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Cyclohexane oxane liquid crystal monomer compound and preparation method thereof

A technology of cyclohexaneoxane and liquid crystal monomer is applied in the field of cyclohexaneoxane liquid crystal monomer compound and its preparation, which can solve the problem that the dielectric anisotropy coefficient cannot independently satisfy the liquid crystal display, etc. Effects of electrical coefficients, pitch length, and phase transition temperature

Active Publication Date: 2018-01-12
SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these properties are related to the structural characteristics of the liquid crystal material itself. The current liquid crystal materials cannot independently meet the needs and must be mixed and compounded for use. The display needs can only be met by mixing monomers. It has the advantage of low viscosity, but its dielectric anisotropy coefficient cannot independently meet the needs of liquid crystal display

Method used

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  • Cyclohexane oxane liquid crystal monomer compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of Grignard reagents:

[0043] Weigh 100mL tetrahydrofuran, 24g magnesium powder, 0.3g iodine, 3.9g 2-bromo-4,5-difluoro-benzyl sulfide, stir, let stand at 20-25°C for 30min, then add 0.33g / mL of 2-bromo-4,5-difluoro-benzyl sulfide in tetrahydrofuran 60mL, reflux reaction at 66°C for 1h, the Grignard reagent can be generated, the structural formula is: .

[0044] Wherein, the structural formula of 2-bromo-4,5-difluoro-benzyl sulfide is:

[0045] .

[0046] During the implementation, just weigh tetrahydrofuran, magnesium powder, iodine, 2-bromo-4,5-difluoro-benzyl sulfide, tetrahydrofuran and 2 The volume ratio of bromo-4,5-difluoro-benzyl sulfide in tetrahydrofuran is 5:3, and the Grignard reagent can be prepared by the above method.

Embodiment 2

[0048] 1. a cyclohexane oxane liquid crystal monomer compound, the structural formula of the compound is:

[0049] ,

[0050] Wherein, R is H, and the structural formula of the cyclohexane-based liquid crystal monomer compound is:

[0051] , is compound V1.

[0052] 2. The preparation method of the cyclohexane oxane liquid crystal monomer compound comprises the following steps:

[0053] (1) Weigh 150mL of the Grignard reagent prepared in Example 1 and 50mL of a THF solution of 4-(5-phenyl-1,3-oxanyl-2-yl)cyclohexanone with a concentration of 0.52g / mL , reflux at 66°C for 2 hours to obtain intermediate 1 with a conversion rate of 73.3%, a yield of 57.2%, and a purity of 97% by HPLC;

[0054] (2) Weigh 250mL of dichloroethane, 40g of intermediate 1, 20g of p-toluenesulfonic acid, 20mL of 30% hydrogen peroxide, and react at 75°C for 8 hours to obtain intermediate 2 with a conversion rate of 73.3% and a yield of 62.1 %, purity HPLC=98%;

[0055] (3) Weigh 250mL of dichlor...

Embodiment 3

[0072] 1. a cyclohexane oxane liquid crystal monomer compound, the structural formula of the compound is:

[0073] ,

[0074] Wherein, R is fluorine, and the structural formula of the cyclohexane-based liquid crystal monomer compound is:

[0075] , is compound V3.

[0076] 2. The preparation method of the cyclohexane oxane liquid crystal monomer compound comprises the following steps:

[0077] (1) Weigh 180 mL of the Grignard reagent prepared in Example 1, 50 mL of 4-(5-(4-fluorophenyl)-1,3-oxanyl-2-yl) ring with a concentration of 0.52 g / mL The THF solution of hexanone was refluxed at 60°C for 2 hours to obtain intermediate 1, the purity of which was detected by high performance liquid chromatography was 97%;

[0078] (2) Weigh 240mL of dichloroethane, 40g of intermediate 1, 30g of p-toluenesulfonic acid, 20mL of 30% hydrogen peroxide, and react at 70°C for 8 hours to obtain intermediate 2 with a purity of HPLC=99%;

[0079] (3) Weigh 250mL of dichloroethane, 40g of i...

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Abstract

The invention provides a cyclohexane oxane liquid crystal monomer compound and a preparation method of the cyclohexane oxane liquid crystal monomer compound. The structural formula of the compound isshown in the following formula, wherein R is any one of fluorine, chlorine, H, cyano, C1-C5 linear chain alkyl and C1-C5 linear alkoxy. The cyclohexane oxane liquid crystal monomer compound provided by the invention contains sulfonyl laterally and can change the phase transition temperature of molecules, the prepared monomer mixture not only has the advantage of low viscosity, but also has the characteristics of wide phase transition temperature and long screw pitch, and can be taken as raw materials of liquid crystal materials, thereby being beneficial to lowering the rotational viscosity ofthe liquid crystal materials and improving various dielectric coefficients.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a cyclohexane-based liquid crystal monomer compound and a preparation method thereof. Background technique [0002] Liquid crystal display technology has been widely used in daily life. The synthesis of its core material liquid crystal monomer has always been the focus of attention. With the update of liquid crystal display technology, display technology has attracted more and more attention. No matter what kind of liquid crystal Display mode, reducing the response time of liquid crystal, even if the liquid crystal panel has a faster refresh rate, has always been an important goal that manufacturers are constantly pursuing. The key to reducing the liquid crystal response time is to reduce the rotational viscosity of the liquid crystal material and increase the dielectric anisotropy coefficient of the liquid crystal material. However, these properties ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/34C07D319/06
Inventor 高昌轩田婧杨凯凯王卫军陈志伟薛震王亚龙
Owner SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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