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Polymerizable compound and its polymer, liquid crystal composition and liquid crystal display element

A polymer compound, CH3 technology, applied in the direction of liquid crystal materials, organic chemistry, nonlinear optics, etc., can solve the problems of reduced polymerization reactivity and high solubility of liquid crystal compositions, and achieve large voltage retention, short response time, wide temperature range effect

Active Publication Date: 2017-03-22
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a polymeric compound used in this type of device, although it is considered that the ability to align liquid crystal molecules is high, it cannot be said that the solubility in liquid crystal compositions is high.
Attempts have been made so far to improve the solubility in liquid crystal compositions, but when the solubility increases, the polymerization reactivity tends to decrease

Method used

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  • Polymerizable compound and its polymer, liquid crystal composition and liquid crystal display element
  • Polymerizable compound and its polymer, liquid crystal composition and liquid crystal display element
  • Polymerizable compound and its polymer, liquid crystal composition and liquid crystal display element

Examples

Experimental program
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Effect test

preparation example Construction

[0247] The liquid crystal composition can be prepared by a method such as dissolving essential components at a temperature higher than room temperature. Additives can also be added to this composition according to usage. Examples of additives are optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, defoamers, and the like. Such additives are widely known to those skilled in the art and are documented in the literature.

[0248] The optically active compound has an effect of preventing reverse twist by imparting a twist angle necessary for inducing a helical structure to liquid crystal molecules. By adding optically active compounds, the helical pitch can be tuned. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the helical pitch. Preferable examples of the optically active compound include the following compound (Op-1) to compound (Op-18). In compound (Op-18), ri...

Embodiment 1

[0320]Tetrakis(2-methacrylic acid)[1,1'-biphenyl]-3,3',4,4'-tetrayl ester (compound 1-1-1) was synthesized according to the following scheme.

[0321]

[0322] Synthesis of the first step 3,4-dihydroxyphenylboronic acid (T-2)

[0323] 4-Bromocatechol (T-1) (18.8 g; manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in dry THF (200 ml) and cooled to -70°C. Under a nitrogen atmosphere, n-BuLi (72 ml) was added dropwise and stirred at -70° C. for 2 hours. Next, a THF solution of trimethyl borate (15.6 g) was slowly added dropwise at -70°C, and the temperature was raised to room temperature, followed by stirring for 16 hours. After the reaction was completed, 2N-HCl (100 ml) was added and extracted with toluene. The extract was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a pale brown solid. 3,4-Dihydroxyphenylboronic acid (T-2; 9.7 g, Yield 63%). ...

Embodiment 2

[0332] Tetrakis(2-methacrylic acid)[1,1'-biphenyl]-2,2',4,4'-tetrayl ester (compound 1-2-1) was synthesized according to the following scheme.

[0333]

[0334] Carry out in the same manner as the method described in Example 1, from 5-bromoresorcinol (T-5) (18.8g; manufactured by Tokyo Chemical Industry Co., Ltd.) and methacrylic acid (T-4) (9.29g) Tetrakis(2-methacrylic acid)[1,1′-biphenyl]-2,2′,4,4′-tetrayl ester (compound 1-2-1) was obtained as colorless crystals (6.37 g, Yield 13%).

[0335] 1 H-NMR (δppm; CDCl 3 ): 7.73(d, 2H), 7.24(s, 2H), 6.96(d, 2H), 6.42(d, 4H), 6.16(d, 4H), 2.00(s, 12H).

[0336] The physical properties of the compound (1-2-1) are shown below.

[0337] Melting point: 85°C, polymerization initiation temperature: 133°C.

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Abstract

The invention provides a polymeric compound and its polymer, a liquid crystal composition and a liquid crystal display element. A polymerizable compound having suitable polymerization reactivity, high conversion rate and good solubility in liquid crystal composition is provided. Provides high upper limit temperature of nematic phase, low lower limit temperature of nematic phase, small viscosity, suitable optical anisotropy, large dielectric constant anisotropy, suitable elastic constant, large specific resistance , and a liquid crystal composition having physical properties such as suitable pretilt. To provide liquid crystal display elements with wide temperature range, short response time, high voltage retention, low threshold voltage, high contrast, suitable pretilt and long life. A compound represented by formula (1), a liquid crystal composition, and a liquid crystal display element.

Description

technical field [0001] The present invention relates to a polymerizable compound having four photopolymerizable groups and a liquid crystal composition containing the polymerizable compound. The present invention also relates to a liquid crystal display element in which a liquid crystal composition is sealed between substrates, and a polymerizable compound is polymerized while adjusting a voltage applied to the substrates to fix the orientation of liquid crystal molecules. Background technique [0002] A liquid crystal display element utilizes optical anisotropy, dielectric anisotropy, and the like possessed by liquid crystal molecules in a liquid crystal composition. The classification based on the operation mode of liquid crystal molecules is 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 Patents(China)
IPC IPC(8): C08F20/30C07C69/54C09K19/12C09K19/18C09K19/20C09K19/30C09K19/32C09K19/34C09K19/38G02F1/13
CPCC09K2019/0448C09K2019/122C07C2601/14C09K19/12C09K19/3809C09K19/3028C09K19/3402C09K19/16C09K19/2007C09K19/2014C09K19/18C09K19/20C09K19/3003C07C69/54C09K2019/123C07C69/80C09K19/542C09K19/3066C09K19/3001C09K19/3068C07C69/017C07C69/96C07C69/007C07C69/618C09K2019/3422C09K2019/3077C09K2019/3083C09K2019/3425C09K2019/548
Inventor 后藤泰行松隈真依子山下淳一
Owner JNC CORP
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