Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative novel coumarin derivative, novel nile red derivative, and novel anthracene derivative

Patent metadata

Field	Value
Publication number	US-9475991-B2
Application number	US-201214002363-A
Country	US
Kind code	B2
Filing date	Mar 15, 2012
Priority date	Mar 30, 2011
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

Provided are a polymerizable liquid crystal composition, a coating material, a medium, and a polarizing device each produced using a polymerizable liquid crystal compound and a colorant and each capable of producing polarized light suitable for polarizing devices, and also a novel naphtholactam derivative, a novel coumarin derivative, a novel Nile Red derivative, and a novel anthracene derivative each suitable for use as the colorant. Specifically provided are a polymerizable liquid crystal composition containing (A) at least one liquid crystal compound having a polymerizable functional group, (B) at least one colorant, and (C) a polymerization initiator, and a novel naphtholactam derivative of formula (IV′), a novel coumarin derivative of formula (VI′), a novel Nile Red derivative of formula (VII′), and a novel anthracene derivative of formula (VIII′) each suitable for use as the colorant (B).

First claim

The invention claimed is:

1. A polymerizable liquid crystal composition, comprising:
(A) at least one liquid crystal compound having a polymerizable functional group,
(B) at least one colorant, and
(C) a polymerization initiator,

wherein (B) is represented by formula (VI):

wherein
X 111 represents a nitrogen atom or CR 116 , R 111 to R 116 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, an aldehyde group, a carboxyl group, a hydroxyl group, —NRR′, an organosilyl group, an optionally substituted alkyl group of 1 to 30 carbon atoms, an optionally substituted aryl group of 6 to 30 carbon atoms, an optionally substituted arylalkyl group of 7 to 30 carbon atoms, an optionally substituted heterocyclic group of 2 to 30 carbon atoms, or a substituent represented by formula (V),
a methylene chain in the alkyl group or the arylalkyl group represented by each of R 111 to R 116 may be interrupted by —O—, —S—, —SO 2 —, —CO—, —OCO—, or —COO—, the aryl group represented by each of R 111 to R 116 and the coumarin structure may be linked together via —O—, —S—, —SO 2 —, —CO—, —OCO—, or —COO—, and the methylene chain may be replaced by —CH═CH— or —C≡C—,
adjacent two or more of R 111 to R 116 may be linked together to form a ring, or when any one of R 111 to R 116 is —NRR′, R or R′ and any other one of R 111 to R 116 adjacent thereto may be linked together to form a ring,
R and R′ each independently represent a hydrogen atom, an optionally substituted alkyl group of 1 to 30 carbon atoms, or an optionally substituted aryl group of 6 to 30 carbon atoms,
a methylene chain in the alkyl group represented by each of R and R′ may be interrupted by —O—, —S—, —SO 2 —, —CO—, —OCO—, or —COO—, the aryl group represented by each of R and R′ and the coumarin structure may be linked together via —O—, —S—, —SO 2 —, —CO—, —OCO—, or —COO—, and the methylene chain may be replaced by —C═C— or —C≡C—,
at least one of R 111 to R 116 represents a substituent represented by formula (V):

wherein
A 5 , A 6 , A 7 , and A 8 each independently represent a benzene ring, a cyclohexane ring, a cyclohexene ring, a naphthalene ring, a decahydronaphthalene ring, or a tetrahydronaphthalene ring,
S 3 represents an alkylene group of 1 to 8 carbon atoms, the alkylene group represented by S 3 may be substituted with a halogen atom and branched, and a methylene chain in the alkylene group represented by S 3 may be substituted with a halogen atom, branched, and interrupted by -0-,
Z 6 , Z 7 , Z 8 , Z 9 , and Z 10 each independently represent a direct bond, -L 2 -, —O—CO—, —CO—O—, -L 2 0-, —OL 2 -, -L 2 O—CO—, -L 2 CO—O—, -L 2 O—CO—O—, —O—COL 2 -, —CO—OL 2 -, —O—CO—OL 2 -, —CO—CH═CH, —CH═CH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, or —CH 2 ═N—N═CH 2 —,
L 2 represents an alkylene group of 1 to 8 carbon atoms, the alkylene group may be branched and may be substituted with a halogen atom or a cyano group, and a methylene chain in the alkylene group represented by L2 may be interrupted by -0-, —CH═CH—, or —C≡C—,
Y 5 , Y 6 , Y 7 and Y 8 each independently represent an alkyl group of 1 to 6 carbon atoms, a halogen atom, or a cyano group, a hydrogen atom of the alkyl group represented by each of Y 5 , Y 6 , Y 7 and Y 8 may be substituted with a halogen atom or a cyano group, and a methylene chain in the alkyl group represented by each of Y 5 , Y 6 , Y 7 and Y 8 may be interrupted by -0- or —CO—,
m, n, p, and q are each independently from 0 to 8,
s is 1,
t and u are each independently 0 or 1,
r is 1 or 2, and
G 3 represents a substituent selected from the group consisting of substituents represented by formulae (5) to (14) below:

