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姓名	李翊嫻(Yi-Hsien Li)  查詢紙本館藏	畢業系所	化學學系
論文名稱	可溶性雙噻吩並吡咯衍生物 有機光電材料之開發
檔案	[Endnote RIS 格式]    [Bibtex 格式]    [相關文章]   [文章引用]   [完整記錄]   [館藏目錄]   至系統瀏覽論文 (2026-7-26以後開放)
摘要(中)	本論文研究主要分為有機光伏打電池 (OPVs)、有機薄膜電晶體 (OTFT) 和鈣鈦礦電池中電洞傳輸層 (HTLs) 三個系列之材料開 發。 本研究主要延續之前開發出的雙噻吩並吡咯 (DTP) 核心，將其 延伸出兩個新核心，一為 TSDTP，為 DTP 掛上帶硫醚鏈之噻吩;另 外一個為BDTP，為DTP之二聚體，二者皆有兩種碳鏈b-C16H33 及 b-C20H41，並將其兩末端外接拉電子基團 3-(二氰基亞甲基)茚-1-酮 (IN) 與 5,6-(二氯)-3-(二氰基亞甲基)茚-1-酮 (INCl) ，分別為 IN-TSDTP-b16 (1) 、 IN-TSDTP-b20 (2) 、 INCl-TSDTP-b16 (3) 、 INCl-TSDTP-b20 (4) 、 IN-BDTP-b16 (5) 、 IN-BDTP-b20 (6) 、 INCl-BDTP-b16 (7)、INCl-BDTP-b20 (8) ，開發出八種有機光伏打電 池材料。另外，以 DTP 二聚體 (BDTP) 為核心開發之新醌型結構 BDTPQ-b16 (9)。此外，以DTP為核心開發三個不同鏈長之電動傳 輸層材料，分別為 b-C8H17 之 DTP-2D-b8 (10)、b-C16H33 之 DTP-2D-b16 (11) 及 b-C20H41 之 DTP-2D-b20 (12)。目前已將 DTP-2D-b8 及 DTP-2D-b16 應用在鈣鈦礦電池中，初步得到的元件 效能分別可達 13.60% 及 13.91% 之光電轉換效率。 這些新材料的光學和電化學性能 ( HOMO 和 LUMO ) 通過 UV-vis 和 DPV 來進行測定，並透過DSC和TGA來測定熱穩定性。 這些新開發小分子的光電元件正在測試優化中。
摘要(英)	A series of new organic optoelectronic materials were synthesized and characterized for organic photovoltaic cells (OPVs), organic thin film transistor (OTFT) and hole transporting layers (HTLs). Two new dithienopyrrole (DTP) cores were developed for OPVs. First, DTP core was end-capped with a thioalkylated thiophene unit to give more conjugated TSDTP. Second, the DTP core was dimerized to give more conjugated BDTP. To enhance the solubility of the new DTPs, b-C16H33 and b-C20H41 were introduced in the DTP cores. Then, the above four cores were formylated and then end-capped with two electron withdrawing groups, IN and INCl, to give IN-TSDTP-b16 (1), IN-TSDTP-b20 (2), INCl-TSDTP-b16 (3), INCl-TSDTP-b20 (4), IN-BDTP-b16 (5), IN-BDTP-b20 (6), INCl-BDTP-b16 (7), and INCl-BDTP-b20 (8). Furthermore, BDTP-based quinoid, BDTPQ-b16 (9), was synthesized for OTFT application. Finally, three new DPT-based HTLs with three different chains, b-C8H17, b-C16H33, and b-C20H41, were synthesized to give DTP-2D-b8 (10), DTP-2D-b16 (11), and DTP-2D-b20 (12), respectively. Currently, DTP-2D-b8 and DTP-2D-b16 based pervoskite solar cell exhibit power conversion efficiency of 13.60% and 13.91%, respectively. The optical and electrochemical properties (HOMO and LUMO) of these new materials were characterized by UV-vis and DPV. Thermal properties were investigated by DSC and TGA. Optoelectronic devices used these new developed small molecules are under optimization.
