WO2019188358A1 - Électrolyte pour batteries secondaires au fluorure-ion, et batterie secondaire au fluorure-ion utilisant ledit électrolyte - Google Patents

Électrolyte pour batteries secondaires au fluorure-ion, et batterie secondaire au fluorure-ion utilisant ledit électrolyte Download PDF

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Publication number
WO2019188358A1
WO2019188358A1 PCT/JP2019/010630 JP2019010630W WO2019188358A1 WO 2019188358 A1 WO2019188358 A1 WO 2019188358A1 JP 2019010630 W JP2019010630 W JP 2019010630W WO 2019188358 A1 WO2019188358 A1 WO 2019188358A1
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Prior art keywords
ion secondary
electrolyte
fluoride ion
secondary battery
cation
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PCT/JP2019/010630
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English (en)
Japanese (ja)
Inventor
森田　善幸
野平　俊之
山本　貴之
一彦 松本
理加 萩原
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本田技研工業株式会社
国立大学法人京都大学
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Application filed by 本田技研工業株式会社, 国立大学法人京都大学 filed Critical 本田技研工業株式会社
Priority to CN201980023194.8A priority Critical patent/CN112042037A/zh
Priority to DE112019001638.5T priority patent/DE112019001638T5/de
Priority to JP2020509907A priority patent/JP6959436B2/ja
Publication of WO2019188358A1 publication Critical patent/WO2019188358A1/fr

