# US 9,752,076 B2 · Compounds for a liquid-crystalline medium, and the use thereof for high-frequency components

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- Number: US 9,752,076 B2
- Document ID: US9752076B2
- Status: Granted
- Kind: B2
- Application number: 13/505,761
- Filed: 2010-10-06
- Published: 2012-10-25
- Granted: 2017-09-05
- Earliest claimed: 2009-11-04
- Assignees: Merck Patent GmbH
- Applicants: Christian Jasper; Elvira Montenegro; Detlef Pauluth; Volker Reiffenrath; Atsutaka Manabe
- Inventors: Christian Jasper; Elvira Montenegro; Detlef Pauluth; Volker Reiffenrath; Atsutaka Manabe
- Web page: https://patentgrep.com/patent/US9752076B2

## CPC

- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C07C 13/47: with a bicyclo ring system containing ten carbon atoms
- C07C 13/573: with three six-membered rings
- C07C 15/24: containing two rings
- C07C 15/28: Anthracenes
- C07C 21/185: Tetrafluoroethene
- C07C 21/19: Halogenated dienes
- C07C 21/22: containing carbon-to-carbon triple bonds
- C07C 22/08: containing fluorine
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/42: Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K 2219/11: used in the High Frequency technical field
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to compounds of the formula I where one or more of the radicals A1-5 denote a 1,4-naphthylene or 1,4- or 9,10-anthracenylene radical, and the other parameters are as defined in Claim 1. The invention additionally includes liquid-crystalline media which comprise the title compounds, and components for high-frequency technology which comprise these media, in particular phase shifters and microwave array antennae.

## Claims

### Claim 1

Compounds of the formula I
in which
A1-5, independently of one another, denote
a) a radical of the formula
b) 1,4-phenylene, in which one or more CH groups may be replaced by N,
c) trans-1,4-cyclohexylene or cyclohexenylene, in which, in addition, one or two non-adjacent CH2 groups may be replaced by —O— and/or —S— and in which H may be replaced by F,
or
d) a radical from the group 1,4-bicyclo[2.2.2]octylene, cyclobut-1,3-diyl, spiro[3.3]heptane-2,6-diyl,
and in which, in groups a), b), c) and d),
one or more H atoms may also be replaced by Br, Cl, F, CN, —NCS, —SCN, SF5, C1-C10 alkyl, C1-C10 alkoxy or a mono- or polyfluorinated C1-C10 alkyl or alkoxy group,
and where
at least one radical from A1 to A5 represents a radical according to a),
R1 and R2 each, independently of one another, denote a halogenated or unsubstituted alkyl radical having 2 to 10 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)— or —S— in such a way that O or S atoms are not linked directly to one another,
or F, Br, CN, CF3, OCF3, SCN, NCS or SF5,
Z2 denotes —C≡C— or
Y1, Y2, denote F,
Z1, Z5, independently of one another, denote a single bond, —C≡C—, —CH═CH—, —CH2O—, —(CO)O—, —CF2O—, —CF2CF2—, —CH2CF2—, —CH2CH2—, —(CH2)4—, —CH═CF— or —CF═CF—, where asymmetrical bridges may be oriented to both sides, and
m, n, independently of one another, denote 0, 1 or 2.

### Claim 2 (depends on 1)

Compounds according to claim 1, characterised in that at least one group from A2, A3 and A4 denotes an optionally substituted 1,4-naphthylene radical or a 1,4-anthracenylene radical.

### Claim 3 (depends on 1)

Compounds according to claim 1, characterised in that the compounds of the formula I contain one or two optionally substituted 1,4-naphthylene radicals or 1,4-anthracenylene radicals.

### Claim 4 (depends on 1)

Compounds according to claim 1, characterised in that m and n are 0.

