EP4348733A1 - Beschichtungsmaterialien auf basis ungesättigter aliphatischer kohlenwasserstoffe und verwendungen davon in elektrochemischen anwendungen - Google Patents

Beschichtungsmaterialien auf basis ungesättigter aliphatischer kohlenwasserstoffe und verwendungen davon in elektrochemischen anwendungen

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Publication number
EP4348733A1
EP4348733A1 EP22814657.7A EP22814657A EP4348733A1 EP 4348733 A1 EP4348733 A1 EP 4348733A1 EP 22814657 A EP22814657 A EP 22814657A EP 4348733 A1 EP4348733 A1 EP 4348733A1
Authority
EP
European Patent Office
Prior art keywords
material according
electrode material
electrode
coating
electrolyte
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22814657.7A
Other languages
English (en)
French (fr)
Inventor
Benoît FLEUTOT
Emmanuelle Garitte
Charlotte MALLET
Nicolas DELAPORTE
Marc-André GIRARD
Steve DUCHESNE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hydro Quebec
Original Assignee
Hydro Quebec
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hydro Quebec filed Critical Hydro Quebec
Publication of EP4348733A1 publication Critical patent/EP4348733A1/de
Pending legal-status Critical Current

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Classifications

    • 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
    • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • 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
    • H01M10/052—Li-accumulators
    • 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
    • H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
    • 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
    • H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
    • 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
    • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • H01M4/624—Electric conductive fillers
    • H01M4/625—Carbon or graphite
    • 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
    • H01M4/362—Composites
    • H01M4/366—Composites as layered products

Definitions

  • the present application relates to the field of coatings and their use in electrochemical applications. More particularly, the present application relates to coatings for particles of ion-conductive inorganic material, of electrochemically active material, of electronic conductor, to their manufacturing processes and to their uses in electrochemical cells, in particular in so-called all-solid batteries . STATE OF THE ART
  • All-solid-state electrochemical systems are substantially safer, lighter, more flexible and more efficient than their counterparts based on the use of liquid electrolytes.
  • the field of application of solid electrolytes is still limited.
  • solid polymer electrolytes present problems related to their limited electrochemical stability, their low transport number and their relatively low ionic conductivity at room temperature.
  • Ceramic-based solid electrolytes exhibit a wide window of electrochemical stability and substantially higher ionic conductivity at room temperature. However, they are associated with problems related to their interfacial stability as well as their stability to ambient air and humidity.
  • dispersion media examples are described in the European patent published under number EP 3 467 845, these being present in the composition of the solid electrolyte.
  • the manufacture of ceramic-based solid electrolytes is associated with cracking problems as a result of the dry compression process.
  • One strategy employed to solve this problem involves the encapsulation of the ceramic-based solid electrolyte particles by a substantially flexible (or elastic) polymer.
  • a substantially flexible (or elastic) polymer for example, the Korean patent published under the number KR 10-2003300 describes a polymeric coating layer comprising a polymer based on acrylic, fluorine, diene, silicone, or cellulose applied to the surface of particles of crystalline sulfide electrolyte.
  • the polymeric coating layer also allows the aggregation of the electrolyte particles without lowering their ionic conductivity and makes it possible to absorb volume variations during cycling.
  • the present technology relates to a coating material comprising at least one branched or linear unsaturated aliphatic hydrocarbon having from 10 to 50 of carbon and having at least one carbon-carbon double or triple bond for use in an electrochemical cell.
  • the boiling point of the unsaturated aliphatic hydrocarbon is greater than 150°C.
  • the boiling temperature of the unsaturated aliphatic hydrocarbon is in the range of from about 150°C to about 675°C, or from about 155°C to about 670°C, or from about 160°C to about 665°C, or ranging from about 165°C to about 660°C, or ranging from about 170°C to about 655°C, upper and lower limits included.
  • the unsaturated aliphatic hydrocarbon is selected from the group consisting of decene, dodecene, undecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, 1,9-decadiene, docosene, hexacosene, eicosene, tetracosene, squalene, farnesene, b-carotene, pinenes, dicyclopentadiene, camphene, a -phellandrene, b-phellandrene, terpinenes, b-myrcene, limonene, 2-carene, sabinene, a-cedrene, copaene, b-cedrene, decyne, dodecyne, octa
  • the unsaturated aliphatic hydrocarbon comprises squalene.
  • the unsaturated aliphatic hydrocarbon comprises farnesene.
  • the unsaturated aliphatic hydrocarbon comprises squalene and farnesene.
  • the coating material is a mixture comprising the unsaturated aliphatic hydrocarbon and an additional component.
  • the additional component is an alkane or a mixture comprising an alkane and a polar solvent.
  • the present technology relates to coated particles for use in an electrochemical cell, said coated particle comprising: a core comprising an electrochemically active material, an electronically conductive material or an ionically conductive inorganic material; and a potting material as defined herein, the potting material being disposed on the surface of the core.
  • the present technology relates to a process for manufacturing coated particles as defined here, the process comprising at least one step of coating at least part of the surface of the core with the coating material.
  • the method further comprises a step of grinding the electrochemically active material, the electronically conductive material or the ionically conductive inorganic material of the core of the coated particle.
  • the present technology relates to an electrode material comprising: coated particles as herein defined, wherein the core of the coated particle comprises an electrochemically active material; and/or an electrochemically active material and coated particles as defined herein.
  • the core of the coated particle comprises the electrochemically active material.
  • the electrochemically active material is chosen from a metal oxide, a metal sulphide, a metal oxysulphide, a metal phosphate, a metal fluorophosphate, a metal oxyfluorophosphate, a metal sulphate, a metal halide , a metal fluoride, sulfur, selenium, and a combination of two or more thereof.
  • the metal of the electrochemically active material is chosen from titanium (Ti), iron (Fe), manganese (Mn), vanadium (V), nickel (Ni), cobalt (Co), aluminum (Al), chromium (Cr), copper (Cu), zirconium (Zr), niobium (Nb), and a combination of at least two of these.
  • the electrochemically active material further comprises an alkali or alkaline-earth metal chosen from lithium (Li), sodium (Na), potassium (K) and magnesium (Mg).
  • the electrochemically active material is chosen from a non-alkaline or non-alkaline-earth metal, an intermetallic compound, a metal oxide, a metal nitride, a metal phosphide, a metal phosphate, a halide of metal, a metal fluoride, a metal sulphide, a metal oxysulphide, a carbon, silicon (Si), a silicon-carbon composite (Si-C), a silicon oxide (SiO x ), a composite oxide silicon-carbon (SiO x -C), tin (Sn), tin-carbon composite (Sn-C), tin oxide (SnO x ), tin oxide-carbon composite (SnO x -C), and a combination of two or more of these.
  • a non-alkaline or non-alkaline-earth metal an intermetallic compound, a metal oxide, a metal nitride, a metal phosphide, a
  • the electrode material further comprises at least one electronically conductive material.
  • the core of the coated particle comprises the electronic conductive material.
  • the electronic conductive material is selected from the group consisting of carbon black, acetylene black, graphite, graphene, carbon fibers, carbon nanofibers, carbon nanotubes, and a combination at least two of these.
  • the electrode material further comprises at least one additive.
  • the core of the coated particle comprises the additive.
  • the additive is chosen from inorganic ionic conductive materials, inorganic materials, glasses, glass-ceramics, ceramics, nano-ceramics, salts, and a combination of at least two of these.
  • the additive comprises ceramic, glass or glass-ceramic particles based on fluoride, phosphide, sulphide, oxysulphide or oxide.
  • the additive is chosen from compounds of the LISICON, thio-LISICON, argyrodite, garnet, NASICON, perovskite type, oxides, sulphides, oxysulphides, phosphides, fluorides, in crystalline form and/or amorphous, and a combination of two or more thereof.
  • the additive is chosen from inorganic compounds of formulas MLZO (for example, M 7 La 3 Zr 2 0i 2 , M (7 - a) La3Zr2AlbOi2 , M(7- a) La3Zr2GabOi2 , M(7- a) La3Zr(2-b)TabOi2, and M(7- a) La3Zr(2-b>NbbOi2); MLTaO (for example, M7La3Ta20i2, M 5 La3Ta20i2, and M6La3Ta1.5Y0.5O12); MLSnO (for example, M7La3Sn20i2); MAGP (e.g.
