Aromatic isothiocyanates

Patent metadata

Field	Value
Publication number	US-11834599-B2
Application number	US-202017783865-A
Country	US
Kind code	B2
Filing date	Dec 8, 2020
Priority date	Dec 10, 2019
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

Aromatic isothiocyanates of formula Cliquid-crystalline media comprising one or more compounds of formula C, and high-frequency components comprising 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.

First claim

The invention claimed is:

1. A compound of formula C

in which
R C denotes H, alkyl or alkoxy having 1 to 12 C atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 C atoms, in which one or more CH 2 -groups may be replaced by

 or denotes a group R P ,
R P denotes halogen, CN, NCS, R F , R F —O— or R F —S—, wherein
R F denotes fluorinated alkyl having 1 to 9 C atoms or fluorinated alkenyl having 2 to 9 C atoms,
Z C1 , Z C2 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—,
—CF═CH—, —C≡C— or a single bond,
X denotes Cl or F,
Y denotes H, Cl, F, alkyl or alkoxy each having 1 to 6 C atoms,
t is 0, 1 or 2, and

denote a radical selected from the following groups:

a) the group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, in which one or two CH groups may be replaced by N and in which one or more H atoms may be replaced by L,
b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene, bicyclo[1.1.1]-pentane-1,3-diyl, 4,4′-bicyclohexylene, bicyclo[2.2.2]octane-1,4-diyl or spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and in which one or more H atoms may be replaced by F,
c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl or selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L, and
L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms.

2. The compound according to claim 1 , wherein

independently of one another, denote

wherein

 alternatively denotes

 and

L 1 and L 2 identically or differently, denote F, Cl or straight chain alkyl having 1 to 12 C atoms, straight-chain alkenyl having 2 to 12 C atoms, or branched or cyclic alkyl or alkenyl having 3 to 12 C atoms.

3. The compound according to claim 1 , wherein Z C1 and Z C2 , identically or differently, denote —C≡C— or a single bond.

4. The compound according to claim 1 , selected from compounds of formulae C-1 to C-11

in which
L 1 , L 2 and L 3 identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl.

5. The compound according to claim 1 , wherein X denotes F.

6. The compound according to claim 1 , wherein R C denotes alkyl having 1 to 12 C atoms.

7. The compound according to claim 1 , wherein the group R C denotes R P .

8. A liquid crystal medium comprising one or more compounds according to claim 1 .

9. The liquid crystal medium according to claim 8 , wherein the medium comprises one or more compounds of formulae I, II or III,

in which
R 1 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 CH 2 -groups may be replaced by

n is 0, 1 or 2,

on each occurrence, independently of one another, denote

in which R L , on each occurrence identically or differently,
denotes H or alkyl having 1 to 6 C atoms,
and wherein

 alternatively denotes

R 2 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 CH 2 -groups may be replaced by

Z 21 denotes trans-CH═CH—, trans-CF═CF— or —C≡C—, and

independently of one another, denote

in which R L , on each occurrence identically or differently,
denotes H or alkyl having 1 to 6 C atoms;

R 3 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 CH 2 -groups may be replaced by

one of Z 31 and Z 32 , 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 R L , on each occurrence identically or differently,
denotes H or alkyl having 1 to 6 C atoms,
and wherein

 alternatively denotes

10. The liquid-crystal medium according to claim 9 , wherein the medium comprises one or more compounds selected from compounds of formulae I-1 to I-5

in which
L 1 , L 2 and L 3 on each occurrence, identically or differently, denote H or F, wherein

Assignees

• Merck Patent Gmbh

Inventors

• Brocke Constanze
• Ushakov Dmitry
• Klass Dagmar
• Fritzsch Carsten

Classifications

• C09K19/3098 Primary

  Unsaturated non-aromatic rings, e.g. cyclohexene rings · CPC title

• C09K19/3059

  in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds · CPC title

• C09K2019/0444

  characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title