US 5,849,216 AGranted

Compounds for use in liquid-crystal mixtures

AssigneeHoechst Aktiengesellschaft

InventorsGerd Illian, Anke Kaltbeitzel, Rainer Wingen, Hubert Schlosser

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Abstract

Compounds of the formula (I) R.sup.1 --(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.g --H(I) in which the symbols and indices have the following meanings: R.sup.1 is B or a straight-chain or branched alkyl radical having 1 to 22 carbon atoms (with or without an asymmetrical carbon atom) in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, and in which, in addition, one or more hydrogen atoms of the alkyl radical may be substituted by F, Cl, Br or CN, or is a chiral group, for example an epoxide, a dioxolane or a cyclic lactone, --(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.g -- is a system comprising 1 to 4 rings (cyclohexane, aromatic or heterocyclic), it being possible for the system to be linked in different ways. The compounds according to the invention increase the response speed of liquid-crystal mixtures.

Claims7

Dependent claims

A method for producing ferroelectric liquid-crystal mixtures, which comprises adding 0.01 to 60% by weight of one or more compounds of the formula (I)

R.sup.1 --(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.g --H(I)
in which the symbols and indices have the following meanings:
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 22 carbon atoms (with or without an asymmetrical carbon atom) in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, and in which, in addition, one or more hydrogen atoms of the alkyl radical may be substituted by F, Cl, Br or CN, or is one of the chiral groups below:
##STR38## R.sup.2, R.sup.3, R.sup.4 and R.sup.5, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 22 carbon atoms in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, or R.sup.2 and R.sup.3 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system;
A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are identical or different and are 1,4-phenylene, in which one or two hydrogen atoms may be replaced by F, Cl and/or CN, pyrazine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, in which one or two hydrogen atoms may be replaced by F, trans-1,4-cyclohexylene, in which one or two hydrogen atoms may be replaced by --CN and/or --CH.sub.3, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl, 1,3-thiazole-2,4-diyl, 1,3-thiazole-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, piperazine-1,4-diyl, piperazine-2,5-diyl, naphthalene-2,6-diyl, bicyclo2.2.2!octane-1,4-diyl, 1,3-dioxaborinane-2,5-diyl or trans-decalin-2,6-diyl;
M.sup.1, M.sup.2 and M.sup.3 are identical or different and are --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--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--;
M.sup.4 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO-- or a single bond;
a, b, c, d, e and f are zero or one, with the proviso that the sum a+c+e+g is 1, 2, 3 or 4, g is one and
* is a chiral center;
to one or more compounds having nematic, cholesteric and/or smectic phases.

7 more elements

A ferroelectric liquid-crystal mixture comprising one or more compounds of the formula (I)

R.sup.1 --(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.g --H(I)
in which the symbols and indices have the following meanings:
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 22 carbon atoms (with or without an asymmetrical carbon atom) in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, and in which, in addition, one or more hydrogen atoms of the alkyl radical may be substituted by F, Cl, Br or CN, or is one of the chiral groups below:
##STR39## R.sup.2, R.sup.3, R.sup.4 and R.sup.5, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 22 carbon atoms in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, or R.sup.2 and R.sup.3 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system;
A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are identical or different and are 1,4-phenylene, in which one or two hydrogen atoms may be replaced by F, Cl and/or CN, pyrazine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, in which one or two hydrogen atoms may be replaced by F, trans-1,4-cyclohexylene, in which one or two hydrogen atoms may be replaced by --CN and/or --CH.sub.3, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl, 1,3-thiazole-2,4-diyl, 1,3-thiazole-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl, piperazine-1,4-diyl, piperazine-2,5-diyl, naphthalene-2,6-diyl, bicyclo2.2.2!octane-1,4-diyl, 1,3-dioxaborinane-2,5-diyl or trans-decalin-2,6-diyl;
M.sup.1, M.sup.2 and M.sup.3 are identical or different and are --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--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--;
M.sup.4 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO--, or a single bond;
a, b, c, d, e and f are zero or one, with the proviso that the sum a+c+e+g is 1, 2, 3 or 4, g is one and
* is a chiral center.

6 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/454,995Filed 31 May 1995 · continuation
Priority: DE 41 36 627.17 Nov 1991
Granted: 15 Dec 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
C07C 69/92
Of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic…
C07D 239/26
Having three or more double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms, hydrocarbon or…
C07D 239/34
One oxygen, sulfur or nitrogen atom: one oxygen atom