Liquid-crystalline medium and high-frequency components comprising same

Patent metadata

Field	Value
Publication number	US-11208594-B2
Application number	US-201515539181-A
Country	US
Kind code	B2
Filing date	Dec 14, 2015
Priority date	Dec 29, 2014
Publication date	Dec 28, 2021
Grant date	Dec 28, 2021

Abstract

Liquid-crystalline media comprisingone or more compounds of formula Gandone 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 components comprising these media, are suitable for use in high-frequency technology, in particular, in phase shifters and microwave array antennas.

First claim

The invention claimed is:

1. A liquid crystal medium, comprising:
one or more compounds of formula G-2

wherein
R 1 and R 2 independently of one another, denote unfluorinated alkyl or unfluorinated alkoxy, each having 1 to 15 C atoms, un-fluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl, each having 2 to 15 C atoms;
one or more compounds selected from the group of compounds of formulae II-1a and II-1b

in which
R 21 and R 22 , 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; and
one or more compounds of formula IV

wherein

Denotes

R 41 to R 42 , 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 3 to 15 C atoms.

2. The liquid crystal medium according to claim 1 , wherein said medium further comprises one or more 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 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, 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—, —O—, —CH 2 —, —(CH 2 ) 3 —, or —CF 2 —,
Z 1 , Z 4 each, 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—, —O—, —CH 2 —, —(CH 2 ) 3 —, —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 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 may each be replaced by —O— or —S— and in which, in addition, one or more H atoms may each be replaced by F,
b) the group consisting of 1,4-phenylene and 1,3-phenylene, in which, in addition, one or two CH groups may each be replaced by N and in which, in addition, one or more H atoms may each be 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,
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 heteroatoms, where, in addition, one or more H atoms in these radicals may each be replaced by L, and/or one or more double bonds may each be replaced by single bonds, and/or one or more CH groups may be replaced by N,
and A 3 , alternatively may be a single bond, and

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 , straight-chain, optionally fluorinated, alkyl or alkoxy having 1 to 12 C atoms, branched, optionally fluorinated, alkyl or alkoxy having 3 to 12 C atoms, or alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 2 to 12 C atoms, in each case optionally fluorinated.

3. The liquid crystal medium according to claim 1 , wherein said medium further comprises one or more compounds selected from the group of compounds of formulae CC and CP

wherein
Alkenyl denotes unfluorinated alkenyl having 2 to 15 C atoms,
R 01 denotes unfluorinated alkyl having 1 to 17 C atoms or unfluorinated alkenyl having 2 to 15 C atoms, and
R 02 denotes unfluorinated alkyl having 1 to 17 C atoms or unfluorinated alkenyl having 2 to 15 C atoms.

4. The liquid crystal medium according to claim 1 , wherein said medium comprises one or more chiral compounds having an absolute value of the HTP of 10 μm −1 or more.

5. The liquid crystal medium according to claim 1 , wherein said medium further comprises one or more chiral compounds selected from the group of compounds of formulae A-I to A-VI:

including the (R,S), (S,R), (R,R) and (S,S) enantiomers, which are not shown,

in which
R a11 and R a12 , independently of one another, are alkyl, oxaalkyl or alkenyl having from 2 to 9 carbon atoms, and R a11 is alternatively methyl or alkoxy having from 1 to 9 carbon atoms,
R a21 and R a22 , independently of one another, are alkyl or alkoxy having from 1 to 9 carbon atoms, oxaalkyl, alkenyl or alkenyloxy having from 2 to 9 carbon atoms,
R a31 and R a32 , independently of one another, are alkyl, oxaalkyl or alkenyl having from 2 to 9 carbon atoms, and R a31 is alternatively methyl or alkoxy having from 1 to 9 carbon atoms,

are each, independently of one another, 1,4-phenylene, which may also be mono-, di- or trisubstituted by L, or 1,4-cyclohexylene,
L is H, F, Cl, CN or optionally halogenated alkyl or alkoxy having 1 to 7 carbon atoms or alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 2 to 7 carbon atoms,
c is 0 or 1,
Z 0 is —CO—O—, —O—CO—, —CH 2 CH 2 — or a single bond, and
R 0 is alkyl-carbonyloxy alkyl or alkoxy having 1 to 12 carbon atoms or alkylcarbonyl, alkoxycarbonyl or alkoxycarbonyloxy having 2 to 12 carbon atoms,
X 1 , X 2 , Y 1 and Y 2 are each, independently of one another, F, Cl, Br, I, CN, SCN, SF 5 , a straight-chain alkyl having from 1 to 25 carbon atoms or a branched alkyl having 3 to 25 carbon atoms, which in each case may be monosubstituted or polysubstituted by F, Cl, Br, I or CN and in which, in addition, one or more non-adjacent CH 2 groups may each, independently of one another, be replaced by —O—, —S—, —NH—, NR 0 —, —CO—, —CO—O—, —O—CO—, —OC(O)O—, —S—CO—, —CO—S—, —CH═CH— or —C≡C— in such a way that O and/or S atoms are not bonded directly to one another, a polymerizable group or cycloalkyl or aryl having 3 to 20 carbon atoms, which may optionally be monosubstituted or polysubstituted by halogen or by a polymerizable group,
x 1 and x 2 are each, independently of one anoth

Assignees

• Merck Patent Gmbh

Inventors

• Wittek Michael
• Brocke Constanze
• Reiffenrath Volker

Classifications

• C09K2219/11

  used in the High Frequency technical field · CPC title

• C09K2019/183

  Ph-Ph-C≡C-Ph · CPC title

• C09K2019/188

  Ph-C≡C-Ph-C≡C-Ph · CPC title

• C09K19/04

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• C09K2019/0459

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