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US 5,536,818 AGranted
Dichroic azo dye, liquid crystal composition containing the same, and liquid crystal element using the composition
AssigneeMitsubishi Chemical Corporation
InventorsMasaharu Kaneko, Hisayo Ishio
Life of this patent
Estimating the term…
Abstract
A dichroic dye represented by the formula (I) or (II): ##STR1## wherein the substituents are as described in the specification. The dichroic dyes (I) and (II) exhibit excellent dichroism and can be prepared from 2,2'-ditrifluoromethylbenzidine having no toxicity, such as mutagenicity.
Claims17
A dichroic dye represented by formula (I):
- ##STR72## wherein R.sup.1 and R.sup.2 each represent a hydrogen atom or a nonionic substituent;
- X.sup.1 and X.sup.2 each represent ##STR73## Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5, Z.sup.6, Z.sup.7, Z.sup.8, Z.sup.9, Z.sup.10, Z.sup.11, Z.sup.12, Z.sup.13, Z.sup.14, Z.sup.15, and Z.sup.16 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.1 and Z.sup.2, Z.sup.4 and Z.sup.5, Z.sup.7 and Z.sup.8, Z.sup.10 and Z.sup.11, or Z.sup.13 and Z.sup.14 may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- and n and m each represent 0, 1 or 2, or formula (II):
- ##STR74## wherein R.sup.11, R.sup.12, R.sup.13, and R.sup.14 each represent a hydrogen atom, an alkyl group, an alkoxyalkyl group, a substituted or unsubstituted aralkyl group or a fluoroalkyl-substituted alkyl group, provided that a compound in which R.sup.11 is a hydrogen atom and R.sup.12 is a substituted or unsubstituted aralkyl group and a compound in which R.sup.13 is a hydrogen atom and R.sup.14 is a substituted or unsubstituted aralkyl group are excluded;
- R.sup.11 and R.sup.12, or R.sup.13 and R.sup.14 may be connected to each other to form a nitrogen-containing aliphatic ring;
- Z.sup.21, Z.sup.22, Z.sup.23, Z.sup.24, Z.sup.25, Z.sup.26, Z.sup.27, Z.sup.28, Z.sup.29, Z.sup.30, Z.sup.31, and Z.sup.32 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.21 and Z.sup.22, Z.sup.24 and Z.sup.25, Z.sup.27 and Z.sup.28, and Z.sup.31 may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- R.sup.11 and Z.sup.23, R.sup.12 and Z.sup.21, R.sup.13 and Z.sup.32, or R.sup.14 and Z.sup.31 may be connected to each other to form a nitrogen-containing aliphatic ring;
- and p and q each represent 0, 1 or 2, provided that p and q are not simultaneously 0.
7 more elements
A liquid crystal composition containing at least one liquid crystal compound and at least one dichroic dye selected from the group consisting of a compound represented by formula (I):
- ##STR78## wherein R.sup.1, and R.sup.2, each represent a hydrogen atom or a nonionic substituent;
- X.sup.1, and X.sup.2, each represent ##STR79## Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5, Z.sup.6, Z.sup.7, Z.sup.8, Z.sup.9, Z.sup.10, Z.sup.11, Z.sup.12, Z.sup.13, Z.sup.14, Z.sup.15, and Z.sup.16 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.1, and Z.sup.2, Z.sup.4 and Z.sup.5, Z.sup.7, and Z.sup.8, Z.sup.10, and Z.sup.11, or Z.sup.13 and Z.sup.14 may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- and n and m each represent 0, 1, or 2, and a compound represented by formula (II):
- ##STR80## wherein R.sup.11, R.sup.12, R.sup.13, and R.sup.14, each represent a hydrogen atom, an alkyl group, an alkoxyalkyl group, a substituted or unsubstituted aralkyl group or a fluoroalkyl-substituted alkyl group, provided that a compound in which R.sup.11 is a hydrogen atom and R.sup.12 is a substituted or unsubstituted aralkyl group and a compound in which R.sup.13 is a hydrogen atom and R.sup.14 is a substituted or unsubstituted aralkyl group are excluded;
- R.sup.11 and R.sup.12, or R.sup.13 and R.sup.14 may be connected to each other to form a nitrogen-containing aliphatic ring;
- Z.sup.21, Z.sup.22, Z.sup.23, Z.sup.24, Z.sup.25, Z.sup.26, Z.sup.27, Z.sup.28, Z.sup.29, Z.sup.30, Z.sup.31, and Z.sup.32 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.21, and Z.sup.22, Z.sup.24, and Z.sup.25, Z.sup.27 and Z.sup.28, or Z.sup.30 and Z.sup.31, may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- R.sup.11, and Z.sup.23, R.sup.12, and Z.sup.21, R.sup.13 and Z.sup.32, or R.sup.14, and Z.sup.31, may be connected to each other to form a nitrogen-containing aliphatic ring;
- and p and q each represent 0, 1, or 2, provided that p and q are not simultaneously 0.
7 more elements
A liquid crystal element using a liquid crystal composition containing at least one liquid crystal compound and at least one dichroic dye selected from the group consisting of a compound represented by formula (I):
- ##STR84## wherein R.sup.1 and R.sup.2 each represent a hydrogen atom or a nonionic substituent;
- X.sup.1 and X.sup.2 each represent ##STR85## Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.5, Z.sup.6, Z.sup.7, Z.sup.8, Z.sup.9, Z.sup.10, Z.sup.11, Z.sup.12, Z.sup.13, Z.sup.14, Z.sup.15, and Z.sup.16 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.1, and Z.sup.2, Z.sup.4, and Z.sup.5, Z.sup.7, and Z.sup.8, Z.sup.10 and Z.sup.11, or Z.sup.13 and Z.sup.14 may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- and n and m each represent 0, 1, or 2, and a compound represented by formula (II):
- ##STR86## wherein R.sup.11, R.sup.12, R.sup.13, and R.sup.14, each represent a hydrogen atom, an alkyl group, an alkoxyalkyl group, a substituted or unsubstituted aralkyl group or a fluoroalkyl-substituted alkyl group, provided that a compound in which R.sup.11, is a hydrogen atom and R.sup.12 is a substituted or unsubstituted aralkyl group and a compound in which R.sup.13 is a hydrogen atom and R.sup.14 is a substituted or unsubstituted aralkyl group are excluded;
- R.sup.11, and R.sup.12, or R.sup.13 and R.sup.14 may be connected to each other to form a nitrogen-containing aliphatic ring;
- Z.sup.21, Z.sup.22, Z.sup.23, Z.sup.24, Z.sup.25, Z.sup.26, Z.sup.27, Z.sup.28, Z.sup.29, Z.sup.30, Z.sup.31, and Z.sup.32 each represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group;
- Z.sup.21, and Z.sup.22, Z.sup.24, and Z.sup.25, Z.sup.27 and Z.sup.28, or Z.sup.30 , and Z.sup.31 may be connected to each other to form an aliphatic, aromatic or nitrogen-containing aromatic ring;
- R.sup.11, and Z.sup.23, R.sup.12, and Z.sup.21, R.sup.13 and Z.sup.32, or R.sup.14 and Z.sup.31 may be connected to each other to form a nitrogen-containing aliphatic ring;
- and p and q each represent 0, 1, or 2, provided that p and q are not simultaneously 0.
7 more elements
Dependencies are inferred from the claim text.