JPH0859615A - Carbazole compound and producing of the same - Google Patents

Abstract

PURPOSE: To obtain a new carbazole compound useful as an organic photoconductive material for electrophotographic material, capable of satisfying all requirements in an organic photoconductive material, a fluoresecent whitening agent, especially in the electronic photography. CONSTITUTION: N-(β-phenylstyryl-4-phenyl) carbazole of formula I. The compound of formula I is obtained by condensation-reacting a diphenyl compound of formula II [Y is triphenylphosphonium of formula III (Z is a halogen), dialkyl phosphite of the formula: PO(OR)2 (R is a lower alkyl)] with N-(4-formylphenyl) carbazole of formula IV.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a carbazole compound useful as an organic photoconductive material for electrophotography, a fluorescent brightening agent and the like, particularly as an organic photoconductive material, and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, many materials such as poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoconductors used in electrophotography. The "electrophotographic method" here generally refers to a photoconductive photoreceptor,
First, it is charged in a dark place by, for example, corona discharge, and then an electrostatic latent image is obtained by selectively discharging the electric charge only in the exposed portion, and this latent image portion is visualized by developing means with toner to form an image. This is one of the image forming methods. The basic characteristics required for a photoreceptor in such an electrophotographic system are as follows: 1) being charged to an appropriate potential in a dark place, 2) little discharge of charges in a dark place, and 3) irradiation with light. It is mentioned that the discharge of electric charge is carried out promptly. However, the conventional photoconductive organic material does not necessarily satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and among them, selenium is widely used in practice. However, recently, from the viewpoint of electrophotographic process, in addition to various requirements for the photoconductor, that is, in addition to the basic characteristics described above, for example, a belt-shaped photoconductor having a flexible shape is required. Is starting to appear. However, in the case of selenium, it is generally difficult to produce such a shape.

[0003]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel organic photoconductive material for electrophotography, a fluorescent brightening agent, etc., which is particularly useful as an organic photoconductive material capable of satisfying all the above requirements in electrophotography. A carbazole compound and a method for producing the same are provided.

[0004]

SUMMARY OF THE INVENTION

Embedded image N- (β-phenylstyryl-4-phenyl) carbazole represented by

A method for producing the carbazole compound of [Chemical Formula 1], that is,

Embedded image

[Outside 2] A triphenylphosphonium group or -PO (O
R) ₂ (wherein R represents a lower alkyl group) represents a dialkyl phosphite group. ] With a diphenyl compound represented by

[Chemical 3] Is condensed with N- (4-formylphenyl) carbazole represented by

Embedded image Is a method for producing N- (β-phenylstyryl-4-phenyl) carbazole.

The N- (β-phenylstyryl-4-phenyl) carbazole of [Chemical Formula 1] of the present invention is a novel compound and has the infrared spectrum of FIG.

This N- (β-phenylstyryl-4-phenyl) carbazole is produced by condensing the diphenyl compound of [Chemical Formula 2] and the N- (4-formylphenyl) carbazole compound of [Chemical Formula 3].

The diphenyl compound of [Chemical Formula 2] can be easily prepared by heating the corresponding halomethyl compound and trialkyl phosphite or triphenylphosphine directly or in a solvent such as toluene, tetrahydrofuran, N, N-dimethylformamide or the like. Manufactured to. Here, the trialkyl phosphite is preferably an alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group.

