具雙氟茚酮七併環戊二烯併二噻吩與雙環戊烷二噻吩之非富勒烯受體開發

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賴啟嘉(Chi Jia Lai) 查詢紙本館藏

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具雙氟茚酮七併環戊二烯併二噻吩與雙環戊烷二噻吩之非富勒烯受體開發

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至系統瀏覽論文 (2028-6-20以後開放)

摘要(中)

本研究以實驗室先前利用CDT (cyclopentadithiophene)單元所開發之多併環材料: DCDTT (dicyclopentadithienothiophene)與多環材料: BCDT (bicyclopentadithiophene)作為核心，多環噻吩之核心有助於電荷轉移進而增加載子移動率，並於多環的核心架構中引入分支的碳鏈以增進分子溶解度，透過在結構末端接上具有雙氟原子的茚酮 (fluorinated indanone, INF)分子，製備出兩種結構相似的化合物: INF-DCDTT與INF-BCDT。相比於其他鹵素元素，具有雙氟原子的茚酮溶解度更佳，有助於提高分子的溶解度，使元件製備成膜能較為平整不堆疊，利於探討元件所得之光伏參數。
本研究開發之化合物，除了能作為非富勒烯受體(non-fullerene acceptors, NFAs)應用於有機太陽能電池(Organic Solar Cell, OPV)中，亦能作為鈣鈦礦電池(perovskite solar cells, PSCs)的添加劑使用，透過末端的羰基與修飾的二氰乙烯基去鈍化鈣鈦礦電池的表面缺陷，能有助於提高元件效能，本實驗室於2022年四月發表至JMCA的文獻研究中，利用INCl-DCDTT作為鈣鈦礦層之添加劑，能有效提高電池效能從原先17%至21.39%，因此本研究使用拉電性更強且溶解度更好的雙氟茚酮，期望能獲得更好的元件效能。這些材料皆完成NMR與質譜之結構鑒定，並利用UV-vis 及 DPV測量其光學及電化學性質(HOMO、LUMO與Eg)，再藉由 DSC 及 TGA 測量其材料熱穩定性，這些新開發的有機光電材料正進行相關元件測試，期望有良好的效能表現。

摘要(英)

DCDTT (Dicyclopentadithienothiophene) and BCDT (bicyclopentadithiophene) are two organic optoelectronic materials that are derived from the CDT (cyclopentadithiophene) unit. The core of the CDT helps with charge transfer and increases the carrier mobility. Introducing branched carbon chains into the core structure of the CDT enhances the molecular solubility. Both of two compounds were end-capped with the same electron withdrawing group, fluorinated dicyanomethylene indanone (INF). Via Knoevenagel condensation, two similar materials were obtained, INF-DCDTT and INF-BCDT. Additionally, compared to other halogen elements, indanones with difluorine atoms have better solubility, which is essential for producing high-quality film in solar cell devices. These two compounds also can serve as additive in perovskite solar cells (PSCs). Our group has published a related study on JMCA in April, 2022. The presence of carbonyl (C=O) and cyano (C≡N) groups have a good interaction with undercoordinated Pb2+ ions and passivate the trap states in the perovskite films. Introducing INCI-DCDTT as a donor passivator into Pb-based PSCs increases the power conversion efficiency from 17% to 21.39% compared with devices without the additive. It is expected that INF-DCDTT can achieve better device performance by using stronger electron-withdrawing and better solubility difluorine atoms. The chemical structures of these newly developed materials were characterized by NMR spectroscopy and mass spectrometry. Furthermore, their optical properties were investigated using UV-vis spectroscopy, their electrochemical properties were analyzed by DPV, and their thermal stabilities were determined by DSC and TGA. Optoelectronic devices made from these newly developed small molecules are currently being optimized.

