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Liquid crystal composition containing difluoromethoxy bridged bond and application thereof

A technology of difluoromethoxy bridges and liquid crystal compounds, which is applied in the field of liquid crystal display materials and can solve problems such as unobtained compounds

Active Publication Date: 2014-09-24
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As early as 1992, German Merck Co., Ltd. described the monomeric liquid crystal with the terminal -O(CH2)nF in the patent DE4222371, but did not obtain the ideal corresponding compound

Method used

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  • Liquid crystal composition containing difluoromethoxy bridged bond and application thereof
  • Liquid crystal composition containing difluoromethoxy bridged bond and application thereof
  • Liquid crystal composition containing difluoromethoxy bridged bond and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]

[0061] 4-{[3,5-difluoro-4-(3-fluoropropoxy)-phenoxy]-difluoromethyl}-3,5-difluoro-4'-propylbiphenyl (compound 6 )Synthesis

[0062] 1) Synthesis of 5-benzyloxy-1,3-difluoro-2-(3-fluoropropoxy)-benzene (compound 2)

[0063]

[0064] Add 22mL of N,N-dimethylformamide into a 50mL reaction bottle, start stirring, add 5.9g of 2,3-difluoro-4-bromophenol (compound 1), after the solid is completely dissolved, add 10mL of water, 0.25g Tetrabutylammonium bromide, 4.0g anhydrous potassium carbonate. Heat to raise the temperature, add 4.0g of 3-fluorobromopropane dropwise under temperature control at 65-72°C, stir for 4 hours, add 10mL of toluene and 15mL of water, stir for 10 minutes, let stand to separate the liquids, and extract the water phase twice with 5mL×2 toluene ( Stir for 2 minutes, let stand for 5 minutes), and discard the water. All organic phases were combined and washed three times with 10 mL×3 water. The solvent was spin-dried to obtain a white solid, th...

Embodiment 2

[0083] 2-(4-{[3,5-difluoro-4-(3-fluoropropoxy)-phenoxy]-difluoromethyl}-3,5-difluorophenyl)-5-propyl Synthesis of -[1,3]dioxane (Compound 9)

[0084] 1) Synthesis of onium trifluoromethanesulfonate (compound 8)

[0085]

[0086] Add 106g of 2,6-dioxo-4-(5-propyl-[1,3]dioxocyclohexane-2-yl)-benzoic acid (compound 7), 47mL of 1,3-propanedi Mercaptan, 42mL of trifluoromethanesulfonic acid, 145mL of toluene and 145mL of isooctane, install a water separator at one port, raise the temperature to reflux, react for 6 hours, slowly cool to 0°C, and suction filter to obtain a solid. After drying, proceed to the next step of feeding.

[0087] 2) 4-{[3,5-difluoro-4-(3-fluoropropoxy)-phenoxy]-difluoromethyl}-3,5-difluoro-4'-propyl biphenyl ( Compound 9) Synthesis

[0088]

[0089] Add 200mL of dichloromethane, 39mL of triethylamine and 57.7g of 3,5-difluoro-4-(3-fluoropropoxy)-phenol (compound 3) into a 2L three-necked flask, cool down to 20°C, add 120g of trifluoro A solution c...

Embodiment 3

[0098] 4-{[3,5-Difluoro-4-(3-fluoropropoxy)-phenoxy]-difluoromethyl}-3,5,2'-trifluoro-4''-propyl- Synthesis of [1,1'; 4',1'']terphenyl (compound 12)

[0099] 1) Synthesis of onium trifluoromethanesulfonate (compound 11)

[0100]

[0101]

[0102] Add 137g 3,5,2'-trifluoro-4''-propyl-[1,1'; 4',1'']terphenyl-4-carboxylic acid (compound 10), 47mL1,3- Propanedithiol, 42mL trifluoromethanesulfonic acid, 145mL toluene, and 145mL isooctane were installed with a water separator at one port, heated to reflux, reacted for 6 hours, cooled slowly to 0°C, and filtered with suction to obtain a solid. After drying, proceed to the next step of feeding.

[0103] 2) 4-{[3,5-difluoro-4-(3-fluoropropoxy)-phenoxy]-difluoromethyl}-3,5-difluoro-4'-propyl biphenyl ( Compound 12) Synthesis

[0104]

[0105] Add 200mL of dichloromethane, 39mL of triethylamine and 57.7g of 3,5-difluoro-4-(3-fluoropropoxy)-phenol (compound 3) into a 2L three-necked flask, cool down to 20°C, and add 142g of...

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Abstract

The invention provides a liquid crystal composition containing a difluoromethoxy bridged bond and a -O(CH2)nF unit structure. The liquid crystal compound has a structure shown in a formula I as follows: R-Al-Z1-A2-Z2-A3-CF2O-A4-Z3-A5-O(CH2)n-CH2F(I); the compound has the characteristics of being low in rotary viscosity and great in dielectric anisotropy; after the liquid crystal composition is applied, the dielectric anisotropy of the existing idiomatic liquid crystal composition can be further improved, and therefore, the liquid crystal composition has technical effect of lowering drive voltage of an apparatus.

Description

technical field [0001] The invention relates to the field of liquid crystal display materials, in particular to a 2 ) liquid crystal compound with nF unit structure and its application. 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] Liquid crystal display has experienced a long development path with the disc...

Claims

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Application Information

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IPC IPC(8): C09K19/34C09K19/20C09K19/30C07C43/225C07C41/09C07D319/12G02F1/1333
Inventor 姜天孟杭德余田会强储士红陈海光高立龙班全志
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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