  • MATP e.g. Mi +a Al a Ge2- a (P04)3,; MATP (e.g. Mi +a Al a TÎ2- a (P04)3,); MLTiO (e.g. M3aLa(2 /3-a>Ti03); MZP (for example, M a Zrb(P04) c ); MCZP (for example, M a CabZr c (P04)d); MGPS (for example, M a GebP c Sd such as MioGeP2Si2 ); MGPSO (for example, M a Ge b P c S d O e ); MSiPS (for example, M a Si b P c S d such as M 10 S1P 2 S 12 ); MSiPSO (for example, M a Si b P c S d O e ); MSnPS (for example, M a Sn b P c S d such as MioSnP 2 Si 2
  • M a P b S c O d MZPS (e.g. M a Zn b P c S d ); MZPSO ( by example, M a Zn b P c S d O e ); xM 2S -yP 2S 5 ; xM 2S -yP 2S 5 -zMX; xM2S - yP2S5 -zP205 ; XM 2S -yP 2S 5 -zP 20 5 -wMX; xM 2S -yM 20 -zP 2S 5 ; xM 2S -yM 20 -zP 2S 5 -wMX; xM2S - yM20 - zP2S5 - WP2O5 ; xM 2S -yM 20 -zP 2S 5 -wP 20 5 -vMX; xM 2 S-ySiS 2 ; MPSX (
  • M is an alkali metal ion, an alkaline earth metal ion or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
  • X is selected from F, Cl, Br, I or a combination of at least two of these; a, b, c, d, e and f are numbers other than zero and are independently in each formula selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are independently in each formula selected to yield a stable compound.
  • the additive is chosen from inorganic compounds of argyrodite type of formula LÎ 6 PS 5 X, in which X is Cl, Br, I or a combination of at least two of these.
  • the additive is LI 6 PS 5 CI.
  • the present technology relates to an electrode comprising the electrode material as defined herein on a current collector.
  • the present technology relates to a self-supporting electrode comprising the electrode material as defined herein.
  • said electrode is a positive electrode.
  • the present technology relates to an electrolyte comprising coated particles as herein defined, wherein the core of the coated particle comprises an ionically conductive inorganic material.
  • the ion-conductive inorganic material is chosen from glasses, glass-ceramics, ceramics, nano-ceramics and a combination of at least two of these.
  • the ion-conductive inorganic material comprises a ceramic, a glass or a glass-ceramic based on fluoride, phosphide, sulphide, oxysulphide or oxide.
  • the ion-conductive inorganic material is chosen from compounds of LISICON, thio-LISICON, argyrodites, garnets, NASICON, perovskites, oxides, sulphides, oxysulphides, phosphides, fluorides, of crystalline form and /or amorphous, and a combination of at least two of these.
  • the ionically conductive inorganic material is chosen from inorganic compounds of formulas MLZO (for example, M (7 - a) La3Zr2AlbOi2, M(7- a) La3Zr2GabOi2, M(7- a) La3Zr(2-b)TabOi2, and M(7- a >La3Zr(2-b)NbbOi2); MLTaO (e.g., M7La31a20i2, M 5 La3Ta20i2, and M6La3Ta1.5Y0.5O12); MLSnO (eg, M7La3Sn20i2); MAGP (e.g.
  • MATP e.g. Mi +a Al a Ge2- a (PO4)3); MATP (e.g. Mi +a Al a TI2- a (PO4)3,); MLTiO (e.g., M3aLa(2/3-a)TiO3); MZP (e.g., M a Zrb(PO4) c ); MCZP (e.g., M a CabZr c (PO4)d); MGPS (e.g., M a GebP c Sd such as MioGeP2Si2); MGPSO (e.g., M a Ge b P c S d O e ); MSiPS (for example, M a Si b P c S d such as M 10 S1P 2 S 12 ); MSiPSO (e.g., M a Si b P c S d O e ); MSnPS (e.g., M a Sn b P c S d such as Mi
  • M a SnbPcSdO e MPS (for example, M a PbS c such as M 7 P 3 S 11 ); MPSO (e.g., M a P b S c O d ); MZPS (e.g., M a Zn b P c S d ); MZPSO (e.g., M a Zn b P c S d O e ); xM 2S -yP 2S 5 ; xM 2S -yP 2S 5 -zMX; xM2S - yP2S5 -zP205 ; XM 2S -yP 2S 5 -zP 20 5 -wMX; xM 2S -yM 20 -zP 2S 5 ; xM 2S -yM 20 -zP 2S 5 -wMX; xM2S -yM 20 -zP 2S 5 ; xM 2S
  • M is an alkali metal ion, an alkaline earth metal ion or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
  • the inorganic ion-conductive material is chosen from inorganic compounds of the argyrodite type of formula LÎ 6 PS 5 X, in which X is Cl, Br, I or a combination of at least two of these.
  • the ionically conductive inorganic material is LI 6 PS 5 CI.
  • the present technology relates to a coating material for a current collector comprising coated particles as herein defined, wherein the core of the coated particle comprises an electronically conductive material.
  • the electronic conductive material is carbon.
  • the present technology relates to a current collector comprising a coating material as defined here, placed on a metal foil.
  • the present technology relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which at least one of the positive electrode or the negative electrode is as defined herein or comprises an electrode material as defined herein.
  • the present technology relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which the electrolyte is as defined herein.
  • the present technology relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which at least one of the positive electrode and the negative electrode is on a current collector such as herein defined or comprising a coating material as herein defined.
  • the present technology relates to an electrochemical accumulator comprising at least one electrochemical cell as defined here.
  • the electrochemical accumulator is a battery chosen from among a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a magnesium battery, a magnesium-ion battery.
  • the electrochemical accumulator is a so-called all-solid battery.
  • Figure 1 shows images obtained by scanning electron microscopy (SEM) in (A) of LÎ 6 PS 5 CI particles before the grinding and coating step, and in (B) of LiePSsCI particles coated with a mixture of decane and squalene, as described in Example 3(a).
  • SEM scanning electron microscopy
  • Figure 2 presents results of thermogravimetric analyzes for squalene ( ⁇ ; curve 1) and for particles of Ü 6 PS 5 CI coated with a mixture of decane and squalene (o; curve 2), as described in Example 3(b).
  • Figure 3 presents respectively in (A) and (B) nuclear magnetic resonance spectra of the proton (NMR 1 H) and of carbon (NMR 13 C) obtained for particles of
  • Figure 4 presents proton nuclear magnetic resonance spectra ( 1 H NMR) obtained for pure farnesene as well as for Ü 6 PS 5 CI particles coated with a mixture of decane and farnesene, as described in Example 3(c).
  • Figure 5 presents proton nuclear magnetic resonance (NMR) spectra
  • Figure 6 shows in (A) and (B) images obtained by SEM and mapping images of the Ni and S elements by energy dispersive X-ray spectroscopy (EDS) obtained respectively for Films 1 and 2, such as as described in Example 4(b).
  • EDS energy dispersive X-ray spectroscopy
  • Figure 7 shows in (A) and (B) images obtained by backscattered electron SEM and enlargements of these images respectively for Films 3 and 4, as described in Example 4(b).
  • Figure 8 shows in (A) a graph of discharge capacity (mAh/g) and coulombic efficiency (%) as a function of the number of cycles, and in (B) a graph of the average potential in charge and in discharge (V) as a function of the number of cycles for Cell 1 (A) and for Cell 2 ( ⁇ ), as described in Example 5(b).
  • Figure 9 shows in (A) a graph of the discharge capacity and the coulombic efficiency as a function of the number of cycles, and in (B) a graph of the average potential in charge and in discharge (V) as a function of the number of cycles for Cell 2 ( ⁇ ), Cell 3 (A), Cell 4 (T) and Cell 5 ( ⁇ ), as described in Example 5(b).
  • Figure 10 shows a graph of discharge capacity and coulombic efficiency as a function of cycle number for Cell 2 ( ⁇ ), Cell 6 ( ⁇ ), and Cell 7 ( ⁇ ), as described in Figure 10. 'Example 5(b).
  • Figure 11 shows proton nuclear magnetic resonance ( 1 H NMR) spectra for the solution samples of Film 4 before cycling (blue) and after cycling (red), as described in Example 6(a).
