Fused-ring quinone-substituted polynorbornene, electrode active material and secondary battery

Patent metadata

Field	Value
Publication number	US-10164258-B2
Application number	US-201615064802-A
Country	US
Kind code	B2
Filing date	Mar 9, 2016
Priority date	Oct 8, 2015
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A fused-ring quinone-substituted polynorbornene has recurring units of formula (1) and/or (2) below.

In formulas (1) and (2), A 1 is independently a substituent of formula (3) or (4) below, n is an integer from 1 to 6, and A 2 is a substituent of formula (5) or (6) below.

In formulas (3) to (6), each X is independently a single bond or a divalent group, and Ar 1 and Ar 2 are each independently an aromatic hydrocarbon ring or an oxygen atom or sulfur atom-containing aromatic heterocycle that forms together with two carbon atoms on a benzoquinone skeleton. This polymer has charge-storing properties and, when used as an electrode active material, is capable of providing a high-performance battery possessing high capacity, high rate characteristics and high cycle characteristics.

First claim

The invention claimed is:

1. A fused-ring quinone-substituted polynorbornene having recurring units of formula (1) and/or (2) below

wherein each A 1 is independently a substituent of formula (3) or (4) below, n is an integer from 1 to 6, and A 2 is a substituent of formula (5) or (6) below

wherein each X is independently a single bond or a divalent group, and Ar 1 and Ar 2 are each independently an aromatic hydrocarbon ring or an oxygen atom- or sulfur atom-containing aromatic heterocycle that forms together with two carbon atoms on a benzoquinone skeleton,
provided that when A 1 is a substituent of formula (3) and Ar 1 and/or Ar 2 are benz moieties, the recurring units of formula (1) are recurring units of formula (1-1) below

wherein X is as defined above, R 1 to R 7 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, a substituted or unsubstituted alkyl group of 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 12 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 12 carbon atoms, a substituted or unsubstituted aryl group of 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 12 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted alkylthio group of 1 to 12 carbon atoms, a substituted or unsubstituted monoalkylamino group of 1 to 12 carbon atoms, a dialkylamino group in which each alkyl group is independently a substituted or unsubstituted alkyl group of 1 to 12 carbon atoms, or an alkylcarbonyl group of 2 to 12 carbon atoms, and n 1 is 2.

2. The fused-ring quinone-substituted polynorbornene of claim 1 , wherein the aromatic hydrocarbon ring is a benzene ring and the aromatic heterocycle is a thiophene ring.

3. The fused-ring quinone-substituted polynorbornene of claim 2 which contains recurring units of formula (1-2) and/or (1-3) below

wherein X is as defined above; R 8 to R 17 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, an amino group, a substituted or unsubstituted alkyl group of 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 12 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 12 carbon atoms, a substituted or unsubstituted aryl group of 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 12 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted alkylthio group of 1 to 12 carbon atoms, a substituted or unsubstituted monoalkylamino group of 1 to 12 carbon atoms, a dialkylamino group in which each alkyl group is independently a substituted or unsubstituted alkyl group of 1 to 12 carbon atoms, or an alkylcarbonyl group of 2 to 12 carbon atoms; and n 2 and n 3 are each independently 1 or 2.

4. A charge storage material comprising the fused-ring quinone-substituted polynorbornene according to claim 1 .

5. An electrode active material comprising the charge storage material of claim 4 .

6. An electrode slurry comprising the electrode active material of claim 5 and a solvent.

7. A thin-film comprising the electrode active material of claim 5 .

8. A thin-film produced from the electrode slurry of claim 6 .

9. An electrode comprising the electrode active material of claim 5 .

10. An electrode comprising the thin-film of claim 7 .

11. A secondary battery comprising the electrode of claim 9 .

12. A lithium ion battery comprising the electrode of claim 9 .

13. An air battery comprising the electrode of claim 9 .

Assignees

• Univ Waseda
• Nissan Chemical Ind Ltd

Inventors

• Nishide Hiroyuki
• Oyaizu Kenichi
• Kawai Takuma
• Nakao Satoshi
• Yoshimoto Takuji

Classifications

• C08L65/00

  Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers · CPC title

• H01M12/08

  composed of a half-cell of a fuel-cell type and a half-cell of the secondary-cell type · CPC title

• C08K3/046

  Carbon nanorods, nanowires, nanoplatelets or nanofibres · CPC title

• H01M2004/028

  Positive electrodes · CPC title

• H01M12/06

  with one metallic and one gaseous electrode · CPC title