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0045—Room temperature molten salts comprising at least one organic ion
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
    • H01M4/582—Halogenides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to an electrolyte for a fluoride ion secondary battery and a fluoride ion secondary battery using the electrolyte.
  • the fluoride ion secondary battery is a secondary battery using fluoride ions (F ⁇ ) as carriers, and is known to have high theoretical energy. And about the battery characteristic, there exists an expectation exceeding a lithium ion secondary battery.
  • Non-Patent Documents 8 and 9 There are also reports of fluoride ion conductive electrolytes operating near room temperature (see Non-Patent Documents 8 and 9).
  • Non-Patent Document 8 reports NH 4 FHF-PEG polymer
  • Non-Patent Document 9 reports MPPF / TMPA-TFSA ionic liquid.
  • the ionic conductivity of each electrolyte is not always sufficient, and the development of a new electrolyte has been desired.
  • the present invention has been made in view of the above-described background art, and its purpose is for a fluoride ion secondary battery capable of realizing a fluoride ion secondary battery that can operate sufficiently even in a low temperature environment.
  • An electrolyte and a fluoride ion secondary battery using the electrolyte are provided.
  • an ionic liquid containing a fluorohydrogen anion exhibits high ionic conductivity. If a fluorohydrogen anion ([(FH) n F] ⁇ ) is used as an electrolyte of a fluoride ion secondary battery, a fluoride ion secondary battery having high fluoride ion conductivity can be obtained. As a result, the present invention has been completed.
  • the present invention is an electrolyte for a fluoride ion secondary battery containing a fluorohydrogen anion or a salt derived from the fluoro hydrogen anion.
  • the electrolyte for a fluoride ion secondary battery may be an ionic liquid.
  • the ionic liquid may contain a cation.
  • the electrolyte for fluoride ion secondary battery may be a plastic ion crystal.
  • the plastic ionic crystal may be a salt of a fluorohydrogen anion and a cation.
  • the cation may be a cyclic cation.
  • the cyclic cation may be a cation derived from an imidazolium compound.
  • the cation derived from the imidazolium compound may be 1-ethyl-3-methylimidazolium.
  • the cyclic cation may be a cation derived from a pyrrolidinium compound.
  • the cation derived from the pyrrolidinium compound may be dimethylpyrrolidinium or N-ethyl-N-propylpyrrolidinium.
  • Another embodiment of the present invention is a fluoride ion secondary battery comprising the above-described electrolyte for a fluoride ion secondary battery, a positive electrode, and a negative electrode.
  • the fluoride ion conductivity in the fluoride ion secondary battery can be increased.
  • the temperature characteristics of the charge / discharge capacity are improved, and a fluoride ion secondary battery that can operate sufficiently even in an environment having a low temperature can be realized.
  • EMPyr (FH) n F It is a state diagram of EMPyr (FH) n F. It is a state diagram of DMPyr (FH) n F. It is the schematic of the tripolar type evaluation cell used in the Example.
  • 2 is a charge / discharge curve of a fluoride ion secondary battery using the electrolyte of Example 1.
  • FIG. 2 is a charge / discharge curve of a fluoride ion secondary battery using the electrolyte of Example 2.
  • FIG. 4 is a charge / discharge curve of a fluoride ion secondary battery using the electrolyte of Example 3. It is a charging / discharging curve of the fluoride ion secondary battery using the electrolyte of Example 4.
  • the electrolyte for fluoride ion secondary batteries of the present invention contains a fluorohydrogen anion or a salt derived from the fluoro hydrogen anion.
  • the fluorohydrogen anion used as the constituent material of the electrolyte for the fluoride ion secondary battery of the present invention is represented by the structural formula [(FH) n F] ⁇ . n is not necessarily an integer.
  • the fluorohydrogen anion constituting the electrolyte for a fluoride ion secondary battery of the present invention may be a single type or a mixture of two or more types.
  • the fluorohydrogen anion constituting the electrolyte for a fluoride ion secondary battery of the present invention is not particularly limited, but n is 1 to 3 represented by the following chemical formulas (1) to (3). Those having a structure which is an integer are preferred.
  • the fluorohydrogen anions represented by the chemical formulas (1) to (3) can be handled safely because the dissociation pressure of HF is sufficiently low.
  • the cation used in combination with the fluorohydrogen anion ([(FH) n F] ⁇ ) is not particularly limited. In order to express the characteristics of the secondary battery, it is possible to select appropriately.
  • the structure of the cation that can constitute the electrolyte for a fluoride ion secondary battery of the present invention is not particularly limited, whether it is a chain structure or a cyclic structure.
  • Examples of the chain cation include a cation represented by the following chemical formula (4).
