用於高性能n型有機薄膜晶體管的溶液 - 二亞甲基取代的醌基二炔基噻吩（DTDSTQ）基小分子

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研究生：	阿芭特 Alfonsina Abat Amelenan Torimtubun
論文名稱：	用於高性能n型有機薄膜晶體管的溶液 - 二亞甲基取代的醌基二炔基噻吩（DTDSTQ）基小分子 Solution-Sheared Dicyanomethylene-Substituted Quinoidal Dithioterthiophene (DTDSTQ)-Based Small Molecules for High-Performance n-Type Organic Thin Film Transistors Application
指導教授：	劉振良 Cheng-Liang Liu
口試委員:
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程與材料工程學系 Department of Chemical & Materials Engineering
論文出版年：	2017
畢業學年度：	104
語文別：	英文
論文頁數：	123
中文關鍵詞：	有機薄膜晶體管、溶液剪切、n型有機小分子、有機半導體
外文關鍵詞：	organic thin film transistors, solution shearing, n-type organic small molecule, organic semiconductor
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有機半導體溶液製程沉積方法提供有前景的技術來製造大面積，低成本和彈性的有機電子元件。本研究報告了通過剪切力塗佈法方法及分子設計工程增強n通道有機薄膜電晶體管 (Organic Thin Film Transistor; OTFT) 性能的策略。我們使用下列四種具有不同烷基側鍊長度的二氰基亞甲基取代的醌型二噻吩噻吩(DTDSTQ)為核心的新型有機半導體的新型材料系列: (1)DTDSTQ-6 (硫代己基)，(2)DTDSTQ-10 (硫代癸基)，(3)DTDSTQ-14 (硫代十四烷基)，並且在烷基側餾分中不引入硫 (4)DTDRTQ-14 (十四烷基)。從DFT計算和單晶X光射線衍射獲得的優化的幾何結果顯示了DTDSTQ的高核平面性。 DTDSTQ核心以面對面的π-π堆疊佈置堆疊，堆疊距離為3.42 Å，短分子間S-N距離為3.56 Å，形成二維網絡電荷傳輸。更進一步結合2D-GIXRD分析，知道有機分子側立於基板上。高核平面性和非常低 -4.2 eV的LUMO能階有利的分子組裝，也表明DTDSTQ可能是新型有前景的n型有機半導體材料。對這些新化合物的物理，電化學以及電學性質進行了深入研究。通過溶液剪切力塗佈的DTDSTQ-14實現了高達0.41 cm2V-1s-1的最高電子遷移率，具有至少1個月的良好熱穩定性。結果表明，通過側鏈基工程可以改善剪切DTDSTQ的元件性能。

Solution-processable organic semiconductor deposition methods show promising technologies to fabricate large-area, low-cost and flexible organic electronics. This study reports the strategy for enhancing n-channel organic thin film transistors (OTFTs) performance by molecular design engineering through solution-shearing method. New series of organic semiconductor materials based small molecules with the core of dicyanomethylene-substituted quinoidal dithioterthiophene (DTDSTQ) modified by different alkyl side chain length: (1)DTDSTQ-6 (thio-hexyl), (2)DTDSTQ-10 (thio-decyl), (3)DTDSTQ-14 (thio-tetradecyl) and without sulfur introduction in alkyl side moiety: (4)DTDRTQ-14 (tetradecyl) were used. Optimized geometry obtained from DFT calculation and single-crystal X-ray diffraction reveals the high core planarity of DTDSTQ. The DTDSTQ core packed in a face-to-face slipped π-π stacking arrangement, with short stacking distance of 3.42 Å and short intermolecular S – N distance of 3.56 Å, forming 2-dimensional network charge transport. Further investigation with 2D-GIXRD analysis reveal that molecules packed edge-on to the substrate. The favorable molecular packing, the high core planarity and very low LUMO energy level of -4.2 eV suggesting that DTDSTQs could be a promising new n-type organic semiconductor materials. The physical, electrochemical as well as electrical properties of these new compounds are thoroughly investigated. The highest electron mobility of up to 0.41 cm2 V-1 s-1 with good thermal stability for at least 1 month was achieved by solution-sheared DTDSTQ-14. The results show that the device performance of solution-sheared DTDSTQs can be improved by side chain engineering.

摘要    i
ABSTRACT    ii
ACKNOWLEDGEMENTS    iii
TABLE OF CONTENTS    v
LIST OF FIGURES    vii
LIST OF TABLES    xiii
CHAPTER 1 INTRODUCTION    1
1-1    Background    1
1-2    Organic Thin Film Transistors (OTFTs)    4
1-2-1    OTFTs Device Architecture    5
1-2-2    Operating Principle    6
1-2-3    Electrical Characteristics    9
1-3    Organic Semiconductor Small Molecules    15
1-3-1    p-Type Organic Semiconductor    16
1-3-2    n-Type Organic Semiconductor    17
1-3-2-1    Material Requirements    20
1-3-2-2    Quinoidal Oligothiophenes    22
1-4    Organic Semiconductor Deposition Process    24
1-4-1    Vacuum Thermal Deposition    24
1-4-2    Solution Deposition    26
1-4-2-1    Drop-casting    26
1-4-2-2    Spin-coating    29
1-4-2-3    Printing    30
1-4-2-4    Meniscus-guided Coating - Solution Shearing    33
1-5    Research Objective    35
1-6    Thesis Outline    37
CHAPTER 2 EXPERIMENTAL SECTION    39
2-1    Materials    39
2-1-1    Organic Semiconductors    39
2-1-2    Solvents    40
2-2    Experiment Apparatus    40
2-3    Experimental Methods    41
2-3-1    Device Fabrication    41
2-3-2    Electrical Measurement    43
2-3-3    Thin-Film Characterization    44
2-3-3-1    Polarized Optical Microscopy (POM)    44
2-3-3-2    Ultraviolet – Visible Spectrometer (UV-Vis)    44
2-3-3-3    Atomic Force Microscopy (AFM)    45
2-3-3-4    Grazing Incidence X-Ray Diffraction (GIXRD)    45
2-3-3-5    Transmission Electron Microscopy (TEM)    46
2-3-4    DFT Calculation    46
CHAPTER 3 RESULTS AND DISCUSSION    47
3-1    Material Properties    47
3-1-1    Physical and Electrochemical Properties    47
3-1-2    Molecular Orbital Computation    49
3-1-3    Optical Properties    51
3-2    Organic Thin-Film Transistors Characterization    54
3-3    Crystal Structures    59
3-4    Thin Film Microstructures and Morphologies    61
3-4-1    Optical and Polarized Optical Microscopy (OM, POM)    61
3-4-2    Atomic Force Microscopy (AFM)    65
3-4-3    Grazing – Incidence X-Ray Diffraction (GIXRD)    68
3-4-4    Transmission Electron Microscopy (TEM)    71
3-5    Device Stability    73
CHAPTER 4  CONCLUSION AND FUTURE WORK    75
4-1    Conclusion    75
4-2    Future Work    76
BIBLIOGRAPHY    77
APPENDIX    85

                                

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