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Liquid-crystal compound containing 1,4-dioxo-six-membered ring as well as preparation method and application thereof

A compound and liquid crystal technology, applied in the field of containing 1, can solve the problems of greatly reducing the liquid crystal clearing point and restricting the space for increasing the response speed of the liquid crystal mixture.

Inactive Publication Date: 2013-10-02
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction of -CF2O- groups will greatly reduce the clearing point of liquid crystals.
When preparing liquid crystal mixtures, it is necessary to add high-viscosity high-definition point compounds to balance the decrease in clearing points caused by -CF2O- groups, thus restricting the space for improving the response speed of liquid crystal mixtures

Method used

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  • Liquid-crystal compound containing 1,4-dioxo-six-membered ring as well as preparation method and application thereof
  • Liquid-crystal compound containing 1,4-dioxo-six-membered ring as well as preparation method and application thereof
  • Liquid-crystal compound containing 1,4-dioxo-six-membered ring as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1, compound shown in preparation formula I

[0087]

[0088] step 1:

[0089]

[0090] Add 56.64g (0.24mol) of 1,4-bromobenzene (reactant) and 400ml of dry tetrahydrofuran (solvent) into a 1L three-necked flask. ) n-butyllithium (reactant), dropwise and keep warm for 1 hour, under the same temperature, drop 42.6g (0.216mol, 72%) 1,4-dioxane-2-ketone (reactant) and 50ml dry The mixed solution of tetrahydrofuran (solvent) was stirred for 30 minutes after dropping, and the temperature was raised naturally, and 200ml of saturated ammonium chloride aqueous solution was added dropwise at about 0°C (adjusting the pH value), and the liquid was separated, and the aqueous phase was extracted with 200ml of ethyl acetate (solvent). The phase was washed with water, spin-dried to obtain 54g (GC: 89%) liquid, and another 1L three-necked flask was added with 54g of the product obtained above, 500ml of dry dichloromethane (solvent), and cooled to -25~-20°C under nitro...

Embodiment 2

[0109]

[0110] step 1:

[0111]

[0112] Add 60.96g (0.24mol) of 1,4-dibromo-2-fluorobenzene (reactant) and 400ml of dry tetrahydrofuran (solvent) into a 1L three-necked flask. 0.24mol, 2.5N) n-butyllithium (reactant), dropwise insulation 1 hour, under the same temperature, drop into 42.6g (0.216mol, 72%) 1,4-dioxane-2-ketone (reaction substance) and 50ml dry tetrahydrofuran (solvent) mixed solution, after dropping, stir for 30 minutes, naturally warm up, add 200ml saturated ammonium chloride aqueous solution (adjust pH value) dropwise at about 0°C, separate liquids, use 200ml ethyl acetate ( solvent) extraction, the organic phase was washed with water, spin-dried to obtain 54g (GC: 89%) liquid, in another 1L there-necked flask, add 54g of the product obtained above, 500ml dry dichloromethane (solvent), under nitrogen protection, cool to- 25~-20 ℃, dropwise add 63.3ml (0.397mol, 2.2eq) triethylsilane hydrogen (reactant), dropwise, add dropwise 50ml (0.397mol, 2.2eq) b...

Embodiment 3

[0134] Embodiment 3, preparation formula I described compound

[0135]

[0136] step 1

[0137]

[0138] Same as above embodiment 1, step 1.

[0139] step 2

[0140]

[0141] Add 0.1mol (3-a) (reactant) and 120ml tetrahydrofuran (solvent) obtained in the step into the reaction flask, install and seal the stirring, replace the air with nitrogen, cool to -70°C, and add dropwise 0.1mol concentration of 2.5M butane Lithium-based (reactant), 20 minutes after the addition, feed dry carbon dioxide gas (reactant), to saturation, react at this temperature for 2 hours, pour this reaction solution into 20ml concentrated hydrochloric acid (adjust pH value) Hydrolyze in a beaker with 100ml of water, separate the liquids, extract the water phase once with 50ml of ethyl acetate (solvent), combine the organic phases, wash with saturated brine until neutral, dry over anhydrous sodium sulfate (desiccant), concentrate to remove the solvent, and obtain Pale yellow solid, recrystalliz...

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PUM

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Abstract

The invention discloses a liquid-crystal compound containing a 1,4-dioxo-six-membered ring as well as a preparation method and an application thereof. The structure general formula of the compound is shown in a formula I. The compound has good thermal stability, so that when a right amount of liquid-crystal compound is used in optical elements, the relatively low threshold voltage can be realized; the liquid-crystal compound has fairly low rotary viscosity and very fast response speed, so that the liquid-crystal compound has very important practical significance for the preparation of a liquid-crystal mixture with the relatively low rotary viscosity. Therefore, the liquid-crystal compound is very suitable for application in the liquid-crystal mixture preparation. The liquid-crystal mixture containing the liquid-crystal compound can be applied to multiple displayers, is particularly suitable for TN-TFT and STN displayers and can be also used in IPS displayers.

Description

technical field [0001] The invention belongs to the field of liquid crystal compounds and applications, and relates to a liquid crystal compound containing a 1,4-dioxane six-membered ring, a preparation method and an application thereof. 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-containing heterocycles, a...

Claims

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Application Information

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IPC IPC(8): C07D319/12C09K19/34C09K19/44G02F1/1333
Inventor 夏治国华瑞茂韩耀华张芳苗
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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