CN114069049B - 一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂及其应用 - Google Patents
一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂及其应用 Download PDFInfo
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- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
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Abstract
Description
技术领域
本发明涉及一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂及其应用,属于锂电池非水电解液添加剂技术领域。
背景技术
锂二次电池自从商业化以来,由于它的比能量高、循环性能好,被广泛用于数码、储能、动力、军用航天和通讯设备等领域。与其他二次电池相比,锂二次电池具有工作电压高、循环寿命长、自放电率低、环境友好、无记忆效应等优点。
在锂离子电池中,电解液的氧化分解劣化电池性能,而且在循环和高温存储过程中常常伴随着金属离子的溶出,导致电池性能严重下降。而随着市场对锂离子电池需求的不断增长,对电池的综合性能需求提出了更高的要求,添加剂的使用是提高锂离子电池综合性能有效途径之一。而添加剂的种类繁多,根据添加剂在电解液中起的作用不同可分为:成膜添加剂、过充保护添加剂、导电添加剂、阻燃添加剂、电解液稳定剂等。无论哪种添加剂,它在电解液中所占的比例很小,但是由于功能明显而被广泛地研究开发。
传统锂二次电池采用碳酸酯类电解液,其在正极和负极表面形成的界面膜并不利于锂离子的传输,导致界面膜的阻抗过高引起电池电化学性能的衰减。成膜添加剂可作为改善正负极界面膜性能的有效手段,其中阻抗性质被看作一个界面膜的重要特性,被寄希望于开发可以降低锂二次电池正极和负极界面膜阻抗的成膜添加剂。
一般来说,含硫类的添加剂对降低电池阻抗有一定作用,进而改善电池的高温性能和低温性能。1,3-丙烷磺酸内酯(PS)、硫酸乙烯酯(DTD)分别作为含硫元素的代表性添加剂,有降低电池阻抗作用成膜添加剂,但1,3-丙烷磺酸内酯(PS)受到欧盟法规管控,使用受限,硫酸乙烯酯(DTD)热稳定性差,若无稳定剂存在,会导致电解液酸值和色度劣化,从而影响电池高温性能。
因此开发新型的成膜添加剂以及电解液稳定剂具有重要意义。。
发明内容
本发明针对现有技术存在的不足,提供一种热稳定性良好的异氰酸酯类电解液添加剂,该添加剂具有良好的降阻抗作用,且能够在电极表面形成稳定的界面膜,进而达到改善界面性质的目的。
本发明解决上述技术问题的技术方案如下:一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂,所述的电解液添加剂结构式入式I所示:
R1和R2相同或者不同,R1和R2分别独立的选自甲基、乙基、丁基、甲氧基、甲磺酰基、乙磺酰基、氟磺酰基、三氟甲磺酰基、全氟乙基磺酰基、苯磺酰基、含烷基苯磺酰基、含氰/含氟苯磺酰基、含烷氧基苯磺酰基、R1和R2可链接形成五元环或六元环中一种。
所述含有磺酰胺结构基团的异氰酸酯类电解液添加剂的化合物机构,已有文献报道制备方法,参考文献:J.Org.Chem.1994,59,3540-3542.;CN1039417;CN1033807;Phosphorus,Sulfur,and Silicon,1992,70,91-97等均已介绍该类材料。
进一步的,所述的电解液添加剂选自如下结构式中的任意一种或两种以上混合:
本发明提供的含有磺酰胺结构基团的异氰酸酯类添加剂热稳定良好,将其配制锂离子电池非水电解液,45℃高温存储30天,电解液酸值和色度稳定。当本发明专利提供的新型添加剂与含硫酸乙烯酯(DTD)或亚甲基二磺酸亚甲基酯(MMDS)混合使用,配制电解液时,能起到DTD或MMDS稳定剂的作用,有效抑制电解液的酸度和色度的升高,从而提升电池的相关性能。
本发明还公开了一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂的应用,所述的电解液添加剂应用于锂离子电池,所述的锂离子电池包括负极、正极、设置在负极和正极之间的隔膜以及电解液。
所述的负极选自由碳基活性材料、硅基活性材料、金属基活性材料或含锂氮化物组成的群组中的单一材料,或者他们中的两种或更多中的混合物。
