JPH0948758A - 2-hydroxy-3-phenylcarbamoyl-11h-benzo (a) carbazole compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a 2-hydroxy-3-phenylcarbamoyl 11H-benzo[a]carbazole compound which can be a source material for useful azo compounds as electric charge generating materials, etc., in the photosensitive body of a practical and high sensitive electrophotograph. SOLUTION: This 2-hydroxy-3-phenylcarbamoyl 11H-benzo[a]carbazole compound is expressed by formula I (Ar<1> and Ar<2> are each independently an aryl, etc.; X is H, an alkyl, etc.; Y is CH2 CH2 or CH=CH), e.g. the compound of formula II. The objective compound of formula I can be obtained by dissolving a 2-hydroxy-3-carboxy-11H-benzo[a]carbazole compound of formula III in an organic solvent, etc., such as benzene, etc., adding potassium hydroxide, etc., to the solution to obtain the carboxylic acid alkali salt, then, adding a halogenating agent such as phosphor pentachloride to bring the acid to an acid chloride and reacting the acid chloride with an aniline compound of formula IV.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound, and more specifically, a raw material for producing an azo compound useful as an organic photoconductor. As a 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

[0002]

2. Description of the Related Art Conventionally, it is known that a certain kind of azo compound is effective as a charge generating pigment used in a charge generating layer of a laminated type photoreceptor which is one form of an electrophotographic photoreceptor. The layered photoreceptor as used herein means a charge generating pigment having the ability to generate charge carriers by light on a conductive support by a suitable method such as vacuum deposition, coating a pigment solution, or coating a resin solution with a pigment. A charge generating layer is formed as a thin layer by applying a dispersion liquid in which the fine particles are dispersed, and the charge carriers generated in the charge generating layer are efficiently injected onto the charge generating layer, and the charge transporting layer (where This charge transport layer is usually a photoreceptor on which a charge transport material and a binder resin are formed. Conventionally, as an azo compound used for this type of photoreceptor, for example, JP-A-47-37543 and JP-A-52-55643.
Benzidine-based bisazo compounds described in JP-A-52-8832, stilbene-based bisazo compounds described in JP-A-52-8832, and the like are known.
However, conventional laminated type photoreceptors using azo compounds generally have low sensitivity and are not sufficient as photoreceptors for high-speed copying machines.

[0003]

The object of the present invention is to provide a novel compound 2 which is useful as a raw material for obtaining an azo compound which is useful in an electrophotographic photoreceptor, particularly in the above-mentioned laminated electrophotographic photoreceptor. -Hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

[0004]

According to the present invention, there is provided a 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound represented by the following general formula (I).

Embedded image (In the formula, Ar ¹ and Ar ² represent a substituted or unsubstituted aryl group, which may be the same or different, X is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and Y is —CH ₂ CH ₂ -Or- represents CH = CH-.)

2- represented by the above general formula (I) of the present invention
The hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound includes an aniline compound represented by the following general formula (II) and 2-hydroxy-3-carboxy-11H represented by the following general formula (III). It can be obtained by reacting with a benzo [a] carbazole compound.

Embedded image (In the formula, Ar ¹ and Ar ² represent a substituted or unsubstituted aryl group, and may be the same or different. Y is —C.
H ₂ CH ₂ - or represents a -CH = CH-. )

Embedded image (In the formula, X represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom.)

BEST MODE FOR CARRYING OUT THE INVENTION

2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] represented by the general formula (I)
The production of a carbazole compound is specifically carried out by using benzene,
The 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound represented by the general formula (III) is dissolved or dispersed in an organic solvent such as toluene or dioxane, and potassium hydroxide, Isolate the acid halide by adding an alkali metal hydroxide such as sodium hydroxide to form a carboxylic acid alkali metal salt, and then adding a halogenating agent such as phosphorus pentachloride, phosphorus trichloride, or thionyl chloride. Alternatively, it can be obtained by reacting with the aniline compound represented by the general formula (II) as it is.

Specific examples of Ar ¹ , Ar ² and X in the above general formulas (I), (II) and (III) include aryl groups such as phenyl group, biphenylyl group, naphthyl group, anthryl group and pyrenyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group, an alkoxy group includes a methoxy group, an ethoxy group, a propoxy group and a butoxy group, and a halogen atom includes fluorine, chlorine, bromine and iodine. . Examples of the substituent of Ar ¹ and Ar ² include the above aryl group, alkyl group, alkoxy group and halogen atom.

[0008]

EXAMPLES Examples and applications will be shown below, but the present invention is not limited thereto.

