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[Thesis Title Goes Here] ADDITIVES FOR ACTIVE LAYER DESIGN & TRAP PASSIVATION IN ORGANIC PHOTOVOLTAICS A Dissertation Presented to The Academic Faculty by Marcel M. Said 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 COPYRIGHT © MARCEL M. SAID 2016 ADDITIVES FOR ACTIVE LAYER DESIGN & TRAP PASSIVATION IN ORGANIC PHOTOVOLTAICS Presented to: Dr. Seth R. Marder, Advisor Dr. David Bucknall, Advisor School of Chemistry and Biochemistry School of Engineering and Physical Georgia Institute of Technology Sciences Heriot-Watt University Dr. Jean-Luc Brédas Dr. Bernard Kippelen School of Physical Science and Engineering School of Electrical Engineering King Abdullah University of Science and Georgia Institute of Technology Technology Dr. John R. Reynolds School of Chemistry and Biochemistry School of Materials Science and Engineering Georgia Institute of Technology Date Approved: June 19, 2016 I dedicate this thesis to my parents, whose support of me and my dreams has never wavered ACKNOWLEDGEMENTS As proud as I am of the work completed in the chapters of this thesis, I am prouder still to have earned the support of so many talented and knowledgeable individuals, without whom this achievement would not have been possible. First, I would like to thank my advisor Prof. Seth Marder, who granted me the opportunity to work in his laboratory in advance of my first semester, creating and fostering my passion for the field of organic photovoltaic devices. Throughout my years under his tutelage, he has tirelessly worked to sculpt me, in my thoughts and actions, into a scientist, however difficult the transition may have been. For his efforts I am eternally grateful. Next, I would like to thank Prof. David Bucknall, who primarily introduced me to the field of material science, and whose advisement has never ceased to renew my optimism in the face of daunting and complex scientific challenges. I would also like to acknowledge Prof. Bernard Kippelen, for teaching me the fundamentals of organic photovoltaic devices and for allowing me to benefit from his facilities and the expertise of his group members when I had neither at my disposal, Prof. John Reynolds, for kindly welcoming me to work alongside his students and forming the Solid State Device Laboratory, a partnership that moved my research forward immensely, and Prof. Jean-Luc Brédas, for his invaluable guidance and discussions during my graduate career. Of course, I recognize that I benefit from the efforts of my committee members beyond our direct interactions, and so I also thank them for their continual work within the university, as well as their departments and scientific centers, such as COPE and GTPN, which has made my graduate career possible. There are many members of the Marder group, past and present, without whom I could not have made it to this point. First, I owe a great debt of gratitude to Dr. Stephen iv Barlow, who, over many discussions and reviews of my research, has helped me to build a greater understanding of the fundamental concepts behind it and how to articulate them. My thanks go to Dr. Tim Parker for his assistance in my thesis, as well as his daily efforts in keeping our laboratory functioning. I also must thank Dr. Denise Bale and Walaa Compton, as I, and certainly many others, would not have made it through graduate school without their support. I must acknowledge my close peers, Dr. Fadi Jradi, Dr. Karttikay Moudgil, Dr. Siyuan Zhang, Matthew Cooper, and Janos Simon; their passion for philosophical discussion and constructive criticism has greatly developed my capacity for critical-thinking. Additionally, I must thank Dr. Maria-Cristina Rumi, Dr. Benjamin Wunsch, Dr. Jassem Abdallah, Dr. Dun-Yen Kang, Dr. Yadong Zhang, Dr. Tissa Sajoto, Dr. Swagat Mohapatra, Dr. Yulia Getmanenko, Dr. Raghunath Dasari, Dr. Junxiang Zhang, Dr. Anthony Giordano, Dr. O’Neil Smith, Dr. Sergio Paniagua and many, many others for their instruction, support, and friendship. My research could not have been brought to fruition without the assistance of my collaborators and others in my department. For teaching me to fabricate my first efficient photovoltaic devices, I must recognize Dr. Michael Durstock and Dr. Benjamin Leever at the Wright Patterson Air Force Base. For their assistance in the Solid State Device Laboratory and with X-ray scattering analysis, I thank Dr. Caroline Grand, Dr. Nabankur Deb, and Jeffrey Hernandez from the Reynolds and Bucknall groups. For welcoming me as a member of their group, teaching me the finer details of highly efficient organic photovoltaic devices, and for the many projects that we built together, I acknowledge Prof. Aram Amassian, Dr. Kui Zhao, Dr. Lethy Jagadamma, Guy Ngongang, Hanlin Hu, Ahmed Mansour, Ahmad Kirmani, and Rahim Munir at the King Abdullah University of Science v and Technology. I would also like to thank Dr. Cameron Tyson and Dr. Kenyetta Johnson for their invaluable guidance. Finally, none of this would have been possible without the support of my family. The hard work and sacrifice of my parents is the sole reason that my brother and I have had the ability to pursue our goals without hardship. Mom, Dad, and Oliver, this is for you. vi TABLE OF CONTENTS ACKNOWLEDGEMENTS .......................................................................... IV LIST OF TABLES ........................................................................................ XI LIST OF FIGURES ..................................................................................... XII LIST OF ABBREVIATIONS & SYMBOLS ......................................... XVIII SUMMARY ................................................................................................. XX INTRODUCTION................................................................ 1 1.1 Reflection on Organic Photovoltaic Devices – Theory & History ..................... 1 1.1.1 Organic Semiconductors .................................................................................... 1 1.1.2 Foundations of Organic Photovoltaics ............................................................... 7 1.1.3 Electronic Processes in Organic Heterojunction Photovoltaics ....................... 10 1.1.4 Rise of the Bulk Heterojunction....................................................................... 16 1.1.5 Modern Techniques for Morphological Control in OPV Active Layers ......... 20 1.2 Fundamental Techniques for Organic Photovoltaic Device and Material Characterization ............................................................................................................ 22 1.2.1 Organic Photovoltaics – Device Fabrication and Measurements .................... 22 1.2.2 Incident Photon-to-Current Conversion Efficiency ......................................... 30 1.2.3 Electrical Conductivity and Mobility ............................................................... 33 1.2.4 Photoelectron Spectroscopy ............................................................................. 39 1.2.5 Atomic Force Microscopy ............................................................................... 45 1.2.6 Grazing-Incidence X-Ray Scattering & Diffraction ........................................ 47 1.3 Conclusion ........................................................................................................ 52 1.4 Works Cited ...................................................................................................... 53 DUAL-ACCEPTOR PERYLENE DIIMIDE TERNARY BULK HETEROJUNCTIONS IN ORGANIC PHOTOVOLTAIC DEVICES 77 2.1 Introduction ....................................................................................................... 77 2.1.1 Ternary Bulk Heterojunctions in Organic Photovoltaics ................................. 77 2.1.2 Dual-Acceptor Ternary Bulk Heterojunctions ................................................. 78 vii 2.2 Methods & Results ............................................................................................ 80 2.2.1 Synthesis .......................................................................................................... 80 2.2.2 Differential Scanning Calorimetry ................................................................... 83 2.2.3 Scanning Electron Microscopy ........................................................................ 86 2.2.4 Grazing-Incidence Wide Angle X-ray Diffraction and Scattering .................. 89 2.2.5 Organic Photovoltaic Devices .......................................................................... 92 2.2.6 Atomic Force Microscopy ............................................................................... 94 2.2.7 Electrochemical Thin Film Studies ................................................................ 100 2.2.8 Time-Of-Flight Electron Mobility ................................................................. 103 2.3 Conclusion ...................................................................................................... 107 2.4 Works Cited .................................................................................................... 110 ULTRA-LOW P-DOPING OF POLY(3- HEXYLTHIOPHENE) AND ITS IMPACT ON POLYMER AGGREGATION AND PHOTOVOLTAIC PERFORMANCE ................116 3.1 Introduction ..................................................................................................... 116 3.1.1 Origins of Electrical Doping .........................................................................
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