WO2023140276A1 - ポリイミドバインダ前駆体組成物、およびそれを用いた蓄電デバイス - Google Patents

ポリイミドバインダ前駆体組成物、およびそれを用いた蓄電デバイス Download PDF

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WO2023140276A1
WO2023140276A1 PCT/JP2023/001286 JP2023001286W WO2023140276A1 WO 2023140276 A1 WO2023140276 A1 WO 2023140276A1 JP 2023001286 W JP2023001286 W JP 2023001286W WO 2023140276 A1 WO2023140276 A1 WO 2023140276A1
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Prior art keywords
negative electrode
polyimide binder
precursor composition
polyimide
active material
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PCT/JP2023/001286
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English (en)
French (fr)
Japanese (ja)
Inventor
佳祐 森本
暢 飯泉
翔平 井上
壮輔 本間
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Ube Corp
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Ube Corp
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Priority to JP2023575268A priority Critical patent/JP7639950B2/ja
Priority to KR1020247027481A priority patent/KR102930019B1/ko
Priority to US18/729,291 priority patent/US20250112240A1/en
Priority to EP23743270.3A priority patent/EP4468418A4/en
Priority to CN202380026935.4A priority patent/CN118872096B/zh
Publication of WO2023140276A1 publication Critical patent/WO2023140276A1/ja
Anticipated expiration legal-status Critical
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    • H01M4/02—Electrodes composed of, or comprising, active material
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    • H01M4/622—Binders being polymers
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    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to a polyimide-based binder for an electric storage device such as a lithium ion secondary battery, and more particularly to a polyimide binder precursor composition, an electrode mixture paste, a negative electrode active material layer, a negative electrode sheet, and an electric storage device.
  • Electricity storage devices such as lithium-ion secondary batteries have high energy density and high capacity, so they are widely used as power sources for driving mobile information terminals.
  • industrial applications such as installation in electric/hybrid vehicles, unmanned aircraft, etc. have been studied, and further increases in the capacity of power storage devices such as lithium-ion secondary batteries are underway.
  • studies are underway to increase the charge/discharge capacity by using silicon, tin, or alloys containing these, which have a large amount of lithium absorption per unit volume, for the negative electrode.
  • electrode active materials with large charge/discharge capacities such as silicon, tin, and alloys containing these, undergo a very large volume change during charge/discharge. Therefore, when a negative electrode active material layer is formed with a general-purpose binder such as polyvinylidene fluoride or rubber-based resin using these electrode active materials, the negative electrode active material layer breaks due to the volume change of the electrode active material.
  • Patent Document 4 (US2006/0099506) points out that a large irreversible capacity is observed when a polyimide binder is used.
  • Patent Document 4 specifically, as a solution for reducing the irreversible capacity, in a polyimide binder obtained from 3,3'4,4'-benzophenonetetracarboxylic dianhydride and 4,4'-oxydianiline, part or all of the tetracarboxylic dianhydride is proposed to be replaced with 1,2,3,4-butanetetracarboxylic dianhydride, which is a chain aliphatic tetracarboxylic dianhydride.
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2019-38773 describes the use of a binder containing an imide group-containing polymer compound having a tensile elastic modulus of 3.0 GPa or more and a reactivity to lithium ions of 1200 mAh/g or less in a negative electrode active material layer containing a silicon-based negative electrode active material.
  • Patent Document 5 suggests that reactivity to lithium ions is related to cycle characteristics, but does not measure initial irreversible capacity. In order to correctly evaluate the effect on the initial efficiency, it is necessary to evaluate the charge/discharge capacity of the binder itself and grasp the irreversible capacity, which is the difference between them. In addition, there is almost no mention of the structure of polyimide, and the details cannot be grasped.
  • An object of the present invention is to solve the above problems, and to provide a polyimide binder having a small irreversible capacity and a precursor composition thereof. Moreover, by using the polyimide binder of the present invention, it is possible to provide an electric storage device such as a lithium ion secondary battery having high initial charge/discharge efficiency.
  • a polyimide binder precursor composition for a power storage device electrode comprising a reaction product of a tetracarboxylic acid component and a diamine component, and a solvent
  • a polyimide binder precursor composition, wherein the polyimide binder obtained from this polyimide binder precursor composition has an irreversible capacity of 1200 mAh/g or less.
  • polyimide binder precursor composition contains a reaction product of a tetracarboxylic acid component containing 50 mol% or more of an alicyclic tetracarboxylic dianhydride and a diamine component, and a solvent.
  • Polyimide binder precursor composition according to item 1.
  • a negative electrode mixture paste for an electricity storage device containing the polyimide binder precursor composition according to any one of the above items 1 to 3, and an active material containing a silicon-containing material and/or graphite.
  • An electricity storage device comprising the electricity storage device negative electrode according to item 5 above.
  • a step of casting or applying the negative electrode mixture paste according to item 4 above onto a current collector A method for producing a negative electrode for an electric storage device, comprising a step of heat-treating a layer of the applied negative electrode mixture paste to form a negative electrode active material layer.
  • a method for manufacturing an electricity storage device which includes the method for manufacturing the negative electrode of item 7 above as one step
  • the present invention it is possible to provide a polyimide binder having a small irreversible capacity and a precursor composition thereof. Moreover, by using the polyimide binder of the present invention, it is possible to provide an electric storage device such as a lithium ion secondary battery having high initial charge/discharge efficiency. If this polyimide binder is used as, for example, a negative electrode binder, the amount of active material on the positive electrode side that compensates for the irreversible capacity can be reduced, and as a result, a lightweight, high-capacity electricity storage device can be obtained.
  • FIG. 3 is a diagram of one aspect showing a method for calculating the irreversible capacity of the polyimide binder itself in the present invention.
