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Beschreibung

An overview of the tremendous potential of organic electronics, concentrating on those emerging topics and technologies that will form the focus of research over the next five to ten years. The young and energetic team of editors with an excellent research track record has brought together internationally renowned authors to review up-and-coming topics, some for the first time, such as organic spintronics, iontronics, light emitting transistors, organic sensors and advanced structural analysis. As a result, this book serves the needs of experienced researchers in organic electronics, graduate students and post-doctoral researchers, as well as scientists active in closely related fields, including organic chemical synthesis, thin film growth and biomaterials.

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Veröffentlichungsjahr: 2013

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Contents

Cover

Related Titles

Title Page

Copyright

Preface

List of Contributors

Chapter 1: Nanoparticles Based on π-Conjugated Polymers and Oligomers for Optoelectronic, Imaging, and Sensing Applications: The Illustrative Example of Fluorene-Based Polymers and Oligomers

1.1 Introduction

1.2 Nanoparticles Based on Fluorene Polymers

1.3 Nanoparticles Based on Fluorene Oligomer

1.4 Conclusions and Perspectives

Acknowledgments

References

Chapter 2: Conducting Polymers to Control and Monitor Cells

2.1 Introduction

2.2 Conducting Polymers for Biological Applications

2.3 Conducting Polymers to Control Cells

2.4 Conducting Polymers to Monitor Cells

2.5 Conclusions

References

Chapter 3: Medical Applications of Organic Bioelectronics

3.1 Introduction

3.2 Regenerative Medicine and Biomedical Devices

3.3 Organic Electronics in Biomolecular Sensing and Diagnostic Applications

3.4 Concluding Remarks

Acknowledgments

References

Chapter 4: A Hybrid Ionic–Electronic Conductor: Melanin, the First Organic Amorphous Semiconductor?

4.1 Introduction and Background

4.2 Physical and Optical Properties of Melanin and the Transport Physics of Disordered Semiconductors

4.3 The Hydration Dependence of Melanin Conductivity

4.4 Muon Spin Relaxation Spectroscopy and Electron Paramagnetic Resonance

4.5 Transport Model for Electrical Conduction and Photoconduction in Melanin

4.6 Bioelectronics, Hybrid Devices, and Future Perspectives

Acknowledgments

References

Chapter 5: Eumelanin: An Old Natural Pigment and a New Material for Organic Electronics – Chemical, Physical, and Structural Properties in Relation to Potential Applications

5.1 Introduction: The “Nature-Inspired”

5.2 Natural Melanins

5.3 Synthetic Melanins

5.4 Chemical–Physical Properties and Structure–Property Correlation

5.5 Thin Film Fabrication

5.6 Melanin Hybrid Materials

5.7 Conclusions

References

Chapter 6: New Materials for Transparent Electrodes

6.1 Introduction

6.2 Emergent Electrode Materials

6.3 Conclusions

References

Chapter 7: Ionic Carriers in Polymer Light-Emitting and Photovoltaic Devices

7.1 Polymer Light-Emitting Electrochemical Cells

7.2 Ionic Carriers

7.3 Fixed Ionic Carriers

7.4 Fixed Junction LEC-Based Photovoltaic Devices

7.5 Conclusions

References

Chapter 8: Recent Trends in Light-Emitting Organic Field-Effect Transistors

8.1 Introduction

8.2 Working Principle

8.3 Recent Trends and Developments

8.4 Conclusions

References

Chapter 9: Toward Electrolyte-Gated Organic Light-Emitting Transistors: Advances and Challenges

9.1 Introduction

9.2 Electrolyte-Gated Organic Transistors

9.3 Electrolytes Employed in Electrolyte-Gated Organic Transistors

9.4 Preliminary Results and Challenges in Electrolyte-Gated Organic Light-Emitting Transistors

9.5 Relevant Questions and Perspectives in the Field of EG-OLETs

Acknowledgments

References

Chapter 10: Photophysical and Photoconductive Properties of Novel Organic Semiconductors

10.1 Introduction

10.2 Overview of Materials

10.3 Optical and Photoluminescent Properties of Molecules in Solutions and in Host Matrices

10.4 Aggregation and Its Effect on Optoelectronic Properties

10.5 (Photo)Conductive Properties of Pristine Materials

10.6 Donor–Acceptor Composites

10.7 Summary and Outlook

Acknowledgments

References

Chapter 11: Engineering Active Materials for Polymer-Based Organic Photovoltaics

11.1 Introduction

11.2 Device Architectures and Operating Principles

11.3 Bandgap Engineering: Low-Bandgap Polymers

11.4 Molecular Acceptor Materials for OPV

11.5 Summary

References

Chapter 12: Single-Crystal Organic Field-Effect Transistors

12.1 Introduction

12.2 Single-Crystal Growth

12.3 MISFET

12.4 Schottky Diode and MESFET

12.5 Ambipolar Transistor

12.6 Light-Emitting Ambipolar Transistor

12.7 Electric Double-Layer Transistor

12.8 Conclusion

References

Chapter 13: Large-Area Organic Electronics: Inkjet Printing and Spray Coating Techniques

