可溶性具硫醚鏈噻吩及吡咯併吡咯二酮衍生物有機光電材料之開發

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研究生：	黃柏元 Bo-Yuan Huang
論文名稱：	可溶性具硫醚鏈噻吩及吡咯併吡咯二酮衍生物有機光電材料之開發 Development of Solution Diketonepyrrolopyrrole and Thioalkylated Thiophene Derivatives for Small Molecular Organic Thin Film Transistors
指導教授：	陳銘洲
口試委員:
學位類別：	碩士 Master
系所名稱：	理學院 - 化學學系 Department of Chemistry
論文出版年：	2020
畢業學年度：	108
語文別：	中文
論文頁數：	135
中文關鍵詞：	化學、材料
相關次數：	點閱：8 下載：0
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本論文為有機薄膜電晶體的材料開發，成功以吡咯併吡咯二酮單元為核心，並外接 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)，合成出四個 n 型有機薄膜電晶體材料 DIN-DPP-b20 (1)、DINCl-DPP-b20 (2)、DIN-DPP-b16 (3)、DINCl-DPP-b16 (4)。 Diketopyrrolopyrrole (DPP) 單元具有高的平面性及其有缺電子的性質和形成氫鍵的能力，導致其有很強的 π-π-stacking 作用及分子內電荷轉移作用，為一良好之OTFT的核心。利用 Uv-vis 探討此系列分子之吸收度差異，接上含氯之拉電子基團 INCl 之化合物(2)和(4)，相較化合物(1)和(3)有明顯的紅位移，再利用 DPV 探討所開發分子之 HOMO 與 LUMO 能階之差異。化合物(2)與(4)具 INCl 之 HOMO 與 LUMO 能階相較於化合物(1)與(3)都有明顯的下降。因其核心及外掛基團均具有良好平面性，期望提高薄膜的結晶性及元件的電性效能。延續實驗室之前開發具硫醚鏈噻吩的研究，開發出四個以具硫醚鏈聯噻吩 SBT 為核心的化合物，並外接 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)，合成出四個 n 型有機薄膜電晶體材料 DIN-SBT-14 (5)、DINCl-SBT-14 (6)、DIN-SBT-b16 (7)、DINCl-SBT-b16 (8)。利用 Uv-vis 探討此系列分子之吸收度差異，接上含氯之拉電子基團 INCl 之化合物(6)和(8)，相較化合物(5)和(7) 有明顯的紅位移，再利用 DPV 探討所開發分子之 HOMO 與 LUMO 能階之差異。化合物(6)與(8)具 INCl 之 HOMO 與 LUMO 能階相較於化合物(5)和(7)都有明顯的下降。藉聯噻吩上
ii
的 S 原子和硫醚鏈上 S 原子之間的分子內作用力，使得核心結構有更好的平面性，有利於電子的傳遞。

A series of diketopyrrolopyrrole (DPP)-based and thioalkylated bithiophene (SBT) small molecules were developed for organic thin film transistors (OTFTs). For the first series, the DPP cores with different alkyl chains were end-capped with electron withdrawing groups, such as dicyanomethylene indanone (IN) and dichlorodicyanomethylene indanone (INCl), to give four new small molecules, DIN-DPP-b20 (1), DINCl-DPP-b20 (2), DIN-DPP-b16 (3), and DINCl-DPP-b16 (4). The four DPP molecules have almost identical HOMOs. As expected, the LUMOs of the two chlorinated DPPs (DINCl-DPP-b20 (2) and DINCl-DPP-b16 (4)) were lower than those of DIN-DPP-b20 (1) and DIN-DPP-b16 (3), resulting a larger energy gap of the latter. This can be attributed to the electron withdrawing characteristic of the chlorine atoms. For the second series, the SBT cores with different alkyl chains were end-capped with electron withdrawing groups, IN and INCl, to give four new small molecules: DIN-SBT-14 (5), DINCl-SBT-14 (6), DIN-SBT-b16 (7), and DINCl-SBT-b16 (8). Similar to the DPP series, the four SBT molecules have almost identical HOMOs and the LUMOs of the two chlorinated SBTs (6 and 8) were lower than those of 5 and 7. Therefore, these two chlorinated SBTs exhibit smaller energy gap in the UV-Vis absorption in comparison to those non-chlorinated analogs.

