具硫醚及硒醚鏈之可溶性有機薄膜電晶體?吩小分子之開發

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卓長輝(Chang-Hui Cho) 查詢紙本館藏

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論文名稱

具硫醚及硒醚鏈之可溶性有機薄膜電晶體?吩小分子之開發
(Development of Solution Processable Thioalkylated and Selenalkylated Thiophenes for Small Molecular Organic Thin Film Transistors)

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摘要(中)

本研究主要開發具硫醚鏈及硒醚鏈之有機薄膜電晶體?吩材料，
在硫醚鏈系列中開發出 n 型材料 TSBTQ 與 p 型材料 DDTTDSDTT
。在硒醚鏈系列中，開發出以 SeBT 為核心之多個 p 型小分
子材料。
本實驗室之前已開發具四硫醚鏈之 n 型分子 TSBTQ-6 與
TSBTQ-14，其硫醚鏈分別為 C6H13 與 C14H29，兩者元件電性分別已
具 0.10 cm2V-1s-1 和 0.14 cm2V-1s-1。本研究繼續探討硫醚碳鏈之鏈長
效應，開發出硫醚鏈為 C10H21 之 TSBTQ-10 (1)，藉由溶液製程
(shearing) 此新材料製成元件之電性可達 0.18 cm2V-1s-1，為此系列之
最高效能小分子。
另外本實驗室之前已開發具雙硫醚鏈 C10H21 之 p 型分子
DSDTT-10，元件電性可達 2.6 cm2V-1s-1。本研究繼續探討硫醚碳鏈
之鏈長效應，開發出硫醚鏈為 C8H17 之 DSDTT-8 (2)，藉由溶液製
程 (shearing) 此新材料製成元件之電性更高達 3.2 cm2V-1s-1，為此系
列之最高效能小分子。從所獲得之 DSDTT-10 與 DSDTT-8 之單晶
結構中我們發現引入硫原子於鏈中可幫助分子堆疊。且因硫醚鏈位於
同側，使得 DSDTT 核心可倆倆併排成”雙筒堆疊”，有利載子之傳遞。
本實驗室之前已開發具雙硫醚鏈 C14H29 之 p 型分子 SBT-14，
元件電性可達 1.7 cm2V-1s-1。本研究以此核心為板模，以硒取代硫原
子，開發出具硒醚鏈之 SeBT 新核心，為探討共軛與硒醚碳鏈之鏈長
效應，開發出五個 p 型小分子材料。從所獲得之 DDTT-SeBT-10 與
DDTT-SeBT-14 之單晶結構中我們發現引入硒原子於鏈中可幫助分
ii
子堆疊，使得分子間以磚型堆疊，有利載子之傳遞。其中 DDTTSeBT-
14 具有優異之電性表現高達 4.0 cm2V-1s-1，為目前台灣本土所
開發之可溶性 p 型有機薄膜電晶體小分子之溶液製程最高電性紀錄。

摘要(英)

New small molecules based on TSBT, DSDTT, and SeBT cores have
been synthesized for organic thin film transistors (OTFTs).
For the first TSBT series, n-type TSBTQ-14 (TSBTQ with C14H29
chains) and TSBTQ-6 (TSBTQ with C6H13 chains) exhibited mobility of
0.14 cm2V-1s-1 and 0.10 cm2V-1s-1. To further complete the side chains
effect study, TSBTQ-10 (1; TSBTQ with C10H21 chains) was synthesized
and characterized. Via solution shearing, TSBT-10 exhibits the best
mobility up to 0.18 cm2V-1s-1 in this series.
For the second DSDTT series, DDTT-DSDTT-10 (DSDTT with
C10H21 chains) exhibited high mobility 2.6 cm2V-1s-1. To further complete
the side chains effect study, DDTT-DSDTT-8 (2; with C8H17 chains) was
synthesized and characterized. Via solution shearing, DDTT-DSDTT-8
demonstrates the best mobility up to 3.2 cm2V-1s-1. Both molecular
structures of DSDTTs were determined by single crystal X-ray diffraction
and exhibits two parallel face-to-face columnar stacking’s with a very close
interplanar core distance of 3.6 A .
For the third series, a couple new small molecules based on the
selenylated bithiophene (SeBT) with different end-capped aromatic groups
and alkyl chains were developed. DDTT-SeBT-14 (7; with C14H29 chains)
exhibits the highest mobility of 4.00 cm2V-1s-1 via solution shearing. The
molecular structures of DDTT-SeBT-14 and DDTT-SeBT-10 (6) were
determined by single crystal X-ray diffraction and showed brick-type
iv
molecular stacking.

