Terminal alkenyl-containing negative liquid crystal compound and synthesis method thereof

A technology of negative liquid crystal and synthesis method, which is applied in the field of negative liquid crystal compound and its synthesis, can solve the problem that the liquid crystal display cannot well satisfy the low voltage driving fast response, poor low temperature stability, low clearing point and low optical anisotropy, etc. question

Active Publication Date: 2020-07-07
JIANGSU HECHENG ADVANCED MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The invention application with the publication number WO2018107911A1 discloses a liquid crystal compound with negative dielectric anisotropy, and the invention application with the publication number CN108728116A discloses a liquid crystal composition and its display device, but contains two documents disclosed The liquid crystal compositions of the compounds all have the shortcomings of low clearing point, low optical anisotropy, and poor low temperature stability, which cannot well meet the needs of low-voltage drive and fast response of liquid crystal displays.

Method used

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  • Terminal alkenyl-containing negative liquid crystal compound and synthesis method thereof
  • Terminal alkenyl-containing negative liquid crystal compound and synthesis method thereof
  • Terminal alkenyl-containing negative liquid crystal compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Step (1), in a 500mL three-necked flask, add 12.1g (50mmol) 2,2', 3,3'-tetrafluoro[1,1'-biphenyl]-4-phenol, 6.7g (55mmol) 1- Chloro-4-methoxybutane and 13.8g (100mmol) of potassium carbonate were fully dissolved in 50mL of N,N-dimethylformamide, heated to an external temperature of 90°C, and reacted for 5 hours;

[0121] Cool, add 150mL water and 100mL ethyl acetate to separate the liquid, extract the aqueous phase with 2×100mL ethyl acetate, combine the organic phases, wash with 3×80mL water, dry, and spin dry;

[0122] Spread 20 g of 200 mesh silica gel, pass the organic phase through the column, and evaporate the solvent to dryness at 50° C. to obtain 18 g of red liquid. Add 40mL of ethanol to recrystallize at -30°C for 3h, filter with Buchner funnel to obtain 12.5g of white solid (compound 3-1: 2,2',3,3'-tetrafluoro-4-(4-methoxybutoxy base)-1,1'-biphenyl), purity 99.1%, yield 76.2%; its mass spectrum is as figure 1 shown; 1 HNMR (δ, ppm, CDCl 3 ,500MHz):1.48(m, ...

Embodiment 2

[0138] Step (1), in a 500mL three-necked flask, add 12.1g (50mmol) 2,2', 3,3'-tetrafluoro[1,1'-biphenyl]-4-phenol, 6.7g (55mmol) 1- Chloro-4-methoxybutane and 13.8g (100mmol) of potassium carbonate were fully dissolved in 50mL of isopropanol, heated to an external temperature of 90°C, and reacted for 5 hours;

[0139] Cool, add 150mL water and 100mL ethyl acetate to separate the liquid, extract the aqueous phase with 2×100mL ethyl acetate, combine the organic phases, wash with 3×80mL water, dry, and spin dry;

[0140] Spread 20g of 200 mesh silica gel, pass the organic phase through the column, and evaporate the solvent to dryness at 50°C to obtain 15g of red liquid. Add 40 mL of ethanol for recrystallization and freeze at -30°C for 3 h, and suction filter through a Buchner funnel to obtain 12.1 g of a white solid (compound 3-1: 2,2',3,3'-tetrafluoro-4-(4-methoxybutoxy base)-1,1'-biphenyl), purity 98.8%, yield 74.1%; its mass spectrum and main 1 H-NMR is the same as compound...

Embodiment 3

[0156] Step (1), in a 500ml three-necked flask, 24.2g (100mmol) 2,2', 3,3'-tetrafluoro[1,1'-biphenyl]-4-phenol, 12.3g (100mmol) 1- Chloro-4-methoxybutane and 24g (170mmol) of potassium carbonate were fully dissolved in 100mL of N,N-dimethylformamide, heated to an external temperature of 120°C, and reacted for 2 hours;

[0157] Cool, add 180mL water and 120mL ethyl acetate to separate the liquid, extract the aqueous phase with 2×100mL ethyl acetate, combine the organic phases, wash with 3×80mL water, dry, and spin dry;

[0158] Spread 20g of 200 mesh silica gel, pass the organic phase through the column, evaporate the solvent to dryness at 50°C to obtain 36g of red liquid, add 40mL of ethanol to recrystallize at -30°C for 3 hours, and filter with Buchner funnel to obtain 24.7g of white solid (Compound 3-1: 2 ,2',3,3'-tetrafluoro-4-(4-methoxybutoxy)-1,1'-biphenyl), purity 98.5%, yield 75.3%; its mass spectrum and main 1 H-NMR is the same as compound 3-1 of Example 1.

[0159] ...

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Abstract

The present invention relates to a liquid crystal compound represented by formula A, a method for preparing the liquid crystal compound, and an intermediate used in the method for preparing the liquidcrystal compound and a method for producing the intermediate, wherein R1 is an alkenyl group having 2 to 12 carbon atoms, n is a positive integer of 1 to 12, and R2 is an alkyl group having 1 to 8 carbon atoms. The liquid crystal compound is prepared with 2,2',3,3'-tetrafluoro[1,1'-biphenyl]-4-phenol as a raw material through the steps of substitution, halogenation, boronation, coupling, oxidation, ylide reaction and the like. The preparation method has the advantages of common and readily available reagents, low price, simple and clear steps, convenience and safety in operation and higher yield. The liquid crystal composition composed of the compound has a high clearing point, a high absolute value of negative dielectric anisotropy, high optical anisotropy and good low-temperature stability, and can meet the requirements of low-voltage driving and quick response when being applied to a liquid crystal display.

Description

technical field [0001] The invention relates to a liquid crystal compound, in particular to a negative liquid crystal compound containing terminal alkenyl groups and a synthesis method 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 a liquid crystal display method, among its representative methods, PC (phase change, phase change), TN (twist nematic, twisted nematic), STN (supertwisted nematic, super twisted nematic), ECB (electrica11y controlled birefringence, electrically controlled birefringence), OCB (optica11 y compensated bend, optical compensation bending), IPS (in-p1ane switching, coplanar transformation), VA (vertica1 a1ignment, vertical alignment), CSH (co1or super homeotropic, color super vertical Surface) and other class modes. According to the d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/12C07C41/16C07C41/18C07C41/22C07C41/30C07C43/225C07C43/23C07C45/29C07C47/277C07F5/02C09K19/44
CPCC09K19/12C07C43/225C07C43/23C07C47/277C07C41/18C07C41/30C07C45/29C07C41/22C07C41/16C07F5/025C09K19/44C09K2019/123Y02E60/10
Inventor 徐爽陈法兵赵李亮吴川
Owner JIANGSU HECHENG ADVANCED MATERIALS
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