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 [...]... Metal-containing Polymer Scheme 1 Synthetic methodology of metal-containing polymer 6 Organic Light Emitting Diode – Material, Process and Devices N x y O + O O Ir O N N + O y z ethylene glycol N O x Ir(ppy)2 17 0oC, 17 h N N Scheme 2 C6H13 C6H13 C6H13 C6H13 O + N O O O Ir N m-cresol reflux, 12 h O O x+y C6H13 C6H13 N x y Ir O O 2 C6H13 C6H13 C6H13 C6H13 + N N m-cresol N x y Ir reflux, 12 h N 2 Scheme 3 O x... = 2 C8H17 5 : M = Pt, n = 1 N M 0 .1 x N Cl C8H17 n 12 : M = Ir, n = 2 13 : M = Pt, n = 1 Scheme 9 Preparation of the conjugated metallopolymers 10 -13 Ligand Polymer Comonomer FlBO (mmol) FlBr (mmol) PABr (mmol) PyBO (mmol) Yield (%) Pyridine Content (mol%) Mn ( 10 4 g/mol) PDI 8aa 5 .1 6.2 0.0 1. 8 34 2.9 2.9 1. 4 8b 5.2 6.2 0.0 1. 8 53 2.0 3.4 1. 6 9aa 5.2 5.0 1. 2 1. 8 28 3.5 3 .1 1.3 9b 5.4 5.0 1. 2 1. 8 52... spectra 12 Organic Light Emitting Diode – Material, Process and Devices for the analogous polymers 11 and 13 containing platinum unit also showed the successful formation of the metallopolymers, in which the platinum unit has the similar structure to 15 8 CH2Cl2 [MCl(piq)n]2 + N reflux, overnight N M x 3 : M = Ir, n = 2 C8H17 5 : M = Pt, n = 1 N Cl C8H17 n 10 : M = Ir, n = 2 11 : M = Pt, n = 1 9 + CH2Cl2... 500 600 700 Wavelength (nm) 800 0 500 600 700 Wavelength (nm) 800 Fig 10 PL spectra for (a) 10 , 11 , (b) 12 and 13 in CH2Cl2 Iridium polymers 10 and 12 and platinum polymers 11 and 13 were irradiated at 462 and 433 nm, respectively (at 0.5 g/L) 5 EL behavior of the metallopolymers EL behavior of devices containing the metallopolymers and the monomeric metal complexes was investigated The metallopolymers... triarylamine-containing ligand copolymers 9a and 9b The yields, averaged moleculer weights, and pyridyl-group contents are listed in Table 3 The reactions of the ligand polymers 8a and 9a with the iridium precursor 3 efficiently formed the metallopolymers 10 and 12 The theoretical ratios of the iridium unit, [IrCl(piq)2(py)] in 10 and 12 were 1. 7 and 1. 7 wt% The platinum analogs 11 , 13 were similarly synthesized... Fig 9 PL spectra for (a) 5, 6 and (b) 7 Iridium polymers 5 and 7 and platinum polymer 6 were irradiated at 462 and 433 nm, respectively (metallopolymers 5, 6 were 0.05 g/L and metallopolymers 7 were 0.5 g/L) Synthesis, and Photo- and Electro-Luminescent Properties of Phosphorescent Iridium- and Platinum-Containing Polymers 15 0 15 400 (a) 10 11 10 0 (b) 12 13 300 200 50 10 0 0 500 600 700 Wavelength (nm)... 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 the aromatic region Synthesis, and Photo- and Electro-Luminescent Properties of Phosphorescent Iridium- and Platinum-Containing Polymers 11 series of conjugated ligand... 8b, 9b and the platinum precursor 5 The yields and the content ratios of iridium and platinum are listed in Table 4 O O B B O 2) + Br Br + Br Br + N N BR O C8H17 C8H17 C8H17 C8H17 OH O or B BR = B O Pd(OAc)2 N N y P(o-MeOC6H4)3 Aliquat 336 Toluene / Na2CO3 aq 1) 10 5℃, 3 h 2) 10 5℃, 21 h OH C8H17 N z x C8H17 8 : y / z = 1. 0 / 0.0 9 : y / z = 0.9 / 0 .1 Scheme 8 Preparation of the conjugated ligand polymers... Figure 10 The spectra indicated that each structure of the metal unit was 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, ... the carbazole side chain Ligand Polymer Comonomer Vp Other (mmol) (mmol) Initiator (mmol) Yield (%) Vp Content (mol%) Mn ( 10 4 g/mol) PDI 1 0.93 MMA 9.3 BPO 0.050 10 0 23 96 2.7 2a 1. 0 Vc 20 AIBN 0 .10 82 4.7 5.0 2 .1 2b 2.0 Vc 20 AIBN 0 .10 20 15 3.8 3.5 Table 1 Preparation of Ligand Polymers Polymer Complex 5 6 7a 7b Feed Polymer Ligand (Pyridine Content / mmol) 1 0.40 1 0.0 41 2a 0.20 2b 0.20 Feed Precursor . ORGANIC LIGHT EMITTING DIODE – MATERIAL, PROCESS AND DEVICES Edited by Seung Hwan Ko Organic Light Emitting Diode – Material, Process and Devices Edited. 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. Organic Light Emitting Diode – Material, Process and Devices 6 N N N Ir(ppy) 2 xyz ethylene glycol 17 0 o C, 17 h N N xy ++ N Ir O O OO O O Scheme 2. N N C 6 H 13 C 6 H 13 C 6 H 13 C 6 H 13 Ir N 2 x