进一步的,所述的电解液包括溶剂、电解质锂盐和添加剂,所述的添加剂中至少包含所述的含有磺酰胺结构基团的异氰酸酯类电解液添加剂。
进一步的,以电解液总质量为基准,所述的含有磺酰胺结构基团的异氰酸酯类电解液添加剂添加质量含量为0.01~5%,优选0.05~1%。
进一步的,所述的电解质锂盐选自LiPF6、LiClO4、LiBF4、LiBOB、LiODFB、LiTDI、LiTFSI以及LiFSI中的一种或多种,以电解液总质量为基准,所述的电解质锂盐含量为10-20wt%。
进一步的,所述溶剂选自碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯、氟代碳酸亚乙酯、碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸甲乙酯、碳酸二丙酯、碳酸甲丙酯、碳酸乙丙酯、碳酸甲丙炔酯、1,4-丁内酯、丙酸甲酯、丁酸甲酯、乙酸乙酯、丙酸乙酯、丙酸丙酯或丁酸乙酯中的一种或多种的组合。
本发明的有益效果是:
(1)本发明提供的含有磺酰胺结构基团的异氰酸酯类添加剂,其中异氰酸酯基团具有较强的亲电活性,可以与电解液体系中的水分,以及正负极中所包含的的活泼氢作用,减少由活泼氢导致的LiPF6分解;
(2)本发明提供的新型添加剂,磺酰基良好成膜性能,将其添加到电解液中,能够在电极表面形成稳定的界面膜,且磺酰基结构基团给SEI膜引入了S元素,增加离子电导率,故而可以有效地提高锂离子电池循环性能,具体体现于电池在具有良好循环性能的同时,体现出较低的内阻。
(3)本发明提供的新型添加剂,将磺酰基和异氰酸酯结构基团有机结合到一起,具有良好的热稳定性,可起到电解液稳定剂作用,避免电解液高温变色和酸值升高。即使将本发明专利提供的新型添加剂应用到含有易导致电解液酸值和色度升高的硫酸乙烯酯(DTD)或亚甲基二磺酸亚甲基酯(MMDS)电解液体系中,也表现出良好的电解液稳定剂作用,有效抑制电解液变色和酸值升高。将含有本发明专利提供的新型添加剂的电解液应用到电池中,提高高温循环和高温存储性能,且体现出较低的阻抗。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂,下面对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施,本领域技术人员可以在不违背本发明内涵的情况下做类似改进,因此本发明不受下面公开的具体实施例的限制。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施方式的目的,不是旨在于限制本发明。
电池实施例
电池实施例1-8和对比例1-5所列锂离子电池非水电解液的配方如表1所示。
表1.电池实施例1-8和对比例1-5锂离子电池非水电解液的配方
电池实施例1-8和对比例1~5锂离子电池非水电解液用来制备锂离子型扣式电池的方法为:
(1)正极片制备
将正极LiNi0.8Co0.1Mn0.1O2粉末、炭黑(粒度为1000nm)、聚偏二氟乙烯(PVDF)和N,N-二甲基吡咯烷酮(NMP)混合制成均一的浆料,将浆料均匀涂敷在铝箔(15μm)集流体上,然后进行干燥,轧制,得到LiNi0.8Co0.1Mn0.1O2正极材料。于120℃下烘12小时,干燥后的极片中,LiNi0.8Co0.1Mn0.1O2占总涂敷物的94%,粘结剂占4%,炭黑占2%。然后将所得极片裁剪成直径为8mm圆片作为正极。
(2)负极片制备
以人造石墨负极材料为例:将人造石墨,聚偏二氟乙烯(PVDF)和N-甲基吡咯烷酮(NMP)混合制成均一的浆料,将浆料均匀涂敷在铜箔(15μm)集流体上,然后进行干燥,轧制,得到碳负极材料。于120℃下烘12小时,干燥后的极片中,石墨占总涂敷物的96.4%,粘结剂占3.6%,然后将所得极片裁剪成直径为8mm圆片作为负极。
(3)电解液制备
在含水量<1ppm的氩气气氛手套箱中,将锂盐溶解于溶剂中,再加入新型含膦异氰酸酯类,混合均匀后获得电解液;
(4)锂离子电池的制备
以上述步骤(1)和(2)所述的材料作为工作电极,Celgard 2400膜(天津)为隔膜,组装CR2430型扣式电池。组装顺序按负极到正极依次为:负极壳,弹片,垫片,负极片,电解液,隔膜,正极片,正极壳,然后由封口机密封。此操作均在纯氩气手套箱完成,静置6h后取出进行电化学性能测试。
锂离子电池性能测试
测试一、电解液稳定性测试:将上述实施例1~8和对比例1~5制备的锂离子电池电解液分别装到密封铝瓶中,铝瓶用铝塑膜抽真空封装,电解液样品同时置于设定温度为45℃的恒温箱中储存,分别在储存前和30天后在手套箱中取样检测电解液酸度和色度值,酸度采用电位滴定仪测试,酸度值为折算成HF,单位为ppm,色度采用铂-钴比色,色度单位为Hazen。测试结果如表2所示:
