Liquid crystal medium

Patent metadata

Field	Value
Publication number	US-10851301-B2
Application number	US-201514940599-A
Country	US
Kind code	B2
Filing date	Nov 13, 2015
Priority date	Nov 14, 2014
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

The present invention relates to a liquid crystal (LC) medium comprising a terphenyl compound and at least two polymerizable compounds, to a process for its preparation, to its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in an LC display of the polymer sustained alignment (PSA) type, and to an LC display, especially a PSA display, comprising it.

First claim

The invention claimed is:

1. A liquid crystal (LC) medium comprising
at least one direactive polymerizable compound having two polymerizable groups at a concentration above 0% and ≤1% by weight,
at least one trireactive polymerizable compound having three polymerizable groups at a concentration above 0% and ≤0.5% by weight,
at least one unpolymerizable terphenyl compound of formula T1 to T22 or T24 at a concentration above 0% and ≤3% by weight,

in which
R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms,
R* denotes a straight-chain alkenyl radical having 2-7 C atoms,
(O) denotes an oxygen atom or a single bond, and
m denotes an integer from 1 to 6.

2. The LC medium of claim 1 , which contains at least one compound of formula T1, T2, T3 or T21

in which
R denotes a straight-chain alkyl or alkoxy radical having 1-5 C atoms,
(O) denotes an oxygen atom or a single bond, and
m denotes an integer from 1 to 6.

3. The LC medium of claim 1 , comprising one or more direactive polymerizable compounds of the following formulae

in which each variable on each occurrence identically or differently, independently of one another, has the following meaning:
Sp 1 , Sp 2 is a spacer group or a single bond,
P 1 , P 2 is a polymerizable group,
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 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 one or more H atoms may be replaced by F, Cl or CN,
Z 1-3 —O—, —CO—, —CO—O—, —O—CO—, —C(R y R z )—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CH 2 CH 2 — or —CF 2 CF 2 —,
R x 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 y , R z H, F, CH 3 or CF 3 ,
R 0 , R 00 H or alkyl having 1 to 20 C atoms,
Y 1 halogen,
r 0, 1, 2, 3 or 4,
s 0, 1, 2 or 3,
t 0, 1 or 2.

4. The LC medium according to claim 1 , comprising at least one trireactive polymerizable compound of the following formulae

in which
Sp 1 , Sp 2 is a spacer group or a single bond,
P 1 , P 2 is a polymerizable group,
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 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 one or more H atoms may be replaced by F, Cl or CN,
P 3 has one of the meanings given for P 1 ,
Sp 3 has one of the meanings given for Sp 1 ,
r is 0-4,
s is 0-3, and
t is 0-2.

5. The LC medium according to claim 1 , comprising at least one compound of formulae AN and AY

in which each variable, on each occurrence identically or differently, independently of one another, has the following meaning:

R A1 is alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, may have one of the meanings of R A2 ,
R A2 is alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may 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 is —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 and L 2 are H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 H,
x is 1 or 2, and
z is 0 or 1.

6. The LC medium according to claim 1 , which comprises one or more compounds of formulae CY or 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 one or two non-adjacent CH 2 groups may 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 .

7. The LC medium according to claim 1 , comprising at least one compound of the formula:

in which the individual radicals have the following meanings:

R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another, and
Z y denotes —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 a single bond.

8. A liquid crystal (LC) medium comprising a polymerizable component A) comprising
at least one direactive polymerizable compound selected from the following compounds

in which each variable on each occurrence identically or differently, independently of one another, has the following meaning:
Sp 1 , Sp 2 is a spacer group or a single bond,
P 1 , P 2 is a polymerizable group,
L is F, Cl, —CN, —NO 2 , —

Assignees

• Merck Patent Gmbh

Inventors

• Yoon Hyun-Jin
• Jeong Ji-Won
• Lee Eun-Kyu
• Jin Min-Ok
• Yun Yong-Kuk

Classifications

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/06

  Non-steroidal liquid crystal compounds · CPC title

• C09K2019/127

  Compounds containing phenylene-1,3-diyl · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title