Liquid crystal medium containing polymerisable compounds

Patent metadata

Field	Value
Publication number	US-10570335-B2
Application number	US-201615739210-A
Country	US
Kind code	B2
Filing date	Jun 2, 2016
Priority date	Jun 26, 2015
Publication date	Feb 25, 2020
Grant date	Feb 25, 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, selected from the following formulae I1 to I4:

wherein
P is a polymerisable group,
Sp is a spacer group or a single bond,
W 11 , W 12 and W 13 are independently of each other H, F or C 1 -C 12 -alkyl, and
the cycloalkyl ring system in each of formulae I1 to I4 is optionally substituted with one or more groups L, where 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—, —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;

one or more second polymerisable compounds comprising a polymerisable group and a straight-chain, branched or monocyclic hydrocarbon group, selected from compounds of the formula II:
P-Sp-G 2   II

wherein P and Sp independently have the meanings given above, 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 independently as defined above, and wherein one or more CH 2 -groups in the alkyl group are optionally replaced by —O—, —CO—, —O—CO— or —CO—O— such that O-atoms are not directly adjacent to one another; and
a liquid-cystalline component B) which comprises one or more compounds selected from formula A and B:

in which the individual radicals have, independently of each other and on each occurrence identically or differently, the following meanings:

each, independently of one another, and on each occurrence, identically or differently, are:

R 21 , R 31 each, independently of one another, are alkyl, alkoxy, oxaalkyl or alkoxyalkyl having 1 to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,
X 0 is F, Cl, halogenated alkyl or alkoxy having 1 to 6 C atoms or halogenated alkenyl or alkenyloxy having 2 to 6 C atoms,
z 31 is —CH 2 CH 2 —, —CF 2 CF 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O— or a single bond,
L 21 , L 22 , L 31 , L 32 each, independently of one another, are H or F, and
g is 0, 1, 2 or 3.

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

3. The LC medium according to claim 1 , 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 1 ,
W 11 , W 12 are H, F or 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 is an integer from 1 to 5, and
n6, n7 are 0 or an integer from 1 to 15.

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

5. The LC medium according to claim 1 , wherein component A) further comprises one or more polymerisable compounds which have two or more polymerisable groups and a straight-chain, branched or monocyclic hydrocarbon group.

6. The LC medium according to claim 5 , wherein the further one or more polymerisable compounds which have two or more polymerisable groups are selected from compounds of the formula IV:
P 1 -Sp 1 -G 2 -Sp 2 -P 2   IV

wherein
G 2 is as previously defined, P 1 and P 2 are, independently, as defined for P and Sp 1 and Sp 2 are, independently, as defined for Sp.

7. The LC medium according to claim 6 , wherein the further one or more component A) polymerisable compounds which have two or more polymerisable groups are selected from compounds of the following formulae:

wherein P 1 , P 2 , Sp 1 , Sp 2 are as defined in claim 6 ,
W 11 , W 12 are H, F or 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 is an integer from 1 to 5,
n6, n7 are 0 or an integer from 1 to 15 and
the cyclohexylene ring in formula IV2 is optionally substituted by one or more identical or different groups W 11 .

8. The LC medium according to claim 6 , wherein the further one or more polymerisable compounds which have two or more polymerisable groups are selected from compounds of the following formulae

9. The LC medium according to claim 1 , wherein the concentration of the first and second polymerisable compounds in the LC medium is from 1 to 30% by weight.

10. The LC medium according to claim 1 , wherein the ratio of first polymerisable compounds relative to the second polymerisable compounds in the LC medium is from 10:1 to 1:10.

11. The LC medium according to claim 1 , wherein component B)

Assignees

• Merck Patent Gmbh
• Merck Patetn Gmbh

Inventors

• Song Dong-Mee
• Kwon Ki-Sun
• Lee Hoo-Yong
• Klasen-Memmer Melanie
• Schoenefeld Christian
• Schneider Konstantin
• Koch Matthias
• Peschke Joerg
• Bremer Matthias
• Greinert Nils

Classifications

• C09K2019/3021

  Cy-Ph-Ph-Cy · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K19/06

  Non-steroidal liquid crystal compounds · CPC title

• C09K19/20

  linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers} · CPC title