US 5,346,647 AGranted

Cyclohexane compounds used in liquid crystalline mixtures

AssigneeHoffmann-La Roche Inc.

InventorsStephen Kelly, Frans Leenhouts

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Abstract

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 >CH--CH< is replaced by >C.dbd.C< 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.

Claims18

Dependent claims

A compound of formula ##STR9## wherein n is 0 or 1:

R.sup.1 represents a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 --;
R.sup.2 is a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --;
ring A.sup.1 represents 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, the rings A.sup.1 being unsubstituted or substituted with at least one of halogen, cyano or methyl:
A.sup.3, A.sup.4 and ring A.sup.2 each independently represent 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, each of the 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen being unsubstituted or substituted with at least one of halogen, cyano or methyl, 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 and trans-decalin-2,6-diyl;
Z.sup.1, Z.sup.2 and Z.sup.3 each independently represent 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(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or a trans form of --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--;
R.sup.3 and R.sup.4 have a maximum of 18 carbon atoms and each independently represent halogen, cyano, --NCS, --CF.sub.3, --OCF.sub.3, alkyl, alkyl having one >CH--CH<
replaced by >C.dbd.C<, alkyl having one methylene group or two non-adjacent methylene groups replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one methylene group replaced by --CHX--, alkyl with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, and one methylene group being replaced by --CHX--, alkyl having >CH--CH<
replaced by >C.dbd.C<
with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene group replaced by --CHX--, and alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, and one methylene group being replaced by --CHX--;
and X represents halogen, cyano or methyl.

11 more elements

A liquid crystalline mixture with at least 2 components, wherein at least one component is a compound of formula ##STR12## wherein n is 0 or 1;

R.sup.1 represents a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 --;
R.sup.2 is a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --;
ring A.sup.1 represents 1,4-phenylene, or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, the rings A.sup.1 being unsubstituted or substituted with at least one of halogen, cyano or methyl;
A.sup.3, A.sup.4 and ring A.sup.2 each independently represent 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, each of the 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen being unsubstituted or substituted with at least one of halogen, cyano or methyl, 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 and trans-decalin-2,6-diyl;
Z.sup.1, Z.sup.2 and Z.sup.3 each independently represent a single covalent bond, --COO--, --OOC--, CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --C.vertline.--, --(CH.sub.2).sub.3 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or a trans form of --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--;
R.sup.3 and R.sup.4 have a maximum of 18 carbon atoms and each independently represent halogen, cyano, --NCS, --CF.sub.3, --OCF.sub.3, alkyl, alkyl having one >CH--CH<
replaced by >C.dbd.C<, alkyl having one methylene group or two non-adjacent methylene groups replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one methylene group replaced by --CHX--, alkyl with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO--, or --OOC--, and one methylene group being replaced by --CHX--, alkyl having >CH--CH<
replaced by >C.dbd.C<
with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene group replaced by --CHX--, and alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, and one methylene group being replaced by --CHX--;
and X represents halogen, cyano or methyl.

11 more elements

A liquid crystal cell comprising:

a) two plate means;
b) liquid crystal means disposed between the two plate means and including a compound of formula ##STR13## wherein n is 0 or 1:
R.sup.1 represents a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.3 --;
R.sup.2 is a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --;
ring A.sup.1 represents 1,4-phenylene, or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, the rings A.sup.1 being unsubstituted or substituted with at least one of halogen, cyano or methyl;
A.sup.3, A.sup.4 and ring A.sup.2 each independently represent 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen, each of the 1,4-phenylene or 1,4-phenylene having 1CH or 2CH groups replaced by nitrogen being unsubstituted or substituted with at least one of halogen, cyano or methyl, 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 and trans-decalin-2,6-diyl;
Z.sup.1, Z.sup. 2 and Z.sup.3 each independently represent 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(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or a trans form of --CH.dbd.CH--CH.sub.2 O-- or --OCH.sub.2 --CH.dbd.CH--;
R.sup.3 and R.sup.4 have a maximum of 18 carbon atoms each independently represent halogen, cyano, --NCS, --CF.sub.3, --OC.sub.3, alkyl, alkyl having one >CH--CH<
replaced by >C.dbd.C<, alkyl having one methylene group or two non-adjacent methylene groups replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one methylene group replaced by --CHX--, alkyl with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, and one methylene group being replaced by --CHX--, alkyl having >CH--CH replaced by >C.dbd.C<
with one methylene group or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene group replaced by --CHX--, and alkyl having one >CH--CH<
replaced by >C.dbd.C<
with one methylene or two non-adjacent methylene groups being replaced by at least one of --O--, --COO-- or --OOC--, and one methylene group being replaced by --CHX--;
and X represents halogen, cyano or methyl;
and
c) means for applying an electrical potential to said plate means.

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/166,603Filed 13 Dec 1993 · continuation
Priority: CH 2779/8925 Jul 1989
Granted: 13 Sep 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification30 codes

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…
C07C 13/28
Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings: polycyclic hydrocarbons or acyclic hydrocarbon…
C07C 22/08
Containing six-membered aromatic rings: containing fluorine
C07C 25/18
Compounds containing at least one halogen atom bound to a six-membered aromatic ring: polycyclic aromatic halogenated hydrocarbons

Family

Serial554,636Parent of this continuation · filed 17 Jul 1990
Serial943,375Parent of this continuation · filed 10 Sep 1992
US 5,346,647 AThis patent

From the US filing history. Foreign family members aren’t listed.

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