JPS5936645A - Preparation of 9,10-bisstyrylanthracene derivative - Google Patents

Abstract

PURPOSE:To prepare the titled compound useful as a photo-conductive substance, from an easily available raw material, economically, in high purity, by reacting a 9,10-bisanthrylmethylphosphonic acid dialkyl derivative with an aldehyde derivative. CONSTITUTION:The objective compound of formula II is prepared by reacting the 9,10-bisanthrylmethylphosphonic acid dialkyl derivative of formula I (R1 is 1-4C lower alkyl) with the aldehyde derivative of formula R2CHO (R2 is dialkylamino-substituted aromatic residue) in a solvent such as alcohol, benzene, etc. in the presence of a base (e.g. sodium hydroxide, sodium hydride, etc.) at room temperature -100 deg.C. The starting compound of formula I can be prepared by reacting a trialkyl phosphite with the corresponding halomethyl compound directly or in an inert solvent such as toluene under heating. USE:Useful as a photosensitive material for electrophotograhy, an image-forming element, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a 9.10-bisstyrylanthracene derivative, specifically I(:J:, represented by the following general formula [wherein I is an aromatic group substituted with a dialkylamino group] Residues are shown.] 9. A method for producing a lO-bisstyrylanthracene derivative.

The 9.10-bisstyrylanthracene derivative shown here has the general formula (1) [However, R1 represents a lower alkyl group having 1 to 4 carbon atoms.

] A dialkyl 9,10-bisanthrylmethylphosphonic acid derivative represented by the general formula (It) R, -CHO [However, R2 represents an aromatic residue substituted with a dialkylamino group. ] If the aldehyde derivative represented by the following is reacted under mild conditions in the presence of an appropriate basic catalyst, it can be produced with high purity and extremely high yield.

The raw material compound of general formula (1) used in the method of the present invention is produced by heating trialkyl phosphite and the corresponding halomethyl compound directly or in an inert solvent such as toluene. The alkyl group in the trialkyl phosphate is preferably an alkyl group having 4 or less carbon atoms, particularly a methyl group or an ethyl group.

The raw material compound represented by the general formula (1) thus obtained and the aldehyde derivative represented by the general formula (1) are reacted in the presence of a basic catalyst at a temperature from room temperature to about 100°C.

Examples of the basic catalyst include common oil-leveling substances such as caustic soda, caustic potash, alcolades such as sodium methylate, sodium hydride, and hydrium amide.

Tit, common reaction media include methylaluminum, ethyl alcohol, zolopyl alcohol, ethyl alcohol, benzene, toluene, xylene, chlorobenzene, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, etc. can.

The compound obtained by the method of the present invention is useful as a photoconductive material, and is a typical organic photoconductive material such as Jf! +7- Compared to N-vinylcarnozole, it has superior photoconductivity, and can be obtained in high purity, which is essential for photoconductive substances, and can be easily synthesized from readily available raw materials, so it is cost effective. is also advantageous.

Compounds with such advantages can be used not only as electrophotographic photoreceptors but also as image forming elements, but when used as electrophotographic photoreceptors, they must be used as dyes or electron acceptors like other organic photoconductive substances. It can also be sensitized by combining it with a photoconductive pigment, and if it is dispersed in a binder as a carrier generation layer and becomes conductive, it is dissolved in the binder solution and the photoconductive pigment is bonded to the conductive support. It can also be used as a carrier transport layer by coating a carrier generation layer on which an agent or photoconductive pigment is deposited.

Example 9.10-Diethyl bisanthrylmethylphosphonate 1
．． 91,! i' (0,004mole) in DMF
t-BuOK (potassium-1
-butoxide) 0.281 (0,012 mole
) was added dropwise to the mixture while stirring at room temperature, and yellow crystals began to precipitate immediately. After stirring for another 2 hours at the same temperature,
Diluted with about 150gLt of water, separated the precipitated crystals,
Washed with water and dried.

As a result, 9.10-pissu with a melting point of 320°C or higher was obtained (yield 91.1°, nitrogen analysis value, actual value (6.98%), calculated value (5.98%)).
%) λmax (DMF) 432 nm 6-2, Name of the invention Method for producing 9,10-bisstyrylanthracene derivatives - 1-3-6 Nakamagome, Ota-ku, Tokyo (674) Ricoh Co., Ltd. - Representative Hama 1) Hiro 4, Agent 5, Column of “Detailed Description of the Invention” of the specification to be amended Contents of the amendment (1) “Example” in the 16th line of the 5th contribution was changed to “Example 1
”, he corrected.

(2) [λmax (DMF) 4 on the 3rd line from the 6th nobleman
After 32 nmJ, change the line and add the following.

[Example 2] Same as Example 1 except for changing the melting point 286, 0~
28B Yellow needle-like crystals of 9,10-bisstyrylanthracene derivative were obtained at 6°C (yield 90.5%).

The elemental analysis values of this product are: C is actually measured value 86.82 (calculated value 86.96), and TI is actually measured value 7.7.
5CItt value 7.70), and N was actually measured value 5.39 (calculated value 5.34). "that's all

Claims (1)

[Claims] General formula (1) [However, R1 represents a lower alkyl group having 1 to 4 carbon atoms. ] A dialkyl 9,10-bisanthrylmethylphosphonate derivative represented by the following formula (If) R, CHO [However, R3 is dialkyl] represents an aromatic residue substituted with a group. ] A method for producing a 9, 0-bisstyrylanthracene visiting conductor represented by the general formula (1) [Iro, 1 (, is as described above)], characterized by reacting with an aldehyde derivative represented by .