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MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS VOLUME 665 Electronic, Optical and Optoelectronic Polymers and Oligomers Symposium held April 17-20, 2001, San Francisco, California, U.S.A. EDITORS: Ghassan E. Jabbour The University of Arizona Tucson, Arizona, U.S.A. Niyazi Serdar Sariciftci Johannes Kepler University of Linz Linz, Austria Materials Research Society Warrendale, Pennsylvania

Electronic, Optical and Optoelectronic Polymers and Oligomers

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Page 1: Electronic, Optical and Optoelectronic Polymers and Oligomers

MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS VOLUME 665

Electronic, Optical and Optoelectronic Polymers and

Oligomers

Symposium held April 17-20, 2001, San Francisco, California, U.S.A.

EDITORS:

Ghassan E. Jabbour The University of Arizona Tucson, Arizona, U.S.A.

Niyazi Serdar Sariciftci Johannes Kepler University of Linz

Linz, Austria

Materials Research Society Warrendale, Pennsylvania

Page 2: Electronic, Optical and Optoelectronic Polymers and Oligomers

CONTENTS

Preface xiii

Materials Research Society Symposium Proceedings xiv

ELECTRONIC AND OPTICAL PROPERTIES!

* Mechanism of Carrier Photoexcitation in Semiconducting Polymers: The Role of Electron Photoemission in "Photoconductivity" Measurements 3

Daniel Moses, Paulo B. Miranda, Cesare Soci, and Alan J. Heeger

* Photoinduced Enhancement of Photoluminescence Intensity in PPV Films 17

Yara Galväo Gobato, Alexandre Marietta, Jucimar M. Souza, Ernesto Pereira, Roberto M. Faria, and Francisco E.G. Guimaraes

Third Order Non-Linear Optical Properties of Polyphenylene Vinylene Derivatives in the Infrared Range 23

Yuri A. Dubitsky, Antonio Zaopo, Andrea Zappettini, Giulia Facchini, Franco D Amore, Silvia Pietralunga, and Mario Martinelli

Tunable Optical Gain from Soluble Thiophene-Based Oligomers 29

M. Anni, G. Gigli, M. Zavelani-Rossi, С Gadermaier, G. Lanzani, G. Barbarella, L. Favaretto, and R. Cingolani

* Optical Probing of Polarons and Triplet Excitons in Conjugated Polymer Devices 35

Anoop S. Dhoot and Neil С Greenham

MATERIALS

* The First Example of a Polythiophene Bearing Fused Tetrathiafulvalene Units 45

Peter J. Skabara, Donna M. Roberts, Asim K. Ray, Suresh S. Umare, Aseel K. Hassan, Alexey V. Nabok, and Klaus Müllen

*Invited Paper

Page 3: Electronic, Optical and Optoelectronic Polymers and Oligomers

ELECTRONIC AND OPTICAL PROPERTIES II

Admittance Spectroscopy on Polymer Light-Emitting Diodes 55 P.W.M. Blom, H.C.F. Martens, H.B. Brom, and J.N. Huiberts

* Metal-to-Ligand Charge Transfer Excited States in 7t-Conjugated Systems 61

Yiting Li, С Ed Whittle, Keith A. Walters, Kevin D. Ley, and Kirk S. Schanze

DEVICES 1

Polarized Electroluminescence in Double Layer LEDs With Perpendicularly Oriented Polymers 75

A. Bolognesi, С Botta, D. Facchinetti, M. Jandke, P. Strohriegl, K. Kreger, and S. Blumstengel

* Approaches to Advanced Organic Light Emitting Diodes: Materials and Devices 81

Masamichi Ikai and Yasunori Taga

Statistical Method to Optimize the Efficiency of Multi-Layer Polymer LEDs 93

Michele Cecchi, David Braun, Heather Smith, and Linda Vanasupa

POSTER SESSION

A Mercury Selective Electrode 101 Jon Scaggs, Dale D. Russell, S.P. Duttagupta, and Michael W. Hill

Microcavity Effects in Thiophene-Based Oligomers 109 G. Gigli, M. Anni, S. Patane, G. Barbarella, L. Favaretto, and R. Cingolani

Structural Properties of Conjugated Molecular Crystals Under High Pressure „...115

Georg Heimel, Egbert Zojer, Roland Resel, Peter Puschnig, Kerstin Weinmeier, and Claudia Ambrosch-Draxl

*Invited Paper

vi

Page 4: Electronic, Optical and Optoelectronic Polymers and Oligomers

Energy Level Alignment and Exciton Binding Energies Using Model Interfaces Between Metals and Evaporable Organic Electroluminescent Materials 121

Santos F. Alvarado and Walter Rieß

Synthesis and Characterization of Poly(jY-alkyl-2,7-carbazole)s: Blue Light-Emitting Materials 127