摘要 ................................................................................................... i
Abstract........................................................................................... iii
致謝 ................................................................................................. iv
List of Figures ................................................................................. ix
List of Schemes ................................................................................. x
List of Tables ................................................................................. xiii
Appendixes catalog ........................................................................ xiv
第一章 緒論 ..................................................................................... 1
1-1 有機薄膜電晶體 (OTFTs)之前言 2
vi
1-2 有機場效電晶體導論有機場效電晶體導論...................................................................................................................................... 2
1-3 有機薄膜電晶體之元件結構有機薄膜電晶體之元件結構 .............................................................................................................. 7
1-4 有機薄膜電晶體之工作原理有機薄膜電晶體之工作原理 .............................................................................................................. 9
1-5 有機薄膜的製備方式有機薄膜的製備方式.................................................................................................................................. 11
1-5-1 氣相沉積氣相沉積 .......................................................................................................................................................... 11
1-5-2 液相沉積液相沉積 .......................................................................................................................................................... 12
1
1--6 6 有機半導體分子載子移動率影響因素有機半導體分子載子移動率影響因素 .......................................................................... 15
1-6-1 分子設計分子設計 .......................................................................................................................................................... 15
1-6-2 有機半導體分子排列模式與傳遞機制有機半導體分子排列模式與傳遞機制 ............................................................ 15
1-7 有機薄膜電晶有機薄膜電晶之重要參數之重要參數 .................................................................................................................. 20
1-7-1 載子移動率載子移動率 (mobility) .............................................................................................................. 20
1-7-2 開關電流比開關電流比 (on / off current ratio) .......................................................................... 22
1-7-3 起始電壓起始電壓 (threshold voltage) .......................................................................................... 22
1-8 有機半導體材料有機半導體材料 ................................................................................................................................................ 23
1-8-1 p-type 有機半導體材料有機半導體材料 ............................................................................................................ 23
1-8-2 n-type 有機半導體材料有機半導體材料 ............................................................................................................ 27
1-8-3 Ambipolar 有機半導體材料有機半導體材料................................................................................................ 30
1-9 有機薄膜電晶體的應用有機薄膜電晶體的應用 .......................................................................................................................... 32
1-9-1 軟性顯示器軟性顯示器 .................................................................................................................................................. 32
1-9-2 無線射頻標籤無線射頻標籤 .......................................................................................................................................... 32
1-9-3 氣體及生物感測器氣體及生物感測器 .......................................................................................................................... 33
1-9-4 相關之發展應用相關之發展應用 .................................................................................................................................. 33
1-10 研究動機與目的研究動機與目的 ............................................................................................................................................ 35
1-10-1 有機薄膜電晶體的材料開發有機薄膜電晶體的材料開發 ........................................................................................ 35
vii
第二章 實驗 ................................................................................... 40
2-1 有機半導體化合物名稱對照表有機半導體化合物名稱對照表 .................................................................................................. 41
