ORGANIC LIGHT EMITTING DIODE – MATERIAL, PROCESS AND DEVICES Edited by Seung Hwan Ko Organic Light Emitting Diode – Material, Process and Devices Edited by Seung Hwan Ko Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2011 InTech All chapters are Open Access articles distributed under the Creative Commons Non Commercial Share Alike Attribution 3.0 license, which permits to copy, distribute, transmit, and adapt the work in any medium, so long as the original work is properly cited. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published articles. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Iva Lipovic Technical Editor Teodora Smiljanic Cover Designer Jan Hyrat Image Copyright demarcomedia, 2010. Used under license from Shutterstock.com First published July, 2011 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechweb.org Organic Light Emitting Diode – Material, Process and Devices, Edited by Seung Hwan Ko p. cm. ISBN 978-953-307-273-9 free online editions of InTech Books and Journals can be found at www.intechopen.com Contents Preface IX Part 1 OLED Materials 1 Chapter 1 Synthesis, and Photo- and Electro-Luminescent Properties of Phosphorescent Iridium- and Platinum-Containing Polymers 3 Yuji Koga and Kouki Matsubara Chapter 2 Synthesis and Photophysical Properties of Pyrene-Based Multiply Conjugated Shaped Light-Emitting Architectures: Toward Efficient Organic-Light-Emitting Diodes 21 Jian-Yong Hu and Takehiko Yamato Chapter 3 Organometallic Materials for Electroluminescent and Photovoltaic Devices 61 Boris Minaev, Xin Li, Zhijun Ning, He Tian and Hans Ågren Chapter 4 High Efficiency Red Phosphorescent Organic Light-Emitting Diodes with Simple Structure 101 Ramchandra Pode and Jang Hyuk Kwon Chapter 5 Organic Field-Effect Transistors Using Hetero-Layered Structure with OLED Materials 147 Ken-ichi Nakayama, Yong-Jin Pu, Junji Kido and Masaaki Yokoyama Chapter 6 Organic Light Emitting Diodes Based on Novel Zn and Al Complexes 161 Petia Klimentova Petrova, Reni Lyubomirova Tomova and Rumiana Toteva Stoycheva-Topalova Part 2 OLED Processes and Devices 193 Chapter 7 Unconventional, Laser Based OLED Material Direct Patterning and Transfer Method 195 Seung Hwan Ko and Costas P. Grigoropoulos VI Contents Chapter 8 Interlayer Processing for Active Matrix Organic Light Emitting Diode (OLED) Displays 215 Peter Vicca, Soeren Steudel, Steve Smout, Kris Myny, Jan Genoe, Gerwin G.H. Gelinck and Paul Heremans Chapter 9 Transparent Conductive Oxide (TCO) Films for Organic Light Emissive Devices (OLEDs) 233 Sunyoung Sohn and Hwa-Min Kim Chapter 10 Micro-Cavity in Organic Light-Emitting Diode 275 Young-Gu Ju Chapter 11 Fast-Response Organic Light-Emitting Diode for Interactive Optical Communication 291 Takeshi Fukuda and Yoshio Taniguchi Chapter 12 Effect of High Magnetic Field on Organic Light Emitting Diodes 311 Toshihiro Shimada Preface Organic light-emitting diodes (OLED) are playing a major role in information technol- ogy (IT) by providing the promise of further expanding the use of digital displays through making display fabrication technology lower in cost and higher in perfor- mance to replace liquid crystal displays (LCD). Due to various attractive features such as high contrast, high brightness, large color gamut and thin structure, various sized OLED displays from small-sized mobile phone display to large-sized TV display have already begun to be mass-produced. This book is a collection of state-of-the-art works intended to cover theoretical and ex- perimental aspects of OLED from material synthesis and characterization (Chapter 1- 6) to actual process development and devices applications (Chapter 7-12). Each chap- ter features remarkable breakthrough on OLED and provides latest scientific knowledge and leading-edge technology. They offer research agenda and accelerate the research, development and distribution of OLED. I expect that this book will be useful to encourage further experimental and theoretical research in OLED. In closing, I wish to express my sincere gratitude to the contributing authors of each chapter, publishing process manager Ms. Iva Lipovic, and the publishing staffs. In par- ticular, I am deeply grateful to Prof. Costas P. Grigoropoulos (UC Berkeley), Dr. Hee K. Park (AppliFlex), Dr. Ming-Tsang Lee (Lawrence Berkeley National Laboratory), Dr. Heng Pan (Applied Materials. Inc) for valuable suggestions. I dedicate this book to my parents and my wife, Ms. Hyun Jung Kim. Dr. Seung Hwan Ko Applied Nano Technology and Science (ANTS) Lab Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Korea [...]