Synthesis of cyclopentadithiophene based low bandgap oliogomers and polymers

簡易檢索 / 詳目顯示

回結果列表

研究生：	郭子瑞 Kuo, Zi-Rui
論文名稱：	Synthesis of cyclopentadithiophene based low bandgap oliogomers and polymers
指導教授：	堀江正樹 Masaki Horie
口試委員:	蘇安仲 Su, An-Chung 游進陽 Yu, Chin-Yang
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2012
畢業學年度：	100
語文別：	英文
論文頁數：	94
中文關鍵詞：	synthesis 、organic filed effect transistor
相關次數：	點閱：2 下載：0
分享至:	分享至facebook 分享至twitter

查詢本校圖書館目錄查詢臺灣博碩士論文知識加值系統勘誤回報

Conjugated polymers have amazing potential as the components of polymeric light emitting diodes (PLEDs), organic field transistors (OFETs) and organic photovoltaic cells (OPVs). In these conjugated polymers, cyclopentadithiophene based polymers show excellent device performances. In this research, the cyclopentadithiophene analogues have been synthesized and characterized by 1H-NMR and mass spectroscopies. Obtained cyclopentadithiophenes and oligomeric molecules were polymerized by oxidative polymerization or direct arylation. The optical and electrochemical properties of the copolymers were measured by cyclic voltammetry and UV-vis spectroscopy. Hole transporting characteristics particularly mobility of these polymers were observed by OFET devices fabricated from chlorobenzene solutions of these polymers varying annealing temperature.

Chapter 1: Introduction and Literature Survey ................................................................................. 1
1 Introduction of Conjugated Polymer ...................................................................................... 1
2 Principle of the Conductive Mechanism for Conjugated Polymers ....................................... 4
3 The Application of Conjugated Polymers ............................................................................ 11
4 Purpose of This Work ........................................................................................................... 29
Chapter 2: Synthesis, Characterization, and OFET Characteristics of Cyclopentadithiophene and Benzothiadiazole Based Oligomer and Polymers .......................................................................... 31
1 Introduction .......................................................................................................................... 31
2 Synthesis of Oligomer and Polymer-PCPDBT .................................................................... 34
2.1 Synthesis of Oligomer ................................................................................................... 34
2.2 Synthesis of Polymer P(CPDT-BT-CPDT) ................................................................... 37
3 Optical and Electrochemical properties ................................................................................ 39
4 OFET characteristics ............................................................................................................ 40
5 Conclusion ............................................................................................................................ 44
Chapter 3: Synthesis and Characterization of Cyclopentadithiophene and Thienopyrrole-dione Oligomer and Polymers .................................................................................................................. 45
1 Introduction .......................................................................................................................... 45
2 Synthesis of Oligomer and Polymers ................................................................................... 48
2.1 Synthesis of Dibromo- thienopyrrole-dione (dibromo-TPD) ........................................ 49
2.2 Synthesis of CPDT-TPD-CPDT .................................................................................... 51
2.3 Synthesis of Polymer, P(CPDT-TPD-CPDT) ............................................................... 54
2.4 Synthesis of Polymer, P(CPDT-TPD) ........................................................................... 56
3 Optical and Electrochemical Properties of Oligomer and Polymers .................................... 58
4 Thermal Properties of Polymer ............................................................................................ 63
5 Conclusion ............................................................................................................................ 64
Chapter 4: Experimental Section .................................................................................................... 65
1 General Experimental Methods ............................................................................................ 65
IV
2 Synthesis of cyclopentadithiophene (CPDT) ....................................................................... 67
