electrical, optical, and magnetic properties of organic...

Electrical, Optical, andMagnetic Properties of

Organic Solid-State Materials IV

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Cambridge University Press978-1-107-41345-0 - Materials Research Society Symposium Proceedings: Volume 488:Electrical, Optical, and Magnetic Properties of Organic Solid-State Materials IVEditors: John R. Reynolds, Alex K-Y. Jen, Michael F. Rubner, Long Y. Chiang and Larry R. DaltonFrontmatterMore information

http://www.cambridge.org/9781107413450

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MATERIALS RESEARCH SOCIETYSYMPOSIUM PROCEEDINGS VOLUME 4 8 8

Electrical, Optical, andMagnetic Properties of

Organic Solid-State Materials IVSymposium held December 1-5,1997, Boston, Massachusetts, U.S.A.

EDITORS:

John R. ReynoldsUniversity of Florida

Gainesville, Florida, U.S.A.

Alex K-Y. JenNortheastern University

Boston, Massachusetts, U.S.A.

Michael F. RubnerMassachusetts Institute of Technology

Cambridge, Massachusetts, U.S.A.

Long Y. ChiangNational Taiwan University

Taipei, Taiwan.

Larry R. DaltonUniversity of Southern California

Los Angeles, California, U.S.A.

IMTRIS1Materials Research Society

Warrendale, Pennsylvania






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CONTENTS

Preface xix

Acknowledgments xxi

Materials Research Society Symposium Proceedings xxii

PARTI: ORGANIC LIGHT-EMITTING MATERIALS AND DEVICES

'Optically and Electrically Excited Semiconducting PolymerStructures 3

H. Becker, S.E. Burns, G.J. Denton, N.T. Harrison, N. Tessler,T.D. Wilkinson, and R.ti. Friend

Transient Electroluminescence From PPV Under StrongVoltage Pulses 15

V. Savvate'ev, R. Pogreb, D. Davidov, H. Chayet, R. Neumann,and Y. Avny

Light-Emitting and Hole-Transporting Polymers for LEDs 21Toshihiro Ohnishi, Shuji Doi, Masato Veda, Fumi Yamaguchi,and Takanobu rioguchi

White Light-Emitting Electroluminescence Devices withOrganic Oligomers 27

F. Meghdadi, S. Tasch, W. Qraupner, S.E. Dottinger, M. Hanack,M. Qraupner, A. Hermetter, and G. Leising

Plastic Multilayered Molecular Organic Light-EmittingDiodes 33

George M. Daly, tlideyuki Murata, Charles D. Merritt, Zakyati. Kafafi, Hiroshi Inada, and Yasuhiko Shirota

'Advanced Photorefractive and Light-Emitting OrganicMaterials 39

N. Peyghambarian and B. Kippelen

Synthesis and Electroluminescence Study of a NovelCopolymer: Poly(Phenylene Vinylene-Co-QuinolineVinylene) 51

Ramesh K. Kasim, Bela Derecskei, Martin Pomerantz,and Ronald L. Elsenbaumer

LECs Made of m-LPPP 57F.P. Wenzl, S. Tasch, J. Gao, L. tiolzer, U. Scherf, A.J. tieeger,and G. Leising

*lnvited Paper






Electrochemically-Based Light-Emitting Devices FromSequentially Adsorbed Multilayers of a PolymericRuthenium (II) Complex and Poly(Acrylic Acid) 63

Aiping Wu, Jin-kyu Lee, and Michael F. Rubner

Improved Electron Injection in Organic Light-EmittingDevices by Applying Thin Insulating Layers 69

R. Pairleitner, S. Tasch, G. Leising, and U. Scherf

'Control of Light-Emitting Polymer Devices UsingPolymer/Polymer Interfaces 75

A.J. Epstein, Y.Z. Wang, D.D. Gebler, D.K. Fit, and T.M. Swager

New Luminescent PPV Derivatives for LED Applications 87B.S. Chuah, F. Cacialli, J.E. Davies, N. Feeder, R.ti. Friend,A.B. Holmes, E.A. Marseglia, S.C. Moratti, J-L. Bredas,and D.A. dos Santos

AC Light-Emitting Diodes and Their Transient Characteristics:Response Time and Carrier Transport 93

A.J. Pal, T. Ostergard, R. Osterbacka, K-M. Kallman, and ti. Stubb

Dynamics of Polarons in Guest-Host-System Polymer Light-Emitting Devices 99

E.J. W. List, J. Partee, W. Graupner, J. Shinar, and G. Leising

'Polymeric Zinc-Bisquinoline-Based Self-Assembled Light-Emitting Diodes 105

F. Papadimitrakopoulos, D.L. Thomsen, HI, and K.A. Higginson

Polymer Layer Ordering of Polyaniline Derivatives in PLEDDevices: Surface Adsorption and Characterization 115

R.C. Advincula, W. Knoll, C.W. Frank, D. Roitman, R. Moon,andJ. Sheats

Internal Field Distribution in Organic Light-Emitting DiodesWith Double Layer Structure 121

C. Hochfilzer, T. Jost, A. Mko, W. Graupner, G. Leising, C.W. Tang,E. Forsythe, and Y. Gao

Photoexcitations of Oligothiophenes With ReducedConformational Mobility 127

L. Rossi, G. Bongiovanni, C. Botta, G. Cerullo, G. Lanzani, A. Mura,F. Sannicolo, T. Benincori, and R. Tubino

Self-Assembled Multilayers and PhotoluminescenceProperties of a New Water-Soluble Poly(Paraphenylene) 133

