Hoffmann-la Roche Inc.

Rolic Ag

Stephen Kelly

Martin Schadt

Richard Buchecker

Frans Leenhouts

Hans-Jurgen Fromm

Alois Villiger

Klaus Schmitt

Jurg Funfschilling

Arthur Boller

Andreas Schuster

Alfred Germann

Rolf-Peter Herr

Teodor Luk Ac

The present invention is concerned with optically active, ferroelectric, smectic, photo-cross linkable compounds of the formula ##STR1## wherein A.sup.1 and A.sup.2 may both signify residues of the formula ##STR2## and be the same or different, while A.sup.3 may signify a residue of the formula ##STR3## as well as liquid crystalline mixtures which contain such compounds and their use in the cross-linked state in optical components.

Optically active smectic photo-cross-linkable liquid crystals

Chiral dopants of the formula ##STR1## in which n represents the number 0 or 1; R.sup.3 denotes a group of the general formula ##STR2## A.sup.1, A.sup.2 and A.sup.3, independently of one another, represent 1,4-phenylene which is unsubstituted or substituted by halogen, cyano and/or methyl and in which 1 or 2 CH groups may be replaced by nitrogen, or represent trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl or naphthalene-2,6-diyl, and ring A.sup.2 additionally represents 1,4-biphenylene; Z.sup.1 and Z.sup.4, independently of one another, denote a single covalent bond or --CH.sub.2 CH.sub.2 --; Z.sup.2 and Z.sup.3, independently of one another, denote a single covalent bond, --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --C.tbd.C--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans-form of --CH.dbd.CH--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --O-- or --O--CH.sub.2 --CH.dbd.CH--; with the proviso that, if R.sup.3 denotes a group of the formula II, at least one of the groups Z.sup.2 and Z.sup.3 denotes --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 --O--, --O--(CH.sub.2).sub.3 -- or the trans-form of --CH.dbd.CH--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --O-- or --O--CH.sub.2 --CH.dbd.CH--; R.sup.1, R.sup.5 and R.sup.6 denote hydrogen, alkyl, phenyl or alkoxycarbonyl; R.sup.2 denotes alkyl, phenyl or alkoxycarbonyl; R.sup.4 denotes halogen, cyano, trifluoromethyl, trifluoromethoxy or alkyl in which one --CH.sub.2 --CH.sub.2 -- may be replaced by --CH.dbd.CH-- and/or one or two non-adjacent methylene groups may be replaced by --O--, --COO-- and/or --OOC-- and/or one methylene group methylene group may be replaced by --CHX--; X denotes halogen, cyano or methyl; and the dioxolane ring shown in the formula I is in optically active form, liquid-crystalline mixtures which contain such dopants, and their use for optical and electrooptical purposes.

Chiral dioxolanes

The present invention is related to photochemically polymerizable liquid crystals of the general formula ##STR1## wherein A.sup.1, A.sup.2 and A.sup.3 are, independently, photochemically polymerizable mesogenic residues. The present invention also provides liquid crystalline mixtures which contain these compounds, as well as use of these compounds in the cross-linked state as optical or electronic components.

Photochemically polymerizable liquid crystals

The present invention is concerned with photo cross-linkable liquid crystals of the formula ##STR1## wherein A is a cross-linkable mesogenic residue;

Photo cross-linkable liquid crystals

The invention is concerned with linear and cyclic polymers or oligomers having a photoreactive ethene group. The polymers are of the formula ##STR1## wherein M.sub.a, M.sub.b, M.sub.c are monomer units for homo- or copolymers;

Linear and cyclic polymers or oligomers having a photoreactive ethene

Compounds containing a 4-[(E)-alk-2-enoyloxy]benzoate group and liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures in electro-optical indicating devices. The compounds are of the formula ##STR1## wherein R.sup.1 is alkyl with 1 to 12 carbon atoms;

Substituted phenyl 4-[(E)-alk-2-enoyloxy]benzoates

Optically active dopants of the formula ##STR1## wherein A represents an optically active group selected from 1,1'-binaphthyl-2,2'-diyl, --CHR.sup.1 --CHR.sup.2 -- or --CH(COOR.sub.3)--CH(COOR.sub.4)--; Z denotes a group --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 -- or the trans form of --OCH.sub.2 --CH.dbd.CH--; R is hydrogen, methyl, phenyl or cyclohexyl; R.sup.2 is methyl, phenyl or cyclohexyl; R.sup.3 and R.sup.4 denote alkyl; Y stands for --CO-- or --CH.sub.2 --; ring B represents 1,4-phenytene or trans-1,4-cyclohexylene; and R is hydrogen, alkyl, alkoxy or cyano, liquid crystalline mixtures which contain such dopants and their use for optical and electro-optical purposes.

