臺灣博碩士論文加值系統

延續實驗室以及學長開發具硫醚鏈噻吩的研究，接續合成出三大系列核心主體 BSTT, DSDTT 與 SBT(T,T)，藉由改變硫醚碳鏈長度來改善此系列的分子排列性，在這其中也得到 DSDTT 核心之單晶結構，證明分子設計的平面性，將核心主體向外接上不同的共軛結構與官能基，合成出兩個P-type以及一個N-type材料分子。
第四系列是以 SBT 核心結構改變硫醚碳鏈外接的位置，合成出 (T,T) 以及 (H,H) 和 (H,T) 不同位置的分子設計的高分子材料，藉由硫醚碳鏈外接位置的分子設計預期能達到更高的光電轉換效率，目前以pffBT-SBT(T,T)-20 (4) 已有 6.4 % 之光電轉換效率。
第五系列核心是利用 SBT 與 FFBT 結構，與香港的大學合作開發出的高分子材料，藉由改變硫醚碳鏈長度來改善轉換效率的表現，目前以pffBT-SBT-S16-C16 (7) 已有 9.43 % 之光電轉換效率。

New small molecules based on BSTT, DSDTT, and SBT(T,T) cores have been developed for organic thin film transistors (OTFTs). Two p-type and one n-type materials were synthesized and characterized. The highly planar DSDTT core was confirmed by single crystal structure and DSDTTQ-8 (3) exhibits the mobility up to 0.01 cm2/V-1s-1.
Three new regio-specific ((H,H), (T,T), and (H,T)) SBT-based polymers were developed which bearing thioalkyl chains (C20H41) in different positions of the SBT core. Furthermore, five new FFBT-SBT based polymers were developed where the SBT units were connected with different thioalkyl chains or alkyl chains. pffBT-SBT(T,T)-20 (4) exhibits a PCE up to 6.4% and pffBT-S16-C16 (7) exhibits a high PCE up to 9.43% in OPV. The optimization of FFBT-based polymer is still in progress.
The optical and electrochemical (HOMO and LUMO) properties of these materials were characterized by UV-vis and DPV. Thermal properties were investigated by TGA.

摘要 I
Abstract II
謝誌 III
目錄 IV
List of Figures IV
List of Schemes XVI
List of Tables XX
Appendixes catalog XXI
第一章 緒論 1
1-1 前言 2
1-2 有機場效電晶體導論 2
1-3 有機薄膜電晶體結構 8
1-4 有機薄膜電晶體之工作原理 10
1-5 有機薄膜的製備方式 12
1-5-1 氣相沉積 12
1-5-2 液相沉積 13
1-6 有機半導體分子載子移動率影響因素 16
1-6-1 分子設計 16
1-6-2 有機半導體分子排列模式與傳遞機制 17
1-6-3 介電層表面 21
1-7有機薄膜電晶之重要參數 22
1-7-1 載子移動率 (mobility) 23
1-7-2 開關電流比 (on / off current ratio) 25
1-7-3 起始電壓 (threshold voltage) 25
1-8 有機半導體材料 26
1-8-1 P-type 有機半導體材料 26
1-8-2 N-type 有機半導體材料 31
1-8-3 Ambipolar 有機半導體材料 34
1-9 有機太陽能電池之前言 35
1-10 有機太陽能電池之導論 37
1-11 太陽能電池之種類 39
1-11-1 矽太陽能電池 39
1-11-2化合物薄膜太陽能電池 42
1-11-3 有機太陽能電池 42
1-12 有機太陽能電池的元件 47
1-12-1 單層元件 47
1-12-2 雙層異質接面元件 (Bilayer heterojunction) 48
1-12-3 混合層異質接面元件 (Bulk heterojunction) 49
1-12-4 結合雙層及混合層異質結構 (hybrid planar-mixed molecule heterojunction structure) 50
1-13 有機太陽能電池的原理 51
1-13-1 光子吸收 (Optical Absorption) 51
1-13-2 激子擴散 (Exciton Diffusion) 52
1-13-3 電荷分離 (Charge Transfer) 52
1-13-4 電荷收集 (Charge Collection) 53
1-14 有機太陽能電池的重要參數 53
1-14-1 短路電流 Jsc (Short Circuit Current) 54
1-14-2 開路電壓 Voc (Open Circuit Voltage) 55
1-14-3 填充因子 FF (Fill Factor) 56
1-14-4 能量轉換效率 PCE (Power Conversion Efficiency) 56