  • Figure 12 shows a graph of the amount of hydrogen sulphide (H2S) gas generated (mL/g) as a function of time (hours) for a powder of LÎ 6 PS 5 CI coated with decane (broken line), coated with the mixture decane: squalene (85:15 by volume) (dashed line-dot-dot line) and coated with the mixture decane: squalene (75:25 by volume) (solid line), as described in Example 6(b).
  • H2S hydrogen sulphide
  • the present technology relates to a potting material comprising at least one branched or linear unsaturated aliphatic hydrocarbon having 10 to 50 carbon atoms and having at least one carbon-carbon double or triple bond for use in an electrochemical cell.
  • the unsaturated aliphatic hydrocarbon as defined here is characterized by a boiling point above approximately 150°C.
  • the unsaturated aliphatic hydrocarbon is characterized by a boiling point ranging from about 150°C to about 675°C, or from about 155°C to about 670°C, or from from about 160°C to about 665°C, or ranging from about 165°C to about 660°C, or ranging from about 170°C to about 655°C, upper and lower limits included.
  • the unsaturated aliphatic hydrocarbon as herein defined includes a single carbon-carbon double or triple bond, for example, an alkene, alkyne, or acyclic olefin.
  • the unsaturated aliphatic hydrocarbon includes at least two conjugated or unconjugated carbon-carbon double bonds, for example, an alkadiene, an alcatriene, and so on, or a polyene.
  • the unsaturated aliphatic hydrocarbon includes at least two carbon-carbon triple bonds, for example, or an alkadiyne, an alcatriyne, and so on, or a polyyne.
  • the unsaturated aliphatic hydrocarbon includes at least one carbon-carbon double bond and at least one carbon-carbon triple bond.
  • unsaturated aliphatic hydrocarbons having at least one carbon-carbon double bond as defined herein include decene, dodecene, undecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, 1,9-decadiene, docosene, hexacosene, eicosene, tetracosene, squalene, farnesene, b-carotene, pinenes, dicyclopentadiene, camphene, Ga-phellandrene, b-phellandrene, terpinenes, b-myrcene, limonene, 2-carene, sabinene, Ga-
  • the unsaturated aliphatic hydrocarbon is chosen from decene, dodecene, undecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, 1,9-decadiene, docosene, hexacosene, eicosene, tetracosene, squalene, b-carotene, and combinations thereof.
  • the unsaturated aliphatic hydrocarbon is chosen from decene, undecene, squalene, octadecene, b-carotene and a combination of at least two of these.
  • the unsaturated aliphatic hydrocarbon includes squalene.
  • the unsaturated aliphatic hydrocarbon includes farnesene.
  • the unsaturated aliphatic hydrocarbon includes a mixture including squalene and farnesene.
  • Non-limiting examples of unsaturated aliphatic hydrocarbons having at least one carbon-carbon triple bond as defined herein include decyne, dodecyne, octadecyne, hexadecyne, tridecyne, tetradecyne, docosyne, and a combination at least two of these.
  • the coating material as defined here is a mixture comprising the unsaturated aliphatic hydrocarbon as defined here and at least one additional component.
  • the additional component can be an alkane, for example an alkane having 10 to 50 carbon atoms.
  • the additional component can be a mixture comprising an alkane as defined here and a polar solvent.
  • Non-limiting examples of polar solvents include tetrahydrofuran, acetonitrile, /V, /V-dimethylformamide and a miscible combination of two or more of these.
  • the additional component is decane.
  • the present technology also relates to coated particles for use in an electrochemical cell. More particularly, the coated particles include: a core comprising an electrochemically active material, an electronically conductive material or an ionically conductive inorganic material; and a potting material as herein defined disposed on the surface of said core.
  • the coating material can form a homogeneous coating layer on the surface of the core. That is, it can form a substantially uniform coating layer on the surface of the core.
  • the coating material can form a coating layer on at least part of the surface of the core. In other words, it can be dispersed heterogeneously on the surface of the core.
  • volume or the mass ratio of the coating material and the material of said core as well as the conditions of the coating process influence the degree of coverage of the surface of said core by the coating material and/or the homogeneity of coated particle samples.
  • coated particles as defined here in electrochemical applications is also envisaged.
  • the coated particles can be used in electrochemical cells, electrochemical accumulators, in particular in so-called all-solid batteries.
  • the coated particles can be used in an electrode material, in an electrolyte, or at the interface between the two as an additional layer.
  • the present technology also relates to a process for manufacturing coated particles as defined here, the process comprising at least one step of coating at least part of the surface of the core with the coating material.
  • the coating step can be performed by any compatible coating method.
  • the coating step can be carried out by a dry or wet coating process.
  • the coating step can be carried out by a wet coating process, for example, by a mechanical coating process, such as a process of mixing, grinding, or mechanosynthesis.
  • the method further comprises a step of grinding (or pulverizing) the electrochemically active material, the electronically conductive material or the ionically conductive inorganic material of said core of the particle coated.
  • the coating and milling steps may be performed simultaneously, sequentially, or may partially overlap in time.
  • the milling step can be performed before the coating step.
  • the coating and grinding steps are carried out simultaneously, for example, using a planetary mill or a planetary micromill.
  • the coating and grinding steps can be carried out at a speed of rotation and for a determined duration making it possible to obtain an optimum particle size or diameter, a degree of coverage of the surface of the core of the particle by the desired coating material, and/or a desired homogeneity of the samples of coated particles.
  • the particles are sulfide-based ceramic particles (eg, Li 6 PS 5 CI argyrodite particles).
  • the coating and grinding steps are carried out at a rotational speed of approximately 300 rpm for approximately 7.5 hours in order to obtain coated Li 6 PS 5 CI particles having a final particle size less than or equal to approximately 1 ⁇ m .
  • the method further comprises a step of drying the coated particles.
  • the drying step can be performed to remove moisture and/or residual solvent.
  • the drying process can be carried out at low temperature and for a determined duration in order to dry the coated particles, and this, without evaporating the coating material or without evaporating the coating material significantly.
  • the drying step can be carried out at a temperature below the boiling point of the unsaturated aliphatic hydrocarbon of the coating material, and this, for a determined duration so as not to evaporate the latter or not to evaporate this significantly.
  • the coating material comprises a mixture
  • at least one unsaturated aliphatic hydrocarbon does not evaporate completely during the drying step, and therefore, the latter remains present in the coating layer placed on the surface of the particle nucleus.
  • the mixture comprises an additional component (for example, an alkane or a mixture comprising an alkane and a polar solvent as defined previously)
  • this can be partially or completely evaporated during the drying step.
  • the drying step can be carried out at a temperature of approximately 80° C. for a duration of approximately 5 hours.
  • the composition of said mixture comprises at least approximately 2% by volume of the unsaturated aliphatic hydrocarbon as defined here, and this, during the coating step .
  • the composition of said mixture comprises at least approximately 3%, or at least approximately 4%, or at least approximately 5% by volume of the unsaturated aliphatic hydrocarbon as defined here, and this, during step d 'coating.
  • the method further comprises a coating step (also called spreading) of a suspension comprising said coated particles, said coating step being carried out, for example, by at least one method of coating with doctor blade coating, comma coating method, reverse comma coating method ), a printing method such as etching ("engraving coating” in English), or a slot coating method ("slot-die coating” in English).
  • said coating step is carried out by a doctor blade coating method.
  • the suspension comprising said coated particles can be coated on a substrate or support film, said substrate or support film being subsequently removed.
  • the suspension comprising said particles can be coated directly on a current collector.
  • the present technology also relates to an electrode material comprising: coated particles as defined herein, wherein the core comprises an electrochemically active material; and/or an electrochemically active material and coated particles as defined herein.
  • said electrode material is a positive electrode material and the electrochemically active material is chosen from a metal oxide, a metal sulphide, a metal oxysulphide, a metal phosphate, a metal fluorophosphate, a metal oxyfluorophosphate, a metal sulfate, a metal halide (eg, a metal fluoride), sulfur, selenium, and a combination of at least two of these.
  • the electrochemically active material is chosen from a metal oxide, a metal sulphide, a metal oxysulphide, a metal phosphate, a metal fluorophosphate, a metal oxyfluorophosphate, a metal sulfate, a metal halide (eg, a metal fluoride), sulfur, selenium, and a combination of at least two of these.