關鍵字(中)	★ 有機光伏打電池 ★ 有機薄膜電晶體 ★ 電洞傳輸層	關鍵字(英)
論文目次	摘 要 I Abstract II 謝 誌 IV 目錄 V List of Schemes XII List of Figures XV List of Tables XVII 附錄目錄 XVIII 第一章 緒論 1 1-1 有機太陽能電池之前言 2 1-2 有機太陽能電池的發展 3 1-2-1 矽晶太陽能電池 6 1-2-2 無機化合物半導體太陽能電池 6 1-2-3 有機太陽能電池 7 1-3 有機光伏打電池之元件結構 8 1-3-1 雙層式異質接面 (Bilayer heterojunction, PHJ) 9 1-3-2 體異質接面 (Bulk heterojunction, BHJ) 9 1-3-3 串聯結構 10 1-4 有機光伏打電池之運作原理 10 1-4-1 光激發 (Optical absorption) 11 1-4-2 激子擴散與分離 (Exction diffusion and dissociation) 12 1-4-3 電荷傳輸 (Charge transfer) 12 1-4-4 電荷收集 (Charge collection) 13 1-5 有機光伏打電池參數介紹 14 1-5-1 J-V 曲線 15 1-5-2 短路電流 (Short circuit current, JSC) 16 1-5-3 開路電壓 (Open circuit voltage, VOC) 16 1-5-4 外部量子效率 (Eternal quantum efficiency, EQE) 17 1-5-5 填充因子 (Fill factor, FF) 17 1-5-6 能量轉換效率 (Power conversion efficiency, η) 18 1-6 富勒烯與非富勒烯受體 18 1-6-1非富勒烯稠環電子受體 20 1-7 有機光伏打電池材料 20 1-7-1 P-type 有機光伏打材料 21 1-7-2 N-type 有機光伏打材料 24 1-8 有機薄膜電晶體之前言 29 1-9 有機薄膜電晶體結構 30 1-9-1 基板 (Substrate) 30 1-9-2 絕緣層 (Insulator) 31 1-9-3 有機半導體層 (Organic Semiconductor) 31 1-9-4閘極 (Gate)、源極 (Source)、汲極 (Drain) 32 1-10 有機薄膜電晶體之元件結構 32 1-11 有機薄膜電晶體之工作原理 33 1-12 有機薄膜電晶體傳導機制 34 1-13 有機薄膜電晶體材料排列方式 35 1-13-1分子結晶度 35 1-13-2 有機半導體分子排列模式 36 1-14 有機薄膜電晶體材料 38 1-14-1 P-type 有機薄膜電晶體材料 38 1-14-2 N-type 有機薄膜電晶體材料 40 1-15 鈣鈦礦太陽能電池的發展 42 1-15-1 基本構造 43 1-15-2 工作原理 46 1-15-3 電洞傳輸層 47 1-16 研究動機與目的 48 1-16-1有機光伏打電池材料 48 1-16-2 有機薄膜電晶體材料 (OTFT) 51 1-16-3 電洞傳輸層材料 (HTL) 53 第二章 實驗部份 55 2-1 化合物名稱對照 56 2-2 實驗藥品 59 2-2-1 實驗所用之化學藥品 59 2-2-2 實驗所用之溶劑除水方式 61 2-3 實驗儀器 62 2-4 合成步驟 65 2-4-1 2-Hexylundecan-1-amine (15) 之合成 65 2-4-2 2-Octyldodecan -1-amine (18) 之合成 67 2-4-3 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (19, IN) 之合成 69 2-4-4 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1- ylidene)malononitrile (20, INCl) 之合成 69 2-4-5 3,3′-Dibromo-2,2′-bithiophene (21) 之合成 70 2-4-6 2,6-Dibromo-4-(2-hexyldecyl)-4H-dithieno[3,2-b: 2′,3′-d] pyrrole (23) 之合成 71 2-4-7 2,6-Dibromo-4-(2-octyldodecyl)-4H-dithieno [3,2-b:2′,3′-d]pyrrole (25) 之合成 73 2-4-8 3-(Octylthio)thiophene (27) 之合成 75 2-4-9 Trimethyl(3-(octylthio)thiophen-2-yl)stannane (29) 之合成 76 2-4-10 4-(2-hexyldecyl)-2,6-bis(3-(octylthio)thiophen-2-yl)-4H-dithieno [3,2-b:2′,3′-d]pyrrole (30, TSDTP-b16)之合成 78 2-4-11 4-(2-octyldodecyl)-2,6-bis(3-(octylthio)thiophen-2-yl)-4H-dithieno [3,2-b:2′,3′-d]pyrrole (32,TSDTP-b20) 之合成 79 2-4-13 5,5′-(4-(2-octyldodecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl) bis(4-(octylthio)thiophene-2- carbaldehyde) (33) 之合成 81 2-4-14 2,2′-((2Z,2′Z)-(((4-(2-hexyldecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole- 2,6-diyl)bis(4-(octylthio)thiophene-5,2-diyl))bis(methaneylylidene))bis(3-oxo-2,3-dihydro- 1H-indene-2,1-diylidene))dimalononitrile (1, IN-TSDTP-b16) 之合成 82 2-4-15 2,2′-((2Z,2′Z)-(((4-(2-octyldodecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole- 