Fluorinated terphenyl liquid crystal compound containing two 3-butenyls and preparation method thereof

A technology of liquid crystal compounds and terphenyls, which is applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve problems such as poor stability of ultraviolet light, large birefringence, and unstable water, and achieve large birefringence , high-definition highlights, the effect of mild reaction conditions

Inactive Publication Date: 2011-08-17
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. It has large birefringence, high-definition bright spots, large K33 / K11 value, but poor miscibility
[0006] 2. It has a large birefringence index, good mutual solubility, large K33 / K11 value, but low clearing point, and poor stability to ultraviolet light
[0007] 3. The birefringence is very large, the clearing point is relatively high, and the K33 / K11 value is relatively large, but the miscibility is relatively poor, and it is unstable to water

Method used

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  • Fluorinated terphenyl liquid crystal compound containing two 3-butenyls and preparation method thereof
  • Fluorinated terphenyl liquid crystal compound containing two 3-butenyls and preparation method thereof
  • Fluorinated terphenyl liquid crystal compound containing two 3-butenyls and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of 4,4''-bis(3-butenyl)-3',5'-difluoro-(1,1',4',1'')terphenyl.

[0041] step 1 Preparation of 4,4''-bisformyl-3',5'-difluoro-(1,1',4',1'')terphenyl:

[0042] Add 36.6g of 2,6-difluoro-1,4-diiodobenzene, 36g of p-formylphenylboronic acid, 300ml of toluene, 200ml of ethanol, 200ml of water into a 1000ml three-necked flask, replace the air with nitrogen, and add tetrakistriphenylphosphine palladium 1.6 g, heated to reflux with stirring for 6 hours.

[0043] Remove the inorganic salts in the reaction solution by filtration while it is hot, wash the filter cake with hot toluene, separate the filtrate to remove the water layer, wash the organic layer with hot water, and freeze it in the refrigerator. The precipitated crystals were filtered to obtain 24.6 g of pale yellow crystals.

[0044] step 2 Preparation of 4,4''-bishydroxymethyl-3',5'-difluoro-(1,1',4',1'')terphenyl

[0045] Add 24.6g of 4,4''-bisformyl-3',5'-difluoro-(1,1',4',1'') terphenyl and 400ml...

Embodiment 2

[0057] Preparation of 4,4''-bis(3-butenyl)-2',3'-difluoro-(1,1',4',1'')terphenyl

[0058] Referring to the preparation method similar to Example 1, the initial raw material is coupled with p-formylphenylboronic acid and 2,3-difluoro-1,4-diiodobenzene, and after four steps of reaction as in Example 1, it can be prepared 4,4''-bis(3-butenyl)-2',3'-difluoro-(1,1',4',1'')terphenyl

Embodiment 3

[0060] Preparation of 4,4''-bis(3-butenyl)-3',6'-difluoro-(1,1',4',1'')terphenyl

[0061] Referring to the preparation method similar to Example 1, the initial raw material is coupled with p-formylphenylboronic acid and 2,5-difluoro-1,4-diiodobenzene, and after four steps of reaction as in Example 1, it can be prepared 4,4''-Bis(3-butenyl)-3',6'-difluoro-(1,1',4',1'')terphenyl is obtained.

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Abstract

The invention relates to a novel monomeric fluorinated terphenyl liquid crystal compound containing two 3-butenyls and a preparation method thereof. The monomeric fluorinated terphenyl liquid crystal compound containing two 3-butenyls and intermediates thereof are applicable to compound structural formulae (I) and (II). In the formulae (I) and (II), the number of fluorine atoms is two, and the two fluorine atoms can be in ortho-position, or meta-position or para-position; and X1 and X2 are iodine or bromine. The preparation method comprises the following steps: carrying out cross-coupling reaction on p-formylphenylboronic acid and the (II) under the catalytic action of a palladium catalyst in the alkaline environment to obtain a 4,4''-diformyl fluorinated terphenyl; and carrying out reduction, chlorination and coupling reaction to obtain the (I). The novel monomeric terphenyl liquid crystal compound provided by the invention has the advantages of moderate synthesis conditions, high conversion rate and low cost.

Description

technical field [0001] The invention belongs to the field of liquid crystal materials and chemical technology, and in particular relates to the structure and preparation method of a novel liquid crystal compound, especially a novel compound containing bis-3-butenyl fluorine that can be widely used in STN-LCD and TFT-LCD Terphenyl liquid crystal compound and its preparation method. Background technique [0002] Since the discovery of liquid crystal materials by Austrian scientists in 1888, liquid crystal materials have been developed on a large scale. They are not only widely used in instrument displays and vehicle displays, but also with the development and application of TFT, they have been widely used in large-screen displays such as TVs. It is more and more closely related to people's life, so the performance requirements of liquid crystal materials are getting higher and higher. The commonly seen TN mode requires a wide range of nematic phases, low threshold voltage, hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/12C07C17/263C07C25/24
Inventor 员国良贾刚刚梁志安韩耀华任惜寒尚洪勇
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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