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Liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy 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，能够解决相容性不够高、介电常数各向异性大、稳定性不够高等问题，达到响应时间短、介电常数各向异性大、电压保持率大的效果

Active Publication Date: 2016-10-12
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] (6) Large dielectric constant anisotropy (Δε)
[0016] However, the compound is not sufficiently thermally stable nor compatible at low temperatures

Method used

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  • Liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy group, liquid crystal composition, and liquid crystal display element
  • Liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy group, liquid crystal composition, and liquid crystal display element
  • Liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy group, liquid crystal composition, and liquid crystal display element

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Experimental program
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preparation example Construction

[0232] Composition (1) is prepared by a method such as dissolving essential components at high temperature. Additives can also be added to this composition according to the use. 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 widely known to those skilled in the art and are described in the literature.

[0233] Composition (1) may also further contain at least one optically active compound. The optically active compound has an effect of preventing reverse twist by inducing a helical structure in liquid crystal molecules to impart a necessary twist angle. Preferable examples of the optically active compound include the following compound (Op-1) to compound (Op-18).

[0234]

[0235] In compound (Op-18), ring F is 1,4-cyclohexylene or 1,4-phenylene, R 21 is an alkyl group having 1 to 10 ca...

Embodiment 1

[0290] [Example 1] 4-((3,5-difluoro-4-((1,1,3,3-tetrafluoroallyl)oxy)phenoxy)difluoromethyl)-3,5 -Synthesis of difluoro-4'-propyl-1,1'-biphenyl (No.1-2-73)

[0291]

[0292] 4-((3,5-difluoro-4'-propyl-[1,1'-biphenyl]-4-yl)difluoromethoxy base)-2,6-difluorophenol (2.00g, 4.69mmol) and potassium carbonate (2.16g, 15.62mmol), and 1,3-dibromo-1,1,3,3-tetrafluoropropane (2.15g , 7.83mmol) was stirred in acetonitrile at 65°C for 3 hours. The reaction liquid was poured into water, and extracted with toluene. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and the solvent was distilled off with an evaporator. The residue was purified by silica gel chromatography and recrystallization, thereby obtaining compound (No. 1-2-73) (yield 62%).

[0293] 1 H-NMR (CDCl 3 )δ7.50-7.48(m, 2H), 7.30-7.29(m, 2H), 7.22-7.20(m, 2H), 7.00-6.97(m, 2H), 5.00-4.93(m, 1H), 2.66- 2.63(m, 2H), 1.68(sex, J=7.6Hz, 2H), 0.97(t, J=7.3Hz, 3H).

[0294] The phy...

Embodiment 2

[0295] [Example 2] 4-(3,5-difluoro-4-((1,1,3,3-tetrafluoroallyl)oxy)phenyl)-4'-propyl-1,1' -Synthesis of bis(cyclohexane) (No.1-2-40)

[0296]

[0297] Using 2,6-difluoro-4-(4'-propyl-[1,1'-bis(cyclohexane)]-4-yl)phenol synthesized by the method described in JP-A-2007-277127 (3.00 g, 8.92 mmol), the compound (No.1-2-40) was obtained by the same method as in Example 1 (yield 75%).

[0298] 1 H-NMR (CDCl 3 )δ6.83-6.79 (m, 2H), 4.99-4.91 (m, 1H), 2.44-2.38 (m, 1H), 1.91-1.84 (m, 4H), 1.78-1.71 (m, 4H), 1.38- 1.23(m, 5H), 1.16-0.95(m, 8H), 0.89-0.82(m, 5H).

[0299] The physical properties of the compound (No.1-2-40) are as follows. Phase transition temperature: C 46.0N 172I. Upper limit temperature (NI) = 116°C; dielectric constant anisotropy (Δε) = 6.1; optical anisotropy (Δn) = 0.104; viscosity (η) = 33.5mPa·s.

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Abstract

Provided are: a liquid crystal compound satisfying at least one physical property such as high stability with respect to heat, light, and the like, high clearing point, low lower-limit temperature in the liquid crystal phase, low viscosity, suitable optical anisotropy, large dielectric constant anisotropy, suitable elastic constants, and exceptional compatibility with other liquid crystal compounds; a liquid crystal composition containing this compound; and a liquid crystal display element including this composition. A compound represented by formula (1). In formula (1), for example, R1 is a C1-C15 alkyl; ring A1 and ring A2 are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene having at least one hydrogen substituted by a halogen, tetrahydropyran-2,5-diyl, or 1,3-dioxan-2,5-diyl; Z1 and Z2 are a single bond or -CF2O-; L1, L2, and L3 are halogen or hydrogen; and a is 0-3.

Description

technical field [0001] The invention relates to a liquid crystal compound, a liquid crystal composition and a liquid crystal display element. More specifically, the present invention relates to a liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy, a liquid crystal composition containing the compound and having a nematic phase, and a liquid crystal composition containing the compound Object liquid crystal display element. Background technique [0002] Liquid crystal display elements are widely used in displays of personal computers, televisions, and the like. This device utilizes optical anisotropy, dielectric anisotropy, and the like of liquid crystal compounds. Regarding the operation mode of the liquid crystal display element, known phase change (phase change, PC) mode, twisted nematic (twisted nematic, TN) mode, super twisted nematic (super twisted nematic, STN) mode, bistable twisted nematic (bistable twisted nematic, BTN) mode, electrically controlled birefri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C09K19/12C09K19/14C09K19/18C09K19/20C09K19/30C09K19/32C09K19/34C09K19/42C09K19/54G02F1/13
CPCC07C43/225C07D213/30C07D239/26C07D309/06C07D319/06C07D405/04C07D493/08C09K19/20C09K19/3028C09K19/3066C09K19/32C09K19/3458C09K2019/0444C09K2019/0466C09K2019/123C09K2019/124C09K2019/301C09K2019/3016C09K2019/3019C09K2019/3025C09K2019/3077C09K2019/308C09K2019/3083C09K2019/3422C09K2019/3425C07C2601/14C09K19/3001C09K19/3068C09K19/3402
Inventor 高田章博久保贵裕
Owner JNC CORP
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