JP2008063224A - Bisazo compound, 2-hydroxy-3-phenylcarbamoylnaphthalene compound, aniline compound, manufacturing method of bisazo compound, photoreceptor, image-forming device and process cartridge - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a bisazo compound useful for a laminated photoreceptor of an electrophotographic photoreceptor, a 2-hydroxy-3-phenylcarbamoylnaphthalene compound, an aniline compound, a manufacturing method of the bisazo compound, a photoreceptor, an image-forming device and a process cartridge. <P>SOLUTION: The bisazo compound is represented by general formula [A]. The bisazo compound is used as a photosensitive material of an electrophotographic photoreceptor. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a bisazo compound, and to a novel aniline compound and a novel 2-hydroxy-3-phenylcarbamoylnaphthalene compound which are intermediates for the production thereof. More particularly, it relates to a bisazo compound useful as an organic photoconductor. The present invention also relates to a photoreceptor, an image forming apparatus, and a process cartridge having such a bisazo compound.

  Conventionally, it is known that a certain azo compound is effective as a charge generation pigment used in a charge generation layer of a multilayer photoreceptor. The term “layered photoreceptor” as used herein refers to a photoreceptor used for an electrophotographic photoreceptor, and a charge generating pigment having an ability to generate charge carriers by light is applied to a suitable support (for example, a vacuum) on a conductive support. A charge generation layer is formed as a thin layer by vapor deposition, application of a pigment solution, or application of a dispersion liquid in which fine particles of pigment are dispersed in a resin solution, and charge carriers generated in the charge generation layer are efficiently formed thereon. It is a photoreceptor formed by laminating a charge transport layer (which is usually made of a charge transport material and a binder resin) which is injected and moves.

As azo compounds used in this type of photoreceptor, for example, benzidine bisazo compounds described in Patent Document 1 and Patent Document 2, or stilbene bisazo compounds described in Patent Document 3 are known. It has been.
However, a conventional multilayer type photoreceptor using an azo compound is generally insufficient in sensitivity, so that it is insufficient as a photoreceptor for a high-speed copying machine. Thus, a bisazo compound to which a hole transporting charge substance is bound, which is described in Patent Document 4 which attempts to improve this problem, is known. However, further enhancement of sensitivity is necessary.
JP 47-37543 A JP 52-55643 A JP-A-52-8834 JP-A-8-209007

The present invention provides a bisazo compound represented by the following formula [A], a 2-hydroxy-3-phenylcarbamoylnaphthalene compound, an aniline compound, a method for producing a bisazo compound, a photoreceptor, an image forming apparatus, and a process cartridge. It is an object.

The invention described in claim 1 is a bisazo compound represented by the following general formula [A].

The invention according to claim 2 is a bisazo compound represented by the following general formula [I].

The invention described in claim 3 is a 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the following general formula [II].

請求項５に記載の発明は、ビスアゾ化合物の製造方法の製造方法であって、下記式［Ｖ］で表されるビス（ジアゾニウム塩）化合物と、請求項３に記載の２−ヒドロキシ−３−フェニルカルバモイルナフタレン化合物［ＩＩ］または下記式［ＶＩ］の２−ヒドロキシ−３−フェニルカルバモイルナフタレン化合物とのいずれかの前記フェニルカルバモイルナフタレン化合物との反応物に、残りの前記フェニルカルバモイルナフタレン化合物［ＩＩ］または［ＶＩ］を反応させることを特徴とする。

The invention according to claim 4 is an aniline compound represented by the following general formula [III].

Invention of Claim 5 is a manufacturing method of the manufacturing method of a bisazo compound, Comprising: The bis (diazonium salt) compound represented by following formula [V], 2-hydroxy-3- of Claim 3 The remaining phenylcarbamoylnaphthalene compound [II] is reacted with the phenylcarbamoylnaphthalene compound [II] or 2-hydroxy-3-phenylcarbamoylnaphthalene compound of the following formula [VI] with any of the phenylcarbamoylnaphthalene compounds. Alternatively, [VI] is reacted.

  The invention described in claim 6 is characterized in that the bisazo compound described in claim 1 or 2 is used as a photosensitive material of an electrophotographic photosensitive member.

