CN117043991A - 聚酰亚胺化合物、以及使用其的锂离子二次电池用负极材料、锂离子二次电池用负极及锂离子二次电池 - Google Patents
聚酰亚胺化合物、以及使用其的锂离子二次电池用负极材料、锂离子二次电池用负极及锂离子二次电池 Download PDFInfo
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- CN117043991A CN117043991A CN202280023023.7A CN202280023023A CN117043991A CN 117043991 A CN117043991 A CN 117043991A CN 202280023023 A CN202280023023 A CN 202280023023A CN 117043991 A CN117043991 A CN 117043991A
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- Prior art keywords
- negative electrode
- lithium ion
- ion secondary
- secondary battery
- polyimide
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 58
- 239000004642 Polyimide Substances 0.000 title claims abstract description 57
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 47
- 239000007773 negative electrode material Substances 0.000 title claims description 60
- 150000001875 compounds Chemical class 0.000 title claims description 20
- -1 aromatic diamine compound Chemical class 0.000 claims abstract description 58
- 150000004985 diamines Chemical class 0.000 claims abstract description 14
- 239000007772 electrode material Substances 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 15
- 150000008065 acid anhydrides Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000011871 silicon-based negative electrode active material Substances 0.000 claims description 7
- 239000011255 nonaqueous electrolyte Substances 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000010405 anode material Substances 0.000 claims description 3
- 239000006183 anode active material Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
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- 239000000203 mixture Substances 0.000 description 16
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000007599 discharging Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- 239000006258 conductive agent Substances 0.000 description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 6
- 239000002033 PVDF binder Substances 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 6
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 101150032584 oxy-4 gene Proteins 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 2
