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研究生： 吳孟修
Wu, Meng-Xiu
論文名稱： 具六氮聯三伸萘之有機電極材料應用於鋰離子電池
Hexaazatriphenylene-based Organic Electrode Material for Lithium-ion Batteries
指導教授： 柯碧蓮
Watchareeya Kaveevivitchai
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年： 2020
畢業學年度： 108
語文別： 英文
論文頁數： 92
中文關鍵詞： 大規模儲能系統 、鋰離子電池 、有機化合物 、正極 、具六氮聯三伸萘之有機電池材料
外文關鍵詞： Large-scale energy storage systems, Lithium-ion batteries, Organic materials, Cathode, Hexaazatriphenylene-based materials
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    • 由於全球能源的需求快速增長，人們極需更高效率和效能的儲能系統，若要大量生產能源儲存元件，成本、毒性、環境影響是重要的考量因素。有機電極材料極具潛力，可取代鋰離子電池中正極材料所含較昂貴且有毒的無機化合物。有機材料可產自價廉且豐富的再生資源，對環境較友善，其氧化還原電位也可經由設計不同官能基而調整，以達到更好的電化學性質。
    六氮聯三伸萘（HAT）及其衍生物是具有相當潛力的化合物，且已證實在鋰離子電池中具有氧化還原活性。為了進一步提高 HAT 化合物的電化學性能，在此項研究中，我們藉由將 1,4-萘醌基團引入 HAT 架構形成中 HATNQ，使其增加氧化還原活性點，並且能夠進行高達 12 個電子移轉的反應。當 HATNQ 作為正極材料，在電流密度 200 mA g-1下可以獲得 426 mAh g-1 的可逆電容量，且在高電流密度 10 A g1下仍可達到 232 mAh g-1 HATNQ 所延伸的共軛系統導致更好的電子遷移率，氧化還原可逆性，出色的倍率性能和循環壽命。本研究藉由改變電極製備條件，以最佳化電池性能，並且利用數種原位與非原位鑑定分析技術呈現鋰離子電池在充放電過程中的氧化還原機制。

    Due to the fast-growing demand for energy worldwide, mankind is in great need for more efficient and powerful energy storage systems. Mass production of these energy storage units has led to the importance of cost, toxicity, and environmental impact. Organicbased electrode materials are one of the most promising candidates to replace the inorganicbased compounds commonly used as cathodes in Li-ion batteries, most of which contain costly and toxic metals. Organic compounds come from cheap and abundant renewable resources. They are also environmentally friendly. Organic electrodes can be designed to have different functional groups, which allow the redox potential to be fine-tuned. As a result,better electrochemical properties can be achieved. Hexaazatriphenylene (HAT) and itsderivatives are a promising group of compounds which have been shown to possess redox activities in Li-based batteries. In order to further improve the electrochemical performance of HAT compounds, in this work, the number of redox active sites has been increased by introducing 1,4-naphthoquinone group into the HAT core to form a functionalized extended derivative, HATNQ, capable of undergoing twelve-electron reaction. When used as cathode,HATNQ can achieve a reversible capacity as high as 426 mAh g-1 at 200 mA g-1, and at an extremely high rate of 10 A g-1, a capacity of 232 mAh g-1 still can be achieved. Furthermore,the extended conjugated system of HATNQ leads to better electronic mobility, redox reversibility, excellent rate capability, and superior cycle life. The electrode preparation conditions have been varied to optimize the battery performance. Several characterization techniques both ex-situ and in-situ have been used to reveal the redox mechanism of discharge/charge process in LIBs.

    Table of Contents 摘要 ........................................... i Abstract.............................................. ii Acknowledgments ....................................... iii List of Tables ........................................ vii List of Figures......................................... i Chapter 1 Introduction................................... 1 1.1 Inorganic vs. Organic Rechargeable Batteries ...................................... 1 1.2 Classification of Organic Lithium-ion Batteries ................................... 5 1.2.1 Conducting Polymers .................................................................... 6 1.2.2 Organosulfur Compounds ........................................................... 11 1.2.3 Radical Polymers......................................................................... 13 1.2.4 Organic Conjugated Carbonyl Compounds................................. 17 1.2.5 Heteroaromatic Compounds........................................................ 21 1.2.6 Molecular Design and Optimization ........................................... 28 1.3 Literature Review of Hexaazatriphenylene-based Materials............... 29 1.3.1 Introduction ................................................................................. 29 1.3.2 Triquinoxalinylene Materials ...................................................... 30 1.3.3 Hexacyanotripyradinylene........................................................... 31 1.3.4 Charge Transfer Complexes ........................................................ 33 1.3.5 Heteroaromatic Triquinoxalinylene............................................. 34 1.3.6 Hexaazatriphenylene-based Polymers......................................... 36 1.3.7 Hexaazatriphenylene-based Materials/Graphene Oxide ............. 38 1.3.8 Hexaazatriphenylene-hexacarbonitrile Carbon Fibers ................ 40 1.4 Background of Study ........................................................................... 42 1.4.1 Definition..................................................................................... 42 1.4.2 Batteries Design........................................................................... 44 1.6 Motivation and Purpose....................................................................... 47 Chapter 2 Hexaazatriphenylene-based Organic Electrode Materials ...................... 49 2.1 Introduction ......................................................................................... 49 2.2 Experimental Section........................................................................... 50 2.2.1 Materials ...................................................................................... 50 2.2.2 Preparation of HATNQ Cells ...................................................... 51 2.2.3 Materials Characterization........................................................... 51 2.2.4 Electrode Mechanistic Studies..................................................... 52 2.3 Results and Discussion ........................................................................ 53 2.3.1 Powder X-ray Diffraction(PXRD)............................................... 53 2.3.2 Raman Spectroscopy ................................................................... 54 2.3.3 Fourier-Transform Infrared Spectroscopy (FT-IR) ..................... 54 2.3.4 Optimization of Electrochemical Performance ........................... 55 2.3.5 Electrochemical Properties of HATNQ....................................... 68 2.3.6 Ex-situ and In-situ Analysis ........................................................ 74 2.3.6.1 Ex-situ and In-situ Raman Spectroscopy ......................... 74 2.3.6.2 Ex-situ FT-IR Spectroscopy ............................................. 76 2.3.6.3 Ex-situ XPS Spectroscopy................................................ 78 2.3.6.4 Ex-situ EPR ...................................................................... 81 2.3.6.5 Ex-situ Scanning Electron Microscopy (SEM) ................ 82 Chapter 3 Conclusions............................... 84 References .................................... 85

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