JP2552695C

JP2552695C -

Info

Publication number: JP2552695C
Authority: JP
Original assignee: Ricoh Co Ltd
Current assignee: Ricoh Co Ltd
Publication date: 1999-09-13

Description

【図面の簡単な説明】第１図は実施例１で得られたジオレフィン芳香族化合物の誘導体の赤外線吸収
スペクトル（ＫＢｒ錠剤法）図であり、第２図は実施例９で得られたジオレフィン芳香族化合物の誘導体の赤外線吸収スパクトル（ＫＢｒ錠剤法）図である。BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an infrared absorption spectrum (KBr tablet method) of a derivative of a diolefin aromatic compound obtained in Example 1, and FIG. It is an infrared absorption spectrum (KBr tablet method) figure of the derivative of an olefin aromatic compound.

Claims

[Claims] 1. General formula (I) A-CH = CH-Ar-CH = CH-A (I) [In the above formula, Ar represents an unsubstituted phenylene group or a biphenylene group; R ¹ and R ² are a substituted or unsubstituted aryl group).
Provided that R ¹ and R ² are simultaneously a phenyl group or a tolyl group]. Description: TECHNICAL FIELD The present invention relates to a novel diolefin aromatic compound, which can be used as an organic photoconductive material for electrophotography and an optical brightener, and particularly, an organic photoconductive material for electrophotography. The purpose of the present invention is to provide a material for each use as a conductive material. 2. Description of the Related Art Conventionally, many materials such as poly-N-vinylcarbazole have been proposed as an organic photoconductive material of a photoreceptor used in an electrophotographic system. The term “electrophotographic method” as used herein generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then only the exposed portion is selectively discharged, whereby the electrostatic latent photoreceptor is discharged. This is one of image forming methods in which an image is obtained, and the latent image portion is visualized by a developing unit using toner or the like to form an image. The basic characteristics required of the photoreceptor in such an electrophotographic system include: 1) being charged to an appropriate potential in a dark place; 2) being less discharged in a dark place;
And (2) discharging electric charges promptly by light irradiation. However, in reality, conventional photoconductive organic materials do not always satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and among them, selenium is widely used practically. However, recently, from the point of the electrophotographic process, various demands for a photoreceptor, for example, in addition to the above-described basic characteristics, for example, a belt-shaped photoreceptor having a flexible shape is also required. It is becoming. However, in the case of selenium, it is generally difficult to produce such a shape. SUMMARY OF THE INVENTION An object of the present invention is to provide a novel diolefin aromatic compound particularly useful as a photoconductive material, which eliminates the above-mentioned disadvantages of a photoconductive material in a photoreceptor, and a method for producing the same. Configuration The present invention provides: General formula (I) A-CH = CH-Ar-CH = CH-A (I) [In the above formula, Ar represents an unsubstituted phenylene group or a biphenylene group; R ¹ and R ² are a substituted or unsubstituted aryl group).
However, according to the diolefin aromatic compound represented by the exception that R ¹ and R ² is a phenyl group or a tolyl group simultaneously]. Diolefin aromatic compound (I) of the present invention, the general formula _{(II) Y-CH 2 -Ar} -CH 2 -Y (II) A triphenylphosphonium group or a dialkylphosphonate group represented by -PO (OR) ₂ (where R represents a lower alkyl group, and Ar is the same as described above); and a phosphorus compound represented by the general formula (III) ) A-CHO (III) (wherein A is the same as defined above). The diolefin aromatic compound of the present invention is a raw material for producing a diethyl aromatic compound that effectively works as a photoconductive substance of an electrophotographic photoreceptor, and the diethyl aromatic compound reduces the diolefin aromatic compound of the present invention. Thus obtained. The phosphorus compound represented by the general formula (II) used in the present invention can be obtained by directly converting the corresponding xylylenedihalide compound with a trialkyl phosphite or triphenylphosphine or toluene, xylene, tetrahydrofuran, N, N-dimethylformamide It is easily produced by heating in a solvent such as Here, the trialkyl phosphite is preferably an alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group. 1 part of the phosphorus compound represented by the general formula (II) thus obtained and the general formula (III)
With 2 parts of an aldehyde compound represented by the formula, in the presence of a basic catalyst, from room temperature to 100 ° C.