  The invention described in claim 7 is the bisazo compound according to claim 6, wherein the photosensitive material is an organic light guide.

  The invention according to claim 8 is an electrophotographic photoreceptor having the compound according to claim 1 or 2 in a charge generation layer.

  A ninth aspect of the invention is an image forming apparatus having the photosensitive drum of the eighth aspect.

  According to a tenth aspect of the present invention, there is provided a process cartridge having at least a photosensitive drum and a developing device, wherein the photosensitive drum is detachably formed on a main body of the image forming apparatus, and the photosensitive drum is a photosensitive member according to the eighth aspect. It is characterized by being a drum.

  The novel aniline compound, 2-hydroxy-3-phenylcarbamoylnaphthalene compound and bisazo compound of the present invention can be easily produced. The bisazo compound of the present invention is extremely useful as a charge generating material in a substantially high-sensitivity electrophotographic photosensitive member for a high-speed copying machine.

  The present embodiment is useful in electrophotographic photoreceptors, particularly in bisazo compounds useful in the above-mentioned multilayer photoreceptors, and novel aniline compounds and novel 2-hydroxy-3s that are intermediates for producing the bisazo compounds. -To provide a phenylcarbamoylnaphthalene compound, to apply the compound to a photoreceptor, and to provide an image forming apparatus having the photoreceptor.

  As a result of intensive studies, the present inventors synthesized a novel aniline compound, synthesized a novel 2-hydroxy-3-phenylcarbamoylnaphthalene compound and an aniline compound from the synthesized aniline compound, and used these intermediates to produce a novel aniline compound. By synthesizing a bisazo compound, it was found that the above-mentioned problems were achieved, and the present invention was completed.

  That is, according to the present embodiment, bisazo compounds represented by the following general formulas [A] and [I] are provided, and also represented by the following general formula [II], which is an intermediate for producing the bisazo compounds. 2-Hydroxy-3-phenylcarbamoylnaphthalene compounds are provided.

In the above formulas [A], [I] and [II], R ₁ represents a linear or branched alkyl group, and R ₂ represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group or a dialkylamino. Represents a group, n represents an integer, and when n is an integer of 2 or more, R ₂ may be the same group or different groups.

  Moreover, according to this embodiment, an aniline compound represented by the following general formula [III] is provided.

  Moreover, the manufacturing method of the bisazo compound of this embodiment is the bis (diazonium salt) compound represented by the following formula [V], the above-mentioned 2-hydroxy-3-phenylcarbamoylnaphthalene compound [II], or the following formula [VI]. The remaining phenylcarbamoylnaphthalene compound [II] or [VI] is reacted with the reaction product with the 2-hydroxy-3-phenylcarbamoylnaphthalene compound described in 1.

  The compounds [A] and [I] of the present embodiment are preferably photosensitive materials for electrophotographic photoreceptors, particularly organic photoconductors, and these compounds are contained in the charge generation layer of the photoreceptor for electrophotography. It is preferable to have. An image forming apparatus and a process cartridge having such a photosensitive drum are preferable.

Hereinafter, the invention of the bisazo compound of the present embodiment will be described.
The bisazo compound and 2-hydroxy-3-phenylcarbamoylnaphthalene compound of the present embodiment are represented by the following general formulas [A], [I] (above bisazo compounds) and [II].

In the above formulas [A], [I] and [II], R ₁ represents a linear or branched alkyl group, and R ₂ represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group or a dialkylamino. Represents a group, n represents an integer, and when n is an integer of 2 or more, R ₂ may be the same group or different groups.

Examples of the linear or branched alkyl group represented by R ₁ include an optionally branched alkyl group having 1 to 100 carbon atoms, preferably 1 to 50 carbon atoms (for example, 1 to 20 carbon atoms). The alkyl group which may be branched is mentioned. Examples of the substituent of such an alkyl group include an alkoxy group, a halogen atom, a nitro group or a dialkylamino group, and an aryl group. Specifically, the alkoxy group includes an alkoxy group having 1 to 4 carbon atoms, the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the dialkylamino group includes a dimethylamino group. , An amino group having two alkyl groups having about 1 to 8 carbon atoms such as a diethylamino group, a dipropylamino group, and a dibutylamino group (however, the two alkyl groups may be the same or different), and an aryl group Examples thereof include a phenyl group, a benzyl group, and a biphenylyl group.