Xiaobo Shi, DeQuan Li, M. Lutt, M.R. Fitzsimmons,and G.P. Van Patten

*lnvited Paper

vi






PART II: PHOTONIC MATERIALS AND DEVICES

*Photofabrication of Surface Relief Gratings Using PostFunctionalized Azo Polymers 141

Sukant K. Tripathy, Jayant Kumar, Dong-Yu Kim, Xinli Jiang,Xiaogong Wang, Lian Li, Mongkol Sukwattanasinitt,and Daniel J. Sandman

High E-O Coefficient Polymers Based on a ChromophoreContaining Isophorone Moiety for Second-Order NonlinearOptics 151

Jinghong Chen, Jingsong Zhu, Qalina Todorova, Mingqian fie,Larry R. Dalton, Sean M. Garner, Antao Chen, Sang-Shin Lee,Vadim Chuyanov, and William H. Steier

* Passive Polarization Rotators for Nonlinear Optical Devices 157T.C. Kowalczyk, L-Y. Liu, and H.S. Lackritz

Molecular Second-Order Optical Nonlinearity of Push-PullBisdithiolene Nickel Complexes 165

Chin-Ti Chen, Sish-Yuan Liao, Kuan-Jiuh Lin, and Long-Li Lai

Exciton Bandwidth and Coupling to IntramolecularPhonons in PTCDA 171

M.ti. tiennessy, Z.G. Soos, V. Bulovic, and S.R. Forrest

* Advantages of Modal Dispersion Phase-Matching andMaterials Requirements for Polymeric Devices UsingEfficient Second-Harmonic Generation atTelecommunication Wavelength 179

Matthias L. Jager, Vincent Ricci, Wook-Rae Cho,Michael T.G. Canva, and George I. Stegeman

Recent Progress of Electro-optic Polymers for DeviceApplications 193

Alex K-Y. Jen, Qing Yang, Seth R. Marder, Larry R. Dalton,and Ching-Fong Shu

"Characterizing and Circumventing IntermolecularElectrostatic Interactions in Highly Electro-optic Polymers 199

Aaron W. Harper, Jingsong Zhu, Mingqian tie, Larry R. Dalton,Sean M. Garner, and William ti. Steier

Electronic Properties of a Novel Class of ConjugatedSystems: Transition-Metal-Substituted Oligothiophenes 211

L. Lancellotti, R. Tubino, S. Luzzati, E. Licandro, S. Maiorana,and A. Papagni

*New Photopolymers Based on Two-Photon AbsorbingChromophores and Application to Three-DimensionalMicrofabrication and Optical Storage 217

B.H. Cumpston, J.E. Ehrlich, L.L. Erskine, A.A. tieikal, Z-Y. tiu,l-Y.S. Lee, M.D. Levin, S.R. Marder, D.J. McCord, J.W. Ferry,H. Rockel, M. Rumi, and X-L. Wu

*lnvited Paper

vii






'Conjugated Polymer-Based Nanocomposites for PhotonicsApplications 227

P.Ti. Prasad, Pi. Deepak Kumar, Manjari Lai, and Mukesh P. Joshi

Optical Limiting Processes in Derivatized Fullerenes andPorphyrins/Phthalocyanines 237

R. Kohiman, V. Klimov, X. Shi, M. Grigorova, B.R. Mattes,D. McBranch, H. Wang, F. Wudl, J-L. Piogues, and W. Moreshead

"Synthesis and Nonlinearity of Triene ChromophoresContaining the Cyclohexene Ring Structure 243

Susan Ermer, Steven M. Lovejoy, Doris S. Leung, Hope Warren,Christopher R. Moylan, and Robert J. Twieg

Multifunctional Hyperstructured Molecules 255T. Wada, Y. Zhang, T. Aoyama, Y. Kubo, and H. Sasabe

Synthesis of a New Class of PolyphenylatedPhthalocyanines and Metallophthalocyanines 265

Christopher J. Walsh and Braja K. Mandal

Study on the Relations of Structure and the UltrafastOptical Kerr Effect of Polynitriles 271

Q. Wang, Y.Y. Li, W.W. Pel Y.K. He, C.Q. Luo, H.Y. Chen, L. Lin,C.F. Wang, and Y.H. Zou

Radiative Decay of Excitons in Model Aggregates ofit-Conjugated Oligomers 277

Eric S. Manas and Frank C. Spano

Synthesis of New Multifunctional Polymers IncorporatingBis-(Diphenylamino)Diphenylpolyene Moieties 283

C.W. Spangler, T. Faircloth, E.H. Elandaloussi, and B. Reeves

PART III: CONDUCTING AND ELECTROACTIVE POLYMERS AND MATERIALS

'Electronic Structure and Optical Response ofElectroluminescent Conjugated Polymers 293

J-L. Bredas, J. Cornil, D. Beljonne, D.A. dos Santos, Z. Shualand R. Silbey

*An Emulsion Polymerization Process for Soluble andElectrically Conductive Polyaniline 305

P.J. Kinien, Y. Ding, C.R. Graham, J. Liu, and E.E. Remsen

Modulation of the Electronic Properties inPolydithienothiophene Materials 317

C. Arbizzani, M. Cateliani, S. Luzzati, and M. Mastragostino

*lnvited Paper

viii






Design and Synthesis of New Conjugated PorphyrinCopolymers for Optical-Electronic Applications 323

Biwang Jiang, Szu-Wei Yang, Phuong T. Lam,and Wayne E. Jones, Jr.

