Polymerizable compounds and their use in liquid-crystal displays

A technology for polymerizing compounds and liquid crystal displays, applied in liquid crystal materials, chemical instruments and methods, etc., can solve problems such as reducing the effective applied voltage, and achieve the effect of high polymerization rate

Active Publication Date: 2012-07-04
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These can accumulate, especially on electrodes or alignme

Method used

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  • Polymerizable compounds and their use in liquid-crystal displays
  • Polymerizable compounds and their use in liquid-crystal displays
  • Polymerizable compounds and their use in liquid-crystal displays

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0553] 2-Methacrylic acid-4′-[4-(2-methacryloyloxy)-but-1-ynyl]-biphenyl -4-yl esters (1)

[0554] 1.1 4′-(4-Hydroxybut-1-ynyl)-biphenyl-4-ol

[0555]

[0556] 17.2g (69.0mmol) of 4-bromo-4'-hydroxybiphenyl, 10.0g (143mmol) of but-3-yn-1-alcohol, 2.00g (2.85mmol) of bis (triphenylphosphine) palladium (II) Chloride, 0.7 g of copper(I) iodide and 25 ml (178 mmol) of diisopropylamine were heated at reflux in 150 ml of THF overnight. The batch is then added to 200 ml of MTB ether, 400 ml of water are added and acidified with hydrochloric acid. The aqueous phase was separated and extracted three times with ethyl acetate. The combined organic phases are concentrated in vacuo and the residue is filtered through silica gel with dichloromethane / ethyl acetate (3:1). Crystallization of the crude product from toluene yielded 4'-(4-hydroxybut-1-ynyl)biphenyl-4-ol as a colorless solid.

[0557] 1.2 2-Methacrylic acid-4′-[4-(2-methacryloyloxy)but-1-ynyl]link Phenyl-4-yl este...

Embodiment 2

[0563] 2-Methacrylic acid 4-{4′-[4-(2-methacryloyloxy)but-1-ynyl]-biphenyl -4-yl}but-3-ynyl ester (2)

[0564]

[0565] Analogously to Example 1, 2-methacrylic acid-4-{4'-[4-(2-methacryloyloxy )but-1-ynyl]biphenyl-4-yl}but-3-ynyl ester 2.

[0566] 1 H-NMR (400MHz, CDCl 3 ):

[0567] δ=1.98ppm (m c , 6H, Me), 2.82 (t, J=6.9Hz, 4H, -C≡CCH 2 -), 4.35(t, J=6.9Hz, 4H, -CH 2 O-), 5.60 (quint., J=1.6Hz, 2H, -C=CH A h B -), 6.18 (m c , 2H, C=CH A h B ), 7.48 (AB-m c , where: J=8.4Hz, 8H, Ar-H).

Embodiment 3

[0569] 2-Methacrylic acid 4-{6-[4-(2-methacryloyloxy)but-1-ynyl]naphthalene-2-yl} But-3-ynyl ester (3)

[0570]

[0571] Analogously to Example 2, 2-methacrylic acid-4-{6-[4-(2-methacryloyloxy)butyl- 1-Alkynyl]naphthalen-2-yl}but-3-ynyl ester 3.

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Abstract

The present invention relates to polymerizable compounds, to processes and intermediates for preparing them, and to their use for optical, electro-optical and electronic purposes, more particularly in liquid-crystal (LC) media and LC displays, especially in LC displays of the PS or PSA ("polymer sustained" or "polymer sustained alignment") type.

Description

field of invention [0001] The present invention relates to polymerizable compounds, processes for their preparation and their intermediates, and their use for optical, electro-optical and 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 [0002] 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 generally having a negative dielectric (DK-) anisotropy value. In the de-energized state, the molecules of the liquid crystal laye...

Claims

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Application Information

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IPC IPC(8): C09K19/04
CPCC09K2019/548C09K2019/0448C09K19/0403C09K2323/00C09K19/10C09K19/12C09K19/20
Inventor A·塔格贝克A·乔伊塔兹
Owner MERCK PATENT GMBH
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