Liquid-crystalline medium and high-frequency components comprising same

Patent metadata

Field	Value
Publication number	US-9593279-B2
Application number	US-201514820803-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Aug 8, 2014
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The present invention relates to liquid-crystalline media comprising
one or more compounds selected from the group of compounds of formulae I, II and III,

in which the parameters R 1 -R 3 , Z 21 , Z 31 , Z 32 and rings A 11 , A 12 , A 13 , A 21 , A 22 , A 31 , and A 32 are as defined herein, and to components comprising these media for high-frequency technology, in particular phase shifters and microwave array antennas.

First claim

The invention claimed is:

1. A liquid-crystal medium comprising:
one or more compounds selected from formula III-1

in which
R 3 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, and

 independently of one another, denote

alternatively independently denotes e

and
optionally one or more compounds selected from formulae I and II

in which
R 1 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,
n denotes 0 or 1, and

 independently of one another, denote

 alternatively denotes

in which
R 2 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,
Z 21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and

independently of one another, denote

and
optionally one or more polymerizable compounds.

2. A liquid-crystal medium according to claim 1 , wherein said medium contains one or more said polymerizable compounds, and said polymerizable compounds are of formula P
P a -(Sp a ) s1 -(A 1 -Z 1 ) n1 -A 2 -Q-A 3 -(Z 4 -A 4 ) n2 -(Sp b ) s2 -P b   P

wherein the individual radicals have the following meanings:
P a , P b each, independently of one another, are a polymerizable group,
Sp a , Sp b each, independently of one another, denotes a spacer group,
s1, s2 each, independently of one another, denotes 0 or 1,
n1, n2 each, independently of one another, denotes 0 or 1,
Q denotes a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CO)O—, —O(CO)—, —(CH 2 ) 4 —, —CH 2 —CH 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —CH═CF—, —C≡C—, —O—, —CH 2 —, —(CH 2 ) 3 —, or —CF 2 —,
Z 1 , Z 4 each denotes a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CO)O—, —O(CO)—, —(CH 2 ) 4 —, —CH 2 —CH 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —CH═CF—, —C≡C—, —O—, —CH 2 —, —(CH 2 ) 3 —, or —CF 2 —, where Z 1 and Q or Z 4 and Q do not simultaneously denote a group selected from —CF 2 O— and —OCF 2 —,
A 1 , A 2 , A 3 , A 4
each, independently of one another, denotes a diradical group selected from the following groups:
a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 1,4′-bicyclohexylene, in which, in addition, one or more non-adjacent CH 2 groups are each optionally replaced by —O— or —S— and in which, in addition, one or more H atoms each optionally replaced by F,
b) the group consisting of 1,4-phenylene and 1,3-phenylene, in which, in addition, one or two CH groups each optionally replaced by N and in which, in addition, one or more H atoms each optionally replaced by L,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which is unsubstituted or mono- or polysubstituted by L, and
d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, each be replaced by a heteroatom,
where, in addition, one or more H atoms in these radicals are each optionally replaced by L, and/or one or more double bonds are each optionally replaced by single bonds, and/or one or more CH groups are each optionally replaced by N, and
A 3 , alternatively, is a single bond,

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
R 03 , R 04 each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, in which, in addition, one or more H atoms are each optionally replaced by F,
M denotes —O—, —S—, —CH 2 —, —CHY 1 — or —CY 1 Y 2 —, and
Y 1 and Y 2 each, independently of one another, have one of the meanings indicated above for R 03 , or denote Cl or CN, and one of the groups Y 1 and Y 2 alternatively denotes —OCF 3 .

3. A liquid-crystal medium according to claim 2 , wherein n1 and n2 are each 0.

4. A liquid-crystal medium according to claim 2 , wherein Q is —CF 2 O—.

5. A liquid-crystal medium according to claim 1 , wherein said medium contains one or more compounds of formula I.

6. A liquid-crystal medium according to claim 1 , wherein said medium contains one or more compounds of formula II.

7. A liquid-crystal medium according to claim 1 , wherein said medium further contains one or more compounds selected from the compounds of formulae I-1, I-2 II-1 to II-3 and III-2 to III-6

in which
R 1 , R 2 , R 3 , A 11 , A 12 , A 13 , A 21 , A 22 , A 31 , A 32 , and A 33 have the meanings given in claim 1 , and
one of Z 31 and Z 32 denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other one, independently thereof, denotes trans-CH═CH—, trans-CF═CF— or a single bond.

8. A liquid-crystal medium according to claim 1 , wherein said medium contains a polymerizable compound and optionally additionally comprises a polymerization initiator.

9. A method of stabilizing of a liquid-crystal medium according to claim 1 , wherein said medium contains said one or more polymerizable compounds, said method comprising polymerizing said one or more polymerizable compounds.

10. A composite system obtained from a liquid crystal medium according to claim 1 , wherein said medium contains said one or more polymerizable compounds, and said composite system is obtained by polymerizing one or more polymerizable compounds.

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

12. The component according to claim 11 , wherein said component is operable in the microwave range.

13. The component according to claim 11 , wherein said component is a phase shifter or a LC based antenna element operable in the microwave region.

14. A process for the preparation of a liquid

Assignees

• Merck Patent Gmbh

Inventors

• Wittek Michael
• Klass Dagmar
• Manabe Atsutaka
• Jasper Christian
• Reiffenrath Volker
• Brocke Constanze
• Pauluth Detlef

Classifications

• C09K19/16

  the chain containing carbon-to-carbon double bonds, e.g. stilbenes · CPC title

• C09K2019/181

  Ph-C≡C-Ph · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/0459

  the linking chain being a -CF=CF- chain, e.g. 1,2-difluoroethen-1,2-diyl · CPC title