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Liquid crystal compound having negative dielectric anisotropy and synthetic method and application thereof

An anisotropy and compound technology, which is applied in the field of liquid crystal compounds with negative dielectric anisotropy and their synthesis, can solve the problems of small negative dielectric anisotropy, poor mutual solubility of liquid crystal monomers, and high viscosity.

Active Publication Date: 2017-01-11
JIANGSU HECHENG DISPLAY TECHCO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This document also points out that the negative dielectric anisotropy compound of this type of side dicyano groups has the following disadvantages: 1) high viscosity; 2) poor miscibility with liquid crystal monomers; 3) poor photostability
[0011] Although the side fluorine-containing negative compounds such as Ref.2 and Ref.3 have avoided the disadvantages of dicyano negative compounds, they have caused the negative dielectric anisotropy value to be too small (Ref.2 dielectric anisotropy literature The value is -4.1, and the value of Ref.3 dielectric anisotropy literature is -6.0)

Method used

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  • Liquid crystal compound having negative dielectric anisotropy and synthetic method and application thereof
  • Liquid crystal compound having negative dielectric anisotropy and synthetic method and application thereof
  • Liquid crystal compound having negative dielectric anisotropy and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Compound Ⅰ-A-1-3-2 synthetic route is as follows:

[0115]

[0116] Among them, compound A, tetrahydrofurfuryl alcohol, and 4-iodo-2,3-difluorophenetole were all from Jiangsu Hecheng New Materials Co., Ltd.

[0117] 1) Synthesis of Compound B

[0118] Add 13g of compound A, 10.2g of tetrahydrofurfuryl alcohol, 31.4g of triphenylphosphine, and 250ml of dichloromethane into a 500ml three-necked flask. Under nitrogen protection, cool down to 0°C, and dropwise add 20.9g of diethyl azodicarboxylate ( DEAD) and 500ml of dichloromethane. After the dropwise addition, the mixture was naturally warmed to room temperature and continued to stir for 12 hours. Post-processing, column chromatography purified to obtain white solid compound B: 17.9g, yield: 84%, GC> 97%.

[0119]2) Synthesis of Compound C

[0120] Add 17.9g of compound B and 200ml of anhydrous THF into a 500ml three-necked flask, under the protection of nitrogen, cool down to -78°C, add 35ml of n-BuLi n-hexane sol...

Embodiment 2

[0137] Compound Ⅰ-A-2-3-3 synthetic route is as follows:

[0138]

[0139] 1) Synthesis of Compound E

[0140] Add 13g of compound A, 15.6g of propylcyclohexylmethanol, 31.4g of triphenylphosphine, and 250ml of dichloromethane into a 500ml three-necked flask. The mixed solution composed of ester (DEAD) and 500ml of dichloromethane, after the dropwise addition, was naturally warmed to room temperature, continued to stir for 12h, post-processing, and purified by column chromatography to obtain white solid compound E: 22g, yield: 82%, GC >97%.

[0141] 2) Synthesis of Compound F

[0142] Add 22g of compound E and 200ml of anhydrous THF to a 500ml three-necked flask, under the protection of nitrogen, cool down to -78°C, add 35ml of n-BuLi n-hexane solution (2.4mol / L) dropwise, after the dropwise addition, keep at -78°C Stirred for 1h, then added dropwise by 21g I 2 and 100ml of anhydrous TFT, after the dropwise addition, keep stirring at -78°C for 1h, then naturally warm up...

Embodiment 3

[0153] Compound I-A-1-3-2, Compound I-A-2-3-3, Compound I-A-3-3-2 were mixed with the host liquid crystal (host) according to the mass ratio of 10:90, The liquid crystal parameters of Compound I-A-1-3-2, Compound I-A-2-3-3 and Compound I-A-3-3-2 were tested by extrapolation method as shown in Table 3 below:

[0154] table 3

[0155] Δn Δε I(UV) LTS(-10℃) Ⅰ-A-1-3-2 0.107 -13.3 0.03 >168h Ⅰ-A-2-3-3 0.101 -11.5 0.03 >168h Ⅰ-A-3-3-2 0.183 -15.8 0.03 >168h host 0.08 5.0 0.02

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Abstract

The invention provides a liquid crystal compound having negative dielectric anisotropy and represented by the general formula I, wherein the liquid crystal compound has the advantages of large dielectric anisotropy absolute value, good intersolubility and good light stability and low-temperature stability; moreover, a preparation process of the liquid crystal compound represented by the general formula I has the advantages of easily obtained raw materials, and simple and feasible synthesis route, and is suitable for large-scale industrial production. The invention also provides a liquid crystal composition comprising the liquid crystal compound; the liquid crystal composition has large dielectric anisotropy, low threshold voltage, good intersolubility and good light stability and low-temperature stability.

Description

technical field [0001] The invention relates to a liquid crystal compound, especially a liquid crystal compound with negative dielectric anisotropy, a synthesis method and application thereof. Background technique [0002] Liquid crystal display elements can be used in various home appliances represented by clocks and electronic calculators, measuring equipment, automotive panels, word processors, computers, printers, televisions, and the like. As the night scene display method, among its representative methods, PC (phase change, phase change), TN (twist nematic, twisted nematic), STN (super twisted nematic, super twisted nematic), ECB (electrically controlled birefringence) can be cited. , electronically controlled birefringence), OCB (optically compensated bend, optically compensated bending), IPS (in-plane switching, coplanar transition), VA (vertical alignment, vertical alignment), CSH (color superhomeotropic, color super vertical surface), etc. class mode. According t...

Claims

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Application Information

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IPC IPC(8): C09K19/34C07D307/12C09K19/44G02F1/1333
Inventor 韩文明徐爽张文琦严加浩
Owner JIANGSU HECHENG DISPLAY TECHCO
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