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- 239000000945 filler Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
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- 239000003273 ketjen black Substances 0.000 description 1
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- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
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- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
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- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Abstract
本发明提供能够显著改善锂离子二次电池的循环特性的作为电极材料使用的聚酰亚胺。聚酰亚胺,其是作为锂离子二次电池的电极材料使用的聚酰亚胺,二胺成分包含下式(1)表示的芳香族二胺化合物。
Description
技术领域
本发明涉及作为锂离子二次电池的电极材料使用的聚酰亚胺。
背景技术
近年来,以智能手机等为代表的电子设备的小型化急速发展,正在积极地进行小型且轻质、并且能够获得高能量密度的锂离子二次电池的开发。
作为锂离子二次电池中含有的负极活性物质,使用了放电容量高、首次充放电效率及循环特性优异的硅(Si)系材料,但硅在充放电时的膨胀收缩大,有因反复使用而发生负极活性物质间的导电通路的切断、集电体与负极活性物质层的剥离等的风险。
鉴于上述硅系材料的问题,作为构成负极的材料、粘结剂树脂,研究了使用聚酰亚胺化合物来代替以往使用的羧甲基纤维素等(参见专利文献1等)。
然而,其首次充放电效率及循环特性存在改善的余地,要求能够更进一步改善首次充放电效率及循环特性的聚酰亚胺化合物。
现有技术文献
专利文献
专利文献1:国际公开WO2017/138604号册
发明内容
发明所要解决的课题
本发明鉴于上述问题而进行,其所要解决的课题是提供能够显著改善锂离子二次电池的循环特性的作为电极材料使用的聚酰亚胺。
另外,本发明的另一目的在于提供包含该聚酰亚胺的锂离子二次电池的负极材料、由该负极材料形成的负极、及具备该负极的锂离子二次电池。
用于解决课题的手段
本申请的发明人获得下述见解:通过使用特定的芳香族二胺作为二胺成分,从而即使在使用硅系负极活性物质的情况下,也能够抑制电极的膨胀,并且能够显著改善循环特性。本发明基于这样的见解。即,本发明的主旨如下。
[1]聚酰亚胺,其是作为锂离子二次电池的电极材料使用的聚酰亚胺,
二胺成分包含下式(1)表示的芳香族二胺化合物:
[化学式1]
(式中,
R1~R4为氢原子,
R5~R8中的任一者为碳原子数6~10的芳香族基团、苯氧基、苄基或苄氧基,除此以外的R5~R8为氢原子。)。
[2]如[1]所述的聚酰亚胺,其中,酸酐成分包含脂环式酸酐或芳香族酸酐中的至少一种。
[3]如[1]或[2]所述的聚酰亚胺,其中,在二胺成分中以20摩尔%以上的比例包含前述式(1)的化合物。
[4]锂离子二次电池的负极材料,其包含[1]~[3]中任一项所述的聚酰亚胺、和作为负极活性物质的硅系负极活性物质。
[5]如[4]所述的负极材料,其中,以相对于负极活性物质100质量份而言为30质量份以上的比例包含前述硅系负极活性物质。
[6]锂离子二次电池用负极,其为具备负极集电体和形成于前述负极集电体上的负极活性物质层的锂离子二次电池用负极,
前述负极活性物质层由[4]或[5]所述的负极材料形成。
[7]锂离子二次电池,其包含[6]所述的负极、正极和非水电解质。
发明效果
通过将本发明的聚酰亚胺用作锂离子二次电池的电极材料,从而即使在使用硅系负极活性物质的情况下,也能够抑制电极的膨胀,并且能够显著改善循环特性。
具体实施方式
[定义]
本发明中,“溶剂可溶性”是指在100g的有机溶剂中溶解5g以上。
另外,“芳香族基团”包含介由氧原子、氮原子、碳原子与主骨架键合的取代基。此外,芳香族基团包含吡咯基等杂芳香族基团。
[聚酰亚胺]
本发明的聚酰亚胺为包含下式(1)表示的芳香族二胺化合物的二胺成分与酸酐成分的反应物。
[化学式2]
(式中,
R1~R4为氢原子,
R5~R8中的任一者为碳原子数6~10的芳香族基团、苯氧基、苄基或苄氧基,除此以外的R5~R8为氢原子。)
