Liquid-crystalline medium and high-frequency components comprising same

Patent metadata

Field	Value
Publication number	US-10550326-B2
Application number	US-201515309650-A
Country	US
Kind code	B2
Filing date	Apr 20, 2015
Priority date	May 9, 2014
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

The present invention relates to liquid-crystalline media comprising
one or more polymerisable compounds, preferably 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

and
one or more compounds selected from the group of compounds of formulae I, II, and III,

in which the parameters have the meaning indicated in Claim 1 , 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 polymerisable compounds 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
P a , P b each, independently of one another, are a polymerisable group,
Sp a , Sp b each, independently of one another, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
n1, n2 each, independently of one another, denote 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 independently of one another, denote 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, denote
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which one or more non-adjacent CH 2 groups are optionally replaced by —O— and/or —S— and in which one or more H atoms are optionally replaced by F,
b) 1,4-phenylene or 1,3-phenylene, in which one or two CH groups are optionally replaced by N and in which one or more H atoms are optionally replaced by L,
c) 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 or selenophene-2,5-diyl, each of which is optionally mono- or polysubstituted by L,
d) saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which are optionally replaced by heteroatoms,
and A 3 , alternatively may be a single bond,

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, and
one or more compounds of formulae I, II or III

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 H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 15 C atoms or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15 C atoms,
X 11 and X 12 , independently of one another, denote H, F, Cl, —CN, —NCS, —SF 5 , fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms, and

independently of one another, denote

in which
L 21 denotes R 21 and, in the case where Z 21 and/or Z 22 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X 21 ,
L 22 denotes R 22 and, in the case where Z 21 and/or Z 22 denote trans-CH═CH— or trans-CF═CF—, alternatively denotes X 22 ,
R 21 and R 22 , independently of one another, denote H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 17, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 15,
X 21 and X 22 , independently of one another, denote F, Cl, —CN, —NCS, —SF 5 , 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,
one of Z 21 and Z 22
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

in which
L 31 denotes R 31 or X 31 ,
L 32 denotes R 32 or X 32 ,
R 31 and R 32 , 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 31 and X 32 , independently of one another, denote H, F, Cl, —CN, —NCS, —SF 5 , fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms or fluorinated alkenyl, unfluorinated or fluorinated alkenyloxy or unfluorinated or fluorinated alkoxyalkyl having 2 to 7 C atoms,
Z 31 to Z 33 , independently of one another, denote trans-CH═CH—, trans —CF═CF—, —C≡C— or a single bond, and

independently of one another, denote

and wherein the liquid-crystal medium has a clearing point of 90° C. or more.

2. The liquid-crystal medium according to claim 1 , which comprises one or more mono-reactive polymerisable compounds and/or one or more direactive polymerisable compounds.

3. The liquid-crystal medium according to claim 2 , which comprises one or more mono-reactive polymerisable compounds which are methacrylates and/or one or more direactive polymerisable compounds which are bisacrylates or mixed acrylate methacrylates.

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

5. The liquid-crystal medium according to claim 1 , which comprises one or more compounds of formula II.

6. The liquid-crystal medium according to claim 1 , which comprises one or more compounds of formula III.

7. The liquid-crystal medium according to claim 1 , which additionally comprises a polymerisation initiator which is a UV- or thermo initiator.

8. A method for stabilizing the liquid-crystal medium according to claim 1 , comprising polymerising the polymerisable compounds therein.

9. A composite system comprising a polymer obtained or obtainable from the polymerisation of the polymerisable compounds in the liquid-crystal medium according to claim 1 .

10. A component for high-frequency technology, which comprises the liquid-crystal medium according to claim 1 or a composite system comprising a polymer obtained or obtainable from the polymerisation of the polymerisable compounds in said liquid-crystal medium.

11. The component according to claim 10 , which is suitable for operation in the microwave range.

12. The component according to claim 10 , which is a phase shifter or a LC based antenna element operable in the microwave region.

13. A process for preparing the liquid-crystal medium according to claim 1 , comprising mixing one or more polymerisable compounds of formula P with one or more mesogenic compounds of formulae I, II or III, and optionally with one or more further compounds and/or with one or more additives.

14

Assignees

• Merck Patent Gmbh

Inventors

• Wittek Michael
• Klass Dagmar

Classifications

• C09K2219/11

  used in the High Frequency technical field · CPC title

• C09K2019/0459

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

• C09K2019/183

  Ph-Ph-C≡C-Ph · CPC title

• C09K2019/3063

  Cy-Ph-C≡C-Ph · CPC title

• C09K19/42 Primary

  Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 · CPC title