TW201203678A - Electrode protective film-forming agent and electrolyte - Google Patents
Electrode protective film-forming agent and electrolyte Download PDFInfo
- Publication number
- TW201203678A TW201203678A TW100109542A TW100109542A TW201203678A TW 201203678 A TW201203678 A TW 201203678A TW 100109542 A TW100109542 A TW 100109542A TW 100109542 A TW100109542 A TW 100109542A TW 201203678 A TW201203678 A TW 201203678A
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- TW
- Taiwan
- Prior art keywords
- group
- ether
- compound
- electrolyte
- protective film
- Prior art date
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 122
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
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- 125000000468 ketone group Chemical group 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
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- 229920006254 polymer film Polymers 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
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- ZMQDTYVODWKHNT-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) phosphate Chemical compound FC(F)(F)COP(=O)(OCC(F)(F)F)OCC(F)(F)F ZMQDTYVODWKHNT-UHFFFAOYSA-N 0.000 description 1
- HYFGMEKIKXRBIP-UHFFFAOYSA-N tris(trifluoromethyl) phosphate Chemical compound FC(F)(F)OP(=O)(OC(F)(F)F)OC(F)(F)F HYFGMEKIKXRBIP-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/26—Electrodes characterised by their structure, e.g. multi-layered, porosity or surface features
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/64—Liquid electrolytes characterised by additives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/46—Separators, membranes or diaphragms characterised by their combination with electrodes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Secondary Cells (AREA)
- Battery Electrode And Active Subsutance (AREA)
Abstract
Description
201203678 六、發明說明: 【發明所屬之技術領域】 離子電容 本發明是有關於一種尤其對裡二次電池或鍾 器有用的電極保護膜形成劑以及電解液。 【先前技術】201203678 VI. Description of the Invention: [Technical Field] The present invention relates to an electrode protective film forming agent and an electrolytic solution which are useful particularly for a secondary secondary battery or a clock. [Prior Art]
經二次電池等非水電站、波-士 φ a丄丄· 高能量密度之類的特徵, 領域等,且其需要急速擴大,目前,作為以行動電話衣2 記型個人電腦為代表的行動資訊裝置用的標準電池的地位 已確立。當然,隨著可攜式裝置等的高性能化及多功能化, 對作為其電源的非水電解液二次電池亦謀求進一步的高性 用匕化(例如尚容量化及高能量密度化)。正在開發用以應對 該要求的各種方法,例如藉由提高電極填充率的高密度 化、新穎高容量的活性物質等。而且,現實中非水電解液 一次電池藉由該些方法而確實地高容量化。 另外’為了實現非水電解液二次電池的進一步高容量 化,而謀求正極活性物質的利用率的提高或高電壓材料的 開發。其中,尤其受到關注的是由於充電電壓的上升而提 高正極活性物質的利用深度。例如,作為工作電壓為4 2 v 級的非水電解液二次電池的活性物質的鈷複合氧化物 (LiCo〇2)若以目前的U基準充電至4 3v為止,則充電 谷量約為155 mAh/g,相對於此,若充電至4 5 v,則約為 190 mAh/g以上。如此,藉由充電電壓的提高,正極活性 物質的利用率變大。 4 201203678 但疋,隨著電池的高電壓化,電池的容量或能量密产 =2:方面’產生充放電循環特性的降低、或在高溫 儲藏時的膨脹等問題。 的’已提出有解決電池的充放電循環的降低或電池 二脹相題的各種技術。例如於專利文獻丨及專利文獻 二提出有於電解液中添加硫化合物作為添加劑。雖記 些硫化合物吸附於正極表面而抑制電解液的氧 溫:藏特該些硫化合物,充放電循環特性或高 [先前技術文獻] [專利文獻] [專利文獻1]曰本專利特開平7_32〇779號公報 [專利文獻2]日本專利特開平1〇_64591號公報 I發明内容】 本發明的目的在於提供高電壓、古 ,形成劑的電解液(尤其是鐘二次:二: 容ς器用),以及制該些電解液_二次電池或鐘離子電 本發明者為了達成上述目的而進行積極研究, 成本發明。即,本發明是一種 70 有選自由下述〇u)、⑽=護膜形成劑⑺,含 成組群中的至少1種化人物/Δ、、(Β1)及(Β2)所組 们主少1種化合物(Α)或化合物⑻。 ⑷):具有下述通式⑴所表示的稀氧基⑷的 201203678r ^ f I I *^/«Γ 脂肪族烴; (A2):具有烯氧基(a)的多元醇的越; (A3).具有稀氧基(a)的聚氧伸烧基謎 (polyoxyalkylene ether); (B1 ):具有選自由下述通式(2)所表示的取代基、 下述通式(3)所表示的取代基、(曱基)丙烯醯氧基烷基、 及(甲基)丙稀醯基烧基所組成組群中的至少〗種取代基(b) 的多元醇的喊; (B2):具有取代基(b)的聚氧伸烷基醚; [化1] 一 Ο —C = C —τ3 II ⑴ *1*1 丁2 [τ、T2及τ3為氫原子或碳數1〜3的院基] [化2] —R2—c=c一Q3 [式中,R2為碳數1〜3的伸燒基,Qi、Q2及Q3分別 獨立地為氫原子、鹵素原子、碳數1〜4的烷基、碳數1 6 201203678 或2的氟烷基、苯基、氰基、羧基、碳數1〜3的烷氧基或 碳數1〜4的烷氧基羰基] [化3] Q4 Q5 Q6It is a non-hydroelectric power station such as a secondary battery, a wave-study, a high-energy density, and the like, and it needs to be rapidly expanded. Currently, it is a mobile information representative of a mobile phone 2 type personal computer. The status of standard batteries for devices has been established. Of course, with the increase in the performance and the versatility of the portable device, the non-aqueous electrolyte secondary battery as the power source is further improved (for example, capacity is increased and energy density is increased). . Various methods for coping with this demand are being developed, for example, by increasing the density of the electrode filling rate, creating a novel high-capacity active material, and the like. Further, in reality, the non-aqueous electrolyte primary battery is surely increased in capacity by these methods. In addition, in order to further increase the capacity of the nonaqueous electrolyte secondary battery, the utilization of the positive electrode active material is improved or the development of a high voltage material is sought. Among them, particular attention is paid to an increase in the utilization depth of the positive electrode active material due to an increase in the charging voltage. For example, when the cobalt composite oxide (LiCo〇2) which is an active material of a nonaqueous electrolyte secondary battery having a working voltage of 4 2 v is charged to 4 3v on the current U basis, the charge amount is about 155. mAh/g, on the other hand, is about 190 mAh/g or more when charged to 4 5 v. As a result, the utilization rate of the positive electrode active material becomes large by the increase in the charging voltage. 4 201203678 However, with the increase in the voltage of the battery, the capacity or energy density of the battery is in the range of =2: the occurrence of a decrease in the charge/discharge cycle characteristics or the expansion at the time of high-temperature storage. The various techniques have been proposed to address the reduction of the charge and discharge cycle of the battery or the battery expansion. For example, in the patent document 专利 and the patent document 2, it is proposed to add a sulfur compound as an additive to the electrolyte. Although some sulfur compounds are adsorbed on the surface of the positive electrode to suppress the oxygen temperature of the electrolyte: the sulfur compounds are contained, and the charge/discharge cycle characteristics are high. [Prior Art Document] [Patent Literature] [Patent Document 1] Japanese Patent Laid-Open No. 7-32 SUMMARY OF THE INVENTION The object of the present invention is to provide an electrolyte solution of a high voltage, ancient, and forming agent (especially a clock twice: two: ς ς ς ς ς 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 64 In order to achieve the above object, the inventors of the present invention have made active research on the above-mentioned electrolytes. That is, the present invention is a group of 70 selected from the group consisting of 〇u) and (10) = film forming agent (7), and at least one type of person/Δ, (Β1), and (Β2) in a group. One less compound (Α) or compound (8). (4)): 201203678r ^ f II *^/«Γ aliphatic hydrocarbon having a dilute oxy group (4) represented by the following formula (1); (A2): the more the polyol having an alkenyloxy group (a); (A3) a polyoxyalkylene ether having a dilute oxy group (a); (B1) having a substituent represented by the following formula (2), represented by the following formula (3) a polyol of at least one substituent (b) in a group consisting of a substituent, a (decyl) acryloxyalkyl group, and a (meth) propyl sulfhydryl group; (B2): having Substituent (b) polyoxyalkylene ether; [Chemical 1] a Ο - C = C - τ3 II (1) *1 * 1 butyl 2 [τ, T2 and τ3 are hydrogen atoms or a carbon number of 1 to 3 Base] [Chemical 2] - R2 - c = c - Q3 [wherein R2 is a stretching group having a carbon number of 1 to 3, and Qi, Q2 and Q3 are each independently a hydrogen atom, a halogen atom, and a carbon number of 1 to 4; Alkyl group, carbon number 1 6 201203678 or 2 fluoroalkyl group, phenyl group, cyano group, carboxyl group, alkoxy group having 1 to 3 carbon atoms or alkoxycarbonyl group having 1 to 4 carbon atoms] [Chemical 3] Q4 Q5 Q6
[式中’ R3為碳數1〜3的伸烷基,Q4為氫原子或鹵素 原子’ Q5、Q6及Q7分別獨立地為氫原子、鹵素原子、碳 數1〜4的烷基、碳數i或2的氟烷基、苯基、氰基、羧基、 碳數1〜3的烷氧基或碳數1〜4的烷氧基羰基]。 另外’本發明是含有該電極保護膜形成劑(F)的電 解液、含有該電解液的鋰二次電池或鋰離子電容器、以及 具有由該電極保護膜形成劑(F)所包覆的電極活性物質 的鋰二次電池或鋰離子電容器。 [發明的效果] 本發明的電極保護膜形成劑(F)可抑制高電壓下的 面的轉㈣分解,提高級錢職性及高溫儲 解液藉t使用合有本發明的電極保護卿成劑⑺的電 解液’尤其可獲得高電壓、高容量_二次電池或鐘離子 201203678 電容器,並且可提高該些鋰二次電池或鋰離子電容器的高 電壓下的充放電循環性能及高溫儲藏特性。 【實施方式】 本發明的電極保護膜形成劑(F)是含有於電解 而使用,此外亦可以現合於電極中、直接塗佈於 專方法來使用。 本發明的電極保護膜形成劑(F)含有選自由下述 (A1)、(A2)、(A3)、(B1)及(B2)所組成組群中的至 少1種化合物(A)或化合物(B)。 (Α1)·具有通式⑴所表示的烯氧基(a)的脂肪 族烴; (A2).具有烯氧基(a)的多元醇的醚; (A3) ·具有烯氧基(a)的聚氧伸烷基醚; (B1)」具有選自由通式⑺所表示的取代基通式 表示的取代基、(曱基)丙稀酿氧基烧基、及(曱基) ^酿基絲顺成組群巾的至少i種取代 多元 醇的喊; (B2) ·具有取代基⑻的聚氧伸烧基鱗。 人物t、物(A)發揮作為正極保護膜形成劑的功能,化 :m 2發揮作為負極保護卿成義魏。即,化合 m *、化合物(B)在初次充電時,分別於正極及負極 極^制溶劑分解的保護膜。該保制抑制高電壓下的電 面的電解液的分解’提高充放電循環特性。 匕δ物(A)及化合物⑻中,較佳為化合物(A)。 8 201203678 ---__ 作為化合物(A)的(A1)〜(A3)具有通式(1) 所表示的烯氧基(a)。通式(1)中,τι、护及τ3為氫原 子或碳數1〜3的烷基。 具體而言,上述烯氧基(a)可列舉乙烯氧基 (vinyloxy)、1-丙烯氧基(^ρ^ρ^γίοχγ)、丄-丁稀氧基 (Ι-butenyloxy)及 1·曱基丙稀氧基(i_methyi pr〇penyi〇Xy) 等。 該些烯氧基中,較佳為乙烯氧基及丨_丙烯氧基。 [化4] 一 Ο—C = C——τ3 I I ⑴ Τ1 τ2 (Α1)中的脂肪族烴可列舉:碳數2〜2〇的直鏈或分 支的烧烴(乙烧、丙烧、丁烧H己烧、辛院、癸燒、 十二烷、十三烷、十四烷、十五烷、十八烷及二十烷等) 以及碳數2〜20的直鏈或分支的烯烴(乙稀、丙烯、丁稀、 戊稀、己稀、辛烯、癸烯、十—稀、十二稀、十三稀、十 四烯、十五烯、十八烯及二十烯等)。 _ (Α1)可列舉自上述烷烴或者烯烴中丨個以上的氫原 子經烯氧基(a)[較佳為乙烯氧基及丨丙烯氧基]所取代的 化合物。 ^(A2)中的多元醇可列舉2元〜6元的多元醇,具體 而《為.乙二醇()、二乙二醇[In the formula, R3 is an alkylene group having 1 to 3 carbon atoms, and Q4 is a hydrogen atom or a halogen atom. Q5, Q6 and Q7 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a carbon number. Ii or a fluoroalkyl group, a phenyl group, a cyano group, a carboxyl group, an alkoxy group having 1 to 3 carbon atoms or an alkoxycarbonyl group having 1 to 4 carbon atoms]. Further, the present invention relates to an electrolytic solution containing the electrode protective film forming agent (F), a lithium secondary battery or a lithium ion capacitor containing the electrolytic solution, and an electrode coated with the electrode protective film forming agent (F). A lithium secondary battery or a lithium ion capacitor of an active material. [Effects of the Invention] The electrode protective film forming agent (F) of the present invention can suppress the transition of the surface (4) at a high voltage, improve the grade and the high-temperature storage solution, and use the electrode protection of the present invention. The electrolyte of the agent (7) can obtain, in particular, a high voltage, a high capacity _ secondary battery or a clock ion 201203678 capacitor, and can improve the charge and discharge cycle performance and high temperature storage characteristics of the lithium secondary battery or the lithium ion capacitor at a high voltage. . [Embodiment] The electrode protective film forming agent (F) of the present invention is used by being used for electrolysis, or may be used in an electrode and directly applied to a specific method. The electrode protective film forming agent (F) of the present invention contains at least one compound (A) or compound selected from the group consisting of the following (A1), (A2), (A3), (B1) and (B2). (B). (Α1) an aliphatic hydrocarbon having an alkenyloxy group (a) represented by the general formula (1); (A2) an ether of a polyhydric alcohol having an alkenyloxy group (a); (A3) having an alkenyloxy group (a) a polyoxyalkylene ether; (B1)" having a substituent represented by a substituent represented by the formula (7), a (fluorenyl) propylene oxide alkyl group, and a (fluorenyl) aryl group At least i kinds of substituted polyols of the group of silk stalks; (B2) - polyoxyalkylene scaly scales having a substituent (8). The person t and the object (A) function as a positive electrode protective film forming agent, and m 2 functions as a negative electrode protection. That is, when the compound m* and the compound (B) are charged for the first time, a solvolysis protective film is formed on the positive electrode and the negative electrode, respectively. This protection suppresses the decomposition of the electrolytic solution on the electric surface at a high voltage, and improves the charge and discharge cycle characteristics. Among the 匕δ (A) and the compound (8), the compound (A) is preferred. 8 201203678 ---__ (A1) to (A3) as the compound (A) have an alkenyloxy group (a) represented by the formula (1). In the formula (1), τι, 护和τ3 are a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Specifically, the above-mentioned alkenyloxy group (a) may, for example, be a vinyloxy group, a 1-propenyloxy group (^ρ^ρ^γίοχγ), a 丄-butenyloxy group, and a fluorenyl group. Propyloxy (i_methyi pr〇penyi〇Xy) and the like. Among these alkenyloxy groups, a vinyloxy group and a rhodium-propyleneoxy group are preferable.化 Ο C C C C C C C C C C C C C C C 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪 脂肪Burn H-burn, Xinyuan, Shaohao, dodecane, tridecane, tetradecane, pentadecane, octadecane and eicosane, etc.) and linear or branched olefins with a carbon number of 2 to 20 ( Ethylene, propylene, butadiene, pentane, hexene, octene, decene, deuterium, diuret, thirteen, tetradecene, pentadecene, octadecene and hexadecene, etc.). _ (Α1) A compound in which one or more hydrogen atoms from the above alkane or olefin are substituted with an alkenyloxy group (a) [preferably a vinyloxy group and a fluorenyloxy group] can be mentioned. The polyhydric alcohol in (A2) may be a polyhydric alcohol of 2 to 6 yuan, specifically, "ethylene glycol (), diethylene glycol
201203678 */ / / / -r^r*X (diethyleneglycol)、三乙二醇(triethyleneglycol)、丙二 醇(propyleneglycol)、二丙二醇(dipropyleneglycol)、三 丙二醇(tripropyleneglycol)、1,3,丁二醇(l,3-butanediol)、 1,4-丁二醇(l,4-butanediol)、甘油(glycerin)、三經甲基 乙烧 (trimethylolethane )、 三經曱基丙燒 (trimethylolpropane )、2-曱基甘油(2-methylglycerin )、 二甘油(diglycerin )、三甘油(triglycerin )、四甘油 (tetraglycerin )、季戊四醇(pentaerythritol)、二季戊四醇 (dipentaerythritol)及山梨糖醇(sorbitol)等。 較佳為乙二醇、二乙二醇及三乙二醇。 (A2)可列舉由上述多元醇及具有烯氧基(a)[較佳 為乙稀氧基及1-丙烯氧基]的化合物所衍生的喊。 (A3)是由具有烯氧基(a)[較佳為乙烯氧基及丨_丙 烯氧基]的化合物所衍生的聚氧伸烷基醚。 (A3)是於具有烯氧基(a)的化合物上加成環氧烷 (alkylene oxide,以下簡記為A〇 )而獲得。 凡 所加成的AO較佳為碳數為2〜4的AO,具體而古可 列舉:環氧乙烧(ethylene oxide,以下簡記為E〇)、環 丙烷(propylene oxide,以下簡記為p〇)、丨,2環氧丁俨 (l,2-bmylene oxide)、2,3_環氧丁烷、丨,3·環氧丁烷或者二 A ^ T ^ (isobutylene oxide tetrahydrofUran ^ 及該些AO的2種以上的併用。 )、 該些AO +,較佳為E0。A〇的加成莫耳數較佳 莫耳〜10莫耳,尤佳為丨莫耳〜5莫耳。 為1 201203678 化合物(A)中,就充放電循環特性的觀點而言,較 佳為通式(4)所表示的化合物、通< ⑴所表示的化合 物及具有2個以上乙烯氧基或μ烯氧基的環己烧衍生 物。 R4-CH=CH-0-(CH2)p-0-CH=CH-R5 [式中,R4及R5分別獨立地為氫原子或甲基,p為丄 〜10的整數。]201203678 */ / / / -r^r*X (diethyleneglycol), triethyleneglycol, propyleneglycol, dipropyleneglycol, tripropyleneglycol, 1,3, butanediol (l , 3-butanediol), 1,4-butanediol, glycerin, trimethylolethane, trimethylolpropane, 2-mercapto 2-methylglycerin, diglycerin, triglycerin, tetraglycerin, pentaerythritol, dipentaerythritol, and sorbitol. Preferred are ethylene glycol, diethylene glycol and triethylene glycol. (A2) exemplified by the above polyol and a compound having an alkenyloxy group (a) [preferably an ethyleneoxy group and a 1-propenyloxy group]. (A3) is a polyoxyalkylene ether derived from a compound having an alkenyloxy group (a) [preferably a vinyloxy group and a fluorene-propenyloxy group]. (A3) is obtained by adding an alkylene oxide (hereinafter abbreviated as A〇) to a compound having an alkenyloxy group (a). The AO to be added is preferably AO having a carbon number of 2 to 4, and specific examples include: ethylene oxide (hereinafter abbreviated as E〇) and propylene oxide (hereinafter abbreviated as p〇). ), 丨, 2, l-butylene oxide, 2,3-butylene oxide, hydrazine, 3·butylene oxide or di-A ^ T ^ (isobutylene oxide tetrahydrofUran ^ and these AO The combination of two or more types is used.), the AO +, preferably E0. The addition of a mole of A〇 is better. Moer ~ 10 Mo, especially good for Mo Mo ~ 5 Mo. In the case of the compound (A), it is preferably a compound represented by the formula (4), a compound represented by the formula (1), and having two or more ethyleneoxy groups or μ. a cyclohexane derivative of an alkenyloxy group. R4-CH=CH-0-(CH2)p-0-CH=CH-R5 [wherein R4 and R5 are each independently a hydrogen atom or a methyl group, and p is an integer of 丄10. ]