2.1 Bis(2-iodothiophen-3-yl) methanol ............................................................................... 67
2.2 Bis(2-iodothiophen-3-yl)methanone ............................................................................. 68
2.3 Cyclopenta[2,1-b;3,4-b']dithiophen-4-one .................................................................... 68
2.4 4H-Cyclopenta[2,1-b;3,4-b']dithiophene ....................................................................... 69
2.5 4,4-Didodecylcyclopenta[2,1-b;3,4-b']dithiophene ....................................................... 70
2.6 4,4-Diethylhexylcyclopenta[2,1-b;3,4-b']dithiophene ................................................... 71
2.7 Monobromo-4, 4-didodecylcyclopenta[2, 1-b; 3, 4-b']dithiophene ............................... 72
3 Synthesis of thieno[3,4-c]pyrrole-4, 6-dione (TPD)............................................................. 74
3.1 Thieno[3,4-c]furan-1,3-dione ........................................................................................ 74
3.2 Hexyl-5H-thieno[3,4-c]pyrrole-4,6-dione ..................................................................... 74
3.3 Dibromo-5-hexyl-5H-thieno[3,4-c]pyrrole-4,6-dione ................................................... 75
4 Synthesis of oligomers ......................................................................................................... 77
4.1 CPDT-BT-CPDT ........................................................................................................... 77
4.2 CPDT-TPD-CPDT ........................................................................................................ 78
5 Synthesis of polymers ........................................................................................................... 80
5.1 P(CPDT-BT-CPDT) ...................................................................................................... 80
5.2 Synthesis of P(CPDT-TPD)........................................................................................... 81
5.3 Synthesis of P(CPDT-TPD-CPDT) ............................................................................... 82
Chapter 5: Conclusion .................................................................................................................... 87
reference ......................................................................................................................................... 89
                                

reference
1 H. Shirakawa, E. J. Louis, A. G. Macdiarmid, C. K. Chiang, and A. J. Heeger, 'Synthesis of Electrically Conducting Organic Polymers - Halogen Derivatives of Polyacetylene, (Ch)X', Journal of the Chemical Society-Chemical Communications (1977), 578-80
2 C. K. Chiang, C. R. Fincher, Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis, S. C. Gau, and A. G. Macdiarmid, 'Electrical-Conductivity in Doped Polyacetylene', Physical Review Letters, 39 (1977), 1098-101.
3 H. J. Bowley, D. L. Gerrard, and W. F. Maddams, 'Formation of Conjugated Polyenes by Chemical and Thermal-Degradation of Vinyl-Chloride Copolymers and Other Vinyl-Polymers', Makromolekulare Chemie-Macromolecular Chemistry and Physics, 186 (1985), 715-23
4 H. Haberkorn, W. Heckmann, G. Kohler, H. Naarmann, J. Schlag, P. Simak, N. Theophilou, and R. Voelkel, 'Unexpected Properties of Poly(Acetylene) Caused by a Modified Catalyst System and Chemical Modification', European Polymer Journal, 24 (1988), 497-99.
5 A. Kraft, A. C. Grimsdale, and A. B. Holmes, 'Electroluminescent Conjugated Polymers - Seeing Polymers in a New Light', Angewandte Chemie-International Edition, 37 (1998), 402-28.
6 C.Kittle, 'Introduction to Solid State Physics'
7 MICHAEL JAMES FEARN, 'Preparation and Properties of P-N Molecular Junctions'.
8 G.; Van Hutten Hadziioannou, P. F.,, 'Semiconducting Polymers -Chemistry, Physics and Engineering,' 1999).
9 J. L. Bredas, and G. B. Street, 'Polarons, Bipolarons, and Solitons in Conducting Polymers', Accounts of Chemical Research, 18 (1985), 309-15.
10 A. Wadeasa, G. Tzamalis, P. Sehati, O. Nur, M. Fahlman, M. Willander, M. Berggren, and X. Crispin, 'Solution Processed Zno Nanowires/Polyfluorene Heterojunctions for Large Area Lightening', Chemical Physics Letters, 490 (2010), 200-04.
11 Lars Herlogsson, 'Electrolyte-Gated Organic Thin-Film Transistors', ( 2011)
12 G. Horowitz, 'Organic Field-Effect Transistors', Advanced Materials, 10 (1998), 365-77.
13 M. C; Bryce Petty, M. R.; Bloor, D., Introduction to Molecular Electronics, Edward Arnold,, 1995)
14 G. Tzamalis, V. Lemaur, F. Karlsson, P. O. Holtz, M. Andersson, X. Crispin, J. Cornil, and M. Berggren, 'Fluorescence Light Emission at 1 Ev from a Conjugated
90
Polymer', Chemical Physics Letters, 489 (2010), 92-95..
15 Q. M. Zhou, Q. Hou, L. P. Zheng, X. Y. Deng, G. Yu, and Y. Cao, 'Fluorene-Based Low Band-Gap Copolymers for High Performance Photovoltaic Devices', Applied Physics Letters, 84 (2004), 1653-55..
16 N. Blouin, A. Michaud, and M. Leclerc, 'A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells', Advanced Materials, 19 (2007), 2295-+.
17 H. Hoppe, and N. S. Sariciftci, 'Polymer Solar Cells', Photoresponsive Polymers Ii, 214 (2008), 1-86.
18 C. J. Brabec, and J. R. Durrant, 'Solution-Processed Organic Solar Cells', Mrs Bulletin, 33 (2008), 670-75..
19 B. C. Thompson, and J. M. J. Frechet, 'Organic Photovoltaics - Polymer-Fullerene Composite Solar Cells', Angewandte Chemie-International Edition, 47 (2008), 58-77.
20 X. Gong, M.H. Tong, Y.J. Xia, W.Z. Cai, J.S. Moon, Y. Cao, G. Yu, C.L. Shieh, B. Nilsson, A.J. Heeger, 'High-detectivity polymer photodetectors with spectral response from 300 nm to 1450 nm', Science, 325 (2009), 1665–1667.
21 F. Banishoeib, A. Henckens, S. Fourier, G. Vanhooyland, M. Breselge, J. Manca, T.J. Cleij, L. Lutsen, D. Vanderzande, L.H. Nguyen, H. Neugebauer, N.S. Sariciftci, ' Synthesis of poly(2,5-Thienylene Vinylene) and its derivatives: low band gap materials for photovoltaics', Thin Solid Films,516 (2008), 3978– 3988.
22 F. Banishoeib, P. Adriaensens, S. Berson, S. Guillerez, O. Douheret, J. Manca, S. Fourier, T. J. Cleij, L. Lutsen, and D. Vanderzande, 'The Synthesis of Regio-Regular Poly(3-Alkyl-2,5-Thienylene Vinylene) Derivatives Using Lithium Bis(Trimethylsilyl)Amide (Lhmds) in the Dithiocarbamate Precursor', Solar Energy Materials and Solar Cells, 91 (2007), 1026-34.
23 C. Y. Yu, C. P. Chen, S. H. Chan, G. W. Hwang, and C. Ting, 'Thiophene/Phenylene/Thiophene-Based Low-Bandgap Conjugated Polymers for Efficient near-Infrared Photovoltaic Applications', Chemistry of Materials, 21 (2009), 3262-69.
24 W. Yue, Y. Zhao, S. Y. Shao, H. K. Tian, Z. Y. Xie, Y. H. Geng, and F. S. Wang, 'Novel Nir-Absorbing Conjugated Polymers for Efficient Polymer Solar Cells: Effect of Alkyl Chain Length on Device Performance', Journal of Materials Chemistry, 19 (2009), 2199-206.
25 W. Z. Cai, X. Gong, and Y. Cao, 'Polymer Solar Cells: Recent Development and Possible Routes for Improvement in the Performance', Solar Energy Materials and Solar Cells, 94 (2010), 114-27.
26 M. Campoy-Quiles, T. Ferenczi, T. Agostinelli, P. G. Etchegoin, Y. Kim, T. D.
91
Anthopoulos, P. N. Stavrinou, D. D. C. Bradley, and J. Nelson, 'Morphology Evolution Via Self-Organization and Lateral and Vertical Diffusion in Polymer: Fullerene Solar Cell Blends', Nature Materials, 7 (2008), 158-64.
27 M. Reyes-Reyes, K. Kim, and D. L. Carroll, 'High-Efficiency Photovoltaic Devices Based on Annealed Poly(3-Hexylthiophene) and 1-(3-Methoxycarbonyl)-Propyl-1-Phenyl-(6,6)C-61 Blends', Applied Physics Letters, 87 (2005).
28 Y. F. Huang, A. R. Inigo, C. C. Chang, K. C. Li, C. F. Liang, C. W. Chang, T. S. Lim, S. H. Chen, J. D. White, U. S. Jeng, A. C. Su, Y. S. Huang, K. Y. Peng, S. A. Chen, W. W. Pai, C. H. Lin, A. R. Tameev, S. V. Novikov, A. V. Vannikov, and W. S. Fann, 'Nanostructure-Dependent Vertical Charge Transport in Meh-Ppv Films (Vol 17, Pg 2902, 2007)', Advanced Functional Materials, 18 (2008), 3550-50.
29 T. Erb, U. Zhokhavets, G. Gobsch, S. Raleva, B. Stuhn, P. Schilinsky, C. Waldauf, and C. J. Brabec, 'Correlation between Structural and Optical Properties of Composite Polymer/Fullerene Films for Organic Solar Cells', Advanced Functional Materials, 15 (2005), 1193-96
30 C. Y. Yang, J. G. Hu, and A. J. Heeger, 'Molecular Structure and Dynamics at the Interfaces within Bulk Heterojunction Materials for Solar Cells', Journal of the American Chemical Society, 128 (2006), 12007-13.
31 V. D. Mihailetchi, H. X. Xie, B. de Boer, L. J. A. Koster, and P. W. M. Blom, 'Charge Transport and Photocurrent Generation in Poly (3-Hexylthiophene): Methanofullerene Bulk-Heterojunction Solar Cells', Advanced Functional Materials, 16 (2006), 699-708.
32 J. S. Huang, G. Li, and Y. Yang, 'Influence of Composition and Heat-Treatment on the Charge Transport Properties of Poly(3-Hexylthiophene) and [6,6]-Phenyl C-61-Butyric Acid Methyl Ester Blends', Applied Physics Letters, 87 (2005).
33 T. J. Savenije, J. E. Kroeze, X. N. Yang, and J. Loos, 'The Effect of Thermal Treatment on the Morphology and Charge Carrier Dynamics in a Polythiophene-Fullerene Bulk Heterojunction', Advanced Functional Materials, 15 (2005), 1260-66..
34 C. Muller, T. A. M. Ferenczi, M. Campoy-Quiles, J. M. Frost, D. D. C. Bradley, P. Smith, N. Stingelin-Stutzmann, and J. Nelson, 'Binary Organic Photovoltaic Blends: A Simple Rationale for Optimum Compositions', Advanced Materials, 20 (2008), 3510.
35 T. M. Clarke, A. M. Ballantyne, J. Nelson, D. D. C. Bradley, and J. R. Durrant, 'Free Energy Control of Charge Photogeneration in Polythiophene/Fullerene Solar Cells: The Influence of Thermal Annealing on P3ht/Pcbm Blends', Advanced Functional Materials, 18 (2008), 4029-35.
92
36 I. W. Hwang, D. Moses, and A. J. Heeger, 'Photoinduced Carrier Generation in P3ht/Pcbm Bulk Heterojunction Materials', Journal of Physical Chemistry C, 112 (2008), 4350-54.
37 R. C. Hiorns, R. De Bettignies, J. Leroy, S. Bailly, M. Firon, C. Sentein, A. Khoukh, H. Preud'homme, and C. Dagron-Lartigau, 'High Molecular Weights, Polydispersities, and Annealing Temperatures in the Optimization of Bulk-Heterojunction Photovoltaic Cells Based on Poly(3-Hexylthiophene) or Poly(3-Butylthiophene)', Advanced Functional Materials, 16 (2006), 2263-73.
38 Y. Kim, S. Cook, S. M. Tuladhar, S. A. Choulis, J. Nelson, J. R. Durrant, D. D. C. Bradley, M. Giles, I. Mcculloch, C. S. Ha, and M. Ree, 'A Strong Regioregularity Effect in Self-Organizing Conjugated Polymer Films and High-Efficiency Polythiophene: Fullerene Solar Cells', Nature Materials, 5 (2006), 197-203
39 A. J. Moule, and K. Meerholz, 'Controlling Morphology in Polymer-Fullerene Mixtures', Advanced Materials, 20 (2008), 240-+.
40 F. Padinger, R. S. Rittberger, and N. S. Sariciftci, 'Effects of Postproduction Treatment on Plastic Solar Cells', Advanced Functional Materials, 13 (2003), 85-88.
41 M. Al-Ibrahim, O. Ambacher, S. Sensfuss, and G. Gobsch, 'Effects of Solvent and Annealing on the Improved Performance of Solar Cells Based on Poly(3-Hexylthiophene): Fullerene', Applied Physics Letters, 86 (2005)
42 Y. Zhao, Z. Y. Xie, Y. Qu, Y. H. Geng, and L. X. Wang, 'Solvent-Vapor Treatment Induced Performance Enhancement of Poly(3-Hexylthiophene): Methanofullerene Bulk-Heterojunction Photovoltaic Cells', Applied Physics Letters, 90 (2007).
43 W. L. Wang, H. B. Wu, C. Y. Yang, C. Luo, Y. Zhang, J. W. Chen, and Y. Cao, 'High-Efficiency Polymer Photovoltaic Devices from Regioregular-Poly(3-Hexylthiophene-2,5-Diyl) and [6,6]-Phenyl-C-61-Butyric Acid Methyl Ester Processed with Oleic Acid Surfactant', Applied Physics Letters, 90 (2007).
44 G. Dennler, M. C. Scharber, and C. J. Brabec, 'Polymer-Fullerene Bulk-Heterojunction Solar Cells', Advanced Materials, 21 (2009), 1323-38.
45 J. Zaumseil, and H. Sirringhaus, 'Electron and Ambipolar Transport in Organic Field-Effect Transistors', Chemical Reviews, 107 (2007), 1296-323.
46
47 R. D. McCullough, 'The Chemistry of Conducting Polythiophenes', Advanced Materials, 10 (1998), 93-+.
48 A. Assadi, C. Svensson, M. Willander, and O. Inganas, 'Field-Effect Mobility of Poly(3-Hexylthiophene)', Applied Physics Letters, 53 (1988), 195-97.
49 A. Tsumura, H. Fuchigami, and H. Koezuka, 'Field-Effect Transistor with a Conducting Polymer Film', Synthetic Metals, 41 (1991), 1181-84
93
50 J. Paloheimo, H. Stubb, P. Ylilahti, and P. Kuivalainen, 'Field-Effect Conduction in Polyalkylthiophenes', Synthetic Metals, 41 (1991), 563-66.
51 Gamota D. R., et al., (eds.), Printed Organic and Molecular Electronics, Kluwer Academic, New York, (2004)
52 C. Kitamura, S. Tanaka, and Y. Yamashita, 'Design of Narrow-Bandgap Polymers. Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and O-Quinoid-Acceptor Units', Chemistry of Materials, 8 (1996), 570-78.
53 A. J. Heeger, 'Semiconducting Polymers: The Third Generation', Chemical Society Reviews, 39 (2010), 2354-71.
54 E. Menard, M. A. Meitl, Y. G. Sun, J. U. Park, D. J. L. Shir, Y. S. Nam, S. Jeon, and J. A. Rogers, 'Micro- and Nanopatterning Techniques for Organic Electronic and Optoelectronic Systems', Chemical Reviews, 107 (2007), 1117-60.
55 H. Usta, G. Lu, A. Facchetti, and T. J. Marks, 'Dithienosilole- and Dibenzosilole-Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors', Journal of the American Chemical Society, 128 (2006), 9034-35.
56 M. R. Andersson, D. Selse, M. Berggren, H. Jarvinen, T. Hjertberg, O. Inganas, O. Wennerstrom, and J. E. Osterholm, 'Regioselective Polymerization of 3-(4-Octylphenyl)Thiophene with Fecl3', Macromolecules, 27 (1994), 6503-06.
57 H. N. Tsao, D. M. Cho, I. Park, M. R. Hansen, A. Mavrinskiy, D. Y. Yoon, R. Graf, W. Pisula, H. W. Spiess, and K. Mullen, 'Ultrahigh Mobility in Polymer Field-Effect Transistors by Design', Journal of the American Chemical Society, 133 (2011), 2605-12.
58 M. Horie, L. A. Majewski, M. J. Fearn, C. Y. Yu, Y. Luo, A. M. Song, B. R. Saunders, and M. L. Turner, 'Cyclopentadithiophene Based Polymers-a Comparison of Optical, Electrochemical and Organic Field-Effect Transistor Characteristics', Journal of Materials Chemistry, 20 (2010), 4347-55.
59 H. Usta, G. Lu, A. Facchetti, and T. J. Marks, 'Dithienosilole- and Dibenzosilole-Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors', Journal of the American Chemical Society, 128 (2006), 9034-35.
60 C. Soci, I. W. Hwang, D. Moses, Z. Zhu, D. Waller, R. Gaudiana, C. J. Brabec, and A. J. Heeger, 'Photoconductivity of a Low-Bandgap Conjugated Polymer', Advanced Functional Materials, 17 (2007), 632-36
61 H. N. Tsao, D. M. Cho, I. Park, M. R. Hansen, A. Mavrinskiy, D. Y. Yoon, R. Graf, W. Pisula, H. W. Spiess, and K. Mullen, 'Ultrahigh Mobility in Polymer Field-Effect Transistors by Design', Journal of the American Chemical Society, 133 (2011), 2605-12.
62 M. Lafrance, C. N. Rowley, T. K. Woo, and K. Fagnou, 'Catalytic Intermolecular Direct Arylation of Perfluorobenzenes', Journal of the American Chemical Society,
94
128 (2006), 8754-56.
63 L. Ackermann, P. Novak, R. Vicente, and N. Hofmann, 'Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage', Angewandte Chemie-International Edition, 48 (2009), 6045-48.
64 Q. F. Wang, R. Takita, Y. Kikuzaki, and F. Ozawa, 'Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-Hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-Hexylthiophene)', Journal of the American Chemical Society, 132 (2010), 11420-21.
65 A. Facchetti, L. Vaccaro, and A. Marrocchi, 'Semiconducting Polymers Prepared by Direct Arylation Polycondensation', Angewandte Chemie-International Edition, 51 (2012), 3520-23.
66 W. Lu, J. Kuwabara, and T. Kanbara, 'Polycondensation of Dibromofluorene Analogues with Tetrafluorobenzene Via Direct Arylation', Macromolecules, 44 (2011), 1252-55.
67 S. Kowalski, S. Allard, and U. Scherf, 'Synthesis of Poly(4,4-Dialkyl-Cyclopenta[2,1-B:3,4-B ']Dithiophene-Alt-2,1,3-Benzothiadiazole) (Pcpdtbt) in a Direct Arylation Scheme', Acs Macro Letters, 1 (2012), 465-68.
68 Q. T. Zhang, and J. M. Tour, 'Low Optical Bandgap Polythiophenes by an Alternating Donor/Acceptor Repeat Unit Strategy', Journal of the American Chemical Society, 119 (1997), 5065-66.
69 C. B. Nielsen, and T. Bjornholm, 'New Regiosymmetrical Dioxopyrrolo-and Dihydropyrrolo-Functionalized Polythiophenes', Organic Letters, 6 (2004), 3381-84.
70 Y. J. Cheng, S. H. Yang, and C. S. Hsu, 'Synthesis of Conjugated Polymers for Organic Solar Cell Applications', Chemical Reviews, 109 (2009), 5868-923.
71 Y. P. Zou, A. Najari, P. Berrouard, S. Beaupre, B. R. Aich, Y. Tao, and M. Leclerc, 'A Thieno[3,4-C]Pyrrole-4,6-Dione-Based Copolymer for Efficient Solar Cells', Journal of the American Chemical Society, 132 (2010), 5330-+.
72 X. G. Guo, H. Xin, F. S. Kim, A. D. T. Liyanage, S. A. Jenekhe, and M. D. Watson, 'Thieno[3,4-C]Pyrrole-4,6-Dione-Based Donor-Acceptor Conjugated Polymers for Solar Cells', Macromolecules, 44 (2011), 269-77.

全文公開日期本全文未授權公開 (校內網路)
全文公開日期本全文未授權公開 (校外網路)
全文公開日期本全文未授權公開 (國家圖書館：臺灣博碩士論文系統)

簡易檢索 / 詳目顯示

相關論文