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3,4-difluoro-2-methoxyl biphenyl derivative and its preparation process and application

A technology of methoxybiphenyl and methoxybromobenzene, which can be used in ether preparation, chemical instruments and methods, liquid crystal materials, etc., can solve the problems of low viscosity, poor solubility, and high melting point, and achieves lower melting point and wider Application prospects, the effect of increasing solubility

Inactive Publication Date: 2008-03-05
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Gray et al first synthesized side fluorine-containing terphenyl compounds and cyclohexyl biphenyl compounds for TFT--LCD (G.W.Gray, M.Hird etc., J.Chem.Soc.Perkin Trans.2, 1989, 2041~2053), although this type of compound has a wide nematic temperature range and low viscosity, it has a high melting point and poor solubility

Method used

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  • 3,4-difluoro-2-methoxyl biphenyl derivative and its preparation process and application
  • 3,4-difluoro-2-methoxyl biphenyl derivative and its preparation process and application
  • 3,4-difluoro-2-methoxyl biphenyl derivative and its preparation process and application

Examples

Experimental program
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Effect test

Embodiment 1

[0064]Embodiment 1, preparation 4'-ethyl-3,4-difluoro-2-methoxybiphenyl

[0065] 1. Preparation of 3,4-difluoro-2-methoxyphenylboronic acid

[0066] Add 22.3g (0.1mol) of 3,4-difluoro-2-methoxybromobenzene, 50ml of tetrahydrofuran, 2.43g (0.1mol) of magnesium metal and 1 to 2 grains of iodine into a 250ml three-necked flask, and initiate the reaction at room temperature Stir and react for 1 hour, then lower the temperature of the system to -70°C with ethanol-liquid nitrogen system, slowly add 10.4g (0.1mol) trimethyl borate dropwise at this temperature, and make it under stirring condition after the dropwise addition is completed. Naturally rise to room temperature, then dropwise add 10% HCl solution to pH 1, heat to 100°C and reflux for 1 hour. After the reaction solution was cooled, the aqueous phase was extracted with 100ml×3 petroleum ether, washed with saturated brine until neutral, and dried overnight with anhydrous sodium sulfate. The dried solution was rotary evapora...

Embodiment 2

[0082] Example 2, preparation of 4'-(trans-4"-pentylcyclohexyl)-3,4-difluoro-2-methoxybiphenyl

[0083] 1. Preparation of 4'-(trans-4"-pentylcyclohexyl)phenylboronic acid

[0084] Add 30.9g (0.1mol) 4'-(trans-4"-pentylcyclohexyl) bromobenzene, 50ml tetrahydrofuran, 2.43g (0.1mol) metal magnesium and 1~2 grains of iodine to a 250ml three-necked flask, After initiating the reaction at low temperature, stir for 1 hour, then use the ethanol-liquid nitrogen system to lower the system temperature to -70°C, slowly add 10.4g (0.1mol) trimethyl borate dropwise at this temperature, and after the dropwise addition, under stirring conditions Allow it to rise to room temperature naturally, then add 10% HCl solution dropwise to pH 1, and heat to reflux at 100°C for 1 hour. After cooling the reaction solution, extract the aqueous phase with 100ml×3 petroleum ether, and then use saturated Wash with brine until neutral, and dry overnight with anhydrous sodium sulfate. The dried solution was e...

Embodiment 3

[0100] Example 3, preparation of 4"-pentyl-3,4-difluoro-2-methoxy-(1,1',4',1") terphenyl

[0101] Add 18.8g (0.1mol) 3,4-difluoro-2-methoxyphenylboronic acid obtained in Example 1 to a 500ml three-necked flask, 30.2g (0.1mol) 4'-pentyl-4-bromobiphenyl, 150ml Benzene, 75ml of absolute ethanol, 30g of sodium carbonate, 10g of water and 2.5g of tetrakis(triphenylphosphine)palladium were heated to reflux at 100°C for 24 hours and then cooled to room temperature. Separate the organic phase, extract the aqueous phase with 80ml×3 chloroform, combine the organic phases, wash with water until neutral, and dry with anhydrous sodium sulfate. The dried solution was rotary evaporated to remove the solution to obtain 27.5g of 4"-propyl-3,4-difluoro-2-methoxy-(1,1',4',1") terphenyl, yield 75% .

[0102] DSC (differential scanning calorimeter): Cr61.3I;

[0103] IR: Wavenumber / cm -1 =2954, 2931, 2856, 1915, 1884, 1610, 1491, 1468, 1427, 1408, 1392, 1315, 1275, 1230, 1176, 1092, 1049, 1005...

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Abstract

The present invention is 3,4-difluoro-2-methoxyl biphenyl derivative in the given structure and its preparation process and application. The compound of the present invention has methoxyl radical, possessing small space size, small electric dipole moment and average dipole direction in the molecular major axis direction, introduced to the side of the biphenyl ring, so as to have great dielectric anisotropy in the molecular major axis direction, lowered smelting point and increased dissolvability. The compound of the present invention may find wide application in LCD, especially in TFT-LCD.

Description

technical field [0001] The present invention relates to an organic compound and its preparation method and application, in particular to 3,4-difluoro-2-methoxybiphenyl derivative and its preparation method, as well as the application of the compound in liquid crystal display. Background technique [0002] Active Matrix Liquid Crystal Display (AM-LCD) was invented in the late 1970s, but its real application was in the mid-1980s. At present, the main application is thin-film transistor liquid crystal display (TFT-LCD). Due to its fast response speed and high-quality color picture display, this technology is used to realize video image display. It is mainly used in TVs, portable computers, desktop computers, and cameras. , mobile phones and various terminal displays have become one of the main directions of LCD development in the future. With the rapid development of TFT-LCD technology, TFT-LCD has more and more urgent requirements for high-performance liquid crystal materials...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/247C07C41/01C07D239/26C09K19/06C09K19/34
Inventor 唐洪梁晓张伟张百哲
Owner TSINGHUA UNIV
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