xly 5 /IV R6-CH=CH-0-(C2H40)q-CH=CH-R7 [式中’ R及R分別獨立地為氮原子或曱基,q為1 〜5的整數。] 通式(4)所表示的化合物的具體例可列舉:ι,4_丁二 醇二乙稀喊(1,4-butanedioldivinylether)、1,5-戊二醇二乙 稀趟(l,5-pentanediol divinylether)、1,6-己二醇二乙稀鱗 (1,6-hexanediol divinylether )、1,7-庚二醇二乙稀謎 (l,7-heptanediol divinylether )、1,8-辛二醇二乙烯趟 (l,8-octanediol divinylether )、1,9-壬二醇二乙稀 _ (l,9-nonanediol divinylether )、1,10-癸二醇二乙稀 _ (l,10-decanedioldivinylether)、1,4-丁二醇(1-丙烯基)乙烯 醚(l,4_butanediol(l-propenyl)divinylether)、1,5-戊二醇(1-丙稀基)乙烯鱗(l,5-pentanediol(l-propenyl)divinylether)、 201203678 1,6- 己二醇 (1- 丙烯基)乙烯醚 (l,6-hexanediol(l-propenyl)divinylet;her)、1,7-庚二醇(1-丙稀基)乙稀醚(1,7-heptanediol( 1-propenyl)divinylether )、 1,8- 辛二醇 (1- 丙烯基)乙烯醚 (l,8-octanediol(l-propenyl)divinylether)、1,9-壬二醇(1-丙 婦基)乙稀驗(l,9-nonanediol(l-propenyl)divinylet;her )、 1,10- 癸二醇 (1- 丙烯基)乙烯醚 (l,10-decanediol(l-propenyl)divinylether)、1,4-丁二醇二 (1-丙稀基)騎(l,4-butanediol di(l-propenyl)ether)、1,5-戊 二醇二(1-丙婦基)趟(1,5-pentanediol di(l-propenyl)ether )、1,6-己二醇二(1-丙烯基)醚 (l,6-hexanediol di(l-propenyl)ether)、1,7-庚二醇二(1-丙 稀基)喊(l,7-heptanediol di(l-propenyl)ether)、1,8-辛二醇 一(1-丙稀基)謎(l,8-octanediol di(l-propenyl)ether)、1,9-壬一醇一(1_丙稀基)越(l,9-nonanediol di(l-propenyl)ether) 及 1,10-癸·一 醇 一(1-丙稀基)峻(l,l〇-decanediol di(l-propenyl)ether)。該些化合物可由市售品獲得。 該些化合物中,就充放電循環特性的觀點而言,較佳 為R4及R5分別為氫原子且p為6〜8的化合物。 通式(5)所表示的化合物的具體例可列舉:乙二醇二 乙婦醚、二乙二醇二乙婦域、三乙二醇二乙婦_、四乙二 醇二乙烯醚、五乙二醇二乙烯醚、乙二醇(丨_丙烯基)乙烯 醚、二乙二醇(1·丙烯基)乙烯醚、三乙二醇(丨·丙烯基)乙烯 醚、四乙二醇(1-丙烯基)乙烯醚、五乙二醇(丨_丙烯基)乙烯 12 201203678 醚、乙二醇二(1-丙烯基)醚、二乙二醇二(1_丙烯基)醚、三 乙二醇二(1-丙烯基)醚、四乙二醇二(1_丙烯基)醚及五乙二 醇一(1-丙烯基)醚等。該些化合物可由市售品獲得。 该些化合物中,就充放電循環特性的觀點而言,較佳 為R6及R7為氫原子且q為2或3的化合物。 .具有2個以上乙烯氧基或1_丙烯氧基的環己烷衍生物 的具體例可列舉:1,2_雙(1-丙烯氧基曱基)環己烷 (l,2-bis(l-pr〇penoxymertiyl)cycl〇hexane)、1,3·雙(1-丙烯 氧基曱基)環己烷、1,4-雙(1-丙烯氧基曱基)環己烷、13,5_ 二(1-丙稀氧基曱基)環己烧、1,2·雙(乙稀氧基曱基)環己 烧、1,3-雙(乙稀氧基甲基)環己烧、1,4_雙(乙稀氧基曱基) 環己烧及1,3,5-三(乙烯氧基曱基)環己烧等。該些化合物可 由市售品獲得。 化合物(B)可列舉(B1)及(B2)。 (B1):具有選自由上述通式(2)所表示的取代基、 上述通式(3)所表示的取代基、(甲基)丙烯醯氧基烷基、 及(甲基)丙烯醯基貌基所組成組群中的至少1種取代基(b) 的多元醇的趟; (B2):具有取代基(b)的聚氧伸烷基醚。 (B1)及(B2)具有選自由通式(2)所表示的取代 基、通式(3)所表示的取代基、(甲基)丙烯醯氧基烷基、 及(甲基)丙烯醯基烧基所組成組群中的至少1種取代基 (b)。 取代基(b)中,就負極保護膜的形成容易度的觀點而 13 201203678f j / / / *rpit 言,較佳為通式(2)所表示的取代基、通式(3) 一 的取代基及(曱基)丙烯醯氧基烷基。 不 [化5] —R2—C=C—·Q3 (2)Xly 5 /IV R6-CH=CH-0-(C2H40)q-CH=CH-R7 [wherein R and R are each independently a nitrogen atom or a fluorenyl group, and q is an integer of 1 to 5. Specific examples of the compound represented by the formula (4) include: iota, 4-butanediol divinyl sulfonate (1,4-butanedioldivinylether), 1,5-pentanediol diethylene sulfonate (l, 5) -pentanediol divinylether), 1,6-hexanediol divinylether, 1,7-heptanediol divinylether, 1,8-octane 1,8-octanediol divinylether, 1,9-nonanediol divinylether, 1,10-nonanediol diethylene _ (l,10- Decanedioldivinylether), 1, 4-butanediol (l-propenyl) vinyl ether, 1,5-pentanediol (1-propanyl) vinyl scale (l, 5 -pentanediol(l-propenyl)divinylether), 201203678 1,6-hexanediol (1-propenyl)divinylet;her), 1,7-heptanediol 1-, 1-Heptanediol (1-propenyl) divinylether, 1,8-octanediol (1-propenyl) vinyl ether (1,8-octanediol (l-propenyl)divinylether ), 1,9-nonanediol (1-propanyl) ethylene test (l 9-nonanediol(l-propenyl)divinylet;her ), 1,10-decanediol (l-propenyl) vinyl ether, 1,4-butanediol II (1-propanyl) di(l-propenyl)ether, 1,5-pentanediol di(1-propanyl) oxime (1,5-pentanediol di (l-propenyl) ), 1,6-hexanediol di(l-propenyl)ether, 1,7-heptanediol di(1-propanyl) (1,8-heptanediol di(l-propenyl)ether), 1,8-octanediol di(l-propenyl)ether, 1,9- (1,9-nonanediol di(l-propenyl)ether) and 1,10-癸-ol-ol- 1-propylidene (l,l〇- Decanediol di (l-propenyl) ether). These compounds are available from commercial products. Among these compounds, from the viewpoint of charge and discharge cycle characteristics, a compound in which R4 and R5 are each a hydrogen atom and p is 6 to 8 is preferable. Specific examples of the compound represented by the formula (5) include ethylene glycol dieththyl ether, diethylene glycol diethylene glycol, triethylene glycol diethylene glycol, tetraethylene glycol divinyl ether, and five. Ethylene glycol divinyl ether, ethylene glycol (丨-propenyl) vinyl ether, diethylene glycol (1·propenyl) vinyl ether, triethylene glycol (丨·propylene) vinyl ether, tetraethylene glycol ( 1-propenyl) vinyl ether, pentaethylene glycol (丨-propenyl) ethylene 12 201203678 ether, ethylene glycol bis(1-propenyl) ether, diethylene glycol bis(1-propenyl) ether, triethyl Diol bis(1-propenyl)ether, tetraethylene glycol bis(1-propenyl)ether, pentaethylene glycol mono(1-propenyl)ether, and the like. These compounds are available from commercial products. Among these compounds, from the viewpoint of charge-discharge cycle characteristics, a compound wherein R6 and R7 are a hydrogen atom and q is 2 or 3 is preferred. Specific examples of the cyclohexane derivative having two or more ethyleneoxy groups or 1-propyleneoxy groups include 1,2-bis(1-propenyloxyindenyl)cyclohexane (1,2-bis ( L-pr〇penoxymertiyl)cycl〇hexane), 1,3·bis(1-propenyloxyfluorenyl)cyclohexane, 1,4-bis(1-propoxyoxyindenyl)cyclohexane, 13,5_ Bis(1-propoxyoxyindenyl)cyclohexene, 1,2·bis(ethyloxyindenyl)cyclohexane, 1,3-bis(ethyleneoxymethyl)cyclohexane, 1 4_bis(ethyloxyindenyl) cyclohexane and 1,3,5-tris(ethyleneoxyfluorenyl)cyclohexene. These compounds are available from commercial products. Examples of the compound (B) include (B1) and (B2). (B1): having a substituent represented by the above formula (2), a substituent represented by the above formula (3), a (meth) acryloxyalkyl group, and a (meth) acrylonitrile group a hydrazine of a polyol of at least one substituent (b) in a group consisting of a phenotype; (B2): a polyoxyalkylene ether having a substituent (b). (B1) and (B2) have a substituent represented by the formula (2), a substituent represented by the formula (3), a (meth) propylene decyloxyalkyl group, and a (meth) propylene oxime. At least one substituent (b) in the group consisting of ketone groups. In the substituent (b), from the viewpoint of easiness of formation of the negative electrode protective film, 13 201203678f j / / / *rpit, a substituent represented by the formula (2) and a substitution of the formula (3) are preferred. And (mercapto) acryloxyalkyl. Not [Chemical 5] —R2—C=C—·Q3 (2)
I I Q1 Q2 通式(2)中的R2為碳數1〜3的伸燒基i 2 Q3分別獨立地為氫原子、鹵素原子、碳數1〜4 及 石反數1〜2的敗烧基、苯基、氰基、羧基、碳數1 氧基或碳數1〜4的烷氧基羰基。 的規 碳數1〜3的伸烧基可列舉亞曱基、伸乙基、 基及1,3-伸丙基。該些伸烧基中,就充放電生= 點而言,較佳為亞甲基。 的觀 碳數1〜4的烷基可列舉甲基、乙基、 正丁基及第三T基等。 丙基、 «原子可列舉氟原子、氣原子、漠原子 碳數1〜2的氟烧基可列舉將甲基或乙 1丄 氣乙基、四 的nintr基,可列舉= 一氣甲基、二氟甲基、氟乙基、二氟乙義、 氟乙基及五氟乙基等。 土' 正丙 碳數1〜3的烧氧基例如可列舉甲氣義 一 氧基及異丙氧基。 土、乙氧基、 201203678 碳數1〜4的烷氧基羰基例如可列舉曱氧基羰基、乙氧 基羰基、正丙氧基羰基及異丙氧基羰基等。 ^、(^、(^及以的較佳組合可列舉以下的㈠)〜“)。 (1 ) R2=亞曱基’ Q1=氫原子,Q2=氫原子,q3=苯基; (2) R2=亞曱基’ QL氫原子,Q2=氫原子,qU烷氧 基羰基; (3) R2=亞曱基’ Qk苯基’ Q2=氩原子,q3=笨基; (4) R2=亞曱基’ Qk笨基’ Q2=氫原子,q3=烧氧基II Q1 Q2 R2 in the general formula (2) is a calcining group i 2 Q3 having a carbon number of 1 to 3, and each independently is a hydrogen atom, a halogen atom, a carbon number of 1 to 4, and a pyrene group of 1 to 2 A phenyl group, a cyano group, a carboxyl group, a carbon number 1 oxy group or an alkoxycarbonyl group having 1 to 4 carbon atoms. The alkylene group having a carbon number of 1 to 3 may, for example, be an anthracene group, an exoethyl group, a benzyl group or a 1,3-propanyl group. Among these stretching bases, a methylene group is preferred in terms of charge and discharge. The alkyl group having 1 to 4 carbon atoms may, for example, be a methyl group, an ethyl group, an n-butyl group or a third T group. Examples of the propyl group and the atom include a fluorine atom, a gas atom, and a fluoroalkyl group having a carbon number of 1 to 2, and examples thereof include a methyl group or an ethyl group of an ethylene group and a nintr group of four, and examples thereof include a gas methyl group and a second group. Fluoromethyl, fluoroethyl, difluoroethylene, fluoroethyl and pentafluoroethyl. Soil 'n-propyl" The alkoxy group having 1 to 3 carbon atoms is exemplified by a gas-like monooxy group and an isopropoxy group. Soil, ethoxy group, 201203678 The alkoxycarbonyl group having 1 to 4 carbon atoms may, for example, be a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group or an isopropoxycarbonyl group. ^, (^, (^) and the preferred combination can be exemplified by the following (a)) ~ "). (1) R2 = anthracene group 'Q1 = hydrogen atom, Q2 = hydrogen atom, q3 = phenyl; (2) R2 = anthracenylene 'QL hydrogen atom, Q2 = hydrogen atom, qU alkoxycarbonyl group; (3) R2 = anthracene group 'Qk phenyl group' Q2 = argon atom, q3 = stupid group; (4) R2 = sub曱基' Qk基基' Q2=hydrogen atom, q3=alkoxy
ViU 甘· 叛基, (5 ) R =亞曱基’ Q1=烧氧基羰基,q2=氫原子,q3= 苯基; (6) R2=亞甲基,Qk烷氧基羰基,(^氫原子,q3= 烧氧基裁基。 該些組合中,尤佳為(2)的組合。 [化6]ViU 甘· 叛基, (5) R = fluorenylene 'Q1 = alkoxycarbonyl, q2 = hydrogen atom, q3 = phenyl; (6) R2 = methylene, Qk alkoxycarbonyl, (hydrogen) Atom, q3 = alkoxy groups. Among these combinations, a combination of (2) is preferred.
Q4 Q5 QQ4 Q5 Q
、通式(3)中的R3為碳數1〜3的伸烷基,q4為氫原 子或_素原子,Q5、Q6及Q7分觸立地為氫原子^素 原子、碳數1〜4的烷基、碳數1或2的氟烷基 君千、鹵素 、苯基、氰 15 201203678R3 in the general formula (3) is an alkylene group having 1 to 3 carbon atoms, q4 is a hydrogen atom or a _ atom, and Q5, Q6 and Q7 are in a hydrogen atom, and have a carbon number of 1 to 4. Alkyl, fluoroalkyl group with a carbon number of 1 or 2, halogen, phenyl, cyanide 15 201203678
L 基、羧基、碳數1〜3的烷氧基或碳數1〜4的烷氧基羰基。 通式(3)中的碳數1〜3的伸烷基、鹵素原子、碳數 1〜4的烷基、碳數1或2的氟烷基、碳數1〜3的烷氧基 及碳數1〜4的烷氧基羰基的具體例可列舉與通式(2)中 例示的例子相同的例子。 就負極保護膜的形成容易度及通式(3)所表示的取代 基的穩定性的觀點而言,Q4較佳為氫原子、氣原子及氣原 子,尤佳為氫原子。 就負極保護膜的形成容易度的觀點而言,Q5較佳為氫 原子、碳數1〜4的絲及㈣原子,尤佳為氫原子及碳數 1〜4的烧基’特佳為氫原子。 就負極保護膜的形成容易度的觀點而言,及 佳為氫原子、碳數1〜4的絲及函素原^尤佳 ^ 〜(⑴Q Q、Q Q的較佳組合可列舉以下的⑴ 子、子,Q5如,Q6=氫原 子,二叫 (3 ) R3=亞曱基,(^二氮 子,Q7=氫原子;氣原子原子f氫原 (4)R3=亞曱基,Qk氫原子,q5 Q7=lL^-f ; V虱原子,Q=甲基, 201203678 (5) R3=亞甲基,Q4=氟原子,Q5=氫原子,q6=曱基, Q7=氫原子; (6) R3=亞曱基,Q4=氣原子,Q5=氫原子,q6=甲基, Q7=氫原子; (7) R3=亞曱基,Q4=氫原子,Q5=氫原子,q6=氫原 子,Q7=甲基; (8) R3=亞曱基,Q4=氟原子’ Q5=氫原子,q6=氫原 子,Q7=曱基; (9) R3=亞曱基,Q4=氯原子,Q5=氫原子,Q6=氫原 子,Q7=曱基; (10) R3=亞甲基,Q4=氫原子,Q5=氫原子,q6=曱基, Q7=甲基; (11) R3=亞曱基’ Q4=氟原子,Q5=氫原子,q6=甲基, Q7=甲基; (12 ) R3=亞曱基’ Q4=氣原子’ Q5=氮原子,q6=曱基, Q7=甲基。 該些組合中,尤佳為(1)的組合。 (曱基)丙烯醯氧基烷基較佳為丙烯醯氧基甲基、丙稀 醯氧基乙基、曱基丙烯醯氧基曱基及曱基丙烯醯氧基乙基 等烷基的碳數為1〜2的(曱基)丙烯醯氧基烷基。 (曱基)丙烯醯基烷基較佳為丙烯醯基甲基、丙烯醯基 乙基、甲基丙烯醯基甲基及曱基丙烯醯基乙基等烷基的碳 數為1〜2的(曱基)丙烯醯基烷基。 (B1)中的多元醇可列舉與(A2)中例示的多元醇相 17 201203678 fj t t I 同的多元醇。較佳為乙二醇、二乙二醇及三乙二醇。 (B1)是由多元醇及具有上述取代基(b)的化合物 所衍生的喊。 較佳為通式(6)所表示的化合物。 (6)L group, carboxyl group, alkoxy group having 1 to 3 carbon atoms or alkoxycarbonyl group having 1 to 4 carbon atoms. The alkylene group having 1 to 3 carbon atoms, the halogen atom, the alkyl group having 1 to 4 carbon atoms, the fluoroalkyl group having 1 or 2 carbon atoms, the alkoxy group having 1 to 3 carbon atoms, and carbon in the formula (3) Specific examples of the alkoxycarbonyl group having 1 to 4 may be the same as those exemplified in the formula (2). From the viewpoint of easiness of formation of the negative electrode protective film and stability of the substituent represented by the formula (3), Q4 is preferably a hydrogen atom, a gas atom or a gas atom, and particularly preferably a hydrogen atom. From the viewpoint of easiness of formation of the negative electrode protective film, Q5 is preferably a hydrogen atom, a carbon number of 1 to 4, and a (iv) atom, and particularly preferably a hydrogen atom and a carbon number of 1 to 4 are particularly preferably hydrogen. atom. From the viewpoint of the ease of formation of the negative electrode protective film, and preferably a hydrogen atom, a filament having a carbon number of 1 to 4, and a preferred element of the element (or) ((1)Q Q, QQ, the following (1) , sub, Q5, Q6 = hydrogen atom, two called (3) R3 = sulfhydryl, (^ diazide, Q7 = hydrogen atom; gas atom atom f hydrogenogen (4) R3 = fluorene, Qk hydrogen Atom, q5 Q7=lL^-f ; V虱 atom, Q=methyl, 201203678 (5) R3=methylene, Q4=fluorine, Q5=hydrogen atom, q6=fluorenyl, Q7=hydrogen atom; 6) R3 = fluorenylene, Q4 = gas atom, Q5 = hydrogen atom, q6 = methyl group, Q7 = hydrogen atom; (7) R3 = fluorene group, Q4 = hydrogen atom, Q5 = hydrogen atom, q6 = hydrogen Atom, Q7 = methyl; (8) R3 = fluorenylene, Q4 = fluorine atom 'Q5 = hydrogen atom, q6 = hydrogen atom, Q7 = fluorenyl; (9) R3 = fluorenylene, Q4 = chlorine atom, Q5=hydrogen atom, Q6=hydrogen atom, Q7=mercapto group; (10) R3=methylene group, Q4=hydrogen atom, Q5=hydrogen atom, q6=mercapto group, Q7=methyl group; (11) R3=亚Sulfhydryl group Q4 = fluorine atom, Q5 = hydrogen atom, q6 = methyl group, Q7 = methyl group; (12) R3 = fluorene group 'Q4 = gas atom' Q5 = nitrogen atom, q6 = sulfhydryl group, Q7 = A Base. In the combination, a combination of (1) is particularly preferred. The (fluorenyl) propylene methoxyalkyl group is preferably an acryloxymethyl group, an acryloxyethyl group, a decyl propylene fluorenyl group and an anthracene. The alkyl group having a carbon number of 1 to 2 such as an alkyl propylene oxyethyl group is preferably a fluorenylmethyl group or a propylene group. a (mercapto)propenylalkyl group having 1 to 2 carbon atoms of an alkyl group such as an ethyl group, a methacryloylmethyl group or a mercaptopropenylethyl group. The polyhydric alcohol in (B1) may be exemplified by ( The polyol phase exemplified in A2) is the same polyol, preferably ethylene glycol, diethylene glycol and triethylene glycol. (B1) is a polyol and has the above substituent (b) The compound derived from the compound is preferably a compound represented by the formula (6).
