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Controlled Doping of Organic Semiconductors and 2D Materials with Molecular Reductants and Oxidants

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Controlled Doping of Organic Semiconductors and 2D Materials with Molecular Reductants and Oxidants CONTROLLED DOPING OF ORGANIC SEMICONDUCTORS AND 2D MATERIALS WITH MOLECULAR REDUCTANTS AND OXIDANTS A Thesis Presented to The Academic Faculty by Siyuan Zhang In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the School of Chemistry and Biochemistry Georgia Institute of Technology August 2016 © Siyuan Zhang 2016 CONTROLLED DOPING OF ORGANIC SEMICONDUCTORS AND 2D MATERIALS WITH MOLECULAR REDUCTANTS AND OXIDANTS Approved by: Dr. Seth R. Marder, Advisor Dr. David M. Collard School of Chemistry and Biochemistry School of Chemistry and Biochemistry Georgia Institute of Technology Georgia Institute of Technology Dr. John Reynolds Dr. Zhigang Jiang School of Chemistry and Biochemistry School of Physics Georgia Institute of Technology Georgia Institute of Technology Dr. Jean-Luc Brédas Solar and Photovoltaics Engineering Research Center, Physical Science and Engineering Division King Abdullah University of Science and Technology Date Approved: May 23, 2016 To my parents and my future. ACKNOWLEDGEMENTS My deepest gratitude is to my advisor, Dr. Seth Marder, for supporting me during the past four and half years. I have been very fortunate to have an advisor who gave me not only the guidance to conduct research and critical thinking, but also the freedom to explore on my own. He has been supportive throughout my whole Ph.D., and I hope that I could be able to command an audience as well as he can someday. I am also very grateful to Dr. Steve Barlow for his scientific advice and knowledge. He is always available to provide many insightful discussions and suggestions. I am also thankful to Dr. Tim Parker for helping with instruments in the lab and useful suggestions for this dissertation. I would also like to thank the members of my Ph.D. committee: Dr. John Reynolds, Dr. Jean-Luc Brédas, Dr. David Collard, and Dr. Zhigang Jiang, for their helpful suggestions and career advice. I feel grateful that I met many good mentors, who were very open with their knowledge and experience, especially Dr. Swagat Mohapatra and Dr. Sergio Paniagua in Marder group, who showed me how to do air-sensitive synthesis and surface characterization; Dr. José Baltazar and Dr. Hossein Sojoudi, who trained me on cleanroom photolithography, and graphene growth and transfer techniques; and Marcel Said, for showing me how to fabricate organic solar cells. I would like to acknowledge and thank my surface modification subgroup members Dr. Anthony Giordano, Dr. O’Neil Smith, Rebecca Hill, Hyekyung Kim, and Federico Pulvirenti for their support and helpful discussions, and thanks to my mentees, Catherine Robinson, Kodzo Deku iv and Kelsey Rainey, who were always enthusiastic about learning science. I am also indebted to the rest of the Marder Group, from whom I have received much help during my graduate studies. Particularly, I would like to acknowledge Dr. Raghunath R. Dasari, Dr. Yadong Zhang, Dr. Junxiang Zhang, Fadi Jradi, Dr..Kostiantyn Ziabrev, Dr. Iryna Davydenko, Janos Simon, Matthew Copper, Carolyn Buckley, and Xiaochu Ba. I also appreciate Dr. Denise Bale and Walaa Compton for their support to guarantee the whole group functions in a well-organized manner. Outside of the Marder group, I would like thank Dr. John Reynolds, Dr. Samuel Graham, and Dr. Elsa Reichmanis, for their guidance and allowing me to use their lab resources for various studies; especially big thanks to Dr. Jean-Luc Brédas and the members of his group, Dr. Chad Risko, Dr. Hong Li and Junghyun Noh for helping with complex calculations to complement experimental results. I also want to acknowledge collaborators from other departments, including Meng-Yen Tsai and Dr. Alexey Tarasov from Materials Science and Engineering, Dr. Boyi Fu and Dr. Gang Wang at Chemical Engineering, Dr. Hyungchul Kim at Mechanical Engineering, Yuxuan Jiang at Physics Department, as well as Walter Henderson and Todd Walter who have helped me maintain the Kratos XPS for the past two years. I thank the Center for Organic Photonics and Electronics (COPE) for the fellowship awarded. I am also grateful to have the opportunity to work with groups outside the GT campus: Dr. Ben Naab from Dr. Zhenan Bao’s group at Stanford University; You-Chia Chang from Dr. Theodore B. Norris at University of Michigan; several group members v in Dr. Amassian’s group at King Abdullah University of Science and Technology in Saudi Arbia. All of these experiences have made me a more capable and well-rounded scientist. Most importantly, none of this would have been possible without the love and patience of my family. I am forever grateful that my parents raised me up to be who I