  • the polyimide binder precursor composition of the present invention contains a reaction product of a tetracarboxylic acid component and a diamine component, and a solvent.
  • the reaction product of the tetracarboxylic acid component and the diamine component in the polyimide binder precursor composition is a polyimide precursor as described below.
  • the polyimide binder precursor composition of the present invention is heat-treated together with particles such as an active material, for example, to remove the solvent and, if necessary, undergo an imidation reaction to convert to a polyimide binder that binds particles such as an active material.
  • the "polyimide binder (of the present invention)" is a binder obtained from the polyimide binder precursor composition of the present invention, and is, for example, a substance that binds particles such as an active material in an electrode.
  • the polyimide binder obtained from the polyimide binder precursor composition of the present invention has an irreversible capacity of 1200 mAh/g or less.
  • the irreversible capacity is preferably 1100 mAh/g or less, more preferably 1000 mAh/g or less, even more preferably 900 mAh/g or less, still more preferably 800 mAh/g or less.
  • the irreversible capacity of a polyimide binder can be determined as follows. (1) A polyimide binder precursor composition and a negative electrode active material are mixed at different ratios to produce a plurality of mixture pastes for evaluation. Using the mixture paste for evaluation, a plurality of negative electrodes for evaluation with different content ratios of the polyimide binder are manufactured. (2) For example, using metallic lithium as a counter electrode, the initial charge capacity and initial discharge capacity of the evaluation negative electrode are measured, and the difference between the charge capacity (mAh/g) and discharge capacity (mAh/g) of the active material layer is defined as the irreversible capacity (mAh/g) of the evaluation negative electrode.
  • the charge capacity and discharge capacity per unit mass are calculated based on the total mass of the active material and the binder.
  • the irreversible capacity (mAh/g) of the negative electrode for evaluation is plotted against the content ratio (% by mass) of the polyimide binder to prepare a calibration curve.
  • the irreversible capacity of the evaluation negative electrode with a polyimide binder content of 100% is defined as "polyimide binder irreversible capacity”.
  • the negative electrode active material for manufacturing the negative electrode for evaluation does not need to be a silicon-based material, and it is preferable to use graphite with a smaller capacity than that.
  • metallic lithium is preferable in order to eliminate the influence of the irreversible capacity of the counter electrode.
  • the polyimide binder have excellent mechanical properties. Binders with excellent mechanical properties can withstand expansion and contraction due to charging and discharging even when a material such as a silicon-based material that causes a large volume change is used as an electrode active material.
  • the mechanical properties of polyimide binders can be measured using polyimide films formed from the polyimide binder precursor composition.
  • a typical mechanical property is the elastic modulus, which is preferably 1.0 GPa or higher, more preferably 2.0 GPa or higher, and even more preferably 2.5 GPa or higher.
  • the elongation percentage (elongation at break) is large, specifically preferably 30% or more, more preferably 40% or more, still more preferably 50% or more, still more preferably 60% or more, still more preferably 70% or more.
  • the breaking energy is preferably 40 MJ/m 3 or more, more preferably 50 MJ/m 3 or more, and even more preferably 60 MJ/m 3 or more.
  • all of the elastic modulus, elongation (elongation at break) and breaking energy satisfy the "preferred" ranges at the same time.
  • the tetracarboxylic acid component includes tetracarboxylic acid, tetracarboxylic dianhydride, and other tetracarboxylic acid derivatives such as tetracarboxylic acid silyl esters, tetracarboxylic acid esters, and tetracarboxylic acid chlorides used as raw materials for producing polyimides.
  • the diamine component is a diamine compound having two amino groups (--NH 2 ), which is used as a raw material for producing polyimide.
  • the reaction product of the tetracarboxylic acid component and the diamine component is usually called a polyimide precursor, and typically contains a polyamic acid (and its derivative) whose repeating unit is represented by the following general formula (I), but may have a structure with further imidization.
  • X 1 is derived from the tetracarboxylic acid component and Y 1 is derived from the diamine component.
  • X 1 is a tetravalent aliphatic or aromatic group
  • Y 1 is a divalent aliphatic or aromatic group
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkylsilyl group having 3 to 9 carbon atoms.
  • a repeating unit in which general formula (I) is further imidized is a structure in which one or two of the two amide bonds present in general formula (I) are converted to imide bonds.
  • the imidization rate is 0%, when all of the repeating units are of general formula (Ib) and/or (Ic), the imidization rate is 50%, and when all of the repeating units are of general formula (II), the imidization rate is 100% (that is, polyimide).
  • the imidization rate of the polyimide precursor may be in any range from 0 to 100%. In the present application, even if the imidization rate is 100%, what is present in the polyimide binder precursor composition is called a polyimide precursor.
  • a preferred form includes repeating units of formula (I), and may include repeating units selected from formulas (I), (Ib) and/or (Ic), and formula (II) so that the imidization rate is 0 to 50%, for example, 0 to 30%, and further 0 to 20%.
  • the repeating unit of formula (II) can be included, for example, repeating units selected from the above formulas such that the imidization rate is more than 50% to 100%.
  • An aliphatic tetracarboxylic dianhydride or an aromatic tetracarboxylic dianhydride is used as the tetracarboxylic acid component.
  • the aliphatic tetracarboxylic dianhydride is preferably an alicyclic tetracarboxylic dianhydride, for example, a tetracarboxylic dianhydride in which four carboxyl groups are directly bonded to the alicyclic group X1 .
  • the proportion of the alicyclic tetracarboxylic dianhydride in the total tetracarboxylic acid component is 50 mol% or more, more preferably 60 mol% or more, even more preferably 70 mol% or more, and even more preferably 80 mol% or more (including 100 mol%).
