Fluorinated aromatic compounds

Patent metadata

Field	Value
Publication number	US-11964933-B2
Application number	US-202017767080-A
Country	US
Kind code	B2
Filing date	Oct 8, 2020
Priority date	Oct 10, 2019
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

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 , Z U3 identically or differently, denote —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C— or a single bond,
X 1 , X 2 identically or differently, denote H, Cl, F, CH 3 or C 2 H 5 ,
Y 1 , Y 2 , Y 3 , Y 4 identically or differently, denote H, F, Cl, or straight chain alkyl, or alkoxy, each having 1 to 12 C atoms or straight chain alkenyl or alkenyloxy, each having 2 to 12 C atoms or branched or cyclic alkyl, alkenyl, alkoxy or alkenyloxy, each having 3 to 12 C atoms, where at least one of Y 1 , Y 2 , Y 3 and Y 4 is different from F,
s is 0, 1 or 2,
t is 0, 1 or 2, and
s+t is 0, 1 or 2,

identically or differently, 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, 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, and
c) the group consisting of thiophene-2,5-diyl, thieno[3,2-b]thiophene-2,5-diyl, 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, 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

on each occurrence, independently of one another, denote

in which one or two CH-groups may be replaced by N, and
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 or straight chain alkenyl having 2 to 12 C atoms or branched or cyclic alkyl or alkenyl each 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 compounds of formulae U-1 to U-20

in which
L 1 , L 2 identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl, and
R U , X 1 , X 2 , Y 1 , Y 2 , Y 3 and Y 4 have the meanings given for formula U.

5. The compound according to claim 1 , wherein the radicals X 1 and X 2 denote H or F.

6. The compound according to claim 1 , wherein the radicals Y 1 , Y 2 , Y 3 , and Y 4 , identically or differently, denote H, F, Cl, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclopentenyl.

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

8. The compound according to claim 1 , wherein the group R U denotes R P .

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

10. The liquid crystal medium according to claim 9 , wherein the medium comprises one or more compounds selected from the group 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,

or

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—,

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

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C07C331/28 Primary

  having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C331/30

  containing at least two isothiocyanate groups bound to the same carbon skeleton · CPC title

• C09K19/0403 Primary

  the structure containing one or more specific, optionally substituted ring or ring systems · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title