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

Patent metadata

Field	Value
Publication number	US-9856333-B2
Application number	US-201615338987-A
Country	US
Kind code	B2
Filing date	Oct 31, 2016
Priority date	May 30, 2012
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present invention relates to: a polymerizable compound (I), wherein Y 1 to Y 6 are a chemical single bond, —O—C(═O)—, —C(═O)—O— or the like, G 1 and G 2 are a divalent aliphatic group, Z 1 and Z 2 are an alkenyl group, A x is a fused ring group represented by a formula (II), wherein X is —NR 3 —, an oxygen atom, a sulfur atom or the like, R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and D is a substituted or unsubstituted ring having 1 to 20 carbon atoms that includes at least one nitrogen atom, A y is a hydrogen atom, an alkyl group, A 1 is a trivalent aromatic group or the like, A 2 and A 3 are a divalent aromatic group having 6 to 30 carbon atoms or the like, and Q 1 is a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms.

First claim

The invention claimed is:

1. A hydrazine compound represented by a formula (3),

wherein A x is a fused ring group represented by any one of formulas (II-1) to (II-5) and (Ex-6),

wherein X is —NR 3 —, an oxygen atom, a sulfur atom, —C(═O)—, —SO—, or —SO 2 —, R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, at least one C—R X in each formula is substituted with a nitrogen atom, each R X is 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 , provided that R X are either identical or different,
A y is
a hydrogen atom,
a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substitutable with at least one of a halogen atom, a cyano group, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms, a nitro group, an aryl group, a cycloalkyl group having 3 to 8 carbon atoms, —C(═O)—R 6 , —C(═O)—O—R 6 , —SO 2 R 6 , or a hydroxyl group,
a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substitutable with at least one of a halogen atom, a cyano group, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms, a nitro group, an aryl group, a cycloalkyl group having 3 to 8 carbon atoms, —C(═O)—R 6 , —C(═O)—O—R 6 , —SO 2 R 6 , or a hydroxyl group,
a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, substitutable with at least one of a halogen atom, a cyano group, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms, a nitro group, an aryl group, a cycloalkyl group having 3 to 8 carbon atoms, —C(═O)—R 6 , —C(═O)—O—R 6 , —SO 2 R 6 , or a hydroxyl group,
—C(═O)—R 4 , —SO 2 —R 5 , or
an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a quinoline ring, a phthalazine ring, a benzimidazole ring, a benzopyrazole ring, a benzofuran ring, and a benzothiophene ring, provided that the aromatic ring is either substituted or unsubstituted,
R 4 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, or a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, R 5 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 6 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

2. The hydrazine compound according to claim 1 , wherein A x is represented by any one of following formulas and A y is an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms, and Rx is the same as defined above.

3. A method for producing an optically anisotropic article, comprising:
reacting the hydrazine compound according to claim 1 with a carbonyl compound for preparing a polymerizable compound;
forming a liquid crystal layer including a polymer by polymerizing the polymerizable compound or a polymerizable composition containing the polymerizable compound and an initiator on a substrate having an alignment film.

4. A method for producing a polymerizable compound comprising reacting the hydrazine compound according to claim 1 with a precursor compound of said polymerizable compound.

5. The method according to claim 4 , wherein the polymerizable compound is a liquid crystalline compound.

6. The method according to claim 4 , wherein the hydrazine compound is represented by a formula (P) or (E).

7. The method according to claim 6 , wherein the polymerizable compound is a liquid crystalline compound.

8. A hydrazine compound represented by a formula (J), (K), (M), or (S).

9. A method for producing an optically anisotropic article, comprising:
reacting the hydrazine compound according to claim 8 with a carbonyl compound for preparing a polymerizable compound;
forming a liquid crystal layer including a polymer formed by polymerizing the polymerizable compound or a polymerizable composition containing the polymerizable compound and an initiator on a substrate having an alignment film.

10. A method for producing a polymerizable compound comprising reacting the hydrazine compound according to claim 8 with a precursor compound of said polymerizable compound.

11. The method according to claim 10 , wherein the polymerizable compound is a liquid crystalline compound.

12. A method for producing an optically anisotropic article, comprising:
reacting the hydrazine compound represented by a formula (P) or (E) with a carbonyl compound for preparing a polymerizable compound;
forming a liquid crystal layer including a polymer formed by polymerizing the polymerizable compound or a polymerizable composition containing the polymerizable compound and an initiator on a substrate having an alignment film.

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Okuyama Kumi

Classifications

• C08F222/1025

  of aromatic dialcohols · 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

• C08F122/24

  Esters containing sulfur · CPC title

• C09K19/348

  containing at least two nitrogen atoms · CPC title

• C09K19/3852

  Poly(meth)acrylate derivatives · CPC title