# US 11,306,251 B2 · Liquid-crystalline medium

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- Number: US 11,306,251 B2
- Document ID: US11306251B2
- Status: Granted
- Kind: B2
- Application number: 16/414,283
- Filed: 2019-05-16
- Published: 2019-11-21
- Granted: 2022-04-19
- Earliest claimed: 2018-05-16
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Dagmar Klass; Carsten Fritzsch; Dmitry Ushakov; Beate Schneider
- Web page: https://patentgrep.com/patent/US11306251B2

## CPC

- C09K 19/3059: {in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds}
- C09K 19/12: at least two benzene rings directly linked, e.g. biphenyls
- C09K 19/16: the chain containing carbon-to-carbon double bonds, e.g. stilbenes
- C09K 19/18: the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K 19/3001: {Cyclohexane rings}
- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/36: Steroidal liquid crystal compounds
- C09K 19/586: {Optically active dopants; chiral dopants}
- C09K 19/588: {Heterocyclic compounds}
- H01Q 1/364: {using a particular conducting material, e.g. superconductor}
- H01Q 19/06: using refracting or diffracting devices, e.g. lens {(radome H01Q1/42)}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/181: {Ph-C≡C-Ph}
- C09K 2019/183: {Ph-Ph-C≡C-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3063: {Cy-Ph-C≡C-Ph}
- H01Q 3/44: varying the electric or magnetic characteristics of reflecting, refracting, or diffracting devices associated with the radiating element
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H01Q: ANTENNAS, i.e. RADIO AERIALS (radiators or antennas for microwave heating H05B6/72)

## Abstract

Liquid-crystalline media having one or more compounds of formula C and high-frequency components containing these media, especially microwave components for high-frequency devices, such as devices for shifting the phase of microwaves, tunable filters, tunable metamaterial structures, and electronic beam steering antennas (e.g. phased array antennas).

## Claims

### Claim 1

A liquid crystal medium, comprising at least one compound of formula C
in which
RC denotes H, unfluorinated alkyl or unfluorinated alkoxy having 1 to 12 C atoms, or unfluorinated alkenyl, unfluorinated alkenyloxy or unfluorinated alkoxyalkyl having 2 to 12 C atoms, in which alkyl, alkoxy, alkenyl, alkenyloxy or alkoxy-alkyl one or more CH2-groups may be replaced by
LC1, LC2 identically or differently, denote H, Cl or F,
RC1, RC2, RC3,
RC4, RC5, and RC6 identically or differently, denote H, F, Cl, or alkyl having 1 to 6 C atoms, or cyclopropyl, cyclobutyl or cyclopentyl;
and
one or more compounds of I or II,
and at least one compound of formula III-1
in which
R1 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, in which alkyl, alkoxy, alkenyl, alkenyloxy or alkoxy-alkyl one or more CH2-groups may be replaced by
n is 0, 1 or 2,
on each occurrence, independently of one another, denote
in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms,
and wherein
alternatively denotes
R2 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, in which one or more CH2-groups may be replaced by
Z21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and
independently of one another, denote
in which
RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms;
R3 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, in which one or more CH2-groups may be replaced by
one of Z31 and Z32, denotes trans-CH═CH—, trans-CF═CF— or —C≡C— and the other one, independently thereof, denotes —C≡C—, trans-CH═CH—, trans-CF═CF— or a single bond, and
independently of one another, denote
in which RL, on each occurrence identically or differently, denotes H or alkyl having 1 to 6 C atoms,
and wherein
alternatively denotes
the liquid crystal medium also comprising 10 to 32% by weight of one or more compounds of formula T
in which
RT denotes halogen, CN, NCS, RF, RF—O— or RF—S—, wherein
RF denotes fluorinated alkyl or fluorinated alkenyl having 2 to 12 C atoms,
on each occurrence, independently of one another, denote
L1 and L2 identically or differently, denote Cl, F, alkyl having 1 to 6 C atoms or cyclopropyl, cyclobutyl or cyclopentyl, and
t is 0, 1 or 2
wherein the one or more compounds of formula C and one or more compounds of formula III-1 are present in the medium in an amount of 35 to 50%.

### Claim 2 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the medium has a clearing temperature of 90° C. or more.

### Claim 3 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the medium has a birefringence at 20° C. and 598.3 nm of 0.300 or more.

### Claim 4 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the medium comprises a compound of formula I where n is 0, in a total concentration of 10% or less.

### Claim 5 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the compounds of formula T are of the formulae T-1 or T-2 or mixtures thereof
n is 1, 2, 3, 4, 5, 6, or 7,
are as defined in claim 1.

### Claim 6 (depends on 5)

The liquid-crystal medium according to claim 5, wherein the medium comprises one or more compounds of the formula T-1 in which n is 1.

### Claim 7 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the compound of formula I is of formula I-1 to I-5
in which
L1, L2 and L3 on each occurrence, identically or differently, denote H or F,
are as defined in claim 1.

### Claim 8 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the compound of formula II is of formulae II-1 to II-3
wherein R2,
and are as defined in claim 1.

### Claim 9 (depends on 8)

The liquid-crystal medium according to claim 8, wherein the medium comprises one or more compounds of formula II-1 in a total concentration of 25% or less.

### Claim 10 (depends on 1)

The liquid-crystal medium according to claim 1, wherein the medium additionally comprises one or more chiral compounds.

### Claim 11 (depends on 10)

The liquid-crystal medium according to claim 10, wherein the one or more chiral compounds are chiral dopants of the formulae A-I, A-II, A-III or A-Ch:
in which
Ra11, Ra12
and Rb12, independently of one another, denote alkyl having 1 to 15 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN, with the proviso that Ra12 is different from Rb12
Ra21 and Ra22, independently of one another, denote alkyl having 1 to 15 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
Ra31, Ra32
and Rb32, independently of one another, denote C1-15 straight-chain or C2-15 branched alkyl, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN, with the proviso that Ra32 is different from Rb32;
Rz denotes H, CH3, F, Cl, or CN,
R8 has one of the meanings of Ra11,
Z8 denotes —C(O)O—, CH2O, CF2O or a single bond,
A11 is independently defined as A′2 below, or alternatively denotes
A12 denotes
in which r is 0, 1, 2, 3, or 4;
L12, on each occurrence, independently of one another, denotes halogen, CN, C1-12-alkyl, C2-12-alkenyl, C1-12-alkoxy or C2-12-alkenyloxy and in which one or more H atoms are optionally replaced with halogen;
A21 denotes
A22 independently has the meanings given for A12
A31 independently has the meanings given for A11,
alternatively denotes
A32 independently has the meanings given for A12
n2 on each occurrence, identically or differently, is 0, 1 or 2, and
n3 is 1, 2 or 3.

### Claim 12 (depends on 1)

A high-frequency technology component comprising in said component the liquid crystal medium according to claim 1.

### Claim 13 (depends on 12)

The component according to claim 12, wherein the component is suitable for operation in the microwave range.

### Claim 14 (depends on 12)

The component according to claim 12, wherein the component is a liquid-crystal based antenna element, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network or a varactor.

### Claim 15 (depends on 12)

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

### Claim 16 (depends on 1)

A liquid crystal lens or a liquid crystal wavefront corrector, comprising a liquid-crystal medium according to claim 1.

### Claim 17 (depends on 1)

A process for the preparation of a liquid-crystal medium according to claim 1, comprising mixing one or more compounds of formula C with one or more compounds of formula T and III-1 and optionally with one or more compounds of formula I and/or II and optionally additional mesogenic compounds; and optionally adding a chiral compound.