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Polymerizable compound having methoxymethyl acrylic group, liquid crystal composition, and liquid crystal display device

A compound and polymerizable technology, applied in organic chemistry, liquid crystal materials, nonlinear optics, etc., can solve the problem of decreased polymerization reactivity, and achieve the effects of low polymerization initiation temperature, large contrast ratio, and appropriate elastic constant.

Active Publication Date: 2020-07-28
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, attempts have been made to improve the solubility in liquid crystal compositions, but the polymerization reactivity tends to decrease as the solubility increases

Method used

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  • Polymerizable compound having methoxymethyl acrylic group, liquid crystal composition, and liquid crystal display device
  • Polymerizable compound having methoxymethyl acrylic group, liquid crystal composition, and liquid crystal display device
  • Polymerizable compound having methoxymethyl acrylic group, liquid crystal composition, and liquid crystal display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0293] 1. Examples of compound (1)

[0294] The present invention is illustrated in more detail by way of examples. The Examples are typical examples, and therefore the present invention is not limited by the Examples. Compound (1) was synthesized by the following procedure. The synthesized compound was identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The physical properties of the compound or composition, and the characteristics of the device were measured by the following methods.

[0295] NMR analysis: DRX-500 manufactured by Bruker BioSpin was used for measurement. exist 1 In the measurement of H-NMR, the sample is dissolved in CDCl 3 and other deuterated solvents, and measured at room temperature, 500 MHz, and accumulated times 16 times. Tetramethylsilane was used as an internal standard. exist 19 In the determination of F-NMR, the CFCl 3 It was used as an internal standard, and it carried out by accumulating ...

Synthetic example 1

[0330] Synthesis of compound (No.1-1-14)

[0331]

[0332] first step

[0333] Under a nitrogen atmosphere, compound (T-1) (3 g, 14.69 mmol) and dichloromethane (300 ml) synthesized by a conventional method were put into a reactor, and cooled to 0°C. Compound (T-2) (5.63g, 48.48mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (9.29g , 48.48mmol), and triethylamine (9.01ml, 64.64mmol), and warmed to room temperature. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The mixed organic layers were washed with water, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / ethyl acetate=19 / 1, volume ratio) and recrystallization to obtain compound (1-1-14 ) (4.13 g, 70% yield).

[0334] 1 H-NMR (ppm; CDCl 3 ): δ7.81-7.76 (m, 3H), 7.60 (d, J = 8.3Hz, 1H), 7.45 (t, J = 8.4Hz, 1H), 7.30 (d, J = 8.4Hz,...

Synthetic example 2

[0337] Synthesis of compound (No.1-1-35)

[0338]

[0339] first step

[0340] Under nitrogen atmosphere, put compound (T-1) (8g, 39.18mmol), ethylene carbonate (7.59g, 86.19mmol), potassium carbonate (16.24g, 117.53mmol) and dimethylformamide (100ml) into the reactor and heated to reflux. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The mixed organic layers were washed with water, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (toluene / ethyl acetate=4 / 1, volume ratio) to obtain compound (T-3) (3.8 g, yield 33%).

[0341] second step

[0342] Under a nitrogen atmosphere, compound (T-3) (3.8 g, 13.0 mmol) and dichloromethane (300 ml) synthesized by a conventional method were put into a reactor, and cooled to 0°C. Compound (T-2) (3.32g, 28.6mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (5.48g ,...

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Abstract

The present invention addresses the problem of providing: a polymerizable compound having suitable polymerization reactivity, a high conversion rate, a low polymerization initiation temperature, and ahigh solubility in a liquid crystal composition; a liquid crystal composition containing said compound; and a liquid crystal display device containing said composition. To resolve the problem, a compound represented by formula (1), and a liquid crystal composition containing said compound are provided. In formula (1), R<1>, R<2>, and R<3> are each independently an alkyl, etc.; n is 0, etc.; ringA<1> is phenyl, etc.; ring A<2> and ring A<3> are each independently 1,4-phenylene, etc.; Z<1> and Z<2> are each independently a single bond, etc.; Sp<1>-Sp<4> are single bonds, etc.; a is 1, etc.; c,d, and e are each independently 0 or 1; the sum of c, d, and e is 1, etc.; P<1>-P<4> are polymerizable groups; and at least one among P<1>-P<4> is a polymerizable group represented by formula (P-1).

Description

technical field [0001] The present invention relates to a polymerizable compound, a polymerizable composition comprising the polymerizable compound and a liquid crystal composition, a liquid crystal composite prepared from the polymerizable composition, and a liquid crystal display element. More specifically, the present invention relates to a polymerizable compound having a methoxymethacrylic group, a liquid crystal composition containing the same, and a liquid crystal display device containing the composition. Background technique [0002] In liquid crystal display elements, the classification based on the operation mode of liquid crystal molecules is phase change (phase change, PC), twisted nematic (twisted nematic, TN), super twisted nematic (super twisted nematic, STN), electronically controlled birefringence ( Electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe fiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734C09K19/12C09K19/14C09K19/20C09K19/30C09K19/34C09K19/54G02F1/1337
CPCC07C69/734C09K2019/122C09K2019/181C09K2019/301C09K2019/3077C09K2019/3009C09K2019/3004C09K2019/3025C09K2019/3016C09K2019/3021C09K2019/3019C09K2019/3042C09K19/3028C09K2019/308C09K2019/0448C09K2019/123C09K19/0208C09K19/0403C09K19/12C09K19/14C09K19/20C09K19/3003C09K19/3048C09K19/322C09K19/34C09K2019/0485C09K2019/124C09K2019/3006C09K2019/3007C09K2019/3012C09K2019/3013C09K2019/3015
Inventor 森绚子田中裕之
Owner JNC CORP
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