Structural Approach to Improve the ResponseCharacteristics of Copper Phthalocyanine Thin-Film-BasedNO2 Gas Sensor 329

Tadashi Nagasawa, Kenji Murakami, and Kenzo Watanabe

Electrical Rectification by a Molecule ofHexadecylquinolinium Tricyanoquinodimethanide 335

KM. Metzger, B. Chen, D. Vuillaume, U. ftopfner, J.W. Baldwin,T. Kawai, ft. Tachibana, ft. Sakurai, M. V. Lakshmikantham,and M.P. Cava

Solvato-Controlled Doping of Conducting Polymers:Enhanced Stability in Silver-Triflate-Doped Films 341

Michael V. Lauritzen and Steven ftoldcroft

'Synthesis of Conjugated Polymers by Vapor-DepositionPolymerization 347

Chain-Shu ftsu and Ting-Li Lin

Double-Strand Polyaniline as a Molecular Quasi-Memoryto Chemical Stimuli 359

Gowri P. Kota, Linfeng Sun, ftuaibing Liu, and Sze C. Yang

Effect of Morphology on the Electrical Transport Propertiesof Polyaniline Films for Electronic Applications 365

S.S. ftardaker, K. Eaiprasertsak, J. Yon, R.V. Gregory,and G.X. Tessema

Melt Processed Electrically Conductive Binary and TernaryImmiscible Polymer/Polyaniline Blends 371

M. Zilberman, A. Siegmann, and M. Narkis

Thermoreversible Gels of Polyaniline: Viscoelastic andElectrical Properties 377

O.T. Ikkala, T. Vikki, J. Ruokoiainen, P. ftiekkataipale, P. Passiniemi,T. Makela, and ft. Isotalo

PART IV: MOLECULAR AND SUPRAMOLECULAR ENGINEERING

•Molecular Self-Assembly Routes to Optically FunctionalThin Films: Electroluminescent Multilayer Structures 385

W. Li, J.E. Maiinsky, ft. Chou, W. Ma, L. Geng, T.J. Marks,G.E. Jabbour, S.E. Shaheen, B. Kippelen, N. Peyghambarian,J. Anderson, P. Lee, and N. Armstrong

*lnvited Paper






A Scanning-Force-Microscopy Study of Block CopolymersContaining a Conjugated Segment 395

Ph. LeClere, R. Lazzaroni, V. Parente, B. Francois, and J-L. Bredas

Multilayer Self-Assemblies as Electronic and OpticalMaterials 401

DeQuan Li, M. Lutt, Xiaobo Shi, and M.R. Fitzsimmons

Performances of Sexithiophene Based Thin-Film TransistorUsing Self-Assembled Monolayers 407

J. Collet O. Tharaud, C. Legrand, A. Chapoton, and D. Vuillaume

'Determination of the Internal Electric Field in theElectro-optic Active Layer of Multilayer Polymer Stacks 413

5. Qrossmann, T. Weyrauch, and W. Haase

Controlling Materials Architecture on theNanometer Scale: PPV NanocompositesVia Polymerizable Lyotropic Liquid Crystals 419

Ryan C. Smith, Hai Deng, Walter M. Fischer, and Douglas L. Gin

High Mobility and Liquid-Phase Processable OrganicSemiconductors 425

tl.E. Katz, J. Laquindanum, and AJ. Lovinger

Electrical Characterization of Thin Single Crystals ofSexithiophene 431

C. Daniel Frisbie, Eric L. Granstrom, and Michael J. Loiacono

Novel Liquid-Crystal Displays Based on Highly PolarizedPhotoluminescent Polymer Films 435

Christian Sarwa, Andrea Montali Cees Bastiaansen,Christoph Weder, and Paul Smith

Electro-optic Effects in Nanophase Polymer DispersedLiquid-Crystal Systems 441

R.S. Blacker, K.L. Lewis, I. Mason, I. Sage, and K. Webb

Structural And Electronic Properties of Self-AssembledSupramolecular Grid Structures: Doping ofSupramolecular Thin Films 447

J. fiassmann, C.Y. tiahn, O. Waldmann, E. Volz, H-J. Schleemilch,ft. Mallschmid, P. Muller, G.S. Hanan, D. Volkmer, U.S. Schubert,J-M. Lehn, ft. Mauser, A. ftirsch, and T. Clark

Photochromic Liquid Hydrogels as Hosts for HolographicMaterials 453

R.L. White, Y.Y. ftsu, T.M. Cooper, J.D. Gresser, D.L. Wise,and D.J. Trantolo

*lnvited Paper






PARTV: ORGANIC METALS AND MAGNETIC MATERIALS

"Organic/Inorganic Langmuir-Blodgett Films Based onMetal Phosphonates 461

Daniel R. Talham, Gail E. Fanucci, Melissa A. Petruska,and Candace T. Seip

AC Susceptibility Studies of New and Familiar MagneticMolecular Solids 471

Roger D. Sommer, Brenda J. Korte, Scott P. Sellers,and Gordon T. Yee

Magnetic Properties of Organic Ferromagnetic TDAE-C6oSingle Crystals and Thin Films 477

M. Tokumoto, Y. Tsubaki, K. Pokhodnya, Y. Sakakibara, A. Omerzu,D. Mihailovic, and T. Uchida

Functionalized Tetrathiafulvalene Derivatives and TheirRadical Cation Salts: Synthesis and X-ray CrystalStructures 483

