CN107344917B - 苯基-酰胺材料、其组合物及其作为电解液添加剂的应用 - Google Patents
苯基-酰胺材料、其组合物及其作为电解液添加剂的应用 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 32
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 239000002000 Electrolyte additive Substances 0.000 title claims abstract description 9
- 239000003792 electrolyte Substances 0.000 claims abstract description 70
- 239000000654 additive Substances 0.000 claims abstract description 32
- 230000000996 additive effect Effects 0.000 claims abstract description 30
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims description 37
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 23
- 229910052744 lithium Inorganic materials 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 13
- 229910013870 LiPF 6 Inorganic materials 0.000 claims description 12
- 239000011259 mixed solution Substances 0.000 claims description 12
- 239000007774 positive electrode material Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- SOXUFMZTHZXOGC-UHFFFAOYSA-N [Li].[Mn].[Co].[Ni] Chemical compound [Li].[Mn].[Co].[Ni] SOXUFMZTHZXOGC-UHFFFAOYSA-N 0.000 claims description 2
- QHGJSLXSVXVKHZ-UHFFFAOYSA-N dilithium;dioxido(dioxo)manganese Chemical compound [Li+].[Li+].[O-][Mn]([O-])(=O)=O QHGJSLXSVXVKHZ-UHFFFAOYSA-N 0.000 claims description 2
- OGCCXYAKZKSSGZ-UHFFFAOYSA-N [Ni]=O.[Mn].[Li] Chemical compound [Ni]=O.[Mn].[Li] OGCCXYAKZKSSGZ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001408 amides Chemical group 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 238000004146 energy storage Methods 0.000 abstract description 4
- 239000007772 electrode material Substances 0.000 abstract description 3
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 229910052723 transition metal Inorganic materials 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract description 2
- 239000011257 shell material Substances 0.000 abstract 1
- 238000011056 performance test Methods 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000006230 acetylene black Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000012983 electrochemical energy storage Methods 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- FRMOHNDAXZZWQI-UHFFFAOYSA-N lithium manganese(2+) nickel(2+) oxygen(2-) Chemical compound [O-2].[Mn+2].[Ni+2].[Li+] FRMOHNDAXZZWQI-UHFFFAOYSA-N 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07—ORGANIC CHEMISTRY
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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Abstract
本发明公开了一种苯基‑酰胺材料、其组合物及其作为电解液添加剂的应用,本发明采用新型锂离子电池电解液添加剂体系,其分子结构特征为两端含有苯或芳香环衍生物,同时连接基团中含有酰胺官能团。本发明添加剂能同时实现正极界面稳定和阻断过渡金属溶出‑沉积行为,从而提高电池的循环性能。本发明还公开了使用该电解液体系的锂离子电池。本发明的电解液体系,与现有的锂离子电池符合很好,不需要更换薄膜、电极材料、外壳,在动力电池和储能电池领域具有广泛的应用前景。
Description
技术领域
本发明涉及一种苯基及其衍生物和其应用,特别是涉及一种带有多种末端基团的苯基及其衍生物和其应用,应用于电化学储能材料技术领域。
背景技术
锂离子电池具有能量密度高、输出功率大,平均输出电压高、自放电小,无记忆效应,可快速充放电,循环性能优越,无环境污染等优点,是最具潜力和商业价值的二次电池种类,广泛应用于移动电源、便携电子、家用电器、电动工具、公共交通、智能电网及家庭储能等。然而随着人类社会的发展和科技水平的提高,各行业的发展对二次电池的能量密度、工作寿命等提出了更高的要求。
研究揭示,锂离子电池性能衰减的主要原因之一为电解液/电极界面不稳定,致使溶剂分子在电极表面反应分解,其分解产物如碳酸锂等在电极表面沉积,造成界面阻抗增加,电池极化增大,致使放电电压及容量降低。
发明内容
为了解决现有技术问题,本发明的目的在于克服已有技术存在的不足,提供一种苯基- 酰胺材料、其组合物及其作为电解液添加剂的应用,通过苯基及其衍生物与酰胺基团的组合使用,在不同电极表面均有效提高了电极/电解液的界面稳定性,同时抑制过渡金属的正极溶出进-负极沉积,从而提高了电池的放电电压、放电容量及循环性能,本发明材料适用于锂离子电池电解液的添加剂体系,能广泛应用于电化学储能技术领域。
为达到上述发明创造目的,本发明采用下述技术方案:
一种苯基-酰胺材料,其分子结构的两个末端基团分别为苯环或芳香环衍生物,同时在其分子结构的两个末端基团之间的桥联基团中至少有一个为酰胺官能团。
作为本发明优选的技术方案,上述苯基-酰胺材料的分子结构为如下形式:
