Naphthobischalcogenadiazole derivative and production method therefor

Patent metadata

Field	Value
Publication number	US-10793584-B2
Application number	US-201716473886-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Dec 27, 2016
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

In order to provide a naphthobischalcogenadiazole derivative that can be used as an intermediate for producing a naphthobischalcogenadiazole compound into which a fluorine atom has been introduced, the naphthobischalcogenadiazole derivative in accordance with an aspect of the present invention is represented by a formula (I):

where each of A 1 and A 2 is independently an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; and each of X 1 and X 2 is independently a hydrogen atom, a halogen atom, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate group, a trifluoroborate salt group, or a triolborate salt group.

First claim

The invention claimed is:

1. A naphthobischalcogenadiazole derivative represented by a formula (I):

where each of A 1 and A 2 is independently an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; and each of X 1 and X 2 is independently a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate group, a trifluoroborate salt group, or a triolborate salt group.

2. The naphthobischalcogenadiazole derivative as set forth in claim 1 , wherein each of A 1 and A 2 is independently an oxygen atom, a sulfur atom, or a selenium atom.

3. The naphthobischalcogenadiazole derivative as set forth in claim 1 , wherein both of A 1 and A 2 are sulfur atoms or selenium atoms.

4. The naphthobischalcogenadiazole derivative as set forth in claim 1 , wherein both of X 1 and X 2 are boronic acid ester groups.

5. The naphthobischalcogenadiazole derivative as set forth in claim 4 , wherein the boronic acid ester group is a boronic acid dialkyl ester group or a boronic acid cyclic ester group.

6. A method for producing a naphthobischalcogenadiazole derivative represented by a formula (I):

where each of A 1 and A 2 is independently an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom; and each of X 1 and X 2 is independently a hydrogen atom, a halogen atom, a boronic acid group, a boronic acid ester group, a boronic acid diaminonaphthalene amide group, an N-methyliminodiacetic acid boronate group, a trifluoroborate salt group, or a triolborate salt group,
said method comprising the step of oxidizing and then reducing diamino-difluoro-dinitronaphthalene or hydrochloride thereof.

7. A method as set forth in claim 6 , said method comprising the steps of:
reducing the diamino-difluoro-dinitronaphthalene or hydrochloride thereof to obtain tetraamino-difluoronaphthalene or hydrochloride thereof;
causing the tetraamino-difluoronaphthalene or hydrochloride thereof to react with a sulfurizing agent, a selenizing agent, or a tellurizing agent to obtain a naphthobischalcogenadiazole derivative; and then
causing the naphthobischalcogenadiazole derivative to react with a halogenating agent or a boronizing agent.

8. A method as set forth in claim 6 , said method comprising the steps of oxidizing and then reducing diamino-difluoro-dinitronaphthalene or hydrochloride thereof, and causing a naphthobischalcogenadiazole derivative, which has been obtained in the above step, to react with a halogenating agent or a boronizing agent.

9. A method as set forth in claim 6 , further comprising the steps of:
producing tetraamino-difluoronaphthalene or hydrochloride thereof by reducing the diamino-difluoro-dinitronaphthalene or hydrochloride thereof; and then
causing the tetraamino-difluoronaphthalene or hydrochloride thereof to react with a sulfurizing agent, a selenizing agent, or a tellurizing agent.

10. A method as set forth in claim 6 , further comprising the step of producing the diamino-difluoro-dinitronaphthalene or hydrochloride thereof by subjecting diamino-difluoronaphthalene or hydrochloride thereof to nitration reaction.

11. A method as set forth in claim 10 , further comprising the step of producing the diamino-difluoronaphthalene or hydrochloride thereof by subjecting difluoronaphthalene to amination reaction.

12. A method as set forth in claim 11 , further comprising the step of producing the difluoronaphthalene by subjecting diaminonaphthalene to fluorination reaction.

13. A method as set forth in claim 9 , further comprising the step of producing the diamino-difluoro-dinitronaphthalene or hydrochloride thereof by subjecting diamino-difluoronaphthalene or hydrochloride thereof to nitration reaction.

14. A method as set forth in claim 13 , further comprising the step of producing the diamino-difluoronaphthalene or hydrochloride thereof by subjecting difluoronaphthalene to amination reaction.

15. A method as set forth in claim 14 , further comprising the step of producing the difluoronaphthalene by subjecting diaminonaphthalene to fluorination reaction.

Assignees

• Univ Osaka
• Ishihara Sangyo Kaisha

Inventors

• Ie Yutaka
• Aso Yoshio
• Seo Takuji
• Moriyama Taichi

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07D517/04

  Ortho-condensed systems · CPC title

• C07D513/04 Primary

  Ortho-condensed systems · CPC title

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title

• H10K10/484

  characterised by the channel regions · CPC title