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CF2S bridged bond-containing liquid crystal monomeric compound and synthesis method

A technology of liquid crystal monomers and compounds, applied in the field of liquid crystal, can solve the problems of instability, affect the performance of liquid crystal, easy to decompose in contact with air, etc., and achieve the effects of easy availability of raw materials and simple synthesis route.

Active Publication Date: 2015-06-17
XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low viscosity of ester liquid crystals, it has been widely used, but it is unstable and easy to decompose when exposed to air, thus affecting the performance of liquid crystals

Method used

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  • CF2S bridged bond-containing liquid crystal monomeric compound and synthesis method
  • CF2S bridged bond-containing liquid crystal monomeric compound and synthesis method
  • CF2S bridged bond-containing liquid crystal monomeric compound and synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthetic route of compound 3', 5'-difluoro-4''-propylbiphenyl-difluoromethylene-3,4-difluorothiophenol is as follows:

[0028]

[0029]

[0030] Step 1: Synthesis of 3,5-difluoro-4'-propylbiphenyl:

[0031] On the 10L three-necked flask, install a stirrer and a thermometer in sequence, and after replacing the system with nitrogen, add 4-propylphenylboronic acid: 764g, 3,5-difluorobromobenzene: 855.8g, potassium carbonate: 1224g, TBAB: 355.8g, Pd(PPh 3 ) 2 Cl 2 : 15.6g, ethanol: 2L, toluene: 2L, water: 2L, stirred, heated, reacted for 1 hour, stopped the reaction, and cooled to room temperature.

[0032] Add 2L each of toluene and water into a 10L reaction flask, stir for 15min, let stand, separate liquids, extract the water phase with toluene, combine the organic phases, wash with water until neutral, discard the water phase, dry the organic phase, filter, and concentrate to obtain The crude product was purified to obtain 1010 g of 3,5-difluoro-4'-propylb...

Embodiment 2

[0049] Synthesis of the compound 4'-propylbiphenyl-difluoromethylene-3,4-difluorothiophenol:

[0050]

[0051] Step 1: Synthesis of 4'-propyl-4-difluorobromomethylbiphenyl:

[0052] On a 1L three-necked flask, install a stirrer, a low temperature thermometer, a constant pressure dropping funnel, and a nitrogen replacement system, add 4'-propyl-4-bromobiphenyl: 52g, THF: 500mL, and stir under nitrogen protection. Cool down to -78°C with liquid nitrogen, start to drop n-BuLi: 100mL, after the dropwise addition, keep warm (-78°C) for 1h reaction, add dropwise 160g of 50% THF solution of difluorodibromomethane, after the dropwise addition, naturally Bring to room temperature.

[0053] The reaction solution was concentrated, petroleum ether was added to the concentrated solution, stirred for 30 minutes, washed with water until neutral, left to stand, separated, the organic phase was dried, filtered and concentrated to obtain 4'-propyl-4-difluorobromomethylbiphenyl Crude produc...

Embodiment 3～6

[0065] Referring to Example 1, the 4-propylphenylboronic acid in step 1 was replaced with 4-methylphenylboronic acid, 4-ethylphenylboronic acid, 4-n-butylphenylboronic acid and 4-n-pentylphenylboronic acid, and other raw materials Same as the operation, the following compounds are obtained:

[0066]

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Abstract

The invention discloses a -CF2S- bridged bond-containing liquid crystal monomeric compound and a preparation method thereof. The liquid crystal monomeric compound has a structural general formula, wherein R is C1-C10 linear alkyl, X1, X2, X3 and X4 are H or F, and Y is one of H, F, CF3 and OCF3. The preparation method comprises Suzuki reaction, low-temperature bromination and etherification reaction. According to the liquid crystal monomeric compound and the preparation method, raw materials are readily available, a synthesis route is simple, and the liquid crystal monomeric compound and the preparation method are suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of liquid crystal technology, and relates to a class of liquid crystals containing -CF 2 The liquid crystal monomer compound of S-bridge bond and its synthesis method are suitable for a key component of TFT liquid crystal mixture with high-speed response and low voltage threshold. Background technique [0002] For the liquid crystal material used in TFT-LCD, in addition to requiring low threshold value, fast response and high liquid crystal stability, a high voltage retention rate is also required. The low-threshold liquid crystal material should have a large dielectric anisotropy (△ε), and the fast response performance requires the liquid crystal to have a small rotational viscosity (γ 1 ). Among them, the key bridge links are ethane, ester, alkyne, -CH 2 O-, -OCH 2 -, -CH 2 CF 2 -, -CF 2 CH 2 -and-CF 2 O-etc. Ester liquid crystals have been widely used due to their low viscosity, but they are unstable and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/09C07C323/20C07C319/14C09K19/28
Inventor 别国军杨学军杜渭松高嫒嫒宋宽广刘小岐张延魏徐磊张旺财辛兴东邓登
Owner XIAN CAIJING OPTO ELECTRICAL SCI & TECH