Liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-10131841-B2
Application number	US-201414570268-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Dec 16, 2013
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The invention relates to the compounds of the formula I and to a liquid-crystalline medium based on a mixture of polar compounds which contains at least one compound of the formula I

in which R 1 , ring A 1 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , Z 1 and m have the meanings indicated in claim 1 and to the use of the LC mixtures in electro-optical displays, especially for the self-aligning VA mode.

First claim

The invention claimed is:

1. Liquid-crystalline medium based on a mixture of polar compounds wherein the mixture comprises at least one compound of the formula I,

in which
R 1 denotes a straight-chain alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF 2 O—, —CH═CH—, —⋄—, —⋄⋄—, —CO—O—, or —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by halogen,

Z 1 denotes a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, —C 2 F 4 —, —CHFCHF—, —CH 2 CHF—, —CFHCF 2 —, —CF 2 CHF—, —CHFCH 2 —, —CH 2 CF 2 O—, or —CH═CHCH 2 O—,
L 1 to L 8 each, independently of one another, denote H or alkyl with 1-8 carbon atoms, provided that at least one of L 1 to L 8 denotes alkyl with 1-8 carbon atoms.
m denotes 0, 1, 2, 3, 4, 5 or 6.

2. Liquid-crystalline medium according to claim 1 which further comprises at least one polymerisable compound.

3. Liquid-crystalline medium according to claim 1 wherein the mixture contains 0.01 to 10% by weight of the compound of the formula I based on the mixture as a whole.

4. Liquid-crystalline medium according to claim 1 wherein the at least one compound of the formula I is selected from the following group of compounds of the formula I-1 to I-9,

in which R 1 , Z 1 and m have the meanings as defined in claim 1 and
alkyl and alkyl* each independently denote a straight-chain alkyl radical having 1 to 8 carbon atoms.

5. Liquid-crystalline medium according to claim 2 , wherein the polymerisable compound is selected from the compounds of the formula M
R Ma -A M1 -(Z M1 -A M2 ) m1 -R Mb   M

in which the individual radicals have the following meanings:
R Ma and R Mb each, independently of one another, denote P, P-Sp-, H, halogen, SF 5 , NO 2 , an alkyl, alkenyl or alkynyl group,
P denotes a polymerisable group,
Sp denotes a spacer group or a single bond,
A M1 and A M2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, having 4 to 25 ring atoms, which may also encompass or contain fused rings, and which may optionally be mono- or polysubstituted by L,
L denotes P, P-Sp-, F, Cl, Br, I, SF 5 , —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 denotes halogen,
Z M1 denotes —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 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
R x denotes 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—, 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 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,
m1 denotes 0, 1, 2, 3 or 4, and
n1 denotes 1, 2, 3 or 4,
where at least one group from the group R Ma , R Mb and the substituents L present denotes a group P or P-Sp- or contains at least one group P or P-Sp-.

6. Liquid-crystalline medium according to claim 5 , wherein the polymerisable compound of the formula M is selected from the group of compounds of the formula M1to M41,

in which the individual radicals have the following meanings:
P 1 , P 2 and P 3 each, independently of one another, denote a polymerisable group,
Sp 1 , Sp 2 and Sp 3 each, independently of one another, denote a single bond or a spacer group,
where, in addition, one or more of the radicals P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - may 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 does not denote R aa ,

R aa denotes 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—, 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 be replaced by F, Cl, CN or P 1 -Sp 1 -,
R 0 and R 00 each, independently of one another and identically or differently on each occurrence, denote H or alkyl having 1 to 12 C atoms,
R y and R z each, independently of one another, denote H, F, CH 3 or CF 3 ,
X 1 , X 2 and X 3 each, independently of one another, denote —CO—O—, —O—CO— or a single bond,
Z 1 denotes —O—, —CO—, —C(R y R z )—or —CF 2 CF 2 —,
Z 2 and Z 3 each, independently of one another, denote —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —(CH 2 ) n —, where n is 2, 3 or 4,
L on each occurrence, identically or differently, denotes F, Cl, CN or straight-chain or branched, optionally mono—or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
L′ and L″ each, independently of one another, denote H, F or Cl,
r denotes 0, 1, 2, 3 or 4,
s denotes 0, 1, 2 or 3,
t denotes 0, 1 or 2, and
x denotes 0 or 1.

7. Liquid-crystalline medium according to claim 1 , wherein the medium additionally contains one or more compounds selected from the group of the compounds of the formulae IIA, IIB and IIC

in which
R 2A , R 2B and R 2C each, independently of one another, denote H, an alkyl or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals may be replaced by —O—, —S

Assignees

• Merck Patent Gmbh

Inventors

• Archetti Graziano
• Saito Izumi
• Fortte Rocco
• Uebel Timo

Classifications

• C09K19/0403 Primary

  the structure containing one or more specific, optionally substituted ring or ring systems · CPC title

• C09K2019/0437

  the specific unit being an optically active chain used as linking group between rings or as end group · CPC title

• C09K19/3048

  in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/0466

  the linking chain being a -CF2O- chain · CPC title