Martin R. Bryce, Adrian J. Moore, Andrei S. Batsanov,Antony Chesney, Clare L. Wood, and Judith A.K. Howard

Electronic Structure of the Organic Metals K - E T 2 C U ( S C N ) 2

and K-ET2Cu|N(CN)2]Br Measured by Soft X-ray Emissionand Soft X-ray Absorption 489

Cristian B. Stagarescu, L-C. Duda, Kevin E. Smith, J.ti. Guo,J. Iiordgren, R. Haddon, J.S. Brooks, and D. Jerome

Preparation of C 6 0 Charge-Transfer Complexes WithOrganic Donor Molecules and Alkali Doping 495

A. Otsuka, G. Saito, S. fiirate, S. Pac, T. Ishida, A.A. Zakhidov,and K. Yakushi

PART VI: POSTER PRESENTATIONS

Metal Complex Polymers for ElectroluminescentApplications 503

X.T. Tao, ti. Suzuki, YD. Zhang, T. Watanabe, S. Miyata, T. Wada,and ti. Sasabe

Investigations on the Aluminum/Para-HexaphenylInterface in Light-Emitting Devices 509

ft. Koch, LrM. Yu, J-L. Guyaux, Y. Morciaux, G. Leising, J-J. Pireaux,and G. Demoustier

Characterization of Poly(Paraphenylene) Subjected toDifferent Heat Treatment Temperatures 515

S.D.M. Brown, M.J. Matthews, A. Marucci, M.A. Pimenta,M.S. Dresselhaus, M. Endo, and T. Hiraoka

*lnvited Paper

xi






'Morphological Effects in the Chemical andPhotoluminescent Behavior of AluminumTris(8-Hydroxyquinoline) (Alq3) 521

K.A. Higginson, X-M. Zhang, and F. Papadimitrakopoulos

Fabrication of Polymer Light-Emitting Diodes byLayer-by-Layer Complexation Technique 527

Jaehyun Kim, Kethinni G. Chittibabu, Mario J. Cazeca,Woohong Kim, Jayant Kumar, and Sukant K. Tripathy

Optical Properties of Distyrylbenzene Chromophores andTheir Segmented Copolymers 533

Nicholas Benfaremo, Daniel J. Sandman, Sukant Tripathy,Jayant Kumar, Ke Yang, Michael F. Rubner, and Cormac Lyons

Light-Emitting Diodes With Voltage-Switchable Colors FromSemiconducting Polymer/Polymer Heterojunctions 539

Xuejun Zhang and Samson A. Jenekhe

Toward Electrically Pumped Organic Diode Lasers:Electroluminescence of Proton Transfer Polymers 545

Xuejun Zhang, Richard M. Tarkka, Samson A. Jenekhe,and Joseph B. Schlenoff

*Electroactive and Photoactive Rod-Coil Block Copolymers:Self-Organization and Photophysical Properties 551

X. Linda Chen and Samson A. Jenekhe

Concentration Dependence of Photoluminescence andElectroluminescence in 2,5 Bis[2'-(4"-HydroxyhexanolBenzyl)-r-Ethyl]3,4-Dibutyl Thiophenes 557

5. Blumstengel, I. Sokolik, R. Dorsinville, D. Voloschenko, M. He,LrC. Chien, and O. Lavrentovich

Ionic Complexes of Conjugated Oligoquinolines 563Ashok S. Shetty and Samson A. Jenekhe

Cascade Connected Organic EL Diodes for MulticolorEmission 569

Yutaka Ohmori, Norio Tada, Yoshitaka Kurosaka, Akihiko Fujii,and Katsumi Yoshino

Control of Emissive Layer Interfaces With Inorganic ThinLayer Between 8-Hydroxyquinoline Aluminum and DiamineLayers in Organic EL Diode 575

Yutaka Ohmori, Yoshitaka Kurosaka, norio Tada, Akihiko Fujii,and Katsumi Yoshino

Synthesis and Photophysical Properties of SomeConjugated Polymers Functionalized With RutheniumPolypyridine Complexes 581

Po King rig, Wai Yue rig, Xiong Gong, and Wai Kin Chan

xii






Low-Pressure Organic Vapor-Phase Deposition of SmallMolecular Weight Organic Device Structures 587

M.A. Baldo, V.G. Kozlov, P.E. Burrows, S.R. Forrest V.S. Ban,B. Koene, and M.E. Thompson

Photolithographic Patterning of Vacuum-DepositedOrganic Light-Emitting Devices 593

P.F. Tian, P.E. Burrows, V. Bulovic, and S.R. Forrest

Moisture Effect on Polythiophene Electroluminescence 599Tsu-Chien Weng, Bin-Yaw Jin, Ding-Kuo Ding,and Mitsuhiko Sakakibara

Design of Flat-Panel Displays Based on Organic Light-Emitting Devices 605

G. Gu, P.E. Burrows, and S.R. Forrest

Effect of Impurity Ions and Permanent Dipoles for DevicePerformance of Thin-Film Electroluminescent Diodes 611

Tetsuo Tsutsui, Masayuki Yahiro, and Dechun Zou

Light-Emitting Devices With Molecularly-Doped PolymerLayers: A New Diamine as a Hole-Transporting Molecule 617

V. Fattori, M. Cocchi, P. Di Marco, G. Giro, J. Kalinowski,P. Dembech, G. Fabbri, and G. Seconi

Nanostructure of Electrically Conducting PolyanilinePrepared by a Novel Emulsion Polymerization Process 623