  • the metal of the electrochemically active material is chosen from titanium (Ti), iron (Fe), manganese (Mn), vanadium (V), nickel (Ni), cobalt (Co), aluminum (Al), chromium (Cr), copper (Cu), zirconium (Zr), niobium (Nb) and their combinations, when compatible.
  • the electrochemically active material may optionally further comprise an alkali or alkaline-earth metal, for example, lithium (Li), sodium (Na), potassium (K) or magnesium (Mg).
  • Non-limiting examples of electrochemically active materials include lithium and metal phosphates, complex oxides, such as LiM'PC (where M' is Fe, Ni, Mn, Co, or a combination thereof), UV3O8, V2O5, LiM ⁇ C , LiM”0 2 (where M” is Mn, Co, Ni, or a combination thereof), Li(NiM”')0 2 (where M'” is Mn, Co, Al, Fe, Cr, Ti, or Zr, or a combination thereof) and combinations thereof, when compatible.
  • LiM'PC where M' is Fe, Ni, Mn, Co, or a combination thereof
  • UV3O8 V2O5 LiM ⁇ C , LiM”0 2 (where M” is Mn, Co, Ni, or a combination thereof)
  • Li(NiM”')0 2 where M'” is Mn, Co, Al, Fe, Cr, Ti, or Zr, or a combination thereof
  • the electrochemically active material is an oxide or a phosphate such as those described above.
  • the electrochemically active material is a lithium manganese oxide, wherein the manganese may be partially substituted with a second transition metal, such as a lithium nickel manganese cobalt oxide (NMC). ).
  • the electrochemically active material is lithium iron phosphate.
  • the electrochemically active material is a lithium metal phosphate containing manganese such as those described above, for example, the lithium metal phosphate containing manganese is a lithium iron and manganese phosphate (LiMni- x Fe x P0 4 , where x is between 0.2 and 0.5).
  • said electrode material is a negative electrode material and the electrochemically active material is chosen from a non-alkaline and non-alkaline-earth metal (for example, indium (In), germanium ( Ge) and bismuth (Bi)), an intermetallic compound (for example, SnSb, TiSnSb, Cu 2 Sb, AlSb, FeSb 2 , FeSn 2 and CoSn 2 ), a metal oxide, a metal nitride, a phosphide of metal, a metal phosphate (for example, LiTÎ 2 (P0 4 ) 3 ), a metal halide (for example, a metal fluoride), a metal sulphide, a metal oxysulphide, a carbon (for example, the graphite, graphene, reduced graphene oxide, hard carbon, soft carbon, exfoliated graphite and amorphous carbon), silicon (Si), silicon-carbon composite (Si-C), silicon oxide (SiO x)
  • the oxide of metal may be selected from compounds of formula M”” b O c (where M”” is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof; and b and c are numbers such that the c:b ratio is in the range from 2 to 3) (for example, M0O 3 , M0O 2 , M0S 2 , V 2 O 5 , and TiNb 2 0 7 ), spinel oxides (for example, N ⁇ Oq 2 q 4 , ZhOq 2 q 4 , MnCo 2 0 4 , CUC0 2 O 4 , and CoFe 2 C> 4 ) and LiM””O (where M'”” is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination of at least two of these) (for example, a lithium titanate (such as Li 4 Ti 5 Oi 2 ) or an oxide lithium and molybdenum (such
  • the electrochemically active material can optionally be doped with other elements included in smaller quantities, for example to modulate or optimize its electrochemical properties.
  • the electrochemically active material can be doped by the partial substitution of the metal by other ions.
  • the electrochemically active material can be doped with a transition metal (e.g. Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn or Y) and/or a metal other than a transition metal (for example, Mg, Al or Sb).
  • a transition metal e.g. Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn or Y
  • a metal other than a transition metal for example, Mg, Al or Sb
  • the electrochemically active material can be in the form of particles (eg, microparticles and/or nanoparticles) which can be freshly formed or from a commercial source.
  • the coating material forms a coating layer on the surface of the electrochemically active material and the coating material is disposed on the surface of the coating layer.
  • the electrochemically active material may be in the form of particles coated with a layer of coating material.
  • the coating material may be an electronically conductive material, for example, a conductive carbon coating.
  • the coating material can make it possible to substantially reduce the interfacial reactions at the interface between the electrochemically active material and an electrolyte, for example, a solid electrolyte, and in particular, a solid electrolyte of the sulfide-based ceramic type (for example, based on LÎ6PS 5 CI).
  • the coating material can be chosen from LhSiOs, LiTa0 3 , UAIO 2 , LhO-ZrC ⁇ , LiNbC> 3 , their combinations, when compatible, and other similar materials.
  • the coating material comprises LiNbOs.
  • the electrode material as defined here further includes a conductive material.
  • the core of the coated particle comprises the electronic conductive material.
  • Non-limiting examples of electronically conductive material include a carbon source such as carbon black (eg, Ketjen TM carbon and Super P TM carbon), acetylene black (eg, Shawinigan carbon and Denka TM carbon fiber), graphite, graphene, carbon fibers (e.g., gas phase formed carbon fibers (VGCFs)), carbon nanofibers, carbon nanotubes (CNTs) and a combination of at least two of these.
  • the electronic conductive material if it is present in the electrode material, can be a modified electronic conductive material such as those described in the PCT patent application published under number WO2019/218067 (Delaporte et al .).
  • the modified electronic conductor material can be grafted with at least one aryl group of Formula I:
  • FG is a hydrophilic functional group; and n is a natural number in the range from 1 to 5, preferably n is in the range from 1 to 3, preferably n is 1 or 2, and more preferably n is 1.
  • hydrophilic functional groups include hydroxyl, carboxyl, sulfonic acid, phosphonic acid, amine, amide and other similar groups.
  • the hydrophilic functional group is a carboxyl or sulphonic acid functional group.
  • the functional group can optionally be lithiated by the exchange of a hydrogen by a lithium.
  • Preferred examples of an aryl group of Formula I are p-benzoic acid or p-benzenesulfonic acid.
  • the electronically conductive material is carbon black optionally grafted with at least one aryl group of Formula I.
  • the electronically conductive material can be a mixture comprising at least one conductive material modified electronics.
  • a mixture of carbon black grafted with at least one aryl group of Formula I and carbon fibers for example, gas phase formed carbon fibers (VGCFs)), carbon nanofibers, carbon nanotubes (NTCs) or a combination of two or more thereof.
  • VGCFs gas phase formed carbon fibers
  • NTCs carbon nanotubes
  • the electrode material as defined here further includes an additive.
  • the core of the coated particle includes the additive.
  • the additive is chosen from inorganic ionic conductive materials, inorganic materials, glasses, glass-ceramics, ceramics, including nano-ceramics (for example, Al 2 O 3 , T1O 2 , S1O 2 and other similar compounds ), salts (eg lithium salts) and a combination of two or more thereof.
  • the additive may be an inorganic ionic conductor chosen from compounds of the LISICON, thio-LISICON, argyrodite, garnet, NASICON, perovskite type, oxides, sulphides, phosphides, fluorides , sulfur halides, phosphates, thio-phosphates, in crystalline and/or amorphous form, and a combination of at least two of these.
  • the additive if it is present in the electrode material, can be ceramic, glass or glass-ceramic particles based on fluoride, phosphide, sulphide, oxysulphide, oxide, or a combination of at least two of these.
  • Non-limiting examples of ceramic, glass or glass-ceramic particles include inorganic compounds of the formulas MLZO (e.g., M7La3Zr2Oi2, M(7- a) La3Zr2AlbOi2, M(7- a) La3Zr2GabOi2, M(7- a) La3Zr (2-b)TabOi2, and M(7- a >La3Zr(2-b)Nb b Oi 2 );MLTaO (for example, M7La 3 Ta 2 Oi2, M 5 La3Ta20i 2 , and M6La3Ta1.5Y0.5O12); MLSnO (e.g., M7La3Sn20i2); MAGP (e.g., Mi +a Al a Ge2- a (P04)3); MATP (e.g., Mi +a Al a Ti2- a (P04)3,); MLTiO (par M3 a La(2/3- a >Ti03
  • M is an alkali metal ion, an alkaline earth metal ion or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
  • X is selected from F, Cl, Br, I or a combination of at least two of these; a, b, c, d, e and f are numbers other than zero and are independently in each formula selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are independently in each formula selected to yield a stable compound.
  • M is selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba or a combination of at least two of these.
