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1 Solution-Processable Organic Semiconducting SOLUTION-PROCESSABLE ORGANIC SEMICONDUCTING MATERIALS FOR PHOTOVOLTAIC APPLICATIONS By JIANGUO MEI A DISSERTATION PRESENTED TO THE GRADUATE SCHOOL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY UNIVERSITY OF FLORIDA 2010 1 © 2010 Jianguo Mei 2 To my wife, our soon-to-come son, and my parents 3 ACKNOWLEDGMENTS I would like to thank my advisor Dr. John R Reynolds. After four years of practicing “wet” chemistry in the lab, I am still optimistic and enthusiastic about what I am doing, for which he deserves a lot of credit. He has been a good advisor, wise listener and generous supporter. He made my experience at UF enjoyable and helped shape me in many aspects. As a teaching coordinator for his Organic Chemistry class, he taught me how to make and grade an exam, organize an office hour and communicate with students. As a researcher in the lab, he trained me how to properly write a technical report and a grant, draft a cover letter and a manuscript, review a scientific paper and give a public presentation. As an individual person, I gratefully benefited from the dedication and caring nature he demonstrated. He was always there to advice and support when it came to my career development. I would also like to thank the members of my committee, Prof. Kirk S. Schanze, Prof. Daniel R. Talham, Prof. Ronald K. Castellano, Prof. Franky So, and Prof. Jiangeng Xue, for contributing their valuable time and expertise to my education at the University of Florida. I also wish to thank Prof. Ken Wagener for the many thoughtful pieces of advice and stimulating discussions he has given over the years, and for his efforts to create an excellent environment in the Butler Polymer Laboratory. I am also grateful to my many collaborators who have contributed to the projects I have carried out at UF. Dr. Kirk Schanze, Dr. Young-Gi Kim, Dr. Katsu Ogawa, Dr. Nathan Heston and Dr. Jarrett Vella contributed significantly to my very first project on platinum-acetylide low bandgap polymers. Dr. Schanze has been a passionate supporter and on my reference list since then. Dr. Nathan Heston, Dr. Svetlana Vasilyeva, Dr. Michael F Durstock (AFRL) and Christopher A Bailey (AFRL) helped to develop the project on the vinylene-linked donor- acceptor conjugated polymers. Dr. Bernard Kippelen, Dr. Shree Prakash Tiwari, Dr. Hyeunseok 4 Cheun and Jaewon Shim at Georgia Tech contributed to the projects on small molecule-based field-effect transistors and organic solar cells. Dr. Franky So, Dr. Jegadesan Subbiah and Dr. Kaushik Roy Choudhury in Department of Material Science and Engineering at UF have worked on polymer-based devices together with me. And I also wish to thank Dr. Franky So for his insightful advice, hospitality and willingness to serve as my reference. Dr. Ronald Castellano made great efforts to the project on self-assembled amphiphilic cruciform shaped oligothiophenes. I also thank him for the valuable advice and serving as a reference. I am deeply indebted to my two Reynolds group collaborators: “GRIT fellow” Romain Stalder and “GRIT fellow” Kenneth Graham. We have worked together on a number of projects, and our collaborations still keep moving ahead. I would also like to thank Brian Atiken in the Wagener group. We have worked closely together on regioregular electroactive polyolefins, the “first” collaboration between the two groups. Many people have been influential in my development as a graduate student. My master’s degree advisor Prof. Shaoming Yu at the Hefei University of Technology encouraged and brought me into the scientific field. With his unselfish support and encouragement I was able to step out and make my move to the States. Prof. Steven P Nolan at the University of New Orleans was actually the first one who trained me as a chemist. Knowing that I would transfer to UF one year later, he still accepted me into his group, and provided me with various training opportunities. In his group, I, formerly trained as a chemical engineer, was trained by a number of experienced chemists, including Dr. Oscar Navarro, Dr. Roy A. Kelly, III, Dr. Natalie M. Scott, Dr. Nicolas Marion, Dr. Rohit Singh. I still remembered when Dr. Kelly showed me how to use a cannula to transfer liquids under inert atmosphere and Dr. Singh demonstrated the proper way to make a TLC spot. 5 After joining the Reynolds group, many people contributed to my work and made my stay at UF a pleasant journey of learning. I am grateful for the help and advice over the years from Dr. Stefan Ellinger, Dr. Prasad Taranekar, Dr. Robert Brookins, Dr. Timothy Steckler, Dr. Ryan Walzack, Dr. Nathan Heston, Dr. Aubrey Dyer, Dr. Svetlana Vasilyeva, Dr. Dan Patel, Dr. Mike Craig, Dr. Chad Amb, Dr. Pierre Beaujuge and Pengjie