Chiral dopants for liquid crystalline mixtures

Compounds of the general formula ##STR1## wherein R.sup.1 signifies alkyl or alkenyl with 1 to 12 and, respectively, 2 to 12 carbon atoms, which is unsubstituted or mono- or multiply-substituted with halogen and in which one methylene group can be replaced by --O--;

Aromatic esters and liquid crystal mixtures containing same

Compounds having the Formula: ##STR1## wherein R.sup.1 denotes an alkenyl group; A.sup.1 and A.sup.2 each independently represent 1,4-phenylene, which is unsubstituted or substituted with halogen and in which, when it is unsubstituted, optionally 1 or 2 CH group(s) is/are replaced by nitrogen, or trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; Z.sup.1 and Z.sup.2 each independently signify a single covalent bond, --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O--, --C.dbd.C--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or the trans form of --OCH.sub.2 CH.dbd.CH--, --CH.dbd.CHCH.sub.2 O--, --(CH.sub.2).sub.2 CH.dbd.CH-- or --CH.dbd.CH(CH.sub.2).sub.2 --; n is either 0, 1 or 2; and R.sup.2 is halogen, cyano or alkyl with 1 to 12 carbon atoms, which is optionally substituted with fluorine and in which optionally 1 --CH.sub.2 -- group or 2 non-adjacent --CH.sub.2 -- groups is/are replaced by oxygen, --COO--, --OOC--, --CO-- and/or a --CH.sub.2 --CH.sub.2 -- group is replaced by --CH.dbd.CH--, are useful in electro-optical applications. Liquid crystalline mixtures containing such compounds are especially suitable for use in commercial applications, such as electro-optic cells.

Cyclohexyl alkenoate compounds

Compounds of the formula ##STR1## wherein R.sup.1 signifies a straight-chain alkyl group with 7 to 9 carbon atoms; and R.sup.2 represents a straight-chain alkyl group with 6 to 11 carbon atoms. their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes.

Phenylpyridine derivatives and liquid crystalline mixtures containing

Optically active compounds of the general formula ##STR1## wherein n stands for the number 0 or 1; R.sup.3 denotes a group R.sup.4 or a group of the general formula ##STR2## A.sup.1, A.sup.2 and A.sup.3 each independently represent 1,4-phenylene, which is unsubstituted or mono- or multiply-substituted with halogen, cyano and/or methyl and in which, where it is unsubstituted, 1 or 2 CH groups is/are optionally replaced by nitrogen, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, bycyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1 and Z.sup.4 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --; Z.sup.2 and Z.sup.3 each independently denote a single covalent bond, --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --C.tbd.C--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 -- or the trans form of --CH.dbd.CH--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--; R.sup.1 and R.sup.5 each independently signify alkyl with 1 to 12 carbon atoms, alkoxymethyl with 2 to 12 carbon atoms, p-alkoxyphenyl or p-alkoxybenzyl; R.sup.2 and R.sup.6 each independently signify hydrogen, alkyl with 1 to 12 carbon atoms or phenyl; R.sup.4 denotes hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy or alkyl or alkenyl with 1 to 12 and, respectively, 2 to 12 carbon atoms, which are unsubstituted or mono- or multiply-substituted with halogen, cyano and/or methyl and in which one methylene group or two non-adjacent methylene groups can be replaced by --O--, --COO-- and/or --OOC--; and the oxazoline ring in formula I is present in optically active form, liquid crystalline mixtures which contain such dopants and their use for optical and electro-optical purposes.

Oxaxoline derivatives

Optically active compounds of the formula ##STR1## wherein m stands for the number 1 and R.sup.2 is an unsubstituted or halogen-substituted alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen and/or optionally one methylene group is replaced by an ester group --COO-- or --OOC--; or m stands for the number 0 or 1 and R.sup.2 denotes a group of the formula ##STR2## R.sup.1 and R.sup.3 each independently represent an alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen; Z.sup.1, Z.sup.2 and Z.sup.3 each independently are a single covalent bond, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --COO-- or --OOC--; n stands for the number 0 or 1; rings A.sup.1 and A.sup.2 each independently are unsubstituted or halogen, cyano and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; and C.sup.* denotes a chiral carbon atom; with the proviso that simultaneously R.sup.l does not are an alkyl group, m and n do not are the number 1, Z.sup.1 does not are the group --CH.sub.2 CH.sub.2 -- or --CH.sub.2 O-- and ring A.sup.1, Z.sup.2, ring A.sup.2 and R.sup.2 together do not are 4-(5-alkyl-2-pyrimidinyl)-phenyl, their preparation, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes.

Liquid crystalline mixtures having a chiral tilted smectic phase

Optically active compounds of the formula ##STR1## wherein rings A.sup.1 and A.sup.2 each independently signify pyridine-2,5-diyl, pyrimidine-2,5-diyl or 1,4-phenylene, which is unsubstituted or substituted with at least one of halogen, cyano and/or methyl; R.sup.1 and R.sup.2 each independently represent alkyl with 1 to 18 carbon atoms in which optionally 1 --CH.sub.2 -- group or 2 non-adjacent --CH.sub.2 -- groups is/are replaced by --O--, --COO-- and/or --OOC-- and/or one --CH.sub.2 --CH.sub.2 -- group can be replaced by --CH.dbd.CH--; with the proviso that at least one of the groups R.sup.1 and R.sup.2 must be chiral, liquid crystalline mixtures which contain these compounds and their use for optical and electro-optical purposes.

Optically active piperazinyl derivatives as liquid crystals

Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 is unsubstituted or halogen-, cyano- and/or methylsubstituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3 A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl- -substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane- -1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6- diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently are a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --C.vertline.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.dbd.CH-- CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--; R.sup.3 and R.sup.4 each independently denote halogen, cyano, --NCS, --CF.sub.3, --OCF.sub.3 or alkyl in which optionally one &gt;CH--CH&lt; is replaced by &gt;C.dbd.C&lt; and/or optionally one methylene group or two non- adjacent methylene groups is/are replaced by --O--, --COO-- and/or --OOC-- and/or optionally one methylene group is replaced by --CHX--; and X is halogen, cyano or methyl, as well as liquid crystalline mixtures which contain such compounds and their use for electro-optical purposes.

Growing community of inventors

Mohlin, Switzerland

Stephen Kelly