Hoffmann-la Roche Inc.

Other

Arthur Boller

Martin Schadt

Hanspeter Scherrer

Alois Villiger

Richard Buchecker

Alfred Germann

Martin Petrzilka

Marco Cereghetti

Stephen Kelly

Hans-Jurgen Fromm

Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl, and their use for liquid crystalline mixtures and electro-optical purposes.

Halobenzene liquid crystals

A ferroelectric liquid crystal mixture containing at least one compound of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 represents a single covalent bond, --COO-- or --OOC-- and X.sup.2 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--; rings A.sup.1, A.sup.2 and A.sup.3 each independently signify 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl or pyrimidin-2,5-diyl, pyrazin-2,5-diyl, when n is 1, trans-1,4-cyclohexylene or trans-m-dioxan-2,5-diyl; with the proviso that one of the rings present stands for pyrimidin-2,5-diyl or pyrazin-2,5-diyl when a further ring signifies trans-1,4-cyclohexylene or when n stands for the number 0 and X.sup.1 stands for a single covalent bond; and R.sup.1 signifies an optionally halogen-substituted alkenyl group with up to 18 carbon atoms in which optionally 1 or 2 non-adjacent CH.sub.2 groups are replaced by --O-- and/or a C.dbd.C double bond; with the proviso that R.sup.1 is different from 3,7-dimethyl-6-octenyloxy; R.sup.2 signifies an optionally halogen-substituted alkyl group with up to 18 carbon atoms in which optionally 1 or 2 non-adjacent CH.sub.2 groups are replaced by --O-- and/or a C.dbd.C double bond; with the proviso that residues R.sup.1 and/or R.sup.2 attached to an aromatic ring have at least 2 chain atoms between the aromatic ring and a C.dbd.C double bond present; as well as novel compounds falling under formula I and novel ferroelectric liquid crystal devices employing the compounds according to the invention.

Liquid crystal compounds and indicating device employing same

Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently straight-chain C.sub.1 -C.sub.12 -alkyl or when positioned on an aromatic ring R.sup.1 and R.sup.2 may also independently be straight-chain C.sub.1 -C.sub.12 -alkoxy, or one of R.sup.1 and R.sup.2 may also be a group of the formula: ##STR2## X.sup.1 and X.sup.2 are independently single covalent bonds or one of X.sup.1 and X.sup.2 may also be --CH.sub.2 CH.sub.2 --; rings A.sup.1 and A.sup.2 are independently 1,4-phenylene or, when X.sup.1 or X.sup.2 is --CH.sub.2 CH.sub.2 --, rings A.sup.1 and A.sup.2 may also independently be trans-1,4-cyclohexylene; and R.sup.3 is straight-chain C.sub.1 -C.sub.12 -alkyl or when positioned on an aromatic ring R.sup.3 may also be straight-chain C.sub.1 -C.sub.12 -alkoxy. Their manufacture and use in liquid crystalline mixtures are described.

Dicyano compounds

Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or straight-chain alkyl; R.sup.2 is --CN, --R, --COR, --COOR or when R.sup.2 is positioned on an aromatic ring R.sup.2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; the six-membered rings in A and ring B each are 1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also is trans-2,5-disubstituted m-dioxane, 2,5-disubstituted pyrimidine or 3,6-disubstituted pyridazine, with the proviso that a maximum of two adjacent trans-1,4-cyclohexylene rings are linked directly via a single covalent bond; and m is the integer 2, or when ring B is trans-1,4-cyclohexylene or trans-2,5-disubstituted m-dioxane, m also can be the integer 0, their manufacture, liquid crystalline mixtures which contain these compounds as well as the use of these compounds for electro-optical purposes are described. Additionally, compounds of the formula ##STR2## wherein R.sup.8 is straight-chain C.sub.1 -C.sub.12 alkyl, their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes are described.

Cyclohexanecarbonitriles

Coloring substance-containing liquid crystal mixtures

Pyrimidines of the formula: ##STR1## wherein Y is nitrogen and Z is .dbd.CH--, or Z is nitrogen and Y is .dbd.CH--; R.sup.1 is alkyl and R.sup.2 is cyano, alkyl, p-alkylphenyl or trans-4-alkylcyclohexyl; where each alkyl denotes either a straight chain alkyl group of 1 to 12 carbon atoms or a branched chain alkyl group of the formula C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n, n is 1, 2 or 3; with the proviso that the compound contains at most only one of said branched chain alkyl group and with the further proviso that the sum of the carbon atoms in all of the alkyl groups within the compound is at most 14 are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.

Disubstituted pyrimidines

Liquid crystal mixtures containing a coloring substance which comprise about 5 to about 40 weight % of trans-p-[5-(4-alkylcyclohexyl)-2-pyrimidinyl]benzonitriles, about 10 to about 60 weight % of trans-4-alkylcyclohexane carboxylic acid phenyl esters and about 0.1 to about 15 weight % of one or more coloring substances of the formula ##STR1## wherein m stands for the number 1 and X is alkoxy and Y is nitro; or m stands for the number 1 or 2; and X is p-alkoxyphenyl and Y is nitro or dialkylamino, or X is alkoxy and Y is -p-nitrophenyl or -(dialkylamino)phenyl; or m stands for the number 2, and X is alkoxy and Y is alkoxy, nitro or dialkylamino, or both X and Y are dialkylamino; and wherein the alkoxy denotes a straight-chain group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms are described.

Liquid crystal mixtures

Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.

Hydrogenated naphthalenes

Pyrimidine derivatives of the formula ##STR1## wherein at least one of rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other, optionally, may be aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl group of the formula C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n -- wherein n is 1, 2 or 3, are described. Processes for the preparation of the compounds of formula I as well as their uses in liquid crystalline mixtures are also described.

Meterocyclic compounds

Liquid crystalline mixtures comprising trans-phenyldioxane, phenylpyrimidine and phenylbenzoate compounds which are useful in electro-optical apparatuses are disclosed.

Optically active pyrimidines of the formula ##STR1## wherein Z is --(CH.sub.2).sub.n -- or --(CH.sub.2).sub.n --O-- wherein n is an integer of 1 to 4 and each of the symbols X is a nitrogen atom and each of the symbols Y is --CH-- or each of the symbols Y is a nitrogen atom and each of the symbols X is --CH--, useful for electro-optical purposes, as well as liquid crystalline mixtures for electro-optical purposes containing compounds of the formula Ia and/or Ib, are described. The compounds of formulas Ia and Ib are useful for electro-optical purposes, for example, in electro-optical apparatuses.

Pyrimidine derivatives

Pyrimidine derivatives of the formula ##STR1## wherein at least one of rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other, optionally, may be aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl group of the formulas C.sub.2 H.sub.5 --CH(CH.sub.3)--(CH.sub.2).sub.n --wherein n is 1, 2 or 3, are described. Processes for the preparation of the compounds of formula I as well as their uses in liquid crystalline mixtures are also described.

Heterocyclic compounds

Liquid crystal mixtures having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60.degree. C., one or more compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or straight-chain alkyl, provided that at least one of R.sub.1 and R.sub.2 is other than hydrogen and that R.sub.1 and R.sub.2 together contain no more than 9 carbon atoms, and, if desired, one or more additional doping agents, are described.

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Binningen, Switzerland

Arthur Boller