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US 5,820,785 AGranted
Fluoroalkylethnyl- and difluoroalkylethynylbenzenes, and their use in liquid-crystal mixtures
AssigneeMerck Patent GmbH
InventorsHubert Schlosser, Dietmar Jungbauer
Life of this patent
Estimating the term…
Abstract
Disclosed are derivatives of fluoroalkylethynyl- and difluoroalkylethynylbenzenes of the formula (I) herein. These compounds exhibit useful properties as liquid crystal compounds and are useful in nematic liquid crystal mixtures.
Claims21
A fluoroalkylethynyl- or difluoroalkylethynyl- benzene compound of the formula (I) ##STR76## wherein:
- R.sup.1 is H, a straight-chain or branched (with or without an asymmetric carbon atom) alkyl group having 1 to 15 carbon atoms, in which one or two non-adjacent CH.sub.2 groups are optionally replaced by --O--, --S--, --CO--, --CO--l--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.--CH--, --C.tbd.C--, cyclopropane-1,2-diyl or --Si(CH.sub.3).sub.2 --, and in which one or more H atoms in the alkyl group are optionally replaced by F, Cl or CN;
- A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, pyrazine-2,5-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, in which one or two H atoms are optionally replaced by F, or trans-1,4-cyclohexylene, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, bicyclo2.2.2!octane-1,4-diyl or 1,3-dioxoborinane-2,5-diyl;
- M.sup.1, M.sup.2 and M.sup.3 are identical or different and are each --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --O--, --O--CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CO--O--, --O--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O-- or --O--CO--;
- k, l, m, n, o and p are zero or one, with the proviso that the sum k+m+o is greater than zero;
- X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are, independently of one another, H, F or Cl;
- and
- Y is --CH.sub.2 F or --CHF.sub.2.
4 more elements
A fluoroalkylethynyl- or difluoroalkylethynyl- benzene compound of one of the following formulae:
- ##STR78## in which R.sup.1 is H, a straight-chain or branched (with or without an asymmetric carbon atom) alkyl group having 1 to 15 carbon atoms, in which one or two non-adjacent CH.sub.2 groups are optionally replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, cyclopropane-1,2-diyl or --Si(CH.sub.3).sub.2 --, and in which one or more H atoms in the alkyl group are optionally replaced by F, Cl or CN;
- Y is --CH.sub.2 F or --CHF.sub.2, and L.sup.1 and L.sup.2 are each, independently of one another, H or F.
A fluoroalkylethynyl- or difluoroalkylethynyl- benzene compound of the formula (I) ##STR79## wherein:
- R.sup.1 is H, a straight-chain or branched (with or without an asymmetric carbon atom) alkyl group having 1 to 15 carbon atoms, in which one or two non-adjacent CH.sub.2 groups are optionally replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, cyclopropane-1,2-diyl or --Si(CH.sub.3).sub.2 --, and in which one or more H atoms in the alkyl group are optionally replaced by F, Cl or CN;
- A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, pyrazine-2,5-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, in which one or two H atoms are optionally replaced by F, or trans-1,4-cyclohexylene, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, bicyclo2.2.2!octane-1,4-diyl or 1,3-dioxoborinane-2,5-diyl;
- M.sup.1, M.sup.2 and M.sup.3 are identical or different and are each --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.--C--, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --O--, --O--CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CO--O--, --O--CO--CH.sub.2 CH.sub.2 --, --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O-- or --O--CO--;
- k, l, m, n, o and p are zero or one, with the proviso that the sum k+m+o is greater than zero;
- X.sup.1 and X.sup.3 are, independently of one another, H;
- X.sup.2 and X.sup.4 are independently of one another, F;
- and
- Y is --CHF.sub.2.
5 more elements
Dependencies are inferred from the claim text.