  • the remaining tetracarboxylic acid component is preferably an aromatic tetracarboxylic dianhydride.
  • the polyimide precursor When the polyimide precursor is obtained using a tetracarboxylic acid component containing an alicyclic tetracarboxylic dianhydride and other tetracarboxylic dianhydrides (preferably aromatic tetracarboxylic dianhydrides), it may be a copolymer, a block (co)polymer, a blend of homopolymers, or a blend of a copolymer and a homopolymer.
  • a copolymer has an alicyclic group X 1 and an aromatic group X 1 in one molecule.
  • a block (co)polymer is one in which a block consisting of repeating units of the alicyclic group X 1 reacts with a block consisting of repeating units of the aromatic group X 1 to form one molecule.
  • a homopolymer blend is a blend of a polymer having only an alicyclic group X 1 and a polymer having only an aromatic group X 1. .
  • the alicyclic group X 1 is preferably a tetravalent group having an alicyclic structure with 4 to 40 carbon atoms, and at least one aliphatic 4- to 12-membered ring, more preferably an aliphatic 4-membered ring or an aliphatic 6-membered ring.
  • Preferred tetravalent groups having an aliphatic 4-membered ring or an aliphatic 6-membered ring include the following.
  • R 31 to R 38 is an independent binding or dual organic group, respectively.
  • R 48 is an organic group that contains an aromatic or fat ring structure.
  • R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , and R 38 include a direct bond, an organic group containing an aromatic ring or an alicyclic structure, an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an oxygen atom (—O—), a sulfur atom (—S—), a carbonyl bond, an ester bond, and an amide bond.
  • organic groups containing aromatic rings as R 31 to R 38 or R 48 include the following.
  • W 1 is a direct bond or a divalent organic group
  • n 11 to n 13 each independently represent an integer of 0 to 4
  • R 51 , R 52 and R 53 each independently represent an alkyl group having 1 to 6 carbon atoms, a halogen group, a hydroxyl group, a carboxyl group or a trifluoromethyl group.
  • W 1 examples include a direct bond, a divalent group represented by the following formula (5), and a divalent group represented by the following formula (6).
  • R 61 to R 68 in formula (6) each independently represent either a direct bond or a divalent group represented by formula (5) above.
  • the alicyclic tetracarboxylic dianhydrides include, for example, monocyclic alicyclic tetracarboxylic dianhydrides such as 1,2,3,4-cyclobutanetetracarboxylic dianhydride and cyclohexane-1,2,4,5-tetracarboxylic dianhydride, [1,1'-bi(cyclohexane)]-3,3',4,4'-tetracarboxylic dianhydride, and [1,1'-bi(cyclohexane)]-2,3,3',4'-tetracarboxylic acid.
  • monocyclic alicyclic tetracarboxylic dianhydrides such as 1,2,3,4-cyclobutanetetracarboxylic dianhydride and cyclohexane-1,2,4,5-tetracarboxylic dianhydride, [1,1'-bi(cyclohexane)]-3,3',4,4'-t
  • the aromatic tetracarboxylic dianhydride preferably has 2-3 aromatic rings.
  • a compound having the following structure can be mentioned as the aromatic group X 1 .
  • Z1 is a direct bond or the following divalent group:
  • Z 2 in the formula is a divalent organic group
  • Z 3 and Z 4 are each independently an amide bond, an ester bond and a carbonyl bond
  • Z 5 is an organic group containing an aromatic ring.
  • Z 2 include aliphatic hydrocarbon groups having 2 to 24 carbon atoms and aromatic hydrocarbon groups having 6 to 24 carbon atoms.
  • Z 5 specifically includes an aromatic hydrocarbon group having 6 to 24 carbon atoms.
  • the aromatic tetracarboxylic dianhydride is not particularly limited, but includes 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, pyromellitic dianhydride, benzophenonetetracarboxylic dianhydride, 4,4'-oxydiphthalic dianhydride, diphenylsulfonetetracarboxylic dianhydride, p-ter Halogen-unsubstituted aromatic tetracarboxylic dianhydrides such as phenyltetracarboxylic dianhydride and m-terphenyltetracarboxylic dianhydride; 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 3,3'-(hexa
  • an aromatic diamine compound or an aliphatic diamine compound is used as the diamine component.
  • the proportion of the aromatic diamine compound in the total diamine component is 50 mol% or more, more preferably 60 mol% or more, still more preferably 70 mol% or more, still more preferably 80 mol% or more (including 100 mol%).
  • the remaining diamine component is an aliphatic diamine compound, preferably a diamine compound having an alicyclic structure.
  • the diamine component may contain an aliphatic diamine compound, preferably an alicyclic diamine compound, in a proportion of 50 mol% or more, more preferably 60 mol% or more, even more preferably 70 mol% or more, even more preferably 80 mol% or more (including 100 mol%) of the total diamine component.
  • examples of the aromatic group Y 1 include the following.
  • W 1 is a direct bond or a divalent organic group
  • n 11 to n 13 each independently represent an integer of 0 to 4
  • R 51 , R 52 and R 53 each independently represent an alkyl group having 1 to 6 carbon atoms, a halogen group, a hydroxyl group, a carboxyl group or a trifluoromethyl group.
  • W 1 examples include a direct bond, a divalent group represented by the following formula (5), and a divalent group represented by the following formula (6).
  • R 61 to R 68 in formula (6) each independently represent either a direct bond or a divalent group represented by formula (5) above.
  • preferred diamine compounds include 9,9-bis(4-aminophenyl)fluorene, 4,4′-(((9H-fluorene-9,9-diyl)bis([1,1′-biphenyl]-5,2-diyl))bis(oxy))diamine, [1,1′:4′,1′′-terphenyl]-4,4′′-diamine, 4,4′-([1,1′-binaphthalene]-2,2′-diamine, Irbis(oxy))diamines may be mentioned.
  • a diamine component may be used individually and can also be used in combination of multiple types.
  • examples of Y 1 which is a group having an alicyclic structure include the following.
  • V 1 and V 2 are each independently a direct bond or a divalent organic group
  • n 21 to n 26 each independently represent an integer of 0 to 4
  • R 81 to R 86 each independently represent an alkyl group having 1 to 6 carbon atoms, a halogen group, a hydroxyl group, a carboxyl group or a trifluoromethyl group
  • V 1 and V 2 include a direct bond and a divalent group represented by formula (5) above.
  • a diamine component may be used individually and can also be used in combination of multiple types.
  • Solvents include aromatic hydrocarbons such as xylene, toluene, and ethylbenzene; aliphatic hydrocarbons such as pentane, hexane, and heptane; nonpolar solvents (solvents having a dielectric constant of 6 or less) such as benzoic acid esters such as methyl benzoate, ethyl benzoate, and propyl benzoate; , N-ethyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-methylcaprolactam, hexamethylphosphorotriamide, 1,2-dimethoxymethane, bis(2-methoxyethyl)ether, 1,2-bis(2-methoxyethoxy)ethane, tetrahydrofuran, bis[2-(2-methoxyethoxy)ethyl]ether, 1,4-dioxane, dimethylsulfoxide, dimethylsulf
  • the polyimide binder precursor composition of the present invention is obtained by reacting a tetracarboxylic acid component and a diamine component in a reaction solvent.
  • the reaction solvent may be one of the solvents listed above, preferably the reaction solvent is contained as such in the polyimide binder precursor composition.
  • This reaction uses a tetracarboxylic acid component (tetracarboxylic dianhydride) and a diamine component in approximately equimolar amounts, and is carried out at a relatively low temperature of, for example, 25°C or higher and 100°C or lower, preferably 80°C or lower.
  • the reaction temperature is usually 25° C. to 100° C., preferably 25° C. to 80° C., more preferably 30° C. to 80° C.
  • the reaction time is, for example, about 0.1 to 72 hours, preferably about 2 to 60 hours.
  • the reaction can be carried out in an air atmosphere, it is usually carried out in an inert gas atmosphere, preferably in a nitrogen gas atmosphere.
  • the tetracarboxylic acid component tetracarboxylic dianhydride
  • the diamine component are approximately equimolar
  • the molar ratio [tetracarboxylic acid component/diamine component] is about 0.90 to 1.10, preferably about 0.95 to 1.05.
  • the solid content concentration of the polyimide binder precursor composition is preferably more than 5% by mass to 45% by mass, more preferably more than 10% by mass to 40% by mass, still more preferably more than 10% by mass to 30% by mass. If the solid content concentration is lower than 5% by mass, the viscosity of the composition becomes too low, and if it is higher than 45% by mass, the fluidity of the composition may be lost.
  • the reaction solution of the tetracarboxylic acid component and the diamine component may be used as it is as the polyimide binder precursor composition, or it may be concentrated or diluted as necessary to adjust the concentration.
  • the solution viscosity (viscosity of the polyimide binder precursor composition) at 30°C is preferably 1000 Pa ⁇ sec or less, more preferably 500 Pa ⁇ sec or less, still more preferably 300 Pa ⁇ sec or less, and particularly preferably 200 Pa ⁇ sec or less.
  • the solution viscosity is 1000 Pa ⁇ sec or less, mixing of the electrode active material powder and uniform coating on the current collector are facilitated, which is preferable.
  • the polyimide binder precursor composition may contain in advance additives other than the electrode active material, which will be explained in the following section ⁇ Electrode mixture paste>. Details will be described below by taking a lithium ion secondary battery as an example.
  • An electrode mixture paste which is one embodiment of the present invention, is a composition containing a polyimide binder precursor composition, an electrode active material, and a solvent added as necessary.
  • a known electrode active material can be suitably used in the electrode mixture paste of the present invention.
  • the polyimide binder precursor composition of the present invention can be used for both negative and positive electrodes. Therefore, the electrode active material may be either a negative electrode active material or a positive electrode active material. Generally, the effect of using the polyimide binder precursor composition of the present invention is greater for the negative electrode.
  • the electrode active material includes the negative electrode active material.
  • Preferred examples of the electrode active material include lithium-containing metal composite oxides, carbon powder, silicon powder, tin powder, and alloy powders containing silicon or tin.
  • the amount of the electrode active material in the electrode mixture paste is not particularly limited, and may be appropriately determined according to the desired capacity.
  • the amount of the electrode active material is preferably 0.1 times or more, more preferably 1 time or more, even more preferably 5 times or more, and still more preferably 10 times or more, based on the mass of the solid content (polyimide equivalent mass) in the polyimide binder precursor composition. Within these ranges, the active portion in the negative electrode active material layer increases, so that the electrode can be sufficiently functioned. On the other hand, in order to sufficiently bind the electrode active material to the current collector and effectively prevent it from coming off, the amount of the electrode active material is preferably 1000 times or less of the solid content in the polyimide binder precursor composition.
  • Examples of negative electrode active materials for lithium ion secondary batteries include lithium metals, lithium alloys, and carbon materials capable of intercalating and deintercalating lithium [graphitizable carbon, non-graphitizable carbon having a (002) plane spacing of 0.37 nm or more, graphite having a (002) plane spacing of 0.34 nm or less, etc.], tin (elementary substance), tin compounds, silicon (elemental substance), silicon compounds, lithium titanate compounds such as Li 4 Ti 5 O 12 , and the like. can be used singly or in combination of two or more.
  • the negative electrode active material preferably contains at least tin (single substance), a tin compound, silicon (single substance), or a silicon-containing substance such as a silicon compound (in the following description, may be referred to as a silicon-containing negative electrode active material or a silicon-containing active material).
  • silicon (single substance) or a silicon-containing substance such as a silicon compound has a much larger theoretical capacity than graphite, but the volume expansion coefficient of the electrode active material itself during charging is also very large.
  • a lithium ion secondary battery using the polyimide binder precursor composition of the present invention suppresses deterioration of the electrode active material due to volume expansion, and is excellent not only in cycle characteristics during use, but also in low temperature characteristics after high temperature storage and characteristics in a wide temperature range such as gas generation.
  • silicon-containing active material is not particularly limited, but examples include silicon (single substance), silicon compounds, partially substituted silicon, partially substituted silicon compounds, and solid solutions of silicon compounds.
  • silicon compounds preferably include silicon oxides represented by SiOx (0.05 ⁇ x ⁇ 1.95), silicon carbides represented by the formula: SiCy (0 ⁇ y ⁇ 1), silicon nitrides represented by the formula: SiNz (0 ⁇ z ⁇ 4/3), and silicon alloys that are alloys of silicon and a different element M.
  • the dissimilar element M1 is preferably at least one element selected from the group consisting of Fe, Co, Sb, Bi, Pb, Ni, Cu, Zn, Ge, In, Sn and Ti.
  • the partially substituted silicon is a compound obtained by substituting part of the silicon contained in silicon (single element) and silicon compound with the heterogeneous element M2.
  • the dissimilar element M2 preferably include B, Mg, Ni, Ti, Mo, Co, Ca, Cr, Cu, Fe, Mn, Nb, Ta, V, W, Zn, C, N and Sn.
  • silicon-containing substances silicon (elementary substance), silicon oxide, or silicon alloy is preferable, and silicon (elemental substance) or silicon oxide is more preferable.
  • the amount of the silicon-containing active material, as the net mass of silicon in the negative electrode mixture, is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, and from the viewpoint of improving cycle characteristics, is preferably 95% by mass or less, more preferably 65% by mass or less, and even more preferably 45% by mass or less.
  • Solvents that can be used in the electrode mixture paste include aromatic hydrocarbons such as xylene, toluene, and ethylbenzene; aliphatic hydrocarbons such as pentane, hexane, and heptane; nonpolar solvents such as methyl benzoate, ethyl benzoate, and benzoate esters such as propyl benzoate; -ethyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N-methylcaprolactam, hexamethylphosphorotriamide, 1,2-dimethoxymethane, bis(2-methoxyethyl)ether, 1,2-bis(2-methoxyethoxy)ethane, tetrahydrofuran, bis[2-(2-methoxyethoxy)ethyl]ether, 1,4-dioxane, dimethylsulfoxide, dimethylsulfone, diphenylether, sulfolane
  • the solvent in the polyimide binder precursor composition can be used as it is, it can be concentrated as necessary, or an additional solvent can be added to obtain a suitable concentration for coating.
  • the electrode mixture paste of the present invention When the electrode mixture paste of the present invention is made into a water solvent system, it preferably contains a pyridine compound and an imidazole compound. As a result, the degree of swelling of the obtained polyimide with respect to the electrolytic solution can be made smaller, and the elongation (elongation at break) and breaking energy can be made larger. In addition, the heat treatment temperature for obtaining the negative electrode active material layer can be kept low.
  • a pyridine-class compound is a compound having a pyridine skeleton in its chemical structure, and suitable examples thereof include pyridine, 3-pyridinol, quinoline, isoquinoline, quinoxaline, 6-tert-butylquinoline, acridine, 6-quinolinecarboxylic acid, 3,4-lutidine, and pyridazine. These pyridine compounds may be used singly or in combination of two or more.
  • Examples of imidazole compounds include 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 4-ethyl-2-methylimidazole, 1-methyl-4-ethylimidazole and the like.
  • the imidazoles to be used may be one kind or a mixture of two or more kinds.
  • the amount of the pyridine compound compounded is not limited, it is preferably 0.05 to 2.0 molar equivalents, more preferably 0.1 to 1.0 molar equivalents, relative to 1 mol of repeating units of the polyimide precursor (especially polyamic acid). If the amount added is out of this range, it may be difficult to use an aqueous solvent system.
  • the blending amount of the imidazole compound is not limited, but is 1.6 molar equivalents or more, more preferably 2.0 molar equivalents or more, and still more preferably 2.4 molar equivalents or more with respect to 1 mol of the amic acid repeating unit of the polyamic acid.
  • additives can be added to the electrode mixture paste of the present invention, if necessary.
  • negative electrode conductive agents, bases, surfactants, viscosity modifiers, conductive aids, silane coupling agents, binders other than polyimides, and the like can be used as long as the effects of the present invention are not impaired.
  • the negative electrode conductor is not particularly limited as long as it is an electronically conductive material that does not cause a chemical change, but it is preferable to use a metal powder such as copper, nickel, titanium, or aluminum, or a carbon material.
  • a metal powder such as copper, nickel, titanium, or aluminum, or a carbon material.
  • the carbon material used as a conductive agent or a negative electrode active material include graphite such as natural graphite (flaky graphite, etc.) and artificial graphite; one or more types of carbon black selected from acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black; and fibrous carbon powder such as carbon nanotubes and carbon fibers.
  • the negative electrode conductor it is more preferable to appropriately mix and use graphite and carbon black, graphite and fibrous carbon powder, or carbon black and fibrous carbon powder.
  • the use of fibrous carbon powder is preferable because it has the effect of reducing the use of a conductive agent having a large specific surface area in order to ensure conductivity.
  • a carbon material is used as a conductive agent or a negative electrode active material, and the amount of the carbon material added to the negative electrode mixture is preferably 1 to 90% by mass, more preferably 10 to 70% by mass.
  • the ratio of the silicon-containing negative electrode active material and the carbon material is preferably 10% by mass or more, more preferably 20% by mass or more, based on the total mass of silicon in the silicon-containing negative electrode active material in the negative electrode mixture, from the viewpoint of cycle improvement based on the effect of improving electronic conductivity by mixing with the carbon material.
  • the ratio of the carbon material mixed with the silicon-containing negative electrode active material is too large, the amount of the silicon-containing negative electrode active material in the negative electrode mixture layer may decrease, and the effect of increasing the capacity may be reduced.
  • the conductive agent is compounded by being premixed with the silicon-containing active material and appropriately heat-treated.
  • a carbon material having a graphite-type crystal structure in which the interplanar spacing (d002) of the graphite lattice plane (002) is 0.340 nm (nanometers) or less, particularly 0.335 to 0.337 nm.
  • artificial graphite particles having a massive structure in which a plurality of flat graphite fine particles are aggregated or bonded non-parallel to each other, and particles obtained by repeatedly applying mechanical actions such as compressive force, frictional force, and shearing force to spheroidize natural graphite flakes.
  • the ratio I(110)/I(004) of the peak intensity I(110) of the (110) plane and the peak intensity I(004) of the (004) plane of the graphite crystal obtained from the X-ray diffraction measurement of the negative electrode sheet when the density of the portion of the negative electrode excluding the current collector is 1.5 g/cm 3 or more is 0.01 or more, the electrochemical characteristics are further improved over a wider temperature range, so the ratio I(110)/I(004) is preferably 0.05 or more. Preferably, it is more preferably 0.1 or more. Also, excessive treatment may lower the crystallinity and reduce the discharge capacity of the battery. Therefore, the upper limit of the peak intensity ratio I(110)/I(004) is preferably 0.5 or less, more preferably 0.3 or less.
  • the highly crystalline carbon material (core material) is coated with a less crystalline carbon material than the core material, because the electrochemical properties are further improved over a wide temperature range.
  • the crystallinity of the carbon material of the coating can be confirmed by TEM.
  • a highly crystalline carbon material it reacts with the nonaqueous electrolyte during charging, and the increase in interfacial resistance tends to reduce the characteristics of the lithium ion secondary battery in a wide temperature range such as low temperature characteristics and gas generation after high temperature storage.
  • the polyimide binder precursor composition according to the present invention is used, the characteristics of the lithium ion secondary battery are improved.
  • the polyimide binder precursor composition of the present invention is used for the negative electrode mixture paste.
  • Other binders can also be used together in an amount of 95% by mass or less, preferably 45% by mass or less.
  • binders other than the polyimide binder precursor composition of the present invention include polyvinylidene fluoride, polytetrafluoroethylene, styrene-butadiene rubber, butadiene rubber, nitrile rubber, polyacrylonitrile, ethylene-vinyl alcohol copolymer resin, ethylene-propylene diene rubber, polyurethane, polyacrylic acid, polyamide, polyacrylate, polyvinyl ether, fluororubber, carboxymethylcellulose, and sodium carboxymethylcellulose.
  • the electrode mixture paste of the present invention may further contain a solid electrolyte.
  • solid electrolytes include perovskite-type crystal La 0.51 Li 0.34 TiO 2.94 , garnet-type crystal Li 7 La 3 Zr 2 O 12 , NASICON-type crystal Li 1.3 Al 0.3 Ti 1.7 (PO 4 ) 3 , amorphous LIPON (Li 2.9 PO 3.3 N 0.46 ), and sulfide solid electrolytes such as Li 2 S—SiS 2 system and Li 2 SP 2 S 5 system.
  • the electrode mixture paste of the present invention can be produced as a uniform composition by applying a known production method to the components described above and adding, stirring, mixing, and the like.
  • an electrode mixture paste may be produced by adding and mixing various additives after producing a solution or dispersion liquid in which a polyimide binder and a solvent are mixed.
  • a negative electrode (negative electrode sheet) having a negative electrode active material layer on a current collector can be formed by casting or coating the negative electrode mixture paste of the present invention on a conductive current collector, followed by casting or coating, heat treatment to remove the solvent, and, if necessary, imidation reaction. During the process of forming the negative electrode sheet, it is also preferable to perform pressing using a roll press until the target electrode density is achieved.
  • a known current collector can be used.
  • the polyimide precursor present in the polyimide binder precursor composition is converted to a polyimide binder by heat treatment, and binds particles such as the active material and conductive agent to each other and to the current collector at the same time.
  • the heat treatment removes the solvent, promotes imidization of the polyimide precursor, and lowers the solubility in solvents such as electrolytic solutions, thereby improving the solvent resistance.
  • the heat treatment can be performed, for example, at 80°C to 450°C.
  • the step of mainly removing the solvent and the step of mainly proceeding with imidization may be divided into step 1 of heating at 80° C. to 200° C. (or 180° C.) and step 2 of heating at a temperature of 200° C. or higher (or 180° C. or higher), and the heat treatment may be performed stepwise or continuously.
  • imidization may proceed on the high temperature side of step 1, and desolvation also occurs in step 2 depending on the degree of solvent removal in step 1.
  • the time for steps 1 and 2 can be determined as appropriate in consideration of the simplicity of the process and the desired imidization rate.
  • the time of step 1 may be 0 seconds (without step 1), but is preferably 1 minute or more, more preferably 10 minutes or more, and preferably 5 hours or less, more preferably 2 hours or less, while the time of step 2 is preferably 10 minutes or more, more preferably 30 minutes or more, and preferably 24 hours or less, more preferably 12 hours or less.