  • M comprises Li and may further comprise at least one of Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba or a combination of at least two of these.
  • M comprises Na, K, Mg or a combination of at least two of these.
  • the additive if present in the electrode material, may be sulfide-based ceramic particles, for example, argyrodite-type ceramic particles of the formula Li 6 PS 5 X (where X is Cl, Br, I or a combination of two or more thereof).
  • the additive is LiePSsCI argyrodite.
  • the electrode material as defined here further includes a binder.
  • the binder is chosen for its compatibility with the various elements of an electrochemical cell. Any known compatible binder is contemplated.
  • the binder can be chosen from a polymer binder of the polyether, polyester, polycarbonate, fluorinated polymer and water-soluble binder (water-soluble).
  • the binder is a fluorinated polymer such as polyvinylidene fluoride (PVDF) or polytetrafluoroethylene (PTFE).
  • the binder is a water-soluble binder such as styrene-butadiene rubber (SBR), acrylonitrile-butadiene rubber (NBR), hydrogenated NBR (HNBR), epichlorohydrin rubber (CHR) , or acrylate rubber (ACM), and optionally comprising a thickening agent such as carboxymethylcellulose (CMC), or a polymer such as poly(acrylic acid) (PAA), poly(methyl methacrylate) (PMMA) or a combination of at least two of these.
  • the binder is a polyether-type polymer binder.
  • the polyether type polymer binder is linear, branched and/or cross-linked and is based on poly(ethylene oxide) (POE), poly(propylene oxide) (POP) or a combination of the two (such as an EO/PO copolymer), and optionally comprises crosslinkable units.
  • the crosslinkable segment of the polymer can be a polymer segment comprising at least one functional group crosslinkable in a multidimensional manner by irradiation or by heat treatment.
  • the binder if it is present in the electrode material, can comprise a mixture including a polymer based on polybutadiene and a polymer comprising monomer units based on norbornene derived from the polymerization of a compound of Formula II: in which,
  • R 1 and R 2 are independently and at each occurrence chosen from a hydrogen atom, a carboxyl group (-COOH), a sulphonic acid group (-SO3H), a hydroxyl group (-OH), a fluorine atom and a chlorine atom.
  • At least one of R 1 or R 2 is chosen from -COOH, -SO 3 H, -OH, -F and -Cl which means that at least one of R 1 or R 2 is different from a hydrogen atom.
  • R 1 is a —COOH group and R 2 is a hydrogen atom.
  • At least one of R 1 or R 2 is a —COOH group and the norbornene-based monomer units are norbornene-based monomer units functionalized with a carboxylic acid.
  • R 1 is a —COOH group and R 2 is a hydrogen atom.
  • R 1 and R 2 are both —COOH groups.
  • the binder if it is present in the electrode material, can comprise a mixture including a polymer based on polybutadiene and a polymer of Formula III: in which,
  • R 1 and R 2 are as defined previously, and n is a natural number chosen so that the weight-average molecular weight of the polymer of Formula III is between approximately 10,000 g/mol and approximately 100,000 g/mol as as determined by gel permeation chromatography (GPC), upper and lower limits included.
  • GPC gel permeation chromatography
  • the weight-average molecular weight of the polymer of Formula III is between approximately 12,000 g/mol and approximately 85,000 g/mol, or between approximately 15,000 g/mol and approximately 75,000 g/mol, or between about 20,000 g/mol and about 65,000 g/mol, or between about 25,000 g/mol and about 55,000 g/mol, or between about 25,000 g/mol and about 50,000 g/mol as determined by GPC, upper and lower bounds included.
  • R 1 and R 2 are —COOH groups.
  • the polymer is of Formula III(a):
  • R 2 and n are as defined previously.
  • the polymer is of Formula III(b):
  • the norbornene-based polymer of Formula II, or the polymer of Formula III, III(a) or III(b) is a homopolymer.
  • the polymerization of the norbornene-based monomer of Formula II can be carried out by all compatible and known polymerization methods.
  • the polymerization of the compound of Formula II can be carried out by the synthetic process described by Commarieu, B. et al. (Commarieu, Basile, et al. "Ultrahigh T g Epoxy Thermosets Based on Insertion Polynorbornenes", Macromolecules, 49.3 (2016): 920-925).
  • the polymerization of the compound of Formula II can also be carried out by an addition polymerization process.
  • norbornene-based polymers produced by an addition polymerization process are substantially stable under severe conditions (eg, acidic and basic conditions).
  • Addition polymerization of norbornene-based polymers can be accomplished using inexpensive norbornene-based monomers.
  • the glass transition temperature (T g ) obtained with the norbornene-based polymers produced by this polymerization route can be equal to or greater than about 300°C, for example, as high as 350°C.
  • the polybutadiene-based polymer can be characterized by a substantially higher elasticity or flexibility and/or by a substantially lower glass transition temperature (T v ) than those of the norbornene-based polymer of Formulas III , lll(a) or lll(b).
  • T v glass transition temperature
  • the polybutadiene-based polymer can be polybutadiene.
  • the polybutadiene-based polymer can be functionalized polybutadiene or a polymer derived from polybutadiene.
  • functionalized polybutadiene or polymer derived from polybutadiene may be characterized by substantially higher elasticity or flexibility, and/or by substantially lower glass transition temperature (T v ) and /or can improve the mechanical or cohesive properties of the electrode binder.
  • the polymer based on polybutadiene is chosen from epoxidized polybutadienes, for example epoxidized polybutadienes having reactive terminal groups.
  • the reactive terminal groups can be hydroxyl groups.
  • the epoxidized polybutadiene can comprise repeating units of Formulas IV, V and VI:
  • the mass average molecular weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI can be between approximately 1000 g/mol and approximately 1500 g/mol as determined by GPC, upper limits and lower included.
  • the epoxide equivalent weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI is between about 100 g/mol and about 600 g/mol as determined by GPC, upper and lower bounds included .
  • the epoxy equivalent weight corresponds to the mass of resin which contains 1 mole of epoxide functional groups.
  • the epoxidized polybutadiene is of Formula VII: wherein m is a whole number chosen such that the mass average molecular weight of the epoxidized polybutadiene of Formula VII is between about 1000 g/mol and about 1500 g/mol as determined by GPC, upper bounds and bottoms included; and the epoxide equivalent weight is between about 100 g/mol and about 600 g/mol as determined by GPC, upper and lower bounds inclusive.
  • the mass average molecular weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI or of the epoxidized polybutadiene of Formula VII is between approximately 1050 g/mol and approximately 1450 g/mol, or between approximately 1100 g/mol and approximately 1400 g/mol, or between approximately 1150 g/mol and approximately 1350 g/mol, or between approximately 1200 g/mol and approximately 1350 g/mol, or between approximately 1250 g/mol and about 1350 g/mol as determined by GPC, upper and lower limits included.
  • the mass-average molecular weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI or epoxidized polybutadiene of Formula VII is about 1300 g/mol, as determined by GPC.
  • the epoxy equivalent weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI or of the epoxidized polybutadiene of Formula VII is between approximately 150 g/mol and approximately 550 g/mol, or between approximately 200 g/mol and about 550 g/mol, or between about 210 g/mol and about 550 g/mol, or between about 260 g/mol and about 500 g/mol as determined by GPC, upper and lower bounds included.
  • the epoxide equivalent weight of the epoxidized polybutadiene comprising repeating units of Formulas IV, V and VI or of the epoxidized polybutadiene of Formula VII is between approximately 400 g/mol and approximately 500 g/mol, or between about 260 g/mol and about 330 g/mol as determined by GPC, upper and lower limits included.
  • the epoxidized polybutadiene of Formula VII is a commercial epoxidized polybutadiene resin having terminal hydroxyl groups of the Poly bd MC 600E or 605E type marketed by Cray Valley.
  • the physico-chemical properties of these resins are presented in Table 1.
  • the electrode binder comprises a mixture of polymers comprising at least a first polymer and at least a second polymer.
  • the first polymer is the polybutadiene-based polymer and the second polymer is the polymer comprises norbornene-based monomer units derived from the polymerization of the compound of Formula II or the polymer of Formula III, III(a) or III(b) .
  • the "first polymer:second polymer” ratio is in the range from about 6:1 to about 2:3, upper and lower bounds inclusive.