X-(0-RV〇-Y 通式(6)中的X及Y分別獨立地為通式(2)所表示 的取代基、通式(3)所表示的取代基、(甲基)丙烯醯氧基 烷基或(曱基)丙烯醯基烷基。 通式(6)中的R1為碳數1〜3的伸烷基,可列舉亞甲 基、伸乙基、1,2-伸丙基及1,3-伸丙基。該些伸烧基中,就 輸出特性的觀點而言,較佳為伸乙基。 通式(6)中的r為1〜5的整數,就充放電循環特性 的觀點而言,較佳為1〜4的整數,尤佳為2。 (B1)的具體例可列舉:乙二醇二(2-丁烯酸曱酯)醚 (ethyleneglycol di(2-butenoic acid methyl)ether)、二乙二 醇二(2-丁烯酸曱酯)醚、三乙二醇二(2-丁烯酸甲酯)醚、四 乙二醇二(2-丁烯酸甲酯)醚、五乙二醇二(2_丁烯酸曱酯) 趟、乙一醇二肉桂峻(ethyleneglycol dicinnamyl ether)、 二乙二醇二肉桂醚、三乙二醇二肉桂醚、四乙二醇二肉桂 越、五乙二醇二肉桂醚、乙二醇二(4_乙烯基苄基)醚 (ethyleneglycol di(4-vinylbenzyl)ether)、二乙二醇二(4_ 乙 稀基苄基)醚、三乙二醇二(4-乙烯基苄基)醚、四乙二醇二 201203678 (4-乙稀基苄基)醚、五乙二醇二(4-乙烯基苄基)醚、乙二醇 二(1-丙婦酿氧基乙基)鍵(ethyleneglycol di(l-acryloyloxy ethyl)ether)、二乙二醇二(1-丙烯醯氧基乙基)醚、三乙二醇 二(1-丙烯醢氧基乙基)醚、四乙二醇二(1_丙烯醯氧基乙基) 醚、五乙二醇二(1-丙烯醯氧基乙基)蜮、二乙二醇(2_戊烯 酸乙酉日)_( diethyleneglycol (2-pentenoic acid ethyl)ether)、三乙二醇(2-戊烯酸乙酯)醚等。 s亥些化合物可由市售品獲得,或者以公知的方法合成。 (B2)為具有取代基(b)的聚氧伸烷基醚,是於具 有取代基(b)的化合物上加成環氧烷(以下簡記為A〇) 而獲得。 所加成的AO可列舉與(A3)中例示的A〇相同的 A0。較佳為E0。AO的加成莫耳數較佳為i莫耳〜1〇莫 耳,尤佳為1莫耳〜5莫耳。 、 本發明的電極保護膜形成劑(F)含有選自由上述 (ad'uu'wwbd及(B2)所組成組群中的至 少1種化合物(A)或化合物(B)。 本發明的電解液含有電解質(G)、非水溶劑(h)及 電極保護膜形成劑(F)作為必需成分。 藉由使電極保護膜形成劑(F)刀含有於電極或電解液 加電壓,而使電極保護膜形成劑(二 性物質表面聚合形成被膜而成為保護膜。 ,_二次電池絲離子電容;|的錄或電解質中含 有電極保護膜形成劑(F)的情況,於初次充電時形成上 201203678 述保護膜,但亦可使用另行於電極表面(活性物質表面) 形成有電極保護膜(F)的聚合被膜的電極來作為鋰二次 電池或鋰離子電容器的電極。 電解質(G)可使用通常的電解液中使用的電解質, 例如可列舉:LiPF6、LiBF4、LiSbF6、LiAsF6 及 LiC104 等 無機酸的鋰鹽;LiN(CF3S02)2、LiN(C2F5S02)2、 LiC(CF3S02)3等有機酸的鋰鹽。該些電解質中,就電池輸 出及充放電循環特性的觀點而言,較佳為LiPF6。 非水溶劑(H)可使用通常的電解液中使用的溶劑, 例如可使用:内醋(lactone)化合物、環狀或键狀碳酸醋、 鏈狀羧酸酯、環狀或鏈狀醚、磷酸酯、腈(nitrile)化合物、 酿胺(amide)化合物、颯(sulfone)、環丁礙(sulfolane) 等以及該些化合物的混合物。 内酯化合物可列舉5員環(γ- 丁内酯(γ-butyrolactone ) 及γ-戊内S旨(γ-valerolactone)等)及6員環的内醋化合物 (δ-戊内酯等)等。 環狀碳酸酯可列舉:碳酸丙二酯(pr〇pylene carbonate)、碳酸乙二 S旨(ethylene carbonate)及碳酸丁一 醋(butylene carbonate)等0 鏈狀碳酸酯可列舉:碳酸二甲酯(dimethylX-(0-RV〇-Y X and Y in the formula (6) are each independently a substituent represented by the formula (2), a substituent represented by the formula (3), or a (meth) propylene group. a decyloxyalkyl group or a (fluorenyl)propenylalkyl group. R1 in the formula (6) is an alkylene group having 1 to 3 carbon atoms, and examples thereof include a methylene group, an exoethyl group, and a 1,2-extension. The propyl group and the 1,3-propanyl group. Among these stretching groups, from the viewpoint of output characteristics, it is preferably an ethyl group. In the formula (6), r is an integer of 1 to 5, and is charged. From the viewpoint of discharge cycle characteristics, it is preferably an integer of 1 to 4, and particularly preferably 2. (B1) Specific examples thereof include ethylene glycol bis(2-butenoate) ether (ethyleneglycol di (2) -butenoic acid methyl)ether), diethylene glycol bis(2-butenoate) ether, triethylene glycol bis(2-butenoate)ether, tetraethylene glycol bis(2-butene) Methyl ester) ether, pentaethylene glycol bis(2-butenoate) oxime, ethyleneglycol dicinnamyl ether, diethylene glycol dicinnamyl ether, triethylene glycol dicinnamate, four Ethylene glycol di-cinnabar, pentaethylene glycol dicinnamyl ether, ethylene glycol bis(4-vinylbenzyl) ether (ethyleneglycol di(4-vinylbenzyl)ether), diethylene glycol bis(4-ethethylenebenzyl)ether, triethylene glycol bis(4-vinylbenzyl)ether, tetraethylene glycol II 201203678 (4- Ethylene benzyl)ether, pentaethylene glycol bis(4-vinylbenzyl)ether, ethyleneglycol di(l-acryloyloxyethyletherether) , diethylene glycol bis(1-propenyloxyethyl)ether, triethylene glycol bis(1-propenyloxyethyl)ether, tetraethylene glycol bis(1-propyleneoxyethyl) Ether, pentaethylene glycol bis(1-propenyloxyethyl) hydrazine, diethyleneglycol (2-pentenoic acid ethylether), triethylene glycol (diethyleneglycol (2-pentenoic acid ethyl ether)) Ethyl 2-pentenoate) Ether, etc. These compounds are commercially available or can be synthesized by a known method. (B2) is a polyoxyalkylene ether having a substituent (b), which is substituted. The compound of the group (b) is obtained by adding an alkylene oxide (hereinafter abbreviated as A〇). The AO to be added may be the same A0 as the one shown in (A3). It is preferably E0. The molar number is preferably i-mole~1〇m, especially preferably 1m~5m The electrode protective film forming agent (F) of the present invention contains at least one compound (A) or compound (B) selected from the group consisting of the above (ad'uu'wwbd and (B2). The liquid contains an electrolyte (G), a nonaqueous solvent (h), and an electrode protective film forming agent (F) as essential components. When the electrode protective film forming agent (F) blade is applied to the electrode or the electrolyte to apply a voltage, the electrode protective film forming agent (the surface of the amphoteric substance is polymerized to form a film to form a protective film. _ secondary battery wire ion capacitor; In the case where the recording or electrolyte contains the electrode protective film forming agent (F), the protective film of 201203678 is formed at the time of initial charging, but an electrode protective film (F) may be formed separately from the electrode surface (active material surface). The electrode of the polymer film is used as an electrode of a lithium secondary battery or a lithium ion capacitor. The electrolyte (G) may be an electrolyte used in a usual electrolyte solution, and examples thereof include inorganic acids such as LiPF6, LiBF4, LiSbF6, LiAsF6, and LiC104. Lithium salt; lithium salt of an organic acid such as LiN (CF3S02) 2, LiN (C2F5S02) 2, and LiC (CF3S02) 3. Among these electrolytes, LiPF6 is preferred from the viewpoint of battery output and charge/discharge cycle characteristics. As the nonaqueous solvent (H), a solvent used in a usual electrolytic solution can be used, for example, a lactone compound, a cyclic or key carbonate, a chain carboxylate, a cyclic or chain ether, and phosphorus can be used. An ester, a nitrile compound, an amide compound, a sulfone, a sulfolane, etc., and a mixture of the compounds. The lactone compound may be a 5-membered ring (γ-butyrolactone (γ) -butyrolactone), γ-valerolactone, etc., and a 6-membered ring internal vinegar compound (δ-valerolactone, etc.). The cyclic carbonate can be exemplified by propylene carbonate (pr〇pylene). Carbonate, ethylene carbonate, and butylene carbonate, etc., may be exemplified by dimethyl carbonate (dimethyl carbonate).
carbonate)、碳酸曱基乙醋(methyl ethyl carbonate)、石厌I 二乙酿(diethyl carbonate )、碳酸曱基·正丙西曰 (methyl-n-propyl carbonate )、碳酸乙基-正丙西曰 (ethyl-n-propyl carbonate)及碳酸二-正丙醋(di_n-Pr〇Pyl 20 201203678 ^ * * * 'tr“ carbonate)等。 鏈狀羧酸酯可列舉:乙酸甲酯(methyl acetate)、乙酸 乙酯(ethyl acetate )、乙酸丙酯(propyl acetate )及丙酸曱 酯(methyl propionate )等。 環狀醚可列舉:四氫呋喃、四氫吡喃 (tetrahydropyran)、1,3-二氧戊環(l,3-dioxolane)及 1,4-二°惡烧(l,4-dioxane)等。 鏈狀趟可列舉:二甲氧基曱炫(dimethoxy methane) 及 1,2-二曱氧基乙烧(i,2-dimethoxyethane)等。 填酸酯可列舉:鱗酸三甲酯(trimethyl phosphate )、 磷酸三乙酯、磷酸乙基二甲酯、磷酸二乙基甲酯、磷酸三 丙酯、磷酸三丁酯、磷酸三(三氟曱基)酯 (tri(trifluoromethyl)phosphate)、磷酸三(三氣曱基)酯、磷 酸三(三氟乙基)酿、磷酸三(三全氟乙基)g旨、2-乙氧基 二氧磷 雜環戊 -2- _ (2-ethoxy-1,3,2-dioxaphospholan-2-one )、2·三氟乙氧美 -1,3,2-二氧磷雜環戊_2_酮、2-甲氧基乙氧基-i,3,2_二氧填雜 環戊-2·酮等。 ’ 腈化合物可列舉乙腈(acetonitrile)等。醯胺化合物 可列舉二甲基甲酿胺(dimethylformamide)等。 非水溶劑(H)可單獨使用,亦可併用2種以上。 非水溶劑(H)中,就電池輸出及充放電循環特性的 觀點而言,較佳為内酯化合物、鏈狀碳酸酯、鏈狀碳酸酯 及磷酸酯,尤佳為内酯化合物及鏈狀碳酸酯,特佳為内= 21 201203678 一,* .r*i 化合物,最佳為5員環或6員環的内酯化合物,特佳 員環的内酯化合物。 ~ 内酯化合物由於與碳酸酯化合物相比電位窗狹窄,故 而無法用作先前鋰電池用途中的非水溶劑。然而,本發明 的電解液由於存在由電極保護膜形成劑(F)形成的保護 膜,故而内酯化合物亦可用作非水溶劑,與碳酸酯化合物 相比較耐熱保存穩定性優異,因此可使高溫儲藏特性提高。 本發明的電解液較佳為更含有路易斯鹼(c)。上述具 有烯氧基(a)的化合物(a)的反應性高,容易與例如電 解液中微量混合存在的水分和LiPF6等電解質鹽反應產生 的HF等酸性化合物進行反應。藉由在電解液中添加路易 斯鹼(C),可增加化合物(A)於電解液中的穩定性。另 外,於路易斯驗(c)為後述的氮雜冠趟(azacrownether) 衍生物(Cl)的情況,由於氮雜冠醚衍生物(C1)形成負 極保護膜,故而可使充放電循環特性進一步提高。 路易斯鹼(C)可列舉氮雜冠醚衍生物(C1)及*** (triazole)竹生物(C2)等。該些化合物中,就循環特性 的觀點而言,較佳為氮雜冠趟衍生物(Ci)。 氮雜冠醚衍生物(C1)具有包含1個〜4個氮原子的 9員環〜24員環的冠醚骨架,較佳為於該骨架的氮原子的 1個以上鍵結有具有聚合性不飽和雙鍵的取代基的化合 物0 具有1個〜4個氮原子的9員環〜24員環的冠醚骨架 可列舉:氮雜-9-冠-3-喊(4-氣雜-9-冠_3_謎及4,7-二氮雜-9- 22 201203678 冠各謎等)、氮雜、12·冠_4,(4-氮雜·12·冠·4,及41〇 二氮,-12_冠,等)、氮雜孙冠领(4•氮雜_14_冠_4_ 謎及4,他—轉_14•冠4__)、氮雜_15.冠相( Τ^ιΐιΤ^^ ,,一氮雜-15-冠-5-醚等)、氮雜·18•冠冰醚 雜-18-冠-6-趟备;鼠 18 Μ 6 MU ^ 雜 驗及⑽,1卜三氮雜 -18-冠-6-醚專)、氮雜_21•冠领(4氮雜必 二氮雜-21-冠-7-醚及4 1η 16 一备铋μ q, ,1U" 麴,,,,氮雜冠_7,等〕以及氮 ’、 -一C -氮雜-24_冠-8-_、4,1〇-二氮雜·24_冠·8_ 醚及4,10,16_三氮雜_24-冠_8,等)等。 架中,就與鋰離子的配位力的觀點而言, 幸义佳為氮雜-12-冠_4_喊、氮雜·14_冠_4, 氮雜-i2-冠-4-鱗味氮雜_15_冠_5_趟及4,1〇_二氮雜七-冠= 就對鐘離子的配位力的觀點而言,氮雜冠喊骨架 氮原子數較佳為1個〜3個,尤佳^個或2個。”、 氮雜冠驗衍生物(C1)所具有的具有聚合性不飽和雙 鍵的取代基例如可列舉:上料式⑴所麵的取代基、 通式(3)所表示的取代基、(甲基)丙烯醯氧基烷基及^甲 基)丙稀醯基院基等,較佳的取代基亦相同。 氮雜冠醚衍生物(C1)的具體例可列舉:N_(2_丁烯酸 甲酉曰)-4-氮雜-12-冠 _4_ 趟(N-(2-butenoic acid methyl)-4-aza-12-crown-4-ether )、N,N_ 二-(2- 丁 稀酸甲 23 201203678 酯)-4,l〇-二氮雜_12_冠_4_醚、N_(2_丁烯酸曱酯)_4_氮雜-Μ 冠HN,N-二-(2-丁烯酸曱醋M,l〇-二氮雜-15·冠 N-(肉桂基氮雜_12_冠_4,、取-二(肉桂基)4抓二氣 雜-I2-冠、N_(肉桂基)冬氮雜七冠_5醚、N,N-二(肉 桂基)-4,1〇-二氮雜_15_冠·5•醚、N_(4乙烯基苄基)_4 -12-冠-4-醚、N,Nc_(4_乙烯基节基)·4,1〇二氮雜·12_冠< 醚、Ν-(4-乙烯基苄基)_4_氮雜-15-冠_5·醚、Ν,Ν-二-(4-乙烯 基苄基)-4,1〇-二氮雜_15·冠_5_醚、ν,Ν-:-(1-丙烯醯氧基乙 基)-4,10_二氮雜-Ι5-冠_5_醚、N-(l-丙烯醯氧基乙基X氮雜 -14-冠-4-趟、ν_(2_戊烯酸乙酯)冰氮雜·18_冠_6_醚及ν,ν· 二-(2-戊烯酸曱酯)_4,14-二氮雜-18-冠-6-醚等。 本發明中的氮雜冠醚衍生物(C1)可以通常的方法製 造。例如可列舉如下方法:於有機溶劑中,在無觸媒或者 觸媒的存在下’使未經取代的氮雜冠醚與具有聚合性不飽 和雙鍵的齒化烷基進行反應。 有機溶劑例如可列舉:腈系有機溶劑(乙腈、丙腈 (propionitrile )及苯曱腈(benzonitrile )等)、酮系有機溶 劑(丙綱(acetone )及曱基乙基嗣(methyl ethyl ketone ) 等)、醯胺系有機溶劑(曱醯胺、乙醯胺、二甲基曱醯胺及 二曱基乙醯胺等)、醚系有機溶劑(二曱醚、四氫呋喃及二 噁烷等)、酯系有機溶劑(乙酸乙酯及順丁烯二酸二乙酯 等)、含硫有機溶劑(二曱基亞颯(dimethyl sulfoxide)及 環丁颯等)、鹵化烴(氣仿及二氣曱烷等)、烴(己烷、庚 烷、曱苯及二曱苯等)以及該些溶劑的兩種以上的混合物。 24 201203678 觸媒可列舉:驗金屬氮氧化物(例如氫氧化鐘、氫氧 化納及氫氧化卸等)、驗金屬碳酸鹽(碳酸氫鈉、碳酸氫钟、 碳酸鋼及碳酸钟等)及鹼金屬氫化物(氫化鈉及氫化钾等) 等。反應溫度通常為1〇。(:〜150°C,反應時間通常為0.5 小時〜24小時。反應結束後,可視需要中和觸媒,以吸附 劑進行處理而將觸媒去除,加以純化。 具有聚合性不飽和雙鍵的鹵化烧基例如可列舉:4-漠 -2-丁稀酸曱醋(4_bromo-2-butenoic acid methyl ester)、4- 氯-2- 丁烯酸曱酯、1-溴-4-氰基-2- 丁晞 (l-bromo-4-cyano-2-butene)、1-氣-4-氰基-2-丁烯、丙稀 酸氯曱酯(chloromethyl acrylate )、丙稀酸演甲g旨、丙稀酸 -2-氯乙酯、丙烯酸_2_溴乙酯、曱基丙烯酸氣曱酯、甲基丙 烯酸溴曱酯、甲基丙烯酸-2-氣乙酯、甲基丙稀酸溴乙 酯、肉桂基氯(cinnamyl chloride)、肉桂基溴、4-(氯曱基) 苯乙烯(4-(chloromethyl)styrene)及4-(溴曱基)苯乙烯。 ***衍生物(C2 )可列舉:ι,2,3-苯幷*** (l,2,3-benzotriazole)、5-甲基-l,2,3-苯幷***、5,6-二曱基 -1,2,3-苯幷***、1,2,4-***、3-胺基-1,2,4-***、3,5-二胺 基-1,2,4·***、3-胺基-5_甲基_ι,2,4·***、3_胺基·5_乙基 -1,2,4-二唑、3-胺基-5-丙基_ι,2,4·***及3-胺基_5_丁基 -1,2,4-***等。該些***衍生物可獲得市售品。該些*** 衍生物中,就充放電循環特性的觀點而言,較佳為^胺基 -1,2,4-三〇坐。 本發明的祕料更含有化合物⑷及化合物⑻ 25 201203678 -- A- i 以外的負極保護膜形成劑(D)。藉由電解液含有負極保護 膜形成劑(D),負極保護膜的穩定性進一步提高,可使充 放電循環特性進一步提高。 負極保護膜形成劑(D )可列舉:碳酸亞乙烯酯 (vinylene carbonate)、碳酸氟乙二酯、碳酸氣乙二酯、亞 硫酸乙二酯(ethylene sulfite)、亞硫酸丙二酯及…溴个丁 内酯等。該些化合物中,就循環特性的觀點而言,較佳為 碳酸亞乙烯酯。 本發明的電解液中的電極保護膜形成劑(F)、路易斯 驗(C)、負極保護膜形成劑(d)、非水溶劑(H)及電解 質(G)的各較佳含量或濃度為如下所述。 就充放電循環特性、電池容量及高儲藏特性的觀點而 έ ’作為電極保護膜形成劑(F)的化合物(a)的含量基 於電解液的重量,較佳為〇.〇1重量百分比(wt%)〜1〇 wt% ’ 尤佳為 〇 〇5 wt%〜1 wt0/〇。 就電池容量、電池輸出及充放電循環特性的觀點而 言’作為電極保護膜形成劑(F)的化合物(B)的含量基 於電解液的重量,較佳為0.01 wt%〜1〇 wt%,尤佳為〇 〇1 wt% 〜1 wt%。 就電池容量、電池輸出及充放電循環特性的觀點而 言’路易斯鹼(C)的含量基於電解液的重量,較佳為〇wt% 〜10 wt% ’更佳為0.01 wt%〜10 wt% ’尤佳為0·〇5 wt%〜 1 wt%。 就電池容量、電池輸出及充放電循環特性的觀點而 26 201203678 -· ·【-- 言’負極保護膜形成劑(D)的含量基於電解液的重量, 較佳為0 wt%〜5 wt%,更佳為〇 01 wt%〜5 wt%,尤佳為 0.01 wt%〜3 wt%。 就電池輸出及充放電循環特性的觀點而言,非水溶劑 (H)的含量基於電解液的重量,較佳為7〇 wt%〜99 wt°/〇, 尤佳為93 wt%〜99 wt%。Carbonate, methyl ethyl carbonate, diethyl carbonate, methyl-n-propyl carbonate, ethyl-n-propylpropionate (ethyl-n-propyl carbonate) and di-n-propyl acrylate (di_n-Pr〇Pyl 20 201203678 ^ * * * 'tr" carbonate), etc. The chain carboxylic acid esters may be exemplified by methyl acetate. Ethyl acetate (ethyl acetate), propyl acetate, methyl propionate, etc. Examples of the cyclic ether include tetrahydrofuran, tetrahydropyran, and 1,3-dioxolane. (l,3-dioxolane) and 1,4-dioxane, etc. Chain-like oxime can be exemplified by dimethoxy methane and 1,2-dimethoxy group. I, 2-dimethoxyethane, etc. Examples of the acid esters include: trimethyl phosphate, triethyl phosphate, ethyl dimethyl phosphate, diethyl methyl phosphate, and tripropyl phosphate. , tributyl phosphate, tri(trifluoromethyl)phosphate, tris(trimethylsulfonyl) phosphate, phosphoric acid Tris(trifluoroethyl) brewing, tris(trifluoroethyl)phosphoric acid, 2-ethoxydioxolan-2-(2-ethoxy-1,3,2-dioxaphospholan-2 -one ), 2 · trifluoroethoxymethan-1,3,2-dioxaphosphol-2-one, 2-methoxyethoxy-i, 3,2-dioxane -2. A ketone or the like. The acetonitrile compound may, for example, be acetonitrile. The guanamine compound may be dimethylformamide or the like. The nonaqueous solvent (H) may be used singly or in combination of two or more. In the nonaqueous solvent (H), from the viewpoint of battery output and charge/discharge cycle characteristics, a lactone compound, a chain carbonate, a chain carbonate, and a phosphate are preferable, and a lactone compound and a chain are preferable. Carbonate, especially good for inner = 21 201203678 one, * .r*i compound, preferably a 5-membered or 6-membered lactone compound, a lactone compound of a special ring. ~ a lactone compound due to carbonic acid Since the ester compound is narrower than the potential window, it cannot be used as a nonaqueous solvent in the prior lithium battery use. However, the electrolyte of the present invention is protected by the electrode protective film forming agent (F). , And therefore the lactone compound can also be used a non-aqueous solvent, as compared with a carbonate compound is excellent in heat-resistant storage stability, high temperature storage characteristics can be improved. The electrolyte of the present invention preferably further contains a Lewis base (c). The compound (a) having an alkenyloxy group (a) has high reactivity, and is easily reacted with, for example, an acidic compound such as HF which is produced by a reaction between a water which is slightly mixed in an electrolytic solution and an electrolyte salt such as LiPF6. The stability of the compound (A) in the electrolyte can be increased by adding the Lewis base (C) to the electrolyte. Further, in the case where the Lewis test (c) is an azacrownether derivative (Cl) to be described later, since the azacrown ether derivative (C1) forms a negative electrode protective film, the charge and discharge cycle characteristics can be further improved. . The Lewis base (C) may, for example, be an azacrown ether derivative (C1) or a triazole bamboo organism (C2). Among these compounds, from the viewpoint of cycle