Squaric acid-based polymers, their manufacturing processes and their uses

Patent metadata

Field	Value
Publication number	US-12215190-B2
Application number	US-201916982178-A
Country	US
Kind code	B2
Filing date	Apr 30, 2019
Priority date	Apr 30, 2018
Publication date	Feb 4, 2025
Grant date	Feb 4, 2025

Abstract

Squaric acid-based polymers and their use in electrode materials and/or electrolyte compositions, as well as their production processes are described herein. Also described are electrode materials, electrodes, electrolyte compositions, electrochemical cells, electrochemical accumulators, and optoelectronic devices comprising the polymers and their uses.

First claim

The invention claimed is:

1. An element of an electrochemical cell comprising a polymer of Formula I:

wherein,
n and m are integers representing the number of each monomeric units within the polymer, wherein n≥2 and m≥0;
X is, independently in each occurrence, selected from an oxygen atom, a sulfur atom, and an amine group of the formula NR x ;
p is an integer representing the number of X groups in each monomeric unit and is 0 or 1;
R 1 is an optionally substituted conjugated non-aromatic cyclic group, an optionally substituted aromatic or partially aromatic organic group, or a combination thereof in a polycyclic group; and
R x is a hydrogen atom or an optionally substituted alkyl.

2. The element of claim 1 , wherein R 1 is a heterocyclic compound.

3. The element of claim 1 , wherein each substituted R 1 is substituted with one or more substituent independently in each occurrence, selected from an alkyl group, an alkoxy group, a nitrile group, a hydroxyl group, and a halogen atom, or with a protecting group when attached to a heteroatom.

4. The element of claim 1 , wherein R 1 is selected from the group consisting of benzene, naphthalene, anthracene, benzoquinone, naphthoquinone, and anthraquinone.

5. The element of claim 1 , wherein p is 1, X is an amine group (NH) in each occurrence, and R 1 is selected from the group consisting of para-phenylene and anthraquinone.

6. The element of claim 1 , wherein m is 0 and the polymer of Formula I is a homopolymer selected from:

7. The element of claim 1 , wherein the polymer is selected from:

wherein Ar is an aryl divalent group.

8. The element of claim 1 , wherein R 1 is a monocyclic or polycyclic aromatic or partially aromatic organic group.

9. The element of claim 8 , wherein the monocyclic or polycyclic aromatic or partially aromatic organic group is derived from one or a plurality fused benzene rings or from one or a plurality of 5 or 6-membered fused rings or combinations thereof.

10. The element of claim 2 , wherein each heterocyclic ring comprises from 1 to 3 heteroatoms selected from a N, S, and O.

11. The element of claim 10 , wherein the heteroatom is N or S.

12. The element of claim 1 , wherein p is 1, X is an oxygen atom in each occurrence, and R 1 is selected from the group consisting of benzene, naphthoquinone, cyclohex-5-ene-1,2,3,4-tetrone, cyclopentenetrione, and 1,4-benzoquinone.

13. The element of claim 1 , wherein p is 0 and R 1 is selected from the group consisting of benzene, phenylene, pyridine, thiophene, thienopyrroledione, benzothiophene, benzothiadiazole, 3,4-ethylenedioxythiophene, carbazole, dithiopheneanthanthrone, dithiophenediketopyrrolopyrrole, isoindigo, and indigo.

Assignees

• Hydro Quebec
• Murata Manufacturing Co

Inventors

• Daigle Jean-Christophe
• Lafleur-Lambert Antoine
• Rochon Sylviane
• Asakawa Yuichiro
• Mallet Charlotte
• Zaghib Karim

Classifications

• H10K85/151

  Copolymers · CPC title

• H10K85/111

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

• H01M2300/0082

  Organic polymers · CPC title

• H01M10/0565

  Polymeric materials, e.g. gel-type or solid-type · CPC title

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title