Mesogenic compounds, liquid crystal media and components for high frequency technology

Patent metadata

Field	Value
Publication number	US-10442990-B2
Application number	US-201214006106-A
Country	US
Kind code	B2
Filing date	Feb 27, 2012
Priority date	Mar 24, 2011
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

A liquid-crystal medium having a component A which is one or more compounds of the formula IA

and corresponding, novel mesogenic compounds and the preparation thereof. These liquid-crystal media, are used in components for high-frequency technology, and to components of this type which contain the media. The components are suitable, in particular, for phase shifters in the microwave and millimeter wave region, for microwave and millimeter wave array antennae and very particularly for so-called tunable “reflectarrays”.

First claim

The invention claimed is:

1. A liquid-crystal medium, comprising a component A which comprises one or more compounds of formulae IA-1, IA-2, or IA-1 and IA-2,

in which
L 1 denotes hydrogen, alkyl having 1 to 3 C atoms, or halogen,
one of
Y 11 and Y 12 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, cycloalkenyl having 4 to 6 C atoms or halogen,
and the other denotes H, alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, cycloalkenyl having 4 to 6 C atoms or halogen,
R 11 and R 12 , independently of one another, denote unfluorinated alkyl or un-fluorinated alkoxy, each having 1 to 15 C atoms, unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcyclo-alkenylalkyl, each having up to 15 C atoms, and
R 13 denotes alkyl having 2 to 6 C atoms, unfluorinated alkenyl having 2 to 6 C atoms, unfluorinated cycloalkyl having 3 to 5 C atoms or unfluorinated cycloalkenyl having 4 to 6 C atoms,
and which further comprises one or more compounds of formula IB-2 and/or IB-4

R 11 R 12 , R 13 and R 14 , independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms, and alternatively one of R 13' and R 14 or both also denote H.

2. The liquid-crystal medium according to claim 1 , wherein component A further comprises one or more compounds of the formulae IB-1

in which in IB-1, L 1 is C 1-6 , alkyl, C 3-6 -cycloalkyl, C 4-6 cycloalklenyl or halogen, and X 1 is H, C 1-3 -alkyl or halogen.

3. The liquid-crystal medium according to claim 2 , wherein component A comprises one or more compounds of the formula IB-1, in which X 1 denotes H.

4. The liquid-crystal medium according to claim 2 , wherein component A comprises one or more compounds of the formula IB-1, in which X 1 denotes F.

5. The liquid-crystal medium according to claim 1 , additionally comprising one or more components B to E:
a strongly dielectrically positive component, component B, which has a dielectric anisotropy of 10 or more,
a strongly dielectrically negative component, component C, which has a dielectric anisotropy having a value of −5 or less,
a component, component D, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and is compounds having seven or more five- or six-membered rings, and
a component, component E, which likewise has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and is compounds having up to six five- or six-membered rings.

6. The liquid-crystal medium according to claim 5 , comprising a component B.

7. The liquid-crystal medium according to claim 5 , comprising component C.

8. The liquid-crystal medium according to claim 5 , comprising component D.

9. The liquid-crystal medium according to claim 1 , comprising one or more compounds of formula VI

in which
L 61 denotes R 61 and, in the case where Z 61 and/or Z 62 denote trans-CH═CH— or trans-CF═CF—, alternatively also denotes X 61 ,
L 62 denotes R 62 and, in the case where Z 61 and/or Z 62 denote trans-CH═CH— or trans-CF=CF—, alternatively also denotes X 62 ,
R 61 and R 62 , independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms,
X 61 and X 62 , independently of one another, denote F or Cl, —CN, —NCS, —SF 5 , fluorinated alkyl or alkoxy having 1 to 7 C atoms or fluorinated alkenyl, alkenyloxy or alkoxyalkyl having 2 to 7 C atoms, or —NCS,
one of
Z 61 and Z 62 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other, independently thereof, denotes trans-CH═CH—, trans-CF═CF—or a single bond, and

independently of one another, denote

10. A process for the preparation of a liquid-crystal medium according to claim 1 , comprising mixing one or more compounds of the formula IA-1 and/or IA-2, and IB-2 and/or IB-4, as indicated in claim 1 , with one or more further compounds and/or with one or more additives.

11. A component for high-frequency technology, containing a liquid-crystal medium according to claim 1 .

12. A microwave antenna array, comprising one or more components according to claim 11 .

13. A process for tuning a microwave antenna array, comprising electrically addressing a component thereof according to claim 11 .

14. A liquid-crystal medium according to claim 1 , wherein R 13 is ethyl.

15. A liquid-crystal medium according to claim 1 , comprising one or more compounds of the formula IA-2b, IA-2c or IA-2b and IA-2c,

16. A process for the preparation of a compound of the formula IA,

in which
L 1 denotes hydrogen, alkyl having 1 to 3 C atoms, or halogen,
one of
Y 11 and Y 12 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, cycloalkenyl having 4 to 6 C atoms or halogen,
and the other denotes H, alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, cycloalkenyl having 4 to 6 C atoms or halogen,
R 11 and R 12 , independently of one another, denote unfluorinated alkyl or un-fluorinated alkoxy, each having 1 to 15 C atoms, unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcyclo-alkenylalkyl, each having up to 15 C atoms, and R 12 denotes alkyl having 2 to 6 atoms, unfluorinated alkenyl having 2 to 6 atoms, unfluorinated cycloalkyl having 3 to 5 C atoms or unfluorinated cycloalkenyl having 4 to 6 C atoms, and
R 13 is alkyl having 2 to 6 C atoms, unfluorinated alkenyl having 2 to 6 C atoms, unfluorinated cycloalkyl having 3 to 5 C atoms or unfluorinated cycloalkenyl having 4 to 6 C atoms,
comprising

17. The process according to claim 16 , wherein the compound of formula IA has formula IA-1

18. The process according to claim 16 , wherein the compound of formula IA has formula

Assignees

• Jasper Christian
• Montenegro Elvira
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka
• Merck Patent Gmbh

Inventors

• Jasper Christian
• Montenegro Elvira
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka

Classifications

• C09K19/18 Primary

  the chain containing carbon-to-carbon triple bonds, e.g. tolans · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2019/188

  Ph-C≡C-Ph-C≡C-Ph · CPC title

• C09K2019/183

  Ph-Ph-C≡C-Ph · CPC title

• C09K2219/11

  used in the High Frequency technical field · CPC title