JP2023540723A - リチウム‐硫黄電池用電解液及びこれを含むリチウム‐硫黄電池 - Google Patents
リチウム‐硫黄電池用電解液及びこれを含むリチウム‐硫黄電池 Download PDFInfo
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- JP2023540723A JP2023540723A JP2023514129A JP2023514129A JP2023540723A JP 2023540723 A JP2023540723 A JP 2023540723A JP 2023514129 A JP2023514129 A JP 2023514129A JP 2023514129 A JP2023514129 A JP 2023514129A JP 2023540723 A JP2023540723 A JP 2023540723A
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- Prior art keywords
- lithium
- ether
- heterocyclic compound
- sulfur
- group
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- JDZCKJOXGCMJGS-UHFFFAOYSA-N [Li].[S] Chemical compound [Li].[S] JDZCKJOXGCMJGS-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 239000003792 electrolyte Substances 0.000 title claims abstract description 50
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 54
- 239000003960 organic solvent Substances 0.000 claims abstract description 39
- 239000000654 additive Substances 0.000 claims abstract description 25
- 230000000996 additive effect Effects 0.000 claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000008151 electrolyte solution Substances 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 14
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 14
- 150000004292 cyclic ethers Chemical class 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 51
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 35
- -1 dipropylene glycol dimethylene ether Chemical class 0.000 claims description 33
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 15
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 14
- 239000012528 membrane Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
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- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
- CPULIKNSOUFMPL-UHFFFAOYSA-N 2,4-dimethylthiophene Chemical compound CC1=CSC(C)=C1 CPULIKNSOUFMPL-UHFFFAOYSA-N 0.000 claims description 6
- GWQOOADXMVQEFT-UHFFFAOYSA-N 2,5-Dimethylthiophene Chemical compound CC1=CC=C(C)S1 GWQOOADXMVQEFT-UHFFFAOYSA-N 0.000 claims description 6
- CPLJMYOQYRCCBY-UHFFFAOYSA-N 2-Propylfuran Chemical compound CCCC1=CC=CO1 CPLJMYOQYRCCBY-UHFFFAOYSA-N 0.000 claims description 6
- NWZIYQNUCXUJJJ-UHFFFAOYSA-N 2-butylfuran Chemical compound CCCCC1=CC=CO1 NWZIYQNUCXUJJJ-UHFFFAOYSA-N 0.000 claims description 6
- HLPIHRDZBHXTFJ-UHFFFAOYSA-N 2-ethylfuran Chemical compound CCC1=CC=CO1 HLPIHRDZBHXTFJ-UHFFFAOYSA-N 0.000 claims description 6
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 6
- KJRRQXYWFQKJIP-UHFFFAOYSA-N 3-methylfuran Chemical compound CC=1C=COC=1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 6