  • the ratio "first polymer: second polymer” is comprised in the range of about 5.5:1 to about 2:3, or about 5:1 to about 2:3, or about 4.5:1 to about 2:3, or ranging from about 4:1 to about 2:3, or ranging from about 6:1 to about 1:1, or ranging from about 5.5:1 to about 1:1, or ranging from about 5: 1 to about 1:1, or ranging from about 4.5:1 to about 1:1, or ranging from about 4:1 to about 1:1, upper and lower bounds inclusive.
  • the “first polymer:second polymer” ratio is comprised in the interval going from approximately 4:1 to approximately 1:1, upper and lower limits included.
  • the present technology also relates to an electrode comprising an electrode material as defined herein.
  • the electrode may be on a current collector (eg, aluminum or copper foil).
  • the electrode can be self-supporting.
  • the present technology also relates to an electrolyte comprising coated particles as defined herein, wherein the core of the coated particle comprises an ion-conductive inorganic material.
  • the electrolyte can be chosen for its compatibility with the various elements of the electrochemical cell. Any type of compatible electrolyte is envisaged.
  • the electrolyte is a liquid electrolyte comprising a salt in a solvent.
  • the electrolyte is a gel electrolyte comprising a salt in a solvent and optionally a solvating polymer.
  • the electrolyte is a solid polymer electrolyte comprising a salt in a solvating polymer.
  • the electrolyte comprises an inorganic solid electrolyte material, for example, the electrolyte can be a ceramic type solid electrolyte.
  • the electrolyte is a polymer-ceramic hybrid solid electrolyte.
  • the inorganic ion-conductive material is chosen from inorganic ion-conductive materials, glasses, glass-ceramics, ceramics, nano-ceramics and a combination of at least two of these.
  • the inorganic ion-conductive material comprises a ceramic, a glass or a glass-ceramic in crystalline and/or amorphous form.
  • the ceramic, glass or glass-ceramic particles can be based on fluoride, phosphide, sulphide, oxysulphide, oxide, or a combination of these.
  • the ion-conductive inorganic material is chosen from compounds of LISICON, thio-LISICON, argyrodites, garnets, NASICON, perovskites, oxides, sulphides, oxysulphides, phosphides, fluorides, of crystalline form and /or amorphous, and a combination of two or more thereof.
  • the ion-conductive inorganic material is chosen from inorganic compounds of formulas MLZO (for example, M7La 3 Zr20i2, M ( 7- a) La3Zr2Al b Oi2, M(7-a)La 3 Zr 2 GabOi 2 , M ( 7-a)La 3 Zr(2-b)TabOi2, and M ( 7-a)La 3 Zr ( 2-b)NbbOi2); MLTaO (e.g., M7La 3 Ta20i2, M 5 La 3 Ta20i2, and M6La3Ta1.5Y0.5O12); MLSnO (e.g., M7La 3 Sn20i2); MAGP (for example, Mi +a Al a Ge 2-a (P0 4 ) 3 ); MATP (for example, Mi +a Al a Ti 2-a (P0 4 ) 3, ); MLTiO (for example, M 3a La(2/ 3 -a)Ti0 3 ); MZP
  • M is an alkali metal ion, an alkaline earth metal ion or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
  • X is selected from F, Cl, Br, I or a combination of at least two of these; a, b, c, d, e and f are numbers other than zero and are independently in each formula selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are independently in each formula selected to obtain a stable compound.
  • the inorganic ion-conductive material is chosen from inorganic compounds of the argyrodite type of formula LÎ 6 PS 5 X, in which X is Cl, Br, I or a combination of at least two of these.
  • the ionically conductive inorganic material is LI 6 PS 5 CI.
  • the salt if present in the electrolyte, can be an ionic salt, such as a lithium salt.
  • lithium salts include lithium hexafluorophosphate (LiPFe), lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), lithium bis(fluorosulfonyl)imide (LiFSI), 2-trifluoromethyl-4,5 -lithium dicyano-imidazolate (LiTDI), lithium 4,5-dicyano-1,2,3-triazolate (LiDCTA), lithium bis(pentafluoroethylsulfonyl)imide (LiBETI), lithium difluorophosphate (LiDFP), lithium tetrafluoroborate (L1BF4), lithium bis(oxalato)borate (LiBOB), lithium nitrate (UNO3), lithium chloride (LiCI), lithium bromide (LiBr), lithium fluor
  • LiPFe lithium he
  • the solvent if present in the electrolyte, can be a non-aqueous solvent.
  • solvents include cyclic carbonates such as ethylene carbonate (EC), propylene carbonate (PC), butylene carbonate (BC), and vinylene carbonate (VC); acyclic carbonates such as dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC) and dipropyl carbonate (DPC); lactones such as ⁇ -butyrolactone (g-BL) and ⁇ -valerolactone (g-VL); acyclic ethers such as 1,2-dimethoxyethane (DME), 1,2-diethoxyethane (DEE), ethoxy methoxy ethane (EME), trimethoxymethane and ethylmonoglyme; cyclic ethers such as tetrahydrofuran, 2-methyltetrahydrofuran, 1,
  • the electrolyte is a gel electrolyte or a polymer gel electrolyte.
  • the gel polymer electrolyte may comprise, for example, a polymer precursor and a salt (for example, a salt as defined above), a solvent (for example, a solvent as defined above) and a polymerization initiator and / or crosslinking, if necessary.
  • examples of gel electrolytes include, without limitation, gel electrolytes such as those described in PCT patent applications published under the numbers WO2009/111860 (Zaghib et al.) and WO2004/068610 (Zaghib et al.).
  • a gel electrolyte or a liquid electrolyte as defined above can also impregnate a separator such as a polymer separator.
  • separators include, without limitation, polyethylene (PE), polypropylene (PP), cellulose, polytetrafluoroethylene (PTFE), poly(vinylidene fluoride) (PVDF) and polypropylene-polyethylene-polypropylene (PP) separators. /PE/PP).
  • the separator is a commercial polymer separator of the Celgard TM type.
  • the electrolyte is a solid polymer electrolyte.
  • the solid polymer electrolyte can be chosen from all known solid polymer electrolytes and can be chosen for its compatibility with the various elements of an electrochemical cell.
  • Solid polymer electrolytes generally comprise a salt as well as one or more solid polar polymer(s), optionally crosslinked.
  • Polyether-type polymers such as those based on poly(ethylene oxide) (POE)
  • POE poly(ethylene oxide)
  • the polymer can be cross-linked. Examples of such polymers include branched polymers, for example, star polymers or comb polymers such as those described in the PCT patent application published under number WO2003/063287 (Zaghib et al.).
  • the solid polymer electrolyte can include a block copolymer composed of at least one solvation segment of lithium ions and optionally of at least one crosslinkable segment.
  • the ion solvation segment lithium is chosen from homo- or copolymers having repeating units of Formula VIII:
  • R is chosen from a hydrogen atom, and a CiC-ioalkyl group or a -(CH 2 -O-R a R b ) group;
  • R a is (CH 2 -CH 2 -0) y ;
  • R b is chosen from a hydrogen atom and a CiC-ioalkyl group; x is an integer selected from the range of 10 to 200,000; and y is an integer selected from the range 0 to 10.
  • the crosslinkable segment of the copolymer is a polymer segment comprising at least one functional group crosslinkable in a multidimensional manner by irradiation or by heat treatment.
  • the electrolyte is a liquid electrolyte, a gel electrolyte or a solid polymer electrolyte
  • the coated particles as defined here can be present as an additive in the electrolyte.
  • the coated particles as herein defined may be present as an inorganic (ceramic) solid electrolyte material.
  • the electrolyte may also optionally include additional components such as ionic conductive materials, inorganic particles, glass or ceramic particles as defined above and other additives of the same type.
  • the additional component may be a dicarbonyl compound such as those described in the PCT patent application published under number WO2018/116529 (Asakawa et al.).
  • the additional component may be poly(ethylene-alt-maleic anhydride) (PEMA).
  • PEMA poly(ethylene-alt-maleic anhydride)
  • the additional component can be chosen for its compatibility with the different elements of an electrochemical cell.
  • the additional component can be substantially dispersed in the electrolyte.
  • the additional component may be present in a separate layer.
  • the present technology also relates to a coating material for a current collector comprising coated particles as defined herein, wherein the core of the coated particle comprises an electronically conductive material.