Examples of the aromatic hydrocarbon group for R ₁ include a phenyl group, a benzyl group, a biphenylyl group, a naphthyl group, an anthryl group, and a pyrenyl group.

  The bisazo compound [A] of the present embodiment and one of the compounds represented by the formula [I] include a 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the general formula [II] and bis (diazonium ) Obtained by reacting with a salt compound or the like. Further, the 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the formula [II] includes an aniline compound represented by the following general formula [III] and a 2-hydroxy-3 represented by the following formula [IV]. It can be obtained by reacting with naphthoic acid. First, a method for producing a 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the formula [II] will be described.

  The 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the general formula [II] of the present embodiment includes an aniline compound represented by the following general formula [III] and a 2-hydroxy compound represented by the following formula [IV]. It can be obtained by reacting with hydroxy-3-naphthoic acid.

Wherein [III], R ₁ is the formula [A], the same meaning as R ₁ in [I].
The 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the general formula [II] is represented by the formula [IV] represented by an aromatic solvent such as benzene or toluene or an organic solvent such as dioxane. -Hydroxy-3-naphthoic acid is dissolved or dispersed, and a halogenating agent such as phosphorus pentachloride, phosphorus trichloride, thionyl chloride is added thereto to form an acid halogen compound [IV '], which is isolated (2 -Hydroxy-3-naphthoic acid halide [IV ′]) or directly reacted with an aniline compound represented by the above general formula [III].

  The bisazo compounds represented by the general formulas [A] and [I] of the present embodiment are useful as charge generating materials for laminated electrophotographic photoreceptors as described above. Furthermore, these bisazo compounds of this embodiment are also useful as a charge generation material in an electrophotographic photosensitive member having a single-layer type photosensitive layer in which a charge generation material and a charge transport material are dispersed in a resin. It is also useful as a photoconductive substance in an electrophotographic photoreceptor having a photosensitive layer in which a photoconductive substance is dispersed.

  The production method of the bisazo compound represented by the general formulas [A] and [I] of the present embodiment will be described. The bisazo compound represented by the general formulas [A] and [I] of the present embodiment is A bis (diazonium salt) compound represented by the following general formula [V] and a 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the above general formula [II] or 2 represented by the following general formula [VI] A reaction in which -hydroxy-3-phenylcarbamoylnaphthalene compound is sequentially reacted in two steps (production method 1: sequential reaction method without isolation), or the following general formula [VII] or [VIII] obtained by the first coupling reaction And then reacting the corresponding 2-hydroxy-3-phenylcarbamoylnaphthalene compound with each other. Reaction either to: obtained by (Process 2 isolation procedure).

In the formula, R ₂ has the same meaning as in the above formula [II].

Wherein [VII] and the formula [VIII], R ₁ and R ₂ represent the same group as R ₁ and R ₂ in the formula [A], X ^- represents an anion functional group.

  The bisazo compound represented by the above general formula [A] or [I] is used in the first-stage coupling reaction in an organic solvent such as N, N-dimethylformamide (DMF) or dimethyl sulfoxide (DMSO). A 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the formula [VI] is dissolved, a bis (diazonium salt) compound represented by the general formula [V] is added thereto, and sodium acetate is added if necessary. By adding a basic substance such as an aqueous solution or organic amine, the first-stage coupling reaction is completed. The reaction temperature at this time is preferably in the range of about -20 ° C to about 40 ° C.

  In the second-stage coupling reaction, 2-hydroxy-3 represented by the above general formula [II], which is different from that used in the first-stage coupling reaction, is added to the reaction mixture obtained above. -Add further phenylcarbamoylnaphthalene compound and, as in the first-stage coupling reaction, complete by adding a basic substance such as aqueous sodium acetate or organic amine, if necessary, or the first-stage cup If necessary, an acid aqueous solution such as water or dilute hydrochloric acid is added to the ring reaction mixture (at this time, cooling is sufficiently performed so as not to decompose the diazonium salt compound of the general formula [VII] or [VIII] generated by the reaction. Preferably at a temperature of 10 ° C. or lower), and a divalent compound of the general formula [VII] or [VIII]. The zonium salt compound is separated by filtration and isolated as shown in Preparation Method 2, and this diazonium chloride is represented by a general formula [II] or [VI] different from that used in the first-stage coupling reaction. The reaction is completed by reacting the -hydroxy-3-phenylcarbamoylnaphthalene compound in the same manner as the first-stage coupling reaction.