从合成容易性及在电子部件材料领域中的利用这样的观点考虑,碳原子数6~10的芳香族基团优选为未取代,但也可以具有取代基,例如,可举出烷基、氟基或氯基等卤素基团、氨基、硝基、羟基、氰基、羧基、磺酸基等。烷基、芳香族基团可以具有1个以上或2个以上的这些取代基。
作为碳原子数6~10的芳香族基团,例如,可举出苯基、甲苯基、甲基苯基、二甲基苯基、乙基苯基、二乙基苯基、丙基苯基、丁基苯基、氟苯基、五氟苯基、氯苯基、溴苯基、甲氧基苯基、二甲氧基苯基、乙氧基苯基、二乙氧基苯基、氨基苯基、硝基苯基、硝基苄基、氰基苯基、氰基苄基、苯乙基、苯基丙基、苯基氨基、二苯基氨基、联苯基、萘基、苯基萘基、二苯基萘基、蒽基、蒽基苯基、苯基蒽基、并四苯基、菲基、菲基苯基、苯基菲基、芘基、苯基芘基、芴基、苯基芴基、萘基乙基、萘基丙基、蒽基乙基、菲基乙基、或者吡咯基、咪唑基、噻唑基、噁唑基、呋喃基、噻吩基、三唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、嘧啶基、苯并呋喃基、苯并噻吩基、喹啉基、异喹啉基、吲哚基、苯并噻唑基、咔唑基等杂芳香族基团等。
上述的芳香族基团中,从起始原料容易获得性、合成成本方面考虑,优选苯基及甲基苯基。
另外,可以将上述式(1)表示的芳香族二胺化合物组合2种以上而使用。
优选满足上述式(1)的二胺化合物,具体而言,可优选使用下式(2)表示的化合物。
[化学式3]
上述式(1)表示的芳香族二胺化合物可以通过使下式(3)表示的化合物与下式(4)表示的化合物反应后将硝基还原而得到。
[化学式4]
[化学式5]
上述式中,R1’~R4’为氢原子,R5’~R8’中的任一者为碳原子数6~10的芳香族基团、苯氧基、苄基或苄氧基,除此以外的R5’~R8’为氢原子。
另外,X表示羟基或选自氟基、氯基、溴基及碘基中的卤素基团。从与通式(4)表示的化合物的反应性这样的观点考虑,X优选为卤素基团,特别优选为氯基、溴基。
式(3)中,X为羟基的情况下,上述式(3)与(4)表示的化合物的反应优选在N,N’-二环己基碳二亚胺(DCC)这样的脱水缩合剂或对甲苯磺酸这样的有机酸催化剂的存在下进行。另外,上述式(3)中,X为卤素基团的情况下,上述式(3)与(4)表示的化合物的反应优选在三乙胺这样的缚酸剂存在下进行。
具体而言,通过使下式(5)与(6)表示的化合物反应,能够得到上述式(2)表示的二胺化合物。
[化学式6]
[化学式7]
上述式(4)表示的化合物可通过市售而得到、或者通过将合成的下式(7)表示的化合物硝化而得到。下式(7)表示的化合物的硝化可通过使用了浓硫酸与浓硝酸的混酸、硝酸、发烟硝酸、浓硫酸中酸碱金属盐、硝酸乙酰酯、硝鎓盐、氮氧化物等的以往已知的硝化法来进行。
[化学式8]
R5”~R8”中的任一者为碳原子数6~10的芳香族基团、苯氧基、苄基或苄氧基,除此以外的R5”~R8”为氢原子。
本发明中,作为二胺成分,可以包含上述的芳香族二胺化合物以外的二胺化合物。若进行示例,则可举出间苯二胺、对苯二胺、2,4-二氨基甲苯、2,4(6)-二氨基-3,5-二乙基甲苯、5(6)-氨基-1,3,3-三甲基-1-(4-氨基苯基)-茚满、4,4’-二氨基-2,2’-二甲基-1,1’-联苯、4,4’-二氨基-2,2’-二(三氟甲基)-1,1’-联苯、4,4’-二氨基-3,3’-二甲基-1,1’-联苯、3,4’-二氨基二苯基醚、4,4’-二氨基二苯基醚、3,3’-二氨基二苯基砜、4,4’-二氨基二苯基砜、4,4’-二氨基二苯基硫醚、4-氨基苯甲酸4-氨基苯基酯、4,4’-(9-亚芴基)二苯胺、9,9’-双(3-甲基-4-氨基苯基)芴、1,3-双(3-氨基苯氧基)苯、1,3-双(4-氨基苯氧基)苯、1,4-双(4-氨基苯氧基)苯、2,2-双(4-氨基苯基)丙烷、2,2-双(3-甲基-4-氨基苯基)丙烷、4,4’-(六氟异亚丙基)二苯胺、2,2-双(3-氨基-4-甲基苯基)六氟丙烷、2,2-双(3-甲基-4-氨基苯基)苯、2,2-双[4-(4-氨基苯氧基)苯基]丙烷、2,2-双[4-(4-氨基苯氧基)苯基]六氟丙烷、α,α-双[4-(4-氨基苯氧基)苯基]-1,3-二异丙基苯、α,α-双[4-(4-氨基苯氧基)苯基]-1,4-二异丙基苯、3,7-二氨基-二甲基二苯并噻吩、双[4-(4-氨基苯氧基)苯基]砜、5,5-二氧化物、双(3-羧基-4-氨基苯基)甲烷、3,3’-二氨基-4,4’-二羟基-1,1’-联苯、4,4’-二氨基-3,3’-二羟基-1,1’-联苯、2,2-双(3-氨基-4-羟基苯基)丙烷、2,2-双(3-氨基-4-羟基苯基)六氟丙烷、1,3-双(3-羟基-4-氨基苯氧基)苯、2,2-双(3-羟基-4-氨基苯基)苯及3,3’-二氨基-4,4’-二羟基二苯基砜等。
作为聚酰亚胺的二胺成分包含上述式(1)表示的芳香族二胺及除此以外的二胺的情况下,考虑到抑制电极的膨胀、改善再循环特性时,相对于二胺化合物整体而言,上述式(1)表示的芳香族二胺化合物优选以20摩尔%以上的比例被包含,更优选为50摩尔%以上。
