Squaric acid-based polymers, their manufacturing processes and their uses
AssigneesHydro-Quebec, Murata Manufacturing Co., Ltd.
InventorsJean-Christophe DAIGLE, Antoine LAFLEUR-LAMBERT, Sylviane ROCHON, Yuichiro ASAKAWA, Charlotte MALLET, Karim ZAGHIB
Life of this patent
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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.
Claims20
A process for producing a polymer, the process comprising the steps of:
- (a) reacting monomeric units of Formulae II and III:
- wherein,
- Y is a leaving group, independently in each occurrence, selected from a halogen atom, a hydroxyl group, an amine group and a lower alkoxy group, preferably Y is independently in each occurrence a chlorine atom, bromine atom, iodine atom, amine group, hydroxyl group or lower alkoxy group;
- and
- X is, independently in each occurrence, selected from an oxygen atom, a sulfur atom and an amine group of the formula NRx;
- R1 is an optionally substituted conjugated non-aromatic cyclic group, such as a quinone group, an optionally substituted aromatic or partially aromatic organic group, or combination thereof in a polycyclic group, preferably R1 is a monocyclic or polycyclic aromatic or partially aromatic organic group, preferably 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;
- Rx is a hydrogen atom or an optionally substituted alkyl;
- and
- q is an integer representing the number of XH groups within the monomeric unit of Formula III and is at least 2;
- wherein the polymer is preferably produced by a polycondensation reaction;
- and
- (b) isolating the polymer produced in step (a).
A process for producing a polymer, the process comprising the steps of:
- (a) reacting monomeric units of Formulae II and IV:
- wherein,
- Y is a leaving group is independently in each occurrence selected from a chlorine atom, a bromine atom and an iodine atom, preferably Y is in each occurrence a chlorine atom;
- R1 is an optionally substituted conjugated non-aromatic cyclic group, such as a quinone group, an optionally substituted aromatic or partially aromatic organic group, or combination thereof in a polycyclic group, preferably R1 is a monocyclic or polycyclic aromatic or partially aromatic organic group, preferably 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;
- Z is independently in each occurrence, selected from the group consisting of a chlorine atom, a bromine atom, an iodine atom, a boronic acid, a boronic acid ester and a trialkyltin group, preferably Z is in each occurrence a chlorine atom or a bromine atom;
- r is an integer representing the number of Z within the monomeric unit of Formula IV and is at least 2;
- and
- wherein the monomeric unit of Formula IV is preferably selected from Formulae IV(a) to IV(o):
- (b) isolating the polymer produced in step (a).
An electrode material 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 NRx;
- p is an integer representing the number of X groups in each monomeric unit and is 0 or 1;
- R1 is an optionally substituted conjugated non-aromatic cyclic group, such as a quinone group, an optionally substituted aromatic or partially aromatic organic group, or combination thereof in a polycyclic group, preferably R1 is a monocyclic or polycyclic aromatic or partially aromatic organic group, preferably 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;
- and
- Rx is a hydrogen atom or an optionally substituted alkyl.
An electrolyte composition comprising a salt 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 NRx;
- p is an integer representing the number of X groups in each monomeric unit and is 0 or 1;
- R1 is an optionally substituted conjugated non-aromatic cyclic group, such as a quinone group, an optionally substituted aromatic or partially aromatic organic group, or combination thereof in a polycyclic group, preferably R1 is a monocyclic or polycyclic aromatic or partially aromatic organic group, preferably 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;
- and Rx is a hydrogen atom or an optionally substituted alkyl;
- preferably said electrolyte composition is a solid polymer electrolyte (SPE) composition or a gel electrolyte composition.
An electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein at least one of the positive electrode or electrolyte comprises 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 NRx;
- p is an integer representing the number of X groups in each monomeric unit and is 0 or 1;
- R1 is an optionally substituted conjugated non-aromatic cyclic group, such as a quinone group, an optionally substituted aromatic or partially aromatic organic group, or combination thereof in a polycyclic group, preferably R1 is a monocyclic or polycyclic aromatic or partially aromatic organic group, preferably 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;
- and
- Rx is a hydrogen atom or an optionally substituted alkyl;
- preferably the negative electrode is an alkali metal film and more preferably a metallic lithium film or an alloy thereof.
Dependencies are inferred from the claim text.