2-2 實驗用品實驗用品 ........................................................................................................................................................................ 43
2-2-1 實驗所用之化學藥品實驗所用之化學藥品 .................................................................................................................. 43
2-2-2 實驗所用之溶劑除水方式實驗所用之溶劑除水方式 .................................................................................................... 45
2-3 實驗儀器實驗儀器 ........................................................................................................................................................................ 45
2-3-1 核磁共振光譜儀核磁共振光譜儀 (Nuclear Magnetic Resonance, NMR)；； Bruker AVANCE 300 / 500 / 600 MHz .................................................................................... 45
2-3-2 紫外光紫外光 / 可見光吸收光譜可見光吸收光譜 (Ultraviolet / visible spectro-photometer) ; U-3900 型型 .............................................................................................................................. 46
2-3-3 電化學裝置電化學裝置 (Electrochemiacal Analyzer / Work- station)；；HCH Instrumentent Model 621C ...................................................................................................... 46
2-3-4 示差熱掃描卡計示差熱掃描卡計 (Differential Scanning Calorimeter, DSC)；；NETZSCH DSC 204 F1 ........................................................................................................ 47
2-4 有機半導體化合物合成步驟有機半導體化合物合成步驟 .......................................................................................................... 48
2-4-1 3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrole-1,4(2H,5H) -dione(DPP) (9) 之合成之合成 .................................................................................................................................. 48
2-4-2 2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)pyrolo[3,4 -c]pyrrole-1,4(2H,5H)-dione ( DPP-b20 ) (10) 之合成之合成 .................................... 49
2-4-3 5,5'-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahyd ropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-2-carbaldehyde) (DPP-b20-CHO) (11) 之合成之合成 .............................................................................................................. 50
2-4-4 2,5-bis(2-hexyldecyl)-3,6-di(thiophen-2-yl)pyrrolo[3, 4- c] pyrrole-1,4(2H,5H)-dione( DPP-b16 ) (12) 之合成之合成.............................................. 51
viii
2-4-5 5,5'-(2,5-bis(2-hexyldecyl)-3,6-dioxo-2,3,5,6-tetrahydro pyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-2-carbaldehyde) (DPP-b16-CHO) (13) 之合成之合成 .................................................................................................................................. 52
2-4-6 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (14) 之合成之合成 53
2-4-7 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (15) 之合成之合成 .......................................................................................................................... 54
2-4-8 DIN-DPP-b20 (1) 之合成之合成 .................................................................................................. 55
2-4-9 DINCl-DPP-b20 (2) 之合成之合成 .................................................................................................. 56
2-4-10 DIN-DPP-b16 (3) 之合成之合成 .................................................................................................... 57
2-4-11 DINCl-DPP-b16 (4) 之合成之合成 ................................................................................................ 58
2-5-1 3,3'-dibromo-2,2'-bithiophene (16) 之合成之合成 .................................................... 59
2-5-2 3,3'-bis(tetradecylthio)-2,2'-bithiophene (17) 之合成之合成 .................... 60
2-5-3 3,3'-bis(tetradecylthio)-[2,2'-bithiophene]-5,5'-dicarbal dehyde (18) 之合成之合成 ...................................................................................................................................................................... 61
2-5-4 3,3'-bis((2-hexyldecyl)thio)-2,2'-bithiophene (19) 之合成之合成 ...... 62
2-5-5 3,3'-bis((2-hexyldecyl)thio)-[2,2'-bithiophene]-5,5'-di carbaldehyde (20) 之合成之合成 .......................................................................................................................... 63
2-5-6 DIN-SBT-14 (5) 之合成之合成 ............................................................................................................ 64
2-5-7 DINCl-SBT-14 (6) 之合成之合成 ........................................................................................................ 65
2-5-8 DIN-SBT-b16 (7) 之合成之合成 ........................................................................................................ 66
2-5-9 DINCl-SBT-b16 (8) 之合成之合成 .................................................................................................... 67
