Liquid-crystal medium comprising polymerizable compounds

Patent metadata

Field	Value
Publication number	US-12492344-B2
Application number	US-202118035648-A
Country	US
Kind code	B2
Filing date	Nov 3, 2021
Priority date	Nov 6, 2020
Publication date	Dec 9, 2025
Grant date	Dec 9, 2025

Abstract

A polymerizable compound having absorption in the long UV wavelength range, a liquid-crystal (LC) medium comprising the polymerizable compound, and the use of the compound or LC medium for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the PSA (polymer sustained alignment) or SA (self-aligning) mode, an LC display of the PSA or SA mode comprising the compound or LC medium, and a process of manufacturing the LC display.

First claim

The invention claimed is:

1 . A polymerizable compound of formula I1:

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings:
P denotes acrylate or methacrylate;
Sp denotes a single bond;
L denotes F, Cl, Br, —CN or straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —N(R 0 )—, —Si(R 0 R 00 )—, —CH═CH—, or —C≡C— in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl;
R 0 , R 00 denote H or alkyl with 1 to 12 C atoms; and
r1 denotes 0, 1, 2, 3, or 4.

2 . The compound according to claim 1 , wherein L is selected from F, CH 3 , OCH 3 , OC 2 H 5 , C 3 H 5 , CH═CH 2 , and C(CH 3 )═CH 2 .

3 . The compound according to claim 1 , wherein the compound of formula I1 comprises one or more compounds selected from subformulae I1-1 to I1-18:

4 . An LC medium comprising one or more compounds according to claim 1 .

5 . The LC medium according to claim 4 , further comprising one or more compounds of formula II:

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings:
R 1 and R 2 denote straight chain, cyclic alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl;
A 1 and A 2 denote a group selected from the following formulae;

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings;
Z 1 and Z 2 denote —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond;
L 1 , L 2 , L 3 , and L 4
denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 ;

Y denotes H, F, Cl, CF 3 , CHF 2 , or CH 3 ;
L c denotes CH 3 or OCH 3 ;
a1 denotes 1 or 2; and
a2 denotes 0 or 1.

6 . The LC medium according to claim 5 , further comprising one or more compounds of formula II selected from the group consisting of compounds of the formulae IIA, IIB, IIC, and IID:

in which
R 2A and R 2B
each, independently of one another, denote H or an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 , or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals are optionally replaced by —O—, —S—,

—C≡C—, —CF 2 O—, —OCF 2 —, —OC—O—, or —O—CO— in such a way that O atoms are not linked directly to one another;
L 1 to L 4 each, independently of one another, denote F, Cl, CF 3 , or CHF 2 ;
Y denotes H, F, Cl, CF 3 , CHF 2 , or CH 3 ;
Z 2 , Z 2B , and Z 2D
each, independently of one another, denote a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, or —CH═CHCH 2 O—;

p denotes 0, 1, or 2; and
q on each occurrence, identically or differently, denotes 0 or 1.

7 . The LC medium according to claim 5 , further comprising one or more compounds of formula III:

in which
R 11 and R 12
each, independently of one another, denote H, or an alkyl or alkoxy radical having 1 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

—C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, by —O—, —CO—O—, or —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms are optionally replaced by halogen;
A 3 on each occurrence, independently of one another, denotes
a) 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH 2 groups are optionally replaced by —O— or —S—,
b) a 1,4-phenylene radical, in which one or two CH groups are optionally replaced by N, or
c) a radical selected from the group consisting of spiro[3.3] heptane-2,6-diyl, 1,4-bicyclo[2.2.2] octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl, and fluorene-2,7-diyl,
wherein the radicals a), b), and c) are optionally mono- or polysubstituted by halogen atoms;

n denotes 0, 1, or 2;
Z 1 on each occurrence independently of one another denotes-CO—O—, —O—CO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CH 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—CH 2 O—, —C 2 F 4 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF═CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C≡C—, or a single bond;
L 11 and L 12 each, independently of one another, denote F, Cl, CF 3 , or CHF 2 ; and
W denotes O or S.

8 . The LC medium according to claim 5 , further comprising one or more compounds of formula IV:

in which
R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms; and
R 42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkoxy radical having 1 to 6 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms.

9 . The LC medium according to claim 5 , further comprising one or more compounds of formula V:

in which
R 51 and R 52
independently of one another, denote an unsubstituted alkyl radical having 1 to 7 C atoms, an unsubstituted alkenyl radical having 2 to 7 C atoms, or an unsubstituted alkoxy radical having 1 to 6 C atoms;

identically or differently, denote

Z 51 —, Z 52 each, independently of one another, denote-CH 2 —CH 2 —, —CH 2 —O—, —CH═CH—, —C≡C—, —COO—, or a single bond; and
n is 1 or 2.

10 . T

Assignees

• Merck Patent Gmbh

Inventors

• Uebel Timo
• Fortte Rocco
• Tong qiong
• Hsieh Chia-Sheng
• Huang I-Hua
• Weegels Leo

Classifications

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• C09K19/3491

  having sulfur as hetero atom · CPC title

• C08F122/20

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C08F122/18

  Esters containing halogen · CPC title

• C08F122/14

  Esters having no free carboxylic acid groups · CPC title