J. Liu, P.J. Kinien, and C.R. Graham

Injection Efficiency From Various Metals Into Trap-FreeMolecularly-Doped Polymers Evaluated From CombinedAnalysis of Current-Voltage and Time-of-Flight DriftMobility Data 629

M. Abkowitz, J.S. Facci, and J. Rehm

Electrical Properties of Au/Polymer Interfaces 635A. Ioannidis, J.S. Facci, and M. Abkowitz

Hexacyanodiazahexadiene (HCDAH) Dianion as aComponent of Conducting Complexes 641

tiideki Yamochi, Kiyohiko Tsutsumi, Takeshi Kawasaki,and Gunzi Saito

Synthesis and Incorporation of Thienylene VinyleneOligomers in Main-Chain Copolymers 647

L.G. Madrigal, E.H. Elandaloussi, and C.W. Spangler

Corrosion Protection of Metals by Conductive Polymers III:Improved Performance and Inhibition in NaCI 653

Wei-Kang Lu, Ronald L. Elsenbaumer, T. Chen, and V.G. Kulkarni

XIII






Organic Metals and Superconductors: Facile SyntheticMethodologies Bypassing Coupling and Chromatography 659

Ronald L. Meline and Ronald L. Elsenbaumer

Synthesis, Characterization, and Properties of ConjugatedPoly(l-Alkyl-2,5-Pyrrylene Vinylene) 666

In Tae Kim and Ronald L. Elsenbaumer

Conjugated Polymers Containing Pendant TerpyridineComplexes as Photoactive Sensors 671

Biwang Jiang, Shailesh Sahay, and Wayne E. Jones, Jr.

Self-Assembling Functionalizable Polydiacetylenes andTheir Optical Properties 677

M. Sukwattanasinitt, X. Wang, D-C. Lee, L. Li, J. Kumar,S.K. Tripathy, and D.J. Sandman

New Polydiacetylenes With Visible Chromophoric SideGroups 683

James L. Foley, Venkataramani Shivshankar,and Daniel J. Sandman

Investigation of Organic-Organic Interfaces byTime-Resolved Photocurrent, Electrochemical, andPhotoemission Techniques 689

Liang-Bin Lin, M. Gary Mason, Ralph H. Young, Deniz E. SchildkrautPaul M. Borsenberger, and Samson A. Jenekhe

Observation of the Temperature Dependence of theDynamics of Photoexcited States in PristineTris(8-Hydroxyquinoline) Aluminum (Alq3) 695

Richard Priestley, Ardie D. Walser, and Roger Dorsinville

Temperature Dependence of the Electrical Conductivityof Poly(Benzo[1,2-b:4,5-b'] Dithiophene-4,8-Diyl Vinylene)and Poly(Dodecylthiophene) 701

R.C. flyer, R.G. Pethe, T. Yogi, S.C. Sharma, Martin Pomerantz,J. Wang, R.L. Meline, R.L. Elsenbaumer, and R.C. McCullough

Electron Transfer at the n-lnP | Poly(Pyrrole) Interface 707Mark C. Lonergan, Christopher T. Cooney, and James A. Myers

The Dielectric Response of a 8-Hydroxyquinoline AluminumUsed in Multilayer Organic Devices 713

A. Miko, C. Hochfilzer, T. Jost, W. Graupner, and G. Leising

UV Photoemission Study of Interfaces Related to OrganicEL Devices 719

Kiyoshi Sugiyama, Kazuhiko Seki, Eisuke Ito, Yukio Ouchi,and Hisao Ishii

XIV






Poly(2-Butyne-1,4-Diyl)s as Precursors to Novel SubstitutedPolyacetylenes 725

Steven K. Pollack and Ashebir Fiseha

Polymeric Complexes of Polyaniline as AnticorrosionCoatings 733

R.J. Racicot, S.C. Yang, and R. Brown

Nanocomposites of Metallophthalocyanines andConjugated Polymers 741

Shujian Yi and Samson A. Jenekhe

Latex like Water-Borne Polyaniline for CoatingApplications 747

Huaibing Liu, Robert Clark, and Sze C. Yang

Thermally Stimulated Luminescence of Naphthyl-Substituted Benzidine Derivative and Tris-8-(Hydroxyquinoline)Aluminum With and Without Metal Layers 753

E.W. Forsythe, D.C. Morton, and Y. Qao

Structural Properties of Self-AssembledPoly(Zinc-Bisquinoline) 759

D.L. Thomsen, III, T. Phely-Bobin, and F. Papadimitrakopoulos

Preparation of Chromophoric Dipolar Dendrons asSecond-Order Nonlinear Optical Material 765

S. Yokoyama and S. Mashiko

Modification of Spontaneous Emission From Periodic Arrayof Spherical Polystyrene Particles Containing FluorescentMolecules 771

T. Yamasaki and T. Tsutsui

Femtosecond Optical Nonlinearity in the Squarylium DyeJ-Aggregates 777

M. Furuki, LS. Pu, F. Sasaki, S. Kobayashi, and T. Tani

Femtosecond Pump and Probe Spectroscopy onPoly(Para-Phenylenes) 783

W. Qraupner, G. Cerullo, G. Kranzelbinder, G. Lanzani, S. Stagira,M. nisoli, S. De Silvestri, and G. Leising

Magnetic Field Effect in Highly Pure, Highly FluorescentConjugated Polymers 789

W. Graupner, M. Sacher, M. Graupner, C. Zenz, G. Grampp,A. tiermetter, and G. Leising

Design, Methodology, and Preparation of Novel Polymersfor Nonlinear Optics 795

K.G. Chittibabu, L. Li, S. Balasubramanian, X. Wang,M. Sukwattanasinitt, K. Yang, J. Kumar, D.J. Sandman,and S.K. Tripathy

