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Liquid crystal compound containing dibenzofuran ring as well as preparation method and application thereof

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

Active Publication Date: 2018-09-14
西安晶奥量新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, limited by the liquid crystal material itself, the response time has become the main constraint factor for the development of high-performance display devices.

Method used

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  • Liquid crystal compound containing dibenzofuran ring as well as preparation method and application thereof
  • Liquid crystal compound containing dibenzofuran ring as well as preparation method and application thereof
  • Liquid crystal compound containing dibenzofuran ring as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] This embodiment provides a kind of liquid crystal compound a, its chemical formula is

[0067]

[0068] Its synthetic route is as follows:

[0069]

[0070]

[0071] The specific operation steps are as follows:

[0072] 1) Synthesis of a-1

[0073] Add 10g of 2-bromo-4-fluorophenol, 3.15g of sodium hydroxide, and 50g of water to a 250mL three-necked flask in sequence, stir until completely dissolved, add 8.6g of ethyl chloroformate dropwise, and react at room temperature for 1 hour after the dropwise addition. The lower product a-1 was obtained, 13.8 g, with a yield of 100% and a main content >99%.

[0074] 2) Synthesis of a-2

[0075] Add 13.8g of a-1 and 61.6g of concentrated sulfuric acid to a 250mL three-necked flask in turn, stir and cool down to 0°C, add 18.5g of potassium nitrate, control the temperature at 0°C, and react for 1 hour after adding, then pour the reaction solution into stirred ice water, Product a-2 was obtained by filtration, 16g, yiel...

Embodiment 2

[0098] This embodiment provides a kind of liquid crystal compound b, its chemical formula is

[0099]

[0100] Its synthetic route is as follows:

[0101]

[0102] The specific operation steps are as follows:

[0103] 1) The synthesis of a-10 is the same as in Example 1;

[0104] 2) Synthesis of b

[0105] Add 1.5g of a-10, 0.74g of 3,4,5-trifluorophenylboronic acid, 1.2g of potassium carbonate, 0.3g of tetrabutylammonium bromide, palladium catalyst, and 12g of toluene to a 100mL three-necked flask protected by nitrogen. Ethanol 1.5g, water 1.5g, heated to reflux for 1h, acidified with hydrochloric acid, washed with water and concentrated, recrystallized from toluene ethanol to obtain 0.3g of product, GC: 99%, yield 40%, its mass spectrum is as follows figure 2 shown.

[0106] The clearing point of compound b is 44°C, the birefringence is 0.1661, and the dielectric anisotropy is 20.13.

Embodiment 3

[0108] This embodiment provides a kind of liquid crystal compound c, its chemical formula is

[0109]

[0110] Its synthetic route is as follows:

[0111]

[0112] The specific operation steps are as follows:

[0113] 1) Synthesis of c-1

[0114] Add 5g of 2-bromo-4-fluoro-5-nitrophenol, 6.7g of 2-fluoro-4-propylphenylboronic acid, 1.7g of potassium carbonate, and 1.7g of tetrabutylammonium bromide to a 250mL three-necked flask protected by nitrogen. , palladium catalyst, 40g of toluene, 5g of water, 5g of ethanol, heated to reflux for 3h, extracted with hydrochloric acid, extracted with ethyl acetate, washed with water, and concentrated to obtain a crude product with a yield of 70% and a main content of >50%.

[0115] 2) Synthesis of c-2

[0116] Add 4g of c-1, 4.4g of potassium carbonate, and 20g of DMF to a 250mL three-necked flask in sequence, heat up to reflux for 5 hours, evaporate half of the DMF, pour the reaction solution into 10 times the water and stir, and...

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Abstract

The invention provides a liquid crystal compound containing a dibenzofuran ring. The liquid crystal compound has a structure as shown in the formula I in the description. The liquid crystal compound containing the dibenzofuran ring has larger dielectric anisotropy, lower rotational viscosity and higher clearing point, and the intersolubility among monomers is good, thereby being favorable for preparing a composition. A liquid crystal composition containing the liquid crystal compound has greater dielectric anisotropy, can more effectively reduce the driving voltage of a device, simultaneouslyhas lower rotational viscosity and shorter response time, has good chemical stability and thermal stability, has good application in a display device, and especially has good application in a displaydevice in a TFT mode.

Description

technical field [0001] The invention relates to the technical field of liquid crystal materials, and more specifically, to a liquid crystal compound containing a dibenzofuran ring, a preparation method and application thereof. Background technique [0002] Liquid crystal material is a mixture of organic rod-shaped small molecular compounds that have both fluidity of liquid and anisotropy of crystal at a certain temperature. Liquid crystal display devices work by utilizing the optical anisotropy and dielectric anisotropy of the liquid crystal material itself, and have been widely used at present. Using different characteristics and working modes of liquid crystal materials, devices can be designed in different working modes, mainly including the following: dynamic scattering (dynamic scattering, DS) type, electric field controlled birefringence (electrically controlled birefringence, ECB) type, twisted Nematic (twisted nematic, TN) type, ferroelectric liquid crystal (FLC) ty...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/44C09K19/34C07D307/91
CPCC07D307/91C09K19/3405C09K19/44C09K2019/3408
Inventor 金立诺吕维军李坤黎兴斌
Owner 西安晶奥量新材料有限公司
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