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P-electron conjugated organosilane compound and method for synthesizing same

An organosilane and compound technology, applied in the field of π-electron-conjugated organosilane compounds and their preparation, can solve the problems of difficulty in providing self-organized film conductivity, and achieve high stability, prevention of physical peeling, and high conductivity. Effect

Inactive Publication Date: 2007-06-27
SHARP KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, although the conductivity of the self-assembled film is determined by the organic functional group of the silicon-based compound contained in the film, there is no commercially available silane coupling agent having an organic functional group containing π-electron conjugated molecules, and for this reason, few Difficult to provide self-organized thin film conductivity

Method used

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  • P-electron conjugated organosilane compound and method for synthesizing same
  • P-electron conjugated organosilane compound and method for synthesizing same
  • P-electron conjugated organosilane compound and method for synthesizing same

Examples

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Effect test

preparation example 1

[0314] Prepare three selenophene trichlorosilane (terselenophenetrichlorosilane) (X 1 =X 2 =X 3 = Cl; Y = Se; R 2 = R 3 =H and n1=3) (Grignard method)

[0315] This compound was prepared according to Synthetic Scheme 1. Specifically, at first, put 50ml chloroform and 70mM selenophene into a 100-ml round bottom flask, cool the mixture to 0°C temperature; add 20M NBS (N-bromosuccinimide) therein, stir The mixture was left for 1 hour. After the product was extracted with purified water, it was purified under reduced pressure at 80°C to obtain 2-bromoselenophene. Then, in a nitrogen atmosphere, 5 ml of anhydrous THF and 30 mM 2-bromoselenophene were put into a 50-ml round bottom flask; magnesium was added thereto; and the mixture was stirred for 2 hours. Then, add catalyst-containing Ni(dppp)Cl to it 2(dichloro[1,3-bis(diphenylphosphino)propane]nickel(II)) and 30 mM 2-bromoselenophene in 5 ml of anhydrous THF, and the mixture was reacted at 0°C for 12 hours. The product w...

preparation example 2

[0328] Preparation of tetraselenophene trimethoxysilane (X) represented by general formula (1) 1 =X 2 =X 3 =OCH 3 ;Y=Se,R 2 = R 3 = H; n1 = 4)

[0329] First, under a nitrogen atmosphere, 5 ml of anhydrous THF and 5 mM of the intermediate 2-bromodiselenophene obtained in Preparation Example 1 were put into a 50 ml round bottom flask; magnesium was added thereto; and the mixture was stirred for 2 hours. Then, add catalyst-containing Ni(dppp)Cl 2 and 5 mM 2-bromodiselenophene in 5 ml of anhydrous THF, and the compound was reacted at 0° C. for 10 hours. The product was purified by flash chromatography after extraction with purified water to obtain tetraselenophene (35%).

[0330] Then, 50 ml of chloroform and 70 mM of the intermediate tetraselenophene obtained in Preparation Example 2 were put into a 100-ml round bottom flask; the mixture was cooled to 0° C., and after adding 70 M NBS, stirred for 1 hour. After the product was extracted with purified water, it was purifie...

preparation example 3

[0340] Preparation of octaselenophene triethoxysilane (X) represented by general formula (1) 1 =X 2 =X 3 =OC 2 h 5 ;Y=Se;R 2 = R 3 = H; n1 = 8)

[0341] First, under a nitrogen atmosphere, 5 ml of anhydrous THF and 5 mM of the intermediate 2-bromotetraselenophene obtained in Preparation Example 2 were put into a 50 ml round bottom flask; magnesium was added thereto; and the mixture was stirred for 3 hours. Then, add catalyst-containing Ni(dppp)Cl 2 and 5 mM 2-bromotetraselenophene in 5 ml of anhydrous THF, and the compound was reacted at 0° C. for 12 hours. The product was purified by flash chromatography after extraction with purified water to obtain octaselenphene (30%).

[0342] Then, 50 ml of chloroform and 70 mM of the above octaselenphene were put into a 100-ml round bottom flask; the mixture was cooled to 0° C., and after adding 10 M NBS, the mixture was stirred for 1 hour. After the product was extracted with purified water, it was purified under reduced press...

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Abstract

Disclosed is a pi-electron conjugated organosilane compound which enables to form an organic thin film having excellent separation resistance as well as high orderliness, crystallinity and electric conductivity. Also disclosed is a method for synthesizing such a pi-electron conjugated organosilane compound. Specifically disclosed is a pi-electron conjugated organosilane compound expressed as 1-SiX1X2X3 (wherein R1 represents an organic group containing a certain monocyclic heterocycle unit and X1-X3 respectively represent a group providing a hydroxyl group through hydrolysis). Also disclosed is a method for synthesizing such an organosilane compound wherein a compound expressed as R1-Li (wherein R1 is as defined above) or a compound expressed as R1-MgX5 (wherein R1 is as defined above and X5 represents a halogen atom) is reacted with a compound expressed as X4-SiX1X2X3 (wherein X1-X3 are as defined above and X4 represents a hydrogen atom, a halogen atom or a lower alkoxy group). Also specifically disclosed is a pi-electron conjugated organosilane compound expressed as Z-(R11)m-SiR12R13R14 (wherein Z represents an organic group derived from a certain condensed polycyclic heterocyclic compound, R11 represents a divalent organic group, m represents 0-10, and R12-R14 respectively represent a halogen atom or an alkoxy group). Also disclosed is a method for producing such an organosilane compound wherein a compound expressed as Z-(R11)m-MgX30 (wherein Z, R11 and m are as defined above, and X30 represents a halogen atom) is reacted with a compound expressed as X31-SiR12R13R14 (wherein X31 represents a hydrogen atom, a halogen atom or an alkoxy group, and R12-R14 are as defined above).

Description

technical field [0001] The present invention relates to a π-electron conjugated organosilane compound and a preparation method thereof. Specifically, the present invention relates to a novel π-electron conjugated organosilane compound that can be used as an electrical material and a preparation method thereof. This compound has excellent electrical conductivity sex or semiconductivity. Background technique [0002] In recent years, research and development of semiconductors using organic compounds (organic semiconductors) has been carried out because compared with semiconductors made of inorganic materials, organic semiconductors are easier to prepare, easier to process, and can accommodate the enlargement of device size, allowing cost reduction through mass production , and its function is more than that of inorganic materials, and thus there have been reports on such organic semiconductors. [0003] In particular, it is known that TFTs with high mobility can be produced u...

Claims

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Application Information

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IPC IPC(8): C07F7/12C07F7/18H01B1/12
Inventor 中川政俊花户宏之田村寿宏
Owner SHARP KK
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