Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative

A technology of difluoroalkoxybenzene and liquid crystal monomers is applied in the preparation of ethers, the preparation of ethers by ester reaction, organic chemistry, etc. Conducive to large-scale production, overcoming inability to isomerize, and improving product yield

Active Publication Date: 2012-12-19
VALIANT CO LTD
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the disadvantage that the cis structure of alkoxy-containing liquid crystal monomers cannot be isomerized, and to provide a preparation method for liquid crystal monomers of o-difluoroalkoxybenzene derivatives

Method used

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  • Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative
  • Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative
  • Preparation method for liquid crystal monomer of o-difluoroalkoxybenzene derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0044] When n=0, R 1 is n-butyl, R 2 When it is propyl, the product is 1-butoxy-4-(4-propyl-cyclohexyl)-benzene

[0045] 1) 1-(2,3-difluoro-phenyl)-4-propyl-cyclohexanol: add 100g (0.877mol) o-difluorobenzene, 300gTHF into a 2000ml three-necked flask, and store at -40℃ Add 256.425g (0.8335mol) of n-butyllithium solution dropwise, and after the dropwise addition, keep warm for 1 hour, add 116g 4-propylcyclohexanone (0.828mol), 116gTHF solution, keep warm for 2 hours, hydrolyze and separate, and wash the organic phase with water After neutralization, wait for the next step dehydration reaction; or,

[0046] 1-(2,3-Difluoro-phenyl)-4-propyl-cyclohexanol: Add 100g (0.877mol) o-difluorobenzene and 300gTHF to a 2000ml three-neck flask, add 22g (0.921mol ) Metal magnesium, after the addition is completed and kept warm for 1 hour, add 116g 4-propyl-cyclohexanone (0.828mol), 200gTHF solution, keep warm for 2 hours, hydrolyze and separate, and after the organic phase is washed with w...

Embodiment 2

[0054] When n=1, R 1 is propyl, R 2 When it is methyl, the product is 4-(2,3-difluoro-4-propoxy-phenyl)-4'-methyl-bicyclohexane

[0055] 1) 4-(2,3-difluoro-phenyl)-4'-methyl-bicyclohexyl alcohol: Add 100g (0.877mol) o-difluorobenzene, 400gTHF to a 2000ml three-necked bottle, and store at -50℃ Add 269.808g (0.877mol) sec-butyllithium solution dropwise, after the dropwise addition and keep warm for 2 hours, add 160.6g (0.828mol) 4-(4'-methyl-cyclohexyl) cyclohexanone, 116gTHF solution, keep warm After 2 hours, hydrolysis and separation, the organic phase was washed with water and neutralized, and then the next dehydration reaction was performed; or,

[0056] 4-(2,3-difluoro-phenyl)-4'-methyl-bicyclohexyl alcohol: add 100g (0.877mol) o-difluorobenzene, 400g THF to a 2000ml three-necked flask, add 23.15g ( 0.965mol) metal magnesium, after the heat preservation is completed for 1 hour, add 160.6g (0.828mol) 4-(4'-methyl-cyclohexyl) cyclohexanone and 200g THF solution, heat for 2...

Embodiment 3

[0064] When n=2, R 1 is ethyl, R 2 When it is n-butyl, the product is 4″-butyl-4-(4-ethoxy-2,3-difluoro-phenyl)-[1,1';4′,1″]tricyclohexane

[0065] 1) 4-(2,3-difluoro-phenyl)-4″-butyl-[1,1’;4’,1″]tricyclohexyl alcohol: add 100g (0.877 mol) o-difluorobenzene, 500gTHF, 275.204g (0.895mol) sec-butyllithium solution was added dropwise at -70°C, and after the addition was completed and kept warm for 3 hours, 263.3g (0.828mol) 4″-butyl- [1,1';4',1″]Tricyclohexanone, 120g THF solution, keep warm for 2 hours, hydrolyze and separate layers, wash the organic phase with water to be neutral, and wait for the next step of dehydration reaction; or,

[0066] 4-(2,3-difluoro-phenyl)-4″-butyl-[1,1’;4’,1″]tricyclohexyl alcohol: add 100g (0.877mol) to a 2000ml three-necked bottle o-difluorobenzene, 500gTHF, add 25.26g (0.921mol) magnesium metal at 30°C, after the dropwise addition is completed and keep warm for 1 hour, add 263.3g (0.828mol) 4″-butyl-[1,1';4', 1″]Tricyclohexanone, 120g THF so...

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Abstract

The invention relates to the field of liquid crystal displays and particularly relates to a preparation method for a liquid crystal monomer of an o-difluoroalkoxybenzene derivative used for liquid crystal displays. According to the preparation method, 1,2-difluorobenzene or 1,2-difluorobromobenzene is used as a raw material and undergoes metallization or a Grignard reaction with a cyclohexyl ketone compound, then dehydration and hydrogenation are carried out to prepare a compound containing cis-trans-isomers, and finally isomerization and oxyalkylation are successively carried out. The method overcomes the disadvantage of incapable isomerization of a cis structure of liquid crystal monomers containing alkoxy groups, increases product yield, reduces production cost, is beneficial for mass production and has a great application prospect.

Description

technical field [0001] The invention relates to the field of liquid crystal display, in particular to a preparation method of o-difluoroalkoxybenzene derivative liquid crystal monomer used for liquid crystal display. Background technique [0002] Fluorine-containing liquid crystals have the advantages of low viscosity, high resistivity, fast response speed, and can increase the dielectric constant of mixed crystals, and are very suitable for liquid crystal displays driven by thin film field effect transistors. Especially o-difluoroalkoxy liquid crystal molecules, this type of monomer liquid crystal can increase the value of Δε (dielectric anisotropy), reduce the rotational viscosity of liquid crystal molecules, improve the compatibility and low temperature performance of liquid crystal, and can be used in liquid crystal display templates has very good application prospects. [0003] However, in the existing preparation method of o-difluoroalkoxy liquid crystal monomer, a mi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C41/16
Inventor 李鹏周银波朱世乾申川生王成龙李忠鹏宋天资刘佳苑志刚
Owner VALIANT CO LTD
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