Liquid crystal compounds having a chiral fluorinated terminal portion

• US 5,702,637 A
• Filed: 04/19/1995
• Issued: 12/30/1997
• Est. Priority Date: 04/19/1995
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Spawn, Terence D., Savu, Patricia M., Radcliffe, Marc D., Snustad, Daniel C., Johnson, Gilbert C.
• Primary Examiner(s): Wu, Shean C.
• Application Number:
  US08/424,892
• Time in Patent Office: 986 Days
• Field of Search: 252/299.01, 252/299.61, 252/299.62, 252/299.63, 544/30, 546/346, 549/380, 560/65, 568/634, 568/649, 570/127, 570/128, 570/129, 570/130, 570/131, 570/132, 570/133, 570/144
• US Class Current: 252/299.61
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/34 One oxygen atom
• CPC Class Codes: C07D 263/24 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C09K 19/04 characterised by the chemical structure of the liquid crystal components , e.g. by a specific unit
• CPC Class Codes: C09K 19/126 Compounds containing at least one asymmetric carbon atom
• CPC Class Codes: C09K 19/3441 having nitrogen as hetero atom
• CPC Class Codes: C09K 19/3458 Uncondensed pyrimidines
• CPC Class Codes: C09K 19/3463 Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
• CPC Class Codes: C09K 19/3466 Pyrimidine with at least another heterocycle in the chain
• CPC Class Codes: C09K 19/3483 the heterocyclic ring being a non-aromatic ring

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.

Claims

1. 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,

space="preserve" listing-type="equation">--C(═

O)--O--, --C(═

O)--S--, --C(═

O)--Se--,

space="preserve" listing-type="equation">--C(═

O)--Te--, --(CH.sub.2 CH.sub.2).sub.k

where

K is 1 to 4,

space="preserve" listing-type="equation">--CH═

CH--, --C.tbd.C--, --CH═

N--, --CH.sub.2 --O--, --C(═

O)--, and --O--;

each X, Y, and Z are independently selected from the group consisting of --H, --Cl, --F, --Br, --I, --OH, --OCH₃, --CH₃, --CF₃, --OCF₃, --CN, and --NO₂ ;

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_s H_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

space="preserve" listing-type="equation">--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,

space="preserve" listing-type="equation">--((C.sub.q'"'"' H.sub.2q'"'"'-v'"'"' --(R'"'"').sub.v'"'"')--O).sub.w --C.sub.q H.sub.2q+1-v --(R'"'"').sub.v,

space="preserve" listing-type="equation">--C(═

O)--O--C.sub.q H.sub.2q+1-v --(R'"'"').sub.v,

space="preserve" listing-type="equation">--O--(O═

)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═

)C--C.sub.q H.sub.2q+1, --C(═

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_q H_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_f '"'"' is --R*--D--(O)_x --CH₂ --D'"'"'--R_f, where R* is a cyclic or acyclic chiral moiety selected from the group consisting of

space="preserve" listing-type="equation">--O--((C.sub.q'"'"' H.sub.2q'"'"'-v'"'"' --(R'"'"').sub.v'"'"')--O).sub.w --C.sub.q H.sub.2q-v --(R'"'"').sub.v --,

space="preserve" listing-type="equation">--((C.sub.q'"'"' H.sub.2q'"'"'-v'"'"' --(R'"'"').sub.v'"'"')--O).sub.w --C.sub.q H.sub.2q-v --(R'"'"').sub.v --,

space="preserve" listing-type="equation">--C(═

O)--O--C.sub.q H.sub.2q-v --(R'"'"').sub.v --,

space="preserve" listing-type="equation">--O--(O═

)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.

2. Fluorine-containing, chiral liquid crystal compounds that have smectic mesophase or latent smectic mesophase and that are represented by the general formula (II):

space="preserve" listing-type="equation">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'"'"')_v --C_q H_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_q H_2q-v --(R'"'"')_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(═

O)--O-- or --CH₂ --;

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_f is selected from the group consisting of --C_q F_2q X'"'"', --R_f "--R_h, and --(C_x F_2x O)_z C_y F_2y+1, where q is an integer of 1 to about 6, X'"'"' is fluorine, R_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_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_x F_2x O), y is an integer of 1 to about 8, and z is an integer of 1 to about 5.