第三章 結果與討論 ........................................................................ 68
3-1-1 UV-vis 光學性質探討光學性質探討 .................................................................................................................. 69
ix
一、
一、 DPP 系列系列 n-type 有機半導體化合物有機半導體化合物 .............................................................. 69
二、
二、 SBT 系列系列 n-type 有機半導體化合物有機半導體化合物 .............................................................. 71
3-2 有機半導有機半導體材料之電化學性質探討前言體材料之電化學性質探討前言 .................................................................. 73
3-2-1 DPV 電化學性質探討電化學性質探討 ................................................................................................................ 73
一、
一、 DIN-DPP 系列有機半導體化合物系列有機半導體化合物 .......................................................................... 73
二、
二、 DIN-SBT 系列有機半導體化合物系列有機半導體化合物 .......................................................................... 74
3-3 有機半導體材料之有機半導體材料之熱性質探討熱性質探討 .................................................................................................. 75
3-3-1 有機半導體材料之熱性質分析有機半導體材料之熱性質分析 .................................................................................... 75
一、
一、 DPP 系列有機半導體化合物系列有機半導體化合物 .......................................................................................... 76
二、
二、 SBT 系列有機半導體化合物系列有機半導體化合物 .......................................................................................... 76
第四章 結論 ................................................................................... 78
參考文獻 ........................................................................................ 79
附錄 ................................................................................................ 85
List of Figures
Figure 1-1 無線射頻標籤與多功能卡片 ........................................ 4
Figure 1-2 軟性電子的應用 .......................................................... 6
Figure 1-3 場效電晶體結構示意圖................................................ 7
Figure 1-4 常見的有機場效電晶體結構 ........................................ 8
Figure 1-5 p-type 與 n-type 場效電晶體 ................................... 10
Figure 1-6 真空蒸鍍法與氣相沈積法示意圖 ............................... 12
Figure 1-7 液相沉積示意圖 ........................................................ 12
x
Figure 1-8 半導體分子間排列方式與電子傳遞關係示意圖 ......... 16
Figure 1-9 傳導帶與價帶的能隙關係 .......................................... 17
Figure 1-10 載子的傳遞機制 ...................................................... 18
Figure 1-11 半導體分子排列方式 ............................................... 19
Figure 1-12 有機薄膜電晶體相關應用產品................................. 34
Figure 3-1 DPP 系列之 UV 圖 .................................................. 70
Figure 3-2 SBT 系列之 UV 圖 .................................................. 71
Figure 3-3 DIN-DPP 系列之能階圖 ........................................... 74
Figure 3-4 DIN-SBT 系列之能階圖............................................ 75
Figure 3-5 DPP 系列之 TGA 圖 ............................................... 76
Figure 3-6 SBT 系列之 TGA 圖 ............................................... 78
List of Schemes
Scheme 1-1 Acene 的衍生物 ................................................... 24
Scheme 1-2 BTBT 與 NDT 的衍生物 .................................... 25
Scheme 1-3 DNTT 與 DTBDT 的衍生物 ............................... 25
Scheme 1-4 Oligothiophene 的衍生物 ..................................... 26
Scheme 1-5 P-type 有機半導體聚合物 .................................... 27
Scheme 1-6 含氟的有機半導體材料 ......................................... 28
Scheme 1-7 含 CN 官能基的有機半導體材料 ......................... 28
Scheme 1-8 NDI 與 PDI 的衍生物 ......................................... 29
Scheme 1-9 n-type 有機半導體材料 ........................................ 30
xi
Scheme 1-10 Ambipolar 有機半導體材料 ................................. 31
Scheme 1-11 本實驗室所開發的 P-type 有機半導體分子 ......... 36
Scheme 1-12 SBT 系列 OTFT 有機半導體分子 ...................... 37
Scheme 1-13 文獻上之結構 ....................................................... 37
Scheme 1-14 文獻上之結構 ....................................................... 38
Scheme 1-15 DPP 系列 OTFT 有機半導體分子 ...................... 39
Scheme 2- 1 Compound (9) 之合成步驟 ................................... 48
Scheme 2- 2 Compound (10) 之合成步驟 ................................. 49
Scheme 2- 3 Compound (11) 之合成步驟 ................................. 50
Scheme 2- 4 Compound (12) 之合成步驟 ................................. 51
Scheme 2- 5 Compound (13) 之合成步驟 ................................. 52
Scheme 2- 6 Compound (14) 之合成步驟 ................................. 53
Scheme 2-7 Compound (15) 之合成步驟 .................................. 54
Scheme 2-8 Compound (1) 之合成步驟 .................................... 55
Scheme 2-9 Compound (2) 之合成步驟 .................................... 56
