Liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-11214736-B2
Application number	US-201615512940-A
Country	US
Kind code	B2
Filing date	Sep 8, 2016
Priority date	Sep 9, 2015
Publication date	Jan 4, 2022
Grant date	Jan 4, 2022

Abstract

Compounds of the formula I, liquid-crystalline media which contain at least one compound of the formula I and electro-optical displays which contain the LC mixtures, especially for the self-aligning VA, PSA, PS-VA, PVA, MVA, PM-VA, HT-VA or VA-IPS modein which R1, R2, ring A1, Z1, Z2, Sp, P, L1, L2, r1, r2, r3, m, n, p1 and p2 have the meanings indicated above.

First claim

The invention claimed is:

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

in which
R 1 denotes H, an 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 —CH═CH—, —C≡C—, —CF 2 O—, —CH═CH—,

—O—, —CO—O—, —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,
R 2 denotes an alkyl radical having 1 to 8 C atoms,

Denotes

L 1 and L 2 in each case, independently of one another, denotes F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, straight-chain alkyl having 1 to 5 C atoms, branched alkyl having 3 to 5 C atoms, alkoxy having 1 to 5 C atoms, alkylcarbonyl having 2 to 5 C atoms, alkoxycarbonyl having 2 to 5 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
L 3 in each case, independently of one another, denotes Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, straight-chain alkyl having 1 to 5 C atoms, branched alkyl having 3 to 5 C atoms, alkoxy having 1 to 5 C atoms, alkylcarbonyl having 2 to 5 C atoms, alkoxycarbonyl having 2 to 5 C atoms, alkylcarbonyloxy having 2 to 5 C atoms or alkoxycarbonyloxy having 2 to 5 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
m denotes 0, 1 or 2,
n denotes 1 or 2,
P denotes a polymerisable group,
Sp denotes a spacer group or a single bond,
Z 1 and Z 2 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO— or —OCO—CH═CH—,
p1 denotes 1, 2 or 3,
r1 denotes 0, 1, 2 or 3, whereas p1+r1≤4,
p2 denotes 0, 1, 2 or 3
r2 denotes 1, 2 or 3, whereas p2+r2≤4.

2. Liquid-crystalline medium according to claim 1 which contains at least one compound of the formula I*,

in which
R 1 denotes H, an 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 —CH═CH—, —C≡C—, —CF 2 O—, —CH═CH—,

—O—, —CO—O—, —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,
R 2 denotes an alkyl radical having 1 to 8 C atoms,

Denotes

L 1 and L 2 in each case, independently of one another, denotes F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, straight-chain alkyl having 1 to 5 C atoms, branched alkyl having 3 to 5 C atoms, alkoxy having 1 to 5 C atoms, alkylcarbonyl having 2 to 5 C atoms, alkoxycarbonyl having 2 to 5 C atoms, alkylcarbonyloxy having 2 to 5 C atoms or alkoxycarbonyloxy having 2 to 5 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
P denotes a polymerisable group,
Sp denotes a spacer group or a single bond,
Z 1 and Z 2 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, CH 2 CF 2 —, —CF 2 —CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO— or —OCO—CH═CH—,
p1 denotes 1, 2 or 3,
r1 denotes 0, 1, 2 or 3, whereas p1+r1≤4,
p2 denotes 0, 1, 2 or 3
r2 denotes 1, 2 or 3, whereas p2+r2≤4.

3. Liquid-crystalline medium according to claim 2 wherein the compound of the formula I is selected from the following group of compounds of the formula I-A to I-H,

in which
R a denotes

and
R 1 denotes H, an 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 —CH═CH—, —C≡C—, —CH═CH—,

—O—, —CO—O—, —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,
R 2 denotes an alkyl radical having 1 to 8 C atoms,
L 1 and L 2 in each case, independently of one another, denotes F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, straight-chain alkyl having 1 to 5 C atoms, branched alkyl having 3 to 5 C atoms, alkoxy having 1 to 5 C atoms, alkylcarbonyl having 2 to 5 C atoms, alkoxycarbonyl having 2 to 5 C atoms, alkylcarbonyloxy having 2 to 5 C atoms or alkoxycarbonyloxy having 2 to 5 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
m denotes 0, 1 or 2,
P denotes a polymerisable group,
Sp denotes a spacer group or a single bond, and
Z 1 and Z 2 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO— or —OCO—CH═CH—,
L 3 in each case, independently of one another, denotes Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, straight-chain alkyl having 1 to 5 C atoms, branched alkyl having 3 to 5 C atoms, alkoxy having 1 to 5 C atoms, alkylcarbonyl having 2 to 5 C atoms, alkoxycarbonyl having 2 to 5 C atoms, alkylcarbonyloxy having 2 to 5 C atoms or alkoxycarbonyloxy having 2 to 5 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
r1 denotes 0, 1, 2 or 3, whereas p1+r1≤4,
r2 denotes 1, 2 or 3, whereas p2+r2≤4.

4. Liquid-crystalline medium according to claim 1 wherein the medium contains at least one compound selected from the following group of compounds of the formula I-1 to I-79

Assignees

• Merck Patent Gmbh

Inventors

• Archetti Graziano
• Neumann Elena
• Fortte Rocco
• Uebel Timo
• Haensel Helmut
• Mueller Kristin

Classifications

• G02F1/133703

  by introducing organic surfactant additives into the liquid crystal material · CPC title

• C09K19/46 Primary

  containing esters · CPC title

• C09K2019/3063

  Cy-Ph-C≡C-Ph · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title