  • the coated particles can be coated conductive carbon particles that can be coated onto a metallic current collector foil (e.g., aluminum or copper foil).
  • a current collector comprising the coating material coated on a metal foil is also contemplated.
  • the present technology also relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which at least one of the positive electrode or the negative electrode is as defined herein at or comprises a material of electrode as defined here.
  • the negative electrode is as defined here or comprises an electrode material as defined here.
  • the electrochemically material of the negative electrode can be chosen for its electrochemical compatibility with the different elements of the electrochemical cell as defined here.
  • the electrochemically material of the negative electrode material may possess a substantially lower oxidation-reduction potential than that of the electrochemically active material of the positive electrode.
  • the positive electrode is as defined here or comprises an electrode material as defined here and the negative electrode includes an electrochemically active material chosen from among all known compatible electrochemically active materials.
  • the electrochemically active material of the negative electrode can be chosen for its electrochemical compatibility with the various elements of the electrochemical cell as defined here.
  • Non-limiting examples of electrochemically active materials of the negative electrode include alkali metals, alkaline-earth metals, alloys comprising at least one alkali or alkaline-earth metal, non-alkaline and non-alkaline-earth metals (for example, indium (In), germanium (Ge) and bismuth (Bi)), and alloys or intermetallic compounds (eg example, SnSb, TiSnSb, Cii2Sb, AlSb, FeSb2, FeSri2 and CoSri2).
  • the electrochemically active material of the negative electrode may be in the form of a film having a thickness in the range of from about 5 ⁇ m to about 500 ⁇ m and preferably in the range of from about 10 ⁇ m to about 10 ⁇ m. about 100 pm, upper and lower bounds included.
  • the electrochemically active material of the negative electrode can comprise a film of metallic lithium or of an alloy including or based on metallic lithium.
  • the positive electrode can be prelithiated and the negative electrode can be initially (i.e. before the cycling of the electrochemical cell) substantially or completely free of lithium.
  • the negative electrode can be lithiated in situ during the cycling of said electrochemical cell, in particular during the first charge.
  • metallic lithium can be deposited in situ on the current collector (for example, a copper current collector) during the cycling of the electrochemical cell, in particular during the first charge.
  • an alloy including metallic lithium can be generated on the surface of a current collector (for example, an aluminum current collector) during the cycling of the electrochemical cell, in particular during the first charge. It is understood that the negative electrode can be generated in situ during the cycling of the electrochemical cell, in particular during the first charge.
  • the positive electrode and the negative electrode are both as defined here or both comprise an electrode material as defined here.
  • the present technology also relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which the electrolyte is as defined herein.
  • the present technology also relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which at least one of the positive electrode and the negative electrode is on a current collector as defined here or comprising a coating material as herein defined.
  • the present technology also relates to a battery comprising at least one electrochemical cell as defined here.
  • the battery may be a battery primary (battery) or secondary (accumulator).
  • the battery is chosen from the group consisting of a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a magnesium battery, a a magnesium-ion battery, a potassium battery and a potassium-ion battery.
  • the battery is a so-called all-solid battery.
  • the coating material can provide a substantial reduction in the number and size of particle agglomerates in the dispersion.
  • the potting material allows a substantial reduction in the number and size of agglomerates of particles of electronic conductive material or of the ceramic type electrolyte material.
  • repulsive interactions linked to the coating material can allow a better dispersion of the constituents of the positive electrode in the dispersion, and this, by the modification or not of the other constituents allowing this type of interactions.
  • the repulsive interactions can be p-p type and/or polar interactions.
  • the coating material can also substantially limit the parasitic reactions with the other constituents of the electrochemical cell, and thus improve the cycling and aging stability of the electrochemical cell.
  • the coating material can also substantially limit the resistance to charge transfer and can make it possible to substantially improve the ionic and/or electronic conductivity thanks to the double or triple bonds present in the coating material.
  • the p orbitals of the coating material as defined here can allow orbital delocalization and therefore orbital interactions with ions and/or electrons.
  • the potting material can also substantially improve the safety of the electrochemical cell, for example, by reducing gas generation.
  • the coating when applied to a particle of sulfide-based ceramic-type electrolyte material, can substantially reduce the amount of hydrogen sulfide (H 2 S) generated by exposure of the coated material to humidity or ambient air.
  • the coating material can also include organic compounds or molecules making it possible to trap the gas molecules (for example, H2S) and/or making it possible to form a barrier in order to reduce the introduction of humidity in order to reduce the formation of H2S.
  • the coating of the LiePSsCI particles was carried out by a method of grinding the particles in a wet way.
  • the coating of the LiePSsCI particles was carried out using a PULVERISETTE MC 7 planetary micromill. 4 g of LiePSsCI particles were placed in an 80 ml zirconium oxide (or zirconia) grinding jar. A mixture comprising 20 ml of anhydrous decane and 7 ml of squalene (75:25 by volume) as well as grinding balls having a diameter of 2 mm were added to the jar. The LiePSsCI particles and the mixture of decane and squalene were combined by grinding at a speed of about 300 rpm for about 7.5 hours to produce LiePSsCI particles coated with the mixture of decane and squalene. The particles thus obtained are subsequently dried under vacuum at a temperature of about 80°C.
  • the same coating process was carried out (i) with decane, (ii) with a mixture of decane and squalene (90:10 by volume), (iii) with a mixture of decane and farnesene (85:15 by volume), and (iV) with a mixture of decane, farnesene and squalene (85:7.5:7.5 by volume).
  • Example 2 Preparation of the modified electronic conductive material a) Coating of the particles of electronic conductive material with a mixture of decane and squalene (75:25 by volume) The coating process described in Example 1 is used to coat the electronically conductive material. More specifically, the wet particle milling process is used to coat the coating material comprising a mixture of decane and squalene (75:25 by volume) with carbon black. b) Grafting of particles of electronically conductive material with at least one aryl group of Formula I
  • the mixture was vacuum filtered using a vacuum filtration assembly (Büchner type) and a nylon filter having a pore size of 0.22 ⁇ m.
  • the modified carbon black powder thus obtained was then washed successively with deionized water until a neutral pH was reached, then with acetone. Finally, the modified carbon black powder was then dried under vacuum at 100°C for at least one day before use.
  • Example 1 The Li 6 PS 5 CI particles coated with the mixture of decane and squalene (75:25 by volume) prepared in Example 1 were characterized by SEM imaging.
  • Figure 1 shows in (A) an image obtained by SEM of Ü 6 PS 5 CI particles before the grinding and coating step and in (B) an image obtained by SEM of LiePSsCI particles coated with the decane mixture and squalene (75:25 by volume) prepared in Example 1.
  • Scale bars represent 20 ⁇ m.
  • Figure 1(B) confirms the reduction in the size of the particles of LÎ 6 PS 5 CI as well as the presence of the coating thereon and does not show any agglomeration of said particles following the coating.
  • TGA Thermogravimetric analysis
  • the particles of LI 6 PS 5 CI coated with squalene prepared in Example 1 were characterized by ATG imaging.
  • thermogravimetric curves of squalene ( ⁇ ; curve 1) and of Ü 6 PS 5 CI particles coated with squalene prepared in Example 1 (o; curve 2) are presented in FIG. 2.
  • the thermogravimetric analyzes were carried out at a temperature rise rate of 10°C/min.
  • Figure 2 shows that squalene remains stable up to about 254°C, the temperature at which the onset of thermal degradation can be observed.
  • Figure 2 also shows a mass variation for the sample comprising the squalene-coated ⁇ 6 PS 5 CI particles at a similar temperature.
  • the proton and carbon nuclear magnetic resonance spectra ( 1 H and 13 C NMR) were obtained by the MAS technique (magic angle rotation) using a Bruker Avance MC NEO 500 MHz spectrometer equipped with a triple probe 4 mm resonance whose maximum speed of rotation at the magic angle is 15 kHz.
  • Figure 3 presents in (A) a 1 H NMR spectrum, and in (B) a 13 C NMR spectrum both obtained for the particles of Li 6 PS 5 CI coated with the mixture of decane and squalene (75:25 by volume) prepared in Example 1 and dried at a temperature of about 80°C under vacuum for about 5 hours.
  • Figure 4 presents a 1 H NMR spectrum obtained for the particles of LÎ 6 PS 5 CI coated with the mixture of decane and farnesene (85:15 by volume) prepared in Example 1 and dried at a temperature of approximately 80° C under vacuum for about 5 hours.
