Cinnamic Acid Derivatives

A mixture and compound technology, applied in the field of cinnamic acid derivatives, can solve problems such as inhomogeneity, pollution, electrostatic discharge, etc.

Active Publication Date: 2022-03-11
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the rubbing method creates many problems: non-uniformity (mura), contamination, electrostatic discharge pr

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0534] Hereinafter, the present invention will be explained in more detail and specifically with reference to Examples, however, the Examples are not intended to limit the present invention.

[0535] Synthesis Example 1: (E)-3-[3-(2-hydroxyethoxy)-4-(4-pentylbiphenyl)]prop-2-enoic acid ethyl ester

[0536] The starting material 2-fluoro-4-iodo-1-(4-pentyl-phenyl)-benzene was prepared according to literature procedures by combining 5-pentylphenylboronic acid with 4-bromo-2-fluoro-1 -Iodine-benzene Suzuki coupling followed by bromine-lithium exchange and reaction of the lithiated intermediate with iodine.

[0537] Stage 1: 2-[5-iodo-2-(4-pentylphenyl)phenoxy]ethanol

[0538]

[0539] Triethylene glycol dimethyl ether (100 ml), dibenzo-18-crown-6 (1.3 g, 3.6 mmol) and sodium hydride (8 g, 60% dispersion in oil, 200 mmol) were stirred at room temperature. Anhydrous ethylene glycol (40ml, 720mmol) was added dropwise over 30 minutes, keeping the temperature below 60°C. 2-Fluor...

Embodiment 2

[0543] Example 2: (E)-3-[4-(4-pentylphenyl)-3-(3-trimethoxysilylpropoxy)-phenyl]prop-2-enoic acid ethyl ester

[0544] Step 1: (E)-3-[3-allyloxy-4-(4-pentylphenyl)phenyl]prop-2-enoic acid ethyl ester

[0545]

[0546] 2-Fluoro-4-iodo-1-(4-pentyl-phenyl)-benzene was reacted with sodium hydroxide in triethylene glycol under the same reaction conditions as described in Example 1 to give 5- Iodo-2-(4-pentylphenyl)phenol.

[0547] 5-iodo-2-(4-pentylphenyl)phenol (0.5g, 1.48mmol), allyl bromide (0.14ml, 1.62mmol), potassium carbonate (0.3g, 2.2mmol) and Butanone (3ml) was heated for 3 hours. The mixture was cooled and the solvent was removed in vacuo. The residue was dissolved in dichloromethane and purified by vacuum flash chromatography on silica (40 g) eluting with dichloromethane. Fractions containing product were combined and the solvent was removed in vacuo to give ethyl (E)-3-[3-allyloxy-4-(4-pentylphenyl)phenyl]prop-2-enoate .

[0548] Step 2: (E)-3-[4-(4-Pentylphen...

Embodiment 3

[0553]

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Abstract

The present invention relates to cinnamic acid derivatives of formula (S) wherein the radicals have the meanings indicated in claim 1, to a process for their preparation and to their use as self-assembling photoalignment agents in liquid crystal mixtures. The present invention further relates to a method for producing a liquid crystal (LC) display device with in-plane alignment by photoaligning a liquid crystal mixture having positive or negative dielectric anisotropy, the liquid crystal mixture comprising one or more compounds of formula S and optionally Polymerizing compounds, relating to the liquid crystal mixture comprising the self-assembled photo-alignment agent and optionally the polymerizable compound and the LC display manufactured by said method.

Description

technical field [0001] The present invention relates to cinnamic acid derivatives, their preparation process and their use as self-assembled photoalignment agents in liquid crystal mixtures. The present invention further relates to liquid crystal mixtures comprising said cinnamic acid derivatives and optionally polymerizable compounds, to a method for producing liquid crystal (LC) display devices with in-plane alignment by photoaligning the cinnamic acid derivatives after their self-assembly And an LC display manufactured by said method. Background technique [0002] Liquid crystal media have been used for decades in electro-optic displays (liquid crystal displays - LCDs) for the purpose of displaying information. Liquid crystal displays (LC displays) in use today are generally those of the TN ("twisted nematic") type. However, these have the disadvantage of a strong viewing angle dependence of the contrast. [0003] In addition, so-called VA (“Vertical Alignment”) displa...

Claims

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Application Information

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IPC IPC(8): C07C69/734C09K19/20C09K19/30C09K19/04
CPCC09K19/20C09K19/2014C09K19/3066C09K2019/0448C09K2019/0466C09K2019/3004C09K19/3068C09K19/42G02F1/133788G02F1/134363C07C69/734C07F7/1876C09K19/3402C09K2019/3416G02F1/1341
Inventor K·阿德莱姆A·霍尔特H·阿拉斯J·萨根特R·图芬I·C·萨格
Owner MERCK PATENT GMBH
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