Liquid-crystalline media, components for high-frequency technology, and mesogenic compounds

Patent metadata

Field	Value
Publication number	US-9523037-B2
Application number	US-201514850057-A
Country	US
Kind code	B2
Filing date	Sep 10, 2015
Priority date	Jan 21, 2011
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

The present invention relates to a liquid-crystal medium which comprises a component A which consists of one or more compounds of the formula I

in which the parameters have the respective meanings given in the claims or in the text, and to the corresponding, novel mesogenic compounds and to the preparation thereof. The present invention likewise relates to the use of these liquid-crystal media, in particular in components for high-frequency technology, and to components of this type which contain media according to the invention, and to the production and use of these components. The components according to the invention are suitable, in particular, as phase shifters in the microwave and millimeter wave region, for microwave and millimeter wave array antennae and very particularly for so-called tuneable “reflectarrays”.

First claim

The invention claimed is:

1. A liquid-crystal medium which comprises a component A which comprises one or more compounds of the formula I-1 or I-2,

in which
L 1 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms or cycloalkenyl having 4 to 6 C atoms,
X 1 denotes alkyl having 1 to 3 C atoms or halogen, and
R 11 and R 12 , independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, unfluorinated alkenyl having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms.

2. A liquid-crystal medium according to claim 1 , wherein component A further comprises one or more compounds selected from the group of the compounds of the formulae I-3 to I-4:

in which the parameters have the meanings given in claim 1 and
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.

3. A liquid-crystal medium according to claim 1 , wherein component A comprises one or more compounds of the formula I-2.

4. A liquid-crystal medium according to claim 1 , wherein component A comprises one or more compounds of the formula I-1.

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

6. A liquid-crystal medium according to claim 1 , wherein, besides a component A, it additionally comprises one or more components selected from the group of the following components, components B to E:
a strongly dielectrically positive component B, which has a dielectric anisotropy of 10 or more,
a strongly dielectrically negative component C, which has a dielectric anisotropy having a value of 5 or more,
a component D, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and consists of compounds having seven or more five- or six-membered rings, and
a component E, which has a dielectric anisotropy in the range from more than −5.0 to less than 10.0 and consists of compounds having up to six five- or six-membered rings.

7. A liquid-crystal medium according to claim 6 , which comprises a component B.

8. A liquid-crystal medium according to claim 6 , which comprises a component C.

9. A liquid-crystal medium according to claim 6 , which comprises a component D.

10. A liquid-crystal medium according to claim 6 , which comprises a component E.

11. A liquid-crystal medium according to claim 1 , which further comprises one or more compounds of the 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

12. A process for the preparation of a liquid-crystal medium according to claim 1 , which comprises mixing one or more compounds of the formula I-1 or I-2, with one or more further compounds and/or with one or more additives.

13. A liquid-crystal medium according to claim 1 , wherein component A comprises one or more compounds of the formula I-1, in which L 1 denotes cycloalkyl having 3 to 6 C atoms.

14. A liquid-crystal medium according to claim 1 , wherein component A comprises one or more compounds of the formula I-1, in which L 1 denotes cyclopropyl, cyclobutyl, cyclohexyl, cyclopent-1-enyl or cyclohex-1-enyl.

15. A liquid-crystal medium according to claim 1 , wherein R 11 and R 12 , independently of one another, denote unfluorinated alkyl having 1 to 7 C atoms.

16. A liquid-crystal medium according to claim 1 wherein R 11 and R 12 , independently of one another, denote unfluorinated alkyl having 2 to 7 C atoms.

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

18. A microwave antenna array, comprising one or more components according to claim 17 .

19. A process for tuning a microwave antenna array, which comprises electrically addressing a component in a microwave antenna array according to claim 18 .

20. A compound selected from the group of the compounds of the formulae I-1 and I-2:

in which
L 1 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms or cycloalkenyl having 4 to 6 C atoms,
X 1 denotes alkyl having 1 to 3 C atoms or halogen, and
R 11 and R 12 , independently of one another, denote unfluorinated alkyl having 1 to 15 C atoms, unfluorinated alkenyl having 2 to 15 C atoms, or cycloalkyl, alkylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkylcycloalkylalkyl or alkylcycloalkenylalkyl, each having up to 15 C atoms.

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C09K2019/188

  Ph-C≡C-Ph-C≡C-Ph · CPC title

• C09K19/10

  containing at least two benzene rings · CPC title

• C09K19/3059

  in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds · CPC title

• C09K19/18 Primary

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

• C09K19/30

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