  • Figure 4 also presents a 1 H NMR spectrum, obtained for pure farnesene.
  • Figure 5 presents a 1 H NMR spectrum obtained for the particles of Ü 6 PS 5 CI coated with the mixture of decane and squalene and farnesene (85:7.5:7.5 by volume) prepared in Example 1 and dried at a temperature about 80°C under vacuum for about 5 hours.
  • Figure 5 also presents a 1 H NMR spectrum, obtained for pure farnesene and squalene.
  • the polymer solution was added to the dry powder mixture.
  • the mixture thus obtained was mixed for about 5 minutes using a planetary centrifugal mixer (Thinky Mixer).
  • An additional solvent, methoxybenzene, was added to the mixture in order to reach an optimum viscosity for coating, i.e. approximately 10,000 cP.
  • the suspension thus obtained was coated on an aluminum foil by a doctor blade coating method to obtain a positive electrode film applied to a current collector.
  • the positive electrode film was then dried under vacuum at a temperature of about 120°C for about 5 hours.
  • a positive electrode film with ⁇ 6 PS 5 CI particles without coating as an additive was also obtained for comparison by the method of the present example.
  • the aluminum foil could also be unmodified carbon coated aluminum foil or carbon coated aluminum foil encased in the potting material as defined herein.
  • composition of the positive electrode films is shown in Table 2. Table 2. Composition of positive electrode films
  • Example 4 Characterization of the Positive Electrode Films Prepared in Example 4(a) Morphological studies of the various positive electrode films were carried out using a scanning electron microscope (SEM) equipped with a detector equipped with an energy dispersive X-ray spectrometer (EDS).
  • SEM scanning electron microscope
  • EDS energy dispersive X-ray spectrometer
  • Figure 6 shows in (A) and (B) images obtained by SEM and elemental microanalyses by EDS allowing the analysis of the distribution of the elements (Ni and S) by mapping obtained respectively for Films 1 and 2 prepared at Example 4(a). Scale bars represent 100 ⁇ m.
  • FIG. 6(A) It is possible to observe in FIG. 6(A) the presence of sulfide agglomerates on the section of the positive reference electrode film comprising particles of U 6 PS 5 CI without coating (Film 1). Comparatively, FIG. 6(B) confirms the absence of these agglomerates during the analysis of the section of Film 2 including particles of U 6 PS 5 CI coated with the decane:squalene mixture (75:25 by volume).
  • the coating of the particles of U 6 PS 5 CI with unsaturated aliphatic hydrocarbons comprising at least one double or one triple bond allows their good dispersion and the absence of agglomerate.
  • Figure 7 shows in (A) an image obtained by SEM for Film 3 and an enlargement of this image, and in (B) an image obtained by SEM for Film 4 and an enlargement of this image.
  • the scale bars of the SEM images and their magnification represent 300 ⁇ m and 100 ⁇ m respectively.
  • Figure 7(A) it is possible to observe in Figure 7(A) the presence of carbon agglomerates on the section of Film 3 composed of a positive reference electrode film comprising particles of LiePSsCI coated with decane.
  • the presence of these carbon agglomerates could cause a decrease in electrochemical performance, particularly from the point of view of electronic percolation, and therefore stability and cycling performance.
  • Figure 7(B) confirms the absence of these agglomerates on the surface of Film 4 including LiePSsCI particles coated with the decane:squalene mixture (75:25 by volume).
  • ionic conductive inorganic particles by unsaturated aliphatic hydrocarbons comprising at least one double or triple bond coupled with the surface modification of electronic conductive material by polar groups allows a repulsion of these two types of particles and thus ensures a good dispersion and homogeneity of the composition in thickness and on the surface of the films.
  • Example 4(a) The electrochemical properties of the positive electrode films prepared in Example 4(a) were studied. a) Configurations of the electrochemical cells The electrochemical cells were assembled according to the following procedure.
  • Pellets 10 mm in diameter were taken from the positive electrode films prepared in Example 4(a).
  • Sulfide-based ceramic-like inorganic solid electrolytes were prepared by placing 80 mg of LiePSsCI sulfide-based ceramic on the surface of the positive electrode film pellets.
  • the film pellets of positive electrode including the layer of inorganic solid electrolyte were then compressed under a pressure of 2.8 tons using a press. They were then assembled, in a glove box, in CR2032 type button battery boxes facing metallic lithium electrodes 10 mm in diameter on aluminum and copper current collectors.
  • the electrochemical cells were assembled according to the configurations presented in Table 3.
  • This example illustrates the electrochemical behavior of electrochemical cells as described in Example 5(a).
  • Example 5(a) The electrochemical cells assembled in Example 5(a) were cycled between 4.3 V and 2.5 V vs Li/Li + at a temperature of 50°C. The formation cycle was carried out at a constant charge and discharge current of C/15. Then four cycles were performed at a constant charge and discharge current of C/10 followed by four cycles at a constant charge and discharge current of C/5. Finally, the aging experiments were performed at a constant charge and discharge current of C/3.
  • Figure 8 shows in (A) a graph of discharge capacity (mAh/g) and coulombic efficiency (%) as a function of the number of cycles, and in (B) a graph of the average potential in charge and in discharge (V) as a function of the number of cycles for Cell 1 (A) and for Cell 2 ( ⁇ ), as described in Example 3(a).
  • the cycling performances are substantially improved by the coating of the electronically conductive material with the coating materials as defined here. Indeed, as can be observed, Cell 2 exhibits improved capacity retention during long cycling experiments compared to Cell 1.
  • the coating of conductive inorganic particles ions by unsaturated aliphatic hydrocarbons comprising at least one double or triple bond coupled with the surface modification of electronically conductive material by polar groups allows repulsion of these two types of particles and ensures better ionic and electronic percolation which results in better capacitance retention and coulombic efficiency as well as a reduction in the average potential thanks to the reduction in the resistance to charge transfer.
  • Figure 9 shows in (A) a graph of discharge capacity (mAh/g) and coulombic efficiency (%) as a function of the number of cycles, and in (B) a graph of the average potential in charge and in discharge (V) according to the number of cycles for the
  • Figure 10 shows a graph of discharge capacity (mAh/g) and coulombic efficiency (%) versus number of cycles for Cell 2 ( ⁇ ), Cell 6 ( ), Cell 7 ( ⁇ ), as described in Example 3(a).
  • Cell 7 comprising LÎ 6 PS 5 CI particles coated with a mixture of decane, squalene and farnesene exhibits better cycling aging. This makes it possible to demonstrate the feasibility and the interest of coating the surface of particles with a mixture of several unsaturated aliphatic hydrocarbons. It is also possible to vary the ratios of these unsaturated aliphatic hydrocarbons in the mixture.
  • Example 6 Characterization of the properties of the coatings a) Characterization of the properties of the coatings after cycling by proton nuclear magnetic resonance ( 1 H NMR)
  • FIG 11 shows proton nuclear magnetic resonance ( 1 H NMR) analysis results for liquid samples obtained by extraction of Film 4 before cycling (blue) and after cycling (red) with tetrahydrofuran.
  • the 1 H NMR spectra were obtained using a Bruker Avance MC NEO NanoBay 300 MHz spectrometer equipped with a 5 mm broadband double resonance probe.
  • the solvent used was deuterated tetrahydrofuran (THF-d8).
  • Figure 12 shows a graph of the volume of gaseous H2S generated per gram of powder (mL/g) as a function of time (hours). Sulphide coating could therefore significantly reduce the amount of H2S generated, and thus improve the safety of electrochemical systems.

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EP22814657.7A 2021-06-03 2022-06-03 Beschichtungsmaterialien auf basis ungesättigter aliphatischer kohlenwasserstoffe und verwendungen davon in elektrochemischen anwendungen Pending EP4348733A1 (de)

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CA3120989A CA3120989A1 (fr) 2021-06-03 2021-06-03 Materiaux d'enrobage a base d'hydrocarbures aliphatiques insatures et leurs utilisations dans des applications electrochimiques
PCT/CA2022/050889 WO2022251968A1 (fr) 2021-06-03 2022-06-03 Matériaux d'enrobage à base d'hydrocarbures aliphatiques insaturés et leurs utilisations dans des applications électrochimiques

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