Bimesogenic compounds and mesogenic media

Patent metadata

Field	Value
Publication number	US-9758727-B2
Application number	US-201415107213-A
Country	US
Kind code	B2
Filing date	Nov 27, 2014
Priority date	Dec 23, 2013
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

The invention relates to bimesogenic compounds of formula I

wherein R 11 , R 12 , MG 11 , MG 12 , X 11 , X 12 and Sp 1 have the meaning given in claim 1 , to the use of bimesogenic compounds of formula I in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

First claim

The invention claimed is:

1. A bimesogenic compound of formula I

wherein
R 11 and R 12 are each independently H, F, Cl, CN, NCS or a straight-chain or branched alkyl group with 1 to 25 C atoms which may be unsubstituted, mono- or polysubstituted by halogen or CN, it being also possible for one or more non-adjacent CH 2 groups to be replaced, in each occurrence independently from one another, by —O—, —S—,
—NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —O—CO—O—, —S—CO—, —CO—S—, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,

MG 11 and MG 12 are each independently a mesogenic group and
at least one of
MG 11 and MG 12 comprises one, two or more 5-atomic rings,
Sp 1 is a spacer group of 1, 3 or 5 to 40 C atoms, wherein one or more non-adjacent groups may also be replaced by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-,
—CH(CN)—, —CH═CH— or —C≡C—, however in such a way that no two O-atoms are adjacent to one another, now two —CH═CH— groups are adjacent to each other and no two groups selected from —O—CO—, —S—CO—, —O—COO—,
—CO—S—, —CO—O— and —CH═CH— are adjacent to each other,

X 11 is —CO—S—, —S—CO—, —CS—S—,
—S—CS—, —CS—O—, —O—CS—, —S—CO—S—, —S—CS—S— or —S—,

X 12 independently from X 11 has one of the meanings given for X 11 or is —CO—O—, —O—CO—,
—CH═CH—, —C≡C—, —O— or a single bond,

however under the condition that in —X 11 -Sp 1 -X 12 — no two O atoms are adjacent to one another, no two —CH═CH— groups are adjacent to each other and no two groups —O—CO—, —S—CO—,
—O—COO—, —CO—S—, —CO—O— or —CH═CH— are adjacent to each other.

2. A bimesogenic compound according to claim 1 , wherein
at least one of
MG 11 and MG 12 is one, two or more 5-atomic rings, and one or more 6-atomic rings, and at least two of these are optionally linked by a 2 atom moiety.

3. A bimesogenic compound according to claim 1 , wherein both MG 11 and MG 12 are one, two or more 5-atomic rings.

4. A bimesogenic compound according to claim 1 , wherein R 12 is OCF 3 , CF 3 , F, Cl or CN.

5. A bimesogenic compound according to claim 1 , wherein Sp 1 is —(CH 2 ) o — and o is 1, 3 or an integer from 5 to 15.

6. A liquid-crystalline medium, comprising one or more bimesogenic compounds according to claim 1 .

7. A liquid-crystalline medium according to claim 6 , additionally comprising one or more compounds of formulae III
R 31 -MG 31 -X 31 -Sp 3 -X 32 -MG 32 -R 32   III

wherein
R 31 and R 32 are each independently H, F, Cl, CN, NCS or a straight-chain or branched alkyl group with 1 to 25 C atoms which may be unsubstituted, mono- or polysubstituted by halogen or CN, it being also possible for one or more non-adjacent CH 2 groups to be replaced, in each case independently from one another, by —O—, —S—, —NH—,
—N(CH 3 )—, —CO—, —COO—, —COO—, —O—CO—O—, —S—CO—,
—CO—S—, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another,

MG 31 and MG 32 are each independently a mesogenic group,
Sp 3 is a spacer group of 5 to 40 C atoms, wherein one or more non-adjacent CH 2 groups may also be replaced by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —O—CO—,
—S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-,
—CH(CN)—, —CH═CH— or —C≡C—, and

X 31 and X 32 are each independently —O—, —S—, —CO—, —COO—, —OCO—,
—O—CO—O—, —CO—NH—, —NH—CO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—,
—SCH 2 —, —CH 2 S—, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—,
—C≡C— or a single bond, and

with the condition that compounds of formula I are excluded.

8. A liquid crystal device comprising a liquid crystalline medium comprising two or more components, one or more of which is a bimesogenic compound of formula I according to claim 1 .

9. The liquid crystal device according to claim 8 , that is a flexoelectric device.

10. The bimesogenic compound according to claim 1 , wherein R 11 and R 12 are each independently F, Cl, CN, OCF 3 or CF 3 .

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Parri Owain Llyr
• Tuffin Rachel
• Saxton Patricia Eileen

Classifications

• C09K19/3494 Primary

  the heterocyclic ring containing sulfur and oxygen atoms · CPC title

• C09K19/3477

  the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom · CPC title

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C09K2019/0444

  characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group · CPC title

• C09K19/3405

  the heterocyclic ring being a five-membered ring · CPC title