Liquid crystal medium containing polymerisable compounds

Patent metadata

Field	Value
Publication number	US-10894918-B2
Application number	US-201615739190-A
Country	US
Kind code	B2
Filing date	May 31, 2016
Priority date	Jun 26, 2015
Publication date	Jan 19, 2021
Grant date	Jan 19, 2021

Abstract

The present invention relates to a liquid crystal (LC) medium comprising polymerisable compounds, to a process for its preparation, to its use for optical, electro-optical and electronic purposes, in particular in LC displays, and to LC displays comprising it.

First claim

The invention claimed is:

1. A liquid crystal (LC) medium comprising
a polymerizable component A) which comprises
one or more first polymerizable compounds comprising only one polymerizable group and a bi- or polycyclic hydrocarbon group which is non-aromatic, and
one or more second polymerizable compounds comprising a polymerizable group and a straight-chain, branched or monocyclic hydrocarbon group which is non-aromatic,
optionally a photoinitiator; and
a liquid-crystalline component B) which comprises one or more compounds selected from formula CY and formula PY

wherein
a denotes 1 or 2,
b denotes 0 or 1,

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups may each be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x and Z y each, independently of one another, 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, and
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 ;

wherein the liquid-crystalline component B) has a negative dielectric anisotropy; and
wherein
the concentration of the first and second polymerizable compounds in the LC medium is from 15 to 25% by weight, or
the concentration of the first and second polymerizable compounds in the LC medium is from 10 to 20% by weight.

2. The LC medium of claim 1 , wherein component A) comprises one or more first polymerizable compounds selected from formula I
P-Sp-G 1   I

wherein
P is a polymerizable group,
Sp is a spacer group or a single bond,
G 1 is a bi-, tri- or tetracyclic hydrocarbon group having 6 to 20 ring atoms which is optionally substituted by one or more groups L,
L is F, Cl, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may each be replaced by F, Cl, or —CN,
R x is H, F, Cl, CN, or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are each optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— 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 are H or alkyl having 1 to 20 C atoms, and
Y 1 is halogen.

3. The LC medium according to claim 2 , wherein component A) comprises one or more first polymerizable compounds selected from the following formulae

wherein
P and Sp have the meanings given in claim 2 ,
W 11 , W 12 and W 13 are independently of each other H, F or C 1 -C 12 -alkyl, and
the cycloalkyl groups are optionally substituted with one or more groups L as defined in claim 2 .

4. The LC medium according to claim 1 , wherein component A) comprises one or more first polymerizable compounds selected from the following formulae

5. The LC medium according to claim 1 , wherein component A) comprises one or more second polymerizable compounds selected from formula II
P-Sp-G 2   II

wherein
P is a polymerizable group,
Sp is a spacer group or a single bond,
G 2 is a straight-chain, branched or monocyclic alkyl group with 1 to 20 C atoms that is optionally mono-, poly- or perfluorinated and is optionally substituted by one or more groups L and wherein one or more CH 2 -groups are optionally replaced by —O—, —CO—, —O—CO— or —CO—O— such that O-atoms are not directly adjacent to one another, and
L is F, Cl, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may each be replaced by F, Cl, or —CN.

6. The LC medium according to claim 1 , wherein component A) comprises one or more second polymerizable compounds selected from the following formulae

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
P is a polymerizable group,
Sp is a spacer group or single bond,
W 11 , W 12 are each independently H, F or C 1 -C 12 -alkyl,
W 13 , W 14 are each independently H or F,
n1 is an integer from 2 to 15, and
n2, n3 are each independently 0 or an integer from 1 to 3.

7. The LC medium according to claim 1 , wherein component A) comprises one or more second polymerizable compounds selected from the following formulae

8. The LC medium according to claim 1 , wherein component A) additionally comprises one or more second polymerizable compounds having two or more polymerizable groups and a straight-chain, branched or monocyclic hydrocarbon group.

9. The LC medium according to claim 1 , wherein component A) additionally comprises one or more second polymerizable compounds selected from formula IV
P 1 -Sp 1 -G 2 -Sp 2 -P 2   IV

wherein
P 1 , P 2 are each independently a polymerizable group,
Sp 1 , Sp 2 are each independently a spacer group or single bond,
G 2 is a straight-chain, branched or monocyclic alkyl group with 1 to 20 C atoms that is optionally mono-, poly- or perfluorinated and is optionally substituted by one or more groups L, and wherein one or more CH 2 -groups are each optionally replaced by —O—, —CO—, —O—CO— or —CO—O— such that O-atoms are not directly adjacent to one another, and
L is F, Cl, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —O—, —S—, —CO—, —CO—

Assignees

• Merck Patent Gmbh

Inventors

• Klasen-Memmer Melanie
• Greinert Nils
• Bremer Matthias
• Schneider Konstantin
• Schoenefeld Christian
• Bauer Thomas

Classifications

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/124

  Ph-Ph-Ph-Ph · CPC title