JPS6094462A - Stilbene derivatives and their production method - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to novel stilbene derivatives and methods for their production.

BACKGROUND OF THE INVENTION In the past, many materials including poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoreceptors used in electrophotography.

The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then the electrostatic latent image is formed by selectively discharging the charge only in the exposed areas. This is one of the image forming methods in which an image is formed by visualizing this latent image using a developing means using toner or the like. The basic characteristics required of a photoreceptor in such an electrophotographic method are 1) to be charged to an appropriate potential in a dark place, 2) to have little discharge of charge in a dark place, and 3) to be able to withstand light irradiation. Examples include discharging charges more quickly. However, the reality is that conventional photoconductive organic materials do 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 practical use. However, recently, in terms of the electrophotographic process, various demands have been placed on the photoreceptor. For example, in addition to the above-mentioned basic characteristics, there is also a demand for a flexible belt-like photoreceptor in terms of shape. This is becoming more and more common. However, in the case of selenium, it is generally difficult to form it into such a shape.

Objective: To provide a stilbene derivative useful as an organic photoconductive material that can be used as an organic photoconductive material for electrophotography, a fluorescent brightener, and particularly satisfies the above requirements for electrophotography, and a method for producing the same. That's true.

Structure The first invention has the general formula (I) l-13 (where Δr, R is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted styryl group, and R is hydrogen, a lower alkyl group, or a substituted or (Represents an unsubstituted phenyl group.) The second invention is the general formula (I[) U in which Ar1R is the same as the general formula (I>, y ttP ”
4) A triphenylphosphonium group represented by 3'Z'' (representing CocoFZ0HaHaLo7), or
A phenyl derivative represented by 1 which is a dialkyl phosphite group represented by -PO(OR)2 (where R- represents a lower alkyl group) is reacted with an aldehyde compound represented by the following general formula (ITI) H3. This is a method for producing a stilbene derivative represented by the following general formula (I) H3 (wherein Ar and R are the same as in general formula (I)).

In the general formulas (I) and (II>, substituents on the phenyl group on Ar or R include alkyl groups such as methyl, ethyl, propyl, butyl, methoxy,
Examples include alkoxy groups such as ~xy, propoxy, butoxy, and halogen electrons such as chlorine and bromine.

The phenyl derivative represented by the general formula (U) used in the present invention can be prepared by combining the corresponding heromethyl compound with trialkyl phosphite or tophenylphos (fin) directly or in a solvent such as toluene, tetrahydrofuran, N,N-dimethylformamide, etc. The trialkyl phosphite has 1 to 4 carbon atoms.
An alkyl group, particularly a methyl group or an ethyl group, is preferred.

The phenyl derivative represented by the general formula (I[) thus obtained and the aldehyde compound represented by the general formula ([[>) are reacted at a temperature from room temperature to about 100° C. in the presence of a basic catalyst.

As F-based catalysts, mention may be made of alcoholades such as caustic soda, caustic potash, sodium amide sodium hydride and sodium methylate, potassium-1-butoxide and the like.

In addition, 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 and the like can be mentioned. Among these, polar solvents such as N 2 , N-dimethylformamide and dimethyl sulfoxide are preferred.

The reaction temperature depends on 1) the stability of the solvent used against the basic catalyst, 2) the reactivity of the condensation components (compounds of general formulas (II) and (III)), and 3) the reaction as a condensing agent in the basic catalyst. You can choose from a wide range of options depending on your gender. For example, when using a polar solvent, it is actually
0°C, preferably room temperature to 80°C. However, higher temperatures may be used if the reaction time is shortened or a less active condensing agent is used. Examples of the novel naphthalene derivatives according to the present invention obtained in this way are as follows.

C+h CH3CH3 CH3 Example 1 Diethyl 1.1-diphenylmethylphosphonate 30.4
(1 (0.1 mol) and 28.7 g (0.1 mol) of 2-methyl-4-N,N-diphenylaminobenzaldehyde and 500n+ of N,N-dimethylformamide.
16.1 of potassium-1-butoxide.
8 g (0.15 mol) are added at 25-35°C. After stirring at room temperature for 6 hours after addition, the mixture was diluted with 1λ of water.
diluted with The precipitated powder was filtered, washed with water, and dried to obtain a pale yellow powder.

The yield was 37.1 (1 (yield 85%). It was recrystallized from a mixed solvent of ethyl acetate and ethanol to obtain 2-methyl-
4-N, N-diphenylamino-β-phenylstilbesi pure product is 10. Melting point 119.5-121.0
It was ℃. Table 1 shows the stilbene derivatives prepared using infrared garlic flavor (KB). .

Example 7 4-chlorobenzyltriphenylphosphonium chloride 42.3 (0.1 mol) and 2-methyl-4-N,
28.7 g of N-diphenylaminobenzaldehyde (
0.1 mol) to N,N-dimethylformamide 500
ml of potassium-[-butoxide
6. h (0.15 mol) is added at 25-35°C. After stirring at room temperature for 5 hours after the addition, the reaction mixture was diluted with 1 part of water.
diluted with β.

The precipitated powder was separated by filtration, washed with water, and dried to obtain a pale yellow powder. The yield was 38.8(] (yield 98.θ%) and the melting point was 1.
The temperature was 27.5-129.5°C.

Recrystallized from a mixed solvent of toluene-〇-hexane with a trace amount of iodine to give pale yellow needle-like crystals of 2-methyl-4-N.
, N-diphenylamino-4-1chlorostilbene was obtained. Yield: 30.6g (yield: 77.4%), melting point: 12
The temperature was 9.3 to 130.5°C.

Effects As is clear from the above explanation, the stilbene derivative according to the present invention is a novel compound, and is particularly effective as an organic photoconductive material for electrophotography.

[Brief explanation of drawings]

The figure shows 2-methyl-4-N, N-diphenylamino-β
- It is an infrared absorption spectrum diagram of phenylstilbene. Patent Applicant Rico Co., Ltd. - Agent Patent Attorney Hidetake Komatsu Agent Patent Attorney Hiroshi Asahi Procedural Amendment Letter November 11, 1981 3, Relationship with the person making the amendment Patent applicant name (674) Stocks Company Rico-4, Agent
107 (Telephone 586-8854) Name (7899)
Patent attorney Hidetake Komatsu (1 idiot) 5. Date of amendment order (voluntary) Corrected to ``As a substituent on the benzene ring.''

Claims (1)

[Claims] (1) General formula (I) (In the formula, Ar represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted styryl group, and R represents hydrogen, a lower alkyl group, or a substituted or unsubstituted phenyl group.) A stilbene derivative represented by (2J general formula (II) In the E formula, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted styryl group τ or an unsubstituted phenyl group, Y is pe required) 3Ze ( where 70 represents a halogen), or a dialkylphosphite group represented by PO(OR'>2 (where R' represents a lower alkyl group)). The phenyl rust conductor represented by the following general formula <I
II) A method for producing a stilbene derivative represented by the following general formula (, I) H3 (wherein Ar and R are the same as above), which comprises reacting with an aldehyde compound represented by H3.