關鍵字(中)

★ 有機薄膜電晶體

關鍵字(英)

★ Organic Thin Film Transistors

論文目次

摘要 ............................................................................................................. i
Abstract .................................................................................................... iii
致謝 ............................................................................................................. v
目錄 ........................................................................................................... vi
List of Figures .......................................................................................... xi
List of Schemes ...................................................................................... xiii
List of Tables ........................................................................................... xv
Appendixes catalog ............................................................................... xvi
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 有機薄膜電晶體之元件結構 ......................................................... 7
1-4 有機薄膜電晶體之工作原理 ......................................................... 9
1-5 有機薄膜的製備方式 ................................................................... 11
1-5-1 氣相沉積 ................................................................................ 11
1-5-2 液相沉積 ................................................................................ 12
1-6 有機半導體分子載子移動率影響因素 ....................................... 15
1-6-1 分子設計 ................................................................................ 15
1-6-2 有機半導體分子排列模式與傳遞機制 ............................... 15
1-6-3 介電層表面 ............................................................................ 20
1-7 有機薄膜電晶之重要參數 ........................................................... 21
1-7-1 載子移動率 (mobility) ......................................................... 21
vii
1-7-2 開關電流比 (on / off current ratio) .................................... 23
1-7-3 起始電壓 (threshold voltage) .............................................. 23
1-8 有機半導體材料 ........................................................................... 24
1-8-1 p-type 有機半導體材料 ........................................................ 24
1-8-2 n-type 有機半導體材料 ........................................................ 28
1-8-3 Ambipolar 有機半導體材料 ................................................ 31
1-9 有機薄膜電晶體的應用 ............................................................... 33
1-9-1 軟性顯示器 ............................................................................ 33
1-9-2 無線射頻標籤 ........................................................................ 33
1-9-3 氣體及生物感測器 ................................................................ 34
1-9-4 相關之發展應用 .................................................................... 34
1-10 研究動機與目的 ......................................................................... 36
1-10-1 TSBTQ 系列 ....................................................................... 39
1-10-2 DDTT-DSDTT 系列 ........................................................... 40
1-10-3 SeBT 系列............................................................................ 41
第二章實驗............................................................................................. 44
2-1 有機半導體化合物名稱對照表 ................................................... 45
2-2 實驗用品 ....................................................................................... 46
2-2-1 實驗所用之化學藥品 ............................................................ 46
2-2-2 實驗所用之溶劑除水方式 .................................................... 48
2-3 實驗儀器 ....................................................................................... 48
2-3-1 核磁共振光譜儀 (Nuclear Magnetic Resonance, NMR)；
Bruker AVANCE 300 / 500 / 600 MHz .......................................... 48
2-3-2 紫外光 / 可見光吸收光譜 (Ultraviolet / visible spectroviii
photometer) ; U-3900 型 ................................................................ 49
2-3-3 電化學裝置 (Electrochemiacal Analyzer / Workstation)；
HCH Instrumentent Model 621C ................................. 49
2-3-4 示差熱掃描卡計 (Differential Scanning Calorimeter,
DSC)；NETZSCH DSC 204 F1 .................................................... 50
2-4 有機半導體化合物合成步驟 ....................................................... 51