  • R 1 to R 4 are each independently hydrogen, an alkyl group, a fluoroalkyl group, or an alkoxyalkyl group.
  • R 1 to R 4 are an alkyl group, a fluoroalkyl group or an alkoxyalkyl group, the carbon number thereof is, for example, 10 or less, preferably 6 or less, more preferably 4 or less, and more preferably 2 or less. More preferably.
  • R 1 to R 4 are preferably hydrogen or an alkyl group, a fluoroalkyl group or an alkoxyalkyl group having 4 or less carbon atoms, especially 2 or less carbon atoms.
  • R 1 and R 2 , or R 3 and R 4 may be connected to form a cyclic structure.
  • R 1 to R 4 are each independently hydrogen, an alkyl group, a fluoroalkyl group, or an alkoxyalkyl group.
  • R 1 to R 4 are an alkyl group, a fluoroalkyl group or an alkoxyalkyl group, the carbon number thereof is, for example, 10 or less, preferably 6 or less, more preferably 4 or less, and more preferably 2 or less. More preferably.
  • R 1 to R 4 are preferably hydrogen or an alkyl group, a fluoroalkyl group or an alkoxyalkyl group having 4 or less carbon atoms, especially 2 or less carbon atoms.
  • R 1 and R 2 , or R 3 and R 4 may be connected to form a cyclic structure.
  • tetraethylammonium (N2222) or 5-azoniaspiro [4.4] nonane (AS [4.4]) is preferable.
  • Tetraethylammonium (N2222) or 5-azoniaspiro [4.4] nonane (AS [4.4]) makes it possible to form a plastic ionic crystal phase having high ion conductivity near room temperature.
  • R 1 to R 3 are each independently hydrogen, an alkyl group, a fluoroalkyl group, or an alkoxyalkyl group.
  • R 1 to R 3 are an alkyl group, a fluoroalkyl group or an alkoxyalkyl group, the carbon number thereof is, for example, 10 or less, preferably 6 or less, more preferably 4 or less, and more preferably 2 or less. More preferably.
  • R 1 to R 3 are preferably hydrogen or an alkyl group, a fluoroalkyl group or an alkoxyalkyl group having 4 or less carbon atoms, especially 2 or less carbon atoms. Note that part or all of hydrogen in each structure may be substituted with fluorine.
  • R 1 and R 2 , or R 3 and R 4 may be connected to form a cyclic structure.
  • Tetraethylphosphonium (P2222) is preferable. Tetraethylphosphonium (P2222) can form a plastic ionic crystal phase with high ion conductivity near room temperature.
  • examples of the cyclic cation include a cation represented by the following chemical formula (7).
  • R 1 or R 2 is each independently hydrogen, an alkyl group, a fluoroalkyl group or an alkoxyalkyl group
  • R 3 is a functional group for forming a cyclic structure, and at least Contains carbon.
  • R 1 or R 2 is an alkyl group, a fluoroalkyl group or an alkoxyalkyl group
  • the carbon number thereof is, for example, 10 or less, preferably 6 or less, more preferably 4 or less, and more preferably 2 or less. More preferably.
  • R 1 or R 2 is preferably hydrogen or an alkyl group, a fluoroalkyl group or an alkoxyalkyl group having 4 or less carbon atoms, especially 2 or less carbon atoms.
  • the cyclic structure composed of N and R 3 may be a 5-membered ring structure, a 6-membered ring structure, or a 7-membered ring structure.
  • the cyclic structure composed of N and R 3 may be aromatic or non-aromatic.
  • the cyclic structure composed of N and R 3 is preferably, for example, a pyrrolidine structure, a pyrrole structure, a piperidine structure, or a pyridine structure.
  • R 1 and R 2 may be connected to form a cyclic structure.
  • the cation that can constitute the electrolyte for a fluoride ion secondary battery of the present invention is preferably a cyclic cation.
  • the cation is regularly arranged at the interface of the active material, so that a structure in which fluoride ions are easily diffused can be formed.
  • the reaction rate of at least one of the fluorination reaction or the defluorination reaction of the active material can be improved.
  • the cation capable of constituting the electrolyte for a fluoride ion secondary battery of the present invention is a cyclic cation, it is preferably a heterocyclic structure containing a cation central element (N element, P element).
  • the cyclic structure may be aromatic or non-aromatic.
  • the cation that can constitute the electrolyte for a fluoride ion secondary battery of the present invention is preferably a cation derived from an imidazolium-based compound. If it is a cation derived from an imidazolium-based compound, it becomes possible to form an ionic liquid phase having high ionic conductivity near room temperature.
  • 1-ethyl-3-methylimidazolium (EMIm) is more preferable.
  • 1-Ethyl-3-methylimidazolium (EMIm) has a low melting point and high ionic conductivity.
  • the cations that can constitute the electrolyte for fluoride ion secondary batteries of the present invention are preferably cations derived from pyrrolidinium compounds.
  • a cation derived from a pyrrolidinium compound has a low melting point and high ionic conductivity.
  • dimethylpyrrolidinium (DMPyr) or N-ethyl-N-propylpyrrolidinium (EMPyr) is more preferable.
  • Dimethylpyrrolidinium (DMPyr) or N-ethyl-N-propylpyrrolidinium (EMPyr) has a low melting point and high ionic conductivity.
  • the form of the electrolyte for a fluoride ion secondary battery of the present invention is not particularly limited, and may be any of liquid, gel, and solid.
