JPS59191763A - Stilbene derivative and production thereof - Google Patents

Abstract

NEW MATERIAL:Stilbene derivatives of formula I , wherein Ar is N-ethylcarbazolyl or a group of formula II [wherein R1, R2 are each lower alkyl, benzyl, (substd.) phenyl]; n is 0, 1. EXAMPLE:Compound of formula III. USE:Org. photoconductive materials which give flexible photosensitive materials with good sensitivity for use in electrophotography. PREPARATION:A phenyl derivative of formula IV (wherein R is lower alkyl) is reacted with an aldehyde compd. of formula V (wherein Ar is as defined above) to produce the compd. of forula I .

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a novel stilbene derivative and a method for producing the same, which can be used as an organic photoconductive material and a fluorescent brightener for electrophotography. The present invention provides a material useful as a photoconductive material.

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 an Itp image means using toner or the like. The basic characteristics required of a photoreceptor in such an electrophotographic method are: 1)
Examples include: being charged to an appropriate potential in a dark place, 2) having little discharge of electric charge in a dark place, and 3) quickly discharging electric charge upon irradiation with light. but,
The reality is that conventional photoconductive organic materials do not necessarily meet 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, in recent years, various demands have been placed on photoreceptors in terms of the electrophotographic process.
There is an increasing demand for photoreceptors with similar shapes. However, in the case of selenium, it is generally difficult to create a shape like this.

OBJECTIVES It is an object of the present invention to provide a novel stilbene derivative that is particularly useful as a photoconductive material and a method for producing the same, which eliminates the drawbacks of photoconductive materials for photoreceptors as described above.

The first invention is based on the general formula (I) (wherein, Ar is an N-ethylcarbazolyl group or R2
(In the formula, R1 and R2 represent a lower alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group), and n is an integer of 0 or 1. ) is a stilbene derivative represented by

5- The second invention is a phenyl derivative represented by the general formula (I[) (wherein R represents a lower alkyl group) and the following general formula ([%formula%() (wherein, Ar is N - ethylcarbazolyl group or an alkyl group, benzyl group or substituted or unsubstituted phenyl group), where n is an integer of 0 or 1). The following general formula (I) 6- (wherein, Ar is an N-ethylcarbazolyl group or R2
(In the formula, R1 and R2 represent a lower argyl group, a benzyl group, or a substituted or unsubstituted phenyl group), and n is an integer of O or 1. ) This is a method for producing a stilbene derivative represented by:

In the general formula (I) and (I[[), R1 or R
Substituents on the phenyl group in 7 include an argyl group, an alkoxy group, a thioalkoxy group, a thiophenoxy group, a halogen atom, a dialkylamino group, a hydroxy group,
Carboxy group and its Nisdel, acyl group, aryloxy group, aralkyloxy group, trifluoromethyl group,
Examples include a 21-ro group and a cyano group.

The phenyl derivative represented by the general formula (I) used in the present invention can be easily produced by heating the corresponding heromethyl compound and 1-realkyl phosphite directly or in a solvent such as 1-toluene or xylene. . Here, the trialkyl phosphite is preferably an alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group.

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

As the basic catalyst, mention may be made of alcolades such as caustic soda, caustic potash, sodium amide sodium hydride and sodium methylate, and potassium-(-butyloxide).As the reaction solvent, methanol,
Ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, bis(2
-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethylsulfoxide, N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like. Among them, polar solvents such as N,N-dimethylformamide and dimethyl sulfoxide are preferred.

The reaction temperature is determined based on 1) the stability of the solvent used against the basic catalyst, 2) the reactivity of the condensation component (compounds of general formulas (I[) and (III))), and 3) the stability of the condensing agent as a condensing agent in the basic catalyst. A wide range of choices can be made depending on reactivity. 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 novel stilbene derivatives according to the present invention obtained in this way are as follows.

9- f-13 -10= CH3 CH3 2H5 The novel methylbene derivative according to the present invention is extremely useful as a photoconductive material in electrophotographic photoreceptors, and can be optically oxidized with a sensitizer such as a dye or a Lewis acid. Targeted or chemically sensitized.

