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4,5-disubstituted phenanthrene and hydrophenanthrene liquid crystal compound and preparation method thereof

A technology of liquid crystal composition and compound, applied in the field of liquid crystal

Active Publication Date: 2017-01-11
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, no single compound has been used alone in the display device without being combined with other compounds to meet the performance requirements of the display. Therefore, in order to obtain various characteristics required by the display mode, it is necessary to mix a variety of liquid crystal compounds. use

Method used

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  • 4,5-disubstituted phenanthrene and hydrophenanthrene liquid crystal compound and preparation method thereof
  • 4,5-disubstituted phenanthrene and hydrophenanthrene liquid crystal compound and preparation method thereof
  • 4,5-disubstituted phenanthrene and hydrophenanthrene liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1 Compound 2-(2,3-difluoro-4-n-propylphenyl)-4,5-difluoro-7-(3,5-difluoro-4-trifluoromethoxyphenyl)phenanthrene preparation of

[0081]

[0082] The first step: the preparation of 2-amino-5-bromo-3-fluorobenzoic acid hydrobromide

[0083]

[0084] 153g of 2-amino-3-fluorobenzoic acid dispersed in 1500ml of chloroform, 175g of bromine dissolved in 150ml of chloroform was slowly added dropwise to the above chloroform solution, and stirred at room temperature overnight, filtered the next day, and the filter cake After washing with DCM and vacuum drying, 276 g of 2-amino-5-bromo-3-fluorobenzoic acid hydrobromide was obtained as a yellow powder.

[0085] The second step: Preparation of 4,4'-dibromo-6,6'-difluorobiphenyl-2,2'-dicarboxylic acid

[0086]

[0087] Dissolve 75g of copper sulfate pentahydrate in 300ml of water, add 230ml of 25% ammonia water under stirring, and cool to 0°C with an ice-salt bath. An aqueous solution prepared by 20.8 g of hydroxy...

Embodiment 2

[0115] Example 2 Preparation of compound 2-(3,5-difluoro-4-(trifluoromethoxy)phenyl)-4,5-difluorophenanthrene

[0116]

[0117] Step 1: Preparation of (4-bromo-6,6'-difluorobiphenyl-2,2'-yl)dimethanol

[0118]

[0119] 35g of 4,4'-dibromo-6,6'-difluorobiphenyl-2,2'-dicarboxylate was dissolved in 300ml of dry THF, and the clear solution was cooled to -20°C with a liquid nitrogen bath , slowly add 7g of lithium aluminum hydride in batches, keep stirring for 1 hour, slowly rise to room temperature, stir and react for 5 hours, add water and 20ml of 15% sodium hydroxide aqueous solution dropwise to the reaction solution to quench the reaction, suction filter , the filter cake was washed with THF, the filtrate was concentrated to dryness under reduced pressure, and the residue was separated and purified with a silica gel column to obtain 23.5 g of (4-bromo-6,6'-difluorobiphenyl-2,2'-yl)dimethanol, Yellow oil.

[0120] The second step: the preparation of 4-bromo-6,6'-difluoro...

Embodiment 3

[0134] Preparation of Example 3 Compound 4,5-bis(trifluoromethyl)-2-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene

[0135]

[0136] Step 1: Preparation of 6,6'-bis(trifluoromethyl)biphenyl-2,2'-dicarboxylic acid

[0137]

[0138] According to the same operation method as the second step of Example 1, 6,6' can be prepared by replacing 2-amino-5-bromo-3-fluorobenzoic acid hydrobromide with 2-amino-3-trifluoromethylbenzoic acid -Bis(trifluoromethyl)biphenyl-2,2'-dicarboxylic acid, a yellow solid was obtained.

[0139] The second step: Preparation of methyl 6,6'-bis(trifluoromethyl)biphenyl-2,2'-dicarboxylate

[0140]

[0141] According to the same operation method as the third step of Example 1, 6,6'-bis(trifluoromethyl)biphenyl-2,2'-dicarboxylic acid was used instead of 4,4'-dibromo-6,6'- Difluorobiphenyl-2,2'-dicarboxylic acid can be used to prepare methyl 6,6'-bis(trifluoromethyl)biphenyl-2,2'-dicarboxylate as white crystals.

[0142] The third step: Preparation...

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Abstract

The invention discloses a 4,5-di-substituted phenanthrene and hydrophenanthrene liquid crystal compound and a preparation method thereof. A structural general formula of the compound is as shown in a formula I. Two benzene rings in 2,7-di-substituted and 4,5-di-substituted or 4,5-bi(trifluoromethyl) substituted phenanthrene derivatives cannot freely rotate; substituent groups are kept on the same side, can be spontaneously oriented, do not need to rotate to the same side under the action of an external electric field; the liquid crystal compound has the characteristics of being large negative dielectric anisotropy delta epsilon value, high response speed, high clearing point, low viscosity and the like, and is especially suitable for liquid crystal mixtures. The formula is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of liquid crystals, and relates to a 4,5-disubstituted phenanthrene and hydrophenanthrene liquid crystal compound and a preparation method thereof. Background technique [0002] In recent years, fluorine-containing liquid crystal display materials have developed rapidly. Almost all the research and development of nematic liquid crystal materials use fluorine-containing liquid crystal compounds as the main components, which are used in TN-LCD, STN-LCD, PDLC, especially in TFT -LCD is even more indispensable. In optoelectronic components, to obtain a good contrast, a uniform liquid crystal plane direction is required. To achieve good liquid crystal orientation in the SA and SC phases, the liquid crystal material must have low viscosity and high spontaneous polarization to obtain short response time. Based on the use requirements of display devices, liquid crystal compounds should have suitable optical anisotropy, diel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225C07C41/30C07C25/22C07C17/263C07C17/35C07C69/75C07C67/08C07C17/354C07C17/32C07C41/09C09K19/32G02F1/1333
CPCC07C25/22C07C43/225C07C69/75C07C255/51C07C2601/04C07C2603/26C07D239/26C07D309/04C07D319/06C07D333/12C09K19/32C09K19/3458C09K19/3491C09K2019/328C09K2019/3422G02F1/1333
Inventor 曹建华郭剑华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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