  In any reaction mixture obtained by any of the methods, the crystals precipitated after the completion of the reaction are filtered off and purified by an appropriate method (for example, by washing with water and / or an organic solvent and recrystallizing. Etc.) to produce the bisazo compounds of the above general formulas [A] and [I].

は、アニオン官能基（アニオン基）を表す（文章中には「Ｘ^-」と表記）が、例えばテトラフルオロボレート（BF₄ ^-）、パークロレート（ClO₄ ^-）、ヨーデイド（I^-）、クロライド（Cl^-）、ブロマイド（Br^-）、サルフェート（SO₃ ^-）、ヘキサフルオロホスフェート（PF₆ ^-）、ヘキサフルオロアンチモネート（SbF₆ ^-）、パーヨーデイド（IO₄ ^-）、ｐ−トルエンスルホネート等が好ましい。 More specific examples of the substituents for R ₁ and R _{2 in} the general formulas [A] and [I] to [VIII] include a methyl group, an ethyl group, a propyl group, a butyl group, a heptyl group as an alkyl group, 2-methylheptyl group as alkoxy group, methoxy group, ethoxy group, propoxy group, butoxy group as halogen atom, fluorine atom, chlorine atom, bromine atom and iodine atom as aryl group, phenyl group, biphenyl group, naphthyl group as aryl group , Anthryl group, pyrenyl group and the like. In the general formulas [V], [VII] and [VIII]

Represents an anionic functional group (anionic group) (indicated as “X ⁻ ” in the text), for example, tetrafluoroborate (BF ₄ ⁻ ), perchlorate (ClO ₄ ⁻ ), iodoide (I ⁻ ), chloride (Cl ⁻ ), bromide (Br ⁻ ), sulfate (SO ₃ ⁻ ), hexafluorophosphate (PF ₆ ⁻ ), hexafluoroantimonate (SbF ₆ ⁻ ), periodate (IO ₄ ⁻ ), p-toluenesulfonate, etc. preferable.

  The bisazo compound [A] of this embodiment, for example, [I], is an electrophotography in which a latent image obtained by exposing an image on a uniformly charged photoreceptor is developed with toner. It can be used for a photoconductor of the type. In such a photoreceptor, a photosensitive layer having a charge generation layer and a charge transport layer is provided on a conductive support directly or via an undercoat layer. The charge generation layer of such a photoreceptor can have the bisazo compounds [A] and [I] of this embodiment. An image forming apparatus having such a photoreceptor is also included in this embodiment. In such an image forming apparatus, at least the bisazo compound [A], for example, a photosensitive member having a compound represented by [I], is formed into a drum-like photosensitive drum, and the photosensitive drum is charged. Charging device, optical scanning means for forming a latent image on the surface of the photosensitive drum uniformly charged by the charging device, a developing device for developing the obtained latent image with toner, and The image forming apparatus includes a transfer unit that transfers the developed image onto a thin layer medium such as paper, and a fixing unit that fixes the transferred development and the thin layer medium. Further, a cleaner for cleaning the surface of the photosensitive drum after transfer can be provided. It should be noted that at least the photosensitive drum and the developing device may be provided as a cartridge body, and the cartridge body may further include the cleaner. Such a cartridge body can be a process cartridge configured to be detachable from the image forming apparatus main body.

  Hereinafter, the present embodiment will be described in more detail with reference to examples. However, the present embodiment is not construed to be limited to these examples, and the present embodiment is shown in the scope disclosed in the specification and the like. Has been.

[Example]
The 2-hydroxy-3-phenylcarbamoylnaphthalene compound of this embodiment and the bisazo compound produced as an intermediate thereof can be easily produced according to the above description. Further, in order to clarify that the bisazo compound of the present embodiment is an effective material in the electrophotographic photoreceptor, the following examples and application examples are shown, but the present embodiment is not limited to this example. .

