Intermediate for manufacture of polymerizable compound and process for manufacture thereof

Patent metadata

Field	Value
Publication number	US-9447059-B2
Application number	US-201214347962-A
Country	US
Kind code	B2
Filing date	Apr 27, 2012
Priority date	Sep 27, 2011
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

The present invention pertains to a compound represented by a formula (I) and a method for producing thereof (in the formula, 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, A y is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, an alkenyl group having 2 to 18 carbon atoms, 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, or the like. A x and A y optionally bond to each other to form a ring, and Q is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or the like.). According to the invention, provided are a novel compound that makes it possible to produce an optical film that achieves uniform conversion of polarized light over a wide wavelength band can be inexpensively produced in high yield by utilizing the compound according to one aspect of the invention as an intermediate for producing the polymerizable compound, and a method for producing thereof.

First claim

The invention claimed is:

1. A compound represented by a formula (I),

wherein A x is an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from the group consisting of an anthracene ring, a fluorene ring, a pyridazine ring, a benzothiophene ring, a benzofuran ring, a benzoxazole ring, a phthalazine ring, and a carbazole ring,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms, or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from the 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, and
Q is a hydrogen atom.

2. The compound according to claim 1 , wherein a total number of aromatic ring π-electrons included in A x and A y is 24 or less.

3. The compound according to claim 1 , wherein A y is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

4. A method for producing a hydrazone compound represented by a formula (I), the method comprising reacting a carbonyl compound represented by a formula (II) with a hydrazine compound represented by a formula (III) in a solvent,

wherein Q is a hydrogen atom,

wherein A x is an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from the group consisting of an anthracene ring, a fluorene ring, a pyridazine ring, a benzothiophene ring, a benzofuran ring, a benzoxazole ring, a phthalazine ring, and a carbazole ring,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms, or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from the 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,

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

5. The method according to claim 4 , wherein the solvent is an alcohol-based solvent.

6. The method according to claim 5 , wherein the alcohol-based solvent is an alcohol-based solvent having 1 to 4 carbon atoms.

7. The compound according to claim 2 , wherein A y is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

8. A compound represented by a formula (I),

wherein A x is an aromatic group selected from the group consisting of a naphthalene group, an anthracene group, a fluorene group, a pyrrole group, a furan group, a thiophene group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a benzimidazole group, a benzothiophene group, a benzofuran group, a benzothiazole group, a benzoxazole group, a quinoline group, a phthalazine group, and a carbazole group,
wherein the naphthalene group, the anthracene group, the fluorene group, the pyrrole group, the furan group, the thiophene group, the pyrazole group, the imidazole group, the thiazole group, the pyridine group, the pyridazine group, the pyrimidine group, the pyrazine group, the benzimidazole group, the benzothiophene group, the benzofuran group, the benzothiazole group, the benzoxazole group, the phthalazine group, and the carbazole group are optionally substituted with one substituent or a plurality of identical or different substituents selected from a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyl halide group having 1 to 6 carbon atoms, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, a nitro group, an aryl group, a —C(═O)—OR group, or an —SO 2 R group, and R is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms,
the oxazole group is optionally substituted with one substituent or a plurality of identical or different substituents selected from a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyl halide group having 1 to 6 carbon atoms, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a —C(=O)—OR group, or an —SO 2 R group, and R is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms,
the quinoline group is optionally substituted with one substituent or a plurality of identical or different substituents selected from a cyano group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyl halide group having 1 to 6 carbon atoms, a substituted amino group, an alkoxy group having 1 to 6 carbon atoms, a nitro group, an aryl group, a —C(═O)—OR group, or an —SO 2 R group, and R is an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms, or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic hetero ring, provided that the aromatic ring included in A y is substituted or unsubstituted, and A x and A y optionally bond to each other to form a ring, and
Q is a hydrogen atom.

9. The compound according to claim 8 , wherein the compound is selected from the group consisting of compounds (I-1) to (I-3) and (I-5) to (I-16):

Assignees

• Sakamoto Kei
• Okuyama Kumi
• Nakano Yasushi
• Zeon Corp

Inventors

• Sakamoto Kei
• Okuyama Kumi
• Nakano Yasushi

Classifications

• C07D215/38

  Nitrogen atoms (nitro radicals C07D215/18) · CPC title

• C07D263/58

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2 · CPC title

• C08G65/4062

  in ring structure · CPC title

• C07D237/34

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

• C08L71/12

  Polyphenylene oxides · CPC title