2-4-1 Thieno[3,2-b]thiophene (12) 之合成 ................................... 51
2-4-2 2-bromothieno[3,2-b]thiophene (13) 之合成 ..................... 53
2-4-3 Dithieno[3,2-b:2′,3′-d]thiophene (14) 之 “one-pot” 之合
成 ...................................................................................................... 54
2-4-4 2-bromodithieno[3,2-b:2′,3′-d]thiophene (15) 之合成 ...... 55
2-4-5 tributyl(dithieno[3,2-b:2′,3′-d]thiophen-2-yl)stannane (16)
之合成 ............................................................................................... 56
2-4-6 5,5′-dibromo-3,3′,4,4′-tetrakis(decylthio)-2,2′-bithiophene
(21) 之合成 ...................................................................................... 57
2-4-7 3,5-bis(octylthio)dithieno[3,2-b:2′,3′-d]thiophene (24) 之合
成 ...................................................................................................... 60
2-4-8 2,6-dibromo-3,5-bis(octylthio)dithieno[3,2-b:2′,3′-
d]thiophene (25) 之合成 ................................................................ 62
2-4-9 3,3′-bis(hexylselanyl)-2,2′-bithiophene (27) 之合成 .......... 63
2-4-10 3,3′-bis(decylselanyl)-2,2′-bithiophene (29) 之之合成 .... 65
2-4-11 3,3′-bis(tetradecylselanyl)-2,2′-bithiophene (31) 之合成 66
2-4-12 3,3′-bis(hexylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)bis(tributylstannane) (33) 之合成 ......................................... 67
ix
2-4-13 3,3′-bis(decylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)bis(tributylstannane) (33) 之合成 ......................................... 68
2-4-14 3,3′-bis(tetradecylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)bis(tributylstannane) (34) 之合成 ......................................... 69
2-4-15 2,2′-(3,3′,4,4′-tetrakis(decylthio)-5H,5′H-[2,2′-
bithiophenylidene]-5,5′-diylidene)dimalononitrile (1) 之合成 .. 70
2-4-16 3′,5′-bis(octylthio)-2,2′:6′,2′′-terdithieno[3,2-b:2′,3′-
d]thiophene (2) 之合成 .................................................................. 71
2-4-17 3′′,4′-bis(tetradecylselanyl)-2,2′:5′,2′′:5′′,2′′′-
quaterthiophene (3) 之合成 .......................................................... 72
2-4-18 2,2′-(3,3′-bis(tetradecylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)dithieno[3,2-b]thiophene (4) 之合成 ..................................... 73
2-4-19 2,2′-(3,3′-bis(hexylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)didithieno[3,2-b:2′,3′-d]thiophene (5) 之合成 ..................... 74
2-4-20 2,2′-(3,3′-bis(decylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)didithieno[3,2-b:2′,3′-d]thiophene (6) 之合成 ..................... 75
2-4-21 2,2′-(3,3′-bis(tetradecylselanyl)-[2,2′-bithiophene]-5,5′-
diyl)didithieno[3,2-b:2′,3′-d]thiophene (7) 之合成 ..................... 76
第三章結果與討論 ................................................................................ 78
3-1 有機半導體材料之光學性質探討 ............................................... 79
3-1-1 SeBT 核心主體之合成分法探討 ......................................... 79
3-2 有機半導體材料之光學性質探討 ............................................... 80
3-2-1 UV-vis 光學性質探討 ........................................................... 80
3-3 有機半導體材料之電化學性質探討前言 ................................... 84
x
3-3-1 DPV 電化學性質探討........................................................... 84
3-4 有機半導體材料之熱性質探討 ................................................... 89
3-4-1 有機半導體材料之熱性質分析............................................ 89
3-5 有機半導體材料之晶體探討 ....................................................... 92
3-5-1 DDTT-DTTR2-11 之晶體探討 ............................................ 92
3-4-2 DDTT-DSDTT-8 之晶體探討 .............................................. 93
3-4-3 DT-SeBT-14 之晶體探討 ...................................................... 94
3-4-4 DDTT-SeBT-10 之晶體探討 ................................................ 95
3-4-5 DDTT-SeBT-14 之晶體探討 ................................................ 96
第四章結論............................................................................................. 97
參考文獻 ................................................................................................... 99
附錄 ......................................................................................................... 105

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指導教授

陳銘洲(Ming-Chou Chen)

審核日期

2018-8-21

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