characteristics, an azacrown derivative (Ci) is preferred. The azacrown ether derivative (C1) has a crown ether skeleton of a 9-membered ring to a 24-membered ring containing 1 to 4 nitrogen atoms, preferably one or more bonds of a nitrogen atom of the skeleton are polymerizable. Compound 0 of the substituent of the unsaturated double bond The crown ether skeleton of the 9-membered ring to 24 ring member having 1 to 4 nitrogen atoms can be enumerated: aza-9-crown-3-cry (4-gas-9) - crown _3_ mystery and 4,7-diaza-9- 22 201203678 crowns, etc.), aza, 12·crown _4, (4-aza·12·crown 4, and 41〇2 Nitrogen, -12_ crown, etc.), aza-sun crown (4 • aza _14_ crown _4_ mystery and 4, he-turn _14 • crown 4__), aza _15. crown phase ( Τ ^ ΐΐιΤ^^ ,, aza-hetero-15-crown-5-ether, etc.), aza·18•crown ether ether-18-crown-6-prepared; mouse 18 Μ 6 MU ^ abundance and (10),1 Bu triaza-18-crown-6-ether special), aza-21• crown collar (4 aza-bidiazepine-21-crown-7-ether and 4 1η 16 a 铋μq, ,1U" ; 麴,,,, aza crown _7, etc.] and nitrogen ', -C-aza-24_crown-8-_, 4,1〇-diaza·24_crown·8_ ether and 4 , 10, 16_ triaza-24-crown _8, etc.). In the framework, from the viewpoint of the coordination force with lithium ions, Xingyi Jia is aza-12-crown_4_ shouting, aza·14_crown_4, aza-i2-crown-4-scale Aza nitrogen _15_ crown _5_趟 and 4,1〇_diazepine seven-crown = from the viewpoint of the coordination force of the bell ion, the number of nitrogen atoms in the aza-crown skeleton is preferably one ~3, especially good ^ or 2. The substituent having a polymerizable unsaturated double bond which the aza crown derivative (C1) has, for example, a substituent represented by the above formula (1), a substituent represented by the formula (3), The methyl group is a propylene methoxyalkyl group and a methyl group propyl thiol group, and the preferred substituents are also the same. Specific examples of the azacrown ether derivative (C1) include: N_(2_丁N-(2-butenoic acid methyl)-4-aza-12-crown-4-ether ), N,N_ di-(2-) Butyric acid A 23 201203678 Ester)-4,l〇-diazepine_12_crown_4_ether, N_(2-butenoate) _4_aza-Μ Crown HN,N-di-( 2-butenoic acid vinegar vinegar M, l〇-diazepine-15·crown N-(cinnamyl aza _12_crown _4, taken-two (cinnamyl) 4 grasped two gas-I2-crown , N_(cinnamyl), azapine, seven crowns, _5 ether, N,N-di(cinnamyl)-4,1〇-diaza-15_crown·5•ether, N_(4vinylbenzyl) _4 -12-crown-4-ether, N,Nc_(4_vinyl nodal)·4,1 diazepine·12_crown<ether, Ν-(4-vinylbenzyl)_4_nitrogen Hetero-15-crown_5·ether, anthracene, fluorene-di-(4-vinylbenzyl)-4,1〇-diaza-15·crown_5_ether, ν, -:-(1-Propyloxyethyl)-4,10-diaza-indole-5-crown-5-ether, N-(l-acryloxyethylethylaza-14-crown-4 -趟, ν_(2-pentenoate ethyl ester) ice aza·18_crown_6_ether and ν,ν·bis-(2-pentenoate) _4,14-diaza--18- Crown-6-ether, etc. The azacrown ether derivative (C1) in the present invention can be produced by a usual method, and examples thereof include the following methods: in an organic solvent, in the absence of a catalyst or a catalyst, The substituted azacrown ether is reacted with a dentate alkyl group having a polymerizable unsaturated double bond. Examples of the organic solvent include a nitrile-based organic solvent (acetonitrile, propionitrile, benzonitrile, etc.). , ketone organic solvents (acetone and methyl ethyl ketone, etc.), amide amine organic solvents (guanamine, acetamide, dimethyl decylamine and dimethyl hydrazine) Amines, etc., ether-based organic solvents (dimethyl ether, tetrahydrofuran, dioxane, etc.), ester-based organic solvents (ethyl acetate and diethyl maleate, etc.), sulfur-containing organic solvents (dithiopyrene) Dimethyl sulfoxide and Cyclohexane, etc.), halogenated hydrocarbons (such as gas and dioxane), hydrocarbons (hexane, heptane, toluene, diphenylbenzene, etc.) and mixtures of two or more of these solvents. 24 201203678 Catalyst For example, metal oxynitrides (such as hydrazine hydroxide, sodium hydroxide, and hydrazine), metal carbonates (sodium bicarbonate, hydrogencarbonate, carbonic acid, carbonic acid, etc.) and alkali metal hydrides ( Sodium hydride, potassium hydride, etc.). The reaction temperature is usually 1 Torr. (: ~150 ° C, the reaction time is usually 0.5 hours to 24 hours. After the reaction is completed, the catalyst can be neutralized as needed, treated with an adsorbent to remove the catalyst and purified. Polymerizable unsaturated double bonds Examples of the halogenated alkyl group include 4-bromo-2-butenoic acid methyl ester, 4-chloro-2-butenoic acid ester, and 1-bromo-4-cyano- 2-butyl group (l-bromo-4-cyano-2-butene), 1-gas-4-cyano-2-butene, chloromethyl acrylate, and acrylic acid ,-2-chloroethyl acrylate, _2_bromoethyl acrylate, decyl decyl acrylate, bromo methacrylate, 2-ethyl methacrylate, bromoethyl methacrylate Ester, cinnamyl chloride, cinnamyl bromide, 4-(chloromethyl)styrene and 4-(bromomethyl)styrene. Triazole derivative (C2) Listed: i, 2,3-benzotriazole, 5-methyl-l,2,3-benzotriazole, 5,6-dimercapto-1,2, 3-benzotriazole, 1,2,4-triazole, 3-amino-1,2,4-triazole, 3,5-diamino-1,2,4.triazole, 3- 5--5-methyl_ι,2,4·triazole, 3-amino-5·ethyl-1,2,4-diazole, 3-amino-5-propyl_ι, 2,4 Triazole and 3-amino-5-butyl-1,2,4-triazole, etc. These triazole derivatives are commercially available. Among these triazole derivatives, charge and discharge cycle characteristics In view of the above, the amine compound-1,2,4-trisole is preferred. The secret material of the present invention further contains the compound (4) and the compound (8) 25 201203678 -- A negative electrode protective film forming agent other than A- i (D) By containing the negative electrode protective film forming agent (D) in the electrolytic solution, the stability of the negative electrode protective film is further improved, and the charge/discharge cycle characteristics can be further improved. The negative electrode protective film forming agent (D) can be exemplified by vinylene carbonate (vinylene). Carbonate, fluoroethylenedicarbonate, ethylene carbonate, ethylene sulfite, propylene sulfite, brominated butyrolactone, etc. Among these compounds, from the viewpoint of cycle characteristics In other words, the electrode protective film forming agent (F), the Lewis test (C), the negative electrode protective film forming agent (d), the nonaqueous solvent (H), and the electrolysis in the electrolytic solution of the present invention. The preferred content or concentration of (G) is as follows. The content of the compound (a) as the electrode protective film forming agent (F) is based on the viewpoint of charge and discharge cycle characteristics, battery capacity, and high storage characteristics. The weight of the liquid is preferably 〇.〇1 by weight (wt%)~1〇wt% ' More preferably 〇〇5 wt%~1 wt0/〇. The content of the compound (B) as the electrode protective film forming agent (F) is preferably 0.01% by weight to 1% by weight based on the weight of the electrolytic solution, from the viewpoints of battery capacity, battery output, and charge and discharge cycle characteristics. It is especially good for 〇〇1 wt% ~1 wt%. The content of the Lewis base (C) is preferably from 〇wt% to 10 wt%, more preferably from 0.01 wt% to 10 wt%, from the viewpoints of battery capacity, battery output, and charge and discharge cycle characteristics. 'Youjia is 0·〇5 wt%~ 1 wt%. From the viewpoints of battery capacity, battery output, and charge and discharge cycle characteristics, the content of the negative electrode protective film forming agent (D) is preferably 0 wt% to 5 wt% based on the weight of the electrolytic solution. More preferably, it is wt01 wt%~5 wt%, and particularly preferably 0.01 wt%~3 wt%. The content of the nonaqueous solvent (H) is preferably from 7 〇 wt% to 99 wt ° / 〇, particularly preferably from 93 wt% to 99 wt%, based on the weight of the battery and the charge and discharge cycle characteristics. %.
就電池輸出及充放電循環特性的觀點而言,電解液中 的電解質(G)的濃度基於電解液的體積,較佳為0.01 mol/L 〜3 mol/L ’ 尤佳為 0.05 mol/L〜1.5 mol/L。 本發明的電解液可更含有過量充電防止劑、脫水劑及 谷量穩定劑等添加劑。 過量充電防止劑可列舉:聯苯(biphenyl)、烷基聯笨 (alkyl biphenyl )、聯三笨(te卬henyl )、聯三苯的部分氫 化物、環己基苯(cyclohexyl benzene)、第三丁基苯及第三 戊基苯等芳香族化合物等。過量充電防止劑的使用量基於 電解液的總重量,通常為〇wt%〜5 wt% ’較佳為〇wt%〜 3 wt%。 脫水劑可列舉沸石(zeolite)、矽膠(silica gel)及氧 化舞等。基於鐘二次電池用電解液的總重量,脫水劑的使 用里通常為〇 wt%〜5 wt%,較佳為0 wt%〜3 wt% 〇 容量穩定劑可列舉:碳酸氟乙二酯、琥珀酸酐、甲 基底咬酮(l-methyl-2-piperidone)、庚烧及氟苯等。基 於電解液的總重量,容量穩定劑的使用量通常為0 wt%〜5 wt% ’ 較佳為 〇 wt%〜3 wt%。 27 201203678 ……*r— 本發明的電解液尤其作為鐘二次電池用的電解液而有 用。 使用本發明的電解液的鐘二次電池是藉由在收納有正 極、負極及分隔片的電池罐内注入本發明的電解液,將電 池罐密封而獲得。 鐘二次電池中的正極可使用以棒式塗佈機等塗佈裝 置,將使正極活性物質、導電劑及黏合劑分散於溶劑中而 衆料化者塗佈於正極用集電體上,加以乾燥而去除溶劑, 視需要利用壓製機進行壓製而成的正極等。 正極活性物質可列舉:鋰與過渡金屬的複合氧化物(例 如 LiCo02、LiNi02、LiMn02 及 LiMn204 等)、過渡金屬氧 化物(例如Mn〇2及V2〇5等)、過渡金屬硫化物(例如m〇S2 及TiS2等)、以及導電性高分子(例如聚苯胺 (polyaniline)、聚偏二氟乙稀(p〇iyvinyHdene f|uoride)、 聚吡咯(polypyrrole)、聚噻吩(;p〇1ythi〇phene)、聚乙炔 (polyacetylene)' 聚對亞苯基(p〇iy_p_phenyiene)及聚口卡 唑(polycarbazole)等)等。 導電劑可列舉:石墨(例如天然石墨及人工石墨等)、 碳黑(carbon black)類(例如碳黑、乙炔黑(acetylene black)、柯琴黑(Ketjen black)、槽黑(channel black)、爐 黑(furnace black)、燈黑(iamp black)及熱黑(thermal black) 等)、金屬粉末(例如is粉及鎳粉等)、導電性金屬氧化物 (例如氧化鋅及氧化鈦等)等。 黏合劑例如可列舉:澱粉、聚偏二氟乙烯、聚乙烯醇 28 201203678 (polyvinyl alcohol )、叛甲基纖維素(carb〇xymethyl cellulose)、聚乙稀基。比 π各 π定酮(p〇iyVinyipyrr〇ud〇ne)、四 氟乙烯(tetrafluoroethylene)、聚乙烯及聚丙烯等高分子化 合物。 溶劑例如可列舉:1-曱基_2_吡咯啶酮、曱基乙基酮、 二曱基曱醯胺、二甲基乙醯胺、N,N_二曱基胺基丙基胺及 四氫吱喃等。 正極用集電體可列舉:鋁、鈦、不鏽鋼、鎳、碳極(b aked carbon)、導電性高分子及導電性玻璃等。 鋰二次電池中,基於正極總重量的正極活性物質、導 電劑及黏合劑的各較佳含量為如下所述。 正極活性物質的含量較佳為7〇 wt%〜98 wt%,尤佳為 9〇Wt%〜98wt%。導電劑的含量較佳為丨wt%〜29wt% : 尤佳為1 wt%〜1〇 wt%。黏合劑的含量較佳為1糾%〜29 wt%,尤佳為 1 wt%〜10 wt〇/。。 、基於正極活性物質、導電劑及黏合劑的總重量,正極 活性物質、導電劑及黏合劑㈣料化時的溶劑使用量較佳 為 20 wt%〜70 Wt%,尤佳為 30 wt%〜6〇 wt〇/〇。 鐘一次電池中的負極可使用以棒式塗佈機等塗佈装 置,將使負極活性物質、導電劑及黏合劑分散於溶劑中而 裝料化者塗佈於負極用集電體上,加以乾燥而去除溶劑, 視需要以壓製機進行壓製而成的負極等。 負極活性物質可列舉:石墨、高分子化合物锻燒體 如將盼樹月曰及吱嚼樹脂等炮燒碳化而成的般燒體)、焦炭類 29 201203678 l. (例如遞青焦炭(Pitch coke)、針狀焦炭(needle c〇ke)及 石油焦炭等)、碳纖維、導電性高分子(例如聚乙炔及聚吡 咯等)、金屬合金(例如鋰-鋁合金、鋰-鋁-錳合金等)等。 導電劑、黏合劑及溶劑可使用與製造正極時所使用的 材料相同的材料。 負極用集電體可列舉:銅、不鏽鋼、鎳、鋁、鈦、碳 極、導電性向分子、導電性玻璃及鋁-鎘合金等。 鐘二次電池中,基於負極總重量的負極活性物質、導 電劑及黏合劑的各較佳含量馬如下所述。 負極活性物質的含量較佳為70 wt%〜98 wt%,尤佳為 90 wt%〜98 wt%。導電劑及黏合劑的含量與正極的情況相 同。 θ負極活性物質、導電劑及黏合劑的漿料化時的溶劑使 用量與正極活性物質、導電劑及黏合劑的漿料化時的溶劑 使用量相同。 鐘二次電池中的分隔片可列舉:聚乙烯、聚丙烯製膜 1微多孔膜;多孔性聚乙稀膜與聚丙烯的多層膜;包含聚 面a纖維、芳族聚醯胺纖維(aramid行ber)、玻璃纖維等的不 織布,以及於其等的表面附著有二氧化梦、氧化鋁、氧化 鈦等陶瓷微粒子的分隔片。 M二次電池中的電池罐可使用不鏽鋼(stainless steel)’鑛有鐵、铭及鎳的鋼等金屬材料,亦可根據電池用 途而使用歸材料。另外,電池罐可根據肢而形成圓筒 型、硬幣型、方型、其他任意的形狀。 201203678 本發明的電解液尤其作為鋰離子電容器用的電解液亦 有用。 使用本發明的電解液的鋰離子電容器是藉由在收納有 正極、負極及分隔片的電容器罐内注入本發明的電解液, 將電容器罐密封而獲得。 鋰離子電容器中的正極可使用以棒式塗佈機等塗佈裝 置,將使活性碳(正極活性物質)、導電劑及黏合劑分散於 溶劑中而漿料化者塗佈於正極用集t體上,加以乾燥而去 除溶劑,視需要利用壓製機進行壓製而成的正極等。 導電劑、黏合劑、溶劑及正極用集電體可列舉與鋰二 次電池的情況相同者。 ' 鐘離子電谷器中,基於正極總重量的正極活性物質、 導電劑及黏合劑的各較佳含量為如下所述。 正極活性物質的含量較佳為70 wt%〜98 wt%,尤佳為 9〇 Wt%〜98 wt%。導電劑的含量較佳為1 wt%〜29 wt〇/0, 尤佳為1 wt%〜10 wt%。黏合劑的含量較佳為i wt%〜^ wt% ’ 尤佳為 1 wt%〜1〇 wt%。 基於正極活性物質、導電劑及黏合劑的總重量,正極 活性物質、導電劑及黏合劑的漿料化時的溶劑使用量較佳 為 20 wt%〜7〇 wt%,尤佳為 3〇 wt%〜6〇 wt〇/〇。 鐘離子電谷器中的負極可使用以棒式塗佈機等塗佈裝 置,將使負極活性物質、導電劑及黏合劑分散於溶劑中而 漿料化者塗佈於負極㈣f體上,加以乾燥而去除溶劑, 視需要利用壓製機進行壓製而成的負極等。 201203678 負極活1*生物質可列舉··非晶碳(am〇rph〇us carb〇n)、 石墨(graphite)、錫及其合金、矽及其合金等。 導電劑、黏合劑及溶劑可使用與製造正極時所使用的 材料相同的材料。 . 負極用集電體可列舉:銅、不鏽鋼、鎳、紹、鈦、碳 極、導電性高分子、導電性朗域,合金等。 鋰離子電容器中’基於負極總重量的負極活性物質、 導電劑及黏合劑的各較佳含量為如下所述。 負極活性物質的含量較佳為70 wt%〜98 wt%,尤佳為 90 wt%〜98 Wt%。導電劑雜合劑的含量與正極的情況相 同。 負極活性物質、導電劑及黏合劑的漿料化時的溶劑使 用量與正極雜物質、導電劑及黏合獅料化時的溶 使用量相同。 鋰離子電容器中的分隔片可列舉:聚乙烯、聚丙烯靠 膜的微多孔膜;多孔性聚乙烯膜與聚丙烯的多層膜;包$ 聚酯纖維、芳族聚醯胺纖維、玻璃纖維等的不織布;以^ 於其等的表續著有二氧化♦、氧她、氧化鈦等 粒子的分隔片。 1 鋰離子電容器中的電池罐可使用不鏽鋼,鍍有鐵、金 及鎳的鋼等金屬材料,亦可根據電池用途而使用塑膠和 料。另外,電池罐可根據用途而形成圓筒型、硬、卞 型、其他任意的形狀。 本發明的電極保護膜形成劑(F)可添加、含有於齒 32 201203678 --人電池或轉子電容㈣正極及/或貞極巾而使用。 眺ΐ加於正Μ的料刊舉如下妓等:於使正極、、壬 ^亟保護膜形成劑(F),以棒式塗佈機等塗佈裝置二 機上,加以乾燥而去除溶劑,視需要利用壓製 添加於負極中的方法可列舉如 性物質、導電劑及黏合劑分散於溶劑中而活 負極用集電體ί ▲式塗佈機等塗佈裝置塗佈於 機進行壓製。乾燥而去除溶劑,視需要利用壓製 就充放電循環特性、電池 言,添加於正性的觀點而 加量基於正_性物質,齡為(U wt%lT (。以的添 為 〇·5 wt%〜5 wt°/〇。 0 1〇 wt/〇,尤佳 就充放電循環特性、電池 言,添加於負極中的情況的電極保f 性的觀點而 加量基於負極活性物質,較佳為〇T:t。添 為 0.5 wt%〜5 wt%。 · wt/°〜10 wt%,尤佳 [實例] 以下,利用實例對本發明進一牛 並不限定於該些實例。以下,朗,但本發明 [路易斯驗(C)的合成]π里份。 〈製造例1〉 33 201203678 ^ 1 N,N-二-(2- 丁烯酸曱酯)_4,i〇_ 二氮雜·ΐ5_ 冠 _5·醚 (ΑΖ-1 )的合成: 於安裝有攪拌機、溫度計及冷卻管的燒瓶中,加入 4,10_二氮雜-15-冠-5-醚[東京化成工業(股)製造]061份 (2.8 mmol份)、4-溴-2-丁烯酸甲酯[東京化成工業(股) 製造]1份(5.6 mmol份)及乙腈1〇份,一邊攪拌一邊使 其均勻溶解,然後於攪拌下在室溫下反應24小時。於減壓 (10 mmHg)下去除乙腈後’利用以丙酮為溶劑的氧化鋁 管柱[150 mesh,Brockman 1,標準級,Aldrich (股)製造] 將反應物純化,獲得N,N-二-(2-丁烯酸曱酯)_4,1〇-二氮雜 -15-冠-5-趟(AZ-1) 0.85 份(2.0 mmol 份)(產率 71%)。 (AZ-1)是通式(2)中,R2為亞曱基,Qi及q2為氫原子, Q3為曱氧基羰基且具有聚合性不飽和雙鍵的取代基鍵結 於氮原子上的二氮雜冠醚化合物。 〈製造例2〉 N,N-j^-(1_丙烯醯氧基乙基)_4,1〇_二氮雜_15冠-5•醚 (AZ-2)的合成: 除了代替4-溴-2-丁烯酸曱酯1份而使用丙烯酸_2_氣 乙酯[東京化成工業(股)製造]0.76份(5.6 mmol份)以 外,以與製造例i相同的方式獲得N,N-二_(卜丙烯醯氧基 乙基)-4,1〇-二氮雜_15_冠_5·醚(az-2) 〇.6〇 份(1.9 mmol 份)(產率68%)。 此外,當將4-溴-2-丁烯酸曱酯1份變更為丙烯酸_2· 氣乙酯0.76份時,以反應成分的莫耳比及非反應成分(溶 34 201203678 劑等)的重量比成為與製造例1的情況同等的方式調整各 原料的量而進行操作。對以下的製造例3亦同樣進行。 (ΑΖ-2)是丙烯醯氧基乙基作為具有聚合性不飽和雙 鍵的取代基而鍵結於氮原子上的二氮雜冠醚化合物。 〈製造例3〉 ^_,队二肉桂基-4,10-二氮雜-15-冠-5-喊(八2-3)的合成: 除了代替4-溴-2-丁烯酸曱酯1份而使用肉桂基氯[東 京化成工業(股)製造]0.85份(5.6 mmol份)以外,以與 製造例1相同的方式獲得N,N-二肉桂基-4,10-二氮雜-15- 冠-5-醚(C1-3 )0_92 份(2.0 mmol 份)(產率 73%)。( AZ-3 ) 是通式(2)中,R2為亞曱基,Q1及Q2為氫原子,q3為 苯基且具有聚合性不飽和雙鍵的取代基鍵結於氮原子上的 一氮雜冠趟化合物。 〈實例1〉 二乙二醇二(2-丁烯酸曱酯)醚(B-1)的合成: 於安裝有攪拌機、溫度計及冷卻管的燒瓶中,加入二 乙二醇[東京化成工業(股)製造]7.26份(68.4 mmol份)、 4_溴-2-丁烯酸曱酯[東京化成工業(股)製造]26.9份(15〇 3 mmol份)、氫氧化鈉6.00份(150 mmol份)及甲苯1〇〇 份,一邊攪拌一邊使其均勻溶解後,於室溫下攪拌15分 鐘,然後添加四丁基溴化銨1·32份(4.1 mmol份)。升溫 至65°C後,攪拌4小時,進行醚化反應。放置冷卻後,添 加水200份,分離水層。進而將有機層以水2〇〇份加以清 洗。藉由減壓(10 mmHg)而去除曱苯後,利用以己烧為 35 201203678 溶劑的氧化铭管柱[150 mesh,Brockman 1,標準級,Aldrich (股)製造]將反應物純化,獲得二乙二醇二(2-丁烯酸曱 西旨)謎(B-1 ) 15.5 份(51·3 mmol 份)(產率 75%) 〈實例2〉 —乙.一碎·一(4_乙稀基卞基)謎(B-2)的合成. 除了代替4-溴-2-丁烯酸甲酯26.9份(150.3 mmol份) 而使用4-乙烯基苄基氣[東京化成工業(股)製造]22.9份 (150.3 mmol份)以外,以與實例1相同的方式獲得二乙 二醇二(4_乙烯基节基)_( B-2 ) 16.9份(49.9 mmol份)(產 率 73%)。 〈實例3〉 1,4-雙(1-丙烯氧基曱基)環己烷(A-1)的合成: 於安裝有攪拌機、溫度計及冷卻管的燒瓶中,加入1,4-環己烷二曱醇[東京化成工業(股)製造]9.86份(68.4 mmol 份)、氯丙烯[東京化成工業(股)製造]11.51份(150.3 mmol 份)、氳氧化鈉6.00份(150 mmol份)及曱苯1〇〇份,一 邊攪拌一邊使其均勻溶解後,於室溫下攪拌15分鐘,然後 添加四丁基溴化敍1.32份(4.1 mmol份)。以2小時升溫 至65°C,進而攪拌4小時,進行醚化反應及重排反應。放 置冷卻後,添加水200份,分離水層。進而將有機層以水 200份加以清洗。藉由減壓(10 mmHg)而去除曱苯後, 利用以己烧為溶劑的氧化銘管柱[150 mesh,Brockman 1, 標準級,Aldrich (股)製造]將反應物純化,獲得ι,4-雙(ι_ 丙婦氧基甲基)環己烧(八-1)10_9份(48.6 111111〇1份)(產 36 201203678 率 71%) 〇 此外’表1〜表3中記載的化合物(a)中的ι,4-雙(乙 烯氧基甲基)環已烷、1,4-丁二醇二乙烯醚及三乙二醇二乙 稀_是使用束售品[Nippon Carbide Industries (股)製造]。 [電解液的製備] 〈實例4〜實例35〉 以表1〜表3所示的重量比例來調配化合物(a)、化 合物(B)、路易斯鹼(C)、負極保護膜形成劑(D)及非 水溶劑(H) ’於其中以成為1 mol/L的濃度的方式溶解 LiPF0來調整實例4〜實例35的電解液。 〈比較例1> 於碳酸乙二酯與碳酸二乙酯的混合溶劑(體積比率 3 : 7)中,使LiPF6以1 mol/L的比例溶解後,以2 wt%的 比例混合碳酸亞乙烯酯,來調整比較例1的電解液。 〈比較例2〉 於碳酸乙二酯與碳酸二曱酯的混合溶劑(體積比率 1 : 2)中,使LiPF6以1 m〇i/L的比例溶解後,以成為0.1 mol/L的方式混合二甲基礙,來調整比較例2的電解液。 〈比較例3〉 於碳酸乙二酯與碳酸二曱酯的混合溶劑(體積比率 1 : 1)中’使LiPF6以1 mol/L的比例溶解後,以5 wt%的 比例混合1,3-丙烷磺内酯,來調整比較例3的電解液。 37 201203678 J-a寸α 卜 ε 【1<】 實例13 1 d 1 1 1 S 〇 (N 〇 1 1 1 1 1 1 實例12 没 d 1 1 1 S 〇 〇 1 1 I 1 實例11 1 1 1 〇 〇 CN d 1 1 (N 1 實例10 s ο 1 1 1 S 〇 tN d 1 1 (N 1 1實例9 s d 1 < f S d f 1 1 (N 1 實例8 1 1 1 1 S 〇 CN 〇 1 1 CS 1 例7」 1 1 1 S 〇 S 〇 (N 〇 1 1 (S 1 實例6 1 1 S 〇 1 〇 d <N 〇 1 1 CN 1 實例5 1 S d 1 1 ο d (N d 1 1 (N 1 [實例4 s d 1 1 1 s d (N 〇 1 1 CN 1 化合物名 1,‘雙(1-丙烯氧基甲基)環己 烧 Μ-雙(1-乙烯氧基甲基)環己 烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲酯)醚 二乙二醇二(4-乙烯基节基)醚 (AZ-l) (AZ-2) (AZ-3) 3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-曱基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-*** 3-胺基-5-丁基-1,2,4-*** 碳酸亞乙烯酯 γ-丁内酯 γ-戊内酯 化合物(A) (份) 化合物(B) (份) 路易斯鹼(c) (份) 負極保護膜形成劑(D) (份) *πχν °°ε 201203678 47.73 1 47.73 1 46.78 1 47.75 1 47.93 1 47.78 1 47.73 1 47.73 • 47.73 1 47.73 1 δ-戊内酯 碳酸乙二酯 碳酸二乙酯 碳酸二甲酯 碳酸乙基曱酯 LiPF6 電解質(mol/L) 201203678 玄寸卜卜卜ε t(N<〕 S d 1 1 S 〇 1 (Ν 〇 1 I 1 1 1 1 ^Τ) ο ο 1 1 S 〇 1 CN 〇 1 1 1 1 1 1 實例 22 s d 1 1 S 〇 <Ν d 1 〇 1 1 1 1 1 rN 實例 21 s o 1 1 S 〇 1 1 1 1 1 1 1 rs 没 o 1 I S 〇 1 1 1 t 1 1 1 (N 實例| J9_ s d 1 1 S 〇 1 <N d 1 1 1 1 1 1 CN 實例| 18___ s o 1 1 S 〇 CN Ο 1 1 1 1 1 1 1 (N 實例 17 s d 1 1 S d cs ο 1 1 1 1 1 1 1 <N 實例; J6__ s o 1 1 S d <Ν| ο 1 1 1 1 1 1 1 <N 實例 J5_ s o 1 1 s ο CN Ο 1 1 1 t 1 1 1 (N 拉2; s d 1 1 s d cs d 1 1 1 1 1 1 1 iN 化合物名 1 1,4-雙(1-丙烯氧基甲基)環1 己院 1,4-雙(1-乙烯氧基甲基)環| 己烧 i 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2· 丁烯酸曱酯) 醚 二乙二醇二(4-乙烯基苄基) |醚 (AZ-l) (AZ-2) (AZ-3) 3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-曱基-1,2,4-*** 1 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-*** 3-胺基-5-丁基-1,2,4-*** 碳酸亞乙烯酯 成分 |ί 化合物(Β) (份) 路易斯鹼(c) (份) 負極保護膜形成劑 (D) (份) 0寸 201203678 1 I 47.63 1 r—Η 1 ! 47.63 1 1 47.63 1 1 47.83 1 1 47.83 1 1 47.73 1 97.73 1 1 1 97.73 1 1 1 〇 1 1 69.73 〇 1 67.73 1 〇 67.73 1 1 γ-丁内酯 γ-戊内酯 δ-戊内酯 碳酸乙二酯 碳酸二乙酯 碳酸二甲酯 碳酸乙基甲酯 LiPF6 ML· \^y 電解質(mol/L) 201203678 J'a寸α 卜 ε 【ε^】 駟ίί! S 〇 1 1 1 1 S 〇 tN d 1 1 1 1 1 1 1 1 S 〇 1 1 1 CN 〇 〇 1 CN d 1 1 1 1 1 ^ 5λ S 〇 1 1 1 <N 〇 1 <N 〇 1 1 1 (S ? 駟Ρ! 〇 〇 1 1 1 t 1 <N d 1 1 1 CS S d 1 1 1 ( S 〇 fN 〇 1 1 1 (N s d 1 1 1 s d 1 1 1 1 ίΝ s o 1 1 1 s d 1 1 1 1 駟?3 s o 1 1 1 s d 1 s o 1 1 1 CN s d 1 1 1 S d 1 CN 〇 1 1 (S s d 1 1 1 s d 1 (N 〇 I 1 1 CS 革 s d 1 1 s d 1 d 1 1 d 1 1 CN 化合物名 1,4-雙(1-丙烯氧基甲基)環己 烧 1,4-雙(1-乙烯氧基甲基)環己 烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲酯) 謎 二乙二醇二(4-乙烯基苄基) 謎 (AZ-l) (AZ-2) (AZ-3) 3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-甲基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-*** 3-胺基-5-丁基-1,2,4-*** 1 碳酸亞乙烯酯 成分 1 化合物(A) (份) 化合物(B) (份) 路易斯鹼(C) (份) 被5 S^ 201203678 J-a寸αζ,ε 1 1 1 49.73 1 1 1 1 49.73 1 1 1 1 47.55 1 1 1 1 47.75 1 ««Η 1 1 1 47.73 1 1 1 1 46.93 1 1 1 1 47.83 1 1 1 1 47.88 1 1 1 1 47.63 1 1 1 1 47.63 1 1 1 1 47.63 1 γ-丁内酯 γ_戊内酯 δ-戊内酯 碳酸乙二酯 碳酸二乙酯 碳酸二甲酯 碳酸乙基曱酯 1 LiPF6 電 解 (mol/L)The concentration of the electrolyte (G) in the electrolyte is preferably 0.01 mol/L to 3 mol/L', and particularly preferably 0.05 mol/L, from the viewpoint of battery output and charge and discharge cycle characteristics. 1.5 mol/L. The electrolytic solution of the present invention may further contain an additive such as an excessive charge preventing agent, a dehydrating agent, and a bar stabilizer. Examples of the overcharge preventing agent include biphenyl, alkyl biphenyl, te卬henyl, a partial hydride of diphenyl, cyclohexyl benzene, and third butyl. An aromatic compound such as benzene or tripentylbenzene. The amount of the overcharge preventing agent used is usually 〇wt% to 5 wt%', preferably 〇wt% to 3 wt%, based on the total weight of the electrolyte. Examples of the dehydrating agent include zeolite, silica gel, and oxidative dance. The dehydrating agent is usually used in an amount of from 〇wt% to 5 wt%, preferably from 0 wt% to 3 wt%, based on the total weight of the electrolyte for the secondary battery, and may be exemplified by fluoroethylene glycol ester, Succinic anhydride, l-methyl-2-piperidone, heptane and fluorobenzene. The capacity stabilizer is usually used in an amount of from 0 wt% to 5 wt%, based on the total weight of the electrolyte, preferably from 〇 wt% to 3 wt%. 27 201203678 ......*r The electrolytic solution of the present invention is useful particularly as an electrolytic solution for a clock secondary battery. The clock secondary battery using the electrolytic solution of the present invention is obtained by injecting the electrolytic solution of the present invention into a battery can containing a positive electrode, a negative electrode, and a separator to seal the battery can. The positive electrode in the secondary battery can be applied to a positive electrode current collector by dispersing a positive electrode active material, a conductive agent, and a binder in a solvent, using a coating device such as a bar coater. The positive electrode obtained by drying and removing the solvent, if necessary, is pressed by a press. Examples of the positive electrode active material include composite oxides of lithium and transition metals (for example, LiCoO 2 , LiNi 2 , LiMn 2 , and LiMn 204), transition metal oxides (for example, Mn 〇 2 and V 2 〇 5, etc.), and transition metal sulfides (for example, m 〇). S2 and TiS2, etc., and conductive polymers (such as polyaniline, polyvinylidene fluoride (p〇iyviny Hdene f|uoride), polypyrrole, polythiophene (; p〇1ythi〇phene) , polyacetylene (polyphenylene) (p〇iy_p_phenyiene) and polycarbazole (polycarbazole), etc. Examples of the conductive agent include graphite (for example, natural graphite and artificial graphite) and carbon black (for example, carbon black, acetylene black, Ketjen black, channel black, and the like). Furnace black, iamp black, and thermal black, metal powder (such as is powder and nickel powder), conductive metal oxide (such as zinc oxide and titanium oxide), etc. . Examples of the binder include starch, polyvinylidene fluoride, polyvinyl alcohol 28 201203678 (polyvinyl alcohol), carb〇xymethyl cellulose, and polyethylene. A polymer compound such as π π hexanone (p〇iyVinyipyrr〇ud〇ne), tetrafluoroethylene, polyethylene, or polypropylene. Examples of the solvent include 1-mercapto-2-pyrrolidinone, mercaptoethyl ketone, decyl decylamine, dimethylacetamide, N,N-didecylaminopropylamine, and four. Hydrogen oxime and so on. Examples of the current collector for the positive electrode include aluminum, titanium, stainless steel, nickel, carbonized carbon, conductive polymer, and conductive glass. In the lithium secondary battery, preferred contents of the positive electrode active material, the conductive agent and the binder based on the total weight of the positive electrode are as follows. The content of the positive electrode active material is preferably from 7 〇 wt% to 98 wt%, particularly preferably from 9 〇 Wt% to 98 wt%. The content of the conductive agent is preferably 丨wt% to 29% by weight: more preferably 1% by weight to 1% by weight. The content of the binder is preferably from 1% to 29% by weight, particularly preferably from 1% by weight to 10% by weight. . Based on the total weight of the positive electrode active material, the conductive agent and the binder, the positive electrode active material, the conductive agent and the binder (4) are preferably used in an amount of 20 wt% to 70 Wt%, more preferably 30 wt%. 6〇wt〇/〇. In the negative electrode in the primary battery, a coating device such as a bar coater can be used, and the negative electrode active material, the conductive agent, and the binder are dispersed in a solvent, and the charge is applied to the current collector for the negative electrode. The anode is dried by removing the solvent, and if necessary, pressing it by a press. Examples of the negative electrode active material include graphite and a polymer compound calcined body, such as a calcined carbon obtained by calcination of a mixture of a mixture of a mixture of a mixture of a mixture of a mixture and a resin, and a coke. 29 201203678 l. (for example, Pitch coke) ), needle coke (needle c〇ke) and petroleum coke, etc., carbon fiber, conductive polymer (such as polyacetylene and polypyrrole), metal alloy (such as lithium-aluminum alloy, lithium-aluminum-manganese alloy, etc.) Wait. As the conductive agent, the binder, and the solvent, the same materials as those used in the production of the positive electrode can be used. Examples of the current collector for the negative electrode include copper, stainless steel, nickel, aluminum, titanium, carbon, conductive molecular, conductive glass, and aluminum-cadmium alloy. In the secondary battery, the preferred content of the negative electrode active material, the conductive agent and the binder based on the total weight of the negative electrode is as follows. The content of the negative electrode active material is preferably from 70 wt% to 98 wt%, particularly preferably from 90 wt% to 98 wt%. The content of the conductive agent and the binder is the same as that of the positive electrode. The solvent used in the slurrying of the θ negative electrode active material, the conductive agent, and the binder is the same as the solvent used in the slurrying of the positive electrode active material, the conductive agent, and the binder. The separator in the secondary battery can be exemplified by a film of a polyethylene, a polypropylene film, a microporous film, a multilayer film of a porous polyethylene film and a polypropylene, and a polyaluminum fiber, an aramid fiber (aramid). A non-woven fabric such as ber) or glass fiber, and a separator having ceramic fine particles such as oxidized dream, alumina, or titanium oxide adhered to the surface thereof. The battery can in the secondary battery of M can be made of stainless steel (stainless steel), metal materials such as iron, nickel, and nickel, and can be used depending on the battery. Further, the battery can can be formed into a cylindrical shape, a coin shape, a square shape, or any other shape depending on the limb. 201203678 The electrolyte of the present invention is also useful as an electrolyte for lithium ion capacitors. The lithium ion capacitor using the electrolytic solution of the present invention is obtained by injecting the electrolytic solution of the present invention into a capacitor can containing a positive electrode, a negative electrode, and a separator to seal the capacitor can. In the positive electrode of the lithium ion capacitor, a coating device such as a bar coater can be used, and the activated carbon (positive electrode active material), the conductive agent, and the binder are dispersed in a solvent, and the slurry is applied to the positive electrode set. The body is dried, and the solvent is removed, and a positive electrode or the like which is pressed by a press as needed is used. The conductive agent, the binder, the solvent, and the current collector for the positive electrode are the same as those in the case of the lithium secondary battery. In the bell ion grid, the preferred content of the positive electrode active material, the conductive agent and the binder based on the total weight of the positive electrode is as follows. The content of the positive electrode active material is preferably from 70 wt% to 98 wt%, particularly preferably from 9 〇 Wt% to 98 wt%. The content of the conductive agent is preferably from 1 wt% to 29 wt〇/0, particularly preferably from 1 wt% to 10 wt%. The content of the binder is preferably i wt% to ^ wt% ', particularly preferably 1 wt% to 1 〇 wt%. The solvent used in the slurrying of the positive electrode active material, the conductive agent, and the binder is preferably 20 wt% to 7 wt%, more preferably 3 wt%, based on the total weight of the positive electrode active material, the conductive agent, and the binder. %~6〇wt〇/〇. The negative electrode in the ion-electric grid can be applied to a negative electrode (four) body by using a coating device such as a bar coater, and the negative electrode active material, the conductive agent, and the binder are dispersed in a solvent. The anode is dried by removing the solvent, and if necessary, pressing it by a press. 