XV






Characterizing the NLO Chromophore Orientation ofPolymeric Fiim by Electroabsorption Spectroscopy 801

Ke Yang, Xiaogong Wang, Woohong Kim, Aloke Jain, Lian Li,Jayant Kumar, and Sukant Tripathy

Second-Order Nonlinear Optical Polymer by DirectedLithiation of Polyethersulfone 807

Harold E. McCarron, Christopher J. Walsh, Rajashree Sen,and Braja K. Mandal

Synthesis of High-Tg Azo Polymer and the Optimization ofIts Poling Condition for Stable EO System 813

Takashi Fukuda, tiiro Matsuda, Takao Shiraga, Masao Kato,and Hachiro Nakanishi

Very Large Second-Order Nonlinear Optical ActivityShown by Heterocycle-Based DicyanomethanideZwitterions 819

A. Abbotto, S. Bradamante, A. Facchetti, Q.A. Pagani, I. Ledoux,and J. Zyss

Magnetic Properties of a Binary Mixture of ParamagneticMetallomesogens 823

Y. Shimizu, S. Tantrawong, M. Yoshida, and T. Sugino

Control of the Luminescence Properties in PolythiopheneSolutions by Interring Rotational Disorder 829

S. Luzzati, G. Bongiovanni, M. Cateilani, M.A. Loi, A. Milani,A. Mura, and A. Piaggi

New Base-Dopable Well-Defined Poly-2,7-FluoreneDerivatives 835

M. Ranger and M. LeCIerc

Magnetic Supramolecular Grid Structures: IntramolecularCoupling of Four Separate Spins 841

O. Waldmann, J. Hassmann, R. Koch, P. Muller, G.S. tianan,D. Voikmer, U.S. Schubert, and J-M. Lehn

Physical Characterization and Electrical Transport inEnd-Group Functionalized Self-Assembled Monolayers 847

J. Collet, D. Vuillaume, M. Bonnier, O. Bouloussa, F. Rondelez,J.M. Gay, K. Kham, and C. Chevrot

Ab Initio Calculations on Porphyrins in the CondensedPhase 853

P.n. Day, Z. Wang, and R. Pachter

Deformed Helix Ferroelectric Liquid Crystals With Large TiltAngles in Optically Addressed Spatial Light Modulators forDynamical Holography Applications 859

LA. Beresnev, W. Haase, A.F. Onokhov, W. Dultz, M. V. Isaev,Fi.A. Feoktistov, M.L. Ivanova, E.A. Konshina, A.Pi. Chaika,V.A. Berenberg, and T. Weyrauch

xvi






Structural Properties of Hexaphenyl Powder Under HighPressure 867

S. Guha, W. Qraupner, R. Resel, M. Chandrasekhar,ti.R. Chandrasekhar, and G. Leising

Electronic Properties of Poly(Para-Phenylenes) Under HighPressure 873

W. Qraupner, S. Guha, S. Yang, M. Chandrasekhar,ti.R. Chandrasekhar, G. Leising, U. Scherf, and K. Mullen

Doping of Polyaniline by Corona Discharge 879Aldo E. Job, Jose A. Giacometti, and Luiz ti.C. Mattoso

Polarized Light-Induced Anisotropy in Polymer FilmsDoped With Azo Dyes in the Photostationary State Studiedby IR Spectroscopy 885

K. Tawa, K. Kamada, T. Sakaguchi, and K. Ohta

Thin Film of Conjugated Sch iff-Base as Ultrahigh DensityData-Storage Material 891

W.J. Yang, Q.C. Yang, ti.G. Lu, ti.Y. Chen, S.M. Hou, L.F. Ma,tl.X. Zhang, Z.Q. Xue, and S.J. Fang

Pressure Dependence of Photoluminescence ofOligothiophenes 897

L. Rossi, W. Graupner, R. Resel, F. Meghdadi, G. Leising,F. Sannicolo, T. Benincori, G. Lanzani, and R. Tubino

Superconductivity of K-(BEDT-TTF)2Cu[N(CN)2]Br: IsotopeEffect Revisited 903

M. Tokumoto, N. Kinoshita, Y. Tanaka, and ti. Anzai

Morphology Dependence of the Optical Properties ofDALM Related Materials 909

K.B. Wagner-Brown, K.F. Ferris, J.L. Kiel, and R.A. Albanese

Thermally Stable Iridescent Colors of a NewLow-Molecular-Weight Cholesteric Compoundin the Solid State and the Application to Full-ColorRecording 915

Nobuyuki Tamaoki, Alexander V. Farfenov, Atsushi Masaki,and tiiro Matsuda

Structure and Physical Properties of EDT-TTF Salts 921Tetsuo Kondo, Lyudmila A. Kushch, tlideki Yamochi,and Gunzi Saito

A Study on Langmuir Monolayers of Methacrylate Homo-and Copolymers Derivatized With Disperse Red Dyes 927

