Liquid crystal medium containing polymerisable compounds

Patent metadata

Field	Value
Publication number	US-10590344-B2
Application number	US-201615739358-A
Country	US
Kind code	B2
Filing date	Jun 3, 2016
Priority date	Jun 26, 2015
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

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 polymerisable component A) which comprises
one or more first polymerisable compounds comprising a polymerisable group and a bi- or polycylic hydrocarbon group, and
one or more second polymerisable compounds comprising a polymerisable group and a straight-chain, branched or monocyclic hydrocarbon group, and
one or more third polymerisable compounds comprising a straight-chain, branched or monocyclic hydrocarbon group and attached thereto two polymerisable groups that are different from each other.

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

wherein
P is a polymerisable 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 C atoms, 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≡—, —N(R 0 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, —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 be replaced by F, Cl, —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 optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —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 polymerisable 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 polymerisable compounds selected from the following formulae

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

wherein P and Sp have the meanings given in claim 2 , and 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 as defined in claim 2 , 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.

6. The LC medium according to claim 2 , wherein component A) comprises one or more second polymerisable 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, Sp are as defined in claim 2 ,
W 11 , W 12 are H, F or straight chain or branched C 1 -C 12 -alkyl,
W 13 , W 14 are H or F,
n1 is an integer from 2 to 15,
n2, n3 are 0 or an integer from 1 to 3,
n5 an integer from 1 to 5, and
n6, n7 0 or an integer from 1 to 15.

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

8. The LC medium according to claim 1 , wherein component A) comprises one or more third polymerisable compounds selected of formula III
P 1 -Sp 1 -G 3 -Sp 2 -P 2   III

wherein
P 1 and P 2 denote polymerisable groups that are different from each other,

Sp 1 , Sp 2 denote independently of each other identical or different spacer groups or a single bond,
G 3 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 Las defined in formula I, 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 C atoms, 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—, —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 be replaced by F, Cl, —CN.

9. The LC medium according to claim 1 , wherein, in the third polymerisable compounds, the polymerisable groups are selected from acrylate, methacrylate, ethacrylate and vinyloxy groups.

10. The LC medium according to claim 8 , wherein component A) comprises one or more third polymerisable compounds selected from the following formulae

wherein P 1 , P 2 , Sp 1 , Sp 2 are as defined in claim 8 ,
W 11 is, on each occurrence identically or differently, H, F or C 1 -C 12 -alkyl,
n1 is an integer from 2 to 15,
n2, n3 are independently of each other 0 or an integer from 1 to 3,
n4 is 0 or an integer from 1 to 15,
and the cyclohexylene ring in formula III2 is optionally substituted by one or more identical or different groups W 11 .

11. The LC medium according to claim 1 , wherein component A) comprises one or more third polymerisable compounds selected from the following formulae

12. The LC medium according to claim 1 , wherein component A) comprises one or more fourth polymerisable compounds comprising a ring system containing one or more aromatic or heteroaromatic rings or condensed aromatic or heteroaromatic rings, and attached thereto two polymerisable groups

Assignees

• Merck Patent Gmbh

Inventors

• Klasen-Memmer Melanie
• Greinert Nils
• Bremer Matthias
• Taugerbeck Andreas
• Schoenefeld Christian
• Suess Patrick

Classifications

• C09K19/2007

  the chain containing -COO- or -OCO- groups · CPC title

• C09K19/061 Primary

  Linear compounds without any rings · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K19/3068

  chain containing -COO- or -OCO- groups · CPC title