可溶性有機薄膜電晶體材料三併環
及四併環噻吩衍生物之開發

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姓名

朴瑪莉(Mery Budiarti) 查詢紙本館藏

畢業系所

化學學系

論文名稱

可溶性有機薄膜電晶體材料三併環及四併環噻吩衍生物之開發
(Highly Soluble Dithienothiophene (DTT) andTetrathienoacene (TTA ) Derivatives Development forOrganic Thin Film Transistor (OTFT) Application )

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至系統瀏覽論文 ( 永不開放)

摘要(中)

本研究延續實驗室之併環噻吩開發，製備出具有高穩定性可溶性有機半導體材料，這兩個可溶性半導體材料皆具有良好的共軛程度，於三併環噻吩以及四併環噻的分子中引入長碳鏈，並在其兩端接上苯噻吩，兩個新的可溶性半導體材料即被合成出，且合成後的材料也將探討其物理性質與電性表現。其中 DBT-TTAR2 此材料具有較低的 LOMO 值、較高的 HOMO 值、擁有較低的能帶隙，有助於載子的注入傳輸，在文獻中 DP-DTT，P-type 半導體材料，其載子移動率分別為 0.42cm2/Vs，而本論文中在分子內引入長碳鏈使其變成可溶性半導體材料，有機會運用溶液製程方式將材料鍍上元件；延伸分子共軛程度，增加了 π-π 混成軌域，希望能夠提高其載子移動效率，有不錯的電性表現。

摘要(英)

This research focused on the development of highly soluble dithienothiophene (DTT) and tetrathienoacene (TTA) derivatives for organic thin film transistor (OTFT) application. Two new highly soluble thienoacenes derivative, DBT-DTTR2 and DBT-TTAR2 were synthesized. The enhancement of π – π molecular conjugation with dibenzo[b,d]thiophene (DBT) group and increasing its solubility properties with introducing alkyl side chains on both of DTT and TTA core. The chemical and physical characterizing results which were included characterizing theirs optical, electrochemical and thermal properties shows that DBT-TTAR2 has a better performance than DBT-DTTR2 for OTFT application. DBT-DTTR2 and DBT-TTAR2 were fabricated as a p-type semiconductor of OTFT by solution process at Industrial Technology Research Institute. Both compounds were predicted can bring out a high mobility value which is around 0.1 cm2/Vs. It was compared with another organic semiconductor based on thienoacene derivatives, DP-DTT (μ = 0.42 cm2/Vs) which has a good stability.

關鍵字(中)

★ 有基薄膜電晶體
★ 三併環噻吩
★ 四併環噻吩
★ 溶液製成

關鍵字(英)

★ organic thin film transistor
★ dithienothiophene
★ solution process
★ tetrathienothiophene

論文目次

A B S T R A C T i
摘要 ii
A C K N O W L E D G E M E N T S iii
T A B L E O F C O N T E N T S iv
L I S T O F F I G U R E S vi
L I S T O F T A B L E S ix
CHAPTER 1 INTRODUCTION 1
1.1 Background 1
1.2 Purpose 4
CHAPTER 2 OVERVIEW 5
2.1 Introduction of Organic Semiconductor (OSC) 5
2.2 Properties of Organic Semiconductor (OSC) 7
2.3 Organic Semiconductor Based On Thienoacene Derivative 16
2.4 Organic Thin Film Transistor (OTFT) 20
CHAPTER 3 EXPERIMENTAL SECTION 29
3.1 Materials and Methods 29
3.1.1 Materials 29
3.1.2 Methods 30
3.1.2.1 Nuclear Magnetic Resonance (NMR) 30
3.1.2.2 High Resolution Mass Spectrometer 30
3.1.2.3 Ultraviolet Visible Spectrometer (UV-vis) 31
3.1.2.4 Differential Scanning Calorimeter (DSC) 31
3.1.2.5 Thermo Gravimetric Analysis (TGA) 31
3.1.2.6 Electrochemical Analyzer – Differential Pulse Parameter (DPV) 31
3.2 Synthesis 32
3.2.1 Synthetic Scheme Route 32
3.2.1.1 DBT-DTTR2 33
3.2.1.2 DBT-TTAR2 34
3.2.2 Synthetic of 2,6-bis(benzo[b]thiophen-2-yl)-3,5-diundecanyldithieno[3,2-b:2’’,3’’-d]thiophene or DBT-DTTR2 35
3.2.2.1 Tetrabromothiophene (1a) 35
3.2.2.2 1,1’-(3,4-Dibromo-2,5-thienyl)didodecanol (2a) 35
3.2.2.3 1,1’-(3,4-Dibromo-2,5-thienyl)didodecanone (3a) 36
3.2.2.4 2,6-Dicarboethoxy-3,5-diundecanyldithieno[3,2-b:2’3’-d]-thiophene (4a) 36
3.2.2.5 2,6-Dicarboxylate acid-3,5-diundecanyldithieno[3,2-b:2’3’-d]-thiophene (5a) 37
3.2.2.6 3,5-Diundecanyldithieno[3,2-b:2’3’-d]thiophene (6a) 37
3.2.2.7 2,6-Dibromo-3,5-diundecanyldithieno[3,2-b:2’3’-d]thiophene (7a) 38
3.2.2.8 2,6-Bis(benzo[b]thiophen-2-yl)-3,5-diundecanyldithieno[3,2-b:2’’,3’’-d]thiophene or DBT-DTTR2 (8a) 38
3.2.3 Synthetic of 2,6-bis(benzo[b]thiophen-2-yl)-3,7-dipentadecyltetrathienoacene or DBT-TTAR2 39
3.2.3.1 2,5-Di(1,1’-pentadecanone)-3,6-dibromo-thieno[3,2-b]thiophene (1b) 39
3.2.3.2 2,6-Dicarboethoxy-3,7-dipentadecyltetrathienoacene (2b) 40
3.2.3.3 3,7-Dipentadecyltetrathienoacene-2,6-dicarboxylate acid (3b) 40
3.2.3.4 3,7-Dipentadecyltetrathienoacene (4b) 41
3.2.3.5 2,6-Dibromo-3,7-dipentadecyltetrathienoacene (5b) 41
3.2.3.6 2,6-Bis(benzo[b]thiophen-2-yl)-3,7-dipentadecyltetrathienoacene or DBT-TTAR2 (6b) 42
CHAPTER 4 RESULT AND DISCUSSION 43
4.1 Synthesis 43
4.1.1 DBT-DTTR2 43
4.1.2 DBT-TTAR2 44
4.2 Molecular Characterization 44
4.2.1 Optical Properties 44
4.2.2 Electrochemical properties 49
4.2.3 Thermal properties 53
4.3 Organic Thin Film Transistor Fabrication and Characterization 57
CHAPTER 5 CONCLUSIONS 59
R E F E R E N C E 61
CHAPTER 6 APPENDIX 65
6.1 DBT-DTTR2 (NMR) 65
6.2 DBT-TTAR2 (NMR) 69
6.3 DBT-TTAR2 (Mass Spectroscopy) 72

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指導教授

陳銘洲(Chen-Ming Chou)

審核日期

2012-7-9

推文