其中,在上述分子式中的R1和R2中各自分别独立为亚甲基和酰胺中的任意一种官能团或两种官能团的组合,或者R1和R2的位置为空;在上述分子式中,R3~R12任意一个位置各自独立为-H、羧基、酯基、芳香基及其衍生物、羟基、卤素、烷氧基或者-OLi取代基团,其中在 R3~R7的位置之一与R8~R12中的位置之一中各自至少有一个为-H。
一种本发明苯基-酰胺材料组合物,由至少两种苯基-酰胺材料混合形成组合物。
一种本发明苯基-酰胺材料的应用,锂离子电池包括正极、负极、隔膜和电解液,电解液由基液和电解液添加剂混合而成,以至少一种苯基-酰胺材料作为电解液添加剂,相对于电解液总质量,在电解液中的任意一种苯基-酰胺材料添加的量为0.05-10wt.%,电解液的添加剂采用一种苯基-酰胺材料或者两种苯基-酰胺材料混合形成组合物。
作为上述方案的进一步优选的技术方案,相对于电解液总质量,在电解液中的任意一种苯基-酰胺材料添加的量为0.07-8wt.%。
作为上述方案的进一步优选的技术方案,以至少一种苯基-酰胺材料作为添加剂,与电解基液形成锂电池电解液,锂电池的正极材料采用锰酸锂、锂镍钴锰三元材料、锂镍锰氧和其他富锂材料,形成锂电池体系。
作为上述方案的进一步优选的技术方案,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成。
本发明与现有技术相比较,具有如下显而易见的突出实质性特点和显著优点:
1.本发明采用新型锂离子电池电解液添加剂体系,其分子结构特征为两端含有苯或芳香环衍生物,同时连接基团中含有酰胺官能团;此添加剂可同时实现正极界面稳定和阻断过渡金属溶出-沉积行为,从而提高电池的循环性能;本发明的电解液体系,与现有的锂离子电池符合很好,不需要更换薄膜、电极材料、外壳,在动力电池和储能电池领域具有广泛的应用前景;
2.本发明添加剂制备工艺简单,成本低廉,添加剂能在控制成本的基础上有效提高锂离子电池的容量和循环性能。
具体实施方式
本发明的优选实施例详述如下:
实施例一:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L1,其中L1的分子结构为如下形式:
相对于电解液总质量,其中L1在电解液中含量为8wt%。将添加本实施例添加剂L1的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例二:
本实施例与实施例一基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L2,其中L2的分子结构为如下形式:
相对于电解液总质量,其中L2在电解液中含量为5wt%。将添加本实施例添加剂L2的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例三:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L3,其中L3的分子结构为如下形式:
相对于电解液总质量,其中L3在电解液中含量为3wt%。将添加本实施例添加剂L3的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例四:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L4,其中L4的分子结构为如下形式:
相对于电解液总质量,其中L4在电解液中含量为1wt%。将添加本实施例添加剂L4的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例五:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L5,其中L5的分子结构为如下形式:
相对于电解液总质量,其中L5在电解液中含量为2wt%。将添加本实施例添加剂L5的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例六:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L6,其中L6的分子结构为如下形式:
相对于电解液总质量,其中L6在电解液中含量为0.5wt%。将添加本实施例添加剂L6的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例七:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L7,其中L7的分子结构为如下形式:
相对于电解液总质量,其中L7在电解液中含量为0.7wt%。将添加本实施例添加剂L7的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例八:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L8,其中L8的分子结构为如下形式:
相对于电解液总质量,其中L8在电解液中含量为1wt%。将添加本实施例添加剂L8的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例九:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L9,其中L9的分子结构为如下形式:
相对于电解液总质量,其中L9在电解液中含量为0.3wt%。将添加本实施例添加剂L9的电解液应用于锂电池的电化学性能测试结果如表1所示。
实施例十:
本实施例与前述实施例基本相同,特别之处在于:
在本实施例中,电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成,在本实施例基液中加入添加剂L1和L10的组合物,其中L10的分子结构为如下形式:
相对于电解液总质量,其中L1和L10的组合物在电解液中含量为0.2wt%,其中L1与L10 的质量比为1:2。将添加本实施例添加剂L9的电解液应用于锂电池的电化学性能测试结果如表1所示。
实验测试方法:
分别以商品化NCM(111)为正极活性材料,与导电剂乙炔黑、粘结剂PVDF在NMP溶液中均匀混合,正极活性材料、乙炔黑和粘结剂的质量比分别为80:10:10,然后压片在铝箔上,制得正极,以金属锂为负极,采用玻璃纤维隔膜,分别应用实施例一~十所制备的电解液,对比例采用基液为电解液,组装成CR2032型纽扣锂电池,在LAND-CT2001A充放电测试仪上 4.7-2.5V区间内进行电化学性能测试,电化学性能测试结果如表1所示。
表1.电化学性能测试结果对比
通过表1可知,本发明上述实施例制备的电解液应用于锂电池,在1C充放50周,放电容量为121.9~156.8mAh/g,中值电位为3.792~3.823V vs.Li/Li+,明显由于对比例锂电池。
本发明上述实施例采用新型锂离子电池电解液添加剂体系,其分子结构特征为两端含有苯或芳香环衍生物,同时连接基团中含有酰胺官能团。上述实施例添加剂能同时实现正极界面稳定和阻断过渡金属溶出-沉积行为,从而提高电池的循环性能。本发明上述实施例电解液体系,与现有的锂离子电池符合很好,不需要更换薄膜、电极材料、外壳,在动力电池和储能电池领域具有广泛的应用前景。
上面本发明实施例进行了说明,但本发明不限于上述实施例,还可以根据本发明的发明创造的目的做出多种变化,凡依据本发明技术方案的精神实质和原理下做的改变、修饰、替代、组合或简化,均应为等效的置换方式,只要符合本发明的发明目的,只要不背离本发明苯基-酰胺材料、其组合物及其作为电解液添加剂的应用的技术原理和发明构思,都属于本发明的保护范围。
Claims (4)
2.根据权利要求1所述苯基-酰胺材料的应用,其特征在于:相对于电解液总质量,在电解液中的任意一种苯基-酰胺材料添加的量为0.07-8wt.%。
3.根据权利要求1所述苯基-酰胺材料的应用,其特征在于:电解液的基液为由溶剂和溶质制成LiPF6浓度为1M的混合液,其中溶剂由PC和DMC两种溶剂组分按照体积比为1:1的比例配制而成。
4.一种权利要求1所述苯基-酰胺材料组合物,其特征在于:由至少两种苯基-酰胺材料混合形成组合物。
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