13.1 Introduction

13.2 Organic Electronic Devices – Operation Principles

13.3 Materials for Organic Large-Area Electronics

13.4 Manufacturing Processes for Large-Area Electronics

13.5 Conclusions

References

Chapter 14: Electronic Traps in Organic Semiconductors

14.1 Introduction

14.2 What are Traps in Organic Semiconductors and Where Do They Come From?

14.3 Effect of Traps on Electronic Devices

14.4 Detecting Traps in Organic Semiconductors

14.5 Experimental Data on Traps in Organic Semiconductors

14.6 Conclusions and Outlook

References

Chapter 15: Perspectives on Organic Spintronics

15.1 Introduction

15.2 Magnetoresistive Phenomena in Organic Semiconductors

15.3 Applications of Organic Spintronics

15.4 Future Developments

References

Chapter 16: Organic-Based Thin-Film Devices Produced Using the Neutral Cluster Beam Deposition Method

16.1 Introduction

16.2 Neutral Cluster Beam Deposition Method

16.3 Organic Thin Films and Organic Field-Effect Transistors

16.4 Organic Light-Emitting Field-Effect Transistors

16.5 Organic CMOS Inverters

16.6 Summary

Acknowledgments

References

Index

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All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

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A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at <http://dnb.d-nb.de>.

© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

Print ISBN: 978-3-527-41131-3

ePDF SBN: 978-3-527-65099-6

ePub ISBN: 978-3-527-65098-9

Mobi ISBN: 978-3-527-65097-2

oBook ISBN: 978-3-527-65096-5

Cover Design Simone Benjamin, McLeese Lake, Canada

Typesetting Thomson Digital, Noida, India

Preface

The goal of organic electronics, which uses thin films or single crystals of organic p-conjugated materials as semiconductors, is to enable technologies for large-area, mechanically flexible, and low-cost electronics. Intense research and development in organic electronics started in the 1990s, with the first demonstrations of light-emitting diodes, transistors, and solar cells based on organic semiconductors. Nowadays, organic electronic devices are becoming ubiquitous in our society. Displays based on organic light-emitting diodes are found in televisions, mobile phones, car stereos, and portable media players. Other devices, such as electrophoretic displays for electronic book readers and organic transistors for radio frequency identification tags, are expected to enter the market in the near future. In addition to the well-developed areas described above, exciting applications are envisaged in the field of organic bioelectronics, which takes advantage of the mixed ionic/electronic transport that can take place in organic electronic materials.

The purpose of this book is to cover recent developments in emerging topics of organic electronics, such as organic bioelectronics, spintronics, light-emitting transistors, and advanced structural analysis, to provide a large readership with a general overview of the enormous potential of organic electronics. We are convinced that the topics covered in this book will gain much momentum in the coming years.

This book will benefit different categories of readers such as graduate students, postdoctoral fellows, experienced researchers in organic electronics, and scientists active in fields close to organic electronics such as organic chemistry, bio and bio-inspired materials, and thin film engineering. Although rather focused on novel aspects, and therefore not offering a complete picture of organic electronics, we believe this book will become a useful reference for graduate students and postdoctoral researchers. For educational purposes, the book will constitute a perfect complement for academic graduate courses in organic electronics.

Clara SantatoFabio Cicoira

List of Contributors

Sareh Bayatpour

École Polytechnique de Montréal

Département de Génie Physique

2500 Chemin de Polytechnique

Montréal, QC H3T 1J7

Canada

Wade Braunecker

National Renewable Energy Laboratory

Chemical & Materials Science Center and National Center for Photovoltaics

15013 Denver West Parkway

Golden, CO 80401

USA

Jong-Ho Choi

Korea University

Research Institute for Natural Sciences

Department of Chemistry

1 Anam-dong

Seoul 136-701

Korea

Fabio Cicoira

École Polytechnique de Montréal

Département de Génie Chimique

2500 Chemin de Polytechnique

Montréal, QC H3T 1J7

Canada

John C. de Mello

Imperial College London

Centre for Plastic Electronics

Department of Chemistry

Exhibition Road

London SW7 2AZ

UK

Andrew Ferguson

National Renewable Energy Laboratory

Chemical & Materials Science Center and National Center for Photovoltaics

15013 Denver West Parkway

Golden, CO 80401

USA

Irén Fischer

Eindhoven University of TechnologyDepartment of Chemical Engineering and ChemistryFunctional Organic Materials & Devices GroupDen Dolech 25600 MB Eindhoven