表2添加剂对电解液酸值和色度的影响
由表2可知,实施例1~8的电解液在45℃高温下存储30天,电解液的酸度和色度均低于对比例,即使硫酸乙烯酯(DTD)或亚甲基二磺酸亚甲酯(MMDS)的电解液体系,加入本发明提供的新型添加剂,电解液酸值和色度也得到有效抑制,由此本发明提供的新型添加剂能够有效抑制电解液酸度和色度的上升,提高电解液在高温条件下稳定性。
测试二、高温循环性能测试和高温存储性能测试
将制备得到的电池均分别进行下述测试:
①在45℃下,将电池在0.1C倍率下恒流充电至4.3V,再用相应倍率恒流放电至2.7V,此时为首次循环;
②首次循环完成后,以1.0C倍率下恒流充电至4.3V,再用相应倍率恒流放电至2.7V,按照此循环条件分别进行100周、500周循环测试,分别计算得出电池循环100次、500次循环后的容量保持率,其中,循环后的容量保持率按照下式进行计算。各个电池中所得到的相关测试数据参见表2;
循环后的容量保持率=(对应循环次数后的放电容量/首次循环的放电容量)×100%。
高温存储内阻变化率测试:将实施例1-8和对比例1~5所得电池在室温下以1C的充放电倍率进行5次充放电循环测试,最后以1C倍率充到满电状态。记录电池内阻T。将满电状态的电池在60℃下存储15天,记录电池内阻T0,计算得到电池内阻变化率等实验数据,记录结果如表3(实施例1-8的电池编号分别为电池1-电池8,对比例1-5的电池编号分别为电池1#-电池5#)。
内阻变化率=(T-T0)/T×100%。
表3实施例与对比例测试结果
从表3可以明显看出,本发明的新型添加剂的使用能明显改善锂二次电池的高温循环性能以及高温阻抗性能。说明本发明的新型添加剂能够通过对负极电极/电解液界面性质的改善,减少锂二次电池在首次充放电的不可逆容量,降低界面阻抗的同时能够保持界面的稳定性,有助于提升锂二次电池在高温循环稳定性。
由此可以得知,本发明的新型添加剂具有良好的热稳定性,可起到电解液稳定剂作用,避免电解液高温变色和酸值升高。即使将本发明专利提供的新型添加剂应用到含有易导致电解液酸值和色度升高的硫酸乙烯酯(DTD)或亚甲基二磺酸亚甲基酯(MMDS)电解液体系中,也表现出良好的电解液稳定剂作用,有效抑制电解液变色和酸值升高。将含有本发明专利提供的新型添加剂的电解液应用到电池中,提高高温循环性能,且体现出较低的阻抗,具有良好的应用前景。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (7)
3.一种根据权利要求1或2任意一项所述的一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂应用的锂离子电池,其特征在于,所述的电解液添加剂应用于锂离子电池,所述的锂离子电池包括负极、正极、设置在负极和正极之间的隔膜以及电解液。
4.根据权利要求3所述的一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂应用的锂离子电池,其特征在于,所述的电解液包括溶剂、电解质锂盐和添加剂,所述的添加剂中至少包含所述的含有磺酰胺结构基团的异氰酸酯类电解液添加剂。
5.根据权利要求4所述的一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂应用的锂离子电池,其特征在于,以电解液总质量为基准,所述的含有磺酰胺结构基团的异氰酸酯类电解液添加剂添加质量含量为0.01~5%。
6.根据权利要求4所述的一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂应用的锂离子电池,其特征在于,所述的电解质锂盐选自LiPF6、LiClO4、LiBF4、LiBOB、LiODFB、LiTDI、LiTFSI以及LiFSI中的一种或多种,以电解液总质量为基准,所述的电解质锂盐含量为10-20wt%。
7.根据权利要求4所述的一种含有磺酰胺结构基团的异氰酸酯类电解液添加剂应用的锂离子电池,其特征在于,所述溶剂选自碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯、氟代碳酸亚乙酯、碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸甲乙酯、碳酸甲丙酯、碳酸乙丙酯、碳酸甲丙炔酯、1,4-丁内酯、丙酸甲酯、丁酸甲酯、乙酸乙酯、丙酸乙酯、丙酸丙酯或丁酸乙酯中的一种或多种的组合。
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