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Polymerisable compounds and the use thereof in liquid-crystal displays

A compound, polymer-based technology, applied in the field of polymerizable compounds, can solve problems such as reducing the effective applied voltage, and achieve the effect of high polymerization rate

Active Publication Date: 2014-06-11
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These may be enriched especially on electrodes or alignment layers and reduce the effective applied voltage there

Method used

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  • Polymerisable compounds and the use thereof in liquid-crystal displays
  • Polymerisable compounds and the use thereof in liquid-crystal displays
  • Polymerisable compounds and the use thereof in liquid-crystal displays

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0503] Compound 1 was prepared as follows:

[0504] 1.13-(4-Bromophenyl)propan-1-ol

[0505]

[0506] Firstly, 30.0 g (0.128 mol) of 3-(4-bromophenyl)propionic acid was introduced into 300 ml of THF, and 257 ml (0.257 mol) of a 1 M solution of borohydride in THF were added dropwise under ice cooling. The batch was stirred overnight at room temperature, carefully hydrolyzed with cooling, and extracted three times with MTB ether. The combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed in vacuo and the residue was filtered through silica gel with MTB ether. 3-(4-Bromophenyl)propan-1-ol was obtained, which was used in the next step without further purification.

[0507] 1.23-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl) Phenyl]propan-1-ol

[0508]

[0509] 26.5g (0.123mol) of 3-(4-bromophenyl) propan-1-alcohol and 36.0g (0.139mol) of bis (pinacolate) diboron were dissolved in 400ml ...

Embodiment 2

[0522] Compound 2 was prepared as follows:

[0523] 2.12'-fluoro-4''-(3-hydroxypropyl)-[1,1';4',1'']terphenyl-4-ol

[0524]

[0525] Similar to the synthesis described in 1.4, 3-(4'-bromo-3'-fluorobiphenyl-4-yl)propan-1-ol and 4-(4,4,5,5-tetramethyl-[ 1,3,2]dioxaborolan-2-yl)phenol to give 2'-fluoro-4''-(3-hydroxypropyl)-[1,1';4' as a colorless solid ,1'']terphenyl-4-ol.

[0526] 1 H-NMR (400MHz, DMSO-d 6 )

[0527] δ=1.80ppm(m c ,2H,CH 2 ),2.71(7,J=7.8Hz,2H,Ar-CH 2 -),3.71(7,J=6.5Hz,2H,-CH 2 OH), 4.53(s, br.1H, OH), 6.93(AB-m C , 2H, Ar-H), 7.35(d, J=8.25, 2H, Ar-H), 7.47(AB-dd, J=1.5Hz, J=8.6Hz, 2H, Ar-H), 7.54-7.64( m, 3H, Ar-H), 7.70 (d, J=8.3Hz, 2H, Ar-H), 9.70 (s, 1H, Ar-OH).

[0528] 2.22-Methacrylic acid-2'-fluoro-4''-[3-(2-methacryloyloxy)propane Base]-[1,1';4',1'']terphenyl-4-yl ester (2)

[0529]

[0530] Similar to Example 1, from 2'-fluoro-4''-(3-hydroxypropyl)-[1,1';4',1'']terphenyl-4-ol to obtain 2-Methacrylic acid-2'-fluoro-4''-[3-(2-me...

Embodiment 3-7

[0532] The following compounds were prepared analogously to the methods described in Examples 1 and 2:

[0533]

[0534] (where D represents deuterium)

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Abstract

The present invention relates to polymerisable compounds, to processes and intermediates for the preparation thereof, and to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (FK) media and LC displays, especially in LC displays of the PS or PSA type ('polymer sustained' or 'polymer sustained alignment' respectively).

Description

[0001] This application is a divisional application of the Chinese patent application with application number 201080048338.4. field of invention [0002] The present invention relates to polymerizable compounds, processes for their preparation and their intermediates, and their use for optical, electro-optical or electronic purposes, in particular in liquid crystal (FK) media and liquid crystal displays, especially in PS or PSA (" polymer stabilized" or "polymer stabilized alignment") type of liquid crystal display. Background technique [0003] Currently used liquid crystal displays (FK-displays) are mainly those of the TN (twisted nematic) type. However, they have the drawback of strong viewing angle dependence of contrast. In addition, so-called VA (Vertical Alignment) displays with wider viewing angles are known. The liquid-crystal cell of a VA display contains a layer of a liquid-crystalline medium between two transparent electrodes, the liquid-crystalline medium gene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/14C07C69/653C07C39/367C07C37/18
CPCC09K19/12C09K2019/548C09K2019/123C09K2019/0448C07B2200/05C07C39/367C07C69/54C07C69/653G02F1/13
Inventor A·乔伊塔兹C·马腾S·C·拉乌特A·塔格贝克
Owner MERCK PATENT GMBH