1-14-5 外部量子效率 EQE (External Quantum Efficiency) 57
1-15 富勒烯衍生物 (Fullerene derivatives) 之簡介 57
1-16 有機太陽能電池材料 59
1-17 研究目的與動機 64
第二章 實驗 73
2-1 有機半導體化合物名稱對照表 74
2-2 實驗用品 76
2-2-1 實驗所用之化學藥品 76
2-2-2 實驗所用之溶劑除水方式 78
2-3 實驗儀器 78
2-3-1 核磁共振光譜儀 (Nuclear Magnetic Resonance, NMR)； Bruker AVANCE 200 / 300 / 500 MHz 78
2-3-2 紫外光 / 可見光吸收光譜 (Ultraviolet / visible spectro-photometer) ; U-3900 型 79
2-3-3 熱重分析儀 (Thermal Gravimetric Analyer, TGA)； TGA Instrument Q50 Series 79
2-3-4 電化學裝置 (Electrochemiacal Analyzer / Work- station)；HCH Instrumentent Model 621C 80
2-3-5 示差熱掃描卡計 (Differential Scanning Calorimeter, DSC)；NETZSCH DSC 204 F1 80
2-4-1 Dithieno[3,2-b:2',3'-d]thiophene (DTT; 13) 之 “one-pot” 之合成 81
2-4-2 Tributyl(dithieno[3,2-b:2',3'-d]thiophen-2-yl)stannane (2-SnBu3-DTT; 14) 之合成 82
2-4-3 5,5'-dibromo-4,4'-bis(tetradecylthio)-2,2'-bithiophene (di-Br-SBT(T,T)-14; 21) 之合成 83
2-4-4 2-(5'-(3a,7b-dihydrodithieno[3,2-b:2',3'-d]thiophen-2-yl)-3,3'-bis(hexylthio)-[2,2'-bithiophen]-5-yl)dithieno[3,2-b:2',3'-d]thiophene (DDTT-SBT(T,T)-C14 ; 1) 之合成 89
2-4-5 3,5-bis(octylthio)dithieno[3,2-b:2',3'-d]thiophene (DSDTT-8 ; 24) 之合成 90
2-4-6 2,6-dibromo-3,5-bis(octylthio)dithieno[3,2-b:2',3'-d]thiophene (di-Br-DSDTT-8 ; 25) 之合成 92
2-4-7 3',5'-bis(octylthio)-2,2':6',2''-terdithieno[3,2-b:2',3'-d]thiophene (DDTT-DSDTT-8 ; 2) 之合成 93
2-4-8 2,2'-(3,5-bis(octylthio)dithieno[3,2-b:2',3'-d]thiophene-2,6-diylidene)dimalononitrile (DSDTTQ-8 ; 3) 之合成 94
2-4-9 3-(hexylthio)thieno[3,2-b]thiophene (3-SC10-TT; 30) 之合成 95
2-4-10 5,5'-dibromo-3,3'-bis(decylthio)-2,2'-bithieno[3,2-b]thiophene (di-Br-BSTT-10; 32) 之合成 99
2-4-11 (3-((2-hexyldecyl)thio)thiophen-2-yl)trimethylsilane (2-TMS,3-Sb16-T; 37) 之合成 101
2-4-12 Trimethyl(3-((2-octyldodecyl)thio)thiophen-2-yl)silane (2-TMS,3-Sb20-T; 41) 之合成 104
2-4-13 5,5'-dibromo-4,4'-bis((2-octyldodecyl)thio)-2,2'-bithiophene (di-Br-SBT(T,T)-SCb20; 45) 之合成 107
2-4-14 5,5'-dibromo-3-(2-octyldodecyl)-3'-((2-octyldodecyl)thio)-2,2'-bithiophene (di-Br-SBT(H,H)-SCb20; 47) 之合成 110
2-4-15 5,5'-dibromo-4,4'-bis((2-octyldodecyl)thio)-2,2'-bithiophene (di-Br-SBT(H,T)-SCb20; 51) 之合成 112
2-4-16 5,6-difluoro-4-(5''-methyl-3',4''-bis((2-octyldodecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-7-(5-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (pffBT-SBT(T,T)-SCb20; 4) 之合成 115
2-4-17 5,6-difluoro-4-(5''-methyl-3',4''-bis((2-octyldodecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-7-(5-methylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (pffBT-SBT(H,H)-SCb20; 5) 之合成 118
