JP2010516040A - 共融混合物を含む電解質及びこれを用いる二次電池 - Google Patents
共融混合物を含む電解質及びこれを用いる二次電池 Download PDFInfo
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- JP2010516040A JP2010516040A JP2009546319A JP2009546319A JP2010516040A JP 2010516040 A JP2010516040 A JP 2010516040A JP 2009546319 A JP2009546319 A JP 2009546319A JP 2009546319 A JP2009546319 A JP 2009546319A JP 2010516040 A JP2010516040 A JP 2010516040A
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- Prior art keywords
- electrolyte
- secondary battery
- eutectic mixture
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- containing compound
- Prior art date
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- 239000000374 eutectic mixture Substances 0.000 title claims abstract description 82
- 239000003792 electrolyte Substances 0.000 title claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 50
- 125000003368 amide group Chemical group 0.000 claims abstract description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 19
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 229910052744 lithium Inorganic materials 0.000 claims description 16
- 230000002829 reductive effect Effects 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 238000000926 separation method Methods 0.000 claims description 8
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- 150000002500 ions Chemical class 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- 150000002367 halogens Chemical class 0.000 claims description 6
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
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- 239000011593 sulfur Chemical group 0.000 claims description 4
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- SELYJABLPLKXOY-UHFFFAOYSA-N methyl n,n-dimethylcarbamate Chemical compound COC(=O)N(C)C SELYJABLPLKXOY-UHFFFAOYSA-N 0.000 claims description 2
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 claims description 2
- MYOHNZJKOAODMX-UHFFFAOYSA-N phenyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC=C1 MYOHNZJKOAODMX-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- SUDHEDJJFGYYPL-UHFFFAOYSA-N ethyl n,n-dimethylcarbamate Chemical compound CCOC(=O)N(C)C SUDHEDJJFGYYPL-UHFFFAOYSA-N 0.000 claims 1
- BFRKEWZPWVJIGA-UHFFFAOYSA-N ethyl(2-phenylethyl)carbamic acid Chemical compound CCN(C(O)=O)CCC1=CC=CC=C1 BFRKEWZPWVJIGA-UHFFFAOYSA-N 0.000 claims 1
- AEARPZNULDFPNQ-UHFFFAOYSA-N ethyl-carbamic acid methyl ester Chemical compound CCNC(=O)OC AEARPZNULDFPNQ-UHFFFAOYSA-N 0.000 claims 1