作为构成本发明的聚酰亚胺的酸酐,没有特别限制,可以使用聚酰亚胺中使用的各种酸酐。例如,可举出氧双邻苯二甲酸、均苯四甲酸二酐、3-氟均苯四甲酸二酐、3,6-二氟均苯四甲酸二酐、3,6-双(三氟甲基)均苯四甲酸二酐、1,2,3,4-苯四甲酸二酐、2,2’,3,3’-二苯甲酮四甲酸二酐、3,3’,4,4’-二苯甲酮四甲酸二酐、3,3’,4,4’-联苯四甲酸二酐、3,3’,4,4’-联苯砜四甲酸二酐、4,4’-(4,4’-异亚丙基二苯氧基)双邻苯二甲酸二酐、2,3,3’,4’-联苯四甲酸二酐、3,3”,4,4”-三联苯四甲酸二酐、3,3”’,4,4”’-四联苯四甲酸二酐、2,2’,3,3’-联苯四甲酸二酐、亚甲基-4,4’-双邻苯二甲酸二酐、1,1-亚乙基-4,4’-双邻苯二甲酸二酐、2,2-亚丙基-4,4’-双邻苯二甲酸二酐、1,2-亚乙基-4,4’-双邻苯二甲酸二酐、1,3-三亚甲基-4,4’-双邻苯二甲酸二酐、1,4-四亚甲基-4,4’-双邻苯二甲酸二酐、1,5-五亚甲基-4,4’-双邻苯二甲酸二酐、1,3-双〔2-(3,4-二羧基苯基)-2-丙基〕苯二酐、1,4-双〔2-(3,4-二羧基苯基)-2-丙基〕苯二酐、双〔3-(3,4-二羧基苯氧基)苯基〕甲烷二酐、双〔4-(3,4-二羧基苯氧基)苯基〕甲烷二酐、2,2-双〔3-(3,4-二羧基苯氧基)苯基〕丙烷二酐、2,2-双〔4-(3,4-二羧基苯氧基)苯基〕丙烷二酐、二氟亚甲基-4,4’-双邻苯二甲酸二酐、1,1,2,2-四氟-1,2-亚乙基-4,4’-双邻苯二甲酸二酐、3,3’,4,4’-二苯基砜四甲酸二酐、4,4’-氧双邻苯二甲酸二酐、双(3,4-二羧基苯基)醚二酐、4,4’-硫双邻苯二甲酸二酐、磺酰基-4,4’-双邻苯二甲酸二酐、1,3-双(3,4-二羧基苯基)苯二酐、1,4-双(3,4-二羧基苯基)苯二酐、1,3-双(3,4-二羧基苯氧基)苯二酐、1,4-双(3,4-二羧基苯氧基)苯二酐、双(3,4-二羧基苯氧基)二甲基硅烷二酐、1,3-双(3,4-二羧基苯氧基)-1,1,3,3-四甲基二硅氧烷二酐、2,3,6,7-萘四甲酸二酐、1,2,5,6-萘四甲酸二酐、3,4,9,10-苝四甲酸二酐、2,3,6,7-蒽四甲酸二酐、1,2,7,8-菲四甲酸二酐、1,2,3,4-丁烷四甲酸二酐、1,2,3,4-环丁烷四甲酸二酐、环戊烷四甲酸二酐、环己烷-1,2,3,4-四甲酸二酐、环己烷-1,2,4,5-四甲酸二酐、3,3’,4,4’-二环己基四甲酸二酐、羰基-4,4’-双(环己烷-1,2-二甲酸)二酐、亚甲基-4,4’-双(环己烷-1,2-二甲酸)二酐、1,2-亚乙基-4,4’-双(环己烷-1,2-二甲酸)二酐、4,4’-氧双(环己烷-1,2-二甲酸)二酐、4,4’-硫双(环己烷-1,2-二甲酸)二酐、磺酰基-4,4’-双(环己烷-1,2-二甲酸)二酐、3,3’,5,5’-四(三氟甲基)氧基-4,4’-双邻苯二甲酸二酐、3,3’,6,6’-四(三氟甲基)氧基-4,4’-双邻苯二甲酸二酐、5,5’,6,6’-四(三氟甲基)氧基-4,4’-双邻苯二甲酸二酐、3,3’,5,5’,6,6’-六(三氟甲基)氧基-4,4’-双邻苯二甲酸二酐、3,3’-二氟磺酰基-4,4’-双邻苯二甲酸二酐、5,5’-二氟磺酰基-4,4’-双邻苯二甲酸二酐、6,6’-二氟磺酰基-4,4’-双邻苯二甲酸二酐、3,3’,5,5’,6,6’-六氟磺酰基-4,4’-双邻苯二甲酸二酐、3,3’-双(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、5,5’-双(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、6,6’-双(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、3,3’,5,5’-四(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、3,3’,6,6’-四(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、5,5’,6,6’-四(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、3,3’,5,5’,6,6’-六(三氟甲基)磺酰基-4,4’-双邻苯二甲酸二酐、3,3’-二氟-2,2-全氟亚丙基-4,4’-双邻苯二甲酸二酐、5,5’-二氟-2,2-全氟亚丙基-4,4’-双邻苯二甲酸二酐、6,6’-二氟-2,2-全氟亚丙基-4,4’-双邻苯二甲酸二酐、3,3’,5,5’,6,6’-六氟-2,2-全氟亚丙基-4,4’-双邻苯二甲酸二酐、3,3’-双(三氟甲基)-2,2-全氟亚丙基-4,4’-双邻苯二甲酸二酐、乙二醇双偏苯三酸酯二酐、甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、甲基纳迪克酸酐、六氢邻苯二甲酸酐、四氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐、甲基环己烯二甲酸酐、双环[2.2.2]辛-7-烯-2,3,5,6-四甲酸二酐、双环[2.2.2]辛烷-2,3,5,6-四甲酸二酐、3-(羧基甲基)1,2,4-环戊烷甲酸1,4:2,3-二酐、5-(2,5-二氧代基四氢呋喃基)-3-甲基-3-环己烯-1,2-二甲酸酐、4-(2,5-二氧代基四氢呋喃-3-基)-1,2,3,4-四氢萘-1,2-二甲酸酐、5,5’-(1,4-亚苯基)双(六氢-4,7-亚甲基异苯并呋喃-1,3-二酮、八氢-3H,3”H-二螺[4,7-亚甲基异苯并呋喃-5,1’-环戊烷-3’,5”-[4,7]亚甲基异苯并呋喃]-1,1”,2’,3,3”(4H,4”H)-戊酮等。这些可以单独使用一种,也可以并用2种以上而使用。
上述的酸酐中,从能够提高聚酰亚胺的二胺成分中的式(1)表示的芳香族二胺化合物的比例的观点考虑,可优选使用脂环式酸酐、芳香族酸酐。
本发明的聚酰亚胺可通过下述方式得到:使包含上述式(1)表示的芳香族二胺化合物的二胺成分与酸酐成分反应而得到聚酰胺酸后,进行环化脱水反应,转化为聚酰亚胺。得到的聚酰亚胺具有溶剂可溶性,因此通过制成溶解于适当的有机溶剂而得的清漆,容易膜化。
就二胺成分与酸酐成分的混合比而言,相对于酸酐的总量1摩尔%,二胺成分的总量优选为0.5摩尔%~1.5摩尔%,更优选为0.9摩尔%~1.1摩尔%。
二胺成分与酸酐成分的反应优选在有机溶剂中进行。作为有机溶剂,只要不与二胺化合物及酸酐反应、且能够将二胺化合物与酸酐的反应物溶解即可,没有特别限定,可举出N-甲基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N,N’-二甲基咪唑啉酮、γ-丁内酯、二甲基亚砜、环丁砜、1,3-二氧杂环戊环、四氢呋喃、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丁基醚、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇甲基乙基醚、二丙二醇二甲基醚、二乙二醇二丁基醚、二苄基醚、乳酸甲酯、乳酸乙酯、乳酸丁酯、苯甲酸甲酯、苯甲酸乙酯、三甘醇二甲醚、四甘醇二甲醚、甲苯、二甲苯等。从上述式(1)的二胺化合物的溶解性的观点考虑,优选N-甲基-2-吡咯烷酮、N,N’-二甲基咪唑啉酮、γ-丁内酯。
就二胺化合物与酸酐的反应温度而言,在化学酰亚胺化的情况下,优选为40℃以下。另外,在热酰亚胺化的情况下,优选为150~220℃,更优选为170~200℃。
环化脱水反应时,可以使用酰亚胺化催化剂,例如,可使用甲胺、乙胺、三甲胺、三乙胺、丙胺、三丙胺、丁胺、三丁胺、叔丁胺、己胺、三乙醇胺、N,N-二甲基乙醇胺、N,N-二乙基乙醇胺、三乙二胺、N-甲基吡咯烷、N-乙基吡咯烷、苯胺、苄胺、甲苯胺、三氯苯胺、吡啶、三甲基吡啶、二甲基吡啶、甲基吡啶、喹啉、异喹啉、戊内酯等。另外,也可根据需要使用甲苯、二甲苯、乙基环己烷这样的共沸脱水剂、乙酸酐、丙酸酐、丁酸酐、苯甲酸酐等酸催化剂。
二胺化合物与酸酐的反应中,可以使用苯甲酸、邻苯二甲酸酐、氢化邻苯二甲酸酐等封端剂。
此外,也可以通过使用马来酸酐、乙炔基邻苯二甲酸酐、甲基乙炔基邻苯二甲酸酐、苯基乙炔基邻苯二甲酸酐、苯基乙炔基偏苯三甲酸酐、3-或4-乙炔基苯胺等,从而向聚酰亚胺化合物的末端引入双键或三键。
[锂离子二次电池的负极材料]
上述的本发明的聚酰亚胺能够合适地用作锂离子二次电池用负极材料(以下,有时简称为“负极材料”。)、尤其是负极的粘结剂成分。即,能够以包含作为粘结剂的上述聚酰亚胺、和负极活性物质的负极材料的形式使用。
作为粘结剂,可以单独使用上述的聚酰亚胺,也可以包含其他树脂,例如,可以使用聚偏二氟乙烯(PVDF)。另外,作为粘结剂,也可以代替PVDF而使用例如PVDF共聚物树脂、氟系树脂、苯乙烯-丁二烯橡胶(SBR)、乙烯-丙烯橡胶(EPDM)、苯乙烯-丙烯腈共聚物等。作为PVDF共聚物树脂,例如,可以使用六氟丙烯(HFP)、全氟甲基乙烯基醚(PFMV)或四氟乙烯(TFE)、与PVDF的共聚物树脂。作为氟系树脂,例如,可以使用聚四氟乙烯(PTFE)、氟橡胶等。作为其他粘结剂,例如,可以使用羧甲基纤维素(CMC)等多糖类、聚酰亚胺树脂等热塑性树脂。另外,作为粘结剂,也可以并用上述的两种以上。
负极材料中的聚酰亚胺的含量优选为1质量%以上、20质量%以下,更优选为3质量%以上、18质量%以下。通过使负极材料中的聚酰亚胺的含量在上述数值范围内,能够进一步改善锂离子二次电池的循环特性。
作为负极活性物质,从电池容量的观点考虑,优选使用硅系材料。作为硅系材料,可举出硅粒子、锡、镍、铁、铜、银、钴、锰及锌等金属与硅的合金、以及硼、氮、氧及碳等与硅的化合物等。
作为硅系材料,例如,可举出Si、SiO、SiO2、SiB4、Mg2Si、Ni2Si、CoSi2、NiSi2、Cu5Si、FeSi2、MnSi2、ZnSi2、SiC、Si3N4及Si2N2O等,这些之中,优选Si及SiO。