The Netherlands

Salvador Gomez-Carretero

Karolinska Institutet

Swedish Medical Nanoscience Center

Department of NeuroscienceScheeles väg 1

17177 Stockholm

Sweden

Patrizio Graziosi

Consiglio Nazionale delle Ricerche Istituto per lo Studio dei Materiali Nanostrutturati

Via Gobetti 101

40129 Bologna

Italy

and

Universidad Politécnica de Valencia

Instituto de Tecnología de Materiale

Camino de Vera s/n 46022 Valencia

Spain

Yoshihiro Iwasa

The University of Tokyo

Quantum-Phase Electronics Center and Department of Applied Physics

7-3-1 Hongo

Tokyo 113-8656

Japan

Leslie H. Jimison

Physical Measurement Laboratory (PML)

Semiconductor & Dimensional Metrology Division

Microelectronics Device Integration Group (683.05)

100 Bureau Drive, M/S 8120

Gaithersburg, MD 20899-8120

USA

Oana D. Jurchescu

Wake Forest University

Department of Physics

1834 Wake Forest Rd

Winston-Salem, NC 27109

USA

Peter Kjäll

Karolinska Institutet

Swedish Medical Nanoscience Center

Department of NeuroscienceScheeles väg 1

17177 Stockholm

Sweden

Nikos Kopidakis

National Renewable Energy Laboratory

Chemical & Materials Science Center and National Center for Photovoltaics

15013 Denver West Parkway

Golden, CO 80401

USA

Janelle Leger

Western Washington University

Department of Physics

516 High Street

Bellingham, WA 98225-9164

USA

Paul Meredith

Centre for Organic Photonics & Electronics School of Mathematics and PhysicsUniversity of QueenslandSt Lucia CampusBrisbane, QLD 4072

Australia

Albertus B. Mostert

School of Mathematics and PhysicsUniversity of QueenslandSt Lucia CampusBrisbane, QLD 4072Australia

Jeong-Do Oh

Korea University

Research Institute for Natural Sciences

Department of Chemistry

1 Anam-dong

Seoul 136-701

Korea

Dana Olson

National Renewable Energy Laboratory

Chemical & Materials Science Center and National Center for Photovoltaics

15013 Denver West Parkway

Golden, CO 80401

USA

Oksana Ostroverkhova

Oregon State University

Department of Physics

Corvallis, OR 97331-6507

USA

Róisín M. Owens

Ecole Nationale Supérieure des

Mines de Saint EtienneCentre Microélectronique de ProvenceDepartment of Bioelectronics

880, route de Mimet

13541 GardanneFrance

Alessandro Pezzella

University of Naples “Federico II”

Department of Chemical Sciences

Complesso Universitario Monte S. Angelo

Via Cintia

80126 Naples

Italy

Thomas W. Phillips

Imperial College London

Centre for Plastic Electronics

Department of Chemistry

Exhibition Road

London SW7 2AZ

UK

Mirko Prezioso

Consiglio Nazionale delle Ricerche

Istituto per lo Studio dei Materiali

Nanostrutturati

Via Gobetti 101

40129 Bologna

Italy

Alberto Riminucci

Consiglio Nazionale delle Ricerche

Istituto per lo Studio dei Materiali

Nanostrutturati

Via Gobetti 101

40129 Bologna

Italy

Jonathan Rivnay

Ecole Nationale Supérieure des

Mines de Saint EtienneCentre Microélectronique de

ProvenceDepartment of Bioelectronics

880, route de Mimet

13541 GardanneFrance

Alberto Salleo

Stanford University

Department of Materials Science and Engineering

Stanford, CA 94305

USA

Clara Santato

École Polytechnique de Montréal

Département de Génie Physique

2500 Chemin de Polytechnique

Montréal, QC H3T 1J7

Canada

Jonathan Sayago

École Polytechnique de Montréal

Département de Génie Physique

2500 Chemin de Polytechnique

Montréal, QC H3T 1J7

Canada

Albertus P.H.J. Schenning

Eindhoven University of TechnologyDepartment of Chemical Engineering and ChemistryFunctional Organic Materials & Devices GroupDen Dolech 2

