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Liquid crystal compound containing 2,3-difluoro-5,6-dimethylphenyl and its preparation method and application

A liquid crystal compound, compound technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of TFT-LCD response is not fast enough, voltage is not low enough, charge retention rate is not enough, etc., to improve the response speed , the effect of low rotational viscosity and high elastic constant

Active Publication Date: 2019-04-12
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the limitations of the liquid crystal material itself, TFT-LCD still has many defects such as insufficient response, insufficient voltage, and insufficient charge retention rate.

Method used

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  • Liquid crystal compound containing 2,3-difluoro-5,6-dimethylphenyl and its preparation method and application
  • Liquid crystal compound containing 2,3-difluoro-5,6-dimethylphenyl and its preparation method and application
  • Liquid crystal compound containing 2,3-difluoro-5,6-dimethylphenyl and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Synthesis of (LC-01)

[0099]

[0100] 1) Synthesis of 2,3-difluoro-4,5,6-trimethylphenylboronic acid (compound 1-2)

[0101] Add 31.2g of 3,4-difluoro-5,6-dimethyltoluene (compound 1-1, 0.2mol) and 1000ml of tetrahydrofuran into a 2L dry and clean three-necked flask. ℃, add 80ml of butyllithium dropwise, and react for 1 hour under temperature control after dropping, add 32g of trimethyl borate (0.30mol) dropwise, after dropping, control temperature at -75°C~-85°C for 30 minutes, then naturally heat up to -20°C , Add dropwise 600ml aqueous hydrochloric acid. Separation, the aqueous phase was extracted twice with 400ml×2 ethyl acetate, the organic phases were combined, and spin-dried to obtain a white solid, the liquid phase purity (LC) was 99.0%, the theoretical yield was 40.0g, the actual yield was 36.0g, and the yield was 90%;

[0102] 2) Synthesis of 1,2-difluoro-3,4,5-trimethyl-6-(4-propyl-cyclohexyl)benzene (LC-01)

[0103] Add 40mL of absolute ethanol, 800...

Embodiment 2

[0108] Synthesis of (LC-02)

[0109] The route is as follows:

[0110]

[0111] 1) Synthesis of 2,3-difluoro-5,6-dimethylphenylboronic acid (compound 2-2)

[0112]Add 14.2g of 3,4-difluoro-5-methyltoluene (0.1mol) and 500ml of tetrahydrofuran to a 1L dry and clean three-necked flask, protect with nitrogen, cool down to -75°C to -85°C with liquid nitrogen, and add 40ml of butyl Lithium, temperature control reaction for 1h, dropwise add 15.6g trimethyl borate (0.15mol), dropwise, temperature control -75℃~-85℃ for 30 minutes, then naturally warm to -20℃, dropwise add 300ml hydrochloric acid aqueous solution . Separation, the aqueous phase was extracted twice with 200ml×2 ethyl acetate, the organic phase was combined, and spin-dried to obtain 16.4g of white solid, the liquid phase purity (LC) was 98%, the theoretical yield was 18.6g, and the yield was 88%;

[0113] 2) Synthesis of 2,3-difluoro-5,6-dimethyl-2',3'-difluoro-4'-butoxybiphenyl (compound 2-3)

[0114] Add 40mL ...

Embodiment 3

[0125]

[0126] 1) Synthesis of 3,4-dimethylphenylboronic acid (compound 3-2)

[0127] Add 18.5g of 3,4-difluorobromobenzene (compound 3-1, 0.1mol) and 500ml of tetrahydrofuran into a 1L dry and clean three-necked flask, and react with 2.64g of magnesium chips (0.11mol) under nitrogen protection, reflux for 1h, and then cool down To -30--40 degrees, dropwise add 16g of trimethyl borate (0.15mol), after dropping, raise the temperature to -10 degrees, then add dropwise 200ml of hydrochloric acid aqueous solution. Separation, the aqueous phase was extracted twice with 100ml×2 ethyl acetate, the organic phases were combined, and spin-dried to obtain a white solid, the liquid phase purity (LC) was 99.0%, the theoretical yield was 15g, the actual yield was 13g, and the yield was 86%;

[0128] 2) Synthesis of 3-fluoro-4-bromo-3',4'-dimethylbiphenyl (compound 3-3)

[0129] Add 26mL of absolute ethanol, 50mL of toluene and 50mL of water into a 200mL three-necked flask, start stirri...

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PUM

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Abstract

The invention relates to the field of liquid crystal display, in particular to a compound which can be used as a liquid crystal medium. The compound has a structure as shown in a general formula I, wherein R1 is selected from H and alkyl or alkoxy which contains 1-12 carbon atoms, wherein the alkyl or alkoxy is non-substituted, or one or more Hs of the alkyl or alkoxy are substituted by halogens; the R1 is preferably methyl; R2 is selected from H, F and alkyl or alkoxy which contains 1-12 carbon atoms, wherein alkyl or alkoxy is non-substituted, or one or more Hs of the alkyl or alkoxy are substituted by halogens; the R2 is preferably selected form alkyl or alkoxy which contains 1-6 carbon atoms; the halogens are selected from fluorine, chlorine, bromine and iodine, and is preferably fluorine; A1 and A2 are respectively and independently selected from 1,4-cyclohexyl or 1,4-phenyl, wherein the Hs in the 1,4-phenyl are respectively and independently substituted by one or more Fs; a, b and c respectively and independently represent 0 or 1, and the sum of the a, the b and the c is more than 0 and less than or equal to 3. After the compound provided by the invention is added into a liquid crystal composition, the liquid crystal composition has the advantages of being low in rotary viscosity, high in negative dielectric anisotropy, high in optical anisotropy and high in clearing point, thus having wide application prospect. The formula I is described in the description.

Description

technical field [0001] The invention relates to the field of liquid crystal display materials, in particular to a liquid crystal compound containing 2,3-difluoro-5,6-dimethylphenyl, a preparation method and application thereof. Background technique [0002] At present, liquid crystals are widely used in the field of information display, and at the same time, some progress has been made in the application in optical communication (S.T.Wu, D.K.Yang. Reflective Liquid Crystal Displays. Wiley, 2001). In recent years, the application fields of liquid crystal compounds have been significantly expanded to various display devices, electro-optic devices, electronic components, sensors, etc. For this reason, many different structures have been proposed, especially in the field of nematic liquid crystals, and nematic liquid crystal compounds have been most widely used in flat panel displays so far. Especially for TFT active matrix systems. [0003] According to the arrangement of liq...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/30C09K19/12C07C17/263C07C25/13C07C41/30C07C43/225G02F1/1333
CPCC07C17/2632C07C25/13C07C41/30C07C43/225C09K19/12C09K19/3003C09K2019/122C09K2019/123C09K2019/3009C09K2019/3016G02F1/1333
Inventor 储士红班全志姜天孟田会强谭小玉高立龙苏学辉陈海光
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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