201203678 Negative activity 1* biomass can be exemplified by amorphous carbon (am〇rph〇us carb〇n), graphite (graphite), tin and its alloys, niobium and its alloys. As the conductive agent, the binder, and the solvent, the same materials as those used in the production of the positive electrode can be used. Examples of the current collector for the negative electrode include copper, stainless steel, nickel, samarium, titanium, carbon, conductive polymer, conductive domain, and alloy. In the lithium ion capacitor, the preferred contents of the negative electrode active material, the conductive agent and the binder based on the total weight of the negative electrode are as follows. The content of the negative electrode active material is preferably from 70 wt% to 98 wt%, particularly preferably from 90 wt% to 98 wt%. The content of the conductive agent hybrid is the same as that of the positive electrode. The amount of the solvent used in the slurrying of the negative electrode active material, the conductive agent, and the binder is the same as that of the positive electrode dopant, the conductive agent, and the binder. Examples of the separator in the lithium ion capacitor include a microporous film of polyethylene and polypropylene, a multilayer film of a porous polyethylene film and polypropylene, and a polyester fiber, an aromatic polyamide fiber, a glass fiber, and the like. Non-woven fabric; a sheet containing particles such as oxidized x, oxygen, titanium oxide, etc., continued to be used. 1 The battery can in the lithium ion capacitor can be made of stainless steel, metal such as iron, gold, or nickel, or plastic or plastic depending on the battery. Further, the battery can can be formed into a cylindrical shape, a hard shape, a 卞 type, or any other shape depending on the application. The electrode protective film forming agent (F) of the present invention can be added and contained in the tooth 32 201203678 - a human battery or a rotor capacitor (four) positive electrode and/or a blemish. The material to be added to the main product is as follows: the positive electrode, the protective film forming agent (F), and the coating device such as a bar coater are dried and the solvent is removed. The method of adding the negative electrode to the negative electrode as needed may be, for example, a chemical substance, a conductive agent, and a binder dispersed in a solvent, and a live negative electrode is applied to a machine by a coating device such as a current collector or a ▲ coater. Drying and removing the solvent, if necessary, using charging to charge and discharge cycle characteristics, the battery is added to the positive point of view and the amount is based on the positive-positive substance, and the age is (U wt% lT (. The addition is 〇·5 wt %1~5 wt°/〇. 0 1〇wt/〇, particularly preferably, the charge/discharge cycle characteristics and the battery are added to the negative electrode active material, and the amount is based on the negative electrode active material. 〇T: t. The addition is 0.5 wt% to 5 wt%. · wt/° to 10 wt%, especially good [Examples] Hereinafter, the present invention is not limited to these examples by way of example. The present invention [synthesis of Lewis test (C)] π aliquot. <Production Example 1> 33 201203678 ^ 1 N,N-di-(2-decyl decanoate) _4, i〇_ diazepine ΐ 5_ crown Synthesis of _5·ether (ΑΖ-1): 4,10-diaza-15-crown-5-ether was added to a flask equipped with a stirrer, a thermometer and a cooling tube [manufactured by Tokyo Chemical Industry Co., Ltd.] 061 parts (2.8 mmol parts), methyl 4-bromo-2-butenoate [manufactured by Tokyo Chemical Industry Co., Ltd.] 1 part (5.6 mmol part) and 1 part acetonitrile, and uniformly dissolved while stirring Then, it was reacted under stirring for 24 hours at room temperature. After removing acetonitrile under reduced pressure (10 mmHg), 'Using acetone as a solvent for alumina column [150 mesh, Brockman 1, standard grade, manufactured by Aldrich) The reaction was purified to obtain N,N-di-(2-butenoate)- 4,1 〇-diaza-15-crown-5-oxime (AZ-1) 0.85 parts (2.0 mmol) ( Yield 71%). (AZ-1) is a substituent bond of the formula (2) wherein R2 is a fluorenylene group, Qi and q2 are a hydrogen atom, and Q3 is a fluorenyloxycarbonyl group and has a polymerizable unsaturated double bond. A diazacrown ether compound attached to a nitrogen atom. <Production Example 2> N, Nj^-(1_acryloxyethyl)_4,1〇_diaza--15 crown-5•ether (AZ Synthesis of -2): In place of 1 part of 4-bromo-2-butenoic acid ester, 0.76 parts (5.6 mmol parts) of 2-ethyl acrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) was used in addition to In the same manner as in Production Example i, N,N-di-(dipropenyloxyethyl)-4,1〇-diaza-15_crown-5 ether (az-2) 〇.6 〇 (( 1.9 mmol part) (yield 68%). In addition, when 1 part of 4-bromo-2-butenoate was changed to acrylic acid ········· In the case of 6 parts, the weight ratio of the molar ratio of the reaction component and the non-reactive component (solvent 34 201203678, etc.) was adjusted to adjust the amount of each raw material in the same manner as in the case of Production Example 1. The following Production Example 3 was carried out. The same goes for it. (ΑΖ-2) is a diazepane ether compound in which an acryloxyethyl group is bonded to a nitrogen atom as a substituent having a polymerizable unsaturated double bond. <Manufacturing Example 3> ^_, the synthesis of the group 2 cinnamyl-4,10-diaza-15-crown-5- shouting (eight 2-3): except for the substitution of 4-bromo-2-butenoate N,N-dicinnamyl-4,10-diaza- was obtained in the same manner as in Production Example 1, except that 0.8 parts (5.6 mmol) of cinnamyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used. 15-crown-5-ether (C1-3) 0-92 parts (2.0 mmol) (yield: 73%). (AZ-3) is a nitrogen in the formula (2) wherein R2 is a fluorenylene group, Q1 and Q2 are a hydrogen atom, q3 is a phenyl group, and a substituent having a polymerizable unsaturated double bond is bonded to a nitrogen atom. Mixed crown compound. <Example 1> Synthesis of diethylene glycol bis(2-butenoate) ether (B-1): Diethylene glycol was added to a flask equipped with a stirrer, a thermometer, and a cooling tube [Tokyo Chemical Industry Co., Ltd. ( Manufacture] 7.26 parts (68.4 mmol parts), 4-bromo-2-butenoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 26.9 parts (15〇3 mmol), sodium hydroxide 6.00 parts (150 mmol) The mixture and 1 part of toluene were uniformly dissolved while stirring, and then stirred at room temperature for 15 minutes, and then 1.32 parts (4.1 mmol) of tetrabutylammonium bromide was added. After raising the temperature to 65 ° C, the mixture was stirred for 4 hours to carry out an etherification reaction. After standing to cool, 200 parts of water was added and the aqueous layer was separated. Further, the organic layer was washed with 2 parts of water. After the benzene was removed by decompression (10 mmHg), the reaction was purified by oxidizing the column [150 mesh, Brockman 1, standard grade, manufactured by Aldrich) with a solvent of 35 201203678. Ethylene glycol bis(2-butene citrate) mystery (B-1) 15.5 parts (51·3 mmol) (yield 75%) <Example 2> - B. One broken · One (4_B Synthesis of the dilute thiol) mystery (B-2). In addition to 26.9 parts (150.3 mmol) of methyl 4-bromo-2-butenoate, 4-vinylbenzyl gas was used [Tokyo Chemical Industry Co., Ltd.) In the same manner as in Example 1, except that 22.9 parts (150.3 mmol parts), diethylene glycol bis(4-vinylphenyl)-(B-2) 16.9 parts (49.9 mmol parts) was obtained (yield 73%) ). <Example 3> Synthesis of 1,4-bis(1-propenyloxyindenyl)cyclohexane (A-1): In a flask equipped with a stirrer, a thermometer and a cooling tube, 1,4-cyclohexane was added. Didecyl alcohol [manufactured by Tokyo Chemical Industry Co., Ltd.] 9.86 parts (68.4 mmol parts), chloropropene [manufactured by Tokyo Chemical Industry Co., Ltd.] 11.51 parts (150.3 mmol parts), sodium bismuth oxide 6.00 parts (150 mmol parts) and 1 part of toluene was dissolved in a homogeneous manner while stirring, and then stirred at room temperature for 15 minutes, and then 1.32 parts (4.1 mmol) of tetrabutyl bromide was added. The temperature was raised to 65 ° C over 2 hours, and further stirred for 4 hours to carry out an etherification reaction and a rearrangement reaction. After the cooling was allowed to stand, 200 parts of water was added, and the aqueous layer was separated. Further, the organic layer was washed with 200 parts of water. After the benzene was removed by decompression (10 mmHg), the reaction was purified by oxidizing the column [150 mesh, Brockman 1, standard grade, manufactured by Aldrich) using hexane as a solvent to obtain ι, 4 - bis (ι_ propyl ethoxymethyl) cyclohexan (8-1) 10_9 parts (48.6 111111 〇 1 part) (production 36 201203678 rate 71%) 〇 In addition to the compounds described in Table 1 to Table 3 (a i,4-bis(vinyloxymethyl)cyclohexane, 1,4-butanediol divinyl ether and triethylene glycol diethylene in the use of bundles [Nippon Carbide Industries (shares) Manufacturing]. [Preparation of Electrolyte Solution] <Example 4 to Example 35> The compound (a), the compound (B), the Lewis base (C), and the negative electrode protective film forming agent (D) were blended in the weight ratios shown in Tables 1 to 3. The electrolyte solution of Example 4 to Example 35 was adjusted by dissolving LiPF0 in a non-aqueous solvent (H)' at a concentration of 1 mol/L. <Comparative Example 1> In a mixed solvent of ethylene carbonate and diethyl carbonate (volume ratio 3:7), LiPF6 was dissolved at a ratio of 1 mol/L, and then vinylene carbonate was mixed at a ratio of 2 wt%. The electrolytic solution of Comparative Example 1 was adjusted. <Comparative Example 2> In a mixed solvent of ethylene carbonate and dinonyl carbonate (volume ratio: 1:1), LiPF6 was dissolved at a ratio of 1 m〇i/L, and then mixed at 0.1 mol/L. The electrolyte of Comparative Example 2 was adjusted by dimethyl group. <Comparative Example 3> In a mixed solvent of ethylene carbonate and dinonyl carbonate (volume ratio 1:1), 'LiPF6 was dissolved at a ratio of 1 mol/L, and then mixed at a ratio of 5 wt%. Propane sultone was used to adjust the electrolytic solution of Comparative Example 3. 37 201203678 Ja inch α 卜 ε [1<] Example 13 1 d 1 1 1 S 〇(N 〇1 1 1 1 1 1 Example 12 no d 1 1 1 S 〇〇1 1 I 1 Example 11 1 1 1 〇〇 CN d 1 1 (N 1 instance 10 s ο 1 1 1 S 〇tN d 1 1 (N 1 1 instance 9 sd 1 < f S df 1 1 (N 1 instance 8 1 1 1 1 S 〇CN 〇1 1 CS 1 Example 7" 1 1 1 S 〇S 〇 (N 〇1 1 (S 1 Example 6 1 1 S 〇1 〇d <N 〇1 1 CN 1 Example 5 1 S d 1 1 ο d (N d 1 1 (N 1 [Example 4 sd 1 1 1 sd (N 〇1 1 CN 1 compound name 1, 'bis(1-propenyloxymethyl)cyclohexanium bismuth-bis(1-vinyloxymethyl) ring) Hexane 1,4-butanediol divinyl ether triethylene glycol divinyl ether diethylene glycol bis(2-butenoic acid methyl ester) ether diethylene glycol bis(4-vinyl benzyl) ether (AZ -l) (AZ-2) (AZ-3) 3-Amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-oxime 1,2-,4-triazole 3-amino-5-ethyl-1,2,4-triazole 3-amino-5-propyl-1,2,4-triazole 3-amino -5-butyl-1,2,4-triazole vinylene carbonate γ-butyrolactone γ-valerolactone (A) (part) Compound (B) (part) Lewis base (c) (part) Negative electrode protective film forming agent (D) (part) *πχν °° ε 201203678 47.73 1 47.73 1 46.78 1 47.75 1 47.93 1 47.78 1 47.73 1 47.73 • 47.73 1 47.73 1 δ-valerolactone ethylene carbonate diethyl carbonate diethyl carbonate dimethyl carbonate ethyl phthalate LiPF6 electrolyte (mol/L) 201203678 玄卜卜卜 ε t(N< d 1 1 S 〇1 (Ν I1 I 1 1 1 1 ^Τ) ο ο 1 1 S 〇1 CN 〇1 1 1 1 1 1 Example 22 sd 1 1 S 〇<Ν d 1 〇1 1 1 1 1 rN Example 21 so 1 1 S 〇1 1 1 1 1 1 1 rs no o 1 IS 〇1 1 1 t 1 1 1 (N instance | J9_ sd 1 1 S 〇1 <N d 1 1 1 1 1 1 CN instance | 18___ so 1 1 S 〇CN Ο 1 1 1 1 1 1 1 (N instance 17 sd 1 1 S d cs ο 1 1 1 1 1 1 1 <N instance; J6__ so 1 1 S d <Ν | ο 1 1 1 1 1 1 1 <N Example J5_ so 1 1 s ο CN Ο 1 1 1 t 1 1 1 (N pull 2; sd 1 1 sd cs d 1 1 1 1 1 1 1 iN Compound name 1 1,4-bis(1-propenyloxymethyl) )) Ring 1 1,4- 1,4-bis(1-vinyloxymethyl) ring | hexene i 1,4-butanediol divinyl ether triethylene glycol divinyl ether diethylene glycol di(2· Ethyl crotonate) Ether diethylene glycol bis(4-vinylbenzyl) | Ether (AZ-l) (AZ-2) (AZ-3) 3-Amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-mercapto-1,2,4-triazole 1 3-amino-5-ethyl-1,2,4 - Triazole 3-Amino-5-propyl-1,2,4-triazole 3-Amino-5-butyl-1,2,4-triazole vinylene carbonate component | ί Compound (Β) (Part) Lewis base (c) (part) Negative electrode protective film forming agent (D) (part) 0 inch 201203678 1 I 47.63 1 r-Η 1 ! 47.63 1 1 47.63 1 1 47.83 1 1 47.83 1 1 47.73 1 97.73 1 1 1 97.73 1 1 1 〇1 1 69.73 〇1 67.73 1 〇67.73 1 1 γ-butyrolactone γ-valerolactone δ-valerolactone ethylene carbonate diethyl ester diethyl carbonate dimethyl carbonate ethyl methyl carbonate LiPF6 ML· \^y Electrolyte (mol/L) 201203678 J'a inch α Bu ε [ε^] 驷ίί! S 〇1 1 1 1 S 〇tN d 1 1 1 1 1 1 1 1 S 〇1 1 1 CN 〇〇1 CN d 1 1 1 1 1 ^ 5λ S 〇1 1 1 <N 〇1 <N 〇1 1 1 (S ? 驷Ρ! 〇〇1 1 1 t 1 <N d 1 1 1 CS S d 1 1 1 ( S 〇fN 〇1 1 1 (N sd 1 1 1 sd 1 1 1 1 ίΝ so 1 1 1 sd 1 1 1 1 驷? 3 so 1 1 1 sd 1 so 1 1 1 CN sd 1 1 1 S d 1 CN 〇1 1 (S sd 1 1 1 sd 1 (N 〇I 1 1 CS leather sd 1 1 sd 1 d 1 1 d 1 1 CN Compound name 1,4-bis(1-propenyloxymethyl)cyclohexene 1,4-bis(1-vinyloxymethyl)cyclohexane 1,4-butanediol divinyl ether triethylene Alcohol Divinyl Ether Diethylene Glycol Di(2-Methyl Butyrate) Enigmatic Diethylene Glycol Di(4-vinylbenzyl) Enigma (AZ-l) (AZ-2) (AZ-3) 3- Amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-methyl-1,2,4-triazole 3-amino group- 5-ethyl-1,2,4-triazole 3-amino-5-propyl-1,2,4-triazole 3-amino-5-butyl-1,2,4-triazole 1 Vinylene carbonate component 1 Compound (A) (part) Compound (B) (part) Lewis base (C) (part) by 5 S^ 201203678 Ja inch αζ, ε 1 1 1 49.73 1 1 1 1 49.73 1 1 1 1 47.55 1 1 1 1 47.75 1 ««Η 1 1 1 47.73 1 1 1 1 46.93 1 1 1 1 47.83 1 1 1 1 47.88 1 1 1 1 47.63 1 1 1 1 47.63 1 1 1 1 47.63 1 γ-丁内Ester γ-valerolactone δ-valerolactone ethylene carbonate diethyl carbonate carbonate Yue carbonate, ethyl carbonate ester 1 LiPF6 electrolyte (mol / L)
201203678 ^ L201203678 ^ L