am, being adventurous, optimistic, having an open-mind, and never giving up easily; I am thankful that wherever I go, I always meet good people, who are supportive and helpful, and become lifelong good friends; and I appreciate that there is always a new opportunity waiting for me right around the corner. I owe a huge debt of gratitude to all the people who have made this dissertation possible. I will cherish and benefit from my graduate experience for the rest of my life. vi TABLE OF CONTENTS Page ACKNOWLEDGEMENTS iv LIST OF TABLES xii LIST OF FIGURES xiv LIST OF SYMBOLS AND ABBREVIATIONS xxvi SUMMARY xxix CHAPTER 1 Introduction 1 1.1 Flexible electronics 1 1.2 Doping and interface modification fundamentals 6 1.2.1 Electronic band structure 6 1.2.2 Effects of doping on charge transport of semiconductors 8 1.2.3 Effects of doping at interfaces 11 1.3 The state of art for dopants and modifiers 13 1.3.1 Dopants: oxidants and reductants 15 1.3.2 Molecular mono- and few-layer modifiers 23 1.4 Application of dopants and modifiers in flexible electronics 24 1.4.1 Applications in organic electronics 24 1.4.2 Applications in 2D materials 25 1.5 Selected techniques commonly used for doping and surface modification studies 26 1.5.1 Photoelectron spectroscopy 27 1.5.2 Electrical transport measurement 30 1.5.3 Cyclic voltammetry 32 vii 1.5.4 UV/vis/ NIR absorption spectroscopy 33 1.6 Thesis overview 34 1.7 References 36 CHAPTER 2 Synthesis and Characterization of Solution- and Vacuum- Processable Benzimidazole-based Dimer Dopants 49 2.1 Air-stable n-type dopants 49 2.2 Synthesis and characterization of benzimidazole-based monomer and dimer dopants 52 2.2.1 Design and synthesis 52 2.2.2 Characterization of the DMBI dimeric dopants 53 2.3 Characterization of doping effects 60 2.3.1 Doping mechanism under consideration for the DMBI dimer dopants 60 2.3.2 Themodynamic parameters relevant to doping 64 2.3.3 Reaction kinetics for DMBI2 dopants in solution 66 2.3.4 Film doping experiments 80 2.4 Conclusions 82 2.5 Experimental 84 2.5.1 Sample preparation and characterization 84 2.5.2 Synthesis 85 2.5.3 Instrumental 89 2.6 References 93 CHAPTER 3 n- and p-Doping of Graphene and CNTs with Various Solution- processed Redox-active Species 96 3.1 Introduction 96 3.2 Modulation of electronics properties of graphene 98 viii 3.3 Techniques used in this chapter 103 3.4 Selection of dopants and the surface treatment for graphene 107 3.5 n-Doping of mono-layer graphene using molecular dimeric and monomeric reductants 108 3.5.1 Transistor and sheet resistance measurements 108 3.5.2 Effects of doping on the sheet resistance and contact resistance 110 3.5.3 UPS and XPS analysis 114 3.6 p-Doping of mono-layer graphene with various oxidants 121 3.7 n- and p-Doping of multi-layer graphene 129 3.8 n- and p-Doping of CNTs 131 3.9 Conclusions 138 3.10 Experimental 139 3.10.1 Materials and equipments 139 3.10.2 Synthesis and transfer of graphene 141 3.10.3 Device Fabrication of FET and four-point probe devices 143 3.10.4 Preparation of the CNT films 143 3.11 References 146 CHAPTER 4 n- and p-Doping of 2D TMDC Materials 150 4.1 Introduction 150 4.2 Doping studies of MoS2 152 4.2.1 FET characterization 153 4.2.2 Band structure characterization 158 4.2.3 XPS characterization 162 4.2.4 Raman characterization 169 4.3 Doping studies of WSe2 171 ix 4.4 Conclusions 179 4.5 Experimental 180 4.5.1 General details 180 4.5.2 Sample doping treatment 181 4.5.3 Characterization of the samples 181 4.6 References 183 CHAPTER 5 Doped Graphene Electrodes in Organic-semiconductor Devices 188 5.1 Introduction 188 5.2 Graphene electrode diodes with simple sandwich structures 191 5.3 Doped graphene electrodes for OPVs 197 5.4 Doped graphene electrode for organic field-effect transistors 207 5.4.1 Graphene electrode OFETs with vacuum deposited C60 208 5.4.2 Graphene electrode OFETs with solution processed polymers 214 5.5 Conclusions 219 5.6 Experimental 219 5.6.1 General details 219 5.6.2 Device fabrication of graphene electrode diodes and OPVs 220 5.6.3 Device fabrication of graphene electrode OFET 223 5.7 References 227 CHAPTER 6 Conclusions and Outlook 232 6.1 Overview 232 6.2 Design of new dimeric n-dopants 232 6.3 Doping of graphene and its use in organic semiconductors 236 6.4 Doping and chemical functionalization of TMDCs 240 6.5 References 245 x APPENDIX A Benzodithiophene and Benzobisthiazole based Oligomers: Investigation of Photovoltaic Propterties 247 A.1 Introduction 247 A.2 Characterization of BBTz-X and BDT-X 249 A.3 References 267 xi LIST OF TABLES Page Table 2.1 Comparison of Proposed Mechanisms for n-Doping with DMBI Dimers 63 Table 2.2 Electrochemical data,a estimated free energies of reaction with TIPSp and PCBM, DFT-calculated adiabatic ionization energies (IEs) for dimeric and monomeric 2-Y-DMBI compounds, and DFT-calculated dissociation energetics.
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