[Production Example 1]
26.8 g (100 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 150 ml of dehydrated dimethylformaldehyde were mixed and stirred under reflux in an argon gas atmosphere. After 30 minutes, a solution of 11.5 g (100 mmol) of 2-heptylamine diluted with 50 ml of dehydrated dimethylformaldehyde was added dropwise over 30 minutes, and the mixture was refluxed and stirred for 12 hours. After cooling to room temperature, the mixture was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene / ethyl acetate mixed solvent) and concentrated under reduced pressure to obtain 17.5 g of a monoimide compound of the following structural formula [1] (yield: 48. 0%). The melting point of the obtained monoimide compound was 183.0 to 184.0 ° C.

  The infrared absorption spectrum (KBr tablet method) of the monoimide compound of the above structural formula [1] is shown in FIG. The elemental analysis values are shown in Table 1.

[Example 1]
(Synthesis of aniline compounds)
14.6 g (40 mmol) of the monoimide represented by the above structural formula [1], 5.5 g (40 mmol) of 2- (4-aminophenyl) ethylamine, and 200 ml of dimethylformaldehyde were mixed and stirred at reflux for 2 hours. After cooling to room temperature, the mixture was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene / ethyl acetate = 9/1, volume ratio), concentrated under reduced pressure, and 14.0 g (72.5 g) of an aniline compound of the following structural formula [2]. %)Obtained. The melting point was 182.5-183.5 ° C.

  FIG. 2 shows an infrared absorption spectrum (KBr tablet method) of the aniline compound represented by the structural formula [2]. The elemental analysis values are shown in Table 1.

[Example 2]
(Synthesis example of 2-hydroxy-3-phenylcarbamoylnaphthalene compound)
1.88 g (10 mmol) of 2-hydroxy-3-naphthoic acid and 4.83 g (10 mmol) of the aniline compound represented by the above structural formula [2] are dissolved in 25 ml of 1,4-dioxane, and trichloride is obtained at room temperature. A solution obtained by diluting 1.37 g (10 mmol) of phosphorus with 5 ml of 1,4-dioxane was added dropwise over 10 minutes, followed by stirring under reflux for 5 hours. After cooling to room temperature, it was dropped into ice water and neutralized with sodium carbonate. The formed precipitate was separated by filtration, washed with water, then washed with methanol, and dried under reduced pressure to obtain 6.21 g of light brown crude crystals (yield 95.0%). Further, this was purified by silica gel column chromatography (developing solvent: tetrahydrafuran), concentrated under reduced pressure and recrystallized with a mixed solvent of dimethylformaldehyde / ethanol to give 2-hydroxy- 5.0 g (yield 76.5%) of 3-phenylcarbamoylnaphthalene compound was obtained. The melting point was 280 ° C. or higher.

  FIG. 3 shows an infrared absorption spectrum (KBr tablet method) of the 2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the above structural formula [3]. The elemental analysis values are shown in Table 1.

[Example 3]
(Synthesis example of bisazo compound)
2.233 g (7.5 mmol) of 2-hydroxy-3- (2-chlorophenyl) carbamoylnaphthalene is dissolved in 300 ml of dimethylformaldehyde and 3.058 g of 9-fluorene-2,7-bisdiazonium bistetrafluoroborate at room temperature (7 0.5 mmol) was added. After stirring at room temperature for 10 minutes, a solution prepared by dissolving 4.903 g (7.5 mmol) of the 2-hydroxy-3-phenylcarbamoylnaphthalene compound of the above structural formula [3] in 300 ml of dimethylformaldehyde was added. What dissolved 4.082 g (30 mmol) of hydrates in 25 ml of water was dripped over 20 minutes, and it stirred at room temperature for 2 hours. The resulting precipitate was filtered off and washed three times with 600 ml of dimethylformaldehyde heated to 80 ° C. and then twice with 600 ml of water. It dried under reduced pressure at 120 degreeC and obtained 6.61 g (yield 74.0%) of the bisazo compound of following Structural formula [4]. The melting point was 280 ° C. or higher.

  FIG. 4 shows an infrared absorption spectrum (KBr tablet method) of the bisazo compound of the structural formula [4]. The elemental analysis values are shown in Table 1.

