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

Patent metadata

Field	Value
Publication number	US-10647794-B2
Application number	US-201514920294-A
Country	US
Kind code	B2
Filing date	Oct 22, 2015
Priority date	Apr 27, 2011
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

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

First claim

The invention claimed is:

1. 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, a pyrrole ring, a furan ring, a thiophene ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzoxazole ring, a quinoline ring, a benzimidazole ring, a benzopyrazole ring, a benzofuran ring, and a benzothiophene ring, and
A y is an alkyl group having 5 to 20 carbon atoms that is optionally substituted with halogen atoms, substituted amino groups, alkoxy groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms that are substituted with an alkoxy group having 1 to 6 carbon atoms, a nitro group, aryl groups, cycloalkyl groups having 3 to 8 carbon atoms, —C(═O)—R 4 ; —C(═O)—OR 4 ; —S0 2 R 4 , a hydroxyl group, where R 4 is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, —C(═O)—R 3 , or —SO 2 —R 6 , provided that
the aromatic ring included in A x 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.

2. The hydrazine compound according to claim 1 , wherein A x is an aromatic group having 4 to 30 carbon atoms, and A y be an alkyl group having 5 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.

3. The hydrazine compound according to claim 1 , 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.

4. The hydrazine compound according to claim 3 ,
wherein A x is represented by any one of following formulas, and

A y is an alkyl group having 5 to 20 carbon atoms that is optionally substituted with a halogen atom, an alkoxy group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms.

5. A method for producing an optically anisotropic article comprising the steps of:
obtaining a polymerizable compound by reacting a hydrazine compound according to claim 1 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.

6. A hydrazine compound represented by any one of formulas (H), (J), (S), (W), (Y), (j), and (n)

7. The hydrazine compound according to claim 1 , wherein a total number of π electrons included in A x and A y is 4 to 24.

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Okuyama Kumi

Classifications

• C09K19/38

  Polymers · 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

• C08F22/22

  Esters containing nitrogen · CPC title

• C07C243/20 Primary

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

• C07D237/34

  with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals · CPC title