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Polymerizable polar compound, liquid crystal composition, and liquid crystal display element

A compound and carbon number technology, used in the field of polymeric polar compounds, can solve the problem of insufficient voltage retention, and achieve the effects of appropriate optical anisotropy, high stability and low threshold voltage

Active Publication Date: 2017-08-29
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, regarding the compound, although the ability to vertically align liquid crystal molecules is high, the voltage holding ratio in the case of being used in a liquid crystal display element is not large enough

Method used

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  • Polymerizable polar compound, liquid crystal composition, and liquid crystal display element
  • Polymerizable polar compound, liquid crystal composition, and liquid crystal display element
  • Polymerizable polar compound, liquid crystal composition, and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0390] The present invention will be described in more detail using examples (including synthesis examples and use examples). The present invention is not limited by these Examples. The present invention includes a mixture of the composition of Example 1 and the composition of Example 2. The present invention also includes mixtures prepared by mixing at least two of the compositions of the use examples.

[0391] 1. Examples of compound (1)

[0392] Compound (1) was synthesized according to the procedures shown in the examples. Unless otherwise specified, the reaction was performed under a nitrogen atmosphere. Compound (1) was synthesized according to the procedures shown in Example 1 and the like. The synthesized compounds are identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The properties of compound (1), liquid crystal compound, composition, and device were measured by the following methods.

[0393]NMR analysis: ...

Synthetic example 1

[0440] Synthesis of compound (1-4-2)

[0441] [chem 93]

[0442]

[0443] Step 1

[0444] Compound (T-1) (25.0 g), acrylic acid (7.14 g), DMAP (1.21 g) and dichloromethane (300 ml) were put into a reactor, and cooled to 0°C. A solution of DCC (24.5 g) in dichloromethane (125 ml) was slowly added dropwise thereto, returned to room temperature and stirred for 12 hours. After removing the insoluble matter, the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer formed at the same time was washed with water, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:toluene=2:1). Furthermore, it purified by recrystallization from solmix (registered trademark) A-11, and compound (T-2) (11.6g; 38%) was obtained.

[0445] Step 2

[0446] Put paraformaldehyde (2.75g), DABCO (4.62g) and water (40...

Synthetic example 2

[0452] Synthesis of compound (1-4-22)

[0453] [chem 94]

[0454]

[0455] Step 1

[0456] Compound (T-4) (42.5 g; 65%) was obtained by the same method as in the second step of Synthesis Example 1, using compound (T-3) (50.0 g) as a raw material.

[0457] Step 2

[0458]Compound (T-4) (42.5g), imidazole (24.5g) and dichloromethane (740ml) were put into the reactor and cooled to 0°C. A dichloromethane (110 ml) solution of t-butyldimethylsilyl chloride (54.1 g) was slowly added dropwise thereto, returned to room temperature, and stirred for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer formed at the same time was washed with water, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=10:1) to obtain compound (T-5) (79.8 g; 100%).

[0459] Step 3

[...

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Abstract

Provided is a polar compound having high chemical stability, high ability to align liquid crystal molecules, and high solubility in a liquid crystal composition, and which has a large voltage holding ratio when used in a liquid crystal display element. A compound represented by formula (1). For example, R2 represents a C1-15 alkyl, MES represents a mesogenic group having at least one ring, Sp1 represents a single bond or a C1-10 alkylene, M1 and M2 represent hydrogen, R2 represents a group represented by formulas (1a) through (1c), Sp2 and Sp3 are single bonds or C1-10 alkylenes, S1 represents >CH-, S2 represents >C<, and X1 represents -OH.

Description

technical field [0001] The invention relates to a polymerizable polar compound, a liquid crystal composition and a liquid crystal display element. More specifically, the present invention relates to a polymerizable polar compound having an acryloyloxy group substituted by a polar group such as hydroxyalkyl, and a liquid crystal composition containing the compound and having positive or negative dielectric anisotropy. Objects, and liquid crystal display elements containing the composition. Background technique [0002] Liquid crystal display elements are classified into phase change (phase change, PC), twisted nematic (twisted nematic, TN), super twisted nematic (super twisted nematic, STN) and electrically controlled birefringence (electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe field switching (fringe field switching, FFS), electric field sensing light Reactive ori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/732C07C229/08C07C229/30C07C321/10C07D213/55C07D239/26C07D295/145C07D309/06C07D319/06C07F5/02C07F7/18C09K19/12C09K19/34C09K19/42C09K19/54G02F1/1337
CPCC07D309/06C07D319/06C07D239/26C07C321/10C07C229/08C07C229/30C07F5/02C07D295/145C07F7/18C07D213/55C09K19/12C09K19/34C09K19/42C09K19/54G02F1/1337C09K19/04C09K19/062C09K19/18C09K19/32C09K19/322C09K19/3402C09K19/3483C09K2019/0444C09K2019/0448C09K2019/122C09K2019/123C09K2019/181C09K2019/3006C09K2019/3015C09K2019/3019C09K2019/3025C09K2019/3077C09K2019/3422C07C69/732C09K19/063C09K19/126C09K19/3003C09K19/36C09K2019/3004C09K2019/3009C09K2019/301C09K2019/3016C09K2019/303C07C2601/14C07C69/003C07C69/013C07C69/017C07C229/12C07J9/00G02F1/133788G02F1/1362
Inventor 田中裕之矢野匡一近藤史尚荻田和寛
Owner JNC CORP
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