J.-F. Morin, M. Leclerc, I. Levesque, and M. D'lorio

Stabilization of Optical Molecules Using Dendritic Boxes Against Singlet Oxygen in Photobleaching 133

Sonoko Otomo, Akira Otomo, and Shinro Mashiko

The Relationship Between Molecular Structure and Spectroscopic Properties of a Series of Transition Metal-Containing Phenylacetylene Oligomers and Polymers 139

Thomas M. Cooper, Daniel G. McLean, and Joy E. Rogers

Self-Assembled Growth of Highly Oriented Para-Sexiphenyl Thin Films Controlled by Elastic Strain 145

Andrei Yu. Andreev, Helmut Sitter, Christoph J. Brabec, Peter Hinterdorfer, Günter Springholz, Niyazi S. Sariciftci, Roland Resel, and Harald Plank

Synthesis of 3,4-Disubstituted Poly(thiophene)s via Substitution of Poly(3-alkylthiophene) 151

Yuning Li, George Vamvounis, and Steven Holdcroft

Novel Guest-Host NLO Polyimide Based on Two-Dimensional Carbazole Chromophores 157

Wen-Jang Kuo, Ging-Ho Hsiue, and Ru-Jong Jeng

Investigation of Morphology and Interface in Polymer Composite Thin Films 163

CK. Chiang, L.P. Sung, and R. Popielarz

Synthesis and Characterization of Polypyridine Derivatives: Towards Regioregular PPY 169

Lockhart E. Horsburgh, Andrew P. Monkman, Changsheng Wang, and Martin R. Bryce

The Synthesis, Condensation, and Luminescence of Stilbenoid Oligomers With Alkoxysilane End Groups 175

H. Detert and E. Sugiono

vi i

Page 5: Electronic, Optical and Optoelectronic Polymers and Oligomers

Charge Transport in Pentacene Thin Film Transistors 181 J.H. Schön, L.D. Buchholz, Ch. Kloc, and B. Batlogg

Design, Synthesis and Charaterization of Polymers Derived from Fluorene for Application in RGB Polymer Light-Emitting Diodes 187

Serge Beaupre, Mario Leclerc, Isabelle Levesque, and Marie D'Iorio

Deposition and Characterization of Metal/Polyaniline Bi-Layers 193

Y. Liu, M.J. O'Keefe, A. Beyaz, С Singleton, and T.P. Schuman

Lateral and Vertical Phase Separation Control of Thin-Film Structures for Photovoltaics 199

A.C. Arias, J.D. MacKenzie, N. Corcoran, and R.H. Friend

Photoconductivity of Pentacene Thin-Film Transistors 207 D. Knipp, D.K. Murti, B. Kxusor, R. Apte, L. Jiang, J.P. Lu, B.S. Ong, and R.A. Street

A Comparative Study of the Photophysics in Polyfluorenes and Polyfluorenes With Polyphenylene Dendron Sidechains 213

E.J.W. List, A. Pogantsch, F.P. Wenzl, C.-H. Kim, J. Shinar, M.A. Loi, G. Bongiovanni, A. Mura, S. Setayesh, A.C. Grimsdale, H.G. Nothofer, K. Müllen, U. Scherf, and G. Leising

Effects of Inserting Highly Polar Salts Between the Cathode and Active Layer of Bulk Heterojunction Photovoltaic Devices 219

Sean E. Shaheen, Christoph J. Brabec, N. Serdar Sariciftci, and Ghassan E. Jabbour

DEVICES II

Silole Derivatives With a High and Non-Dispersive Electron Mobility, and a 100% Photoluminescence Quantum Efficiency 227

H. Murata, G.G. Malliaras, M. Uchida, Y. Shen, and Z.H. Kafafi

V l l l

Page 6: Electronic, Optical and Optoelectronic Polymers and Oligomers

PHOTO VOL TAICS AND TRANSISTORS

* Electronic Properties of Polymer-Fullerene Solar Cells 235 V. Dyakonov, I. Riedel, С. Deibel, J. Parisi, C.J. Brabec, N.S. Sariciftci, and J.C. Hummelen

* Ultrafast Energy and Electron Transfer in Conjugated Oligomer-Fullerene Molecules 247

P.A. van Hal, R.A.J. Janssen, G. Lanzani, G. Cerullo, M. Zavelani-Rossi, and S. De Silvestri

Analysis of Polymer Field Effect Transistor 259 Y. Roichman and N. Tessler

High Performance Organic Field-Effect Transistors and Integrated Inverters 265

A. Ullmann, J. Ficker, W. Fix, H. Rost, W. Clemens, I. McCulloch, and M. Giles

* Thiophene Oligomer and NTCDI Semiconductors With High Field-Effect Transistor On/Off Ratios 271