The N- (4-formylphenylcarbazole) of [Chemical Formula 3] can be easily produced by reduction of N- (4-cyanophenyl) carbazole. Here, as the reduction method, there are the following methods (1) and (2). (1) Stephen method [Organic Reactions
8 , 246 (1954)]: A reduction product (aldimine) obtained by adding a raw material nitrile to an anhydrous solvent suspension of anhydrous stannous chloride saturated with hydrogen chloride and reacting at room temperature with water or diluted sulfuric acid. Boil. Examples of the solvent used include ethers such as diethyl ether and diisopropyl ether; tetrahydrofuran; chloroform and the like. (2) Reduction method with metal hydrogen complex compound: The metal hydrogen complex compound and the raw material nitrile are reacted in an anhydrous solvent. As the metal-hydrogen complex compound, LiAlH ₄ [J. Am. Chem. Soc.,
86 , 1085 (1964)], LiAlH (OC ₂ H ₅ ) ₃ [J. Am.
Chem. Soc., 86 , 1079 (1964)], NaAlH (OC ₂ H
₅ ) ₃ [Liebigs Ann. Chem., 607 , 24 (1957)], LiA
_{lH (O-t-C 4} H 9) 3 [J. Am. Chem. Soc., 86, 1085
(1964)] and the like. Examples of the solvent include ethers such as diethyl ether, diisopropyl ether and 1,2-dimethoxyethane; dioxane; tetrahydrofuran; aromatics such as toluene and xylene.
Of these, diethyl ether and tetrahydrofuran are preferable. The reaction temperature can be selected over a wide range depending on 1) the stability of the solvent used for the metal hydrogen complex compound, and 2) the reactivity of the metal complex compound as a reducing agent. In practice, it is 0 to 100 ° C, preferably 0 to 50 ° C. However, higher temperatures may be used when reducing the reaction time or using reducing agents with low activity.

The condensation reaction between the diphenyl compound of the above [Chemical formula 2] and the N- (4-formylphenyl) carbazole of the above [Chemical formula 3] of the present invention is carried out in a suitable solvent in the presence of a basic catalyst from room temperature to 100 ° C. It is carried out at a moderate temperature. As the basic catalyst, caustic soda, potassium hydroxide, sodium amide, sodium hydride, and sodium methylate, potassium-
Examples thereof include alcoholates such as t-butoxide.
Further, as a reaction solvent, methanol, ethanol, isopropanol, butanol, 2-methoxyethanol,
1,2-dimethoxyethane, bis (2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethyl sulfoxide, N, N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone Etc. Of these, polar solvents such as N, N-dimethylformamide and dimethyl sulfoxide are preferable. The reaction temperature is 1) the stability of the solvent used with respect to the basic catalyst, 2) the reactivity of the condensation component (the compound of [Chemical Formula 2] and the compound of [Chemical Formula 3]),
3) It can be selected over a wide range depending on the reactivity of the basic catalyst as a condensing agent. For example, when a polar solvent is used, it is actually room temperature to 100 ° C, preferably room temperature to 80 ° C. However, higher temperatures may be used when shortening the reaction time or using a less active condensing agent.

[0011]

EXAMPLE 30.4 g (0.1 mol) of diethyl 1,1-diphenylmethylphosphonate and 27.1 g (0.1 mol) of N- (4-formiphenyl) carbazole were dissolved in 500 ml of N, N-dimethylformamide, and potassium- was added thereto. 16.8 g (0.15 mol) of t-butoxide are added at 25-30 ° C. Then, after stirring at room temperature for 8 hours, the reaction solution was poured into 1 liter of water,
The precipitated crystals are filtered, washed with water and dried to give a pale yellow crude product 3
It was 5.3 g (yield 83.7%). This was recrystallized from a mixed solvent of toluene-ethanol to obtain a pure N- (β-phenylstyryl-4-phenyl) carbazole. The melting point was 176.0-176.8 ° C. The infrared absorption spectrum (KBr tablet method) is shown in FIG. The results of elemental analysis are as follows. Elemental analysis results (as C ₃₂ H ₂₃ N) C (%) H (%) N (%) Actual value 91.22 5.32 3.24 Calculated value 91.18 5.50 3.32

[0012]

As is apparent from the above description, the carbazole compound of the present invention is a novel substance and is particularly useful as an organic photoconductive material for electrophotography.

[Brief description of drawings]

FIG. 1 is an infrared absorption spectrum of N- (β-phenylstyryl-4-phenyl) carbazole of the present invention.

Claims (2)

[Claims] Claims: N- (β-phenylstyryl-4-phenyl) carbazole represented by 2. [Chemical formula 2] [Outer 1] A triphenylphosphonium group or -PO (O
R) ₂ (wherein R represents a lower alkyl group) represents a dialkyl phosphite group. ] And a diphenyl compound represented by Is condensed with N- (4-formylphenyl) carbazole represented by: A method for producing N- (β-phenylstyryl-4-phenyl) carbazole represented by: