| 姓名 |
費達思(Firdausy Amalina Esya)
查詢紙本館藏 |
畢業系所 |
化學學系 |
| 論文名稱 |
(Soluble 3,3’-bis(tetradecylthio)-2,2’-bithiophene (SBT) Derived Small Molecules for Organic Thin Film Transistor (OTFT) Application)
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| 相關論文 | |
| 檔案 |
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 [相關文章]  [文章引用]  [完整記錄]  [館藏目錄]  至系統瀏覽論文 ( 永不開放)
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| 摘要(中) |
摘 要
近年來噻吩衍生物在有機薄電晶體方面受到越來越多的關注，分子如果要有良好的電性表向，本身須具備良好的-作用力和有效共軛長度，因此本研究將SBT分別結合BT和TVT合成出DTVT-SBT及DbT-SBT，兩者電性皆有0.1 cm2/Vs，且有良好的穩定性，適合用在p-type 的OTFT材料。 |
| 摘要(英) |
Organic Thin Film Transistors (OTFT) based on thiophene derivative organic semiconductors, has been receiving increasing attention over the last few years. Many researches develop the most important properties which is - molecular conjugation that can achieve a high performance in organic semiconductors. The novel and promising organic semiconductor has been synthesized based on conjugated 3,3’-bis(tetradecylthio)-2,2’-bithiophene (SBT) with addition bithiophene (BT) and thienovinylthiophene (TVT) as thiophene ring to enhance the - molecular conjugation. The chemical and physical properties which were characterizing their optical, electrochemical, and thermal properties show that DTVT-SBT has a higher performance than DbT-SBT. Both of the compounds are predicted can achieve high mobility at least 0.1 cm2/Vs and good stability for p-type semiconductor in OTFT application.
Key words : organic thin film transistor,3 ,3’-bis(tetradecylthio)-2,2’-bithiophene (SBT), bithiophene (BT), thienovinylthiophene (TVT), p-type semiconductor |
| 關鍵字(中) |
★ organic thin film transistor
★ 3,3’-bis(tetradecylthio)-2,2’-bithiophene (SBT)
★ bithiophene (BT)
★ thienovinylthiophene (TVT)
★ p-type semiconductor |
關鍵字(英) |
★ organic thin film transistor
★ 3,3’-bis(tetradecylthio)-2,2’-bithiophene (SBT)
★ bithiophene (BT)
★ thienovinylthiophene (TVT)
★ p-type semiconductor |
| 論文目次 |
TABLE OF CONTENTS
ABSTRACT i
摘 要 ii
ACKNOWLEDGEMENTS iii
TABLE OF CONTENTS iv
LIST OF FIGURES vii
LIST OF TABLES ix
CHAPTER 1 INTRODUCTION 1
1.1. Background 1
1.2. Purpose 5
CHAPTER 2 OVERVIEW 6
2.1. Introduction of Organic Semiconductor (OSC) 6
2.2. Properties of Organic Semiconductor (OSC) 7
2.3. Basic Working Principles of Organic Semiconductor 8
2.3. Organic Semiconductor Based On Thiophene Derivatives 12
2.4. Organic Thin Film Transistor (OTFT) 14
CHAPTER 3 EXPERIMENTAL SECTION 26
3.1. Materials and Methods 26
3.1.1. Materials 26
3.1.2. Methods 27
3.1.2.1. Nuclear Magnetic Resonance (NMR) 27
3.1.2.2. Ultraviolet Visible Spectrometer (UV-vis) 27
3.1.2.3. Differential Scanning Calorimeter (DSC) 28
3.1.2.4. Thermo Gravimetric Analysis (TGA) 28
3.1.2.5. Electrochemical Analyzer – Differential Pulse Parameter (DPV) 28
3.2. Synthesis 29
3.2.1. Synthetic Scheme Route 29
3.2.1.1. DbT-SBT 30
3.2.1.2. DTVT-SBT 31
3.2.2. Synthetic of 2,5-bis(bithiophene-2-yl)-3,3’-bis(tetradecylthio)- 2,2’-bithiophene or DbT-SBT 31
3.2.2.1. 2,2’-bithiophene (1.03) 31
3.2.2.2. 3,3’,5,5’-tetrabromo-2,2’-bithiophene (1.04) 32
3.2.2.3. 3,3’-dibromo-2,2’-bithiophene (1.05) 32
3.2.2.4. tetradecylthiol (1.06) 33
3.2.2.5. 3,3’-bis(tetradecylthio)-2,2’-bithiophene (1.07) 33
3.2.2.6. 4,4’-dibromo-3,3’-bis(tetradecylthio)-2,2’-bithiophene (1.08) 34
3.2.2.7. 5-tributhylstannyl)-2,2’-bithiophene (1.09) 34
3.2.2.8. 2,5-bis(bithiophene-2-yl)-3,3’-bis(tetradecylthio)- 2,2’-bithiophene (DbT-SBT) (1.10) 34
3.2.3. Synthetic of 2,5-bis(bithienovinylthiophene-2-yl)-3,3’-bis(tetradecylthio)- 2,2’-bithiophene or DTVT-SBT 35
3.2.3.1. 5-tributhylstannyl-2,2’-thienovinylthiophene (2.02) 35
3.2.3.2. 2,5-bis(bithienovinylthiophene-2-yl)-3,3’-bis(tetradecylthio)-2,2’-bithiophene (DTVT-SBT) (2.03) 35
CHAPTER 4 RESULT AND DISCUSSION 36
4.1. Synthesis 36
4.1.1. DbT-SBT 36
4.1.2. DTVT-SBT 36
4.2. Molecular Characterization 37
4.2.1. Optical Properties 37
4.2.2. Electrochemical Properties 40
4.2.3. Thermal Properties 42
4.3. Organic Thin Film Transistor Fabrication and Characterization 44
CHAPTER 5 CONCLUSIONS 46
REFFERENCES 47
CHAPTER 6 APPENDIX 50
6.1. NMR of Synthetic DbT-SBT 50
6.2. NMR of Synthetic DTVT-SBT 55
LIST OF FIGURES
Figure 1.1. Cost versus performance of organic and inorganic semiconductors. 2
Figure 1. 2. Chemical structure of alkyl-substituted oligothiophenes 3
Figure 1.3. Chemical structures of an oligothiophene with internal double bonds and asymmetric oligothiophene derivatives. 4
Figure 2.1. Schematic representation of a polymer chain showing examples of unsaturated () and solubilizing (sub) units 7
Figure 2.2. Scheme of the energetic levels of two isolated atom, a biatomic molecule and a solid 9
Figure 2.3. Schematic of the solution-shearing method with relevant processing parameters and information on heat supply, substrate, and shearing tool modification 11
Figure 2.4. Chemical structure of some of the well-studied p-type polymers and small molecules organic semiconductor 13
Figure 2.5. Schematic of the device configuration of OTFT 15
Figure 2.6. Top gate OTFTs : (a) TGTC and (b) TGBC structures. 16
Figure 2.7. (a) Output and (b) transfer (at Vds = - 1.5 V) characteristics of OTFTs in the TGTC ad TGBC configurations. 17
Figure 2.8. (a) Schematic structure of a field – effect transistor and applied voltages : L = channel length ; W = channel width ; Vd = drain voltage ; VTh = Threshold voltage ; Id = drain current ; (b-d) Illustrations of operating regimes of field – effect transistors : (b) linear regime ; (c) start of saturation regime at pinch – off ; (d) saturation regime and corresponding current – voltage characteristics. 19
Figure 4.1. Optical Spectra of DbT-SBT 37
Figure 4.2. Optical Spectra of DTVT-SBT 38
Figure 4.3. The comparison of optical spectra between DBT-SBT, DTVT-SBT, and DDTT-SBT 38
Figure 4.4. Example illustration a comparison of -* energy gap in a series of polyenes of increasing chain length 39
Figure 4.5. The comparison of electrochemically derived HOMO and LUMO energy level between DTVT-SBT and DbT-SBT using DPV 40
Figure 4.6. Illustration of diagram energy level from several type of alkene group 42
Figure 4.7. TGA weight loss vs temperature between DbT-SBT and DTVT-SBT 43
Figure 4.8. Bis(bithienylthiophene and alkynylthiophene oligomers 45
Figure 6.1. 2,2’-bithiophene 50
Figure 6.2. 3,3’,5,5’-tetrabromo-2,2’-bithiophene 51
Figure 6.3. 3,3’-dibromo-2,2’-bithiophene 51
Figure 6.4. Tetradecylthiol 52
Figure 6.5. 3,3’-bis(tetradecylthio)-2,2’-bithiophene 52
Figure 6.6. 4,4’-dibromo-3,3’-bis(tetradecylthio)-2,2’-bithiophene 53
Figure 6.7. 2,5-bis(bithiophene-2-yl)-3,3’-bis(tetradecylthio)- 2,2’-bithiophene (DbT-SBT) 54
Figure 6.8. 2,5-bis(bithienovinylthiophene-2-yl)-3,3’-bis(tetradecylthio)-2,2’-bithiophene (DTVT-SBT) 55
LIST OF TABLES
Table 3.1. Material Description of CAS NO 26
Tabel 4.1. Optical and electrochemical comparison of DTVT-SBT and DbT-SBT compounds
41
Table 4.2. The comparison of thermal properties of DbT-SBT and DTVT-SBT 44 |
| 參考文獻 |
Afzali, A. B. 2002. An Efficient Synthesis of Symmetrical Oligothiophenes : Synthesis and Transport Properties of A Soluble Sexithiophene Derivative. Chemistry Material , 1742-1746.
Bao, Z. A. 2007. Organic Field-Effect Transistors. London: CRC Press Taylor and Francis Group.
Brusso, J. L. 2008. Two-Dimensional Structural Motif in Thienoacene Semiconductors: Synthesis, Structure, and Properties of Tetrathienoanthracene Isomers. Chemistry of Materials , 2484.
Cinar, M. E. 2015. Thienothiophenes, Dithienothiophenes, and Thienoacenes: Syntheses, Oligomers, Polymers, and Properties. Chemical Review , 3036-3140.
Dimitrakopoulos, C. E. 1997. Trans-trans-2,5-bis[2-[5-(2,2′-bithienyl)[ethenyl]thiophene : Synthesis, characterization, thin film deposition and fabrication of organic field-effect transistors. Syn. Met. , 193-197.
Doi, I. K. 2012. High mobility organic thin-film transistors on plastic substrate. Current Applied Physic , 32-35.
Dong, H. W. 2010. High performance organic semiconductors for field-effect transistors. Chemical Communications , 5211.
Facchetti, A. 2011. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Application. Chemistry of Materials Review , 733-758.
Farchioni, R. A. 2001. Organic Electronic Materials : Conjugated Polymers and Low Molecular Weight Organic Solids. New York: Springer-Verlag Berlin Heidelberg.
Fu, Y. L. 2009. High field-effect mobility from poly (3-hexylthiophene) thin-film transistors by solvent–vapor-induced reflow. Organic Electronic , 883-888.
Garnier, F. E. 1998. Dihexylquaterthiophene, a two dimensional liquid crystal-like organic semiconductor with high transport properties. Chemistry Material , 3334-3339.
Gsänger, M. K. 2014. High-Performance Organic Thin-Film Transistors of J Stacked Squaraine Dyes. Journal of The American Chemical Society , 2351-2362.
Gupta, D. K. 2009. An analysis of the difference in behavior of top and bottom contact organic thin film transistors using device simulation. Organic Electronic , 775-784.
Halik, M. K. 2003. Relationship Between Molecular Structure and Electrical Performance of Oligothiophene Organic Thin Film Transistors. Advanced Materials , 917.
Hamadani, B. 2007. Electronic Charge Injection and Transport in Organic Field-Effect Transistors. Houston, Texas: Rice University.
Kano, M. M. 2011. Control of device parameters by active layer thickness in organic thin film transistors. Journal of Applied Physics , 073307-1–073307-3.
Klauk, H. U. 2007. Low voltage organic thin film transistors with large transconductance. Journal of Applied Physic , 074514-1–074514-7.
Kumar, B. B. 2014. Organic Thin Film Transistors : Structures, Models, Materials, Fabrication, and Applications: A Review. Polymer Reviews , 33-111.
Li, J. Q.-P. 2008. High-Performance Thin-Film Transistors from Solution-Processed Dithienothiophene Polymer Semiconductor Nanoparticles. Chemistry of Materials , 2057.
Liu, R. L. 2010. Low-operating-voltage polymer thin-film transistors based on poly (3-hexylthiophene) with hafnium oxide as the gate dielectric. IEEE Transactions on Device and Materials Reliability , 233-237.
Marinov, O. D. 2009. Organic thin film transistors: Part I. IEEE Trans. Electron Devices , 2952–2961.
McKinnon, M. 2014. Thermogravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC). London: University of Maryland.
Nelson, D. J. 2001. Correlation of Relative Rates of PdCl2 Oxidation of Functionalized Acyclic Alkenes versus Alkene Ionization Potentials, HOMOs, and LUMOs. Journal of American Chemical Society , 1564-1568.
Ortiz, R. P. 2010. High-k organic, inorganic, and hybrid dielectrics for low-voltage organic field-effect transistors. Chemical Review , 205-239.
Qiao, Y. W.-L. 2012. Synthesis, experimental and theoretical characterization, and field-effect transistor properties of a new class of dibenzothiophene derivatives: From linear to cyclic architectures. Journal of Materials Chemistry , 1313.
Shekar, B. C. 2004. Organic thin film transistors: Materials, processes, and devices. Korean Journal Chemistry of Engineering , 267-285.
Sichina, W. 2007. Characterization of Polymers Using TGA. New York: Perkin Elmer Instruments.
Someya, T. E 2002. Vapor sensing with alpha, omega-dihexylquarterthiophene field effect transistor substrates. Chemistry Material , 3079 - 3081.
Stella, M. 2009, December. Study of Organic Semiconductor for Device Application. Barcelona.
Zaumseil, J. A. 2007. Electron and Ambipolar Transport in Organic Field-Effect Transistors. Chemical Review , 1296-1323. |
| 指導教授 |
陳銘洲(Ming-Chou Chen)
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審核日期 |
2016-7-27 |
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