Compounds having a C—C triple bond

Patent metadata

Field	Value
Publication number	US-9777217-B2
Application number	US-201214005839-A
Country	US
Kind code	B2
Filing date	Feb 27, 2012
Priority date	Mar 24, 2011
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

Compounds containing at least one C—C triple bond within a chain of at least 3 ring systems which have positive dielectric anisotropy, the use thereof for high-frequency components, liquid-crystalline media containing these compounds, and high-frequency components, in particular antennae, especially for the gigahertz region, containing these media. The liquid-crystalline media serve, for example, for the phase shifting of microwaves for tuneable phased-array antennae.

First claim

The invention claimed is:

1. A compound of formula I

in which
H/F means H or F,
A 1-5 independently of one another, denote
a) 1,4-phenylene, in which one or more CH groups are optionally replaced by N, or
b) a radical of one of the following formulae

 wherein in a) and b), optionally one or more H atoms are independently replaced by L, which L in a) and b) each, independently of one another, denotes Br, Cl, F, CN, —NCS, —SCN, SF 5 , C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 3 -C 6 cycloalkyl or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group,
and wherein one of the rings A 3 and A 4 denotes

Y denotes S or O,
R 1 denotes a halogenated or unsubstituted alkyl radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, by —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)—, —O— or —S— in such a way that O or S atoms are not linked directly to one another, or denotes F, Cl, Br, CN, SCN, NCS or SF 5 ,
X denotes F, Cl, Br, CN, SCN, NCS, SF 5 or a halogenated alkyl radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, by —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)—, —O— or —S— in such a way that O or S atoms are not linked directly to one another,
Z 1 , Z 2 , Z 4 , Z 5 all denote a single bond, and
m, n, p, q independently denote 0 or 1, where m+n+p+q is 1, 2, 3 or 4.

2. A compound according to claim 1 , wherein A 3 denotes 1,4-phenylene, in which one or more CH groups are optionally replaced by N.

3. A compound according to claim 1 , wherein m and n are 0.

4. A compound according to claim 1 , wherein A 1 , A 2 , A 5 and one of A 3 or A 4 , if present, each denote an optionally substituted 1,4-phenylene ring.

5. A compound according to claim 1 , wherein m+n+p+q is 1.

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

7. A liquid-crystal medium according to claim 6 , further comprising one or more compounds of formula II:

in which:
L 11 denotes R 11 or X 11 ,
L 12 denotes R 12 or X 12 ,
R 11 and R 12 independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy having 1 to 17 C atoms, or unfluorinated alkenyl, unfluorinated alkynyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms,
X 11 and X 12 independently of one another, denote F, Cl, Br, CN, NCS, SCN, SF 5 , or fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, or fluorinated alkenyl, fluorinated alkenyloxy or fluorinated alkoxyalkyl having 2 to 7 C atoms,
p, q independently denote 0 or 1,
Z 11 to Z 13 independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, and

 independently of one another, denote

L′ independently denotes branched or unbranched alkyl, alkenyl or alkynyl having 1 to 12 C atoms, in which, independently of one another, one or more CH 2 groups are optionally replaced by O, or denotes C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, fluorinated alkyl or alkenyl, fluorinated alkoxy or alkenyloxy, F, Cl, Br, CN, NCS, SCN or SF 5 .

8. A liquid-crystal medium according to claim 6 , wherein the concentration of the compounds of formula I in total is 5% to 95%.

9. A process for preparing a liquid-crystal medium according to claim 6 , comprising mixing together one or more compounds of formula I with one or more further compounds and optionally with one or more additives.

10. A component for high-frequency technology, which contains a liquid-crystal medium according to claim 6 .

11. A component according to claim 10 , which comprises one or more functionally connected phase shifters.

12. A phased array antenna, which comprises one or more components according to claim 10 .

13. A compound according to claim 1 , wherein L each, independently of one another, denotes methyl, ethyl or straight or branched propyl.

14. A compound according to claim 1 , wherein L each, independently of one another, denotes cyclopropyl.

15. A compound according to claim 1 , wherein one of the rings A 3 and A 4 denotes

16. A compound according to claim 1 , wherein one of the rings A 3 and A 4 denotes

17. A compound according to claim 1 , wherein one of the rings A 3 and A 4 denotes

18. A compound according to claim 1 , wherein
R 1 denotes an unsubstituted alkyl radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, by —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)—, —O— or —S— in such a way that O or S atoms are not linked directly to one another, or denotes F, Cl, Br, CN, SCN, NCS or SF 5 .

19. A compound according to claim 1 , wherein
X denotes F, Cl, Br, SCN, NCS, SF 5 or a halogenated alkyl radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, by —CC—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)—, —O— or —S— in such a way that O or S atoms are not linked directly to one another.

20. A compound according to claim 1 , wherein m+n is 0 or 1.

Assignees

• Jasper Christian
• Brocke Constanze
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka
• Merck Patent Gmbh

Inventors

• Jasper Christian
• Brocke Constanze
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka

Classifications

• C07C13/47

  with a bicyclo ring system containing ten carbon atoms · CPC title

• C09K19/08

  containing at least two non-condensed rings · CPC title

• C09K19/18 Primary

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

• C09K2019/183

  Ph-Ph-C≡C-Ph · CPC title

• C09K19/3059 Primary

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