  • the form of the electrolyte for a fluoride ion secondary battery of the present invention includes the kind of cation used in combination with the fluorohydrogen anion ([(FH) n F] ⁇ ), the fluorohydrogen anion ([(FH) n F] ⁇ ), depending on the number of n. Therefore, a preferable form as an electrolyte of a fluoride ion secondary battery can be appropriately selected.
  • the form of the electrolyte for the fluoride ion secondary battery is preferably an ionic liquid or a plastic ionic crystal.
  • FIG. 1 shows a phase diagram of EMPyr (FH) n F, which is an example of an electrolyte for a fluoride ion secondary battery of the present invention.
  • EMPyr (FH) 2.0 F in which n is 2.0 has a melting point of 30 ° C., and becomes a plastic ionic crystal (Ionic Plastic Crystal (IPC)) near room temperature (25 ° C.).
  • the conductivity of EMPyr (FH) 2.0 F at 25 ° C. is 19.0 mScm ⁇ 1 .
  • FIG. 2 shows a state diagram of DMPyr (FH) n F.
  • the conductivity of DMPyr (FH) 2.0 F at 25 ° C. is 10.3 mScm ⁇ 1
  • the conductivity at 40 ° C. is 14.4 mScm ⁇ 1 .
  • the battery for fluoride ion secondary batteries of the present invention comprises the electrolyte for fluoride ion secondary batteries of the present invention, a positive electrode, and a negative electrode. If the electrolyte for fluoride ion secondary batteries of this invention uses the electrolyte for fluoride ion secondary batteries of this invention, another structure will not be specifically limited.
  • a positive electrode material that provides a sufficiently high standard electrode potential with respect to the standard electrode potential of the negative electrode for a fluoride ion secondary battery is selected, and between these, the positive electrode material for the fluoride ion secondary battery of the present invention is selected.
  • the electrolyte for a fluoride ion secondary battery of the present invention can be obtained by reacting the target cation and a salt composed of halide ions with hydrogen fluoride.
  • the reaction method is not particularly limited. Taniki, K .; Matsumoto, R.A. Hagiwara, K .; Hachiya, T .; Morinaga, T .; Sato, J .; Phys. Chem. B, 117 (2013) 955. It can be manufactured by the method described in 1.
  • the electrolyte 1 EMIm (FH) 2.3 The melting point of F is -65 °C
  • EMPyr (FH) 2.3 F melting point of the electrolyte 2 is -37 ° C., thus, the electrolyte 1 and electrolytes in 25 ° C. 2
  • the form of was an ionic liquid.
  • DMPyr (FH) 2.0 F melting point of the electrolyte 4 is 52 ° C., the electrolyte 3 and the electrolyte 4 at 25 ° C. embodiment It was a plastic ionic crystal.
  • a fluoride ion secondary battery was produced by the following method using the following materials.
  • Electrodes As the electrolyte, the electrolytes 1 and 2 that are ionic liquids obtained above and the electrolytes 3 and 4 that are plastic ionic crystals were used.
  • a CuF 2 mixed electrode As the positive electrode, a CuF 2 mixed electrode was used. CuF 2 particles (made by Alfa Aesar), acetylene black (made by Strem chemicals) for providing an electron conduction path, and PTFE (made by Aldrich) for maintaining adhesion between the particles are respectively in a mass ratio of 85: 10: 5. Were weighed and thoroughly mixed, and then formed into a film shape to obtain a positive electrode mixture film.
  • a CuF 2 / Cu mixed electrode was used as the negative electrode. Similar to the positive electrode mixture film, CuF 2 particles (made by Alfa Aesar), Cu particles (made by Aldrich), acetylene black (made by Strem chemicals), and PTFE (made by Aldrich) each have a mass of 50: 35: 10: 5. The mixture was weighed in a ratio and sufficiently mixed, and then formed into a film shape to obtain a negative electrode mixture film.
  • Electrolyte 1 that is an ionic liquid for the purpose of providing an ion conduction path by pressing a positive electrode mixture film (2.5 mg) and a negative electrode mixture film (12.5 mg) on a platinum mesh at a pressure of 20 MPa for 10 minutes.
  • Electrolytes 3 to 4 which are ⁇ 2 or plastic ionic crystals were impregnated in the voids in the mixture film to obtain a positive electrode and a negative electrode.
  • two PTFE membranes made by Merck, thickness: 65 ⁇ m
  • electrolytes 1 and 2 that are ionic liquids or electrolytes 3 and 4 that were plastic ionic crystals, and this was used as a separator.
  • a copper wire manufactured by Niraco, diameter 1 mm
  • the copper wire was insulated with a Teflon (registered trademark) heat-shrinkable tube in advance, and only both ends were exposed for electrical conduction.
  • the obtained positive electrode, separator, and negative electrode are stacked in a dedicated three-electrode evaluation cell (made by EC Frontier) shown in FIG. 3, and the pseudo reference electrode is inserted from the top of the cell so that one end of the pseudo-reference electrode contacts only the separator.
  • a fluoride ion secondary battery was obtained.
  • FIG. 7 shows a charge / discharge curve of a fluoride ion secondary battery using DMPyr (FH) 2.0 F of Example 4.
  • FIG. 6B shows the relationship between the number of cycles and the capacity of the fluoride ion secondary battery using EMPyr (FH) 2.0 F of Example 3.

