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Liquid crystal compounds having negative dielectric anisotropy and applications thereof

An anisotropic, liquid crystal composition technology, applied in organic chemistry, liquid crystal materials, nonlinear optics, etc., can solve the problems of poor mutual solubility, high viscosity, and poor photostability of liquid crystal monomers

Active Publication Date: 2017-05-10
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 compounds having negative dielectric anisotropy and applications thereof
  • Liquid crystal compounds having negative dielectric anisotropy and applications thereof
  • Liquid crystal compounds having negative dielectric anisotropy and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Compound Ⅰ-A-7 synthetic route is as follows:

[0088]

[0089] 1) Synthesis of Compound B

[0090] In a 500ml three-necked flask, add 10g compound A (2,3-difluoro-4-ethoxyphenylboronic acid), 9.7g 2,3-difluorobromobenzene, 100ml toluene, 50ml ethanol, 50ml water, 21.2g sodium carbonate , under the protection of nitrogen, add 0.3g Pd(PPh3)4, heat to reflux for 6h, separate liquid, wash with water, column chromatography gives white solid compound B 11.5g, GC>97%, yield: 85.3%

[0091] 2) Synthesis of Compound C

[0092] In a 250ml three-neck flask, add 6.7g of compound B and 100ml of anhydrous tetrahydrofuran, under nitrogen protection, cool down to -78°C, add 10.5ml of n-butyllithium n-hexane solution (2.4mol / L) dropwise, keep stirring for 2h, drop Add a mixed solution of 1.8g tetrahydropyran-2-one (CAS#542-28-9) and 10ml anhydrous tetrahydrofuran, and control the temperature to -65~-70°C. After the dropwise addition, keep stirring for 1h , and then the reaction s...

Embodiment 2

[0109] The synthetic route of compound Ⅰ-E-7 is as follows:

[0110]

[0111] 1) Synthesis of Compound D

[0112] Into a 500ml three-necked flask, add 13.5g of compound B and 150ml of anhydrous tetrahydrofuran, under nitrogen protection, cool down to -78°C, add 20.8ml of n-butyl lithium in n-hexane solution (2.4mol / L) dropwise, after the dropwise addition, Continue to keep stirring at -78°C for 1.5h, then add dropwise a mixture of 13g of triisobutyl borate and 25ml of anhydrous tetrahydrofuran, after the dropwise addition, keep at -78°C, stir for 0.5h, naturally warm to room temperature, and post-process to obtain Off-white solid, compound D 11g, HPLC>95%, yield: 70%.

[0113] 2) Synthesis of Compound E

[0114] In a 500ml three-necked flask, add 11g of compound D, 150ml of dichloromethane, and 50ml of dioxane, cool down to 0°C, add 12ml of 30% hydrogen peroxide dropwise, and control the temperature within 10°C. After the dropwise addition, stir at room temperature for 3h...

Embodiment 3

[0120] Compound I-A-7, Compound I-A-1, Compound I-E-7, Compound V were mixed with the host liquid crystal (host) at a ratio of 10:90, and the liquid crystal parameters of each compound were tested by extrapolation method as shown in Table 2. Show:

[0121]

[0122] Table 2

[0123] Δn Δε gamma 1 Ⅰ-A-7 0.155 -9.8 291 Ⅰ-A-1 0.128 -8.2 208 Ⅰ-E-7 0.156 -12.2 454 Ⅴ 0.152 -9.6 439 host 0.08 5.0 116

[0124] Compared with compound V, the compound of the present invention has a low γ1 value when the dielectric anisotropy is close; and when the γ value is close, it has a larger absolute value of the dielectric anisotropy; the above examples The test data results show that the liquid crystal compound provided by the present invention can achieve the invention purpose of large dielectric anisotropy and low viscosity, so that the liquid crystal composition comprising the present invention has a faster response speed and a lower th...

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PUM

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Abstract

Liquid crystal compounds having negative dielectric anisotropy and shown as a general formula I are provided. The liquid crystal compounds have high dielectric anisotropy absolute values, low viscosity, good intersolubility, and good light stability and low-temperature stability. According to a preparation process of the liquid crystal compounds shown as the general formula I, raw materials are easily available, and a synthetic route is simple, feasible and suitable for large-scale industrial production. A liquid crystal composition comprising the liquid crystal compounds is also provided. The liquid crystal composition has good liquid crystal performance.

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, electronically controlled birefringence), OCB (optically compensated bend, optically compensated bending), IPS (in-plane switching, coplanar transformation), VA (vertical alignment, vertical alignment), CSH (color super homeotropic, color super vertical plane ) and other class patterns. According to th...

Claims

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Application Information

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IPC IPC(8): C09K19/34C09K19/44C07D309/04G02F1/137
Inventor 韩文明徐爽徐海彬王盼盼
Owner JIANGSU HECHENG DISPLAY TECHCO
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