Example 1 13.86 g (50.0 mmol) of 2-hydroxy-3-carboxy-11H-benzo [a] carbazole
Dispersed in 140 ml of 1,4-dioxane and added to this
After adding a solution of 6% potassium hydroxide (3.26 g, 50.0 mmol) and methanol (10 ml), the mixture was heated and stirred until the temperature reached about 90 ° C. over 2 hours while distilling the solvent off. After adding 80 ml of 1,4-dioxane,
4.53 g of phosphorus trichloride (33.0 mmo at about 80 ° C)
1) a solution prepared by diluting 1) with 5 ml of 1,4-dioxane.
The mixture was added dropwise over 5 minutes, and the mixture was stirred under reflux for 1 hour. 4-
A solution of 19.63 g (50.0 mmol) of (4-aminophenethyl) -4 ′, 4 ″ -dimethyltriphenylamine and 30 ml of 1,4-dioxane was added dropwise over 15 minutes, and the mixture was further stirred under reflux for 11 hours. The contents were left to cool to room temperature, opened in ice water and neutralized with sodium carbonate. The generated precipitate was separated by filtration, washed with water, then with methanol, and dried by heating under reduced pressure to obtain light brown yellow crude crystals. Further, this was subjected to silica gel column chromatography treatment (eluent: toluene / ethyl acetate = 3/1 (volume ratio)) and then recrystallized with a mixed solvent of N, N-dimethylformamide / ethanol to give yellow needle crystals. 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] of the target compound represented by the following structural formula (IV)
A carbazole compound (10.90 g, yield 33.4%) was obtained. Melting point was 289 ° C. This 2-hydroxy-
Infrared absorption spectrum of 3-phenylcarbamoyl-11H-benzo [a] carbazole compound (KBr tablet method)
Is shown in FIG.

Embedded image

Example 2 2 represented by the following structural formula (V) under the same conditions as in Example 1
-Hydroxy-3-phenyl-carbamoyl-11H-
A benzo [a] carbazole compound was obtained with a yield of 24%.

Embedded image The melting point was 280 ° C. or higher. This 2-hydroxy-3
The infrared absorption spectrum (KBr tablet method) of the -phenylcarbamoyl-11H-benzo [a] carbazole compound is shown in Fig. 2.

Examples 3 to 5 Under the same conditions as in Example 1, 2-hydroxy-3-phenylcarbamoyl-11H- each represented by the following structural formulas:
Benzo [a] carbazole compound [(VI) (Example 3),
(VII) (Example 4), (VIII) (Example 5)] were obtained. Table 1 shows the yield, melting point, and elemental analysis values of the obtained compound.
Further, the infrared absorption spectrum diagrams (KBr tablet method) of the obtained 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compounds are respectively shown in FIG.
Are shown in FIGS.

[Chemical 6]

[Chemical 7]

Embedded image

[0012]

[Table 1]

Application Example The 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound represented by the structural formula (IV) obtained in Example 1 was added to triphenylamine-4,
By reacting 4 ′, 4 ″ -tris (diazonium tetrafluoroborate), a trisazo compound represented by the following structural formula (IX) was produced.

Embedded image

Next, 7.5 parts by weight of this trisazo compound and a solution of a polyester resin (Vylon 200 manufactured by Toyobo Co., Ltd.) in tetrahydrofuran (solid concentration 0.5% by weight) 5
00 parts by weight are pulverized and mixed in a ball mill, and the obtained dispersion is applied on the aluminum surface of an aluminum vapor-deposited polyester base (conductive support) using a doctor blade, and naturally dried to a thickness of about 1 μm. The charge generation layer of was formed. On this charge generating layer, 1 part by weight of 4'-bis (4-methylphenyl) -α-phenylstilbene as a charge transport material, 1 part by weight of a polycarbonate resin (Panlite K-1300 manufactured by Teijin Ltd.) and 8 parts by weight of tetrahydrofuran. The solution obtained by mixing and dissolving is mixed with 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 to form a laminated electrophotographic photoreceptor. did.

The laminated electrophotographic photosensitive member produced as described above was subjected to negative corona discharge of -6 KV for 20 seconds using an electrostatic copying paper tester (SP428 type manufactured by Kawaguchi Electric Co., Ltd.). After being charged to, the sample was left in a dark place for 20 seconds, and the surface potential Vpo (V) at that time was measured.
The light is irradiated so that it becomes lux, and the light is attenuated to Vpo.
Then, the time (sec) until the value becomes 1/2 was calculated, and the half-exposure amount E1 / 2 (lux · sec) was calculated as the sensitivity of the photoconductor. Vpo is -1144 (V), E1 / 2 is 2.5
It is 1 (lux · sec), which shows that the electrophotographic photosensitive member has high sensitivity.

[0016]

INDUSTRIAL APPLICABILITY As described above, the 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound of the present invention is novel, can be easily produced, and is clear from the application examples. It is extremely useful as a raw material for producing an azo compound which is a charge generating substance in a high-sensitivity electrophotographic photosensitive member practical for a high speed copying machine.

[Brief description of drawings]

1 shows the 2-hydroxy-form of the present invention obtained in Example 1. FIG.
FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of a 3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

2 is the 2-hydroxy-form of the present invention obtained in Example 2. FIG.
FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of a 3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

FIG. 3 shows the 2-hydroxy-form of the present invention obtained in Example 3.
FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of a 3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

FIG. 4 is the 2-hydroxy-form of the present invention obtained in Example 4.
FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of a 3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

FIG. 5: 2-hydroxy- of the present invention obtained in Example 5
FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of a 3-phenylcarbamoyl-11H-benzo [a] carbazole compound.

Claims (1)

[Claims] 1. A 2-hydroxy-3-phenylcarbamoyl-11H-benzo [a] carbazole compound represented by the following general formula (I). Embedded image (In the formula, Ar ¹ and Ar ² represent a substituted or unsubstituted aryl group, which may be the same or different, X is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and Y is —CH ₂ CH ₂ -Or- represents CH = CH-.)