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Title Page

ABSTRACT

Contents

Introduction 23

1.1. Lithium Ion Batteries 23

1.1. Introduction of lithium ion batteries 23

1.2. Safety issue of LIBs 24

2. Ionic Liquids 28

2.1. Introduction of ionic liquids 28

2.2. Species of ionic liquids 29

2.3. Application of ionic liquids 32

2.3.1 Reaction solvent in organic synthesis 32

2.3.2 Lubricants. 36

2.3.3 Electrolytes for LIBs 37

Results and discussion 41

1. Synthesis and Properties of N-alkyl-2-methoxypyrrolinium bis(fluorosulfonyl)imide 41

1.1. Strategy 41

1.2. Preparation 46

1.3. Thermal behaviors 48

1.4. Physical properties 51

1.5. Electrochemical stability 53

1.6. Electrochemical performance 56

1.7. Summary 64

2. Preparation and Properties of Binary Electrolytes 66

2.1. Strategy 66

2.2. Preparation 68

2.3. Flammability test 69

2.4. Physical properties 73

2.5. Electrochemical stability 76

2.6. Electrochemical performance 79

2.7. Summary 85

Conclusions 88

Experimental Details 91

1. General 91

2. General Procedure for the Preparation of the Pyrrolinium-based Ionic Liquids 94

2.1. General procedure for the preparation of N-alkyl-2-pyrrolidinone 94

2.2. General procedure for the preparation of N-alkyl-2-methoxypyrrolinium methyl sulfates 95

2.3. General procedure for the anion metathesis - Preparation of N-alkyl-2-methoxypyrrolinium bis(fluorosulfonyl)imides 97

2.4. Preparation of the binary electrolytes of E(OMe)Pyrl-FSI 99

3. Electrochemical Performance 99

3.1. Preparation of electrode and cell fabrication 99

3.2. Electrochemical characterization 100

REFERENCES 102

APPENDICES 106

초록 127

List of Tables

Table 1. Physical properties of FSI anion based ILs 40

Table 2. Physical properties of pyrrolidinium and piperidinium ionic... 42

Table 3. Preparation of N-alkyl-2-methoxypyrrolinium... 48

Table 4. Thermal behaviors of pyrrolinium-based FSI ionic liquids 49

Table 5. Physical properties of pyrrolinium FSI ionic liquids 52

Table 6. Physical properties of pyrrolinium FSI ionic liquids with 1.0... 53

Table 7. Initial Discharge Capacity and Retention ratio of six... 57

Table 8. Lithium ion transference number of six different electrolytes... 64

Table 9. Flammability Tests (Direct and Indirect Flame) and SET... 72

Table 10. Physical properties of binary electrolytes and ILs with 1.0... 75

Table 11. Initial Discharge Capacity and Retention ratio of six... 84

Table 12. Initial Discharge Capacity and Retention ratio of in eight... 85

List of Figures

Figure 1. Schematics of Lithium ion battery 25

Figure 2. Various species of ionic liquid 31

Figure 3. Wittig reaction in BMIm-PF6(이미지참조) 34

Figure 4. Suzuki coupling in BMIm-BF₄ 35

Figure 5. Diels-Alder reaction in BMIm-BF₄ 36

Figure 6. Molecular structure of IL lubricants 37

Figure 7. Rate properties of various imidazolium-based ILs 39

Figure 8. Electrochemical windows of piperinium-based ILs 43

Figure 9. Electrochemical windows of pyrrolidinium-based ILs 43

Figure 10. Outline of the novel strategy; pyrrolinium-based ionic... 44

Figure 11. Cathodic limit of 6 different electrolytes: E(OMe)Pyrl-... 54

Figure 12. Anodic limit of 6 different electrolytes : E(OMe)Purl-FSI... 54

Figure 13. Cycle performance of the LiFePO₄/Li+ cells in six...(이미지참조) 58

Figure 14. Potential profiles of the LiFePO₄/Li+ cell in six different...(이미지참조) 58

Figure 15. Potential profiles of the LiFePO₄/Li+ cell in six different...(이미지참조) 59

Figure 16. Rate performance of the LiFePO₄/Li+ cell in six different...(이미지참조) 59

Figure 17. Potential profile of rate performance of the LiFePO₄/Li+ cell in E(OMe)Pyrl-FSI...(이미지참조) 61

Figure 18. Potential profile of rate performance of the LiFePO₄/Li+ cell in P(OMe)Pyrl-FSI...(이미지참조) 61

Figure 19. Potential profile of rate performance ofthe LiFePO₄/Li+ cell in A(OMe)Pyrl-FSI...(이미지참조) 62

Figure 20. Potential profile of rate performance of the LiFePO₄/Li+ cell in PMPyrd-FSI...(이미지참조) 62

Figure 21. Potential profile of rate performance of the LiFePO₄/Li+ cell in EMIm-FSI...(이미지참조) 63

Figure 22. Potential profile of rate performance of the LiFePO₄/Li+in carbonate electrolytes...(이미지참조) 63

Figure 23. Outline of the binary electrolytes between the carbonate... 66

Figure 24. Images of the flammability tests of E 00, E 20, E 40, E 60, E... 69

Figure 25. Images of the flammability tests of E 00, E 20, E 40, E 60, E... 70

Figure 26. Viscosity of the binary electrolytes at 25 °C (blue) and... 74

Figure 27. Ionic conductivity of the binary electrolytes at 25℃... 74

Figure 28. Cathodic limit of 6 different electrolytes: E 00 (cyan), E... 76

Figure 29. Anodic limit of 6 different electrolytes.. 77

Figure 30. Cycle performance of the LiFePO₄/Li+ cells in six different... 79

Figure 31. Cycle performance of the LiFePO₄/Li+ cells in eight... 80

Figure 32. Potential profiles of the LiFePO₄/Li+ cell in five different... 81

Figure 33. Potential profiles of the LiFePO₄/Li+ cell in five different... 82

Figure 34. SEM images of the LiFePO₄cathode in each binary... 83

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