wherein in formula (5), M 2 represents a hydrogen atom, a methyl group, or a halogen atom; in formula (6), R 11 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; in formula (7), R 12 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; in formula (8), R 13 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; in formula (9), R 14 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; and in formula (11), Z 11 represents methylene, an oxygen atom, or —CO—.

2. The polymerizable liquid crystal composition according to claim 1 , wherein the liquid crystal compound as the component (A) having a polymerizable functional group is a liquid crystal compound represented by formula (I):

wherein
rings A 1 , A 2 , A 3 , and A 4 each independently represent a benzene ring, a cyclohexane ring, a cyclohexene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a decahydronaphthalene ring, a tetrahydronaphthalene ring, or an optically active linking group,
S 1 and S 2 each independently represent an alkylene group of 1 to 8 carbon atoms, the alkylene group represented by each of S 1 and S 2 may be substituted with a halogen atom and may be branched, and a methylene chain in the alkylene group represented by each of S 1 and S 2 may be interrupted by —O—,
Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 each independently represent a direct bond, -L 1 -, —O—CO—, —CO—O—, -L 1 O—, —OL 1 -, -L 1 O—CO—, -L 1 CO—O—, -L 1 O—CO—O—, —O—COL 1 -, —CO—OL 1 -, —O—CO—OL 1 -, —CO—CH═CH—, —CH═CH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH, or —CH 2 ═N—N═CH 2 —,
L 1 represents an alkylene group of 1 to 8 carbon atoms, the alkylene group may be branched and may be substituted with a halogen atom or a cyano group, and the alkylene group represented by L 1 may be interrupted by —O—, —CH═CH—, or —C≡C—,
Y 1 , Y 2 , Y 3 , and Y 4 each independently represent an alkyl group of 1 to 6 carbon atoms, a halogen atom, or a cyano group, a hydrogen atom of the alkyl group represented by each of Y 1 , Y 2 , Y 3 and Y 4 may be substituted with a halogen atom or a cyano group, and a methylene chain in the alkyl group represented by each of Y 1 , Y 2 , Y 3 and Y 4 may be interrupted by —O— or —CO—,
a, b, c, and d are each independently from 0 to 8, and f, g, and h are each independently 0 or 1,
j and k are each independently 0, 1, or 2, provided that j+k≧2, and
G 1 and G 2 each independently represent a substituent selected from the group consisting of substituents represented by formulae (1) to (4):

wherein in formula (1), M 1 represents a hydrogen atom, a methyl group, or a halogen atom; in formula (2), R 1 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; in formula (3), R 2 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; and in formula (4), R 3 represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms.

3. The polymerizable liquid crystal composition according to claim 1 , wherein the colorant as the component (B) is a fluorescent dye.

4. The polymerizable liquid crystal composition according to claim 1 , wherein the colorant as the component (B) is a fluorescent dye having a luminophore and a mesogenic structure.

5. A polarized light-emitting coating material comprising the polymerizable liquid crystal composition according to claim 1 .

6. A polarized light-emitting laminate comprising a support

Assignees

• Kubota Yusuke
• Irisawa Masatomi
• Yano Toru
• Matsumoto Ken
• Adeka Corp

Inventors

• Kubota Yusuke
• Irisawa Masatomi
• Yano Toru
• Matsumoto Ken

Classifications

• C09K19/60

  Pleochroic dyes · CPC title

• C07D265/38

  [b, e]-condensed with two six-membered rings · CPC title

• C09K19/32 Primary

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C09K19/3483

  the heterocyclic ring being a non-aromatic ring · CPC title