關鍵字(中)

★ 雙氟茚酮

關鍵字(英)

論文目次

目錄
摘要 i
Abstract ii
謝誌 iv
目錄 v
List of Figures ix
List of Schemes xi
List of Tables xiii
第一章緒論 1
1-1 太陽能電池之前言 2
1-2 太陽能電池之概論 3
1-2-1 矽晶太陽能電池 5
1-2-2 無機化合物半導體太陽能電池 5
1-2-3 有機太陽能電池 6
1-3 太陽能電池之基本元件與組成 7
1-4 太陽能電池之運作原理(光伏效應) 9
1-4-1 光子吸收(Light absorption) 10
1-4-2 激子分離與擴散(Exciton dissociation and diffusion) 10
1-4-3 電荷傳輸(Charge transfer) 11
1-4-4 電荷收集(Charge collection) 11
1-5 有機光伏打太陽能電池之元件 12
1-6 太陽光譜與太陽能電池的光伏參數 13
1-6-1 J-V曲線(J-V Curve) 16
1-6-2 短路電流密度(Short circuit current density, JSC) 17
1-6-3 開路電壓(Open circuit voltage, VOC) 17
1-6-4 外部量子效率(External Quantum Efficiency, EQE) 18
1-6-5 填充因子(Fill Factor, FF) 18
1-6-6 光電轉換效率(Power conversion efficiency, η, PCE) 19
1-7 N型有機光伏打太陽能電池材料沿革 19
1-7-1 N型富勒烯有機光伏打材料(Fullerene Acceptors) 20
1-7-2 N型非富勒烯有機光伏打材料(Non-Fullerene Acceptors) 21
1-7-3 具氟茚酮應用於N型非富勒烯有機光伏打材料 30
1-7-4 有機光伏打材料應用於鈣鈦礦太陽能電池 34
1-8 研究動機與目的 38
第二章實驗部分 40
2-1 化合物名稱對照 41
2-2 實驗藥品 42
2-2-1實驗所用之化學藥品 42
2-2-2實驗所用之溶劑除水方式 43
2-3 實驗儀器 44
2-3-1 核磁共振光譜儀 (Nuclear Magnetic Resonance, NMR)；Bruker AVANCE 300 / 500 MHz 44
2-3-2 高解析質譜儀(High Resolution Mass Spectrometer, HRMS)；JMS-700 HRMS 45
2-3-3示差熱掃描卡計 (Differential Scanning Calorimeter, DSC)；NETZSCH DSC 204 F1 45
2-3-4 紫外光/可見光/近紅外光吸收光譜 (Ultraviolet Visible Near-infare Spectrophotometer, UV/VIS/NIR Spectrophotometer)；HITACHI UH-5700 型 45
2-3-5 熱重分析儀 (Thermal Gravimetric Analyer, TGA)； Perkin Elmer TGA 55 46
2-3-6 電化學裝置 (Electrochemical Analyzer / Work- station)；HCH Instrumentent Model 621C 46
2-4 合成步驟 47
2-4-1 5,6-difluoroisobenzofuran-1,3-dione (6)之合成 47
2-4-2 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (8)之合成 49
2-4-3 Dithieno[3,2-b:2′,3′-d]thiophene (10)一鍋化合成 51
2-4-4 2,6-Bis(tributylstannyl)dithieno[3,2-b:2′,3′-d] thiophene (11)之合成 52
2-4-5 Ethyl 2-bromothiophene-3-carboxylate (14)之合成 53
2-4-6 Diethyl 2,2′-(dithieno[3,2-b:2’,3’-d]thiophene-2,6-diyl)-bis-(thiophene-3-carboxylate) (15) 之合成 55
2-4-7 1-Bromo-4-((2-hexyldecyl)oxy)benzene (17)之合成 56
2-4-8 diCHO-DCDTT (20) 之合成 57
2-4-9 INF-DCDTT (1) 之合成 60
2-4-10 5,5′-bis(tributylstannyl)-2,2′-bithiophene之合成 61
2-4-11 diethyl [2,2′:5′,2′′:5′′,2′′′-quaterthiophene]-3,3′′′-dicarboxylate (24)之合成 63
2-4-12 1-bromo-4-((2-ethylhexyl)oxy)benzene (25) 之合成 64
2-4-13 BCDT-b8 (27) 之合成 65
2-4-14 diCHO-BCDT-b8 (28) 之合成 67
2-4-15 INF-BCDT-b8 (2) 之合成 68
第三章結果與討論 70
3-1 具氟茚酮合成路徑與產率優化探討 71
3-2 有機光電材料之光學性質探討 78
3-3 有機光電材料之電化學性質探討 82
3-4 有機光電材料之熱穩定性質分析 85
第四章結論 88
第五章實驗改良可行之辦法 90
參考文獻 93
附錄 106

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指導教授

陳銘洲(Ming Chou Chen)

審核日期

2023-6-17

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