Anantharaman Dhanabalan, Debora Balogh,Carlos Jose Leopoldo Constantino, Antonio Riul, Jr.,Osvaldo N. Oliveira, Jr., and Jose A. Giacometti

xvii






Optical Characterization of C60 Organic Semiconductorand Bilayers 933

J.P. Rainho, L. Santos, and A. A. Kharlamov

IR Studies on p6o Polymers 937K. Kamaras, L Forro, and Y. Iwasa

Author Index 943

Subject Index 949

xviii






PREFACE

The presentations of this symposium again attest to the fact that researchinvolving electrical, optical, and magnetic properties of organic solid-statematerials continues to grow both in scope and technological importance.Early studies of charge transport in conducting polymers have evolved fromthe elucidation of fundamental structure/function relationships toapplications as batteries, simple electrical devices such as diodes, chemicalsensors, antistatic coatings, microwave and millimeter wave-absorbingmaterials, and photochromic devices. A particularly exciting evolution hasbeen the discovery and development of organic light-emitting diodes (OLEDs)which appear to be nearing commercialization in an amazingly short periodof time. This application is of particular interest because both electrical andoptical properties must be considered, and these have been importantparallel themes of the conference. Moreover, nanostructure control isimportant for OLEDs, and nanoscale architectural engineering has been anincreasingly important theme of the conference. Indeed, not only has thestudy of conjugated (quasidelocalized) electrons in organic solid-statematerials resulted in interesting physical properties and device applications,but the desire to exploit these properties has promoted the development ofnew synthesis and processing methodologies to achieve special nanoscaleand microscale structures.

John R. ReynoldsAlex K-Y. JenMichael F. RubnerLong Y. ChiangLarry R. Dalton

January 1998

xix






ACKNOWLEDGMENTS

The symposium chairs would like to acknowledge the contributing andinvited authors for the outstanding quality of their presentations andproceedings manuscripts. The invited speakers included:

Jean-Luc Bredas Alan MacDiarmidMichael Canva Seth MarderArthur Epstein Tobin MarksSusan Ermer Fotios PapadimitrakopoulosSteven Forrest Joseph PerryRichard Friend Paras PrasadW. Haase Hiroyuki SasabeAaron Harper Samuel StuppAlan Heeger Timothy SwagerChain-Shu Hsu Daniel TalhamSamson Jenekhe Michael TherienPatrick Kinlen Mark ThompsonBernard Kippelen Sukant TripathyHilary Lackritz

In addition, the symposium organizers are indebted to the session chairsfor their efforts in overseeing the sessions, guiding subsequent discussions,and reviewing the manuscripts.

The symposium chairs wish to express their appreciation to the followingorganizations which provided financial support and enabled us to presentthe "Electrical, Optical, and Magnetic Properties of Organic Solid StateMaterials" symposium.

International Specialty Productsnational Taiwan University

Taiwan Four PillarsTaiwan President Enterprises

United Microelectronics Corporation

A special thanks is reserved for the Materials Research Society and staff,as well as the 1997 MRS Fall Meeting chairs, for their development of anoutstanding conference.

xxi






MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS

Volume 467— Amorphous and Microcrystalline Silicon Technology—1997, M. Hack,E.A. Schiff, S. Wagner, R. Schropp, I. Shimizu, 1997, ISBN: 1-55899-371-1

Volume 468— Gallium nitride and Related Materials II, C.R. Abernathy, H. Amano,J.C. Zolper, 1997, ISBN: 1-55899-372-X

Volume 469— Defects and Diffusion in Silicon Processing, T. Diaz de la Rubia, S. Coffa,P.A. Stolk, C.S. Rafferty, 1997, ISBN: 1-55899-373-8

Volume 470— Rapid Thermal and Integrated Processing VI, T.J. Riley, J.C. Qelpey,F. Roozeboom, S. Saito, 1998, ISBN: 1-55899-374-6

Volume 471— Flat Panel Display Materials III, R.T. Fulks, Q.N. Parsons, D.E. Slobodin,T.H. Yuzuriha, 1997, ISBN: 1-55899-375-4

Volume 472— Poly crystal line Thin Films—Structure, Texture, Properties and Applications III,S.M. Yalisove, B.L. Adams, J.S. Im, Y. Zhu, F-R. Chen, 1997, ISBN: 1-55899-376-2

Volume 473— Materials Reliability in Microelectronics VII, J.J. Clement, R.R. Keller,K.S. Krisch, J.E. Sanchez, Jr., Z. Suo, 1997, ISBN: 1-55899-377-0

Volume 474— Epitaxial Oxide Thin Films III, D.Q. Schlom, C-B. Eom, M.E. Hawley,CM. Foster, J.S. Speck, 1997, ISBN: 1-55899-378-9

Volume 475— Magnetic Ultrathin Films, Multilayers and Surfaces—1997, J.Q. Tobin,D.D. Chambliss, D. Kubinski, K. Barmak, P. Dederichs, W.J.M. de Jonge,T. Katayama, A. Schuhl, 1997, ISBN: 1-55899-379-7

Volume 476— Low-Dielectric Constant Materials III, C. Case, P. Kohl, T. Kikkawa, W.W. Lee,1998, ISBN: 1-55899-380-0

Volume 477— Science and Technology of Semiconductor Surface Preparation, Q.S. Higashi,M. Hirose, S. Raghavan, S. Verhaverbeke, 1997, ISBN: 1-55899-381-9

Volume 478— Thermoelectric Materials—New Directions and Approaches, T.M. Tritt,M.Q. Kanatzidis, H.B. Lyon, Jr., Q.D. Mahan, 1997, ISBN: 1-55899-382-7

Volume 479— Materials for Optical Limiting II, R. Sutherland, R. Pachter, P. Hood, D. Hagan,K. Lewis, J. Perry, 1997, ISBN: 1-55899- 383-5

