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Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof

A compound and liquid crystal technology, applied in chemical instruments and methods, organic chemistry, liquid crystal materials, etc.

Active Publication Date: 2013-04-24
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no single liquid crystal monomer has been used alone in liquid crystal displays without being combined with other compounds to meet the performance requirements.

Method used

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  • Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof
  • Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof
  • Liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065]

[0066] step 1:

[0067]

[0068] Add 0.1mol 4-propylbenzofuran (reactant) and 80ml tetrahydrofuran (solvent) to the reaction flask, protect it with nitrogen, cool down to -10°C, add 0.1mol n-butyllithium (reactant) petroleum ether dropwise (Solvent) solution, the dropwise addition is completed within 1 hour, and the negative ionization reaction is carried out with stirring at 0°C for 30 minutes. Then cool down to -30°C, add dropwise 0.11mol iodine (reactant) in 70ml tetrahydrofuran (solvent) solution within 1 hour. Sodium hydrogen aqueous solution (reducing agent) to remove excess iodine in the reaction, add water to wash, extract petroleum ether (solvent) and separate liquids, wash the organic phase with water until neutral, evaporate the solvent to dryness, distill under reduced pressure, collect 132 ℃ ~ 134 ℃ / 2mmHg fraction to obtain compound (1-a) with a yield of 85% and a purity of 97% by gas chromatography.

[0069] Step 2:

[0070]

[0071] Add 0.0...

Embodiment 2

[0088] According to the 4-step reaction of Example 1, the 3,5-difluorophenylboronic acid in step 2 is replaced by 2-fluoro-3', 5'-difluorobiphenylboronic acid, and the products are fed and reacted sequentially downwards. In step 4 The following compounds were prepared by substituting 3,4,5-trifluorophenol for 3,5-difluoro-4-trifluoromethylphenol.

[0089]

[0090] Wherein, the intermediates of each step are respectively

[0091] step 1

[0092]

[0093] step 2

[0094]

[0095] step 3

[0096]

[0097] step 4

[0098]

[0099] The experimental results are as follows:

[0100] 1. GC: 99.8%

[0101] 2. MS: m / z%189(6.77)262(3.91)386(9.44)468(100)612(M + 0.56)

[0102] 3. MP: 146.5°C

[0103] As can be seen from the above, the product has a correct structure and is a compound shown in formula I12. The test results of its liquid crystal performance are as follows:

[0104] 4. △ε: 21.3 (20°C, 1000Hz)

[0105] 5. △n: 0.22 (20°C, 589nm)

[0106] 6. CP: 148°C ...

Embodiment 3~44

[0108] With reference to the method of Example 1 and 2, only the reactant substituent is replaced according to the corresponding product, and the compound shown in the following formula I is obtained:

[0109]

[0110]

[0111]

[0112]

[0113]

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Abstract

The invention discloses a liquid crystal compound containing benzoxazole and difluoromethylenedioxy bridged linkage (-CF2O-) and a preparation method and application of the liquid crystal compound. The structural general formula of the compound is as formula I. The compound is relatively stable in structure, and has a wide temperature range of the liquid crystal state, good intersolubility at low temperature and large positive dielectric anisotropy delta epsilon. When the compound is used in an optical element, low threshold voltage and small rotary viscosity gamma can be achieved. Thus, the material of a liquid crystal composition and the performance of a display can be improved, and the liquid crystal compound containing benzoxazole and the difluoromethylenedioxy bridged linkage plays a significant role in the achievement of rapid response of the display. A liquid crystal composition containing the compound can be applied to the production of a liquid crystal display which is low in driving voltage, wide in temperature range and rapid in response.

Description

technical field [0001] The invention belongs to the field of liquid crystal compounds and applications, and relates to a compound containing benzofuran and difluoromethyleneoxy bridge (-CF 2 O-) liquid crystal compound and its preparation method and application. Background technique [0002] For the field of liquid crystal display technology, although the market has become very large in recent years and the technology has gradually matured, people's requirements for display technology are also constantly improving, especially in terms of achieving fast response and reducing driving voltage to reduce power consumption. As one of the important optoelectronic materials of liquid crystal display, liquid crystal material plays an important role in improving the performance of liquid crystal display. [0003] As a liquid crystal material for display, it has been greatly developed, and a large number of liquid crystal compounds have appeared. From biphenylnitrile, esters, oxygen-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80C07D407/04C09K19/44C09K19/34G02F1/1333
Inventor 丰景义夏治国华瑞茂韩耀华温刚贾刚刚
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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