US 5,399,292 A · Fluoro-substituted phenyl-cyclohexylacetylenes

Abstract

Fluoro-substituted phenyl-cyclohexylacetylenes have the formula: ##STR1## wherein R signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group can be replaced by oxygen and/or one or more hydrogen atoms can be replaced by fluorine atoms, with the proviso that two oxygen atoms are not directly adjacent; A.sup.1 represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; A.sup.2 signifies trans-1,4-cyclohexylene or 1,4-phenylene which is optionally substituted with fluorine; Z.sup.1 signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--; Z.sup.2 signifies a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--; n signifies 0 or 1; m signifies 0 or 1, with the proviso that n+m is <1; and X signifies cyano, --CF.sub.3, --OCF.sub.3, --OCHF.sub.2, --CH.dbd.CF.sub.2, --CH.dbd.CHCl, alkyl, alkenyl, alkoxy, alkenyloxy or alkoxyalkyl with 1 or, respectively, 2 to 6 carbon atoms or on trans-1,4-cyclohexylene also --CH.dbd.CHF or --CH.dbd.CHCl or on 1,4-phenylene also fluorine or chlorine.

Claims29

Dependent claims

A compound of the formula:

##STR9## wherein R is an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent;
A.sup.1 is 1,4-phenylene, or pyridine-2,5-diyl, or pyrimidine-2,5-diyl, or trans-1,4-cyclohexylene, or trans-1,3-dioxane-2,5-diyl;
A.sup.2 is trans-1,4-cyclohexylene, or unsubstituted 1,4-phenylene, or fluorine substituted 1,4-phenylene;
Z.sup.1 is a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 is a saturated ring, the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
Z.sup.2 is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, or the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
n is 0 or 1;
m is 0 or 1, provided that n+m is .ltoreq.1;
and
X is cyano, --CF.sub.3, --OCF.sub.3, --OCHF.sub.2, --CH.dbd.CF.sub.2, --CH.dbd.CHCl, or an unsubstituted alkyl, alkenyl, alkoxy, alkenyloxy or alkoxyalkyl of 6 or less carbon atoms, additionally when A.sup.2 is trans-1,4-cyclohexylene, X can also be --CH.dbd.CHF or --CH.dbd.CHCl, and when A.sup.2 is 1,4-phenylene, X can also be fluorine or chlorine.

6 more elements

A liquid crystalline mixture containing at least two components, wherein at least one component is:

##STR21## wherein R is an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which at least one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent;
A.sup.1 is 1,4-phenylene, or pyridine-2,5-diyl, or pyrimidine-2,5-diyl, or trans-1,4-cyclohexylene, or trans-1,3-dioxane-2,5-diyl;
A.sup.2 is trans-1,4-cyclohexylene, or unsubstituted 1,4-phenylene, or fluorine substituted 1,4-phenylene;
Z.sup.1 is a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 is a saturated ring, the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
Z.sup.2 is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, or the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
n is 0 or 1;
m is 0 or 1, provided that n+m is .ltoreq.1;
and
X is cyano, --CF.sub.3, --OCF.sub.3, --OCHF.sub.2, --CH.dbd.CF.sub.2, --CH.dbd.CHCl, or an unsubstituted alkyl, alkenyl, alkoxy, alkenyloxy or alkoxyalkyl of 6 or less carbon atoms, additionally when A.sup.2 is trans-1,4-cyclohexylene, X can also be --CH.dbd.CHF or --CH.dbd.CHCl, and when A.sup.2 is 1,4-phenylene, X can also be fluorine or chlorine.

6 more elements

An electro-optical cell comprising:

(a) two plate means;
(b) liquid crystal means disposed between the two plate means and including a compound of the formula:
##STR23## wherein R is an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or an unsubstituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms, or a fluorine substituted alkyl, alkoxy, alkenyl or alkenyloxy of 12 or less carbon atoms in which one CH.sub.2 group is replaced with oxygen, provided that no two oxygen atoms are directly adjacent;
A.sup.1 is 1,4-phenylene, or pyridine-2,5-diyl, or pyrimidine-2,5-diyl, or trans-1,4-cyclohexylene, or trans-1,3-dioxane-2,5-diyl;
A.sup.2 is trans-1,4-cyclohexylene, or unsubstituted 1,4-phenylene, or fluorine substituted 1,4-phenylene;
Z.sup.1 is a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 is a saturated ring, the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
Z.sup.2 is a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, or the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;
n is 0 or 1;
m is 0 or 1, with the proviso that n+m is .ltoreq.1;
and
X is cyano, --CF.sub.3, --OCF.sub.3, --OCHF.sub.2, --CH.dbd.CF.sub.2, --CH.dbd.CHCl, or an unsubstituted alkyl, alkenyl, alkoxy, alkenyloxy or alkoxyalkyl of 6 or less carbon atoms, additionally when A.sup.2 is trans-1,4-cyclohexylene, X can also be --CH.dbd.CHF or --CH.dbd.CHCl, and when A.sup.2 is 1,4-phenylene, X can also be fluorine or chlorine;
and
(c) means for applying an electric potential to the plate means.

10 more elements

Dependencies are inferred from the claim text.

Fluoro-substituted phenyl-cyclohexylacetylenes

Life of this patent

Fluoro-substituted phenyl-cyclohexylacetylenes

Life of this patent

Abstract

Claims29