Optically anisotropic layer and method for producing the same, laminate, polarizing plate, display device, liquid crystal compound and method for producing the same, carboxylic acid compound

An optical anisotropy, liquid crystal compound technology, applied in chemical instruments and methods, optics, polarizing elements, etc., can solve problems such as the influence of display characteristics

Active Publication Date: 2020-10-09
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there is concern that the difference in the wavelength of transmitted light will affect the display characteristics

Method used

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  • Optically anisotropic layer and method for producing the same, laminate, polarizing plate, display device, liquid crystal compound and method for producing the same, carboxylic acid compound
  • Optically anisotropic layer and method for producing the same, laminate, polarizing plate, display device, liquid crystal compound and method for producing the same, carboxylic acid compound
  • Optically anisotropic layer and method for producing the same, laminate, polarizing plate, display device, liquid crystal compound and method for producing the same, carboxylic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0282] Compound (I-1) was synthesized according to the following scheme.

[0283]

[0284]

[0285] Succinic acid mono(2-acryloyloxyethyl) ester (I-1A) 182g (839mmol), ethyl acetate 600mL, N,N-dimethylacetamide 150mL, 2,6-di-tert-butyl- 680 mg of 4-methylphenol was mixed, and the internal temperature was cooled to 5°C. 642 mL (879 mmol) of thionyl chloride was added dropwise to the mixture, taking care not to raise the internal temperature above 10°C. After stirring at 5° C. for 1 hour, a solution of 111 g (800 mmol) of 2-(4-hydroxyphenyl)ethanol in 220 mL of N,N-dimethylacetamide was added. Then, after stirring at room temperature for 12 hours, 400 mL of water was added for liquid separation. The collected organic layer was washed with 1N hydrochloric acid water, saturated sodium bicarbonate water and saturated brine, and dried over anhydrous sodium sulfate. Sodium sulfate was filtered off, and the solvent was removed by a rotary evaporator to obtain 255 g (758 mmol) ...

Embodiment 2

[0296] Compound (I-2) was synthesized according to the following scheme.

[0297]

[0298]

[0299] 40g (307mmol) of 2-hydroxyethyl methacrylate (I-2a), 300mL of dichloromethane, 3.8g (30.7mmol) of N,N-dimethylaminopyridine, 33.8g (338mmol) of succinic anhydride, 2, 200 mg of 6-di-tert-butyl-4-methylphenol was mixed, and the inner temperature was heated to 40°C. After stirring for 12 hours, it was cooled to room temperature, and 300 mL of water was added and stirred for 1 hour for liquid separation. The collected organic layer was washed with 1N hydrochloric acid water and saturated brine, and dried over anhydrous sodium sulfate. Sodium sulfate was filtered off, and the solvent was removed by a rotary evaporator to obtain 64 g (278 mmol) of compound (I-2A) as a clear oil (91% yield).

[0300]

[0301] Mix 30 g (130 mmol) of compound (I-2A), 50 mL of ethyl acetate, 15 mL of N,N-dimethylacetamide, and 100 mg of 2,6-di-tert-butyl-4-methylphenol, and cool the internal tem...

Embodiment 3

[0309] Compound (I-3) was synthesized according to the following scheme.

[0310]

[0311]

[0312] Compound (I-3A) was synthesized in the same manner as in Example 2, except that Compound (I-2a) in the synthesis method of Compound (I-2A) described in Example 2 was changed to Compound (I-3a). The rate is 92%).

[0313]

[0314] Compound (I-3B) was synthesized in the same manner as in Example 1, except that Compound (I-1A) in the synthesis method of Compound (I-1B) described in Example 1 was changed to Compound (I-3A). The rate is 94%).

[0315]

[0316] Compound (I-3C) was synthesized in the same manner as in Example 1, except that Compound (I-1B) in the synthesis method of Compound (I-1C) described in Example 1 was changed to Compound (I-3B). rate of 70%).

[0317] 1 H-NMR (solvent: CDCl 3 )δ (ppm): 1.45-1.72 (m, 4H), 1.72-1.80 (m, 4H), 2.10-2.30 (m, 4H), 2.33-2.45 (m, 1H), 2.47-2.65 (m, 1H) , 2.62(s, 4H), 2.93(t, 2H), 4.10-4.22(m, 4H), 4.30(t, 2H), 5.83(dd, 1H...

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PUM

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Abstract

The present invention provides a liquid crystal compound having reverse wavelength dispersion with improved solubility and phase transition temperature, and an optically anisotropic layer, a laminate, a polarizing plate, and a display device using the same. Provided are the liquid crystal compound, a method for producing an optically anisotropic layer, and a carboxylic acid compound as an intermediate of the liquid crystal compound. The optically anisotropic layer of the present invention contains a liquid crystal compound represented by the following general formula 1 or is formed by curing a polymerizable composition containing the liquid crystal compound, and is formed by aligning the long axes of the molecules of the liquid crystal compound. In the formula, L 1 , L 2 is a linking group with a carbonyl group, F 1 , F 2 is an alkyl group with 1 to 4 carbons, an alkoxy group with 1 to 4 carbons or a halogen atom, n and m are integers from 0 to 4, a and b are integers from 1 to 4, and T 1 , T 2 It is a spacer containing a straight-chain or branched alkylene group or an alkylene oxide group having 2 to 20 carbons, Ar has at least one aromatic ring selected from an aromatic hydrocarbon ring and an aromatic heterocyclic ring and in the group A divalent group containing 8 or more π electrons.

Description

technical field [0001] The present invention relates to an optically anisotropic layer having reverse wavelength dispersion and a method for producing the same, a laminate including the optically anisotropic layer, a polarizing plate, and a display device, a liquid crystal compound exhibiting reverse wavelength dispersion and a method for producing the same, as A carboxylic acid compound that is an intermediate of liquid crystal compounds. Background technique [0002] Optically anisotropic layers have been widely used in conventional liquid crystal display devices of various display modes for the purpose of improving wide viewing angles, high contrast ratios, and color shifts. In general, materials used in image display devices, especially polymers, exhibit retardation, that is, along-wavelength dispersion (also referred to as normal dispersion) in which the birefringence increases toward the short wavelength side. Therefore, there is a concern that the difference in wavel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/38C09K19/34G02B5/30C07C69/75
CPCB32B23/04B32B23/08B32B23/20B32B27/08B32B27/308B32B33/00B32B2250/24B32B2255/00B32B2255/10B32B2255/26B32B2305/55B32B2307/40B32B2307/4026B32B2307/42B32B2307/514B32B2307/706B32B2307/7246B32B2457/20C09K19/3068C09K19/348C09K19/3486C09K19/3491C09K19/3494C09K19/3497C09K19/3823C09K19/3861C09K2019/0448C09K2019/3408G02B5/305C09K19/3001C09K19/3477C09K19/38C09K2323/03C09K2323/035G02B5/3016
Inventor 松山拓史后藤亮司石川博之高桥庆太胜又泰司
Owner FUJIFILM CORP
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