Shi. I also thank the younger generation of the Butler Lab members, Ken Graham, Romain Stalder, David Liu, Frank Arroyave, Yuying Wei, Bora Inci, Brian Atiken and Paula Delgado for their service and friendship. Special thanks go to Coralie Richard for occasionally bringing me her delicious home-made cookies. I would also like to show my appreciation to Cheryl Googins, Gena Borrero and Sara Klossner for their great service, which made everything easy and convenient. Additionally, I will take this opportunity to thank George and Jospehine Butler. I have enormously benefited from the environment and facility brought by their generous gifts. I am also grateful for the Butler Polymer Award funded by the Butler Foundation. Finally, I would like to thank my parents Shixin Mei and Jinhua Zhu, and my wife, Yanrong Wu for their unconditional support and love. I am extremely indebted to my wife, who is carrying our first baby hundreds of miles away and asks little from me while I am working to prepare this dissertation. We are looking forward to the future and our soon-to-come son. 6 TABLE OF CONTENTS page ACKNOWLEDGMENTS ...............................................................................................................4 LIST OF TABLES .........................................................................................................................10 LIST OF FIGURES .......................................................................................................................11 LIST OF ABBREVIATIONS ........................................................................................................19 ABSTRACT ...................................................................................................................................21 CHAPTER 1 INTRODUCTION ..................................................................................................................24 1.1 Organic Semiconducting Materials ..................................................................................24 1.1.1 Inorganic and Organic Semiconducting Materials ...............................................25 1.1.1.1 Conductivity ..........................................................................................26 1.1.1.2 Polaron, bipolaron and soliton ..............................................................28 1.1.1.3 The width of energy bands ....................................................................32 1.1.1.4 Charge carrier, charge transport, mobility and charge trap ...................32 1.1.2 P-, N-type and Ambipolar Semiconducting Materials .........................................35 1.1.3 Molecular and Polymeric Semiconducting Materials ..........................................36 1.2 Bandgap Engineering ........................................................................................................38 1.2.1 Bandgap Control ..................................................................................................39 1.2.2 The Donor-Acceptor Approach ............................................................................40 1.3 Photovoltaic Devices ........................................................................................................42 1.3.1 Silicon-Based Solar Cells .....................................................................................43 1.3.2 Organic Solar Cells ..............................................................................................47 1.3.3 Bilayer Organic Solar Cells .................................................................................53 1.3.4 Bulk Heterojunction Organic Solar Cells ............................................................54 1.3.4.1 Polymer/PCBM bulk heterojunction solar cells ....................................55 1.3.4.2 Polymer/polymer bulk heterojunction solar cells .................................62 1.3.4.3 Molecular bulk heterojunction solar cells .............................................64 1.3.4.4 Organic-inorganic hybrid solar cells .....................................................66 1.3.5 Tandem Bulk-heterojucntion Solar Cells .............................................................68 1.4 Objectives of this Dissertation ..........................................................................................69 2 EXPERIMENTAL METHODS AND CHARACTERIAZATIONS .....................................71 2.1 Materials Characterization ............................................................................................71 2.1.1 Structural Characterization ..................................................................................71 2.1.2 Molecular Weight Characterization .....................................................................71
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