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Compound having polymerizable group, liquid crystal composition and liquid crystal display element

A technology of polymerizable groups and compounds, which can be applied to compounds of Group 4/14 elements of the periodic table, organic chemistry, liquid crystal materials, etc. The effect of high retention rate and wide temperature range

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, although the compound has a high ability of homeotropically aligning liquid crystal molecules, its voltage holding ratio is not sufficiently high when used in a liquid crystal display element.

Method used

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  • Compound having polymerizable group, liquid crystal composition and liquid crystal display element
  • Compound having polymerizable group, liquid crystal composition and liquid crystal display element
  • Compound having polymerizable group, liquid crystal composition and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0320] The present invention will be further described in detail through examples (including synthesis examples and use examples). The present invention is not limited by these Examples. The present invention comprises a mixture of the composition of use example 1 and the composition of use example 2. The present invention also includes mixtures prepared by mixing at least two of the compositions of the use examples.

[0321] 1. Examples of compound (1)

[0322] Compound (1) was synthesized in the procedure shown in the Examples. Unless otherwise specified, the reaction was performed under a nitrogen atmosphere. Compound (1) was synthesized in the procedure 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.

[0323] NMR analysis: DRX-500 m...

Synthetic example 1

[0370] Synthesis of compound (1-1-10)

[0371]

[0372] Step 1

[0373] Compound (T-1) (4.98g), compound (T-2) (5.00g), potassium carbonate (6.88g), tetrakis (triphenylphosphine) palladium (0.289g) and isopropanol (IsoPropyleAlcohol , IPA) (100ml) was added to the reactor, and heated to reflux at 80° C. for 2 hours. The reaction mixture was poured into water, neutralized with 1N hydrochloric acid, and then extracted with ethyl acetate. 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 (volume ratio, toluene) to obtain Compound (T-3) (6.38 g; 99%).

[0374] Step 2

[0375] Sodium borohydride (1.88g) and methanol (90ml) were added to the reactor and cooled to 0°C. A solution of compound (T-3) (6.38 g) in tetrahydrofuran (THF) (40 ml) was slowly added dropwise thereto, followed by stirring for 8 hours while returning t...

Synthetic example 2

[0381] Synthesis of compound (1-9-16)

[0382]

[0383] Step 1

[0384] Ethylene glycol (25g), 3,4-dihydro-2H-pyran (33.88g), pyridinium p-toluenesulfonate (2.53g) and dichloromethane (200ml) were added to the reactor, at room temperature Stir for 5 hours. The reaction mixture was poured into water, and extracted with dichloromethane. 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 (volume ratio, heptane:ethyl acetate=2:1) ​​to obtain compound (T-5) (27.67 g; 47%).

[0385] Step 2

[0386] 2-Hydroxyphenyl acetate (25 g), tetrabutylammonium bromide (79.2 g) and methanol (250 ml) were added to the reactor and stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=2:1) ​​to o...

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PUM

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Abstract

Provided is a polar compound which has high chemical stability and high ability of aligning liquid crystal molecules, and which enables the achievement of high voltage holding ratio if used for a liquid crystal display element. A compound represented by formula (1). (In the formula, R1 represents, for example, an alkyl group having 1-15 carbon atoms; each of rings A1-A5 represents 1,4-cyclohexylene or 1,4-phenylene; each of Z1 and Z5 represents a single bond or an alkylene group having 1-10 carbon atoms; each of a and b represents a number of 0-4, and the sum of a and b is 4 or less; d represents a number of 1-4; each of c and e represents a number of 0-4; each of P1-P3 represents a polymerizable group represented by one of formulae (P-1)-(P-5), wherein each of M1-M3 represents a hydrogen atom or an alkyl group having 1-5 carbon atoms; and R2 represents a group represented by one of formulae (1a)-(1c), wherein each of Sp1-Sp5 represents a single bond or an alkylene group having 1-10 carbon atoms, S1 represents >CH-, S2 represents >C<, and X1 represents -OH.)

Description

technical field [0001] The present invention relates to a compound having a polymeric group, a liquid crystal composition and a liquid crystal display element. More specifically, it relates to a compound having both a polymerizable group such as a methacryloyloxy group and a polar group such as an -OH group, a liquid crystal composition containing the compound and having positive or negative dielectric anisotropy, and A liquid crystal display element comprising 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), electrically controlled birefringence (electrically controlled birefringence, ECB), optically compensated bend (optically compensated bend, OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe field switch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C69/653C08F16/12C08F20/30C08G59/00C09K19/12C09K19/38C09K19/42C09K19/54G02F1/13G02F1/1337C08F2/50
CPCC07C69/54C07C69/653C08F16/12C08F20/30C08F2/50C08G59/00C09K19/12C09K19/38C09K19/42C09K19/54G02F1/13G02F1/1337C07F7/1804C07D213/30C07D239/26C07D303/14C07D305/06C07D309/06C07D319/06C07C69/732C07C69/736C08F16/20C07C2601/14C07C43/1787C07C69/94C07C219/18C08F16/24C08F16/26C09K19/3001C09K19/3003C09K19/3068C09K19/3402C09K19/3458C09K19/542C09K2019/3009C09K2019/301C09K2019/3016C09K2019/3077C09K2019/308C09K2019/3083C09K2019/3422
Inventor 田中裕之矢野匡一近藤史尚荻田和寛
Owner JNC CORP
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