### Claim 5

Liquid-crystal medium, characterised in that it comprises one or more compounds of the formula I
in which
A1-5, independently of one another, denote
a) a radical of the formula
b) 1,4-phenylene, in which one or more CH groups may be replaced by N,
c) trans-1,4-cyclohexylene or cyclohexenylene, in which, in addition, one or two non-adjacent CH2 groups may be replaced by —O— and/or —S— and in which H may be replaced by F,
or
d) a radical from the group 1,4-bicyclo[2.2.2]octylene, cyclobut-1,3-diyl, spiro[3.3]heptane-2,6-diyl,
and in which, in groups a), b), c) and d),
one or more H atoms may also be replaced by Br, Cl, F, CN, —NCS, —SCN, SF5, C1-C10 alkyl, C1-C10 alkoxy or a mono- or polyfluorinated C1-C10 alkyl or alkoxy group,
and where
at least one radical from A1 to A5 represents a radical according to a),
R1 and R2 each, independently of one another, denote a halogenated or unsubstituted alkyl radical having 2 to 10 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CO)O—, —O(CO)—, —(CO)— or —S— in such a way that O or S atoms are not linked directly to one another,
or F, Br, CN, CF3, OCF3, SCN, NCS or SF5,
Z2 denotes C≡C— or
Y1, Y2, independently of one another, denote H, F, Cl, or C1-C10 alkyl,
Z1, Z5, independently of one another, denote a single bond, —C≡C—, —CH═CH—, —CH2O—, —(CO)O—, —CF2O—, —CF2CF2—, —CH2CF2—, —CH2CH2—, —(CH2)4—, —CH═CF— or —CF═CF—, where asymmetrical bridges may be oriented to both sides, and
m, n, independently of one another, denote 0, 1 or 2.

### Claim 6 (depends on 5)

Liquid-crystal medium according to claim 5, characterised in that it additionally comprises one or more compounds selected from the compounds of the formula II:
in which
L11 denotes R11 or X11,
L12 denotes R12 or X12,
R11 and R12, independently of one another, denote 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,
X11 and X12, independently of one another, denote F, Cl, Br, —CN, —NCS, —SCN, —SF5, 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 denotes 0 or 1,
Z11 to Z13, independently of one another, denote trans-CH═CH—, trans-CF═CF—, —C≡C— or a single bond, and
independently of one another, denote
a) 1,4-phenylene, in which one or more, preferably one or two, CH groups may be replaced by N,
b) trans-1,4-cyclohexylene or cyclohexenylene, in which, in addition, one or two non-adjacent CH2 groups may be replaced by —O— and/or —S— and in which H may be replaced by F,
and in which, in groups a) and b), one or more H atoms may also be replaced by Br, Cl, F, CN, —NCS, —SCN, SF5, C1-C10 alkyl, C1-C10 alkoxy or a mono- or polyfluorinated C1-C10 alkyl or alkoxy group.

### Claim 7 (depends on 5)

Liquid-crystal medium according to claim 5, characterised in that the concentration of the compounds of the formula I in the medium is in the range from in total 5% to 95%.

### Claim 8 (depends on 5)

A method comprising adding a compound of the formula I according to claim 5 to a liquid-crystalline mixture.

### Claim 9 (depends on 1)

A method comprising adding a compound of the formula I according to claim 1 to a component for high-frequency technology.

### Claim 10 (depends on 5)

Process for the preparation of a liquid-crystal medium according to claim 5, characterised in that one or more compounds of the formula I are mixed with one or more further compounds and optionally with one or more additives.

### Claim 11 (depends on 5)

Component for high-frequency technology, characterised in that it comprises a liquid-crystal medium according to claim 5.

### Claim 12 (depends on 11)

Component according to claim 11, characterised in that it is one or more functionally connected phase shifters.

### Claim 13 (depends on 5)

A method comprising incorporating a liquid-crystal medium according to claim 5 in a component for high-frequency technology.

### Claim 14 (depends on 11)

Phase-controlled group antenna, characterised in that it comprises one or more components according to claim 11.

### Claim 15 (depends on 5)

Liquid-crystal medium according to claim 5, wherein for one or more compounds of the formula I, Y1 and Y2 denote F.