[Application Example 1]
7.5 parts by weight of the bisazo compound of the structural formula [4] obtained in Example 4 and 500 parts by weight of a tetrahydrofuran solution (solid content concentration: 0.5% by weight) of a polyester resin (Byonbo Co., Ltd. Byron 200) The resulting dispersion is applied onto the aluminum surface of a polyester base (conductive support) on which aluminum has been deposited using a doctor blade and dried naturally to form a charge generation layer having a thickness of about 1 μm. Formed.

  On this charge generation layer, 1 part by weight of 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline as a charge transport material, 1 part by weight of a polycarbonate resin (Tanjin Panlite K-1300) A solution in which 8 parts by weight of tetrahydrofuran and 8 parts by weight of tetrahydrofuran are mixed and dissolved is applied using a doctor blade and dried at 80 ° C. for 2 minutes and then at 120 ° C. for 5 minutes to form a charge transport layer having a thickness of about 20 μm. A photoconductor was prepared.

Next, the obtained photoconductor was charged by applying a corona discharge of about −6 KV for 20 seconds in the dark using an electrostatic copying paper test apparatus (EPA8100 type, manufactured by Kawaguchi Electric Co., Ltd.), and further charged with 20 The surface potential V0 (V: Volt) of the photoreceptor was measured by leaving it in a dark place for 2 seconds. Next, the tungsten lamp is irradiated with light so that the surface has an illuminance of 4.5 lux, and the time (sec) until V0 becomes ½ due to light attenuation is obtained. 2 (lux / sec) was determined.
The results are shown in Table 2.

[Application 2]
A photoconductor was prepared and measured in the same manner as in Application Example 1 except that 4′-diphenylamino-α-phenylstilbene was used as the charge transport material. The results are shown in Table 2.

[Comparative Example 1]
A photoconductor was prepared and measured in the same manner as in Application Example 1 except that the bisazo compound of the following structural formula [5] was used as the charge generation material. The results are shown in Table 2.

An infrared absorption spectrum of monoimide compound obtained in Production Example 1 (KBr tablet method), the horizontal axis represents the wave number (cm ^-1), and the vertical axis represents the transmittance (%). It is an infrared absorption spectrum figure (KBr tablet method) of aniline compound [2] of this embodiment obtained in Example 1, a horizontal axis shows a wave number (cm ^<-1 >), and a vertical axis | shaft shows the transmittance | permeability (%). Indicates. It is an infrared absorption spectrum figure (KBr tablet method) of the 2-hydroxy-3-phenylcarbamoylnaphthalene compound [3] of the present embodiment obtained in Example 2, the horizontal axis indicates the wave number (cm ⁻¹ ), The vertical axis indicates the transmittance (%). It is an infrared absorption spectrum figure (KBr tablet method) of the bisazo compound [4] of this embodiment obtained in Example 3, a horizontal axis shows a wave number (cm ^<-1 >), and a vertical axis | shaft shows the transmittance | permeability (%). Indicates.

Claims (10)

A bisazo compound represented by the following general formula [A].

A bisazo compound represented by the following general formula [I].

2-hydroxy-3-phenylcarbamoylnaphthalene compound represented by the following general formula [II].

An aniline compound represented by the following general formula [III].

A bis (diazonium salt) compound represented by the following formula [V] and 2-hydroxy-3-phenylcarbamoylnaphthalene compound [II] according to claim 3 or 2-hydroxy-3-phenyl of the following formula [VI] A method for producing a bisazo compound, comprising reacting any of the phenylcarbamoylnaphthalene compound with a carbamoylnaphthalene compound and the remaining phenylcarbamoylnaphthalene compound [II] or [VI].

  The bisazo compound according to claim 1, which is used as a photosensitive material for an electrophotographic photosensitive member.   The bisazo compound according to claim 6, wherein the photosensitive material is an organic photoconductor.   An electrophotographic photosensitive member comprising the compound according to claim 1 in a charge generation layer.   An image forming apparatus comprising the photosensitive drum according to claim 8.   9. A process cartridge including at least a photosensitive drum and a developing device, wherein the photosensitive drum is detachably formed on a main body of the image forming apparatus, and the photosensitive drum is a photosensitive drum according to claim 8. Process cartridge.

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