Liquid crystal compounds having a chiral fluorinated terminal portion
AssigneeMinnesota Mining and Manufacturing Company
InventorsGilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Abstract
Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
Claims2
Fluorine-containing, chiral liquid crystal compounds that have smectic mesophases or latent smectic mesophases and that are represented by the general formula (I):
- ##STR53## where M, N, and P are each independently selected from the group consisting of ##STR54## a, b, and c are each independently zero or an integer of from 1 to 3, with the proviso that the sum of a+b+c be at least 1;
- each A and B are non-directionally and independently selected from the group consisting of a covalent bond,
- --C(.dbd.O)--O--, --C(.dbd.O)--S--, --C(.dbd.O)--Se--,
- --C(.dbd.O)--Te--, --(CH.sub.2 CH.sub.2).sub.k
- where
- K is 1 to 4,
- --CH.dbd.CH--, --C.tbd.C--, --CH.dbd.N--, --CH.sub.2 --O--, --C(.dbd.O)--, and --O--;
- each X, Y, and Z are independently selected from the group consisting of --H, --Cl, --F, --Br, --I, --OH, --OCH.sub.3, --CH.sub.3, --CF.sub.3, --OCF.sub.3, --CN, and --NO.sub.2 ;
- each l, m, and n are independently zero or an integer of 1 to 4;
- D is non-directionally selected from the group consisting of a covalent bond, ##STR55## and combinations thereof, where r and r' are independently integers of 0 to about 20, s is independently an integer of 1 to about 10 for each (C.sub.s H.sub.2s O), t is an integer of 1 to about 6, and p is an integer of 0 to about 4;
- R is selected from the group consisting of
- --O--((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q+1-v --(R').sub.v,
- --((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q+1-v --(R').sub.v,
- --C(.dbd.O)--O--C.sub.q H.sub.2q+1-v --(R').sub.v,
- --O--(O.dbd.)C--C.sub.q H.sub.2q+1-v --(R').sub.v, ##STR56## where each R' is independently selected from the group consisting of --Cl, --F, --CF.sub.3, --NO.sub.2, --CN, --H, --C.sub.q H.sub.2q+1, --O--(O.dbd.)C--C.sub.q H.sub.2q+1, --C(.dbd.O)--O--C.sub.q H.sub.2q+1, --Br, --OH, and --OC.sub.q H.sub.2q+1 ;
- q' is independently an integer of 1 to about 20 for each (C.sub.q H.sub.2q' --O);
- q is an integer of 1 to about 20;
- w is an integer of 0 to about 10;
- v is an integer of 0 to about 6;
- each v' is independently an integer of 0 to about 6;
- g is an integer of 1 to about 3;
- each D is independently and non-directionally selected from the group set forth for D above, with the proviso that the ring containing D has from about 3 to about 10 ring atoms;
- each W is independently selected from the group consisting of N, CR', and SiR';
- and R is chiral or achiral;
- and
- R.sub.f ' is --R*--D--(O).sub.x --CH.sub.2 --D'--R.sub.f, where R* is a cyclic or acyclic chiral moiety selected from the group consisting of
- --O--((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q-v --(R').sub.v --,
- --((C.sub.q' H.sub.2q'-v' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q-v --(R').sub.v --,
- --C(.dbd.O)--O--C.sub.q H.sub.2q-v --(R').sub.v --,
- --O--(O.dbd.)C--C.sub.q H.sub.2q-v --(R').sub.v --, ##STR57## where each R' is --F;
- q' is independently an integer of 1 to about 20 for each (C.sub.q' H.sub.2q' --O);
- q is an integer of 1 to about 20;
- w is an integer of 0 to about 10;
- v is an integer of 1 to about 3;
- each v' is independently an integer of 0 to about 6;
- g is an integer of 1 to about 3;
- each D is independently and non-directionally selected from the group set forth for D above, with the proviso that the ring containing D has from about 3 to about 10 ring atoms;
- each W is independently selected from the group consisting of N and CH;
- and with the proviso that R* is chiral;
- D and D' are each independently and non-directionally selected from the group set forth for D above;
- x is an integer of 0 or 1;
- and R.sub.f is fluoroalkyl, perfluoroalkyl, fluoroether, or perfluoroether.
Fluorine-containing, chiral liquid crystal compounds that have smectic mesophase or latent smectic mesophase and that are represented by the general formula (II):
- R" --(O).sub.j --G--(OCH.sub.2).sub.j --R*--(C.sub.s H.sub.2s O).sub.t C.sub.r' H.sub.2r' --R.sub.f (II)
- where R" is (R').sub.v --C.sub.q H.sub.2q+1-v, where q is an integer of 2 to about 10, each R' is independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, and perfluoromethyl, and v is an integer of 1 to about 3;
- j is an integer of 0 or 1;
- G is selected from the group consisting of ##STR58## R* is selected from the group consisting of --C.sub.q H.sub.2q-v --(R').sub.v -- and ##STR59## where R' is --F, q is an integer of 1 to about 4, v is an integer of 1 to about 3, W is N or CH, and D is a cyclic or acyclic chiral moiety --C(.dbd.O)--O-- or --CH.sub.2 --;
- s is an integer of 1 to about 6;
- t is an integer of 0 or 1;
- r' is an integer of 1 to about 3;
- and R.sub.f is selected from the group consisting of --C.sub.q F.sub.2q X', --R.sub.f "--R.sub.h, and --(C.sub.x F.sub.2x O).sub.z C.sub.y F.sub.2y+1, where q is an integer of 1 to about 6, X' is fluorine, R.sub.f " is a linear or branched, perfluorinated alkylene group having from about 2 to about 4 carbon atoms and optionally containing one or more catenary ether oxygen atoms, R.sub.h is a linear or branched alkyl group having from about 2 to about 7 carbon atoms and optionally containing one or more catenary ether oxygen atoms, x is independently an integer of i to about 10 for each (C.sub.x F.sub.2x O), y is an integer of 1 to about 8, and z is an integer of 1 to about 5.
Dependencies are inferred from the claim text.