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

Patent metadata

Field	Value
Publication number	US-10487065-B2
Application number	US-201816176325-A
Country	US
Kind code	B2
Filing date	Oct 31, 2018
Priority date	Jul 9, 2012
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

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.

First claim

The invention claimed is:

1. A method for producing a polymerizable compound represented by a formula (I), the method comprising reacting a carbonyl compound represented by a formula (4),

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 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,
with a hydrazine compound represented by the following formula,

wherein A x is an organic group having 3 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 2 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 3 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,

wherein A x and A y are the same as defined above,
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 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.

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

• G02B5/30

  Polarising elements (light-modulating devices with active elements G02F1/00) · CPC title

• C08F22/24

  Esters containing sulfur · CPC title

• C08F20/36 Primary

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C07C249/16

  of hydrazones · CPC title