作为负极活性物质,可以使用硅系材料以外的物质,例如,可举出金属锂、金属氧化物、石墨。另外,作为负极材料,可以包含2种以上的负极活性物质。
从电池容量的观点考虑,相对于负极活性物质100质量份而言,上述的硅系负极活性物质优选以30质量份以上的比例被包含,更优选为50质量份以上,进一步优选为95质量份以上。
一个实施方式中,负极材料除了包含上述的聚酰亚胺及负极活性物质以外,还可以包含导电剂。作为导电剂,例如,可举出炭黑(乙炔黑、科琴黑、炉黑等)、石墨、碳纤维、碳片、金属纤维及箔等。这些之中,优选炭黑,更优选乙炔黑。这些导电剂可以单独使用一种,也可以并用两种以上。
相对于负极材料整体而言,负极材料中的导电剂的含量优选为0.1质量%以上、25质量%以下,更优选为1质量%以上、20质量%以下。通过使导电剂的含量在上述数值范围内,能够在负极活性物质层中形成良好的导电通路。
在不损害本发明的特性的范围内,负极材料可以包含添加剂,例如,可举出增稠剂、填料等。
[锂离子二次电池用负极]
本发明的锂离子二次电池用负极具备负极集电体、和形成于该负极集电体上的负极活性物质层,该负极活性物质层由上述的负极材料形成。
集电体没有特别限定,例如,可举出铜、镍、不锈钢、金、铁、铝及它们的合金、镀镍钢、以及镀铬钢等。
负极活性物质层的厚度优选为15μm以上、150μm以下,更优选为20μm以上、120μm以下。通过使负极活性物质层的厚度在上述数值范围内,能够进一步改善锂离子二次电池的首次充放电效率、循环特性。
本发明的锂离子二次电池用负极可以通过将使上述负极材料溶解或分散于有机溶剂而得的溶液涂布于集电体上并干燥来制作。
作为有机溶剂,可以使用上述的物质,从树脂组合物的溶解性或分散性这样的观点考虑,优选N-甲基-2-吡咯烷酮、N,N’-二甲基咪唑啉酮及γ-丁内酯。
涂布方法没有特别限定,例如,可举出模涂法、三辊式转印涂布法、刮刀涂布法、浸渍法、直接辊法及凹版法等。
[锂离子二次电池]
本发明的锂离子二次电池具备上述负极、正极和非水电解质。另外,一个实施方式中,本发明的锂离子二次电池具备配置于负极与正极之间的隔膜。
作为正极,可以适当使用锂离子二次电池的正极中使用的以往已知的正极。正极可以通过将正极形成用材料涂布于集电体上并干燥来制作。
正极形成用材料包含正极活性物质及粘结剂,除此以外,还可以包含上述的导电剂、添加剂。
作为正极活性物质,例如,可举出钴酸锂、镍酸锂、锰酸锂及磷酸铁锂等。
作为粘结剂,可以使用作为负极材料使用的上述的聚酰亚胺、粘结剂。
另外,不限于上述的物质,作为正极,可以使用锂箔等。
隔膜可以使用以往已知的隔膜,例如,可举出纸制隔膜、聚乙烯及聚丙烯等树脂制隔膜、以及玻璃纤维制隔膜等。
上述正极及负极配置于电池容器内,该容器中填充有溶解了电解质的有机溶剂。电解质没有特别限定,例如,可举出LiPF6、LiClO4、LiBF4、LiClF4、LiAsF6、LiSbF6、LiAlO4、LiAlCl4、CF3SO3Li、LiN(CF3SO2)3、LiCl及LiI等非水电解质。这些之中,优选具有高解离度的LiPF6、LiClO4及CF3SO3Li。
有机溶剂也没有特别限定,例如,可举出碳酸酯化合物、内酯化合物、醚化合物、环丁砜化合物、二氧杂环戊烷化合物、酮化合物、腈化合物、卤代烃化合物等。详细而言,可举出:碳酸二甲酯、碳酸甲乙酯、碳酸二乙酯、碳酸亚乙酯、碳酸亚丙酯、乙二醇二甲基碳酸酯、丙二醇二甲基碳酸酯、乙二醇二乙基碳酸酯、碳酸亚乙烯酯等碳酸酯类;γ-丁内酯等内酯类;二甲氧基乙烷、四氢呋喃、2-甲基四氢呋喃、四氢吡喃、1,4-二氧杂环己烷等醚类;环丁砜、3-甲基环丁砜等环丁砜类;1,3-二氧杂环戊烷等二氧杂环戊烷类;4-甲基-2-戊酮等酮类;乙腈、丙腈、戊腈、苯甲腈等腈类;1,2-二氯乙烷等卤代烃类;其他的甲酸甲酯、二甲基甲酰胺、二乙基甲酰胺、二甲基亚砜、咪唑鎓盐、季铵盐等离子性液体等。此外,也可以为它们的混合物。
上述的有机溶剂中,可优选使用负极中使用的聚酰亚胺的溶解性低、能够抑制聚酰亚胺的溶胀的碳酸酯化合物。
锂离子二次电池可以形成为圆筒型、纽扣型、方型、层压体型、其他任意形状,无论形状如何,电池的基本构成是相同的,可以根据目的进行设计变更后实施。例如,为圆筒型时,将在负极集电体上涂布负极活性物质而成的负极和在正极集电体上涂布正极活性物质而成的正极夹着隔膜而卷绕,并将卷绕成的卷绕体收容在电池罐中,注入非水电解液并在上下载置绝缘板,以此状态进行密封而得到。另外,在应用于纽扣型锂二次电池的情况下,以层叠有圆盘状负极、隔膜、圆盘状正极以及不锈钢板的状态收容在纽扣型电池罐中,注入非水电解液,进行密封。
实施例
以下,通过实施例来更具体地说明本发明,但本发明不限于实施例。需要说明的是,以下,只要没有特别说明,则“份”及“%”均为质量基准。
<聚酰亚胺的合成>
[实施例1]