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- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 claims description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 3
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims description 3
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- CAQYAZNFWDDMIT-UHFFFAOYSA-N 1-ethoxy-2-methoxyethane Chemical compound CCOCCOC CAQYAZNFWDDMIT-UHFFFAOYSA-N 0.000 claims description 3
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 claims description 3
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- BZYUMXXOAYSFOW-UHFFFAOYSA-N 2,3-dimethylthiophene Chemical compound CC=1C=CSC=1C BZYUMXXOAYSFOW-UHFFFAOYSA-N 0.000 claims description 3
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- KBNFGTQCYBBZJA-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]-2-methylpropane Chemical compound CCOCCOCCOC(C)(C)C KBNFGTQCYBBZJA-UHFFFAOYSA-N 0.000 claims description 3
- RJBIZCOYFBKBIM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]propane Chemical compound COCCOCCOC(C)C RJBIZCOYFBKBIM-UHFFFAOYSA-N 0.000 claims description 3
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- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003277 amino group Chemical group 0.000 claims description 3
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Abstract
Description
リチウム塩、有機溶媒及び添加剤を含むリチウム‐硫黄電池用電解液において、前記添加剤は一つ以上の二重結合を含むヘテロ環化合物を含み、前記ヘテロ環化合物の環内に含まれたヘテロ原子は酸素原子または硫黄原子で、前記有機溶媒は線形エーテル系溶媒、環形エーテル系溶媒及びこれらの組み合わせからなる群から選択されるものである、リチウム‐硫黄電池用電解液を提供する。
前記有機溶媒はジメトキシエタンであってもよい。
正極;負極;前記正極と負極との間に介在される分離膜;及び前記電解液;を含む、リチウム‐硫黄電池を提供する。
本発明によるリチウム塩、有機溶媒及び添加剤を含むリチウム‐硫黄電池用電解液において、前記添加剤は一つ以上の二重結合を含むヘテロ環化合物を含み、前記ヘテロ環化合物の環内で含まれたヘテロ原子は酸素原子または硫黄原子であり、前記有機溶媒は線形エーテル系溶媒、環形エーテル系溶媒及びこれらの組み合わせからなる群から選択されるものである。
本発明によるリチウム‐硫黄電池は、正極;負極;前記正極と負極との間に介在される分離膜;及び電解液;を含み、前記電解液として上述した本発明によるリチウム‐硫黄電池用電解液を含む。
リチウム‐硫黄電池用電解液の製造:製造例1ないし11
[製造例1]
有機溶媒である1,2‐ジメトキシエタンと添加剤である2‐メチルフランをそれぞれ4.5:1の体積比で混合し、0.75Mのリチウムビス(フルオロスルホニル)イミド(LiFSI)と5重量%のLiNO3を溶解させてリチウム‐硫黄電池用電解液を製造した。
有機溶媒である1,2‐ジメトキシエタンと添加剤である2‐メチルフランの混合体積比を下記表1のように異にしたことを除いては、前記製造例1と同様の方法でリチウム‐硫黄電池用電解液を製造した。
有機溶媒として1,2‐ジメトキシエタンだけでなく1,3‐ジオキソランをさらに含んで添加剤である2‐メチルフランと下記表1の体積比で混合したことを除いては、前記製造例1と同様の方法でリチウム‐硫黄電池用電解液を製造した。
添加剤である2‐メチルフランを使用せず、有機溶媒である1,2‐ジメトキシエタン及び1,3‐ジオキソランを下記表1の体積比で混合したことを除いては、前記製造例1と同様の方法でリチウム‐硫黄電池用電解液を製造した。
[実施例1]
水を溶媒にし、正極活物質で硫黄‐炭素複合体、導電材及びバインダーを90:5:5の割合で混合して正極活物質スラリーを製造した。この時、硫黄‐炭素複合体は、硫黄と炭素ナノチューブ(CNT)を70:30の重量比で混合して製造した。また、導電材ではデンカブラックを、バインダーではスチレン‐ブタジエンゴム/カルボキシメチルセルロース(SBR:CMC=7:3、重量比)を使用した。
リチウム‐硫黄電池用電解液で前記製造例2ないし4の電解液を使用したことを除いては、実施例1と同様の方法でリチウム‐硫黄電池を製造した。
リチウム‐硫黄電池用電解液として前記製造例5ないし11の電解液を使用したことを除いては、実施例1と同様の方法でリチウム‐硫黄電池を製造した。
