Liquid-crystalline compound having difluoromethyleneoxy group, liquid crystal composition, and liquid crystal display element

一种液晶组合物、化合物的技术，应用在有机化学、液晶材料、非线性光学等方向，能够解决介电常数不足够大等问题，达到透明点高、短响应时间、低阈电压的效果

Active Publication Date: 2015-12-02
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the dielectric constant of these compounds in the minor axis direction is not large enough

Method used

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  • Liquid-crystalline compound having difluoromethyleneoxy group, liquid crystal composition, and liquid crystal display element
  • Liquid-crystalline compound having difluoromethyleneoxy group, liquid crystal composition, and liquid crystal display element
  • Liquid-crystalline compound having difluoromethyleneoxy group, liquid crystal composition, and liquid crystal display element

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preparation example Construction

[0247] Composition (1) is prepared by a method such as dissolving required components at high temperature. Depending on the application, additives may be added to the composition. Examples of additives are optically active compounds, polymerizable compounds, polymerization initiators, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, defoamers, pigments, and the like. Such additives are well known to those skilled in the art and are described in the literature.

[0248] Composition (1) may further contain at least one optically active compound. The optically active compound has an effect of preventing reverse twist by imparting a desired torsion angle (torsion angle) by generating a helical structure in the liquid crystal molecule. Preferable examples of the optically active compound include the following compound (Op-1) to compound (Op-18).

[0249]

[0250] In compound (Op-18), ring F is 1,4-cyclohexylene or 1,4-phenylene, R 21 is an alkyl grou...

Embodiment 1

[0306] Synthesis of compound (No.1-2-2)

[0307]

[0308] Step 1

[0309] Under nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (48.5ml) and tetrahydrofuran (THF) (250ml) were added into the reactor, and cooled to 0°C. Thereto, n-butyllithium (1.60 M, n-hexane solution, 178 ml) was slowly added, followed by stirring for 1 hour. Then cool to -70°C, slowly add compound (T-1) (50.0g) in THF (500ml) solution, after stirring for 1 hour, slowly add DMF (N,N-dimethylformylfluorene) (40.1ml) , and stirred for 12 hours while returning to room temperature. The reaction mixture was poured into saturated aqueous ammonium chloride, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, hexane:ethyl acetate=5:1). Furthermore, it purified by recrystallization in...

Embodiment 2

[0323] Synthesis of compound (No.1-4-21)

[0324]

[0325] Step 1

[0326] Under nitrogen atmosphere, compound (T-8) (50.0 g) and diethyl ether (800 ml) were added into the reactor, and cooled to -70°C. Thereto, n-butyllithium (1.63 M, n-hexane solution, 112 ml) was slowly added, followed by stirring for 2 hours. Then, a diethyl ether (50.0 ml) solution of trimethyl borate (22.8 g) was slowly added, and the mixture was stirred for 12 hours while returning to room temperature. Then, it was cooled to -30°C, 6N hydrochloric acid (150 ml) was slowly added, and the mixture was stirred for 3 hours while returning to room temperature. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and purified by recrystallization from heptane to obtain compound (T-9) (29.2 g, 78%).

[0327] St...

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Abstract

Provided are: a liquid-crystalline compound which satisfies at least one property selected from high stability to light, a high clear point, a low lower-limit temperature of a liquid crystal phase, a low viscosity, proper optical anisotropy, high dielectric anisotropy, a high dielectric constant in a short axis direction, a proper elastic constant, excellent compatibility and the like; a liquid crystal composition which contains the compound; and a liquid crystal display element comprising the composition. A compound represented by formula (1). For example, R1 represents an alkyl group having 1 to 15 carbon atoms, rings A1 to A4 independently represent 1,4-cyclohexylene or 1,4-phenylene, Z1 to Z4 independently represent a single bond, -(CH2)2-, -COO- or -CH2O-, X1 represents a halogen atom, -C≡N, -CF3 or -OCF3, L1 and L2 independently represent a hydrogen atom or a fluorine atom, Y1 and Y2 independently represent a fluorine atom, and a, b, c and d independently represent 0 or 1 wherein the sum total of a, b, c and d is 1 or 2.

Description

technical field [0001] The present invention relates to a liquid crystal compound, a liquid crystal composition and a liquid crystal display element. More specifically, it relates to a compound having a difluoromethyleneoxy group, a liquid crystal composition containing the compound and having a nematic phase, and a liquid crystal display device containing the composition. Background technique [0002] Liquid crystal display elements are widely used in displays of personal computers, televisions, and the like. The element utilizes optical anisotropy, dielectric anisotropy, and the like of liquid crystal compounds. The operation modes of liquid crystal display elements are known as: phase change (phasechange, PC) mode, twisted nematic (twistednematic, TN) mode, supertwisted nematic (supertwistednematic, STN) mode, bistable twisted nematic (bistabletwistednematic, BTN) mode ) mode, electrically controlled birefringence (ECB) mode, optically compensated bend (OCB) mode, in-pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C43/29C07C69/773C07D213/34C07D239/26C07D309/06C07D319/06C07D493/08C09K19/12C09K19/18C09K19/30C09K19/32C09K19/34C09K19/42G02F1/13
CPCC09K19/20C07D213/34C07D239/26C07D309/06C07D319/06C07D493/08C09K19/3066C09K19/3098C09K19/32C09K2019/0466C09K2019/3027C09K2019/3422C07C2601/14C07D213/30C07C43/225C09K19/3068C09K19/3402C09K2019/3077C09K2019/308C09K2019/3083
Inventor 田中裕之远藤浩史
Owner JNC CORP
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