The reaction is performed at a temperature of the order. Examples of the basic catalyst include caustic soda, caustic potash, sodium amide, sodium and sodium hydride, and alcoholates such as potassium tert-butoxide and lithium methoxide. 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. Among them, polar solvents such as N, N-dimethylformamide and dimethylsulfoxide are preferred. The reaction temperature is 1) the stability of the catalyst used to a basic catalyst, 2) the reactivity of the condensation components (compounds of the general formulas (II) and (III)), 3) the reaction as a condensing agent in the basic catalyst. A wide selection can be made depending on gender. For example, when a polar solvent is used, the temperature is actually from room temperature to 100 ° C, preferably from room temperature to 80 ° C. However, higher temperatures may be used when shortening the reaction time or using a less active condensing agent. The following examples illustrate the invention in more detail. Example 1 3.78 g of tetraethyl P-xylene-α, α'-diyldiphosphonate (10
. 0 mmol) and 6.67 g (20.0 mmol) of 4-N, N-bis (4-methoxyphenyl) aminobenzaldehyde, 70 ml of N, N-dimethylformamide, and 3.37 g of potassium-t-butoxide. (30.0m
mol) was added at 21-36 ° C over 1 hour. After the addition, the mixture was stirred at room temperature for 5 hours, diluted with 300 ml of water, and neutralized with acetic acid while stirring.
The precipitate was filtered, and the residue was washed with water and methanol to obtain yellow crystals. This was treated with a silica gel-toluene column, and recrystallized from a mixed solvent of ethanol-2-butanone to give 1,4-bis [4-N, N-bis (4-methoxyphenyl) aminostyryl] as orange needle crystals. 4.00 g of benzene (54.3% yield) was obtained. Melting point is 1
77.5-180.0 ° C. FIG. 1 shows the infrared absorption spectrum (KBr tablet method). 963 cm ^-1
In addition, the absorption based on the C-H out-of-plane bending vibration of transolefin was observed. Examples 2 to 10 The same procedure as in Example 1 was carried out except that the aldehyde (A) shown in Table 1 was used instead of 4-N, N-bis (4-methoxyphenyl) aminobenzaldehyde used in Example 1. The diolefin aromatic compound shown in Table 1 was obtained. _{_{_{a) C 48 H 40 N 2}}} · 1 / Calculated b as _{_{_{2DMF) C 48 H 40 N 2}}} S 2 · 1 / calculated for 3DMF Examples 11-12 and Reference Examples 1 to Reference Example 3 Example 1 The tetraethyl (Ar) -α, α′-diyldiphosphonate shown in Table 2 was used in place of the tetraethyl p-xylene-α, α′-diyldiphosphonate used in the above, and 4-N, N-bis (4-methoxyphenyl) A diolefin aromatic compound shown in Table 2 was obtained in the same manner as in Example 1 except that the aldehyde (A) shown in Table 2 was used instead of aminobenzaldehyde. Next, test examples showing that the compound of the present invention is excellent as an organic photoconductive material will be described. Test Example 1 a. Test sample 1) 4,4-bis (4-N, N-ditolylaminostyryl) benzene (comparative compound) 2) 1,4- [4-N, N-di (p-methoxyphenyl) aminostyryl] Benzene (the compound of the present invention) b. Test methods Sample Compound 1 parts was applied with a doctor blade to a conductive load generating layer dissolved in a solution of 1 part of a polycarbonate resin and tetrahydrofuran 8 parts, 2 minutes at 80 ° C., then dried for 5 minutes at 120 ° C. A 20 μm charge transport layer was formed to form a photoreceptor. The photocarrier generation efficiency (PIE) φ of the obtained photoreceptor was measured, and an electric field of 5 × 10
Table 3 shows the value at ⁵ V / cm. As can be seen from Table 3 , the photoreceptor using the compound of the present invention has a higher photocarrier generation efficiency than the comparative photoreceptor, indicating that the compound used is useful as an organic photoconductive material. Test Example 2 a. Test sample 1) 1,4-bis (4-N, N-diphenylaminostyryl) benzene (comparative compound) 2) 1,4-bis [4- (N-methyl-N-phenylamino) styryl] benzene ( Comparative compound) 3) 1,4-bis [4- (Np-tolyl-N-phenylamino) styryl]
-2,5-dimethoxybenzene (compound of Reference Example 1 ) b. Test Method A photoreceptor was prepared by the following method, and its characteristics were measured. On a polyester film support having an aluminum conductive layer, a cyclohexanone dispersion containing a polyvinyl butyral resin and a charge generating material in a weight ratio of 2 to 5 is melt-processed, and after drying, the weight is about 1.7 × 10 ⁻⁵ gr · cm. ^The charge generation layer was formed so as to be ^-5 . On top of this, a charge transport amount was provided from a tetrahydrofuran coating solution containing a polycarbonate resin and a charge generating material in a 10: 9 weight ratio so as to have a film thickness of about 20 μm, thereby producing a laminated organic photoreceptor. c. Test results Since the comparative compounds 1) and 2) are hardly soluble in the tetrahydrofuran resin solution, the photosensitive layer film is dispersed in crystals, and the light transmittance is deteriorated.
_1/2 had a bad residual surface potential. Effect The diolefin aromatic compound obtained as described above is effective as an organic electroconductive material for electrophotography and is a useful intermediate for producing a diethylbenzene derivative.