Polymerizable compound, polymerizable composition, polymer, and optically anisotropic substance

Patent metadata

Field	Value
Publication number	US-9776954-B2
Application number	US-201314436526-A
Country	US
Kind code	B2
Filing date	Oct 16, 2013
Priority date	Oct 19, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention relates to: a polymerizable compound represented by a formula (I); a polymerizable composition comprising the polymerizable compound and an initiator; a polymer obtained by polymerizing the polymerizable compound or the polymerizable composition; and an optically anisotropic article comprising the polymer [in the formula, Y 1 to Y 8 are a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or the like; G 1 and G 2 are a divalent aliphatic group having 1 to 20 carbon atoms, or the like; Z 1 and Z 2 are an alkenyl group having 2 to 10 carbon atoms, or the like; A 1 is a tetravalent aromatic group, or the like; A 2 and A 3 are a divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms, or the like; A 4 and A 5 are a divalent aromatic group having 4 to 30 carbon atoms, or the like; A x1 and A x2 are an organic group having 2 to 30 carbon atoms that includes an aromatic ring, or the like; A y1 and A y2 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or the like; Q 1 and Q 2 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or the like; and m and n are 0 or 1]. According to the present invention, a polymerizable compound, a polymerizable composition, and a polymer that have a practical low melting point, exhibit excellent solubility in a general-purpose solvent, can be produced at low cost, and can produce an optical film that achieves uniform conversion of polarized light over a wide wavelength band, and also provide an optically anisotropic article.

First claim

The invention claimed is:

1. A polymerizable compound represented by a formula (I),

wherein Y 1 to Y 8 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—, —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 contiguous —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 1 is a substituted or unsubstituted tetravalent aromatic group having 4 to 30 carbon atoms,
A 2 and A 3 are independently a substituted or unsubstituted divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms,
A 4 and A 5 are independently a substituted or unsubstituted divalent aromatic group having 4 to 30 carbon atoms,
A x1 and A x2 are independently an organic group having 2 to 30 carbon atoms that includes at least one ring selected from a group consisting of a hydrocarbon ring and a heterocyclic ring,
A y1 and A y2 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an organic group having 2 to 30 carbon atoms that includes at least one ring selected from a group consisting of a hydrocarbon ring and a heterocyclic ring, provided that the ring included in A x1 , the ring included in A x2 , the ring optionally included in A y1 , and the ring optionally included in A y2 are either substituted or unsubstituted,
A x1 and A y1 are optionally bonded to each other to form a ring, and A x2 and A y2 are optionally bonded to each other to form a ring,
Q 1 and Q 2 are independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and
m and n are independently 0 or 1.

2. The polymerizable compound according to claim 1 , wherein the ring included in A y1 , the ring included in A x2 , the ring optionally included in A y1 , and the ring optionally included in A y2 are an aromatic ring.

3. The polymerizable compound according to claim 1 , wherein a total number of aromatic ring π electrons included in A x1 and A y1 is 24 or less, and a total number of aromatic ring π electrons included in A x2 and A y2 is 24 or less.

4. The polymerizable compound according to claim 1 , wherein the ring that is optionally formed by A x1 and A y1 , and the ring that is optionally formed by A x2 and A y2 , are a nitrogen-containing heterocyclic ring represented by a formula (II),

wherein R x are a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, provided that are either identical or different, an arbitrary C—R″ linkage that forms the ring is optionally substituted with N—R 3 (R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) or —O—, and the ring optionally includes an unsaturated bond, a is an integer from 0 to 2, and “-” is a bonding position.

5. The polymerizable compound according to claim 1 , wherein A 1 is a substituted or unsubstituted tetravalent benzene ring group, or a substituted or unsubstituted tetravalent naphthalene ring group, and A 4 and A 5 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 8 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 contiguous —O— is excluded.

9. The polymerizable compound according to claim 1 , wherein Y 1 to Y 8 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—, Z 1 and Z 2 are independently CH 2 ═CH—, CH 2 ═C(CH 3 )—, or CH 2 ═C(Cl)—, and 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 Y 1 to Y 8 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—.

16. The polymerizable compound according to claim 3 , wherein Y 1 to Y 8 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—.

17. The polymerizable compound according to claim 4 , wherein Y 1 to Y 8 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—.

18. The polymerizable compound according to claim 5 , wherein Y′ to Y 8 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—, or —O—C(═O)—O—.

19. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 2 .

20. A polymer obtained by polymerizing the polymerizable composition according to claim 10 .

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Kiriki Satoshi
• Okuyama Kumi

Classifications

• C08F22/22

  Esters containing nitrogen · CPC title

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title

• C07D295/30

  non-acylated · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C07C251/88

  having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines · CPC title