Aromatic isothiocyanates
The present invention relates to aromatic isothiocyanates of formula U as 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.
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 , wherein the medium comprises one or more compounds selected from the group consisting of 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, and
R 1 ,
have the meanings given for formula I.
11. The liquid crystal medium according to claim 9 , wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae II-1 to II-3
in which
R 2 ,
have the meanings given for formula II.
12. The liquid crystal medium according to claim 9 , wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae III-1 to III-6
in which
R 3 ,
have the meanings given for formula III, and
Z 31 and Z 32 independently of one another, denote trans-CH═CH— or trans-CF═CF—, and in formula III-6 alternatively one of Z 31 and Z 32 may denote —C≡C—.
13. A component for high-frequency technology, comprising the liquid crystal medium according to claim 8 .
14. The component according to claim 13 , which is a liquid-crystal based antenna element, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network or a varactor.
15. A microwave antenna array, comprising one or more components according to claim 13 .
16. A compound selected from the group consisting of compounds 1 to 50
1
1,2,4,5-Tetrafluoro-3-isothiocyanato-6-[4-(4-
propylcyclohexyl)phenyl]benzene
2
1,2,4,5-Tetrafluoro-3-isothiocyanato-6-[4-[4-
(trifluoromethoxy)phenyl]phenyl]benzene
3
1-[4-[2-(4-Butylphenyl)ethynyl]phenyl]-2,3,5,6-tetrafluoro-4-
isothiocyanato-benzene
4
1,2,4,5-Tetrafluoro-3-isothiocyanato-6-[4-[2-[4-
(trifluoromethoxy)phenyl]ethynyl]phenyl]benzene
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
17. A liquid crystal medium comprising one or more compounds according to claim 16 .
18. The liquid crystal medium according to claim 17 , 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,
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
19. A component for high-frequency technology, comprising the liquid crystal medium according to claim 17 .
20. The component according to claim 19 , which is a liquid-crystal based antenna element, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network, a varactor, or a microwave antenna array.