IP Library › Granted Patent US 12,215,190
Granted Patent B2
US 12,215,190 · App. 16/982,178 · Granted Feb 4, 2025

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

Inventors: Jean-Christophe Daigle (St-Bruno-de-Montarville, CA); Antoine Lafleur-Lambert (Québec, CA); Sylviane Rochon (Saint-Adelphe, CA); Yuichiro Asakawa (Nagaokakyo, JP); Charlotte Mallet (Montreal, CA); Karim Zaghib (Longueuil, CA)
Assignees: HYDRO-QUÉBEC; MURATA MANUFACTURING CO., LTD.
C08G65/005C08G65/4087G02F1/15165H01B1/124H01M10/0565H10K85/111H10K85/151C08G2261/316C08G2261/3223C08G2261/3342H01M10/0525H01M2300/0082
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Quick Facts
Patent No.
US 12,215,190
App. No.
16/982,178
Granted
Feb 4, 2025
Kind
B2
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.

Claims (20)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2026
From: MURATA MANUFACTURING CO., LTD.
To: HYDRO-QUEBEC
Reel/Frame 075652/0759 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2020
From: DAIGLE, JEAN-CHRISTOPHE; LAFLEUR-LAMBERT, ANTOINE; ROCHON, SYLVIANE; ASAKAWA, YUICHIRO; MALLET, CHARLOTTE; ZAGHIB, KARIM
To: HYDRO-QUÉBEC; MURATA MANUFACTURING CO., LTD.
Reel/Frame 053815/0063 →
Continuity (3)
Provisional Application 62700554 · Jul 19, 2018
Provisional Application 62664611 · Apr 30, 2018
Related Publication 20210032403A1 · Feb 4, 2021
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