It is also particularly useful as a charge transfer material in so-called functionally separated photoreceptors in which an organic pigment or an inorganic pigment is used as a charge generation material.

Examples of the sensitizers include triallylmethane dyes such as methyl violet and crystal violet; Santen dyes such as rose bengal, erythrosine, and rhodamine B;
Examples include azine dyes such as methylene blue, 2,4.7-1-linitro-9-fluorenone, 2,4-dinitro-9-fluorenone, and the like.

Also, as an organic pigment, C.I. Pigment Blue 25
(CI No. 21180), CI Pigment Red 41 (CI No. 21200>, CI Basic Red 3 (CI No. 4521)
Azo pigments such as C.I. Bigmency Blue 16
(CI No. 74100), Sea Eye Butt Brown 5 (CIN 0.734)
10), CI Violet Dye (CI No
, 73030), and perylene pigments such as A13-Lugo Scarlet B and Intance Scarlet R. Inorganic materials such as selenium and selenium-tellurium silicon can also be used.

Next, the present invention will be explained in more detail with reference to Examples.

Example 1 Diethyl α-methylbenzylphosphonate 2,42 (1
(0.01 mol) and 2.73 (1( 0.01 mol) of 4-N,N-Schiffinylaminobenzaldehyde
) was dissolved in 15IIlρ of N,N-dimethylformamide, and 1,35% of potassium tert-butoxide was dissolved therein.
LJ was added at 22-35°C. After the addition, the reaction mixture was stirred at room temperature for 7 hours, and then diluted with water at 50 m°C. The produced oil was extracted with toluene, the toluene layer was washed with water, dried, and then the toluene was distilled off to obtain yellow crystals. Revenue W
i 3.04 0 (yield 84.0%), melting point 96.5~
The temperature was 99.5°C.

Next, it was recrystallized from ethanol to obtain α-
Methyl-4=-N. A pure product of N-diphenyl 14-aminomethylben was obtained.

Melting point: 158.5-160.5°C Elemental analysis: 0% I'% N% Actual value: 89,87 6.42 3.8
Calculation as 2C771-h3N (ifi 89.70 6./1
3 3.88 The infrared absorption spectrum (KBr tablet method) is shown in the figure, but it is 970CI11-'! -Rance's CH
-An absorption band based on out-of-plane bending vibration was observed.

Examples 2 to 11 A novel stilbene derivative was obtained in the same manner as in Example 1 except that the aldehydes shown in Table 1 below were used instead of 4-N,N-diphenylaminobenzaldehyde. The results are shown in Table 2.

Table 2 Effects As is clear from the above 81 results, the methylbene derivative according to the present invention is a novel compound, and is particularly effective as an organic photoconductive material for electrophotography.

[Brief explanation of the drawing]

The figure is an infrared absorption spectrum diagram of α-methyl-4''-N,N-diphenylaminostilbene. Patent applicant: Ricoh Co., Ltd., agent, patent attorney: Hidetake Komatsu, Commissioner of the Japan Patent Office, May 17, 1980, for amendment of proceedings Kazuo Wakasugi Tono 1, Indication of matter A 11 Patent application 1986-6/4529
Item 2. Title of the invention Stilbene derivatives and their manufacturing method 3. Relationship between the person making the amendment and the case Patent application Name of person
(674) Rico Co., Ltd.-4, Agent 〒10
7 (Telephone 58G-8854) 5. Correction order day 1
(Spontaneous) 100.5-101.5℃”. 379-

Claims (2)

[Claims] (1) General formula (I) (wherein Ar represents an N-ethylcarbazolyl group, an alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group), and n is an integer of 0 or 1. . ) is a stilbene derivative. (2) A phenyl derivative represented by the general formula (I [) (wherein R represents a lower alkyl group) and the following general formula () % formula % () (where Ar is N-ethylcarbazolyl Group also R2
(In the formula, R1 and R7 represent a lower alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group), and n is an integer of O or 1. The following general formula (I) is characterized in that it is reacted with an aldehyde compound represented by , n is an integer of O or 1. ) A method for producing a stilbene derivative represented by