Polymerizable optically active imide compound and polymerizable composition containing the compound
A polymerizable optically-active imide compound represented by the following general formula (I). Preferable among the polymerizable optically-active imide compound are compounds wherein X 3 and X 4 in general formula (I) are both —CO—, compounds wherein the rings A 2 and A 3 in general formula (I) are both naphthalene rings, compounds wherein the rings A 1 , A 2 , A 3 , and A 4 are all benzene rings, compounds wherein M 1 and M 2 in general formula (I) are both hydrogen atoms, or compounds wherein rings A 1 and A 4 , as well as rings A 2 and A 3 , in general formula (I) are the same ring, the groups M 1 and M 2 , X 1 and X 6 , X 2 and X 5 , as well as X 3 and X 6 are the same group in each pair, and n and m are the same number.
1. A polymerizable optically-active imide compound represented by general formula (I):
wherein,
rings A 1 , A 2 , A 3 , and A 4 each independently represent a benzene ring or a naphthalene ring, wherein a carbon atom in the benzene ring and the naphthalene ring may optionally be substituted by a nitrogen atom;
M 1 and M 2 each independently represent a hydrogen atom or a methyl group;
R 1 represents a C 1-10 alkyl group, a C 6-20 aryl group, or a C 7-20 arylalkyl group;
a hydrogen atom in R 1 may optionally be substituted by a halogen atom;
a methylene group in R 1 may be interrupted by —O—, —COO—, or —OCO—;
X 1 represents a direct bond, -L 1 -, -L 1 O—, -L 1 O—CO—, -L 1 CO—O—, or -L 1 O—CO—O—;
X 2 and X 5 each independently represent a linking group consisting of a direct bond, an ester bond, an ether bond, a C 1-8 alkylene group that may be branched and that may have an unsaturated bond, or a combination thereof;
X 3 represents a direct bond, —CO—, -L 2 -, —OL 2 -, —O—COL 2 -, —CO—OL 2 -, or —O—CO—OL 2 -;
X 4 represents a direct bond, —CO—, -L 1 -, -L 1 O—, -L 1 O—CO—, -L 1 CO—O—, or -L 1 O—CO—O—;
X 6 represents a direct bond, -L 2 -, —OL 2 -, —O—COL 2 -, —CO—OL 2 -, or —O—CO-OL 2 -;
L 1 and L 2 each independently represent a C 1-8 alkylene group that may be branched, wherein the C 1-8 alkylene group may be interrupted one to three times by an oxygen atom; and
n and m each independently represent 0 or 1.
2. The polymerizable optically-active imide compound according to claim 1 , wherein each of X 3 and X 4 in general formula (I) is —CO—.
3. The polymerizable optically-active imide compound according to claim 1 , wherein each of rings A 2 and A 3 in general formula (I) is a naphthalene ring.
4. The polymerizable optically-active imide compound according to claim 1 , wherein each of rings A 1 , A 2 , A 3 , and A 4 in general formula (I) is a benzene ring.
5. The polymerizable optically-active imide compound according to claim 1 , wherein each of M 1 and M 2 in general formula (I) is a hydrogen atom.
6. The polymerizable optically-active imide compound according to claim 1 , wherein, in general formula (I), rings A 1 and A 4 , as well as rings A 2 and A 3 , are the same ring, groups M 1 and M 2 , X 1 and X 6 , X 2 and X 5 , as well as X 3 and X 6 are the same group in each pair, and n and m are the same number.
7. A polymerizable composition comprising the polymerizable optically-active imide compound according to claim 1 .
8. The polymerizable composition according to claim 7 , further comprising a liquid crystal compound.
9. The polymerizable composition according to claim 8 , wherein the polymerizable optically-active imide compound is present at a concentration of to 50 parts by mass when a total of the polymerizable optically-active imide compound and the liquid crystal compound is 100 parts by mass.
10. The polymerizable composition according to claim 8 , wherein the liquid crystal compound has a polymerizable functional group.
11. The polymerizable composition according to claim 7 , wherein the composition exhibits a cholesteric phase.
12. A polymer prepared by photopolymerization of the polymerizable composition according to claim 7 .
13. The polymer according to claim 12 , wherein the polymer exhibits optical anisotropy.
14. An optical film made using the polymer according to claim 12 .
15. An optical retardation compensation material for liquid crystal displays, made using the optical film according to claim 14 .
16. A cut-off filter made using the optical film according to claim 14 .
17. The polymerizable optically-active imide compound according to claim 2 , wherein each of rings A 2 and A 3 in general formula (I) is a naphthalene ring.
18. The polymerizable optically-active imide compound according to claim 2 , wherein each of rings A 1 , A 2 , A 3 , and A 4 in general formula (I) is a benzene ring.
19. The polymerizable optically-active imide compound according to claim 2 , wherein each of M 1 and M 2 in general formula (I) is a hydrogen atom.
20. The polymerizable optically-active imide compound according to claim 3 , wherein each of M 1 and M 2 in general formula (I) is a hydrogen atom.
21. The polymerizable optically-active imide compound according to claim 1 , wherein R 1 in general formula (I) represents a C 1-10 alkyl group or a C 7-20 arylalkyl group.
22. The polymerizable optically-active imide compound according to claim 1 , wherein R 1 in general formula (I) represents methyl, ethyl, propyl, butyl, amyl or benzyl.
23. The polymerizable optically-active imide compound according to claim 1 , selected from the group consisting of: