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KR-20260066124-A - Electrode composition

KR20260066124AKR 20260066124 AKR20260066124 AKR 20260066124AKR-20260066124-A

Abstract

Compositions suitable for electrochemical devices are illustrated and described herein. The composition comprises an organic-functional material having a nitrogen functional group. In one aspect, the nitrogen functional group is a urethane functional group. The composition may be employed as an electrode material in an electrochemical cell, for example, a lithium battery.

Inventors

  • 빈두마드하반 카르틱
  • 시바수브라마니안 카르티케얀
  • 청 디아오
  • 푸칸 몬지트

Assignees

  • 모멘티브 퍼포먼스 머티리얼즈 인크.

Dates

Publication Date
20260512
Application Date
20240910
Priority Date
20230911

Claims (20)

  1. (a) Polymer resin; (b) Compound represented by formula (I); (c) electrode active agent; and (d) A composition comprising optionally a binder: Herein, R1 ', R2 ', R3 ', R4 ', R5 ', and R6 ' are independently selected from the group consisting of R4 , OR5 , and ureido functional groups, wherein R4 is independently selected from a monovalent group selected from the group consisting of straight-chain alkyl having 1 to 12 carbon atoms, branched-chain alkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, and aralkyl having 7 to 20 carbon atoms; R5 is independently selected from a monovalent group selected from the group consisting of straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; a' or b' is 0-500, provided that at least one of a' or b' is >0; and at least one of R1 ', R2 ', R3 ', R4 ', R5 ', and/or R6 ' is a ureidofunctional group; Here, the above ureido functional group is represented by the following formula: Here, R1 and R2 are each independently selected from the group consisting of hydrogen and a monovalent organic group having 1 to 20 carbon atoms; R3 is a divalent straight-chain alkylene group having 1 to 20 carbon atoms or a divalent branched alkylene group having 3 to 20 carbon atoms, each of which may optionally contain one or more heteroatoms in the chain; X is selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms and a heterocyclic group containing 1 to 20 heteroatoms, wherein the aromatic group and/or the heterocyclic group may optionally be substituted with an alkyl group having 1 to 12 carbon atoms and a ureido functional group optionally containing a heteroatom selected from the group consisting of O, N and/or S; and Z is oxygen.
  2. In claim 1, The above polymeric resins are polyethylene, polypropylene, polyethylene terephthalate, polymethyl methacrylate, aromatic polyamide, chitosan, alginic acid, polyacrylic acid, polyimide, cellulose, carboxymethyl cellulose, nitrocellulose; styrene-butadiene rubber (SBR), isoprene rubber, butadiene rubber, fluoroelastomer, acrylonitrile-butadiene rubber (NBR), ethylene-propylene rubber; styrene-butadiene-styrene block copolymer and its hydrogenation product; EPDM (ethylene-propylene-diene terpolymer), styrene-ethylene-butadiene-styrene copolymer, styrene-isoprene-styrene block copolymer and its hydrogenation product; syndiotactic-1,2-polybutadiene, polyvinyl acetate, ethylene-vinyl acetate copolymer, and propylene-α-olefin copolymer; A composition selected from one or more of the group consisting of polyvinylidene fluoride, polytetrafluoroethylene, vinylidene fluoride copolymer, and tetrafluoroethylene-ethylene copolymer; and a polymer comprising alkali metal ions.
  3. In claim 1 or claim 2, The above optional binder is a composition selected from one or more of the group consisting of carboxymethyl cellulose, methyl cellulose, hydroxymethyl cellulose, ethyl cellulose, polyvinyl alcohol, oxidized starch, monostarch phosphate, casein, polyvinylpyrrolidone, and salts thereof.
  4. In any one of claims 1 to 3, The above electrode active agent is a composition selected from the group consisting of one or more of an insert and a conductive agent.
  5. In claim 4, The above-mentioned insert is a composition selected from the group consisting of graphite, lithium nickel manganese cobalt oxide (LiNMC), Si, SiB₄ , SiB₆ , Mg₂Si , Ni₂Si, TiSi₂ , MoSi₂ , CoSi₂ , NiSi₂ , CaSi₂ , CrSi₂ , Cu₆Si , FeSi₂ , MnSi₂ , NbSi₂ , TaSi₂ , VSi₂ , WSi₂ , ZnSi₂ , SiC , Si₃N₄ , Si₂N₂O , SiO₂v ( 0 < v ≤ 2), LiSiO₂, Sn , SnSiO₃, LiSnO, and Mg₂Sn , SnO₂w (0 < w ≤ 2).
  6. In claim 4 or claim 5, The composition is a carbonaceous conductive agent selected from the group consisting of natural graphite, graphite including artificial graphite, carbon black including acetylene black, Ketjen black, channel black, furnace black, lamp black, and thermal black, amorphous carbon including needle coke, carbon nanotubes, fullerenes, and vapor-grown carbon fibers (VGCF).
  7. In any one of claims 1 to 6, A composition in which if a'>0, b'=0, and the compound represented by Formula 1 is a polysilane.
  8. In claim 7, The compound of formula (I) is a composition having the following formula: 1. Herein, R1 ', R3 ', R5 ', and R6 ' are each independently selected from R4 , OR5 , and ureido functional groups, wherein R4 is independently selected from monovalent groups selected from straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; R5 is independently selected from monovalent groups selected from straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; a' is 1-500 and; and At least one of R1 ', R3 ', R5 ', and R6 ' is selected from ureido functional groups.
  9. In any one of claims 1 to 6, A composition in which if b'>0, a'=0, and the compound represented by Formula 1 is a polysiloxane.
  10. In any one of claims 1 to 9, A composition in which the compound represented by Formula 1 is a uroidofunctional organosilicon.
  11. In any one of claims 1 to 10, The above ureido functional organosilicon is a composition in which the above ureido functional organosilicon is a compound of the following formula: Here, R1 and R2 are each independently hydrogen or a monovalent organic group having 1 to 20 carbon atoms; R3 is a divalent straight-chain alkylene group having 1 to 20 carbon atoms or a divalent branched alkylene group having 3 to 20 carbon atoms, each of which optionally contains one or more heteroatoms within the chain; R4 is independently a monovalent group selected from the group consisting of straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; R5 is independently selected from the group consisting of straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; X is an aromatic group having 6 to 20 carbon atoms or a heterocyclic group containing up to 20 heteroatoms, wherein the aromatic group or the heterocyclic group is optionally substituted with an alkyl group having 1 to 12 carbon atoms optionally containing a heteroatom selected from the group consisting of O, N and/or S, and a ureido functional group; Z is oxygen; and a is an integer with a value of 1, 2, or 3.
  12. In any one of claims 1 to 6 or claim 9, Composition in which the compound of formula (I) is a polysiloxane represented by the following formula: M 1 a M 2 b D 1 c D 2 d T 1 e T 2 f Q g Here, M 1 is (R 16 )(R 17 )(R 18 )SiO 1/2 and; M 2 is (R 19 )(R 20 )(R 21 )SiO 1/2 and; D1 is ( R22 )( R23 )SiO2 /2 and; D2 is ( R24 )( R25 )SiO2 /2 and; T1 is ( R26 )SiO3 /2 and; T2 is ( R27 )SiO3 /2 and; Q is SiO 4/2 and; R 16 , R 17 , R 18 , R 22 , R 23 , and R 26 are independently selected from the group consisting of R 4 and OR 5 ; R19 , R20 , R21 , R24 , R25 , and R27 are independently selected from the group consisting of R4 , OR5 , and ureido functional groups, provided that at least one of R19 , R20 , R21 , R24 , R25 , and R27 is a ureido functional group; Here, R4 is independently selected from the group consisting of monovalent groups selected from straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; R5 is independently selected from the group consisting of straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; b, d, and f are independently integers greater than 0; and a, c, e, and g are each independently greater than 0 integers.
  13. In any one of claims 1 to 12, X is a composition that is a six-membered ring containing up to five nitrogen atoms.
  14. In any one of claims 1 to 12, A composition in which X is a six-membered ring containing one or two nitrogen atoms.
  15. In any one of claims 1 to 12, X is a composition selected from the following: ; ; ; and Here, R 11 is selected from the group consisting of hydrogen and a monovalent organic group having 1 to 12 carbon atoms.
  16. In any one of claims 1 to 12, X is Phosphorus, composition: Here, J1 , J2 , and J3 are each independently substituted or unsubstituted C or N atoms, and The dotted line between J1 , J2 , and J3 represents an arbitrary double combination between J1 and J2 or between J2 and J3 .
  17. In any one of claims 1 to 12, Composition in which the substituents in X are represented by the following formula: Here, R6 and R7 are each independently hydrogen or a monovalent organic group having 1 to 20 carbon atoms; R8 is a divalent straight-chain alkylene group having 1 to 20 carbon atoms or a divalent branched alkylene group having 3 to 20 carbon atoms, each of which may optionally contain one or more heteroatoms within the chain; R9 is each independently selected from the group consisting of monovalent groups selected from straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; R 10 is independently selected from monovalent groups selected from straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; and b is an integer with a value of 1, 2, or 3.
  18. In claim 17, The above-mentioned ureidofunctional organosilicon is a composition represented by the following formula: .
  19. In any one of claims 1 to 18, A composition in which the compound represented by Formula 1 is present in an amount of about 0.1 to 10 weight percent based on the total weight of the composition.
  20. In any one of claims 1 to 18, A composition in which the compound of Formula 1 is present in an amount of about 0.01 wt% to about 90 wt%, about 0.05 wt% to about 80 wt%, about 0.1 wt% to about 75 wt%, about 0.2 wt% to about 60 wt%, about 0.5 wt% to about 50 wt%, about 1 wt% to about 25 wt%, or about 5 wt% to about 10 wt% based on the total weight of the composition; preferably, in an amount of 1-10 wt%, 10-50 wt%, or 50-90 wt% based on the total weight of the composition.

