US 7,678,292 B2 · Liquid crystal dopants

Abstract

An ionic dopant comprising a sulfur or a phosphorus containing anion with a randon cation, for use in a smectic A liquid crystal composition. The cation preferably comprises a quaternary ammonium cation.

Claims19

Dependent claims

A method to reduce the driving voltage of a device comprising a smectic A liquid crystal composition and to enhance dynamic light scattering of the composition, said method comprising doping a smectic A liquid crystal composition with an ionic dopant comprising a sulfur or a phosphorous containing anion with a cation.

A smectic A liquid crystal composition, comprising one or more ionic dopants, wherein the ionic dopant comprises a sulfur containing anion with a cation, wherein the ionic dopant reduces the driving voltage of a device comprising the smectic A liquid crystal composition and enhances dynamic light scattering of the composition, wherein:

(a) the anion comprises X, and X is one of the following:
S−, SO2−, SO4− or NHSO3−;
or
(b) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2− or NHSO3−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaplithalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(c) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3− or NHSO3−;
m is 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(d) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3− or NHSO3−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1—(CO2)—R3, R1—(CO2)—R2R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(e) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3− or NHSO3−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(f) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3− or NHSO3−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(g) the anion comprises:
wherein X is SO3−, and R3 is an alkoxy chain;
or
(h) the anion is chiral;
or
(i) the cation is based on an N,N′-dialkylimidazole, an N,N′-dialkylbenzimidazole, an N,N′-dialkyltriazole, an N-alkylquinuclidine or an N-alkylazanaphthalene;
or
(j) the cation is according to formula II:
Y—(CH2)q—R II
wherein Y is NR4R5R6 wherein R4, R5 and R6 is in every instance an alkyl group or an alkyl chain containing 0 to 5 carbon atoms, N-alkylimidazoles, N-alkylbenzimidazoles, N-alkyltriazoles, alkyiquinuclidines or alkylazanaphthalenes;
q is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(k) the cation is according to formula II:
Y—(CH2)q—R II
wherein Y is NR4R5R6 wherein R4, R5 and R6 is in every instance an alkyl group or an alkyl chain containing 0 to 5 carbon atoms, pyridines, N-alkylimidazoles, N-alkylbenzimidazoles, N-alkyltriazoles, alkyiquinuclidines or alkylazanaphthalenes;
q is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a cyano group, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(l) the cation is:
where R7, R8, R9 and R10 are alkyl chains;
or
(m) the cation is n-hexadecyltrimethylammonium (HTMA) or n-hexadecyldimethylethyl-ammonium (HDME);
or
(n) the cation is chiral;
or
(o) the dopant is:

90 more elements

A smectic A liquid crystal composition, comprising one or more ionic dopants, wherein the ionic dopant comprises a quaternary ammonium cation with an anion, wherein the ionic dopant reduces the driving voltage of a device comprising the smectic A liquid crystal composition and enhances dynamic light scattering of the composition, wherein:

(a) the anion is a phosphorus containing anion;
or
(b) the anion comprises X, and X is one of the following:
S−, SO2−, SO4−, NHSO3, POH−, PO2H−, PO3H−, (PO3)2−, PO4H− or (PO4);
or
(c) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, NHSO3−, POH−, PO2H−, PO3H− or (PO3)2−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(d) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3−, NHSO3−, POH−, PO2H−, PO3H− or (PO3)2−;
m is 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(e) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3−, NHSO3−, POH−, PO2H−, PO3H− or (PO3)2−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1—(CO2)—R3, R1—(CO2)—R2R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(f) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3−, NHSO3−, POH−, PO2H−, PO3H− or (PO3)2−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(g) the anion is according to formula I:
X—Om(CH2)n—R I
wherein X is S−, SO2−, SO3−, NHSO3−, POH−, PO2H−, PO3H−or (PO3)2−;
m is 0 or 1;
n is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(h) the anion comprises:
wherein X is SO3−, PO3H− or (PO3)2−, and R3 is an alkoxy chain;
or
(i) the anion is chiral;
or
(j) the cation is based on an N,N′-dialkylimidazole, an N,N′-dialkylbenzimidazole, an N,N′-dialkyltriazole, an N-alkylquinuclidine or an N-alkylazanaphthalene;
or
(k) the cation is according to formula II:
Y—(CH2)q—R II
wherein Y is NR4R5R6 wherein R4, R5 and R6 is in every instance an alkyl group or an alkyl chain containing 0 to 5 carbon atoms, N-alkylimidazoles, N-alkylbenzimidazoles, N-alkyltriazoles, alkyiquinuclidines or alkylazanaphthalenes;
q is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a hydrogen, a cyano group, an alkyl chain, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(l) the cation is according to formula II:
Y—(CH2)q—R II
wherein Y is NR4R5R6 wherein R4, R5 and R6 is in every instance an alkyl group or an alkyl chain containing 0 to 5 carbon atoms, pyridines, N-alkylimidazoles, N-alkylbenzimidazoles, N-alkyltriazoles, alkyiquinuclidines or alkylazanaphthalenes;
q is 0 to 19;
and R is R3, R1R3, R1—(CO2)—R3, R1—(CO2)—R2R3, R1—(CH2)p—R3, or R1—(CH2)p—R2R3;
wherein R1 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R2 is a phenyl, a substituted phenyl, a biphenyl, a substituted biphenyl, a terphenyl, a substituted terphenyl, an aromatic ring, a non-aromatic ring, a cyclohexyl, a cyclopentyl, a diazine, a bidiazine, a terdiazine, a phenyldiazine, a biphenyldiazine, a naphthalene or an azanaphthalene;
R3 is a cyano group, an alkyl substituted cyclohexyl, an alkenyl chain, or an alkyl chain wherein one or more non-adjacent CH2-groups are replaced by an oxygen atom;
and p is 0 to 19;
or
(m) the cation is:
where R7, R8, R9 and R10 are alkyl chains;
or
(n) the cation is n-hexadecyltrimethylammonium (HTMA) or n-hexadecyldimethylethyl-ammonium (HDME);
or
(o) the cation is chiral;
or
(p) the dopant is:

92 more elements

Dependencies are inferred from the claim text.

Liquid crystal dopants

Life of this patent

Abstract

Claims19

Liquid crystal dopants

Life of this patent

Abstract

Claims19