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Liquid crystalline compound containing tetrafluorofluorene, liquid crystal composition, and liquid crystal display device

A liquid crystal composition and compound technology, applied in organic chemistry, liquid crystal materials, nonlinear optics, etc., can solve problems such as insufficient compatibility, high melting point, and large dielectric constant anisotropy, and achieve short response time, The effect of long life and high transparency point

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) The negative dielectric constant anisotropy (Δε) is large,
However, these compounds have high melting points and are not sufficiently compatible with other liquid crystalline compounds

Method used

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  • Liquid crystalline compound containing tetrafluorofluorene, liquid crystal composition, and liquid crystal display device
  • Liquid crystalline compound containing tetrafluorofluorene, liquid crystal composition, and liquid crystal display device
  • Liquid crystalline compound containing tetrafluorofluorene, liquid crystal composition, and liquid crystal display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0197] 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, and the like. Such additives are widely known to those skilled in the art and are described in the literature.

[0198] Composition (1) may also further contain at least one optically active compound. Well-known chiral dopants can be added as optically active compounds. This chiral dopant has the effect of inducing a helical structure in liquid crystal molecules to impart a necessary twist angle, thereby preventing reverse twisting. Preferable examples of the chiral dopant include compound (Op-1) to compound (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, R 24 is an alkyl group havi...

Embodiment 1

[0261] Synthesis of Compound (No.1-2-5)

[0262]

[0263] 1st process

[0264] Under nitrogen atmosphere, magnesium (20.8 g) and tetrahydrofuran (Tetrahydrofuran, THF) (30.0 ml) were put into the reactor and heated to 45° C. A THF (150 ml) solution of compound (T-1) (150 g) was slowly added thereto at a temperature range of 45°C to 55°C and stirred for 2 hours. Next, it cooled to 0 degreeC, the THF (200 ml) solution of compound (T-2) (127g) was added slowly, and it stirred for 2 hours, 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 layer was washed with water, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=10:1) to obtain Compound (T-3) (188 g; 95%).

[0265] 2nd process

[0266] Under a nitro...

Embodiment 2

[0286] Synthesis of Compound (No.1-2-6)

[0287]

[0288] 1st process

[0289] Under a nitrogen atmosphere, compound (T-12) (196 g) and THF (5000 ml) synthesized by the same method as in the seventh step of Example 1 were put into a reactor and cooled to -70°C. Thereto, sec-butyllithium (1.01M; cyclohexane, n-hexane solution; 1000 ml) was slowly added and stirred for 3 hours. Next, iron (III) chloride (92.1 g) was added, and it stirred for 12 hours, returning to room temperature. The reaction mixture was poured into 1N hydrochloric acid, and the aqueous layer was extracted with toluene. The combined organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane). Furthermore, purification was performed by recrystallization from heptane to obtain compound (1-2-6) (25.2 g; 13%).

[0290] Chemical shift δ (ppm; CDCl 3 ):7.09(d,J=5.4Hz...

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Abstract

Provided is a liquid crystalline compound that exhibits at least one physical property such as high stability to heat, light, or the like, a high clearing point, a low liquid crystal phase lower limit temperature, a low viscosity, suitable optical anisotropy, a high negative dielectric anisotropy, suitable elastic constant and excellent compatibility with other liquid crystalline compounds. The liquid crystalline compound is represented by formula (1). In the formula, for example, R1 and R2 are each an alkyl group having 1-15 carbon atoms, ring A1, ring A2 and ring A3 are each a 1,4-cyclohexylene ring or a 1,4-cyclohexenylene ring, Z1, Z2 and Z3 are each a single bond or -(CH2)2-, a, b and c are each 0 or 1, and the sum of a, b and c is 0, 1 or 2.

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 compound with a 3,4,5,6-tetrafluoro-9H-fluorene-2,7-diyl skeleton and a negative dielectric anisotropy, containing the compound , and a liquid crystal composition having a nematic phase and a liquid crystal display element containing the composition. 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 cont...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07D309/04C09K19/30C09K19/32C09K19/34C09K19/38C09K19/54G02F1/13
CPCC09K19/322C09K2019/0466C09K2019/122C09K2019/3004C09K2019/301C09K2019/3019C09K2019/3422C09K2019/3425C09K2019/3009C09K2019/3016C09K2019/3042C09K2019/3077C07C2601/14C07C2601/16C07C2603/18C09K19/32C07D309/04C09K19/3402C09K19/3458G02F1/13C07C25/22C07C25/24
Inventor 田中裕之平田健治矢野匡一
Owner JNC CORP
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