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

Patent metadata

Field	Value
Publication number	US-2016145363-A1
Application number	US-201514920294-A
Country	US
Kind code	A1
Filing date	Oct 22, 2015
Priority date	Apr 27, 2011
Publication date	May 26, 2016
Grant date	—

Abstract

The present invention relates to a polymerizable compound represented by a formula (I). The present invention provides a polymerizable compound, a polymerizable composition, a polymer, and an optically anisotropic article that are capable of obtaining an optical film having a low melting point, having excellent solubility, capable of being manufactured at low cost, and capable of uniform polarized light conversion across a broad wavelength region. [In formula: Y 1 to Y 6 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O— etc.; G 1 and G 2 are independently a divalent C1-C20 aliphatic group etc.; Z 1 and Z 2 are independently C2-C10 alkenyl group that is substituted with a halogen atom etc.; A x is a C2-C30 organic group that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and an aromatic hetero ring; A y is a hydrogen atom, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C3-C12 cycloalkyl group etc.; A 1 is a trivalent aromatic group etc.; A 2 and A 3 are independently a divalent C6-C30 aromatic group etc.; and Q 1 is a hydrogen atom, or a C1-C6 alkyl group etc.]

First claim

1 . A polymerizable compound represented by any one of formulas 1 to 34.

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

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

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

5 . A polymer obtained by polymerizing the polymerizable composition according to claim 2 .

6 . The polymer according to claim 4 , the polymer being a liquid crystalline polymer.

7 . An optically anisotropic article comprising the polymer according to claim 5 .

8 . A hydrazine compound represented by a formula (3)

wherein 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 an aromatic hetero ring, and
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, —C(═O)—R 3 , —SO 2 —R 6 , 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 an aromatic hetero ring, provided that
the aromatic ring included in A x and A y is substituted or unsubstituted, and
A x and A y optionally bond to each other to form a 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, or a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, R 6 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.

9 . The hydrazine compound according to claim 8 , wherein A x is an aromatic group having 4 to 30 carbon atoms, and A y be a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, or an alkyl group having 1 to 20 carbon atoms that is optionally substituted with a halogen atom, a cyano group, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms.

10 . The hydrazine compound according to claim 8 , wherein the aromatic ring is 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, and a thiazole ring; fused aromatic hetero rings such as a benzothiazole ring, a benzoxazole ring, a quinoline ring, a phthalazine ring, a benzimidazole ring, a benzopyrazole ring, a benzofuran ring, or a benzothiophene ring.

11 . The hydrazine compound according to claim 8 , wherein A x is represented by any one of following formulas that is optionally substituted with halogen atoms, alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkyl halide groups having 1 to 6 carbon atoms, substituted amino groups, alkoxy groups having 1 to 6 carbon atoms, a nitro group; aryl groups, —C(═O)—R 4 ; —C(═O)—OR 4 ; —SO 2 R 4 , R 4 is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, and
X and Y are independently NR 5 , an oxygen atom, a sulfur atom, —SO—, or —SO 2 —, and R 5 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

12 . The hydrazine compound according to claim 11 ,
wherein A x is represented by any one of following formulas, and

A y is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, or an alkyl group having 1 to 20 carbon atoms that is optionally substituted with a halogen atom, a cyano group, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms.

13 . The polymerizable compound according to claim 1 , wherein a total number of it electrons included in A x and A y is 4 to 24.

14 . A method for producing an optically anisotropic article comprising the steps of:
obtaining a polymerizable compound by reacting a hydrazine compound according to claim 8 with a carbonyl compound; forming an alignment film on a substrate; and forming a liquid crystal layer on the alignment film using the polymer obtained by polymerizing the polymerizable compound or a polymerizable composition including the polymerizable compound and an initiator.

15 . A method for producing a polymerizable compound represented by a formula (I),

the method comprising reacting a hydrazine compound according to claim 8 with a carbonyl compound represented by a formula (4),

wherein Y 1 to Y 6 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 adjacent —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 trivalent aromatic group,
A 2 and A 3 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.

16 . The method for producing a polymerizable compound according to claim 15 , wherein the hydrazine compound is reacted with the carbonyl compound in a molar ratio of 1:2 to 2:1.

17 . A hydrazine compound represented by any one of formulas (H), (J), (L), (S), (N), (U), (W), (Y), (a), (h), (j), (m), and (n).

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Okuyama Kumi

Classifications

• C07C243/20 Primary

  having nitrogen atoms of hydrazine groups bound to carbon atoms of rings other than six-membered aromatic rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• G02B5/3083

  Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001) · CPC title

• C07D277/82

  Nitrogen atoms · CPC title

• C07C251/86 Primary

  having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings · CPC title