2,6-diyl)bis(4-(octylthio)thiophene-5,2-diyl))bis(methaneylylidene))bis(3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (2, IN-TSDTP-b20) 之合成 84 2-4-16 2,2′-((2Z,2′Z)-(((4-(2-hexyldecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole -2,6-diyl)bis(4-(octylthio)thiophene-5,2-diyl))bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (3, INCl-TSDTP-b16) 之合成 85 2-4-17 2,2′-((2Z,2′Z)-(((4-(2-octyldodecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole- 2,6-diyl)bis(4-(octylthio)thiophene-5,2-diyl))bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (3, INCl-TSDTP-b20) 之合成 86 2-4-18 4,4′-bis(2-hexyldecyl)-4H,4′H-[2,2′-bidithieno[3,2-b:2′,3′-d]pyrrole] -6,6′-dicarbaldehyde (35) 之合成 88 2-4-19 4,4′-bis(2-octyldodecyl)-4H,4′H-[2,2′-bidithieno [3,2-b: 2′,3′-d]pyrrole]-6,6′-dicarbaldehyde (37) 之合成 90 2-4-20 2,2′-((2Z,2′Z)-((4,4′-bis(2-hexyldecyl)-4H,4′H-[2,2′-bidithieno [3,2-b:2′,3′-d]pyrrole]-6,6′-diyl)bis(methaneylylidene))bis(3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (5, IN-BDTP-b16) 之合成 92 2-4-21 2,2′-((2Z,2′Z)-((4,4′-bis(2-octyldodecyl)-4H,4′H-[2,2′-bidithieno [3,2-b:2′,3′-d]pyrrole]-6,6′-diyl)bis(methaneylylidene))bis(3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile(6, IN-BDTP-b20) 之合成 93 2-4-22 2,2′-((2Z,2′Z)-((4,4′-bis(2-hexyldecyl)-4H,4′H-[2,2′-bidithieno[3,2-b:2′,3′-d]pyrrole]-6,6′-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (7, INCl-BDTP-b16) 之合成 94 2-4-23 2,2′-((2Z,2′Z)-((4,4′-bis(2-octyldodecyl)-4H,4′H-[2,2′-bidithieno [3,2-b:2′,3′-d]pyrrole]-6,6′-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile (8, INCl-BDTP-b20) 之合成 95 2-4-24 (E)-2,2′-(4,4′-bis(2-hexyldecyl)-[2,2′-bidithieno[3,2-b:2′,3′-d]pyrrolylidene] -6,6′(4H,4′H)-diylidene)dimalononitrile (9, BDTPQ-b16) 之合成 96 2-4-25 (4-methoxy-N-(4-methoxyphenyl)-N-(4-(tributyl stannyl)phenyl)aniline (40, TPA-SnBu3) 之合成 98 2-4-26 2,6-Dibromo-4-(2-ethylhexyl)-4H-dithieno [3,2-b:2′,3′-d]pyrrole (42) 之合成 100 2-4-27 4,4′-(4-(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl)bis (N,N-bis(4-methoxyphenyl)aniline) (10, DTP-2D-b8) 之合成 102 2-4-28 4,4′-(4-(2-hexyldecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl)bis (N,N-bis(4-methoxyphenyl)aniline) (11, DTP-2D-b16) 之合成 103 2-4-29 4,4′-(4-(2-octyldecyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl) bis(N,N-bis(4-methoxyphenyl)aniline) (12, DTP-2D-b20) 之合成 104 第三章 結果與討論 105 3-1 有機半導體材料之光學性質探討 106 3-1-1 UV 光學性質探討 106 3-1-2 有機光伏打電池電池材料 (OPVs) 106 3-1-3 有機薄膜電晶體材料 (OTFT) 109 3-1-4 電洞傳輸層材料 (HTL) 110 3-2 有機半導體材料之電化學性質探討 111 3-2-1 DPV 電化學性質探討 111 3-2-2 有機光伏打電池電池材料 (OPVs) 112 3-2-3 有機薄膜電晶體材料 (OTFT) 114 3-2-4 電洞傳輸層材料 (HTL) 114 3-3 有機半導體材料之熱穩定性分析 117 第四章 結論 119 參考文獻 122 附錄 129
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指導教授	陳銘洲 姚學麟(Ming-Chou Chen Shueh-Lin Yao)	審核日期	2021-7-28
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