- NYVDNVCZHTXXMW-UHFFFAOYSA-N methyl n-butylcarbamate Chemical compound CCCCNC(=O)OC NYVDNVCZHTXXMW-UHFFFAOYSA-N 0.000 claims 1
- NYXHSRNBKJIQQG-UHFFFAOYSA-N methyl n-methylcarbamate Chemical compound CNC(=O)OC NYXHSRNBKJIQQG-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
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- 239000005518 polymer electrolyte Substances 0.000 description 12
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- 239000000203 mixture Substances 0.000 description 7
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- 239000011572 manganese Substances 0.000 description 6
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- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007774 positive electrode material Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 3
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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Abstract
本発明は、アミド基含有化合物及びリチウム塩からなる共融混合物において、アミド基含有化合物の窒素(N)位置に一つ以上導入される置換基の電子供与性を調節して、共融混合物の電位窓を調節する方法を提供する。
Description
本発明の二次電池用電解質の形態は、特別に制限されないが、好ましくは、2種類の形態、すなわち液体電解質形態又はゲルポリマー電解質形態として適用され得る。
1−1.共融混合物の製造
3:1のモル比でエチルN−メチルカーバメート(CH3NHCOOC2H5)7g及びLiN(SO2CF3)2 6gを混合し、常温、窒素雰囲気で12時間徐々に撹はんして共融混合物13gを得た後、0.3torr真空状態で、水分を20ppm以下に低下させた。
(正極の製造)
正極活物質としてLiCoO2、導電剤として人造黒鉛、バインダーとしてポリビニリデンフロライドを94:3:3の重量比で混合し、得られた混合物にN−メチルピロリドンを加えてスラリーを製造した。製造されたスラリーをアルミニウムホイルに塗布し、130℃で2時間乾燥して正極を製造した。
負極活物質として黒鉛炭素、人造黒鉛及びバインダーを94:3:3の重量比で混合し、N−メチルピロリドンを加えてスラリーを製造した。製造されたスラリーを銅ホイルに塗布し、130℃で2時間乾燥して負極を製造した。
上記のように製造された正極及び負極を1cm2で用意し、その間に分離膜を介在させた。ここに、上記1−1で製造した共融混合物95重量部及びビニレンカーボネート5重量部からなる電解液を注入して、最終的に図1のように二次電池を完成した。
エチルN−メチルカーバメート(CH3NHCOOC2H5)7gの代りに、エチルカーバメート(NH2COOC2H5)6gを用いた以外は、実施例1と同様な方法により共融混合物、及びこれを含む電解質を備える二次電池を製造した。
エチルN−メチルカーバメート(CH3NHCOOC2H5)7gの代りに、メチルカーバメート(NH2COOCH3)6gを用いた以外は、実施例1と同様な方法により共融混合物、及びこれを含む電解質を備える二次電池を製造した。
エチルN−メチルカーバメート(CH3NHCOOC2H5)7gの代りに、メチルN−トリフルオロメチルカーバメート(CF3NHCOOCH3)14gを用いた以外は、実施例1と同様な方法により共融混合物、及びこれを含む電解質を備える二次電池を製造した。
循環電圧電流法(cyclic voltammetry)を用いて、上記実施例1−1及び比較例1〜比較例3で製造した共融混合物の還元電位を測定し、その結果を図2に示す。このとき、作業電極はガラス状炭素、基準電極はリチウム金属、相手電極はリチウム金属を用い、走査速度は50mV/sである。
上記実施例1及び比較例1〜比較例3で製造した二次電池を0.5Cで各々充放電して、サイクルに従う放電容量及び充放電効率を測定し、その結果を各々図3〜図6に示す。
Claims (18)
- (a)窒素(N)位置に電子供与基(EDG)が一つ以上導入されたアミド基含有化合物と、及び、
(b)イオン化可能なリチウム塩からなる、共融混合物を含むことを特徴とする、二次電池用電解質。 - 前記共融混合物が、EDGの導入により還元電位が減少されることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記EDGが、ハメット置換基定数が0未満であることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記アミド基含有化合物が、下記の化学式1又は化学式2で表される化合物であることを特徴とする、請求項1に記載の二次電池用電解質:
