Chiral liquid crystal compounds having a perfluoroether terminal portion
AssigneeMinnesota Mining and Manufacturing Company
InventorsEugene P. Janulis, Gilbert 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) an aliphatic fluorocarbon terminal portion containing at least two catenary ether oxygen atoms; (b) a chiral, aliphatic 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.
Claims21
Fluorine-containing, chiral liquid crystal compounds represented by the general formula (I):
- ##STR44## where M, N, and P are each independently selected from the group consisting of ##STR45## 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, ##STR46## 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, --CF3, --OCF.sub.3 --CN, and --NO.sub.2 ;
- each 1, m, and n are independently zero or an integer of 1 to 4;
- D is selected from the group consisting of a covalent bond, ##STR47## and combinations thereof, where r and r' are independently integers of 1 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, ##STR48## 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, ##STR49## where 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, g'is an integer of 1, each D is independently selected from the group set forth above, and R is linear or branched, with the proviso that R is chiral;
- and
- R.sub.f is --(C.sub.x F.sub.2x O).sub.z C.sub.y F.sub.2y+1, where x is independently an integer of 1 to about 10 for each C.sub.x F.sub.2x O, y is an integer of 1 to about 10, and z is an integer of 2 to about 10.
A process for preparing fluorine-containing, chiral liquid crystal compounds comprising the steps of (a) mixing at least one compound represented by the formula ##STR66## with at least one compound represented by the formula ##STR67## or mixing at least one compound represented by the formula ##STR68## with at least one compound represented by the formula ##STR69## where M, N, and P are each independently selected from the group consisting of ##STR70## 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, ##STR71## each A', A'', B', and B'' are independently selected from the group consisting of --OH, --COOH, --CH(CH.sub.2 OH).sub.2, --SH, --SeH, --the, --NH.sub.2, --COCl, --CHO, --OSO.sub.2 R.sub.f ', --OSO.sub.2 CH.sub.3, --OSO.sub.2 -cyclo(C.sub.6 H.sub.4)--CH.sub.3, and --CH.sub.2 COOH, where R.sub.f ' is a perfluoroalkyl group having from 1 to about 10 carbon atoms, and with the proviso that A' can enter into a coupling reaction with A'' and that B' can enter into a coupling reaction with B'';
- 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, --CF3, --OCF.sub.3 --CN, and --NO.sub.2 ;
- each 1, m, and n are independently zero or an integer of 1 to 4;
- D is selected from the group consisting of a covalent bond, ##STR72## and combinations thereof, where r and r' are independently integers of 1 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' --(R').sub.v')--O).sub.w --C.sub.q H.sub.2q+1-v R'.sub.v, ##STR73## 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, ##STR74## where 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, g' is an integer of 1, each D is independently selected from the group set forth above other than C.tbd.C, with the proviso that R is chiral;
- and
- R.sub.f is --(C.sub.x F.sub.2x O).sub.z C.sub.y F.sub.2y+1, where x is independently an integer of 1 to about 10 for each C.sub.x F.sub.2x O, y is an integer of 1 to about 10, and z is an integer of 2 to about 10;
- and (b) allowing said A' and A'' or B'' and B'' to react.
Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) an aliphatic fluorocarbon terminal portion containing at least two catenary ether oxygen atoms in at least one perfluorinated segment thereof;
- (b) a chiral, aliphatic hydrocarbon terminal portion;
- and (c) a central core connecting said terminal portions.
Dependencies are inferred from the claim text.