the charging characteristics and the photosensitive characteristics of the electrophotographic photosensitive members obtained in the above Examples and Comparative Examples.

In Tables 1 and 2, “Before exposure” is the initial characteristic before light irradiation, and “After exposure” is the characteristic after irradiation with white light containing 400 lux of ultraviolet light for 40 minutes using a white fluorescent lamp. Show.

As shown in Tables 1 and 2 above, all the photoreceptors using the compound for charge transport material of the present invention have an initial surface potential V
It can be seen that the values of _SP , half-exposure amount E _1/2 , and residual potential V _rp before and after exposure are smaller than those of the comparative example, and the stability to light is excellent.

[Advantages of the Invention] As described above, the compound for a charge transport material of the present invention is excellent in photostability because it protects the central benzene ring by substituting the 5-position with a predetermined substituent. By using the charge transport material, an electrophotographic photoreceptor having excellent light stability can be obtained.

Claims (2)

[Claims] 1. The following general formula [I]: (In the formula, R ¹ , R ² , R ³ and R ⁴ are the same or different and each represents an alkyl group, an alkoxyl group, a halogen atom, an amino group, N-
It shows a substituted amino group, l, m, o and p are the same or different and each represents an integer of 0 to ⁵ , and R ⁵ represents an alkyl group, an alkoxyl group, an amino group, an allyl group or an aryl group. ) An m-phenylenediamine compound represented by 2. An electrophotographic photoreceptor comprising a conductive layer and a photosensitive layer containing the m-phenylenediamine compound according to claim 1 provided on the conductive substrate.