向具备氮导入管、搅拌装置的500ml可分离式烧瓶中,投入下式表示的作为芳香族二胺化合物的双[4-(4-氨基苯氧基)苯基]砜(BAPS)64.88g(150mmol)、下式表示的作为芳香族二胺化合物的4-氨基苯甲酸(2-苯基-4-氨基苯基)酯(PHBAAB)15.22g(50mmol)、下式表示的二苯基-3,3’,4,4’-四甲酸二酐(ODPA)62.04g(200mmol)、N-甲基-2-吡咯烷酮868g、吡啶4.0g(50mmol)及甲苯87g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应9小时,由此得到15重量%的聚酰亚胺溶液。
[化学式9]
[实施例2]
使用与实施例1同样的装置,投入BAPS 43.25g(100mmol)、PHBAAB 30.44g(100mmol)、ODPA 62.04g(200mmol)、N-甲基-2-吡咯烷酮868g、吡啶4.0g(50mmol)及甲苯87g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应9小时,由此得到15重量%的聚酰亚胺溶液。
[比较例1]
使用与实施例1同样的装置,投入BAPS 86.5g(200mmol)、ODPA 62.04g(200mmol)、N-甲基-2-吡咯烷酮868g、吡啶4.0g(50mmol)及甲苯87g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应9小时,由此得到15重量%的聚酰亚胺溶液。
[实施例3]
使用与实施例1同样的装置,投入下式表示的作为芳香族二胺化合物的4,4’-二氨基二苯基硫醚(ASD)43.26g(200mmol)、PHBAAB 60.87g(200mmol)、下式表示的1,2,4,5-环己烷四甲酸二酐(HPMDA)89.67g(400mmol)、N-甲基-2-吡咯烷酮538g、吡啶6.3g(80mmol)及甲苯54g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应14小时,由此得到25重量%的聚酰亚胺溶液。
[化学式10]
[实施例4]
使用与实施例1同样的装置,投入PHBAAB 121.74g(400mmol)、HPMDA 89.67g(400mmol)、N-甲基-2-吡咯烷酮591g、吡啶6.3g(80mmol)及甲苯59g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应14小时,由此得到25重量%的聚酰亚胺溶液。
[比较例2]
使用与实施例1同样的装置,投入ASD 86.52g(400mmol)、HPMDA 89.67g(400mmol)、N-甲基-2-吡咯烷酮485g、吡啶6.3g(80mmol)及甲苯49g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应14小时,由此得到25重量%的聚酰亚胺溶液。
[实施例5]
使用与实施例1同样的装置,投入下式表示的作为芳香族二胺化合物的4,4’-二氨基二苯基醚(ODA)40.05g(200mmol)、PHBAAB 60.87g(200mmol)、ODPA 124.09g(400mmol)、N-甲基-2-吡咯烷酮959g、吡啶6.3g(80mmol)及甲苯96g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应7小时,由此得到18重量%的聚酰亚胺溶液。
[化学式11]
[实施例6]
使用与实施例1同样的装置,投入下式表示的作为芳香族二胺化合物的2,2-双[4-(4-氨基苯氧基)苯基]丙烷(BAPP)61.58g(150mmol)、PHBAAB 45.65g(150mmol)、ODPA93.07g(300mmol)、N-甲基-2-吡咯烷酮863g、吡啶4.8g(60mmol)及甲苯86g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应7小时,由此得到18重量%的聚酰亚胺溶液。
[化学式12]
[实施例7]
使用与实施例1同样的装置,投入ODA 20.02g(100mmol)、BAPP 41.05g(100mmol)、PHBAAB 30.44g(100mmol)、ODPA 93.07g(300mmol)、N-甲基-2-吡咯烷酮792g、吡啶4.8g(60mmol)及甲苯79g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应7小时,由此得到18重量%的聚酰亚胺溶液。
[实施例8]
使用与实施例1同样的装置,投入BAPS 64.87g(150mmol)、PHBAAB 45.65g(150mmol)、ODPA 46.53g(150mmol)、下式表示的3,4,3’,4’-二苯甲酮四甲酸二酐(BTDA)48.33g(150mmol)、N-甲基-2-吡咯烷酮886g、吡啶4.8g(60mmol)及甲苯89g,在氮气氛下,于180℃,一边中途将甲苯排出至体系外一边反应4小时,由此得到18重量%的聚酰亚胺溶液。
