Compounds having a C—C triple bond and use thereof in liquid-crystal mixtures

Patent metadata

Field	Value
Publication number	US-9868905-B2
Application number	US-201314430460-A
Country	US
Kind code	B2
Filing date	Sep 3, 2013
Priority date	Sep 21, 2012
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

Compounds containing at least one C—C triple bond of the formula I

R 1 -[A 1 -Z 1 ] m -A 2 A 3 -[Z 2 -A 4 ] n -[Z 3 -A 5 ] o -R 2   I,

which have neutral dielectric anisotropy, to the use thereof for high-frequency components, to liquid-crystalline media comprising the compounds, and to high-frequency components, in particular antennae, especially for the giga- and terahertz region, comprising these media. The liquid-crystalline media serve, for example, for the phase shifting of microwaves for tuneable phased-array antennae.

First claim

The invention claimed is:

1. A compound of the formula I
R 1 -[A 1 -Z 1 ] m -A 2 A 3 -[Z 2 -A 4 ] n -[Z 3 -A 5 ] o -R 2   I

in which
one of A 2 and A 3 denotes

the other of A 2 and A 3 , A 1 , A 4 and A 5 ,
independently of one another, denote
a) 1,4-phenylene, in which one or more CH groups may be replaced by N, or
b) a radical of the formula

and in which, in the groups a) and b),
one or more H atoms are optionally replaced, independently, by in each case a group Y,
Y denotes Br, Cl, F, CN, —NCS, —SCN, SF 5 , C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group,
R 1 and R 2 , independently of one another, denote a straight-chain alkyl radical having 1 to 15 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—, —(CO)O—, —O(CO)—, —(CO)—, or —O— in such a way that O atoms are not linked directly to one another,
R 3 denotes C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 1 -C 10 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl or a mono- or polyfluorinated C 1 -C 10 alkyl or alkoxy group,
Z 1 , Z 2 and Z 3 , independently of one another, denote a single bond, and
m is 0, n and o are 1, where (m+n+o) is 2.

2. A compound according of claim 1 , wherein the sub-formula “-A 2 -≡-A 3 -” of the formula I is selected from the group consisting of:

in which the parameters Y and R 3 have the meanings given in claim 1 .

3. A compound of claim 1 , wherein the rings A 1 to A 5 , if present, each denote an optionally substituted 1,4-phenylene ring.

4. A liquid-crystal medium, wherein said liquid-crystal medium comprises one or more compounds of the formula I according to claim 1 .

5. A liquid-crystal medium of claim 4 , wherein said liquid-crystal medium 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 alkynyl, 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, q independently denote 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

in which L independently denotes branched or unbranched alkyl, alkenyl or alkynyl having 1 to 12 C atoms, in which, in addition, one or more “—CH 2 —” groups may be replaced, independently of one another, by O, or denotes C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, fluorinated alkyl or alkenyl, fluorinated alkoxy or alkenyloxy,
F, Cl, Br, CN, NCS, SCN or SF 5 .

6. A liquid-crystal medium of claim 4 , wherein the concentration of the compounds of the formula I in the medium is in the range from in total 5% to 95%.

7. A method comprising including a compound of formula I in a component for high-frequency technology.

8. A method comprising including a compound of formula I in a liquid-crystalline medium.

9. A process for the preparation of a liquid-crystal medium according to claim 4 , wherein one or more compounds of the formula I are mixed with one or more further compounds and optionally with one or more additives.

10. A component for high-frequency technology, wherein said component for high-frequency technology contains a liquid-crystal medium according to claim 4 .

11. A component for high-frequency technology of claim 10 , wherein said component for high-frequency technology comprises one or more functionally connected phase shifters.

12. A method of comprising including a liquid-crystal medium according to claim 4 in a component for high-frequency technology.

13. A phased array antenna, wherein said phased array antenna comprises one or more components according to claim 10 .

14. A process for the preparation of 2-alkyl-1-bromo-3-fluorobenzenes, wherein 1-bromo-3-fluorobenzene is ortho-metallated using LDA and then alkylated in situ using the corresponding alkyl iodide.

15. The compound of claim 1 wherein formula I is defined as one of the following structures

wherein
R 1 and R 2 denotes, identically or differently, an alkyl radical having 2 to 7 C atoms,
R 3 denotes an alkyl radical having 1 to 7 C atoms, an alkenyl radical having 2 to 7 C atoms, a cycloalkyl radical having 3 to 6 C atoms or a cycloalkenyl radical having 4 to 6 C atoms.

Assignees

• Merck Patent Gmbh

Inventors

• Brocke Constanze
• Jasper Christian
• Pauluth Detlef
• Manabe Atsutaka

Classifications

• C07C15/54

  containing a group with formula[IMAGE cpc-sch-C07C-0956.gif] · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C07C17/26

  by reactions involving an increase in the number of carbon atoms in the skeleton · CPC title

• C07C25/24

  Halogenated aromatic hydrocarbons with unsaturated side chains · CPC title