US 6,309,561 B1 · Liquid crystal compounds having a chiral fluorinated terminal portion

Abstract

Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.

Claims29

Dependent claims

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted;

(ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group, wherein the fluoroalkyl and perfluoroalkyl groups are represented by the formula —CqF2qX′, wherein q is at least about 5 and X′ is hydrogen or fluorine;
and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom;
(b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted;
and (c) a central core connecting said terminal portions;
said alkylene or fluoroalkylene group of said chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between said chiral center of said chiral fluorochemical terminal portion and said central core.

2 more elements

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion;

(b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted;
and (c) a central core connecting said terminal portions;
said alkylene or fluoroalkylene group of said chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between said chiral center of said chiral fluorochemical terminal portion and said central core;
wherein said compounds are represented by the general formula (I):
where M, N and P are each independently selected from the group consisting of
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(═O)—O—, —C(═O)—S—, —C(═O)—Se—, —C(═O)—Te—, —(CH2CH2)k— where k is 1 to 4, —CH═CH—, —C≡C—, —CH═N—, —CH2—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 1, m, and n are independently zero or an integer of 1 to 4;
each D is non-directionally and independently selected from the group consisting of a covalent bond,
—C(═O)—O—CrH2r—, —O—CrH2r—, —O—(O═)C—CrH2r—, —C≡C—, —CH═CH—, —C(═O)—, —O[Parenopenst]CsH2sO[Parenclosest]tCrH2r—, —Cr′H2r′—, [Parenopenst]CsH2sO[Parenclosest]tCr′H2r′—, —O—, —S—,
where one or more hydrogen atoms can optionally be replaced with fluorine, and where r and r′ are independently integers of 0 to about 20, s is independently an integer of 1 to about 10 for each (CsH2sO), 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—((Cq′H2q′−v′—(R′)v′)—O)w—CqH2q+1−v—(R′)v, —((Cq′H2q′−v′—(R′)v′)—O)w—CqH2q+1−v—(R′)v, —C(═O)—O—CqH2q+1−v—(R′)v, —O—(O═)C—CqH2q+1−v—(R′)v,
—CR′H—(D)g—CR′H—CqH2q+1−v—(R′)v,
where each R′ is independently selected from the group consisting of —Cl, —F, —CF3, —NO2, —CN, —H, —CqH2q+1,
—O—(O═)C—CqH2q+1, —C(═O)—O—CqH2q+1, —Br, —OH, and —OCqH2q+1;
q′ is independently an integer of 1 to about 20 for each (Cq′H2q′—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 2;
each v′ is independently an integer of 0 to about 2;
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 can be chiral or achiral;
and R* is a cyclic or acyclic chiral moiety containing at least one chiral center;
and Rf is perfluoroether;
with the proviso that there are at least 3 in-chain atoms between said central core structure —(M)a—A[Parenopenst]N[Parenclosest]bB[Parenopenst]P[Parenclosest]c— and at least one said chiral center of R*.

25 more elements

Fluorine-containing, chiral liquid crystal compounds having smectic mesophases or latent smectic mesophases, the compounds comprising (a) a chiral fluorochemical terminal portion;

(b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted;
and (c) a central core connecting said terminal portions;
said alkylene or fluoroalkylene group of said chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between said chiral center of said chiral fluorochemical terminal portion and said central core;
wherein said compounds are represented by the general formula (II):
R″—(O)j—G—D′—R*—(Cs′H2s′O)t′Cr″H2r″—Rf (II)
where R″ is (R′)v—CqH2q+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 2;
j is an integer of 0 or 1;
G is selected from the group consisting of
where one or more aromatic hydrogen atoms can be replaced with fluorine;
D′ is selected from the group consisting of —O[Parenopenst]CsH2sO[Parenclosest]tCr′H2r′—, —CrH2r—, [Parenopenst]CsH2sO[Parenclosest]tCr′H2r′—, and —O—CrH2r—, where r and r′ are independently integers of 0 to about 12, s is independently an integer of 1 to about 10 for each (CsH2sO), and t is an integer of 1 to about 3;
R* is selected from the group consisting of —CqH2q−v—(R′)v— and
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 —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
Rf is selected from the group consisting of —CqF2q+1 and —(CxF2xO)zCyF2y+1, where q is an integer of 1 to about 6, x is independently an integer of 1 to about 10 for each (CxF2xO), y is an integer of 1 to about 8, and z is an integer of 1 to about 5;
with the proviso that there are at least 3 in-chain atoms between said central core structure G and at least one said chiral center of R*.

15 more elements

Chiral liquid crystal intermediate compounds represented by the following general formulas IV and VI:

where N and P are each independently selected from the group consisting of
b and c are each independently zero or an integer of from 1 to 3;
B is non-directionally selected from the group consisting of a covalent bond, —C(═O)—O—, —C(═O)—S—, —C(═O)—Se—, —C(═O)—Te—, —(CH2CH2)k— where k is 1 to 4, —CH═CH—, —C≡C—, —CH═N—, —CH2—O—, —C(═O)—, and —O—;
each 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 m and n are independently zero or an integer of 1 to 4;
each D is non-directionally and independently selected from the group consisting of a covalent bond, —C(═O)—O—CrH2r—, —O—CrH2r—, —O—(O═)C—CrH2r—, —C≡C—, —CH═CH—, —C(═O)—, —O[Parenopenst]CsH2sO[Parenclosest]tCrH2r—, —Cr′H2r′—, [Parenopenst]CsH2sO[Parenclosest]tCr′H2r′—, —O—, —S—,
where one or more hydrogen atoms can optionally be replaced with fluorine, and where r and r′ are independently integers of 0 to about 20, s is independently an integer of 1 to about 10 for each (CsH2sO), t is an integer of 1 to about 6, and p is an integer of 0 to about 4;
R* is a cyclic or acyclic chiral moiety containing at least one chiral center and selected from the group consisting of —O—((Cq′H2q′−v′—(R′)v′)—O)w—CqH2q−v—(R′)v —((Cq′H2q′−v′—(R′)v′)—O)w—CqH2q−v—(R′)v—, —C(═O)—O—CqH2q−v—(R′)v—, —O—(O═)C—CqH2q−v—(R′)v—,
where each R′ is independently selected from the group consisting of —Cl, —F, —CF3, —NO2, —CN, —H, —CqH2q+1, —O—(O═)C—CqH2q+1, —C(═O)—O—CqH2q+1, —Br, —OH, and —OCqH2q+1;
q′ is independently an integer of 1 to about 20 for each (CqH2q′—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 3;
each v′ is independently an integer of 0 to about 3;
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 with the proviso that R* is chiral;
Rf is perfluoroether;
with the proviso that there are at least 3 in-chain atoms between said central core structure
or
and at least one said chiral center of R*;
and A″ and B″ are selected from the group consisting of —H, —Cl, —Br, —I, —OH, —COOH, —CH(CH2OH)2, —SH, —SeH, —TeH, —NH2, —COCl, —CHO,—C≡CH, dialkyl borane, —CH═CH2, —OSO2Rf′″, —OSO2CH3, —OSO2-cyclo(C6H4)—CH3, —CH2COOH, —NH(C═O)OCqH2q+1, —NCO, and —CH(C(O)O—CqH2q+1)2, where Rf′″ is a perfluoroalkyl group having from 1 to about 10 carbon atoms and q is an integer of 0 to about 20.

20 more elements

Dependencies are inferred from the claim text.

Liquid crystal compounds having a chiral fluorinated terminal portion

Life of this patent

Liquid crystal compounds having a chiral fluorinated terminal portion

Life of this patent

Abstract

Claims29