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

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 and a coating obtained by applying, to the support, the polarized light-emitting coating material according to claim 5 .

7. A polarized light-emitting laminate comprising a polymer obtained by photopolymerization of the polymerizable liquid crystal composition according to claim 1 .

8. A polarizing device comprising the laminate according to claim 6 .

9. A coumarin derivative 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, —NR″R′″, 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 —NR′R′″, 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—, and

at least one of R 111′ to R 116′ represents a substituent represented by formula (V′):

wherein

rings 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 interrupted by —O—,

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′ O—, —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 L 2 may be interrupted by —O—, —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 —O— 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′):

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—.