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Liquid crystalline media with homeotropic alignment

A medium and polymerized liquid crystal technology, applied in the direction of liquid crystal materials, organic compound preparation, organic chemistry, etc., can solve the problem that VA display is not fully satisfactory

Active Publication Date: 2015-10-28
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0028] However, existing methods to obtain VA display applications without polyimide layers are still not fully satisfactory

Method used

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  • Liquid crystalline media with homeotropic alignment
  • Liquid crystalline media with homeotropic alignment
  • Liquid crystalline media with homeotropic alignment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0379] 2-Methacrylic acid 2-[2′-ethyl-4-(2-hydroxyethoxy)-4″-pentyl-[1,1′; 4′,1″]terphenyl-3-yl] Synthesis of ethyl ester 1

[0380]

[0381] 1) Synthesis of 4'-bromo-2'-ethylbiphenyl 4-alcohol A

[0382]

[0383] Add 223ml of water to 110.3g (1.04mol) Na 2 CO 3 , and 154 g (0.49 mol) 4-bromo-2-ethyl-1-iodobenzene, 75.1 g (0.54 mol) 4-hydroxyphenylboronic acid and 850 ml 1,4-dioxane were added and the mixture was degassed . 14.5 g (19.8 mmol) of bis(1,1-diphenylphosphinoferrocene)palladium(II) chloride were added, and the mixture was stirred at 80° C. for 18 hours. When the reaction was complete (checked by thin layer chromatography using heptane / ethyl acetate 1:1), the reaction mixture was cooled to room temperature, diluted with water and methyl tert-butyl ether and acidified to pH 1-2 using 2N HCl. The phases were separated, and the aqueous phase was extracted with methyl tert-butyl ether, and the combined organic phases were washed with Na 2 SO 4 Dry, filter a...

Embodiment 2

[0420] 2-Methacrylic acid 2′-ethyl-4″-(2-hydroxyethyl)-6″-(2-methyl-acryloyloxy)-4-pentyl-[1,1′;4′ , Synthesis of 1″]terphenyl-3″-yl ester 2

[0421]

[0422] 1) Synthesis of 4-bromo-2-ethyl-4'-pentyl biphenyl A2

[0423]

[0424] Dissolve 45.0g (234mmol) of 4-pentylphenylboronic acid, 70.0g (225mmol) of 4-bromo-2-ethyl-1-iodobenzene in 300ml of toluene, 200ml of ethanol and 200ml of Na 2 CO 3 The mixture of solutions (2 moles) was filled with nitrogen. Subsequently 8.00 g (6.92 mmol) of tetrakis(triphenylphosphine)palladium(0) were added, and the reaction mixture was refluxed for 18 hours. When the reaction was complete, the mixture was cooled to room temperature, and water was added, the phases were separated, and the organic phase was washed with water and washed with Na 2 SO 4 Dry, filter and evaporate in vacuo. The crude product (orange oil) was filtered through silica gel using heptane to give 56.2 g of product as a colorless oil.

[0425] 1 H NMR (500MHz, ...

Embodiment 3

[0459] 2-{5-[2-Ethyl-4-(4-pentylphenyl)phenyl]-2-[4-hydroxy-3-(hydroxymethyl)butoxy]phenyl}ethyl 2- Synthesis of methylprop-2-enoate 4

[0460]

[0461] 1) Synthesis of 4'-bromo-2'-ethylbiphenyl-4-alcohol A

[0462]

[0463] 223ml of water was added to 110.3g (1.04mol) of Na 2 CO 3 , and 154 g (0.49 mol) of 4-bromo-2-ethyl-1-iodobenzene, 75.1 g (0.54 mol) of 4-hydroxyphenolboronic acid and 850 ml of 1,4-dioxane were added, and the mixture was degassed. 14.5 g (19.8 mmol) of bis(1,1-diphenylphosphinoferrocene)palladium(II) chloride were added, and the mixture was stirred at 80° C. for 18 hours. When the reaction was complete (checked by thin layer chromatography using heptane / ethyl acetate 1:1), the reaction mixture was cooled to room temperature, diluted with water and methyl tert-butyl ether and acidified to pH 1-2 using 2N HCl. The phases were separated, and the aqueous phase was extracted with methyl tert-butyl ether, and the combined organic phases were washed ov...

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Abstract

The present invention relates to liquid-crystalline media (LC media) having negative or positive dielectric anisotropy, comprising a low-molecular-weight component and a polymerizable component. The polymerizable component comprises self-aligning, polymerizable mesogens (polymerizable self-alignment additives) which effect homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The invention therefore also encompasses LC displays having homeotropic alignment of the LC medium without alignment layers. The invention discloses novel structures for self-alignment additives which have a certain position of the functional groups.

Description

technical field [0001] The invention relates to liquid-crystalline media (LC media) having negative or positive dielectric anisotropy, comprising low molecular weight components and polymerizable components. The polymerizable component comprises self-aligning, polymerizable mesogens (polymerizable self-aligning additives), which affect the homeotropic (vertical) alignment of the LC medium at the surface or cell wall of a liquid crystal display (LC display). The invention therefore also encompasses LC displays with homeotropic alignment of the liquid crystal medium (LC medium) without an alignment layer. The present invention discloses new structures for polymerizable self-aligning additives with position-specific functional groups. Background technique [0002] The principle of electrically controlled birefringence, the ECB effect or the DAP (Alignment Phase Deformation) effect was first described in 1971 (M.F.Schieckel and K.Fahrenschon, "Deformation of nematic liquid crys...

Claims

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Application Information

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IPC IPC(8): C09K19/46C09K19/12C09K19/14C09K19/30C09K19/52C07C69/653C07C67/297C07C67/29
CPCC09K19/3402C09K19/04C09K19/14C09K19/3003C09K19/3068C09K19/3852C09K19/56C09K2019/0448C09K2019/122C09K2019/123C09K2019/3004C09K2019/3009C09K2019/301C09K2019/3016C09K2019/3027C09K2019/304C09K2019/3078C09K2019/3422G02F1/1337G02F1/133788G02F1/1341G02F1/134363G02F2001/133742C09K2019/0425C09K19/38C09K19/42C09K19/08G02F1/133742
Inventor 格拉兹阿诺·阿切蒂齐藤泉罗克·福特托斯滕·科戴克
Owner MERCK PATENT GMBH
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