Howard E. Katz, Andrew J. Lovinger, X. Michael Hong, Jerainne Johnson, Bo-Cheng Wang, and Krishnan Raghavachari

Image Sensor Arrays With Organic Photoconductors 281 R.A. Street, J. Graham, Z. Popovic, A. Hor, M. Mulato, R. Lau, and J. Ho

POSTER SESSION

Electron Accepting Oligomers and Polymers: Chain Scission Under Quaternization Conditions 289

Douglas S. Dudis and B. Robert McKellar

Conjugatged Oligomeric Coordinated Silver Phenylacetylide Derivatives With Ultrafast Optical Kerr Effect 295

Y.H. Xu, B.K. Teo, H.M. Wu, S.L. Guo, Y.K. He, H.Y. Chen, W. Qian, S.J. Wu, and Y.H. Zuo

ESR Investigations on Polyaniline-Polyvinylchloride Blends 301 M. Chipara, E. Goovaerts, Magdalena Chipara, and I. Munteanu

* Invited Paper

IX

Page 7: Electronic, Optical and Optoelectronic Polymers and Oligomers

Luminescent Polymer Fibers for Light Amplification and Lasing 307

Takeyuki Kobayashi, Werner J. Blau, Hartwig Tillmann, and Hans-Heinrich Hörhold

A Unified Model for the Space Charge Limited Currents in Organic Materials Combining Field Dependent Mobility and Poole-Frenkel Detrapping 313

S.C. Jain, W. Geens, V. Kumar, A. Kapoor, A. Mehra, T. Aernouts, J. Poortmans, R. Mertens, and M. Willander

Inorganic-Organic Hybrid Materials (ORMOCER®s) for Multilayer Technology—Passivation and Dielectric Behavior 321

R. Houbertz, L. Fröhlich, J. Schulz, and M. Popall

Steady State Photoconductivity in Conjugated Polymers 327 CD. Sitch, D.P. Halliday, and A.P. Monkman

High-Pressure Studies of Polyaromatic Molecular Crystals: Optical and Electronic Properties From First Principles 333

Kerstin Weinmeier, Peter Puschnig, Claudia Ambrosch-Draxl, Georg Heimel, Egbert Zojer, and Roland Resel

Preparation of Diarylethene Substituted Polymer Films for Optical Recording 339

Song Yun Cho and Eunkyoung Kim

The Influence of Nanostructure Formation on Properties for Cr Implanted PET 347

Wu Yuguang, Zhang Tonghe, Zhang Huixing, Zhang Xiaoji, Cui Ping, and Zhou Gu

Synthesis and Characterization of Low Content of Structural Defects of Aryl-Substituted Electroluminescent Poly(/>-phenylenevinylene)s 353

Zhi-Kuan Chen, Nancy Hoi Sim Lee, and Wei Huang

Synthesis and Optical Properties of a Novel Oligobipyridine 359 Y.J. Fu, T.K.S. Wong, H.X. Zhang, GM. Wang, X. Hu, Z.S. Gao, and M.H. Jiang

Materials Characterization and Synthesis of Conductive Aromatic-bis(benzothiazoles) 365

Max D. Alexander Jr., Balasubramanian Sankaran, B. Robert McKellar, and Douglas S. Dudis

x

Page 8: Electronic, Optical and Optoelectronic Polymers and Oligomers

Molecular Assemblies, Patterning, and Deposition of Conjugated Polymers: Ultrathin Films Prepared Using the Layer-by-Layer and Precursor Polymer Electrodeposition Approach 371

Rigoberto Advincula, Mi-kyoung Park, and Chuanjun Xia

Electric Field Induced Self Assembly and Template Patterning of Polymer Microstructures 377

Cengiz S. Ozkan and Huajian Gao

SELF-ASSEMBLY, NANOSTRUCTURES AND PRINTING

* Ionic Self Assembly and Low Conversion Temperature (P-phenylene vinylene) 385

A. Marietta, F.A. Castro, C.A.M. Borges, R.M. Faria, and F.E.G. Guimaraes

Solvent-Enhanced Dye Diffusion in Polymer Thin Films for OLED Application 391

F. Pschenitzka, K. Long, and J.C. Sturm

GRO WTH AND INTERFA CES

The Effect of Surface Preparation on the Structure and Electrical Transport in an Organic Semiconductor 401

Laura L. Kosbar, Christos D. Dimitrakopoulos, and Debra J. Mascaro

Effect of Interface and Crystallinity on the Ferroelectric Properties of Poly(vinylidene fluoride-trifluoroethylene) Copolymer Thin Films 407

Feng Xia, H.S. Xu, Babak Razavi, and Q.M. Zhang

Author Index -...413

Subject Index _....417

*Invited Paper

XI