Scheme 2-10 Compound (3) 之合成步驟 .................................. 57
Scheme 2-11 Compound (4) 之合成步驟 .................................. 58
Scheme 2-12 Compound (16) 之合成步驟 ................................ 59
Scheme 2-13 Compound (17) 之合成步驟 ................................ 60
Scheme 2-14 Compound (18) 之合成步驟 ................................ 61
Scheme 2-15 Compound (19) 之合成步驟 ................................ 62
Scheme 2-16 Compound (20) 之合成步驟 ................................ 63
Scheme 2-17 Compound (5) 之合成步驟 .................................. 64
Scheme 2-18 Compound (6) 之合成步驟 .................................. 65
xii
Scheme 2-19 Compound (7) 之合成步驟 .................................. 66
Scheme 2-20 Compound (8) 之合成步驟 .................................. 67
xiii
List of Tables
Table 1-1 傳統 TFT 與 OTFT 的比較 ....................................... 5
Table 1-2 真空蒸鍍法與溶液製程之比較 .................................... 14
Table 2-1 化合物名稱對照表 ...................................................... 41
Table 2-2 化學藥品列表 .............................................................. 43
Table 2-3 D-Solvent 化學位移 (Chemical Shift) ........................ 46
Table 3-1 化合物 (1) ~ (8) 之 UV-vis 光譜吸收數據表 ............ 72
Table 3-2 化合物 (1) ~ (8) 之 HOMO 與 LUMO 能階數據表 76
Table 3-3 化合物 (1) ~ (8) 之 性質溫度數據表 ......................... 78
xiv
Appendixes catalog
附錄 1 Compound (1) 1H NMR (CDCl3) 之光譜 ......................... 86
附錄 2 Compound (1) 13C NMR (CDCl3) 之光譜 ........................ 86
附錄 3 Compound (2) 1H NMR (CDCl3) 之光譜 ......................... 87
附錄 4 Compound (2) 13C NMR (CDCl3) 之光譜 ........................ 87
附錄 5 Compound (3) 1H NMR (CDCl3) 之光譜 ......................... 88
附錄 6 Compound (3) 13C NMR (CDCl3) 之光譜 ........................ 88
附錄 7 Compound (4) 1H NMR (CDCl3) 之光譜 ......................... 89
附錄 8 Compound (4) 13C NMR (CDCl3) 之光譜 ........................ 89
附錄 9 Compound (5) 1H NMR (CDCl3) 之光譜 ......................... 90
附錄 10 Compound (5) 13C NMR (CDCl3) 之光譜 ...................... 90
附錄 11 Compound (6) 1H NMR (CDCl3) 之光譜 ....................... 91
附錄 12 Compound (6) 13C NMR (CDCl3) 之光譜 ...................... 91
附錄 13 Compound (7) 1H NMR (CDCl3) 之光譜 ....................... 92
附錄 14 Compound (7) 13C NMR (CDCl3) 之光譜 ...................... 92
附錄 15 Compound (8) 1H NMR (CDCl3) 之光譜 ....................... 93
附錄 16 Compound (8) 13C NMR (CDCl3) 之光譜 ...................... 93
附錄 17 Compound (9) 1H NMR (CDCl3) 之光譜 ....................... 94
附錄 18 Compound (10) 1H NMR (CDCl3) 之光譜 ..................... 94
附錄 19 Compound (11) 1H NMR (CDCl3) 之光譜 ..................... 95
附錄 20 Compound (12) 1H NMR (CDCl3) 之光譜 ..................... 95
附錄 21 Compound (13) 1H NMR (CDCl3) 之光譜 ..................... 96
xv
附錄 22 Compound (14) 1H NMR (CDCl3) 之光譜 ..................... 96
附錄 23 Compound (15) 1H NMR (CDCl3) 之光譜 ..................... 97
附錄 24 Compound (16) 1H NMR (CDCl3) 之光譜 ..................... 97
附錄 25 Compound (17) 1H NMR (CDCl3) 之光譜 ..................... 98
附錄 26 Compound (18) 1H NMR (CDCl3) 之光譜 ..................... 98
附錄 27 Compound (19) 1H NMR (CDCl3) 之光譜 ..................... 99
附錄 28 Compound (20) 1H NMR (CDCl3) 之光譜 ..................... 99
附錄 29 Compound (1) 之 MASS ............................................ 100
附錄 30 Compound (2) 之 MASS ............................................ 101
附錄 31 Compound (3) 之 MASS ............................................ 102
附錄 32 Compound (4) 之 MASS ............................................ 103
附錄 33 Compound (5) 之 MASS ............................................ 104
附錄 34 Compound (6) 之 MASS ............................................ 105
附錄 35 Compound (7) 之 MASS ............................................ 106
附錄 36 Compound (8) 之 MASS ............................................ 107
附錄 37 DIN-DPP系列之 DPV 氧化還原圖 ............................ 108
附錄 38 DINCl-DPP系列之 DPV 氧化還原圖 .......................... 108
附錄 39 DIN-SBT 系列之 DPV 氧化還原圖 ........................... 109
附錄 40 DINCl-SBT 系列之 DPV 氧化還原圖 ......................... 109
附錄 41 DIN-DPP-b20 之 DSC 圖 .......................................... 110
附錄 42 DINCl-DPP-b20 之 DSC 圖 ........................................ 110
附錄 43 DIN-DPP-b16 之 DSC 圖 .......................................... 111
附錄 44 DINCl-DPP-b16 之 DSC 圖 ........................................ 111
附錄 45 DIN-SBT-14 之 DSC 圖............................................. 112
xvi
附錄 46 DINCl-SBT-14 之 DSC 圖 .......................................... 112
附錄 47 DIN-SBT-b16 之 DSC 圖........................................... 113
附錄 48 DINCl-SBT-b16 之 DSC 圖 ........................................ 113
                                

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