US 5,851,425 AGranted

Imidazothiazoles

AssigneeRolic AG

InventorsRichard Buchecker, Willy Friedrichsen, Jurg Funfschilling, Sandra Lupfert

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Abstract

Compounds of the general formula ##STR1## have a pronounced tendency to form liquid crystalline S (smectic) phases. Thus, optically inactive compounds of the formula I also have a tilted smectic phase, in particular an S.sub.C phase, in addition to a nematic phase. In contrast, many optically active compounds of the formula I additionally have, inter alia, a tilted smectic chiral phase, in particular a chiral S.sub.C phase, in addition to a cholesteric phase. The stated compounds are therefore particularly suitable as components and as dopants, respectively, for the preparation of a very wide range of liquid crystalline mixtures. The class of compounds comprising compounds of the general formula I offers a broad range of novel components and mixtures for optimization and modification of liquid crystalline mixtures.

Claims15

Dependent claims

An imidazothiazole derivative of the formula ##STR7## in which the symbols m, n, R.sup.1 and R.sup.2 have the following meanings:

m and n are 0 or 1, with the proviso that m+n=1 or 2
R.sup.1 is R.sup.3 or Q.sup.1 or, if n is 0 and m is 1, also R.sup.3 -A.sup.3 -Z.sup.3 -,
R.sup.2 is R.sup.4 or Q.sup.2 or, if n is 1 and m is 0, also R.sup.4 -A.sup.4 -Z.sup.4,
and, independently of one another,
R.sup.3 and R.sup.4 are each on alkenyl or alkenyl radical incorporating at least three carbon atoms in which one methylene group or a plurality of non-neighboring methylene groups are optionally replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms are replaced by fluorine or chlorine,
Q.sup.1 and Q.sup.2 are each one of the following chiral groups ##STR8## in which R.sup.5 and R.sup.6 are each an alkyl or alkenyl radical in which one methylene group or a plurality of non-neighbouring methylene groups may be replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms may be replaced by fluorine or chlorine, with the proviso that the oxygen atoms are not linked directly to the ring in Q.sup.1 or Q.sup.2,
A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are trans-1,4-cyclohexylene or are 1,4-phenylene which is unsubstituted or monosubstituted or disubstituted by fluorine, chlorine, cyano or methyl, and
Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are each a single bond, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 --, --CH.sub.2 --O--, --COO--, --OOC--, --C.ident.C--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --CH.dbd.CH--CH.sub.2 O--, --OCH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 --CH.dbd.CH--.

5 more elements

A liquid crystalline mixture having at least two components, comprising a content of at least one imidazothiazole derivative of the formula ##STR10## in which the symbols m, n, R.sup.1 and R.sup.2 have the following meanings:

m and n are 0 or 1,
R.sup.1 is R.sup.3 or Q.sup.1 or, if n is 0 and m is 1, also R.sup.3 -A.sup.3 -Z.sup.3 -,
R.sup.2 is R.sup.4 or Q.sup.2 or, if n is 1 and m is 0, also R.sup.4 -A.sup.4 -Z.sup.4 -,
and, independently of one another,
R.sup.3 and R.sup.4 are each an alkyl or alkenyl radical in which one methylene group or a plurality of non-neighbouring methylene groups are optionally replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms are replaced by fluorine or chlorine,
Q.sup.1 and Q.sup.2 are each one of the following chiral groups ##STR11## in which R.sup.5 and R.sup.6 are each an alkyl or alkenyl radical in which one methylene group or a plurality of non-neighbouring methylene groups may be replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms may be replaced by fluorine or chlorine, with the proviso that the oxygen atoms are not linked directly to the ring in Q.sup.1 or Q.sup.2,
A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are trans-1,4-cyclohexylene or are 1,4-phenylene which is unsubstituted or monosubstituted or disubstituted by fluorine, chlorine, cyano or methyl, and
Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are each a single bond, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 --, --CH.sub.2 --O--, --COO--, --OOC--, --C.ident.C--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --,--CH.dbd.CH--CH.sub.2 O--, --OCH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 --CH.dbd.CH--.

5 more elements

An imidazothiazole derivative of the formula ##STR15## which is optically active and in which the symbols m, n, R.sup.1 and R.sup.2 have the following meanings:

in which the symbols m, n, R.sup.1 and R.sup.2 have the following meanings:
m and n are 0 or 1,
R.sup.1 is R.sup.3 or Q.sup.1 or, if n is 0 and m is 1, also R.sup.3 -A.sup.3 -Z.sup.3 -,
R.sup.2 is R.sup.4 or Q.sup.2 or, if n is 1 and m is 0, also R.sup.4 --A.sup.4 --Z.sup.4 --,
and, independently of one another,
R.sup.3 and R.sup.4 are each an alkyl or alkenyl radical in which one methylene group or a plurality of non-neighbouring methylene groups are optionally replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms are replaced by fluorine or chlorine,
Q.sup.1 and Q.sup.2 are each one of the following chiral groups ##STR16## in which R.sup.5 and R.sup.6 are each an alkyl or alkenyl radical in which one methylene group or a plurality of non-neighbouring methylene groups may be replaced by --O--, --COO-- or --OOC--, and/or one hydrogen atom or a plurality of hydrogen atoms may be replaced by fluorine or chlorine, with the proviso that the oxygen atoms are not linked directly to the ring in Q.sup.1 or Q.sup.2,
A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are trans-1,4-cyclohexylene or are 1,4-phenylene which is unsubstituted or monosubstituted or disubstituted by fluorine, chlorine, cyano or methyl, and
Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are each a single bond, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 --, --CH.sub.2 --O--, --COO--, --OOC--, --C.ident.--C--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --,--CH.dbd.CH--CH.sub.2 --O--, --OCH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 --CH.dbd.CH--.

6 more elements

Dependencies are inferred from the claim text.