  • the imidization rate of the polyimide precursor present in the polyimide binder precursor composition is high, for example, the imidization rate is 70% or more, preferably 80% or more (90% or more, or 100%), only the above step 1, which mainly removes the solvent, may be sufficient as the heat treatment. However, in order to ensure solvent removal and/or to increase the imidization rate, step 2 above may also be carried out.
  • the thickness of the negative electrode active material layer of the present invention may be appropriately determined according to the application and desired capacity. Although not limited, it is preferably used in the range of, for example, 0.1 ⁇ m to 500 ⁇ m. More preferably 1 ⁇ m or more, still more preferably 10 ⁇ m or more, still more preferably 20 ⁇ m or more, more preferably 300 ⁇ m or less, still more preferably 100 ⁇ m or less, still more preferably 50 ⁇ m or less.
  • a positive electrode active material for a lithium secondary battery a composite metal oxide with lithium containing one or more selected from cobalt, manganese and nickel is used. These positive electrode active materials can be used individually by 1 type or in combination of 2 or more types. Examples of such lithium composite metal oxides include LiCoO 2 , LiMn 2 O 4 , LiNiO 2 , LiCo 1-x Ni x O 2 (0.01 ⁇ x ⁇ 1), LiCo 1/3 Ni 1/3 Mn 1/3 O 2 , LiNi 1/2 Mn 3/2 O 4 , and LiCo 0.98 Mg 0.02 One or more selected from O 2 can be mentioned. Moreover, you may use together like LiCoO2 and LiMn2O4 , LiCoO2 and LiNiO2 , LiMn2O4 and LiNiO2 .
  • a part of the lithium composite metal oxide may be replaced with other elements.
  • part of cobalt, manganese, and nickel can be replaced with at least one or more elements such as Sn, Mg, Fe, Ti, Al, Zr, Cr, V, Ga, Zn, Cu, Bi, Mo, La, or part of O can be replaced with S or F, or a compound containing these other elements can be coated.
  • a lithium-containing olivine-type phosphate can also be used as the positive electrode active material.
  • Lithium-containing olivine-type phosphate containing at least one selected from iron, cobalt, nickel and manganese is particularly preferable.
  • one or more selected from LiFePO 4 , LiCoPO 4 , LiNiPO 4 , and LiMnPO 4 can be preferably mentioned.
  • lithium-containing olivine-type phosphates may be substituted with other elements, and a portion of iron, cobalt, nickel, and manganese may be substituted with one or more elements selected from Co, Mn, Ni, Mg, Al, B, Ti, V, Nb, Cu, Zn, Mo, Ca, Sr, W, and Zr, or may be coated with a compound or carbon material containing these other elements.
  • LiFePO4 or LiMnPO4 is preferred.
  • the lithium-containing olivine-type phosphate can be used, for example, by being mixed with the positive electrode active material.
  • the conductive agent for the positive electrode is not particularly limited as long as it is an electron conductive material that does not cause chemical changes.
  • natural graphite flaky graphite, etc.
  • graphite such as artificial graphite
  • one or more carbon blacks selected from acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black
  • carbon nanotubes fibrous carbon powders such as carbon fibers
  • it is more preferable to use a suitable mixture such as graphite and carbon black, graphite and fibrous carbon powder, or carbon black and fibrous carbon powder.
  • the amount of the conductive agent added to the positive electrode mixture is preferably 1 to 10% by mass, particularly preferably 2 to 5% by mass.
  • ⁇ Positive electrode binder> The polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), styrene and butadiene copolymer (SBR), acrylonitrile and butadiene copolymer (NBR), carboxymethyl cellulose (CMC), or ethylene propylene diene terpolymer can also be used as other binders.
  • PTFE polytetrafluoroethylene
  • PVDF polyvinylidene fluoride
  • SBR styrene and butadiene copolymer
  • NBR acrylonitrile and butadiene copolymer
  • CMC carboxymethyl cellulose
  • ethylene propylene diene terpolymer ethylene propylene diene terpolymer
  • the polyimide binder precursor composition of the present invention and other binders can be used in combination, and preferred embodiments in this case are the same as those described in [Negative electrode bin
  • the positive electrode sheet is obtained by casting or coating an electrode mixture paste, which is a mixture of optional components such as a positive electrode binder, a positive electrode active material, and optionally a conductive agent, on a current collector to form an active material layer.
  • an electrode mixture paste which is a mixture of optional components such as a positive electrode binder, a positive electrode active material, and optionally a conductive agent, on a current collector to form an active material layer.
  • a lithium-ion secondary battery which is one of the embodiments of the present invention, includes the negative electrode (negative electrode sheet) described above, and the positive electrode (positive electrode sheet), the electrolyte solution, and other necessary configurations such as a separator can adopt a known configuration necessary for a lithium-ion secondary battery.
  • the lithium ion secondary battery may be a lithium polymer battery using a gel electrolyte as an electrolyte, or an all-solid battery using an inorganic solid electrolyte such as an oxide-based or sulfide-based electrolyte.
  • the polyimide binder of the present invention can be used not only for lithium ion secondary batteries but also for other electric storage devices having a mechanism similar to that of lithium ion secondary batteries, such as lithium ion capacitors.
  • ODA 4,4′-diaminodiphenyl ether
  • PPD p-phenylenediamine
  • TPE-R 1,3-bis(4-aminophenoxy)benzene
  • BAPP 2,2-bis[4-(4-aminophenoxy)phenyl]propane
  • MBAA bis(4-amino-3-carboxyphenyl)methane
  • DABAN 4,4′-diaminobenzanilide
  • DATP 4,4′′-diamino-p-terphenyl
  • a negative electrode mixture paste was prepared by blending graphite (MAG-D; massive artificial graphite, manufactured by Showa Denko Materials Co., Ltd., average particle size 20 ⁇ m) as a negative electrode active material and a polyimide binder precursor composition (Example/Comparative Example) so that the solid content ratio was 92: 8, 95: 5, and 97: 3 (% by mass), and NMP was added and mixed so that the slurry concentration was about 50% by mass.
