Polymerizable compound, polymerizable composition, polymer, and optically anisotropic body
The present invention relates to a polymerizable compound represented by a formula (I). The present invention provides a polymerizable compound, a polymerizable composition, a polymer, and an optically anisotropic article that are capable of obtaining an optical film having a low melting point, having excellent solubility, capable of being manufactured at low cost, and capable of uniform polarized light conversion across a broad wavelength region. [In formula: Y 1 to Y 6 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O— etc.; G 1 and G 2 are independently a divalent C1-C20 aliphatic group etc.; Z 1 and Z 2 are independently C2-C10 alkenyl group that is substituted with a halogen atom etc.; A x is a C2-C30 organic group that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and an aromatic hetero ring; A y is a hydrogen atom, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C3-C12 cycloalkyl group etc.; A 1 is a trivalent aromatic group etc.; A 2 and A 3 are independently a divalent C6-C30 aromatic group etc.; and Q 1 is a hydrogen atom, or a C1-C6 alkyl group etc.]
1. A polymerizable compound represented by a formula (I),
wherein Y 1 to Y 6 are independently a chemical single bond, —O—, —S—, —O—C(═O)—, —C(═O)—O—, —O—C(═O)—O—, —NR 1 —C(═O)—, —C(═O)—NR 1 —, —O—C(═O)—NR 1 —, —NR 1 —C(═O)—O—, —NR 1 —C(═O)—NR 1 —, —O—NR 1 —, or —NR 1 —O—, R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, G 1 and G 2 are independently a substituted or unsubstituted divalent aliphatic group having 1 to 20 carbon atoms that optionally includes —O—, —S—, —O—C(═O)—, —C(═O)—O—, —NR 2 —C(═O)—, —C(═O)—NR 2 —, —NR 2 —, or —C(═O)—, provided that a case where the aliphatic group includes two or more adjacent —O— or —S— is excluded, R 2 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Z 1 and Z 2 are independently an alkenyl group having 2 to 10 carbon atoms that is substituted with a halogen atom, or unsubstituted,
A x is an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and an aromatic hetero ring,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, —C(═O)—R 3 , —SO 2 —R 6 , or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and an aromatic hetero ring, provided that the aromatic ring included in A x and A y is substituted or unsubstituted, and
A x and A y optionally bond to each other to form a ring, R 3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, R 6 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a phenyl group, or a 4-methylphenyl group,
A 1 is a substituted or unsubstituted trivalent aromatic group,
A 2 and A 3 are independently a substituted or unsubstituted divalent aromatic group having 6 to 30 carbon atoms, and
Q 1 is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
2. The polymerizable compound according to claim 1 , wherein a total number of π electrons included in A x and A y is 4 to 24.
3. The polymerizable compound according to claim 1 , wherein A x is a substituted or unsubstituted group among groups represented by the following structural formulas,
wherein X is NR 5 , an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, provided that a case where oxygen atoms, sulfur atoms, —SO—, or —SO 2 — are situated at adjacent positions is excluded, and R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
4. The polymerizable compound according to claim 1 , wherein A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a group represented by —C(═O)—R 3 (wherein R 3 is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms), or a group represented by —SO 2 —R 6 (wherein R 6 is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a phenyl group, or a 4-methylphenyl group).
5. The polymerizable compound according to claim 1 , wherein A 1 is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group, and A 2 and A 3 are independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
6. The polymerizable compound according to claim 1 , wherein Y 1 to Y 6 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—.
7. The polymerizable compound according to claim 1 , wherein Z 1 and Z 2 are independently CH 2 ═CH—, CH 2 ═C(CH 3 )—, or CH 2 ═C(Cl)—.
8. The polymerizable compound according to claim 1 , wherein G 1 and G 2 are independently a substituted or unsubstituted divalent aliphatic group having 1 to 12 carbon atoms that optionally includes —O—, —O—C(═O)—, —C(═O)—O—, or —C(═O)—, provided that a case where the aliphatic group includes two or more adjacent —O— is excluded.
9. The polymerizable compound according to claim 1 , wherein G 1 and G 2 are independently a divalent alkylene group having 1 to 12 carbon atoms.
10. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 1 .
11. A polymerizable composition comprising the polymerizable compound according to claim 1 , and an initiator.
12. A polymer obtained by polymerizing the polymerizable compound according to claim 1 .
13. The polymer according to claim 12 , the polymer being a liquid crystalline polymer.
14. An optically anisotropic article comprising the polymer according to claim 13 .
15. The polymerizable compound according to claim 2 , wherein A x is a substituted or unsubstituted group among groups represented by the following structural formulas,
wherein X is NR 5 , an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, provided that a case where oxygen atoms, sulfur atoms, —SO—, or —SO 2 — are situated at adjacent positions is excluded, and R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
16. The polymerizable compound according to claim 2 , wherein A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a group represented by —C(═O)—R 3 (wherein R 3 is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms), or a group represented by —SO 2 —R 6 (wherein R 6 is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a phenyl group, or a 4-methylphenyl group).
17. The polymerizable compound according to claim 3 , wherein A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a group represented by —C(═O)—R 3 (wherein R 3 is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms), or a group represented by —SO 2 —R 6 (wherein R 6 is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a phenyl group, or a 4-methylphenyl group).
18. The polymerizable compound according to claim 2 , wherein A 1 is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group, and A 2 and A 3 are independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
19. The polymerizable compound according to claim 3 , wherein A 1 is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group, and A 2 and A 3 are independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
20. The polymerizable compound according to claim 4 , wherein A 1 is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group, and A 2 and A 3 are independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.