Mesogenic compound, liquid-crystal medium and liquid crystal display

Patent metadata

Field	Value
Publication number	US-9809749-B2
Application number	US-201414785500-A
Country	US
Kind code	B2
Filing date	Mar 21, 2014
Priority date	Apr 19, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

Mesogenic compounds of formula I-Z

are suitable for use in mesogenic media. Such mesogenic media can exhibit a blue phase and comprise component A, consisting of one or more compounds of formula I-Z, and, optionally a component B, consisting of one or more compounds selected from the group of compounds of formulae

I-M and I-U,

wherein the parameters are as defined herein. The media can also be stabilized by a polymer. The media can be used in electro-optical light modulation elements and displays.

First claim

The invention claimed is:

1. A mesogenic compound of formula I-Z

wherein
R 1 is n-alkyl or n-alkoxy with 1 to 9 C-atoms, or alkenyl, alkenyloxy or alkoxyalkyl with 2 to 9 C-atoms,
L 1 is H or F, and
X 1 is F or CF 3 .

2. A mesogenic medium exhibiting a blue phase, comprising a component A, consisting of one or more compounds of formula I-Z

wherein
R 1 is n-alkyl or n-alkoxy with 1 to 9 C-atoms, or alkenyl, alkenyloxy or alkoxyalkyl with 2 to 9 C-atoms,
L 1 is H or F, and
X 1 is F or CF 3 .

3. The mesogenic medium according to claim 2 , further comprising one or more chiral dopants.

4. The mesogenic medium according to claim 2 , further comprising a second component, component B, consisting of one or more compounds selected from formulae I-M and I-U

wherein
R 1 is alkyl with 1 to 9 C-atoms, which is straight chain or branched, unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
Y 01 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H,
R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12 C-atoms, and
L 1 and X 1 have the respective meanings given in claim 2 .

5. The mesogenic medium according to claim 2 , further comprising one or more compounds selected from formulae I-A, I-E, I-N and I-T

wherein
R 0 is alkyl with 1 to 9 C-atoms, which is straight chain or branched, unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
R 1 is alkyl with 1 to 9 C-atoms, which is straight chain or branched, unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
Y 01 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H,
R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12 C-atoms, and
L 01 to L 03 , L 1 , L 11 and L 12 are independently of one another H or F.

6. The mesogenic medium according to claim 2 , further comprising one or more compounds of formula II

wherein
L 21 to L 23 are, independently of each other, H or F,
R 2 is alkyl, which is straight chain or branched, is unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
Y 01 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H, and
R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12 C-atoms.

7. The mesogenic according to claim 2 , further comprising one or more compounds of formula III

wherein
R 3 is alkyl with 1 to 9 C-atoms, which is straight chain or branched, unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
Y 01 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H, and
R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12 C-atoms.

8. The mesogenic medium according to claim 2 , further comprising one or more compounds selected from formulae IV and V

wherein
R 4 and R 5 are, independently of each other, alkyl, which is straight chain or branched, having 1 to 20 C-atoms, is unsubstituted, mono- or poly-substituted by F, Cl or CN, and in which one or more CH 2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another,
L 5 is H or F,

and
n and m are each, independently of one another, 0 or 1.

9. The mesogenic medium according to at least claim 2 , further comprising a polymerisable component, which comprises one or more polymerisable compounds.

10. The mesogenic medium according to claim 2 , further comprising one or more compounds of formula M1

wherein the parameters have the following meanings:
P 1 and P 2 each, independently of one another, a polymerisable group,
Sp 1 and Sp 2 each, independently of one another, a single bond or a spacer group, and, wherein alternatively also one or more of P 1 -Sp 1 - and P 2 -Sp 2 - may be R aa , provided that at least one of P 1 -Sp 1 - and P 2 -Sp 2 - present in the compound is not R aa ,
R aa H, F, Cl, CN or linear or branched alkyl having 1 to 25 C-atoms, wherein one or more non-adjacent —CH 2 — groups, independently of each another, may be replaced 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 neither O- nor S-atoms are directly linked to one another, and wherein also one or more H-atoms may be replaced by F, Cl, CN or P 1 -Sp 1 -,

R 0 , R 00 each, at each occurrence independently of one another, H or alkyl having 1 to 12 C-atoms,
R y and R z each, independently of one another, H, F, CH 3 or CF 3 ,
L at each occurrence independently of one another, F, Cl, CN, SCN, SF 5 or linear or branched, optionally mono- or poly-fluorinated, alkyl, alkoxy, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C-atoms, and
r 0, 1, 2, 3 or 4.

11. The mesogenic medium according to claim 2 , further comprising one or more compounds of formula M2

wherein the parameters have the following meanings:
P 1 and P 2 each, independ

Assignees

• Merck Patent Gmbh

Inventors

• Wittek Michael
• Bremer Matthias
• Taugerbeck Andreas

Classifications

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C09K19/3458 Primary

  Uncondensed pyrimidines · CPC title

• C09K2019/3083

  Cy-Ph-COO-Ph · CPC title

• C09K19/3469

  Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*- · CPC title

• C09K19/062

  containing one non-condensed benzene ring · CPC title