Aromatic isothiocyanates

Patent metadata

Field	Value
Publication number	US-11739265-B2
Application number	US-202017637511-A
Country	US
Kind code	B2
Filing date	Aug 27, 2020
Priority date	Aug 28, 2019
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

The present invention relates to aromatic isothiocyanates of formula Uas defined in claim 1, to liquid-crystalline media comprising one or more compounds of formula U and to 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 U

in which
R U 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 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 U1 , Z U2 identically or differently, denote —CH═CH—, —CH═CF—, —CH═CF—, —CF═CH—, —C≡C— or a single bond,
X 1 , X 2 ,
X 3 and X 4 identically or differently, denote Cl or F,
t is 0 or 1, and

 identically or differently, denote a radical selected from:
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, wherein tetrafluoro-1,4-phenylene is excluded,
b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclo-hexenylene, 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 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, and selenophene-2,5-diyl, each of which may also 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, alkoxy, alkylcarbonyl, alkoxy-carbonyl, 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

 on each occurrence, independently of one another, denote

 wherein
 alternatively denotes

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

3. The compound according to claim 1 , wherein Z U1 and Z U2 , identically or differently, denote —C≡C— or a single bond.

4. The compound according to claim 1 , wherein the compound is selected from the group consisting of compounds of formulae U-1 to U-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, and
R U , X 1 , X 2 , X 3 and X 4 have the meanings given for formula U.

5. The compound according to claim 1 , wherein X 1 , X 2 , X 3 and X 4 denote F.

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

7. The compound according to claim 1 , wherein R U denotes R P as defined for formula U.

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 further comprises one or more compounds selected from the group consisting of 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 be replaced by

n is 0, 1 or 2,

 to

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

 to

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 , wh

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C09K19/18

  the chain containing carbon-to-carbon triple bonds, e.g. tolans · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/3056

  Cy-Ph-CH=CH-Ph · CPC title

• C07D309/04

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title