[鋰離子電池用正極的製作] 基於表4〜表7所示的配方’利用以下方法製成添加 有電極保護膜形成劑(F)的正極。 將LiCo〇2粉末90.0份、柯琴黑[Aldrich公司製造]5 份、聚偏二氟乙烯[Aldrich公司製造]5份、及表4〜表7 所示重量的電極保護膜形成劑(F)於研缽中充分混合後, 添加1-曱基-2-β比略咬酮[東京化成工業(股)製造]〇份, 進而於研缽中充分混合而獲得漿料。將所得的漿料於大氣 中使用線棒來塗佈於厚度20 μιη的紹電解箱上的單面,於 100°C下乾燥15分鐘後,進而於減壓下(1〇mmHg)在8(rc 下乾燥5分鐘,衝壓為15.95 mm(p,製作實例36〜實例67 的鋰離子電池用正極。 [鋰離子電池用負極的製作] 基於表4〜表7所示的配方,利用以下方法製成添加 有電極保護膜形成劑(F)的負極。 將平均粒徑約8 μιη〜12 μιη的石墨粉末92.5份、聚偏 二氟乙稀7.5份、1·甲基_2_0比咯啶酮[東京化成工業(股) 製造]200份及表4〜表7所示重量的電極保護膜形成劑(ρ) 於研缽中充分混合而獲得漿料。將所得的漿料塗佈於厚度 20卜111的鋼箔的單面,於1〇〇。(:下乾燥15分鐘而使溶劑蒸 發後’衝壓為16.15 mmcp,利用壓製機形成厚度30 , 製作實例36〜實例67的鋰離子電池用負極。 [鋰離子電容器用正極的製作] 基於表7所示的配方,利用以下方法製成添加有電極 44 201203678 保護膜形成劑(F)的正極。 將活性碳粉末90.0份、柯琴黑[Aldrich公司製造]5.0 份、聚偏二氟乙浠[Aldrich公司製造]5.0份、及表4〜表7 所示重量的電極保護膜形成劑(F)於研缽中充分混合後, 添加1-甲基-2-吡咯啶酮[東京化成工業(股)製造]7〇 〇份, 進而於研蛛中充分混合而獲得漿料。將所得的漿料於大氣 中使用線棒來塗佈於厚度2〇 μιη的铭電解箔上的單面,於 100C下乾燥15分鐘後,進而減壓下(1〇 mmHg)在8〇。〇 下乾燥5分鐘,衝壓為15.95 mmcp ’製作實例68〜實例71 的鋰離子電容器用正極。 [鋰離子電容器用負極的製作] 基於表7所示的配方,利用以下方法製成添加有電極 保護膜形成劑(F)的負極。 將平均粒徑約8 μιη〜12 μιη的石墨粉末92.5份、聚偏 二氟乙烯7.5份、1-曱基_2·吡咯啶酮[東京化成工業(股) 製造]200份及表4〜表7所示重量的電極保護膜形成劑(F) 於研缽中充分混合而獲得漿料。將所得的漿料塗佈於厚度 2〇从111的銅箔的單面,於1〇〇。〇下乾燥15分鐘而使溶劑^ 發後,衝壓為16.15 mnup,利用壓製機形成厚度3〇 μιη。、 將所得的電極、及鋰金屬箔以分隔片(聚丙烯製不織布) 失持而設置於燒杯單元,使負極理論容量的約75%的鋰離 子以約10小時吸藏於負極中,製作實例68〜實例71的鋰 離子電容器用負極。 ^ 〈比較例4〉 45 201203678 除了代替電極保護膜形成劑(F)而添加曱基颯1.5份 以外’以與實例36〜實例67相同的方法製成比較例4的 鋰離子電池用正極。 除了不添加電極保護膜形成劑(F)以外,以與實例 36〜實例67相同的方法製成比較例4的鋰離子電池用負 極0 〈比較例5〉 除了代替電極保護膜形成劑(F)而添加1,3-丙烷磺内 醋1.5份以外’以與實例36〜實例67相同的方法製成比 較例5的鋰離子電池用正極。 除了不添加電極保護膜形成劑(F)以外,以與實例 36〜實例67相同的方法製成比較例5的鋰離子電池用負 極。 〈比較例6〉 除了代替電極保護膜形成劑(F)而添加二曱基颯1.5 份以外,以與實例68〜實例71相同的方法製成比較例6 的鐘離子電容器用正極。 除了不添加電極保護膜形成劑(F)以外,以與實例 68〜實例71相同的方法製成比較例6的鋰離子電容器用負 〇 〈比較例7〉 除了代替電極保護膜形成劑(F)而添加1,3-丙烷磺内 醋15份以外,以與實例68〜實例71相同的方法製成比 較例7的鋰離子電容器用正極。 46 201203678 除了不添加電極保護膜形成劑(F)以外,以與實例 68〜實例71相同的方法製成比較例7的鋰離子電容器用負 極0 47 201203678 J-a寸卜卜卜ε 【寸<】 實例44 1 1 1 1 1 1 1 1 1 in 1 1 1 1 1 1 實例43 1 1 1 1 1 1 1 yn 1 1 1 1 1 1 實例42 狐想 1 1 1 1 1 1 1 Ό 1 1 1 1 1 1 實例41 卿(想 1 1 1 1 1 1 t 1 1 1 1 1 1 實例40 1 »〇 1 1 1 1 1 1 in 1 1 in 1 1 1 1 1 實例39 柳C璁 1 *〇 1 1 1 1 1 1 1 1 1 1 1 1 1 1 實例38 ζ缌 1 V) 1 1 1 1 t 1 1 ΙΓ) 1 1 1 1 1 1 1 實例37 1 1 1 1 1 1 1 1 v-j > 1 1 I 1 1 1 實例36 卿:缌 1 1 1 1 1 1 1 Μ璁 W-ϊ 1 1 1 1 1 1 1 化合物名 電極 1,4-雙(1-丙烯氧基甲基) 環己烷 1,4-雙(1-乙烯氧基甲基) 環己烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲 醋)謎 二乙二醇二(4-乙烯基苄 基)醚 (ΑΖ-1) (AZ-2) 1 (AZ-3) 3-胺基-1,2,4**** 3,5-二胺基-1,2,4-*** 3-胺基-5-甲基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-*** 3-胺基-5-丁基-1,2,4-*** 成分 化合物(A) (份) 化合物(B) (份) 路易斯鹼 (c) (份) 8寸 201203678 J-a寸卜卜l>e 實例53 1 1 in 1 1 1 1 Η想 1 1 1 1 t 實例52 棚C邀 1 IT) 1 1 1 1 1 1 1 1 1 實例51 1 1 1 1 1 1 1 1 1 1 1 實例50 郷ζ璁 1 »—Η 1 1 1 1 1 irj 1 1 1 1 1 實例49 ζ鸡 1 1 1 1 1 1 … 1 1 1 實例48 C锶 1 1 1 1 1 <i^ 1 r Η 1 1 1 實例47 1 1 1 1 1 1 in 1 1 1 實例46 1 1 1 1 1 Μ缌 1 1 1 1 實例45 m. ig 1 1 1 1 1 1 1 1 1 1 化合物名 想 鮮1 1,4-雙(1-丙烯氧基甲基) 環己烷 1,4-雙(1-乙烯氧基甲基) 環己烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲 酯)醚 二乙二醇二(4-乙烯基苄 基)醚 (AZ-1) (AZ-2) (AZ-3) 3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-曱基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-二α坐 3-胺基-5-丁基-1,2,4-*** 成分 化合物(A) (份) 化合物(Β) (份) 路易斯鹼 (C) (份) 6寸 201203678 J-a寸卜/,卜rn 【9<】 實例62 1 1 1 1 d 1 1 1 I 1 1 1 1 1 Θ想 1 1 1 1 1 1 1 1 1 1 1 1 實例61 C想 1 1 1 1 1 1 VO 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1實例60 1 棚C邀 1 1 1 ( 1 1 ( 1 1 1 1 in 1 1 1 1 1 1 1 1 1 1 1 實例59 <5Κ ^ 1 1 1 1 1 1 1 1 1 1 1 1 i〇 1 1 1 1 1 1 1 1 1 1 1 實例58 ζ锶 1 1 1 1 1 1 1 1 1 1 1 ^Ti 1 1 1 1 1 1 1 1 1 1 1 實例57 1 1 1 1 1 1 1 1 1 1 1 *rj 1 1 1 1 1 1 1 1 1 1 1 實例56 卿;埵 1 1 1 1 1 1 1 1 1 1 1 V) 1 1 1 1 1 1 1 1 1 1 1 實例55 1 1 1 1 1 1 1 1 1 1 1 1 Η璁 1 1 1 1 1 1 1 1 1 I 1 實例54 職璁 1 1 1 1 1 1 1 1 1 1 1 1 4璁 in 1 1 1 1 1 1 1 1 1 1 1 I 化合物名 電極 1,4-雙(1-丙烯氧基甲基) 環己烷 1 1,4-雙(1-乙烯氧基甲基) 環己烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲 酯)醚 二乙二醇二(4-乙烯基苄 基)醚 (AZ-1) (AZ-2) (AZ-3) 丨3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-甲基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4·*** 3-胺基-5-丁基-1,2,4·*** 成分 化合物(A) (份) 化合物(B) (份) 路易斯鹼 (C) (份)[Production of Positive Electrode for Lithium Ion Battery] The positive electrode to which the electrode protective film forming agent (F) was added was produced by the following method based on the formulation shown in Tables 4 to 7. 90.0 parts of LiCo〇2 powder, 5 parts of Keqin black [manufactured by Aldrich], polyvinylidene fluoride [manufactured by Aldrich] 5 parts, and electrode protective film forming agent (F) shown in Tables 4 to 7 After thoroughly mixing in a mortar, a 1-mercapto-2-β ketone ketone [manufactured by Tokyo Chemical Industry Co., Ltd.] was added, and further mixed in a mortar to obtain a slurry. The obtained slurry was applied to a single surface of a 20 μm thick electrolysis box in the atmosphere using a wire bar, and dried at 100 ° C for 15 minutes, and further under reduced pressure (1 〇 mmHg) at 8 ( The rc was dried for 5 minutes and punched to 15.95 mm (p, the positive electrode for the lithium ion battery of Example 36 to Example 67. [Production of negative electrode for lithium ion battery] Based on the formulations shown in Tables 4 to 7, the following method was used. A negative electrode to which an electrode protective film forming agent (F) is added. 92.5 parts of graphite powder having an average particle diameter of about 8 μm to 12 μm, 7.5 parts of polyvinylidene fluoride, and 1·methyl-2_0-pyrrolidone [ Manufactured by Tokyo Chemical Industry Co., Ltd.] 200 parts and the electrode protective film forming agent (ρ) having the weights shown in Tables 4 to 7 were thoroughly mixed in a mortar to obtain a slurry. The obtained slurry was applied to a thickness of 20 One side of the steel foil of 111 was placed at 1 Torr. (: After drying for 15 minutes to evaporate the solvent, 'pressing was 16.15 mmcp, and a thickness of 30 was formed by a press machine, and a negative electrode for a lithium ion battery of Examples 36 to 67 was produced. [Preparation of positive electrode for lithium ion capacitor] Based on the formulation shown in Table 7, the following method was used. Electrode 44 201203678 The positive electrode of the protective film forming agent (F) was added. 90.0 parts of activated carbon powder, 5.0 parts of Keqin black [manufactured by Aldrich], polyvinylidene fluoride (made by Aldrich) 5.0 parts, and a table After the electrode protective film forming agent (F) having the weight shown in Table 7 and Table 7 was sufficiently mixed in a mortar, 7 parts of 1-methyl-2-pyrrolidone [manufactured by Tokyo Chemical Industry Co., Ltd.] was added, and further The slurry was thoroughly mixed with a spider to obtain a slurry, and the obtained slurry was applied to a single surface of an electrolytic foil having a thickness of 2 μm by using a wire rod in the air, dried at 100 C for 15 minutes, and then decompressed. The lower (1〇mmHg) was dried at 8 〇. The underside was dried for 5 minutes and punched to 15.95 mmcp. The positive electrode for the lithium ion capacitor of Example 68 to Example 71 was fabricated. [Production of Negative Electrode for Lithium Ion Capacitor] Based on the formulation shown in Table 7. A negative electrode to which the electrode protective film forming agent (F) was added was produced by the following method: 92.5 parts of graphite powder having an average particle diameter of about 8 μm to 12 μm, 7.5 parts of polyvinylidene fluoride, and 1-mercapto-2. Pyrrolidone [Made in Tokyo Chemical Industry Co., Ltd.] 200 parts and Table 4 to Table 7 The electrode protective film forming agent (F) was thoroughly mixed in a mortar to obtain a slurry, and the obtained slurry was applied to one side of a copper foil having a thickness of 2 Å from 111 to 1 Torr. After the solvent was applied, it was punched to 16.15 mnup, and a thickness of 3 μm was formed by a press machine. The obtained electrode and the lithium metal foil were placed in a beaker unit with a separator (polypropylene non-woven fabric), and the negative electrode was placed. About 75% of the theoretical capacity of lithium ions was absorbed in the negative electrode for about 10 hours, and the negative electrode for lithium ion capacitors of Examples 68 to 71 was produced. <Comparative Example 4> 45 201203678 A positive electrode for a lithium ion battery of Comparative Example 4 was produced in the same manner as in Example 36 to Example 67 except that 1.5 parts of fluorenyl hydrazine was added instead of the electrode protective film forming agent (F). A negative electrode for a lithium ion battery of Comparative Example 4 was produced in the same manner as in Examples 36 to 67 except that the electrode protective film forming agent (F) was not added. <Comparative Example 5> In place of the electrode protective film forming agent (F) Further, a positive electrode for a lithium ion battery of Comparative Example 5 was produced in the same manner as in Example 36 to Example 67 except that 1.5 parts of 1,3-propane sulphuric acid was added. The negative electrode for a lithium ion battery of Comparative Example 5 was produced in the same manner as in Example 36 to Example 67 except that the electrode protective film forming agent (F) was not added. <Comparative Example 6> A positive electrode for a bell ion capacitor of Comparative Example 6 was produced in the same manner as in Example 68 to Example 71 except that 1.5 parts of a fluorenyl hydrazine was added instead of the electrode protective film forming agent (F). A negative electrode for a lithium ion capacitor of Comparative Example 6 was prepared in the same manner as in Examples 68 to 71 except that the electrode protective film forming agent (F) was not added. <Comparative Example 7> In place of the electrode protective film forming agent (F) A positive electrode for a lithium ion capacitor of Comparative Example 7 was produced in the same manner as in Example 68 to Example 71 except that 15 parts of 1,3-propane sulphuric acid was added. 46 201203678 A negative electrode for a lithium ion capacitor of Comparative Example 7 was produced in the same manner as in Example 68 to Example 71 except that the electrode protective film forming agent (F) was not added. 0 47 201203678 Ja inch Bub ε [inch < Example 44 1 1 1 1 1 1 1 1 1 in 1 1 1 1 1 1 Example 43 1 1 1 1 1 1 1 yn 1 1 1 1 1 1 Example 42 Fox 1 1 1 1 1 1 1 Ό 1 1 1 1 1 1 Example 41 Qing (Think 1 1 1 1 1 1 t 1 1 1 1 1 1 Example 40 1 »〇1 1 1 1 1 1 in 1 1 in 1 1 1 1 1 Example 39 Liu C璁1 *〇1 1 1 1 1 1 1 1 1 1 1 1 1 1 Example 38 ζ缌1 V) 1 1 1 1 t 1 1 ΙΓ) 1 1 1 1 1 1 1 Example 37 1 1 1 1 1 1 1 1 vj > 1 1 I 1 1 1 Example 36 Qing: 缌1 1 1 1 1 1 1 Μ璁W-ϊ 1 1 1 1 1 1 1 Compound name electrode 1,4-bis(1-propenyloxymethyl)cyclohexane 1, 4-bis(1-vinyloxymethyl)cyclohexane 1,4-butanediol divinyl ether triethylene glycol divinyl ether diethylene glycol di(2-butenoic acid methyl vinegar) enigma two alcohol Bis(4-vinylbenzyl)ether (ΑΖ-1) (AZ-2) 1 (AZ-3) 3-Amino-1,2,4*triazole 3,5-diamino-1,2 ,4-triazole 3-amino-5-methyl-1,2,4-triazole 3-amino-5-ethyl-1,2,4-triazole 3-amino-5-propyl -1,2,4-triazole 3-amino-5-butyl-1,2,4-triazole component compound (A) (part) Compound (B) (part) Lewis base (c) (part) 8 inch 201203678 Ja inch Bu Bu l>e Example 53 1 1 in 1 1 1 1 Η想1 1 1 1 t Example 52 shed C invite 1 IT) 1 1 1 1 1 1 1 1 1 Example 51 1 1 1 1 1 1 1 1 1 1 1 Example 50 郷ζ璁1 »—Η 1 1 1 1 1 irj 1 1 1 1 1 Example 49 ζ chicken 1 1 1 1 1 1 ... 1 1 1 Example 48 C锶1 1 1 1 1 < ;i^ 1 r Η 1 1 1 Example 47 1 1 1 1 1 1 in 1 1 1 Example 46 1 1 1 1 1 Μ缌1 1 1 1 Example 45 m. ig 1 1 1 1 1 1 1 1 1 1 Compound 1 1,4-bis(1-propenyloxymethyl)cyclohexane 1,4-bis(1-vinyloxymethyl)cyclohexane 1, 4-butanediol divinyl ether triethylene glycol divinyl ether diethylene glycol bis(2-methylbutenoate) ether diethylene glycol bis(4-vinylbenzyl) ether (AZ-1) ( AZ-2) (AZ-3) 3-amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-mercapto-1, 2,4-triazole 3-amino-5-ethyl-1,2,4-triazole 3-amino-5-propyl-1,2,4-di-α-sodium 3-amino-5- Butyl-1,2,4-triazole component compound (A) (part) Compound (Β) (part) Lewis base (C) (part) 6 inch 201203678 Ja inch / / rn [9 <] Example 62 1 1 1 1 d 1 1 1 I 1 1 1 1 1 1想1 1 1 1 1 1 1 1 1 1 1 1 Example 61 C想1 1 1 1 1 1 VO 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Example 60 1 Shed C invites 1 1 1 ( 1 1 ( 1 1 1 1 in 1 1 1 1 1 1 1 1 1 1 1 Example 59 < 5Κ ^ 1 1 1 1 1 1 1 1 1 1 1 1 i〇1 1 1 1 1 1 1 1 1 1 1 Example 58 ζ锶1 1 1 1 1 1 1 1 1 1 1 ^Ti 1 1 1 1 1 1 1 1 1 1 1 Example 57 1 1 1 1 1 1 1 1 1 1 1 *rj 1 1 1 1 1 1 1 1 1 1 1 Example 56 埵;埵1 1 1 1 1 1 1 1 1 1 1 V) 1 1 1 1 1 1 1 1 1 1 1 Example 55 1 1 1 1 1 1 1 1 1 1 1 1 Η璁1 1 1 1 1 1 1 1 1 I 1 Example 54 Job 1 1 1 1 1 1 1 1 1 1 1 1 4璁in 1 1 1 1 1 1 1 1 1 1 1 I Compound name Electrode 1,4-bis(1-propenyloxymethyl)cyclohexane 1 1,4-bis(1-vinyloxymethyl)cyclohexane 1,4-butanediol divinyl ether triethylene glycol Divinyl ether diethylene glycol bis(2-methylbutanoate) ether diethylene glycol bis(4-vinylbenzyl)ether (AZ-1) (AZ-2) (AZ-3) 丨3- Amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-methyl-1,2,4-triazole 3-amino group- 5-ethyl-1,2,4-triazole 3-amino-5-propyl-1,2,4·triazole 3-amino-5-butyl-1,2,4·triazole Compound (A) (part) Compound (B) (part) Lewis base (C) (part)
OS 201203678 【卜d JU寸卜卜卜ε 1實例71 1 ΙΓ1 1 1 1 1 1 1 1 Η缉 ir> 1 1 to 1 1 1 1 1 實例70 鄉ζ邀 1 υ-ϊ 1 1 1 1 1 1 1 1 1 1 1 1 1 1 實例69 邀 1 1 1 1 1 1 1 1 i〇 1 1 V) 1 1 1 1 1 實例68 I 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 實例67 I 1 1 1 1 1 1 1 in 1 1 1 < 1 1 1 1 實例66 卿;頌 1 1 1 1 1 1 1 1 W-) 1 1 1 1 1 1 1 < 實例65 ζ邀 1 vn 1 1 1 1 1 1 1 iri 1 1 1 1 1 1 1 1 實例64 <DBC 總 1 1 1 1 1 1 1 1 Θ缌 yn 1 1 1 1 1 1 1 1 實例63 C埤 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 化合物名 電極 1,4-雙(1-丙烯氧基甲基) 環己烷 1,4-雙(1-乙烯氧基甲基) 環己烷 1,4-丁二醇二乙烯醚 三乙二醇二乙烯醚 二乙二醇二(2-丁烯酸甲 酯)醚 二乙二醇二(4-乙烯基苄 基)醚 (AZ-1) (AZ-2) (AZ-3) 3-胺基-1,2,4-*** 3,5-二胺基-1,2,4-*** 3-胺基-5-甲基-1,2,4-*** 3-胺基-5-乙基-1,2,4-*** 3-胺基-5-丙基-1,2,4-*** 3-胺基-5-丁基-1,2,4-*** 成分 化合物(A) (份) 化合物(B) (份) 路易斯鹼 (C) (份) 201203678.OS 201203678 [Bu d JU inch Bub ε 1 instance 71 1 ΙΓ 1 1 1 1 1 1 1 1 Η缉ir> 1 1 to 1 1 1 1 1 Example 70 Township invitation 1 υ-ϊ 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Example 69 Invite 1 1 1 1 1 1 1 1 i〇1 1 V) 1 1 1 1 1 Example 68 I 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Example 67 I 1 1 1 1 1 1 1 in 1 1 1 < 1 1 1 1 Example 66 Qing;颂1 1 1 1 1 1 1 1 W-) 1 1 1 1 1 1 1 < Example 65 ζ invitation 1 vn 1 1 1 1 1 1 1 iri 1 1 1 1 1 1 1 1 Example 64 <DBC Total 1 1 1 1 1 1 1 1 Θ缌yn 1 1 1 1 1 1 1 1 Example 63 C埤1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Compound name electrode 1,4-bis(1-propenyloxymethyl)cyclohexane 1,4-bis(1-vinyloxymethyl)cyclohexane Alkane 1,4-butanediol divinyl ether triethylene glycol divinyl ether diethylene glycol bis(2-butenoic acid methyl ester) ether diethylene glycol bis(4-vinylbenzyl) ether (AZ- 1) (AZ-2) (AZ-3) 3-Amino-1,2,4-triazole 3,5-diamino-1,2,4-triazole 3-amino-5-methyl -1,2,4-three 3-amino-5-ethyl-1,2,4-triazole 3-amino-5-propyl-1,2,4-triazole 3-amino-5-butyl-1,2, 4-triazole component compound (A) (part) Compound (B) (part) Lewis base (C) (part) 201203678.
