Compounds for a liquid-crystalline medium, and the use thereof for high-frequency components

Patent metadata

Field	Value
Publication number	US-9752076-B2
Application number	US-201013505761-A
Country	US
Kind code	B2
Filing date	Oct 6, 2010
Priority date	Nov 4, 2009
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The present invention relates to compounds of the formula I

where one or more of the radicals A 1-5 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.

First claim

The invention claimed is:

1. Compounds of the formula I

in which
A 1-5 , 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 CH 2 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, SF 5 , C 1 -C 10 alkyl, C 1 -C 10 alkoxy or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group,
and where
at least one radical from A 1 to A 5 represents a radical according to a),
R 1 and R 2 each, independently of one another, denote a halogenated or unsubstituted alkyl radical having 2 to 10 C atoms, where, in addition, one or more CH 2 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, CF 3 , OCF 3 , SCN, NCS or SF 5 ,

Z 2 denotes —C≡C— or

Y 1 , Y 2 , denote F,
Z 1 , Z 5 , independently of one another, denote a single bond, —C≡C—, —CH═CH—, —CH 2 O—, —(CO)O—, —CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 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.

2. Compounds according to claim 1 , characterised in that at least one group from A 2 , A 3 and A 4 denotes an optionally substituted 1,4-naphthylene radical or a 1,4-anthracenylene radical.

3. 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.

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

5. Liquid-crystal medium, characterised in that it comprises one or more compounds of the formula I

in which
A 1-5 , 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 CH 2 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, SF 5 , C 1 -C 10 alkyl, C 1 -C 10 alkoxy or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group,

and where
at least one radical from A 1 to A 5 represents a radical according to a),
R 1 and R 2 each, independently of one another, denote a halogenated or unsubstituted alkyl radical having 2 to 10 C atoms, where, in addition, one or more CH 2 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, CF 3 , OCF 3 , SCN, NCS or SF 5 ,

Z 2 denotes C≡C— or

Y 1 , Y 2 , independently of one another, denote H, F, Cl, or C 1 -C 10 alkyl,
Z 1 , Z 5 , independently of one another, denote a single bond, —C≡C—, —CH═CH—, —CH 2 O—, —(CO)O—, —CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 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.

6. 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
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 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 11 and X 12 , independently of one another, denote F, Cl, Br, —CN, —NCS, —SCN, —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,
p denotes 0 or 1,
Z 11 to Z 13 , 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 CH 2 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, SF 5 , C 1 -C 10 alkyl, C 1 -C 10 alkoxy or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group.

7. 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%.

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

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

10. 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.

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

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

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

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

Assignees

• Jasper Christian
• Montenegro Elvira
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka
• Merck Patent Gmbh

Inventors

• Jasper Christian
• Montenegro Elvira
• Pauluth Detlef
• Reiffenrath Volker
• Manabe Atsutaka

Classifications

• C07C22/08

  containing fluorine · CPC title

• C07C21/185

  Tetrafluoroethene · CPC title

• C09K2219/11

  used in the High Frequency technical field · CPC title

• C07C21/19

  Halogenated dienes · CPC title

• C07C21/22

  containing carbon-to-carbon triple bonds · CPC title