5600 MB Eindhoven

The Netherlands

Hoon-Seok Seo

Korea University

Research Institute for Natural Sciences

Department of Chemistry

1 Anam-dong

Seoul 136-701

Korea

Taishi Takenobu

Waseda University

Graduate School of Advanced Science and Engineering

Department of Applied Physics

3-4-1 Ohkubo

Tokyo 169-8555

Japan

Kristen Tandy

University of Queensland

School of Mathematics and Physics

Centre for Organic Photonics and Electronics

St. Lucia Campus

Brisbane, QLD 4072

Australia

Sam Toshner

Western Washington University

Department of Physics

516 High Street

Bellingham, WA 98225-9164

USA

Julia Wünsche

École Polytechnique de Montréal

Département de Génie Physique

CP 6079, Succursale Centre-Ville

Montréal, QC H3C 3A7

Canada

Jana Zaumseil

Universität Erlangen-Nürnberg

Lehrstuhl für

Werkstoffwissenschaften (Polymerwerkstoffe)

Martensstraße 7

91058 Erlangen

Germany

1

Nanoparticles Based on π-Conjugated Polymers and Oligomers for Optoelectronic, Imaging, and Sensing Applications: The Illustrative Example of Fluorene-Based Polymers and Oligomers

Irén Fischer and Albertus P.H.J. Schenning

1.1 Introduction

Nanoparticles based on π-conjugated polymers and oligomers have received considerable attention for optoelectronic and biological applications due to their small size, simple preparation method, and their tunable and exceptional fluorescent properties [1–7]. Nanoparticles are appealing for optoelectronic devices such as organic light-emitting diodes (OLEDs) [8,9], organic photovoltaic devices (OPVs) [10], and organic field-effect transistors (OFETs) [11] to gain control over the morphology of the active layer that plays a crucial role in the device performance. For example, in OPVs exciton dissociation occurs only at the interface of the donor and acceptor materials. Therefore, it is critical to control the donor–acceptor interface in order to optimize charge separation and charge migration to the electrodes [12,13]. The most common way to increase the interfacial area is by blending donor and acceptor materials making bulk heterojunction solar cells [14]. This necessary control over nanomorphology can be achieved by using nanoparticles to generate the active layer of the device [15]. Furthermore, the development of stable and fluorescent nanoparticles is interesting when combined with printing techniques to achieve large-area patterned active layers [6].

Nanoparticles based on π-conjugated systems show excellent fluorescence brightness, high absorption cross sections, and high effective chromophore density, which makes them attractive for imaging and sensing applications [1–5]. Fluorescence-based methods for probing biomolecular interactions at level of single molecules have resulted in significant advances in understanding various biochemical processes [16]. But there is currently a lack of dyes that are sufficiently bright and photostable to overcome the background fluorescence and scattering within the cell [17,18]. In addition, the photostability of the chromophore is critical for single-molecule imaging and tracking [19].

Here, an overview of the recent advances of nanoparticles based on fluorene oligomers and polymers is presented. We have chosen the illustrative example of fluorene-based π-conjugated systems to restrict this chapter but still show all aspects of nanoparticles based on π-conjugated polymers and oligomers. The fluorene moiety is a very favorable building block for π-conjugated systems because of its high and tunable fluorescence, high charge carrier mobility, and good solubility in organic solvents [20–24]. Furthermore, a large variety of fluorene-based polymers and oligomers can be created due to easy synthesis procedures [25,26]. Most organic nanoparticles for optoelectronic applications are prepared by the so-called miniemulsion method (Figure 1.1a) [27,28]. In this process, the π-conjugated system is dissolved in an organic solvent and then added to an aqueous solution containing surfactants. Stable nanoparticles are formed after sonication and evaporation of the organic solvent. The diameter of the nanoparticles can be reduced by increasing the surfactant concentration in the water solution or decreasing the polymer concentration in the organic solvent [29]. Nanoparticles in water for imaging and sensing applications are mostly prepared by the reprecipitation method in which a π-conjugated polymer or oligomer dissolved in THF solution is rapidly injected into water and subsequently sonicated (Figure 1.1b) [30,31].

Figure 1.1 Schematic representations of the preparation of the nanoparticles (a) by using the miniemulsion method and (b) by using the reprecipitation method.

Fluorescence energy transfer (FRET) in nanoparticles is an important tool to study their nanomorphologies for solar cells [32–34], tune their colors in OLEDs [35,36], and exploit them for sensing applications [37,38]. For an efficient energy transfer process, the emission spectrum of the donor should overlap with the absorption spectrum of the acceptor and the donor and acceptor need to be in close proximity, as the process highly depends on the distance between the donor and the acceptor (Eq. 1.1) [39].

The Förster energy transfer rate (kDA) for an individual donor–acceptor pair separated by a distance R is given by

(1.1)

where R0 is the Förster radius and τD is the natural lifetime of the donor in the absence of acceptors.

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