  • graphite MAG-D; massive artificial graphite, manufactured by Showa Denko Materials Co., Ltd., average particle size 20 ⁇ m
  • a polyimide binder precursor composition Example/Comparative Example
  • the negative electrode mixture paste was applied onto a nickel-plated steel foil (thickness: 10 ⁇ m) as a current collector, and pre-dried on a hot plate at 110° C. for 3 minutes. After that, it was roll-pressed, placed in an electric heating furnace, and heat-treated at 360° C. for 1.5 hours under an argon flow to prepare a negative electrode for evaluation (2 mAh/cm 2 ).
  • a negative electrode mixture paste was prepared by mixing silicon as a negative electrode active material (average particle size 3 ⁇ m manufactured by Elkem), a polyimide binder precursor composition (Examples and Comparative Examples), and a conductive aid (acetylene black manufactured by DENKA) at a solid content ratio of 60:30:10 (% by mass).
  • the negative electrode mixture paste was applied onto a nickel-plated steel foil (thickness: 10 ⁇ m) as a current collector, and pre-dried at 110° C. for 3 minutes. After that, it was roll-pressed, placed in an electric heating furnace, and heat-treated at 360° C. for 1.5 hours under an argon flow to prepare a negative electrode (3 mAh/cm 2 ).
  • a polyimide binder precursor composition (Examples/Comparative Examples) was applied onto a glass substrate using a spin coater, dried at 80°C for 10 minutes, and then heat-treated in a nitrogen atmosphere at 120°C for 30 minutes, 150°C for 10 minutes, 200°C for 10 minutes, 250°C for 10 minutes, and 350°C for 10 minutes (heating rate: 5°C/min) to obtain a 10 ⁇ m thick film.
  • a test sample was prepared by cutting the obtained film into a strip having a width of 10 mm and a length of 200 mm.
  • the test sample was set in a tensile tester with a chuck-to-chuck distance of 100 mm, the sample was pulled at a speed of 50 mm/min, and the resulting stress-strain curve was used to calculate the elastic modulus, elongation (elongation at break), and breaking energy.
  • the measurement environment is room temperature in the atmosphere.
  • composition PI-1 160 g of NMP was added to the reactor, and the temperature in the reactor was adjusted to 50° C. while the inside of the reactor was replaced with nitrogen. After adding 23.5916 g of ODA and dissolving it, H′′-PMDA was added in stages with a total of 26.3424 g (molar ratio to diamine: 1) and 40 g of NMP, and stirred overnight at 50° C. to obtain a polyimide binder precursor composition PI-1. Viscosity 49P
  • compositions PI-2 to PI-12 [Compositions PI-2 to PI-12]
  • the tetracarboxylic dianhydrides and diamines shown in Table 2 were reacted in the same manner as composition PI-1 to obtain polyimide binder precursor compositions PI-2 to PI-12. Viscosities and concentrations are shown in Table 2.
  • composition PI-10′ polyimide solution type composition
  • a polyimide solution-type polyimide binder precursor composition was produced by proceeding with imidization from the same monomer composition as composition PI-10. First, 160 g of NMP was added to a reaction vessel, and the temperature in the vessel was adjusted to 50° C. while the inside of the vessel was replaced with nitrogen. After 32.3399 g of BAPP was added and dissolved therein, the temperature of the reaction bath was raised to 70° C., and a total of 17.6601 g of H′′-PMDA (molar ratio to diamine: 1) was added in stages along with 40 g of NMP. After stirring at 70° C. for 30 minutes, imidization was performed by stirring at 170° C. for 3 hours to obtain a polyimide binder precursor composition PI-10′. The viscosities and concentrations are shown in Table 2.
  • compositions PI-13 to PI-14 (copolymerized polyimide precursor) Using two types of tetracarboxylic acid dianhydrides shown in Table 2 as tetracarboxylic acid components, similarly using diamines shown in Table 2, polyimide binder precursor compositions PI-13 and PI-14 were obtained by reacting in the same manner as composition PI-1. Viscosities and concentrations are shown in Table 2. For compositions using two or more compounds as the tetracarboxylic acid component and the diamine component, the molar ratio is shown in parentheses after the monomers.
  • compositions PI-15 to PI-18 The tetracarboxylic dianhydrides and diamines shown in Table 2 were reacted in the same manner as composition PI-1 to obtain polyimide binder precursor compositions PI-15 to PI-18.
  • composition PI-MIX polyimide precursor blend
  • Table 2 two types of polyimide binder precursor compositions were blended to obtain a polyimide binder precursor composition PI-MIX. Viscosities and concentrations are shown in Table 2. In Table 2, the mixing ratio is shown in parentheses as a molar ratio (ratio of total number of monomer units).
  • compositions PI-19 to PI-23 [Compositions PI-19 to PI-23]
  • the tetracarboxylic dianhydrides and diamines shown in Table 2 were reacted in the same manner as composition PI-1 to obtain polyimide binder precursor compositions PI-19 to PI-23. Viscosities and concentrations are shown in Table 2.
  • the present invention can be suitably applied as an electrode binder for power storage devices such as lithium ion secondary batteries.

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PCT/JP2023/001286 2022-01-21 2023-01-18 ポリイミドバインダ前駆体組成物、およびそれを用いた蓄電デバイス Ceased WO2023140276A1 (ja)

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