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Abstract

L'invention concerne : un électrolyte pour batteries secondaires au fluorure-ion, qui permet la fabrication d'une batterie secondaire au fluorure-ion qui peut fonctionner de manière satisfaisante même dans un environnement à basse température ; et une batterie secondaire au fluorure-ion utilisant l'électrolyte. Un électrolyte pour batteries secondaires au fluorure-ion, qui contient un anion fluorohydrogéné ([(FH)nF]-) ou un sel dérivé d'un anion fluorohydrogéné.
PCT/JP2019/010630 2018-03-29 2019-03-14 Électrolyte pour batteries secondaires au fluorure-ion, et batterie secondaire au fluorure-ion utilisant ledit électrolyte WO2019188358A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201980023194.8A CN112042037A (zh) 2018-03-29 2019-03-14 氟化物离子二次电池用电解质及使用了该电解质的氟化物离子二次电池
DE112019001638.5T DE112019001638T5 (de) 2018-03-29 2019-03-14 Elektrolyt für fluoridionensekundärbatterien und den elektrolyten verwendende fluoridionensekundärbatterie
JP2020509907A JP6959436B2 (ja) 2018-03-29 2019-03-14 フッ化物イオン二次電池用電解質、および当該電解質を用いたフッ化物イオン二次電池

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JP2018-065610 2018-03-29
JP2018065610 2018-03-29

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210075061A1 (en) * 2018-04-16 2021-03-11 Industry-University Cooperation Foundation Hanyang University Erica Campus Solid Electrolyte, Intermediate of Solid Electrolyte, Secondary Battery Comprising the Same, and Method of Fabricating the Same
JP2021521597A (ja) * 2018-04-16 2021-08-26 漢陽大学校エリカ産学協力団Ｉｎｄｕｓｔｒｙ−Ｕｎｉｖｅｒｓｉｔｙ Ｃｏｏｐｅｒａｔｉｏｎ Ｆｏｕｎｄａｔｉｏｎ Ｈａｎｙａｎｇ Ｕｎｉｖｅｒｓｉｔｙ Ｅｒｉｃａ Ｃａｍｐｕｓ 固体電解質、その製造方法、及びこれを含む自家発電二次電池
WO2022050050A1 (fr) * 2020-09-04 2022-03-10 国立大学法人京都大学 Batterie secondaire à ions fluorure

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JP2010111597A (ja) * 2008-11-04 2010-05-20 Otsuka Chem Co Ltd 第４級アンモニウム塩
JP2016051646A (ja) * 2014-09-01 2016-04-11 積水化学工業株式会社 ハロゲン二次電池
JP2016164857A (ja) * 2015-03-06 2016-09-08 トヨタ自動車株式会社 フッ化物イオン電池用電解液およびフッ化物イオン電池
JP2017088427A (ja) * 2015-11-04 2017-05-25 本田技研工業株式会社 結晶体の製造方法、結晶体及びフッ化物イオン２次電池用電解質
JP2017117592A (ja) * 2015-12-22 2017-06-29 国立大学法人京都大学 二次電池用電解液

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210075061A1 (en) * 2018-04-16 2021-03-11 Industry-University Cooperation Foundation Hanyang University Erica Campus Solid Electrolyte, Intermediate of Solid Electrolyte, Secondary Battery Comprising the Same, and Method of Fabricating the Same
JP2021521597A (ja) * 2018-04-16 2021-08-26 漢陽大学校エリカ産学協力団Ｉｎｄｕｓｔｒｙ−Ｕｎｉｖｅｒｓｉｔｙ Ｃｏｏｐｅｒａｔｉｏｎ Ｆｏｕｎｄａｔｉｏｎ Ｈａｎｙａｎｇ Ｕｎｉｖｅｒｓｉｔｙ Ｅｒｉｃａ Ｃａｍｐｕｓ 固体電解質、その製造方法、及びこれを含む自家発電二次電池
JP7141142B2 (ja) 2018-04-16 2022-09-22 漢陽大学校エリカ産学協力団 固体電解質、その製造方法、及びこれを含む自家発電二次電池
WO2022050050A1 (fr) * 2020-09-04 2022-03-10 国立大学法人京都大学 Batterie secondaire à ions fluorure

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