Volume 480— Specimen Preparation for Transmission Electron Microscopy of Materials IV,R.M. Anderson, S.D. Walck, 1997, ISBN: 1-55899-384-3

Volume 481— Phase Transformation and Systems Driven Far From Equilibrium, E. Ma,P. Bellon, M. Atzmon, R. Trivedi, 1998, ISBN: 1-55899-386-X

Volume 482— Nitride Semiconductors, F.A. Ponce, S.P. DenBaars, B.K. Meyer, S. Nakamura,S. Strite, 1998, ISBN: 1-55899-387-8

Volume 483— Power Semiconductor Materials and Devices, S.J. Pearton, R.J. Shul,E. Wolfgang, F. Ren, S. Tenconi, 1998, ISBN: 1-55899-388-6

Volume 484— Infrared Applications of Semiconductors II, S. Sivananthan, M.O. Manasreh,R.H. Miles, D.L. McDaniel, Jr., 1998, ISBN: 1-55899-389-4

Volume 485— Thin-Film Structures for Photovoltaics, E.D. Jones, R. Noufi, B.L. Sopori,J. Kalejs, 1998, ISBN: 1-55899-390-8

Volume 486— Materials and Devices for Silicon-Based Optoelectronics, J.E. Cunningham,S. Coffa, A. Polman, R. Soref, 1998, ISBN: 1-55899-391-6

Volume 487— Semiconductors for Room-Temperature Radiation Detector Applications II,R.B. James, T.E. Schlesinger, P. Siffert, M. Cuzin, M. Squillante, W. Dusi,1998, ISBN: 1-55899-392-4






MATERIALS RESEARCH SOCIETY SYMPOSIUM PROCEEDINGS

Volume 488— Electrical, Optical, and Magnetic Properties of Organic Solid-State MaterialsIV, J.R. Reynolds, A. K-Y. Jen, L.R. Dalton, M.F. Rubner, L.Y. Chiang, 1998,ISBN: 1-55899-393-2

Volume 489— Materials Science of the Cell, B. Mulder, V. Vogel, C. Schmidt, 1998,ISBN: 1-55899-394-0

Volume 490— Semiconductor Process and Device Performance Modeling, J.S. Nelson,CD. Wilson, S.T. Dunham, 1998, ISBN: 1-55899-395-9

Volume 491—Tight-Binding Approach to Computational Materials Science, P.E.A. Turchi,A. Qonis, L. Colombo, 1998, ISBN: 1-55899-396-7

Volume 492— Microscopic Simulation of Interfacial Phenomena in Solids and Liquids,S.R. Phillpot, P.D. Bristowe, D.Q. Stroud, J.R. Smith, 1998, ISBN: 1-55899-397-5

Volume 493— Ferroelectric Thin Films VI, R.E. Treece, R.E. Jones, S.B. Desu, CM. Foster,I.K. Yoo, 1998, ISBN: 1-55899-398-3

Volume 494— Science and Technology of Magnetic Oxides, M. Hundley, J. Nickel, R. Ramesh,Y. Tokura, 1998, ISBN: 1-55899-399-1

Volume 495— Chemical Aspects of Electronic Ceramics Processing, P.N. Kumta, A.F. Hepp,D.N. Beach, J.J. Sullivan, B. Arkles, 1998, ISBN: 1-55899-400-9

Volume 496— Materials for Electrochemical Energy Storage and Conversion II—Batteries,Capacitors and Fuel Cells, D.S. Qinley, D.H. Doughty, T. Takamura, Z. Zhang,B. Scrosati, 1998, ISBN: 1-55899-401-7

Volume 497— Recent Advances in Catalytic Materials, N.M. Rodriguez, S.L. Soled, J. Hrbek,1998, ISBN: 1-55899-402-5

Volume 498— Covalently Bonded Disordered Thin-Film Materials, M.P. Siegal, J.E. Jaskie,W. Milne, D. McKenzie, 1998, ISBN: 1-55899-403-3

Volume 499— High-Pressure Materials Research, R.M. Wentzocovitch, R.J. Hemley,W.J. Nellis, P.Y. Yu, 1998, ISBN: 1-55899-404-1

Volume 500— Electrically Based Microstructural Characterization II, R.A. Qerhardt, M.A. Alim,S.R. Taylor, 1998, ISBN: 1-55899-405-X

Volume 501—Surface-Controlled Nanoscale Materials for High-Added-Value Applications,K.E. Qonsalves, M-I. Baraton, J.X. Chen, J.A. Akkara, 1998, ISBN: 1-55899-406-8

Volume 502— In Situ Process Diagnostics and Intelligent Materials Processing,P.A. Rosenthal, W.M. Duncan, J.A. Woollam, 1998, ISBN: 1-55899-407-6

Volume 503— Nondestructive Characterization of Materials in Aging Systems, R.L. Crane,S.P. Shah, R. Gilmore, J.D. Achenbach, P.T. Khuri-Yakub, T.E. Matikas, 1998,ISBN: 1-55899-408-4

Volume 504— Atomistic Mechanisms in Beam Synthesis and Irradiation of Materials,J.C Barbour, S. Roorda, D. Ila, 1998, ISBN: 1-55899-409-2

Volume 505— Thin-Films—Stresses and Mechanical Properties VII, R.C Cammarata,E.P. Busso, M. Nastasi, W.C Oliver, 1998, ISBN: 1-55899-410-6

Prior Materials Research Society Symposium Proceedings available by contacting Materials Research Society






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