Patent ID: 6171519
Filing Date: 2001-01-09
Classification: C07D,C09K

Abstract:
A ferroelectric liquid crystal mixture comprising at least two compounds selected from at least two different of the following groups of compounds including two more compounds from at least groups B and C:A. (1,3,4)-Thiadiazole derivatives of the formula (I): ##STR73##wherein the symbols and indices have the following meanings:R.sup.1 and R.sup.2 independently of one another, are(a) a hydrogen atom,(b) a straight-chain or branched-chain alkyl group, with or without an asymmetric carbon atom, having from 2 to 16 carbon atoms, in which one or two --CH.sub.2 -- groups may be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CH.dbd.CH--, --C.tbd.C--, --Si(CH.sub.3).sub.2 --, 1,4-cyclohexylene, 1,4-phenylene, cyclopropane-1,2-diyl or --O--CO--O--, with the proviso that --O-- and/or --S-- atoms must not be directly bonded to one another; one or more hydrogen atoms of the alkyl group may be substituted by F, Cl, CN and/or CF.sub.3 ; or(c) any one of the following chiral groups: ##STR74##wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, independently of one another, are a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), where one or more --CH.sub.2 -- groups may also be replaced by --O-- or --CH.dbd.CH--, with the proviso that oxygen atoms must not be bonded directly to one another; one or more hydrogen atoms of the alkyl group may be substituted by --F or --Cl; or R.sup.4 and R.sup.5 may also together be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded to an oxirane, dioxolane or tetrahydrofuran system;Q is --CH.sub.2 --O--, --CO--O-- or a single bond;Z.sup.1, Z.sup.2 and Z.sup.3 independently of one another, are a single bond, --O--, --CO--O-- or --O--CO--; with the proviso that, when R.sup.1 is (c), then Z.sup.1 is not a single bond, and that, when R.sup.2 is (c), then Z.sup.2 is not a single bond;A.sup.1 and A.sup.2 are identical or different and are 1,4-phenylene, in which one or more H atoms may be replaced by F, pyridine-2,5-diyl, in which one H atom may be replaced by F, pyrimidine-2,5-diyl or trans-1,4-cyclohexylene;a and b are 0 or 1 and a+b is 0 or 1;X.sup.1 and X.sup.2 independently of one another, are --N--, --CF-- or --CH--;B. Phenanthrene derivatives of the formula (II), ##STR75##in which the symbols and indices have the following meanings:E.sup.1, E.sup.2, E.sup.3, E.sup.4, E.sup.5 and E.sup.6 are --N--, --CF-- or --CH--, with the following provisos:if E.sup.1 (E.sup.4) is --N-- or --CF--, E.sup.2 and E.sup.3 (E.sup.5 and E.sup.6) must be --CH--;if E.sup.2 and/or E.sup.3 (E.sup.5 and/or E.sup.6) are --CF--, E.sup.1 (E.sup.4) must be --CH--;if E.sup.2 (E.sup.5) is --N--, E.sup.1 (E.sup.4) must be --CH--, while E.sup.3 (E.sup.6) can be --CH-- or --CF--; andat least one of E.sup.1 to E.sup.6 must be --N-- or --CF--;G is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--;R.sup.1 and R.sup.2, independently of one another, are hydrogen or a straight-chain or branched-chain alkyl group having from 1 to 20 carbon atoms (with or without an asymmetrical carbon atom), in which one or more --CH.sub.2 -- groups may be replaced by --O--, --CO--O--, --O--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, cyclopropane-1,2-diyl, --Si(CH.sub.3).sub.2 --, 1,4-phenylene, trans-1,4-cyclohexylene or trans-1,3-cyclopentylene, with the proviso that oxygen atoms and/or sulfur atoms must not be bonded directly to one another; one or more hydrogen atoms of the alkyl group may be substituted by --F, --Cl, --Br, --CF.sub.3, --CN or --OR.sup.3 ; or R.sup.1, R.sup.2 are one of the following chiral groups: ##STR76##wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, independently of one another, are a straight-chain or branched-chain alkyl group having from 1 to 6 carbon atoms (with or without an asymmetrical carbon atom), where one or more --CH.sub.2 -- groups may also be substituted by --O-- or --CH.dbd.CH--, with the proviso that oxygen atoms must not be bonded directly to one another; one or more hydrogen atoms of the alkyl group may be substituted by --F or --Cl; or R.sup.4 and R.sup.5 may also together be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded to an oxirane, dioxolane or tetrahydrofuran system;Q is --CH.sub.2 --O--, --CO--O-- or a single bond;M.sup.1 and M.sup.2, independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --C.tbd.C-- or a single bond;A.sup.1 and A.sup.2, independently of one another, are 1,4-phenylene in which one or more hydrogen atoms may be substituted by F, Cl and/or CN, pyrazine-2,5-diyl pyridazine-3,6-diyl, pyridine-2,5-diyl in which one or more hydrogen atoms may be substituted by F, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene in which one or two hydrogen atoms may be substituted with CN and/or CH.sub.3 ;n and m are 0 or 1, and the sum of n+m is 0 or 1;C. 2-Fluoropyridine