Mesogenic compounds, liquid-crystalline media and components for high-frequency technology

Patent metadata

Field	Value
Publication number	US-9765259-B2
Application number	US-201214006725-A
Country	US
Kind code	B2
Filing date	Mar 7, 2012
Priority date	Mar 24, 2011
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

A liquid-crystal medium containing a component A of one or more compounds of formula X

the preparation thereof, and the use of these liquid-crystal media, in particular in components for high-frequency technology, and components of this type which contain the media, and the production and use of these components. The components are suitable for phase shifters in the microwave and millimeter wave region, for microwave and millimeter wave array antennae and for tuneable reflectarrays.

First claim

The invention claimed is:

1. A liquid-crystal medium, comprising
a component A which comprises one or more compounds of formula X,

in which
L 101 denotes H or F,
X 101 denotes NCS,
Y 101 denotes F,
Y 102 denotes H, F or Cl,
R 101 denotes 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
R 102 denotes unfluorinated alkyl having 2 to 5 C atoms or unfluorinated cycloalkyl or cycloalkenyl having 3 to 7 C atoms; and
a component F which comprises one or more compounds of formula I-2 and/or of formula I-3 and/or of formula I-4

in which
R 11 to R 14 each, independently of one another, denotes 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 comprises one or more compounds of formula X-1

in which X 101 , Y 101 , Y 102 , R 101 and R 102 have the meanings given under formula X.

3. A liquid-crystal medium, comprising
a component A which comprises one or more compounds of formula X,

in which
L 101 denotes H or F,
X 101 denotes NCS,
Y 101 denotes F,
Y 102 denotes H, F or Cl,
R 101 denotes 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
R 102 denotes unfluorinated alkyl having 2 to 5 C atoms or unfluorinated cycloalkyl or cycloalkenyl having 3 to 7 C atoms; and
a component F which comprises one or more compounds of formula I-2 and/or of formula I-3 and/or of formula I-4

in which
R 11 to R 14 each, independently of one another, denotes 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; and
one or more compounds of formula I-1

in which
L 11 denotes alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 6 C atoms, cycloalkenyl having 4 to 6 C atoms or halogen,
X 11 denotes H, alkyl having 1 to 3 C atoms or halogen, and
R 11 and R 12 have the meanings given above.

4. The liquid-crystal medium according to claim 1 , wherein component F comprises one or more compounds of formula I-2.

5. The liquid-crystal medium according to claim 3 , wherein component F comprises one or more compounds of formula I-1, in which X 11 denotes H.

6. The liquid-crystal medium according to claim 3 , wherein component F comprises one or more compounds of formula I-1, in which X 11 denotes F.

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

8. The liquid-crystal medium according to claim 7 , which comprises a component B.

9. The liquid-crystal medium according to claim 7 , which comprises a component D.

10. The 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 each, independently of one another, denotes 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 each, independently of one another, denotes 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 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

 to

 each , independently of one another, denotes

11. A process for preparing a liquid-crystal medium according to claim 1 , comprising mixing together one or more compounds of formula X with one or more compounds of formula I-2 and/or of formula I-3 and/or of formula I-4, and optionally with one or more further compounds and/or with one or more additives.

12. A component for high-frequency technology, which contains a liquid-crystal medium according to claim 1 .

13. A microwave antenna array, which comprises one or more components according to claim 12 .

14. A method for tuning a microwave antenna array according to claim 13 , comprising electrically addressing said component for high-frequency technology.

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

Assignees

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

Inventors

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

Classifications

• C09K19/3059 Primary

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

• C09K2219/11

  used in the High Frequency technical field · CPC title

• C09K19/30

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

• C09K19/18 Primary

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

• C09K2019/188

  Ph-C≡C-Ph-C≡C-Ph · CPC title