[化学式13]
<膜物性的测定>
利用旋涂法,将实施例1~8及比较例1~2中得到的各聚酰亚胺溶液涂布于10cm见方的玻璃板上,于100℃干燥0.5小时,于200℃干燥0.5小时,于250℃干燥1小时。然后,从玻璃板剥离,通过切割,得到长80mm×宽10mm×厚15μm的试验片。
针对以上述方式得到的各试验片,使用拉伸试验机(岛津制作所公司制,商品名:AG-Xplus 50kN),以10mm/分钟的拉伸速度测定MD方向及TD方向各自的弹性模量、拉伸强度及伸长率。算出MD方向及TD方向的各测定值的平均值,作为弹性模量、拉伸强度及伸长率。测定结果如表1所示。需要说明的是,表1中,实施例3及4的“无法测定”表示:在制作试验片时,在将聚酰亚胺溶液涂布于玻璃板而得到聚酰亚胺单独膜的上述方法中,未能顺利地得到单独膜,因此无法测定膜物性。
<循环特性的评价>
将得到的聚酰亚胺作为粘结剂,并按以下的组成混合作为负极活性物质的一氧化硅(SiO)及石墨、以及导电剂,制备了锂离子二次电池用负极材料1。
作为负极用集电体,准备厚度10μm的电解铜箔,在电解铜箔的表面涂布以上述方式得到的负极材料1并干燥,形成厚度50μm的负极活性物质层,由此制作了负极1。
另外,除了将锂离子二次电池用负极材料1的组成如下述这样进行变更以外,与上述同样地制备锂离子二次电池用负极材料2,使用其,与上述同样地制作了负极2。
·聚酰亚胺 10.0质量%
·一氧化硅 87.0质量%
·导电剂 3.00质量%
此外,除了将锂离子二次电池用负极材料1的组成如下述这样进行变更以外,与上述同样地制备了锂离子二次电池用负极材料3。
·聚酰亚胺 15.0质量%
·硅 80.0质量%
·导电剂 5.00质量%
作为负极用集电体,准备厚度10μm的电解铜箔,在电解铜箔的表面涂布以上述方式得到的负极材料3并干燥,形成厚度25μm的负极活性物质层,由此制作负极3。
准备作为正极的锂箔、作为电解液的碳酸亚乙酯及碳酸甲乙酯、聚烯烃制单层隔膜(Celgard株式会社制,Celgard(注册商标)2500),使用以上述方式得到的各负极,制作了纽扣电池型的锂离子二次电池。
将以上述方式制作的锂离子二次电池在25℃的环境下静置24小时。然后,在25℃的环境下如下进行锂离子二次电池的性能评价。
以相当于0.1C的电流密度进行CC(恒定电流)充电至5mV,接着于5mV切换为CV(恒定电压)充电,充电至相当于0.01C的电流密度,然后以相当于0.1C的电流密度进行CC放电至1.2V,将该循环于25℃进行2次。将此时的第1次循环的相当于0.1C的放电容量设为A。
接着,以相当于0.2C的电流密度进行CC(恒定电流)充电至5mV,接着于5mV切换为CV(恒定电压)充电,充电至相当于0.02C的电流密度,然后以相当于0.2C的电流密度进行CC放电至1.2V,将该循环于25℃进行3次,接着,以相当于0.5C的电流密度进行CC(恒定电流)充电至5mV,接着于5mV切换为CV(恒定电压)充电,充电至相当于0.05CC的电流密度,然后以相当于0.5C的电流密度进行CC放电至1.2V,将该循环于25℃进行30次。将此时的第30次循环的相当于0.5C的放电容量设为B。
循环特性基于下式算出:
ΔC(%)=(B/A)×100。
循环特性评价如下述表1所示。
需要说明的是,表1中的“SiO60%”表示锂离子二次电池用负极材料1(负极活性物质中包含60质量%一氧化硅的组成),“SiO100%”表示锂离子二次电池用负极材料2(负极活性物质中包含100质量%一氧化硅的组成),“Si100%”表示锂离子二次电池用负极材料3(负极活性物质中包含100质量%硅的组成)。
[表1]
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Claims (7)
1.聚酰亚胺,其是作为锂离子二次电池的电极材料使用的聚酰亚胺,
二胺成分包含下式(1)表示的芳香族二胺化合物,
[化学式1]
式(1)中,
R1~R4为氢原子,
R5~R8中的任一者为碳原子数6~10的芳香族基团、苯氧基、苄基或苄氧基,除此以外的R5~R8为氢原子。
2.如权利要求1所述的聚酰亚胺,其中,酸酐成分包含脂环式酸酐或芳香族酸酐中的至少一种。
3.如权利要求1或2所述的聚酰亚胺,其中,在二胺成分中以20摩尔%以上的比例包含所述式(1)的化合物。
4.锂离子二次电池的负极材料,其包含权利要求1~3中任一项所述的聚酰亚胺、和作为负极活性物质的硅系负极活性物质。
5.如权利要求4所述的负极材料,其中,以相对于负极活性物质100质量份而言为30质量份以上的比例包含所述硅系负极活性物质。
6.锂离子二次电池用负极,其为具备负极集电体和形成于所述负极集电体上的负极活性物质层的锂离子二次电池用负极,
所述负极活性物质层由权利要求4或5所述的负极材料形成。
7.锂离子二次电池,其包含权利要求6所述的负极、正极和非水电解质。
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