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研究生:王詠翔
研究生(外文):Yong-Siang Wang
論文名稱:新型二烷基苯基富勒烯吡咯烷之合成鑑定及其物理與光電性質探討
論文名稱(外文):Synthesis, Physical and Optoelectronic Behaviors of Ethylphenyl Fulleropyrrolidines
指導教授:芮祥鵬芮祥鵬引用關係王立義
口試委員:魏騰芳
口試日期:2013-07-11
學位類別:碩士
校院名稱:國立臺北科技大學
系所名稱:有機高分子研究所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2013
畢業學年度:101
語文別:中文
論文頁數:116
中文關鍵詞:Prato reaction富勒烯衍生物高分子太陽能電池
外文關鍵詞:Prato reactionFullerene derivativesPolymer solar cells
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本研究目的主要在於尋找良好的有機太陽能電池受體材料。而碳六十本身具有卓越的電子受體特性,因此被廣泛的運用於有機太陽能電池。有鑑於實驗室內先前合成的碳六十衍生物NMPC,因其溶解度不甚理想,而導致光電轉換效率不佳。因此,本研究進一步設計出一系列具有高溶解度的富勒烯吡咯烷衍生物,包含:NMPEC、NPPEC、NiPPPEC、NHPEC、NEHPEC、NiPTPEC及NCHPEC,並以1H NMR、13C NMR、MALDI-TOF MS、elemental analysis (EA)進行結構鑑定;應用UV-Vis吸收光譜分析各結構的光學能隙(optical bandgap) ;利用330 nm吸收度與濃度的檢量線,計算碳六十衍生物的溶解度;且由cyclic voltammetey (CV)來測得碳六十衍生物的LUMO與UV所得的光學能隙進而回推出它們的HOMO能階數值。而此系列碳六十衍生物在順式太陽能電池中,其光電轉換效率並不如預期,主要是不同推拉電子的碳六十衍生物,在主動層的分佈情形不同,因此我們利用反式太陽能電池結構改變電子電洞傳遞方向,使效率均可提升至3%。並設計結構NMEOPPEC、NMCPEC製備成元件與模擬進行分析,而此結構設計方向也將有助於反式太陽能電池的發展。

Fullerenes have been widely utilized as the electron acceptor material in polymer solar cells because they possess good electron affinity ability and high electron mobility. To resolve the poor solubility problem of our previously synthesized fullerene derivatives NMPC, in this study, we further design a new series of fulleropyrrolidine derivatives, including NMPEC, NPPEC, NiPPPEC, NHPEC, NEHPEC, NiPTPEC, and NCHPEC, with excellent solubility in common organic solvent. The molecular structure of these fullerene derivatives was characterized by 1H NMR, 13C NMR, MALDI-TOF MS and elemental analysis (EA). UV-Vis was employed to determine their optical band gap and solubility. CV was applied to resolve the LUMO of C60 derivatives.
However, as this series of fullerene derivatives was used as electron acceptor to fabricate conventional poly(3-hexylthiophene-based bulk-heterojunction solar cells, abnormal S-shaped current-voltage (I-V) curves were observed due to the formation of fullerene-rich layer between hole transport and photoactive blend. Consequently, the inverted cell structure gives nice I-V curves for all fulleropyrrolidines synthesized herein with a power conversion efficiency of ~3%, demonstrating they can be utilized as effective acceptor material in inverted polymer solar cells.

摘 要 I
ABSTRACT II
致謝 IV
目錄 VI
表目錄 IX
圖目錄 X
第一章 緒論 1
1-1前言 1
1-2 高分子太陽能電池之工作原理 2
1-3碳六十分子簡介 4
1-4高分子太陽能電池與碳六十之文獻回顧 7
1-5 研究動機 20
第二章 實驗 21
2-1 實驗藥品 21
2-1-1 藥品對照表 21
2-2實驗儀器 23
2-2-1 高真空系統(high vacuum system) 23
2-2-2 核磁共振光譜儀(nuclear magnetic resonance spectro-meter,NMR;型號: Bruker AC-500) 23
2-2-3 紫外光/可見光/近紅外光吸收光譜儀(UV/VIS/NIR spectrometer;型號: JASCO V-670) 24
2-2-4 元素分析儀(Elemental analyzer,EA;型號: 德國elementar VarioEL-III;NCSH) 24
2-2-5 電化學循環伏安法(Cyclic voltammtry,CV;型號:CHI660A) 25
2-2-6 電灑游離質譜儀(Electrospray lionization mass ,ESI-MS) 25
2-2-7 基質輔助雷射脫附游離飛行時間質譜儀(Matrix-assisted laser desorption ionization-time of flight mass spectrometry,MALDI-TOF;型號:Autoflex III TOF/TOF) 26
2-2-8 X光粉末繞射儀(D8 Advance X-ray Diffractometer,PXRD;型號:Bruker AXS) 26
2-3新型碳六十衍生物之合成 27
2-3-1新型碳六十衍生物之合成路徑 27
2-3-2 N-methyl-2-phenylethylfulleropyrrolidine (NMPEC)之合成 31
2-3-3 N-phenyl-2-phenylethylfulleropyrrolidine (NPPEC)之合成 32
2-3-4 N-isopropyl-2-phenylethylfulleropyrrolidine (NiPPPEC)之合成 33
2-3-5 N-hexyl-2-phenylethylfulleropyrrolidine (NHPEC)之合成 35
2-3-5 N-(2-ethylhexyl)-2-phenylethylfulleropyrrolidine (NEHPEC)之合成 37
2-3-6 N-isopentyl-2-phenethylfullerepyrrolidine (NiPTPEC)之合成 39
2-3-7 N-cyclohexyl-2-phenylethylfulleropyrrolidine (NCHPEC)之合成 41
2-3-8 N-(4-methoxycarbonylphenyl)-2-phenylethylfulleropyrrolidine (NMCPPEC)之合成 43
第三章 結果與討論 47
3-1 新型碳六十衍生物之合成分析與結構鑑定 47
3-1-1 Prato reaction 47
3-1-2 新型碳六十衍生物結構鑑定 48
3-1-2-1 NMPEC結構鑑定 48
3-1-2-2 NPPEC結構鑑定 51
3-1-2-3 NiPPPEC結構鑑定 53
3-1-2-4NHPEC結構鑑定 58
3-1-2-5 NEHPEC結構鑑定 62
3-1-2-6 NiPTPEC結構鑑定 66
3-1-2-7 NCHPEC結構鑑定 70
3-1-2-8 NMCPPEC結構鑑定 74
3-1-2-9 NMEOPPEC結構鑑定 78
3-2 新型碳六十衍生物光學、物理與電化學性質探討 82
3-2-1新型碳六十衍生物之物理性質分析 82
3-2-1-1新型碳六十衍生物之溶解度 82
3-2-1-2新型碳六十衍生物之結晶性分析 84
3-2-2 新型碳六十衍生物之光學性質分析 85
3-2-3新型碳六十衍生物之電化學性質分析 86
3-3新型碳六十衍生物之理論計算 93
3-3-1理論計算分析 93
3-4元件效率 95
第四章 結論 99
第五章 參考文獻 101
附錄A質譜分析 104
附錄B元素分析 113


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