derivatives of the formula (III), ##STR77##in which the symbols and indices have the following meanings:R.sup.1 and R.sup.2, independently of one another, are hydrogen or a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), in which one or two non-adjacent --CH.sub.2 -- groups may be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, cyclopropane-1,2-diyl or --Si(CH.sub.3).sub.2 --; one or more hydrogen atoms of the alkyl group may be substituted by F, Cl, CN and/or CF.sub.3 ; or R.sup.1, R.sup.2 are one of the following chiral groups: ##STR78##wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, independently of one another, are a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), where one or more --CH.sub.2 -- groups may also be substituted by --O-- or --CH.dbd.CH--, with the proviso that oxygen atoms must not be bonded directly to one another; one or more hydrogen atoms of the alkyl group may be substituted by --F or --Cl; or R.sup.4 and R.sup.5 may also together be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded to an oxirane, dioxolane or tetrahydrofuran system;Q is --CH.sub.2 --O--, --CO--O-- or a single bond;A.sup.1, A.sup.2, A.sup.3 and A.sup.4, independently of one another, are 1,4-phenylene in which one or two hydrogen atoms may be substituted by F, or pyrazine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, trans-1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN, or naphthalene-2,6-diyl; M.sup.1, M.sup.2, M.sup.3 and M.sup.4, independently of one another, are --O--, --S--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C-- with the proviso that two M groups must not be directly bonded to one another; k, l, m, n, o, p, q and r are 0 or 1, with the proviso that the sum of k+m+p+r is more than 0 and less than 4;D. Phenylene derivatives of the formula (IV), ##STR79##wherein R.sup.1 and R.sup.2, independently of one another, are hydrogen or a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), in which one or two non-adjacent --CH.sub.2 -- groups may be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-Cyclohexylene or --Si(CH.sub.3).sub.2 --; and one or more hydrogen atoms of the alkyl group may be substituted with F, Cl, CN and/or CF.sub.3 ; or R.sup.1, R.sup.2 are one of the following chiral groups: ##STR80##wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7, independently of one another, are a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), where one or more --CH.sub.2 -- groups may also be substituted by --O-- or --CH.dbd.CH--, with the proviso that oxygen atoms must not be bonded directly to one another; one or more hydrogen atoms of the alkyl group may be substituted by --F or --Cl; or R.sup.4 and R.sup.5 may also together be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded to an oxirane, dioxolane, or tetrahydrofuran system;Q is --CH.sub.2 --O--, --CO--O-- or a single bond;A.sup.1, A.sup.2, A.sup.3 are, independently of one another, 1,4-phenylene in which one two H-atoms may be substituted by F, pyridin-2,5-diyl, pyrimidin-2,5-diyl, pyrazine-2,5-diyl, pyridazin-3,6-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronapthalene-2,6-diyl or 1,4-cyclohexylene in which one or two hydrogenatoms may be substituted by CN and/or CH.sub.3 groups;X.sup.1 and X.sup.2 are selected from hydrogen, F, Cl, CF.sub.3 and CN; with the proviso that X.sup.1 and X.sup.2 are not simultaneously hydrogen;each of Z.sup.1 and Z.sup.2 are --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --O--CH.sub.2 --, --CH.sub.2 --O--, --C.tbd.C-- or a single bond;each k, m and n are 0, 1 or 2, and (k,m+n) is 1 or 2; andE. Meta-substituted aromatic compounds of the formula (V), ##STR81##wherein X.sup.3 is F, Cl, Br, CN, CF.sub.3 or an alkyl group having from 1 to 12 carbon atoms, in which one or two CH.sub.2 -group may be replaced by --O--, --CO--O-- or --O--CO--, and in which one or more hydrogen atoms in the alkyl group may be substituted by F, Cl or CN;R.sup.1 is hydrogen or a straight-chain or branched-chain alkyl group having from 1 to 16 carbon atoms (with or without an asymmetrical carbon atom), in which one or more hydrogen atoms may be substituted by F, Cl, CN and/or CF.sub.3 ;A.sup.1, A.sup.2 and A.sup.3, independently of one another, are 1,4-phenylene in which one or two hydrogen atoms may be substituted by F, or pyrazine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, trans-1,4-cyclohexylene in which one or two hydrogen atoms may be substituted by CN, or 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or 1,3-thiazole-2,4(5)-diyl;M.sup.1, M.sup.2, M.sup.3 and M.sup.4, independently of one another, are --O--, --S--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, with the proviso that two M groups must not be bonded directly to one another;k, l, m, n, o, p and q are 0 or 1, with the proviso that the sum of l+n+p is more than 0 and less than 4.