Heteroaromatic isothiocyanates

Patent metadata

Field	Value
Publication number	US-12359128-B2
Application number	US-202118266657-A
Country	US
Kind code	B2
Filing date	Dec 14, 2021
Priority date	Dec 17, 2020
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

Heteroaromatic isothiocyanates of formula N

wherein R N , A N1 , A N2 , Z N1 , Z N2 , W, X 1 , X 2 , and n are as defined herein can be used in liquid crystalline media. Liquid-crystalline media comprising one or more compounds of formula N are suitable for use in high-frequency components, 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 liquid-crystal medium comprising:
one or more compounds of formula N

in which
R N 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 N1 and Z N2 , identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —C≡C—C≡C—, or a single bond,

W denotes N, C—F or C—Cl,
X 1 and X 2 , identically or differently, denote H, Cl, F, methyl, or ethyl,

on each occurrence, identically or differently, denote a radical selected from:
a) the group consisting of 1,4-phenylene, 1,4-naphthylene, and 2,6-naphthylene, in which one or two CH groups may each be replaced by N and in which one or more H atoms may each 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, and spiro[3.3]heptane-2,6-diyl, in which one or more non-adjacent CH 2 groups may each be replaced by —O— or —S— and in which one or more H atoms may each be replaced by F, and
c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may be mono- or polysubstituted by L,

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 , or straight-chain, in each case optionally fluorinated, alkyl having 1 to 12 C atoms, alkoxy having 1 to 12 C atoms, alkylcarbonyl having 2 to 12 C atoms, alkoxycarbonyl having 2 to 12 C atoms, alkylcarbonyloxy having 2 to 12 C atoms, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched, in each case optionally fluorinated, alkyl having 3 to 12 C atoms, alkoxy having 3 to 12 C atoms, alkylcarbonyl having 4 to 12 C atoms, alkoxycarbonyl having 4 to 12 C atoms, alkylcarbonyloxy having 4 to 12 C atoms, or alkoxycarbonyloxy having h to 12 C atoms, and
n is 0, 1 or 2; and
one or more compounds selected from the group of compounds consisting of the compounds of formulae I, II and 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 each 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 each 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 each 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

2. The liquid-crystal medium according to claim 1 ,
wherein the one or more compounds of formula N are selected from the group of compounds consisting of the compounds of formulae N-1, N-2 and N-3:

in which
R N 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 each be replaced by

and

Z N1 , Z N2 , X 1 , X 2 and n, have the respective meanings given in claim 1 for formula N.

3. The liquid-crystal medium according to claim 1 ,
wherein the one or more compounds of formula N are selected from the group of compounds consisting of the compounds of formulae N-1, N-2 and N-3:

in which
R N 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 and

Z N1 , Z N2 , X 1 , X 2 and n, have the respective meanings given in claim 1 for formula N.

4. The liquid-crystal medium according to claim 1 , in which X 1 and X 2 denote H.

5. The liquid-crystal medium according to claim 1 , wherein in formula N X 1 denotes H and X 2 denotes F or Cl.

6. The liquid-crystal medium according to claim 1 , wherein in formula N X 1 denotes F or Cl and X 2 denotes H.

Assignees

• Merck Patent Gmbh

Inventors

• Brocke Constanze
• Klass Dagmar
• Fritsch Carsten
• Parham Amir Hossain

Classifications

• C09K2219/17

  used as a medium, in which detection of chemical compounds takes place · CPC title

• C09K2019/3063

  Cy-Ph-C≡C-Ph · CPC title

• C09K2019/3062

  Cy-C≡C-Ph · CPC title

• C09K2019/306

  Cy-C≡C-Cy · CPC title

• C09K2019/305

  Cy-CH=CH-Cy · CPC title