[鋰離子電池、鋰離子電容器的製作] (1) 鐘離子電池的製作 (1-1)正極的製作 將LiCo〇2粉末9.0份、村琴黑[Aldrich公司製造]〇 5 份及聚偏二氟乙烯[Aldrich公司製造]〇5份於研缽中充分 混合後,添加1-曱基-2-n比咯咬酮[東京化成工業(股)製 造]7.0份,進而於研缽中充分混合而獲得漿料。將所得的 漿料於大氣中使用線棒來塗佈於厚度2〇 μιη的鋁電解箔上 的單面,於l〇〇C下乾燥15分鐘後,進而於減壓下(1〇 mmHg)在80 C下乾燥5分鐘,衝壓為15 95 mrmp,製作 膜厚30 μιη的鋰離子電池用的正極。 U-2)負極的製作 將平均粒徑約8 μιη〜12 μιη的石墨粉末92.5份、聚偏 二氟乙烯7.5份及1-曱基_2_吡咯啶酮[東京化成工業(股) 製造]200份於研缽中充分混合而獲得漿料。將所得的漿料 塗佈於厚度20 μιη的銅箔的單面,於1〇〇。〇下乾燥15分鐘 而使〉谷劑蒸發後,衝壓為16.15 mm(p,利用壓製機形成厚 度30 μιη ’製作鋰離子電池用的負極。 (1-3)二次電池用單元的製作 於2032型硬幣單元内的兩端,將上述正極及 負極以各 自的塗佈面相對的方式配置而製作二次電池用單元。 (2) 鋰離子電容器的製作 (2-1)正極的製作 使用利用鹼活化法而獲得的比表面積約為22〇〇 m2/g 52 201203678 的活性碳作為正極活性物質。將活性碳粉末、 聚偏二氟乙稀分別以重量比成為8〇: 1〇:⑺的比例=及 混合,將該混合物添加於料_彳的_ A轉伽式 攪拌混合而獲得聚料。將該聚料以刮刀‘二中, 叫的減上,暫時乾燥後,以電極尺寸成為20_= 30 二取。電極的厚度約為5〇 μιη mm ,製成•電容器匕 (2-2)負極的製作 將平均粒徑約8 μιη〜12 μ 黑10份、及聚偏二氟乙稀10份混八j末80伤、乙炔 作為溶劑的N_甲基t各姻中_;字=合物添加於 漿料以刮刀法塗佈於厚产18 * D,獲付漿料。將該 以電極尺寸成為2。mm:3。m:二=暫時乾燥後, 約為5〇帅。於單桃喊前,電極的厚度 小時,製成鐘離子電容器用的負^真工中以咖乾燥5 (2-3)於負極中的鋰的摻雜 於以上述方式獲得的負極 中。雜量為負極理論容量=7=、時吸藏於負極 U-4)電容器單元的組裝 於以上述方式獲得的正極鱼 丙職颂朴使(收聚 53 201203678 納箱中並密封,製成鋰離子電容器。 [評價] 電解液的評價 將實例4〜實例35以及比較例1〜比較例3中調整的 電解液分別注入上述二次電池用單元中後密封,以下述方 法來評價高電壓充放電循環特性及高溫保存特性,廿 入電容器單元中後密封,以下述方法來評價高電 且注 循環特性及高溫保存特性,將上述兩種評價妹壓充玫電 中。 示於表8 54 201203678 [表8] 裡離子電池 鋰離子電容器 項目 高電壓循環特性(%) 高溫保存特性 (%) 高電壓循環特性 (%) 高溫保存特性 (%) 實例4 92.0 96.7 88.5 94.2 實例5 89.3 94.9 86.6 93.0 實例6 89.0 94.7 88.2 90.3 實例7 89.6 94.3 86.1 92.0 實例8 87.1 93.6 86.1 90.9 實例9 91.5 94.6 89.0 89.6 實例10 87.9 92.6 83.7 87.7 實例11 90.5 95.6 86.3 90.6 實例12 87.8 92.5 83.2 88.0 實例13 86.9 91.1 85.4 91.0 實例14 90.6 85.4 86.2 83.8 實例15 89.7 84.2 85.1 83.7 實例16 89.4 84.4 87.3 80.0 實例17 88.8 93.6 83.9 89.0 實例18 87.8 92.2 85.5 88.0 實例19 87.7 92.5 83.1 91.8 實例20 86.8 91.2 83.0 89.8 實例21 86.9 91.7 83.1 90.6 實例22 90.8 96.2 90.3 95.4 實例23 90.1 96.5 85.9 91.9 實例24 90.2 96.2 89.9 93.4 實例25 90.1 96.3 85.6 95.3 實例26 90.3 96.1 88.3 93.0 實例27 90.2 96.4 87.2 94.3 實例28 86.9 86.5 83.2 85.8 實例29 86.9 91.8 84.9 88.9 實例30 86.9 91.1 84.2 90.3 實例31 89.4 94.2 85.7 90.9 實例32 89.7 94.7 85.5 93.2 實例33 90.1 95.4 88.9 93.6 實例34 89.5 93.2 88.2 89.1 實例35 88.9 91.9 84.4 89.8 比較例1 50.2 55.9 46.2 53.6 比較例2 71.3 76.7 67.8 75.6 比較例3 76.3 81.6 72.1 78.9 電極的評價 55 201203678 J / / / -τριί (1 )裡二次電池的製作 於2032型硬幣單元内的兩端,將實例36〜實例67以 及比較例4、比較例5的正極及負極以各自的塗佈面相對 的方式配置而製作二次電池用單元。將於碳酸乙二酯與碳 酸二甲酯的混合溶劑(體積比率1:1)中使LiPF6以1 mol/L 的比例溶解而成的電解液注入至所製成的單元中並密封, 將利用以下方法評價高電壓充放電循環特性及高溫保存特 性的結果示於表9中。 (2)鋰離子電容器的製作 於包含層壓膜的收納箱中,將實例68〜實例71以及 比較例6、比較例7的正極及負極以各自的塗佈面相對的 方式配置而製作電容器用單元。將於碳酸乙二酯與碳酸二 曱酯的混合溶劑(體積比率1 : 1)中使LiPF6以1 m〇i/L 的比例溶解而成的電解液注入至所製成的單元中並密封, 將利用以下方法評價高電壓充放電循環特性及高溫保存特 性的結果示於表9中。 56 201203678 [表9] 正極 單元的種類※ 高電壓循環特性(%) 高溫保存特性(%) 實例36 LIB 88.9 91.5 實例37 LIB 88.2 91.1 實例38 LIB 89.6 92.9 實例39 LIB 89.2 91.5 實例40 LIB 88.4 92.2 實例41 LIB 88.6 91.5 實例42 LIB 89.5 91.5 實例43 LIB 89.3 91.4 實例44 LIB 89.3 91.6 實例45 LIB 88.9 91.2 實例46 LIB 83.3 89.7 實例47 LIB 84.7 88.8 實例48 LIB 84.1 90.0 實例49 LIB 84.7 88.9 實例50 LIB 89.0 92.0 實例51 LIB 88.7 92.9 實例52 LIB 89.3 91.5 實例53 LIB 88.1 91.6 實例54 LIB 88.0 92.8 實例55 LIB 89.4 91.4 實例56 LIB 88.5 91.3 實例57 LIB 88.1 91.8 實例58 LIB 89.2 91.6 實例59 LIB 88.9 91.1 實例60 LIB 89.0 92.9 實例61 LIB 91.1 93.2 實例62 LIB 84.1 89.2 實例63 LIB 83.4 88.4 實例64 LIB 84.5 89.8 實例65 LIB 83.3 88.8 實例66 LIB 84.9 89.7 實例67 LIB 83.9 89.0 實例68 LIC 88.8 91.4 實例69 LIC 87.2 90.0 實例70 LIC 83.2 89.5 實例71 LIC 83.8 89.9 比較例4 LIB 49.3 55.1 比較例5 LIB 70.9 76.0 比較例6 LIC 45.4 53.1 比較例7 LIC 46.0 53.2 ※:LIB (鋰離子電池),LIC (鋰離子電容器) 57 201203678 ^ / / /*tpif 〈高電壓紐電循環軸 使用充放電測定裝置「[Production of Lithium Ion Battery and Lithium Ion Capacitor] (1) Preparation of a Clock Ion Battery (1-1) Preparation of a positive electrode 9.0 parts of LiCo〇2 powder, 5 parts of Murakami [made by Aldrich], and 2 pieces of polyethylene 5 parts of fluoroethylene [manufactured by Aldrich Co., Ltd.] was thoroughly mixed in a mortar, and then 7.0 parts of 1-mercapto-2-n ratio ketamine [manufactured by Tokyo Chemical Industry Co., Ltd.] was added, and further mixed in a mortar. And the slurry is obtained. The obtained slurry was applied to a single surface of an aluminum electrolytic foil having a thickness of 2 μm by using a wire bar in the air, dried at 10 ° C for 15 minutes, and further under reduced pressure (1 〇 mmHg). It was dried at 80 C for 5 minutes, and punched into 15 95 mrmp to prepare a positive electrode for a lithium ion battery having a film thickness of 30 μm. U-2) Preparation of a negative electrode 92.5 parts of graphite powder having an average particle diameter of about 8 μm to 12 μm, 7.5 parts of polyvinylidene fluoride, and 1-mercapto-2-pyrrolidinone [Made in Tokyo Chemical Industry Co., Ltd.] 200 parts were thoroughly mixed in a mortar to obtain a slurry. The obtained slurry was applied to one side of a copper foil having a thickness of 20 μm at 1 Torr. After drying under the arm for 15 minutes, the varnish was evaporated, and the film was punched to 16.15 mm (p, and a thickness of 30 μm was formed by a press to prepare a negative electrode for a lithium ion battery. (1-3) Production of a secondary battery unit at 2032 In the both ends of the coin unit, the positive electrode and the negative electrode are disposed so that the respective coated surfaces face each other to form a secondary battery unit. (2) Production of a lithium ion capacitor (2-1) Preparation of a positive electrode using a base The activated carbon obtained by the activation method has a specific surface area of about 22 〇〇m 2 /g 52 201203678 as a positive electrode active material. The activated carbon powder and polyvinylidene fluoride are respectively made into a weight ratio of 8 〇: 1 〇: (7) Proportion = and mixing, the mixture is added to the _ A gamma-type stirring mixing of the material _ 而 to obtain a granule. The granule is reduced by the squeegee 'two, the temporary drying, and the electrode size becomes 20 _ = 30. The thickness of the electrode is about 5 〇μιη mm, and the negative electrode made of capacitor 匕(2-2) has an average particle size of about 8 μm~12 μ black, 10 parts, and polyvinylidene fluoride. Part of the mixed eight j end 80 wounds, acetylene as a solvent N_methyl t in each marriage _; word = combined The material was added to the slurry and applied to a thick product of 18 * D by a doctor blade method to obtain a slurry. The electrode size was 2. mm: 3. m: two = after temporary drying, it was about 5 〇 handsome. Before the peach screams, the thickness of the electrode is small, and the negative electrode is made into a negative electrode for the plasma ion capacitor to dry 5 (2-3) the lithium in the negative electrode to be doped in the negative electrode obtained in the above manner. The theoretical capacity of the negative electrode = 7 =, when occluded in the negative electrode U-4) The assembly of the capacitor unit was carried out in the above-described manner, and the positive electrode was prepared in a container of 2012-03678 and sealed to form a lithium ion capacitor. [Evaluation] Evaluation of the electrolytic solution The electrolytic solutions adjusted in the example 4 to the example 35 and the comparative example 1 to the comparative example 3 were respectively injected into the secondary battery unit, and then sealed, and the high voltage charge and discharge cycle characteristics and the following were evaluated by the following method. The high-temperature storage characteristics are sealed into the capacitor unit and sealed. The high-voltage and cycle-charging characteristics and high-temperature storage characteristics are evaluated by the following methods. The above two evaluations are charged in the furnace. Table 8 54 201203678 [Table 8] Lithium battery lithium ion capacitor project high voltage cycle Ring characteristics (%) High temperature storage characteristics (%) High voltage cycle characteristics (%) High temperature storage characteristics (%) Example 4 92.0 96.7 88.5 94.2 Example 5 89.3 94.9 86.6 93.0 Example 6 89.0 94.7 88.2 90.3 Example 7 89.6 94.3 86.1 92.0 Example 8 87.1 93.6 86.1 90.9 Example 9 91.5 94.6 89.0 89.6 Example 10 87.9 92.6 83.7 87.7 Example 11 90.5 95.6 86.3 90.6 Example 12 87.8 92.5 83.2 88.0 Example 13 86.9 91.1 85.4 91.0 Example 14 90.6 85.4 86.2 83.8 Example 15 89.7 84.2 85.1 83.7 Example 16 89.4 84.4 87.3 80.0 Example 17 88.8 93.6 83.9 89.0 Example 18 87.8 92.2 85.5 88.0 Example 19 87.7 92.5 83.1 91.8 Example 20 86.8 91.2 83.0 89.8 Example 21 86.9 91.7 83.1 90.6 Example 22 90.8 96.2 90.3 95.4 Example 23 90.1 96.5 85.9 91.9 Example 24 90.2 96.2 89.9 93.4 Example 25 90.1 96.3 85.6 95.3 Example 26 90.3 96.1 88.3 93.0 Example 27 90.2 96.4 87.2 94.3 Example 28 86.9 86.5 83.2 85.8 Example 29 86.9 91.8 84.9 88.9 Example 30 86.9 91.1 84.2 90.3 Example 31 89.4 94.2 85.7 90.9 Example 32 89.7 94.7 85.5 93.2 Example 33 90.1 95.4 88.9 93.6 Example 34 89.5 93 .2 88.2 89.1 Example 35 88.9 91.9 84.4 89.8 Comparative Example 1 50.2 55.9 46.2 53.6 Comparative Example 2 71.3 76.7 67.8 75.6 Comparative Example 3 76.3 81.6 72.1 78.9 Electrode Evaluation 55 201203678 J / / / -τριί (1 ) The positive electrode and the negative electrode of Examples 36 to 67 and Comparative Example 4 and Comparative Example 5 were placed at opposite ends of the 2032 type coin unit, and the secondary battery cells were produced by arranging the positive electrode and the negative electrode facing each other. An electrolyte obtained by dissolving LiPF6 in a ratio of 1 mol/L in a mixed solvent of ethylene carbonate and dimethyl carbonate (volume ratio 1:1) is injected into the produced unit and sealed, and will be utilized. The results of the evaluation of the high voltage charge and discharge cycle characteristics and the high temperature storage characteristics by the following methods are shown in Table 9. (2) Preparation of Lithium Ion Capacitor In the storage case including the laminate film, the positive electrode and the negative electrode of Examples 68 to 71 and Comparative Example 6 and Comparative Example 7 were placed so as to face each other with the coated surface thereof to prepare a capacitor. unit. An electrolyte obtained by dissolving LiPF6 in a ratio of 1 m〇i/L in a mixed solvent of ethylene carbonate and dinonyl carbonate (volume ratio of 1:1) is injected into the prepared unit and sealed. The results of evaluating the high voltage charge and discharge cycle characteristics and the high temperature storage characteristics by the following methods are shown in Table 9. 56 201203678 [Table 9] Types of positive electrode unit ※ High voltage cycle characteristics (%) High temperature storage characteristics (%) Example 36 LIB 88.9 91.5 Example 37 LIB 88.2 91.1 Example 38 LIB 89.6 92.9 Example 39 LIB 89.2 91.5 Example 40 LIB 88.4 92.2 Example 41 LIB 88.6 91.5 Example 42 LIB 89.5 91.5 Example 43 LIB 89.3 91.4 Example 44 LIB 89.3 91.6 Example 45 LIB 88.9 91.2 Example 46 LIB 83.3 89.7 Example 47 LIB 84.7 88.8 Example 48 LIB 84.1 90.0 Example 49 LIB 84.7 88.9 Example 50 LIB 89.0 92.0 Example 51 LIB 88.7 92.9 Example 52 LIB 89.3 91.5 Example 53 LIB 88.1 91.6 Example 54 LIB 88.0 92.8 Example 55 LIB 89.4 91.4 Example 56 LIB 88.5 91.3 Example 57 LIB 88.1 91.8 Example 58 LIB 89.2 91.6 Example 59 LIB 88.9 91.1 Example 60 LIB 89.0 92.9 Example 61 LIB 91.1 93.2 Example 62 LIB 84.1 89.2 Example 63 LIB 83.4 88.4 Example 64 LIB 84.5 89.8 Example 65 LIB 83.3 88.8 Example 66 LIB 84.9 89.7 Example 67 LIB 83.9 89.0 Example 68 LIC 88.8 91.4 Example 69 LIC 87.2 90.0 Example 70 LIC 83.2 89.5 Example 71 LIC 83.8 89.9 Comparative Example 4 LIB 49.3 55.1 Comparison 5 LIB 70.9 76.0 Comparative Example 6 LIC 45.4 53.1 Comparative Example 7 LIC 46.0 53.2 ※: LIB (Lithium Ion Battery), LIC (Lithium Ion Capacitor) 57 201203678 ^ / / /*tpif <High Voltage New Cycle Cycling Shaft Using Charge and Discharge Measurement Device
Tedmica (股)製造],以^池为析儀1470型」[T〇y〇 停頓10分鐘後,以(U c的.,電流充電至電壓4·5 V, 反覆進行該充放電1定此^將電池電壓放電至3.5 V, 第50循環充電時的電缝、^次充電時的電池容量及 性。數值越大,表示充放電:述式算出充放電循環特 电痛%特性越良好。 高電壓充放電循環特性( 電池容量/初次充電時的電池容量)X1QG衣充電時的 〈向‘保存特性的評價〉Tedmica (manufacturing)], using ^池 as the analyzer type 1470"[T〇y〇 pause for 10 minutes, then (U c., current is charged to voltage 4·5 V, repeat the charge and discharge 1 ^The battery voltage is discharged to 3.5 V, the electrical gap at the 50th cycle charge, and the battery capacity and the charge at the time of charge. The larger the value, the more the charge and discharge are: the formula calculates the charge/discharge cycle. High-voltage charge-discharge cycle characteristics (battery capacity/battery capacity at the time of initial charge) Evaluation of the "to-memory characteristics" of X1QG clothes during charging
Tech^=_絲置「電池分㈣1·型」[Toyo Techmca (股)劁 w,,” Λ ^ 土」wyo 容量(初次電池容量)谁而^電至電壓3.5V,測定 ^於坑下^量7)日1而以.1〇的電流充電至電壓“ V,w 存後,以0.1 C的電流進行放電至3.5 •^伴)拉^各4 (高溫保存後電池容量)。由下述式算出 ^皿保存特性。數值越大,表示高溫保存特性越良好。 池容量)2特性⑻=(高溫保存後電池容量/初次電 f產業上之可利用性】 58 201203678 使用本發明的電極保護膜形成劑(F)的電解液由於 高電壓下的循環特性及高溫儲藏穩定性優異,故而尤其作 為鋰二次電池用電解液或鋰離子電容器用電解液而有用, 適合用於電動汽車。 【圖式簡單說明】 無。 【主要元件符號說明】 無0 59Tech^=_Wire set "Battery sub (4) 1 type" [Toyo Techmca (share) 劁 w,," Λ ^ soil" wyo capacity (first battery capacity) who ^ electricity to voltage 3.5V, measured ^ under the pit ^ Quantity 7) Day 1 and charge with a current of .1〇 to the voltage “V, w, then discharge to a current of 0.1 C to 3.5 • ^ with) pull each 4 (battery capacity after high temperature storage). The formula is used to calculate the storage characteristics of the dish. The larger the value, the better the high-temperature storage characteristics. Pool capacity) 2 characteristics (8) = (the battery capacity after high-temperature storage / the initial availability of the industry f) 58 201203678 Using the electrode protection of the present invention Since the electrolyte solution of the film forming agent (F) is excellent in cycle characteristics at high voltage and high-temperature storage stability, it is particularly useful as an electrolyte solution for a lithium secondary battery or an electrolyte solution for a lithium ion capacitor, and is suitable for use in an electric vehicle. Simple description of the schema] None. [Key component symbol description] None 0 59
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CN104737340B (en) * | 2012-11-07 | 2016-12-14 | 三洋化成工业株式会社 | The manufacture method of electrode protective membrane forming agent, electrode, electrolyte, lithium secondary battery, lithium-ion capacitor and electrode protective membrane |
CN106711506A (en) * | 2016-12-22 | 2017-05-24 | 广州天赐高新材料股份有限公司 | Electrolyte containing styrene and derivative thereof and lithium secondary battery using electrolyte |
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JPWO2012111335A1 (en) * | 2011-02-18 | 2014-07-03 | 三洋化成工業株式会社 | Electrode protective film forming agent |
WO2013031045A1 (en) * | 2011-08-26 | 2013-03-07 | 三洋化成工業株式会社 | Additive for electrode, and electrode |
WO2013031487A1 (en) * | 2011-08-26 | 2013-03-07 | 三洋化成工業株式会社 | Additive for negative electrode, negative electrode, method for producing polymerized coating film, lithium secondary battery, and lithium ion capacitor |
KR20160030553A (en) * | 2013-07-12 | 2016-03-18 | 이옥서스, 인크. | Stability enhancing additive for electrochemical devices |
JP6284772B2 (en) * | 2013-08-20 | 2018-02-28 | 三洋化成工業株式会社 | Electrode protective film forming agent |
EP3621134A4 (en) * | 2017-05-01 | 2021-04-14 | Murata Manufacturing Co., Ltd. | Cyclic compound, negative electrode for lithium-ion secondary battery, and lithium-ion secondary battery |
WO2024081666A2 (en) * | 2022-10-10 | 2024-04-18 | Rutgers, The State University Of New Jersey | Solvent compositions for lithium-metal batteries |
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JP2771406B2 (en) * | 1992-11-30 | 1998-07-02 | キヤノン株式会社 | Rechargeable battery |
US5705689A (en) * | 1995-06-19 | 1998-01-06 | Associated Universities, Inc. | Aza compounds as anion receptors |
JPH09251860A (en) * | 1996-03-15 | 1997-09-22 | Fujitsu Ltd | Electrolyte for lithium secondary battery and lithium secondary battery |
JPH11329492A (en) * | 1998-05-12 | 1999-11-30 | Asahi Glass Co Ltd | Secondary power source |
CN1338130A (en) * | 1998-06-08 | 2002-02-27 | 摩尔科技公司 | Multifunctional reactive monomers for safety protection of nonaqueous electrochemical cells |
JP4411691B2 (en) * | 1999-06-30 | 2010-02-10 | パナソニック株式会社 | Non-aqueous electrolyte secondary battery, non-aqueous electrolyte secondary battery charge control system, and equipment using the same |
JP4599639B2 (en) * | 1999-11-22 | 2010-12-15 | 株式会社デンソー | Non-aqueous electrolyte secondary battery |
JP4618404B2 (en) * | 2004-03-08 | 2011-01-26 | 日本電気株式会社 | Non-aqueous electrolyte secondary battery |
JP4285407B2 (en) * | 2005-01-07 | 2009-06-24 | 宇部興産株式会社 | Non-aqueous electrolyte for lithium secondary battery and non-aqueous electrolyte secondary battery |
JP2010500725A (en) * | 2006-08-11 | 2010-01-07 | カリフォルニア インスティテュート オブ テクノロジー | Dissociation agents, formulations and methods resulting in increased solubility of fluoride |
JP5340860B2 (en) * | 2008-09-03 | 2013-11-13 | 三洋化成工業株式会社 | Additive for electrolyte |
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CN106711506A (en) * | 2016-12-22 | 2017-05-24 | 广州天赐高新材料股份有限公司 | Electrolyte containing styrene and derivative thereof and lithium secondary battery using electrolyte |
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