R2及びR3の何れか一つ以上がEDGであり、残りは水素又はハロゲンであり、
Xは、水素、炭素、ケイ素、酸素、窒素、リン及び硫黄から選択され、
このとき、i)X=Hであればm=0であり、ii)X=0又はSであればm=1であり、iii)X=N又はPであればm=2であり、iv)X=C又はSiであればm=3であり、そのときのR1は各々独立的に水素、ハロゲン、炭素数1〜20のアルキル基、アルキルアミン基、アルケニル基及びアリール基から選択されるものである。]
R5はEDGであり、
Xが、炭素、ケイ素、酸素、窒素、リン及び硫黄から選択され、このとき、i)X=O、Sであればm=0であり、ii)X=N又はPであればm=1であり、iii)X=C又はSiであればm=2であり、そのときのR4は各々独立的に水素、ハロゲン、炭素数1〜20のアルキル基、アルキルアミン基、アルケニル基及びアリール基から選択されるものであり、
nは1〜10の整数である。] - 前記アミド基含有化合物が、N−エチルアセトアミド、N−メチルウレア、N,N'−ジメチルウレア、エチルN−メチルカーバメート、エチルN−エチルカーバメート、エチルN,N−ジメチルカーバメート、メチルN−メチルカーバメート、メチルN,N−ジメチルカーバメート、N−メチルカプロラクタム、フェニルN,N−ジメチルカーバメート、メチルN−ブチルカーバメート、メチルN−フェニルカーバメート、メチルN−エチルカーバメート及びN−エチル−N−フェニルエチルカーバメートからなる群より選ばれることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記リチウム塩の負イオンが、F−、Cl−、Br−、I−、NO3 −、N(CN)2 −、BF4 −、ClO4 −、PF6 −、(CF3)2PF4 −、(CF3)3PF3 −、(CF3)4PF2 −、(CF3)5PF−、(CF3)6P−、CF3SO3 −、CF3CF2SO3 −、(CF3SO2)2N−、(FSO2)2N−、CF3CF2(CF3)2CO−、(CF3SO2)2CH−、(SF5)3C−、(CF3SO2)3C−、CF3(CF2)7SO3 −、CF3CO2 −、CH3CO2 −、SCN−及び(CF3CF2SO2)2N−からなる群より選ばれることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記電解質が、(a)共融混合物より高い電位(Li/Li+)で還元されて不動態化膜を形成できる第1の化合物と、(b)正極電位より高い酸化電位を有し、過充電電流を消耗する第2の化合物と、又はこれらの全部をさらに含んでなることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記電解質が、液体形態の電解質であることを特徴とする、請求項1に記載の二次電池用電解質。
- 前記電解質が、ゲルポリマー形態の電解質であることを特徴とする、請求項1に記載の二次電池用電解質。
- (i)共融混合物と、及び、
(ii)重合反応によりゲルポリマーを形成できるモノマーを含む電解質前駆体液を重合させて製造されることを特徴とする、請求項9に記載の二次電池用電解質。 - ポリマー又はゲルポリマーに共融混合物を含浸させて製造されることを特徴とする、請求項9に記載の二次電池用電解質。
- ポリマー及び共融混合物を溶媒に溶解させた後、溶媒を除去して製造されることを特徴とする、請求項9に記載の二次電池用電解質。
- 正極と、負極と、分離膜と、及び電解質を備えてなる二次電池であって、
前記電解質が、請求項1〜12の何れか一項に記載の二次電池用電解質であることを特徴とする、二次電池。 - 前記負極が、リチウム対還元電位が0〜1Vであることを特徴とする、請求項13に記載の二次電池。
- 前記負極が、炭素材、金属、金属酸化物、準金属及び準金属含有合金からなる群より選ばれることを特徴とする、請求項13に記載の二次電池。
- 充放電電圧が、4.35Vまでの範囲であることを特徴とする、請求項13に記載の二次電池。
- 共融混合物の電位窓領域を調節する方法であって、
前記共融混合物がアミド基含有化合物と、及びリチウム塩からなるものでああり、
前記アミド基含有化合物の窒素(N)位置に導入される一つ以上の置換基の電子供与性を調節することにより行われることを特徴とす、方法。 - 前記アミド基含有化合物の窒素(N)位置に一つ以上のEDGを導入することにより、前記共融混合物の電位窓領域を本質的に下限側に移動させることを特徴とする、請求項17に記載の調節方法。
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CN104134820A (zh) | 2014-11-05 |
CN104134820B (zh) | 2016-08-31 |
US20100239917A1 (en) | 2010-09-23 |
TW200838011A (en) | 2008-09-16 |
KR100977974B1 (ko) | 2010-08-24 |
JP5673917B2 (ja) | 2015-02-18 |
US8808924B2 (en) | 2014-08-19 |
CN101584077A (zh) | 2009-11-18 |
TWI423495B (zh) | 2014-01-11 |
KR20080067574A (ko) | 2008-07-21 |
WO2008088167A1 (en) | 2008-07-24 |
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