Description

Electrode composition The present invention relates to a composition for electrodes. In particular, the present invention relates to a composition comprising a uroidofunctional compound as an additive and a composition suitable for forming electrodes. As the use of batteries increases in various applications, such as electric vehicles and consumer electronics, the demand for the development and improvement of energy generation and energy storage devices continues to rise. Manufacturers are seeking to provide improved battery characteristics, such as high capacity, fast charging, long range, and long shelf life. These characteristics are directly influenced by the electrochemical reactions occurring within the battery. Graphite is a common material for cathode materials. Graphite has an irreversible capacity of 372 mAh g-1. This limited capacity may hinder its application in next-generation high-capacity batteries for long-term use on a single charge. Lithium batteries are a subject of great interest and use in industry. One way to improve the capacity of lithium batteries is to develop or introduce composites of high-capacity materials and graphite. Potential cathode materials include oxides, carbides, and/or nitrides of tin, germanium, and/or silicon. Silicon and silicon-based anode materials are of particular interest due to their high specific capacity. These materials are also generally readily available in large quantities. Silicon can exhibit a capacity of up to 3,700 mAh g-1. Silicon monoxide can provide a capacity of approximately 1,850 mAh g-1. However, silicon materials exhibit high expansion characteristics during lithiation. Silicon can expand by up to 400% in volume compared to its initial dimensions. This can cause cracking of the electrode and a decrease in capacity. Silicon is also highly fragmented during the reaction with lithium, resulting in high irreversible capacity. This also contributes to capacity reduction (or fade) as charge cycles are performed on the battery. The following is a summary of the present disclosure to provide a basic understanding of some aspects. This summary is not intended to identify essential or important elements, or to define any limitations of the embodiments or claims. Additionally, this summary may provide a simplified overview of some aspects that may be described in more detail in other parts of the present disclosure. A composition suitable for use in electrodes is provided. The composition comprises a nitrogen-containing organosilicon material as an additive. In an embodiment, the nitrogen-containing organosilicon material is a uridofunctional organosilicon material. The uridofunctional organosilicon material has been found to provide an electrode material having excellent capacity retention over a large number of charge cycles (i.e., charge/discharge cycles). This is observed at both constant current densities and varied rates. The material having the uridofunctional organosilicon material also exhibits excellent capacity recovery even after the current density is returned. The material also exhibits low impedance during cycling. In one aspect, a composition comprising the following is provided: (a) polymeric resin; (b) Compound represented by the following formula (I); (c) electrode active agent; and (d) Optional binder: Herein, R1 ', R2 ', R3 ', R4 ', R5 ', and R6 ' are independently selected from the group consisting of R4 , OR5 , and ureido functional groups, wherein R4 is independently selected from a monovalent group selected from the group consisting of straight-chain alkyl having 1 to 12 carbon atoms, branched-chain alkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, and aralkyl having 7 to 20 carbon atoms; R5 is independently selected from a monovalent group selected from the group consisting of straight-chain alkyls having 1 to 12 carbon atoms, branched-chain alkyls having 3 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, alkenyls having 2 to 12 carbon atoms, aryls having 6 to 20 carbon atoms, and aralkyls having 7 to 20 carbon atoms; a' or b' is 0-500, provided that at least one of a' or b' is >0; and at least one of R1 ', R2 ', R3 ', R4 ', R5 ', and/or R6 ' is a ureidofunctional group; Here, the above-mentioned ureido functional group is represented by the following formula: Here, R1 and R2 are each independently selected from the group consisting of hydrogen and a monovalent organic group having 1 to 20 carbon atoms; R3 is a divalent straight-chain alkylene group having 1 to 20 carbon atoms or a divalent branched alkylene group having 3 to 20 carbon atoms, each of which optionally contains one or more heteroatoms in the chain; X is selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms and a heterocyclic group containing 1 to 20 heteroatoms, wherein the aromatic group and