Polymerizable compound, polymerizable composition, polymer, optically anisotropic body, and method for producing polymerizable compound

Patent metadata

Field	Value
Publication number	US-9586917-B2
Application number	US-201314413787-A
Country	US
Kind code	B2
Filing date	May 30, 2013
Priority date	Jul 9, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

A polymerizable compound has a practical low melting point, excellent solubility in a general-purpose solvent, and can produce an optical film at low cost, exhibits low reflected luminance, and achieves uniform conversion of polarized light over a wide wavelength band, an optically anisotropic article. A carbonyl compound is useful as a raw material for producing the polymerizable compound. (In the formula (I), Y 1 to Y 8 represent —C(═O)—O—, G 1 and G 2 represent a C 1-20 divalent linear aliphatic group, Z 1 and Z 2 represent a C 2-10 alkenyl group that is unsubstituted, or substituted with a halogen atom, A x represents a C 2-30 organic group with at least one aromatic ring, A y represents a hydrogen atom or C 1-20 alkyl group, A 1 represents a trivalent aromatic group, A 2 and A 3 represent a C 3-30 divalent alicyclic hydrocarbon group, A 4 and A 5 represent a C 6-30 divalent aromatic group or the like, and Q 1 represents a hydrogen atom.)

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 linear 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 unsubstituted, or substituted with a halogen atom,
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 a heteroaromatic 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 alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, —C(═O)—R 3 , —SO 2 —R 4 , —C(═S)NH—R 9 , 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 a heteroaromatic 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, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 5 to 12 carbon atoms, R 4 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, R 9 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, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted aromatic group having 5 to 20 carbon atoms,
provided that the aromatic ring included in A x and A y is substituted or unsubstituted, and
A x and A y are optionally bonded to each other to form a ring,
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 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 1 is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring 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 at least one type of the polymerizable compound according to claim 1 , and an initiator.

10. The polymerizable compound according to claim 1 , wherein A 2 and A 3 are independently represented by formula (A32a) or (A32b)

11. The polymerizable compound according to claim 1 , wherein A 4 and A 5 are independently represented by any one of formulae (A41) to (A43)

12. A polymerizable compound represented by any one of compounds 1 to 52

13. The polymerizable compound according to claim 1 , wherein A x is represented by any one of following formulae,

in which X, is NR 7 , an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, provided that a case where two or more oxygen atoms, sulfur atoms, —SO—, or —SO 2 — are situated at contiguous positions is excluded,
R 7 is a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms A y is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms that is optionally substituted with a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms,

a heteroaromatic ring group having 3 to 9 carbon atoms that is optionally substituted with a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group,
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 alkynyl group having 2 to 20 carbon atoms,
wherein a substituent that may substitute the alkyl group, the alkenyl group, or the alkynyl group is a halogen atom, a cyano group, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Kiriki Satoshi
• Okuyama Kumi
• TAIRA Kanako

Classifications

• C08F22/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C07D417/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C09K2019/0414

  containing a heterocyclic ring · CPC title

• C08F22/20

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C08F28/06

  by a heterocyclic ring containing sulfur · CPC title