Polymerizable compound, polymerizable composition, polymer, and optical anisotropic body

Patent metadata

Field	Value
Publication number	US-9777096-B2
Application number	US-201314437748-A
Country	US
Kind code	B2
Filing date	Oct 16, 2013
Priority date	Oct 23, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention pertains 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. The present invention provides 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 x is a group represented by a formula (II),

wherein X is a nitrogen atom or a carbon atom, and R a and R b are independently 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 18 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaromatic ring group having 1 to 20 carbon atoms,
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, or the group represented by the formula (II),
A 1 is a substituted or unsubstituted trivalent aromatic group,
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,
Q 1 is 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 R a and R b in the formula (II) are independently 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 18 carbon atoms, or a group among groups respectively represented by formulas (II-1) to (II-5),

wherein X a is a nitrogen atom or a carbon atom, 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, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, a monosubstituted amino group, a disubstituted amino group, an alkylsulfamoyl group having 1 to 6 carbon atoms, a dialkylsulfamoyl group having 2 to 12 carbon atoms, or —C(═O)—O—R 6 , and R 6 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, provided that R X are either identical or different, and an arbitrary C—R X linkage is optionally substituted with a nitrogen atom.

3. 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 4 and A 5 are independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

4. 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—.

5. 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)—.

6. 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.

7. The polymerizable compound according to claim 1 , wherein G 1 and G 2 are independently an alkylene group having 1 to 12 carbon atoms.

8. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 1 .

9. A polymerizable composition comprising the polymerizable compound according to claim 1 , and an initiator.

10. A polymer obtained by polymerizing the polymerizable compound according to claim 1 .

11. The polymer according to claim 10 , the polymer being a liquid crystalline polymer.

12. An optically anisotropic article comprising the polymer according to claim 11 .

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

14. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 3 .

15. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 4 .

16. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 5 .

17. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 6 .

18. A polymerizable composition comprising at least one type of the polymerizable compound according to claim 7 .

19. A polymerizable composition comprising the polymerizable compound according to claim 2 , and an initiator.

20. A polymer obtained by polymerizing the polymerizable composition according to claim 8 .

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Kiriki Satoshi
• Okuyama Kumi

Classifications

• G02B1/08

  made of polarising materials · CPC title

• C07D277/50

  Nitrogen atoms bound to hetero atoms · 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

• G02B1/04

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

• C07D277/20 Primary

  having two or three double bonds between ring members or between ring members and non-ring members · CPC title