Liquid crystal medium

Patent metadata

Field	Value
Publication number	US-9963637-B2
Application number	US-201615200201-A
Country	US
Kind code	B2
Filing date	Jul 1, 2016
Priority date	Jul 2, 2015
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

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

First claim

The invention claimed is:

1. A liquid crystalline medium comprising
a polymerizable component A) comprising one or more polymerizable compounds, and
a liquid-crystalline host mixture component B), comprising one or more mesogenic or liquid-crystalline compounds,
wherein component B) comprises from 0.01 to 2% of one or more compounds of formula A

in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
R 1 , R 2 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,
L 1 , L 2 , L 3 are F or Cl.

2. The liquid crystalline medium of claim 1 , wherein the compounds of formula A are of the formula:

wherein alkyl denotes a straight-chain alkyl radical having 1-6 C atoms, and n is 0 or 1.

3. The liquid crystalline medium of claim 1 , wherein component B) comprises from 0.01 to 1% of compounds of formula A.

4. The liquid crystalline medium according to claim 1 , wherein component A) comprises one or more polymerizable compounds of formula I
R a —B 1 —(Z b —B 2 ) m —R b   I

in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
R a and R b are P, P-Sp-, H, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, SF 5 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 00 )—, —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, Br, I, CN, P or P-Sp-, where, if B 1 and/or B 2 contain a saturated C atom, R a and/or R b may also denote a radical which is spiro-linked to this saturated C atom,
wherein at least one of the radicals R a and R b denotes or contains a group P or P-Sp-,
P is a polymerizable group,
Sp is a spacer group or a single bond,
B 1 and B 2 are an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,

Z b is —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2— , —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,
R 0 and R 00 is H or alkyl having 1 to 12 C atoms,
m is 0, 1, 2, 3 or 4,
n1 is 1, 2, 3 or 4,

L is P, P-Sp-, OH, CH 2 OH, F, Cl, Br, I, —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 having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-,
Y 1 is halogen, and

R x is P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —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, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.

5. The liquid crystalline medium according to claim 4 , wherein the polymerizable compounds of formula I B 1 and B 2 each, independently of one another, are 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, 9,10-dihydro-phenanthrene-2,7-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, coumarine, flavone, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by O and/or S, 1,4-cyclohexenylene, bicycle[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl or octahydro-4,7-methanoindane-2,5-diyl, where all these groups may be unsubstituted or mono- or polysubstituted by L.

6. The liquid crystalline medium according to claim 4 , wherein the polymerizable compounds of formula I are:

in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
P 1 , P 2 , P 3 are a vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane or epoxy group,
Sp 1 , Sp 2 , Sp 3 are a single bond or a spacer group where, in addition, one or more of the radicals P 1 -Sp 1 -, P 1 -Sp 2 - and P 3 -Sp 3 - may also denote R aa , with the proviso that at least one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 and P 3 -Sp 3 - present is different from R aa ,
R aa is H, F, Cl, CN 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 or P 1 -Sp 1 -, particularly preferably straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms (where the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms),
R 0 , R 00 H or alkyl having 1 to 12 C atoms,
R y and R z H, F, CH 3 or CF 3 ,
X 1 , X 2 , X 3 —CO—O—, —O—CO— or a single bond,
Z 1 —O—, —CO—, —C(R y R z )— or —CF 2 CF 2 —,
Z 2 , Z 3 —CO—O—,—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—,—OCF 2 — or —(CH 2 ) n —, where n is 2, 3 or 4,
L F, Cl, CN or straight-chain or branched, optionally mono- or poly-fluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
L′, L″ H, F or Cl,
r 0, 1, 2, 3 or 4,
s 0, 1, 2 or 3,
t 0, 1 or 2,
x 0 or 1.

7. The liquid crystalline medium according to claim 6 , wherein the polymerizable compounds of formula I are of the formulae M2, M13, M17, M22, M23, M24 or M30.

8. The liquid crystalline medium according to claim 1 , wherein the component B) additionally comprises one or more compounds of formulae AN or AY which are different from formula A:

Assignees

• Merck Patent Gmbh

Inventors

• Lee Eun-Kyu
• Yoon Hyun-Jin
• Jeong Ji-Won
• Park Hye-Ryung
• Kim Seung-Jai
• Ji Yong-Jun
• Jin Min-Ok
• Yun Yong-Kuk

Classifications

• C09K2019/3009

  Cy-Ph · CPC title

• G02F2202/022

  polymeric · CPC title

• C09K19/3098 Primary

  Unsaturated non-aromatic rings, e.g. cyclohexene rings · CPC title

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title