2-4-18 5,6-difluoro-4-(5''-methyl-3',4''-bis((2-octyldodecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-7-(5-methylthiophen-2- yl)benzo[c][1,2,5]thiadiazole (pffBT-SBT(H,T)-SCb20; 6) 之合成 119
2-4-19 4,7-bis(5-bromo-4-(2-hexyldecyl)thiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (diBr-DT-FFBT-C16; 61) 之合成 121
2-4-20 4,7-bis(5-bromo-4-((2-hexyldecyl)thio)thiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (diBr-DT-FFBT-S16; 64) 之合成 124
2-4-21 4,7-bis(5-bromo-4-((2-octyldodecyl)thio)thiophen-2-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole (diBr-DT-FFBT-S20; 66) 之合成 126
2-4-22 4-(5''-(5,6-difluoro-7-(4'-(2-hexyldecyl)-3-((2-hexyldecyl)thio)-5'-methyl-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazol-4-yl)-3'-(2-hexyldecyl)-3''-((2-hexyldecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-5,6-difluoro-7-(5-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole(pffBT-S16-C16; 7) 之合成 128
2-4-23 4-(5''-(5,6-difluoro-7-(3-((2-hexyldecyl)thio)-5'-methyl-4'-(2-octyldodecyl)-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazol-4- yl)-3''-((2-hexyldecyl)thio)-3'-(2-octyldodecyl)-[2,2':5',2''-terthiop hen]-5-yl)-5,6-difluoro-7-(5-methylthiophen-2- yl)benzo[c][ 1,2,5]thiadiazole (pffBT-S16-C20; 8) 之合成 131
2-4-24 4-(5''-(5,6-difluoro-7-(3-(2-hexyldecyl)-4'-((2-hexyldecyl)thio)-5'-methyl-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazol-4-yl)-3''-(2-hexyldecyl)-3'-((2-hexyldecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-5,6-difluoro-7-(5-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (pffBT-C16-S16; 9) 之合成 133
2-4-25 4-(5''-(5,6-difluoro-7-(5'-methyl-3,4'-bis((2-octyldodecyl)thio)-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazol-4-yl)-3',3''-bis((2-octyldodecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-5,6-difluoro-7-(5-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (pffBT-S20-S20: 10) 之合成 136
2-4-26 4-(5''-(5,6-difluoro-7-(4'-(2-hexyldecyl)-5'-methyl-3-((2-octyldodecyl)thio)-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazo l-4-yl)-3'-(2-hexyldecyl)-3''-((2-octyldodecyl)thio)-[2,2':5',2''-terthiophen]-5-yl)-5,6-difluoro-7-(5-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (pffBT-S20-C16: 11) 之合成 138
第三章 結果與討論 141
3-1合成方法探討 142
3-1-1 BSTT 核心主體之合成方法探討 142
3-1-2 DSDTT 核心主體之合成方法探討與分子設計 144
3-1-3 SBT 核心主體之合成方法探討 146
3-1-4 pffBT-SBT 核心主體之合成方法探討 147
3-2 UV-vis 光學性質探討 148
3-3 DPV電化學性質探討 154
3-4 有機半導體材料之熱穩定性探討 160
3-5 有機半導體材料之晶體探討 163
3-6 有機太陽能電池材料之效率探討 164
第四章 結論 167
參考文獻 170
附錄 176

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