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Liquid crystal compound, preparation method and applications thereof

A compound and reaction technology, applied in chemical instruments and methods, ether preparation, liquid crystal materials, etc., can solve the problems of no reports, the reduction of the clearing point of liquid crystal, and the space that restricts the improvement of the response speed of liquid crystal mixtures.

Active Publication Date: 2015-03-04
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

-CF 2 The introduction of O-groups will greatly reduce the clearing point of liquid crystals. When preparing liquid crystal mixtures, it is necessary to add high-viscosity high-definition point compounds to balance -CF 2 The decrease of the clearing point caused by the O-group severely restricts the room for improving the response speed of the liquid crystal mixture
In sharp contrast to this, unexpectedly, the compounds provided by the present invention will -CF 2 The O-group is optimized to -C(CF 3 )(F)O- group can well make up for the above shortcomings, and replace the two fluorine atoms of the terminal group with CF 3 The negative large steric hindrance group different from F not only ensures a certain dipole moment, thereby improving the dielectric anisotropy of liquid crystal molecules, but also greatly improves the clearing point, and the response speed of the prepared liquid crystal mixture is significantly improved, which is There is no report in the prior art, and the prior art does not provide corresponding technical inspiration or teaching

Method used

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  • Liquid crystal compound, preparation method and applications thereof
  • Liquid crystal compound, preparation method and applications thereof
  • Liquid crystal compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Compound I514 shown in embodiment 1, formula I (method 1)

[0072]

[0073] step 1

[0074]

[0075] 25g (69.8mmol) (I514-0), 14.8g (139.6mmol) of anhydrous sodium carbonate, 1L of 1,4-dioxane and 50ml of water were added to a 2L pressure-resistant reactor, and 0.57g (0.698mmol) was added PdCl 2 (dppf) catalyst, filled with nitrogen to replace the air, placed in a low-temperature tank and cooled with liquid nitrogen, when the temperature dropped to -80 °C, 32.5 g (0.28 mol) of gas chlorotrifluoroethylene was introduced, the reaction vessel was sealed, and the temperature was raised to 100 °C and stirred After reacting for 2 hours, cool to room temperature, add 200ml ethyl acetate and 50ml saturated aqueous ammonium chloride solution, separate the layers, extract the aqueous phase twice with 100ml ethyl acetate, and combine the organic layers.

[0076] The solvent was evaporated under reduced pressure, dissolved in petroleum ether, passed through a silica gel col...

Embodiment 2

[0094] Embodiment 2, compound I317 shown in preparation formula I (method 2)

[0095]

[0096] step 1

[0097]

[0098] In a 2L three-neck flask, under a nitrogen atmosphere, add 141.5g (0.5mol) of (I317-0), 400ml of tetrahydrofuran, place it in a low-temperature tank and cool it with liquid nitrogen, and when it drops to -80°C, slowly add 220ml (2.5 M, 0.55mol) n-butyllithium hexane solution, added in about 2 hours, continued to stir for 1 hour, and added 156g (0.6mol) of 1,1-dibromotetrafluoroethane dropwise to the solution under stirring. In 150ml of tetrahydrofuran solution, add for about 2.5 hours, the reaction is exothermic, and then stir for another 2 hours after the addition.

[0099] Add 300ml of dichloromethane for dilution, add 300ml of 2N dilute hydrochloric acid aqueous solution with stirring, and stir for 10 minutes. Separation, the aqueous phase was extracted three times with dichloromethane, the organic phases were combined, the solvent was evaporated u...

Embodiment 3

[0109] Embodiment 3, compound I499 shown in preparation formula I (method 2)

[0110]

[0111] step 1

[0112]

[0113] Add 32g (0.1mol) (I499-0) and 250ml tetrahydrofuran to a 1L three-necked flask, replace the air with nitrogen, place it in a low-temperature tank and cool it with liquid nitrogen, and when it drops to -78°C, add 44ml of 2.5M butyllithium solution dropwise ( 0.11mol), add in about 30 minutes, keep warm and stir for 1 hour, add 39g (0.15mol) of 1,1-dibromotetrafluoroethane dropwise into the reaction flask, and stir for 2 hours at -78°C. Add 200ml of dichloromethane for dilution, add 200ml of 2N dilute hydrochloric acid aqueous solution with stirring, and stir for 10 minutes. Separation, the aqueous phase was extracted three times with dichloromethane, the organic phases were combined, the solvent was evaporated under reduced pressure, dissolved in petroleum ether, passed through a silica gel column, washed with petroleum ether, and the solvent was evapor...

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Abstract

The present invention discloses a liquid crystal compound, a preparation method and applications thereof. According to the present invention, the compound is represented by a formula I, is the liquid crystal compound containing CF3 and F substituted oxymethane linking group -C(F)(CF3)O-, has the high dielectric anisotropy, and further concurrently has the extreme rapid response speed and the high clearing point, wherein the performance provides the extremely important significance for the blending of the liquid crystal mixture. The formula I is defined in the instruction.

Description

technical field [0001] The invention relates to a liquid crystal compound suitable for use as a liquid crystal material in a liquid crystal display, namely a trifluoromethylfluorooxymethane derivative, and a liquid crystal composition containing the derivative, belonging to the field of liquid crystal compounds and applications. Background technique [0002] At present, the application range of liquid crystal compounds is expanding more and more widely, and it can be applied to various types of displays, electro-optic devices, sensors, and the like. There are various types of liquid crystal compounds used in the above-mentioned display fields, among which nematic liquid crystals are most widely used. Nematic liquid crystals have been used in passive TN, STN matrix displays and systems with TFT active matrix. [0003] For the application field of thin film transistor technology (TFT-LCD), although the market has been huge in recent years and the technology has gradually matu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C41/16C07D309/06C09K19/30C09K19/34C09K19/20G02F1/1333
CPCC07C41/16C07C43/225C07C2601/14C07D309/06C09K19/20C09K19/3003C09K19/3066C09K19/3402C09K2019/3016C09K2019/343G02F1/13
Inventor 曹建华华瑞茂逄辉王士波
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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