前記実施例1ないし4及び比較例1ないし7によって製造されたリチウム‐硫黄電池に対して、充/放電サイクルの繰り返しを通じて電池の寿命特性を評価した。評価結果は下記表3及び図1に示す。
前記実施例1ないし4及び比較例1ないし7によって製造されたリチウム‐硫黄電池に対して、電池のクーロン効率評価を実施し、80% retentionに到逹するサイクル数までのその結果を図2のように示す。
Claims (13)
- リチウム塩、有機溶媒及び添加剤を含むリチウム‐硫黄電池用電解液において、
前記添加剤は一つ以上の二重結合を含むヘテロ環化合物を含み、
前記ヘテロ環化合物の環内に含まれたヘテロ原子は酸素原子または硫黄原子で、
前記有機溶媒は線形エーテル系溶媒、環形エーテル系溶媒及びこれらの組み合わせからなる群から選択されるものである、リチウム‐硫黄電池用電解液。 - 前記ヘテロ環化合物は3員ないし15員のヘテロ環化合物である、請求項1に記載のリチウム‐硫黄電池用電解液。
- 前記ヘテロ環化合物は、炭素数1ないし4のアルキル基、炭素数3ないし8の環形アルキル基、炭素数6ないし10のアリール基、ハロゲン基、ニトロ基、アミン基、スルホニル基及びこれらの組み合わせからなる群から選択されるもので置換または非置換されたヘテロ環化合物;または
炭素数3ないし8の環形アルキル基、炭素数6ないし10のアリール基及びこれらの組み合わせからなる群から選択されるものと、ヘテロ環化合物の多重環化合物;を含む、請求項2に記載のリチウム‐硫黄電池用電解液。 - 前記ヘテロ環化合物は、フラン、2‐メチルフラン、3‐メチルフラン、2‐エチルフラン、2‐プロピルフラン、2‐ブチルフラン、2,3‐ジメチルフラン、2,4‐ジメチルフラン、2,5‐ジメチルフラン、ピラン、2‐メチルピラン、3‐メチルピラン、4‐メチルピラン、ベンゾフラン、2‐(2‐ニトロビニル)フラン、チオフェン、2‐メチルチオフェン、2‐エチルチオフェン、2‐プロピルチオフェン、2‐ブチルチオフェン、2,3‐ジメチルチオフェン、2,4‐ジメチルチオフェン、2,5‐ジメチルチオフェン及びこれらの組み合わせからなる群から選択されるものである、請求項3に記載のリチウム‐硫黄電池用電解液。
- 前記有機溶媒は線形エーテル系溶媒からなる、請求項1~4のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記線形エーテル系溶媒は、ジメチルエーテル、ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジイソブチルエーテル、エチルメチルエーテル、エチルプロピルエーテル、エチル‐t‐ブチルエーテル、ジメトキシメタン、トリメトキシメタン、ジメトキシエタン、ジエトキシエタン、ジメトキシプロパン、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、トリエチレングリコールジメチルエーテル、テトラエチレングリコールジメチルエーテル、エチレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、トリエチレングリコールジビニルエーテル、ジプロピレングリコールジメチレンエーテル、ブチレングリコールエーテル、ジエチレングリコールエチルメチルエーテル、ジエチレングリコールイソプロピルメチルエーテル、ジエチレングリコールブチルメチルエーテル、ジエチレングリコール‐t‐ブチルエチルエーテル、エチレングリコールエチルメチルエーテル及びこれらの組み合わせからなる群から選択されるものである、請求項1~5のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記環形エーテル系溶媒は、ジオキソラン、メチルジオキソラン、ジメチルジオキソラン、ビニルジオキソラン、メトキシジオキソラン、エチルメチルジオキソラン及びこれらの組み合わせからなる群から選択されるものではない、請求項1~6のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記環形エーテル系溶媒は、ジオキサン、トリオキサン、テトラハイドロフラン、メチルテトラハイドロフラン、ジメチルテトラハイドロフラン、ジメトキシテトラハイドロフラン、エトキシテトラハイドロフラン、テトラハイドロピラン及びこれらの組み合わせからなる群から選択されるものである、請求項1~7のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記有機溶媒100体積比に対してヘテロ環化合物は1体積比ないし24体積比で含まれるものである、請求項1~8のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記有機溶媒100体積比に対してヘテロ環化合物は15体積比ないし24体積比で含まれるものである、請求項1~9のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 前記ヘテロ環化合物は2‐メチルフランで、
前記有機溶媒はジメトキシエタンである、請求項1~10のいずれか一項に記載のリチウム‐硫黄電池用電解液。 - 前記リチウム塩は、LiCl、LiBr、LiI、LiClO4、LiBF4、LiB10Cl10、LiPF6、LiCF3SO3、LiCF3CO2、LiC4BO8、LiAsF6、LiSbF6、LiAlCl4、CH3SO3Li、CF3SO3Li、(CF3SO2)2NLi、(C2F5SO2)2NLi、(SO2F)2NLi、(CF3SO2)3CLi、クロロボランリチウム、低級脂肪族カルボン酸リチウム、4‐フェニルホウ酸リチウム、リチウムイミド及びこれらの組み合わせからなる群から選択されるものである、請求項1~11のいずれか一項に記載のリチウム‐硫黄電池用電解液。
- 正極;
負極;
前記正極と負極との間に介在される分離膜;及び
請求項1ないし請求項12のいずれか一項に記載の電解液;を含む、リチウム‐硫黄電池。
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