... host polymer and the guest chromophore is expected that intramolecular electron transfer occurs easily Here we developed new 10 Organic Light Emitting Diode – Material, Process and Devices Fig 5 1H NMR spectra in CD2Cl2 for (a) 14, (b) ligand polymer 1, and (c) metallopolymer 5 in the aromatic region (a) (b) (c) (d) (e) Fig 6 1H NMR spectra in CD2Cl2 for (a) 2a, (b) 7a, (c) 2b, (d) 7b and (e) 14 in... almost the same as that of the monomeric metal complex The iridium–containing polymers 10 and 12 exhibited the similar luminescent spectra to that for the monomeric analog 14, whereas the spectra for the platinum polymers 11 and 13 showed a characteristic strong band due to the conjugated 14 Organic Light Emitting Diode – Material, Process and Devices main chain under 570 nm in addition to the luminescence... Polym Chem 2004, 42, 415 3–4 160; (f) Deng, L.; Furuta, P T.; Garon, S.; Li, J.; Kavulak, D.; Thompson, M E.; Fre´chet, J M J Chem Mater 2006, 18, 38 6–3 95; (g) Schulz, G L.; Chen, X.; Chen, S.-A.; Holdcroft, S Macromolecules 2006, 39, 915 7–9 165; (h) Aamer, K A.; Tew, G N J Polym Sci Part A: Polym Chem 2007, 45, 110 9–1 121 20 Organic Light Emitting Diode – Material, Process and Devices [8] Koga, Y.; Yoshida,... section, the synthesis and photophysical properties of two types of functionalized pyrenebased light- emitting monomers, namely, pyrene-cored organic light- emitting monomers and pyrene-functionalized PAHs-cored organic light- emitting monomers were fully presented In particular, the use of these light- emitting monomers as efficient emitters in OLEDs will be discussed in detail Synthesis and Photophysical... ligand copolymers 2a and 2b, which have different Vp contents, 4.7 and 15 mol%, respectively The content of Vp was determined by absorption coefficient ratio for PVK at 345 nm in CHCl3 (Table 1) The ligand copolymers 2a and 2b were prepared in the presence of AIBN.12 The reaction of these 8 Organic Light Emitting Diode – Material, Process and Devices copolymers with [IrCl(piq)2]2 (3) in CH2Cl2 gave red solutions,... performance The devices G and J, in which the Vc copolymer was involved instead of MMA copolymer, showed unexpected high threshold voltage, despite PVK was known as conductive host polymer in EL devices. 11 The device S, containing the monomeric 14-doped PVK, also performed high threshold voltage, suggesting that PVK does not perform enough 16 Organic Light Emitting Diode – Material, Process and Devices conductivity... X3 = Br, X4 = H X4 1 Scheme 1 Electrophilic bromination of pyrene (1) X3 2 2e: X1 = X2 = X3 = X4 = Br 24 Organic Light Emitting Diode – Material, Process and Devices 3.1.1 Alkynyl-functionalized pyrene-cored light- emitting monomers Acetylene has been widely applied for linking -conjugated units and for effectively extending the -conjugation length The progress of such -conjugated materials by means... found that structure of backbone host polymer is quite important for efficient luminescence and low driving voltage in these devices We also demonstrated that the good EL performance was provided when the guest unit directly bound to the host polymer 18 Organic Light Emitting Diode – Material, Process and Devices 7 Experimental details 7.1 Synthesis of pyridine-capped conjugated copolymers As a typical... Pyrene-Based Multiply Conjugated Shaped Light- Emitting Architectures: Toward Efficient Organic- Light- Emitting Diodes 23 3.1 Pyrene-cored organic light- emitting monomers Although pyrene and its derivatives have been widely used as fluorescence probes in many applications, there are two major drawbacks using pyrene as a fluorescence probe: One is the absorption and emission wavelengths of the pyrene monomer... K J Polym Sci Part A: Polym Chem 2006, 44, 420 4–4 213 2 Synthesis and Photophysical Properties of Pyrene-Based Multiply Conjugated Shaped Light- Emitting Architectures: Toward Efficient Organic- Light- Emitting Diodes 1Department Jian-Yong Hu1,2 and Takehiko Yamato1 of Applied Chemistry, Faculty of Science and Engineering, Saga University 2Department of Organic Device Engineering, Yamagata University . ORGANIC LIGHT EMITTING DIODE – MATERIAL, PROCESS AND DEVICES Edited by Seung Hwan Ko Organic Light Emitting Diode – Material, Process and Devices Edited. CHCl 3 (Table 1). The ligand copolymers 2a and 2b were prepared in the presence of AIBN. 12 The reaction of these Organic Light Emitting Diode – Material, Process and Devices 8 copolymers. Two types of Organic Light Emitting Diode – Material, Process and Devices 4 phosphorescent PLED materials are known: (1) host polymers such as poly(vinylcarbazole) (PVK) and poly(9,9-di-n-octyl-2,7-fluorene)