Liquid-crystal medium

Patent metadata

Field	Value
Publication number	US-12104109-B2
Application number	US-202318213024-A
Country	US
Kind code	B2
Filing date	Jun 22, 2023
Priority date	Jun 23, 2022
Publication date	Oct 1, 2024
Grant date	Oct 1, 2024

Abstract

A liquid-crystal (LC) material having negative dielectric anisotropy and the use thereof for optical, electro-optical and electronic purposes, such as for example in LC displays, in particular energy saving displays based on the ECB, IPS or FFS effect, where the liquid crystal medium contains one or more compounds of formula Iand one or more compounds compounds of formulae IIA, IIB, IIC and IID

First claim

The invention claimed is:

1. A liquid crystal medium comprising
a) one or more compounds of formula I

in which
R 1 and R 2 , identically or differently, denote H, halogen, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl or alkoxy or alkenyl or alkenyloxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

 —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
A 0 , A 1 , and A 2 , each, independently of one another, denote phenylene-1,4-diyl, in which one or two CH groups may be replaced by N and one or more H atoms may be replaced by halogen, CN, CH 3 , CHF 2 , CH 2 F, CF 3 , OCH 3 , OCHF 2 or OCF 3 , or denote cyclohexane-1,4-diyl, in which one or two non-adjacent CH 2 groups may be replaced, independently of one another, by O and/or S and one or more H atoms may be replaced by F, or denote cyclohexene-1,4-diyl, bicyclo[1.1.1]-pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl,
Z 1 and Z 2 , each, independently of one another, denote —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 H 4 —, —C 2 F 4 , —CF 2 CH 2 —, —CH 2 CF 2 —, —CFHCFH—, —CFHCH 2 —, —CH 2 CFH—, —CF 2 CFH—, —CFHCF 2 —, —CH═CH—, —CF═CH—, —CH═CF—, —CF═CF—, —C≡C— or a single bond,
m denotes 0, 1, 2 or 3, and
n denotes 0, 1, 2 or 3;
and
b) one or more compounds selected from the group of compounds of formulae IIA, IIB, IIC and IID

in which
R 2A , R 2B , R 2C and R 2D identically or differently, denote H, straight chain alkyl or alkoxy having 1 to 15 C atoms, straight chain alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl or alkoxy or alkenyl or alkenyloxy having 3 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

 —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, by —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen,
L 1 and L 2 , each, independently of one another, denote F, Cl, CF 3 or CHF 2 ,
Y denotes H, F, Cl, CF 3 , CHF 2 or CH 3 ,
Z 2 , Z 2 B and Z 2 D each, independently of one another, denote 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— or —CH═CHCH 2 O—,
(O) denotes O or a single bond,
p denotes 0, 1 or 2,
q denotes 0 or 1, and
v denotes an integer from 1 to 6;

wherein the medium has negative dielectric anisotropy.

2. The liquid crystal medium according to claim 1 , wherein the total amount of the one or more compounds selected from the group of compounds of formulae IIA, IIB, IIC and IID is in the range of 9% to 70%.

3. The liquid crystal medium according to claim 1 , wherein the one or more compounds of formula I are selected from the group of compounds of formulae I-1 to I-6

in which R 1 and R 2 have the meanings given for formula I, L is halogen, CN, CH 3 , CHF 2 , CH 2 F, CF 3 , OCH 3 , OCHF 2 or OCF 3 , and r, s and t independently are 0, 1, 2, 3, or 4.

4. The liquid crystal medium according to claim 3 , wherein the group

in the formulae I-1 to I-6 denotes

5. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of formula III

in which
R 31 and R 32 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms, where one or more CH 2 groups in these radicals may each be replaced, independently of one another, by

 —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—, by —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen,
A 31 on each occurrence, independently of one another, denotes
a) 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH 2 groups may be replaced by —O— or —S—,
b) a 1,4-phenylene radical, in which one or two CH groups may be replaced by N, or
c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl,
where the radicals a), b) and c) may be mono- or polysubstituted by halogen atoms,

n denotes 0, 1 or 2,
Z 31 on each occurrence independently of one another denotes —CO—O—, —O—CO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CH 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—CH 2 O—, —C 2 F 4 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF═CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C≡C— or a single bond,
L 31 and L 32 each, independently of one another, denote F, Cl, CF 3 or CHF 2 , and
W denotes O or S.

6. The liquid crystal medium according to claim 5 , wherein W in formula III denotes S.

7. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of formula IV

in which
R 41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, and
R 42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, or an unsubstituted alkenyl radical having 2 to 7 C atoms.

8. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds selected from the group consisting of compounds of formulae IV-3-1 and IV-3-2:

in which alkyl denotes n-alkyl having 1 to 7 C-atoms.

9. The liquid crystal medium according to claim 1 , wherein the medium further comprises one or more compounds of the formula V

in which
R 51 and R 52 denote, each independently, alkyl having 1 to 7 C atoms, alkoxy having 1 to 7 C atoms, or alkoxyalkyl, alkenyl or alkenyloxy having 2 to 7 C atoms,

 identically or differently, denote

Z 51 and Z

Assignees

• Merck Patent Gmbh

Inventors

• Huang Chi-Shun
• Laut Sven Christian
• Lee Hee-Kyu
• Yang Minghui
• Hirschmann Harald
• Chou Kuang-Ting
• Hung Shih-Chieh
• Hahn Alexander
• Wucher Philipp

Classifications

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title

• C09K19/542

  Macromolecular compounds · CPC title

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C09K2019/0448

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

• C09K2019/123

  Ph-Ph-Ph · CPC title