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

Patent metadata

Field	Value
Publication number	US-9752077-B2
Application number	US-201113980058-A
Country	US
Kind code	B2
Filing date	Dec 22, 2011
Priority date	Jan 21, 2011
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

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 compound selected from the group of the compounds of the formulae I-3 and I-4,

in which
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, 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 also denotes H.

2. A liquid crystal mixture comprising a compound selected from the group of the compounds of the formulae I-3 and I-4 of claim 1 .

3. A liquid-crystal mixture according to claim 2 , which comprises one or more compounds of the formula I-3.

4. A liquid-crystal mixture according to claim 2 , which comprises one or more compounds of the formula I-4.

5. A liquid-crystal mixture according to claim 2 , which further 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 H, 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.

6. A liquid-crystal mixture according to claim 2 , which additionally comprises one or more components selected from the group of the following 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 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 mixture according to claim 6 , which comprises a component B.

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

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

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

11. A liquid-crystal mixture according to claim 2 , 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

to

independently of one another, denote

12. A component for high-frequency technology, comprising a liquid-crystal mixture according to claim 2 .

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

14. A compound of claim 1 , which is a compound of formula I-3.

15. A compound of claim 1 , which is a compound of formula I-4.

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

  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

• C09K2019/3096

  Cyclobutane rings · CPC title

• C09K19/18 Primary

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

• C09K19/322 Primary

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