Conjugated semiconducting organic materials for electronic applications [Elektronische Ressource] / Changduk Yang

Changduk Yang

Sujets

• Physik

Informations

• Publié par: johannes_gutenberg-universitat_mainz
• Publié le: 01 janvier 2006
• Nombre de lectures: 39
• Langue: Deutsch
• Poids de l'ouvrage: 4 Mo

Extrait

Conjugated Semiconducting Organic Materials
for Electronic Applications


Dissertation


Zur Erlangung des Grades
“Doktor der Naturwissenschaften”


am Fachbereich Chemie, Pharmazie und Geowissenschaften der
Johannes Gutenberg-Universität in Mainz



Changduk Yang
geboren in Nonsan / Republic of Korea

Mainz, 2006






















Dekan:
1. Berichterstatter :
2. Berichterstatter :
Tag der mündlichem Prüfung Die vorliegende Arbeit wurde in der Zeit von 2003 bis 2006 im Max-Plannk-Institute für
Polymerforschung in Mainz unter Anleitung von Herrn Prof. Dr. K. Müllen ausgeführt.




















Ich danke Herrn Prof. Dr. K. Müllen für seine wissenschaftliche und persönliche
Unterstützung sowie für seine ständige Diskussionsbereitschaft.






















Table of Contents

List of Figures......................................................................................................................vi
List of Schemes...................................................................................................................xii
List of Tables......................................................................................................................xiv
List of Charts......................................................................................................................xv
Glossary of Abbreviations ................................................................................................xvi
Chapter 1 Introduction: Conjugated Polymers ..............................................................1
1.1 Conjugated Polymers; General ...................................................................................1
1.2 Organic Conductors from Doped Conjugated Polymers.........................................2
1.2.1 Principles of Conducting Polymers................................................................2
1.2.2 Mechanism and Methods of Doping ...........................................................7
1.2.3 Application of Doped Conjugated Polymers ................................................. 10
1.2.4 Polymeric Superconductors ........................................................................ 11
1.3 Organic Semiconductors from Undoped Conjugated Polymers ....................12
1.3.1 Background .............................................................................................12
1.3.2 Application of Undoped Conjugated Polymers ............................................. 13
1.3.3 Design and Configuration of Organic Light-Emitting Diodes (OLEDs)........... 16
1.3.4 Why are PLEDs important?......................................................................20
1.4 Motivation for the Present Work...........................................................................24
i1.4.1 Can metallopolymers be rendered highly conductive? ..............................24
1.4.1.1 Mechanisms of Conductivity in Metallopolymers..............................................................25
1.4.1.2 Materials Based on Bisthiazol-2-yl-amine Moiety ............................................................26
1.4.2 Can anthracene- and phenanthrene-based materials be suitable for use as
emitting materials? ...........................................................................................28
1.4.2.1 Conjugated Polymers Containing Anthracene Moiety......................................................28
1.4.2.2 Conjugated Polymers Containing Phenanthrene Moiety..................................................29
1.5 References .....................................................................................................................30
Chapter 2 Synthesis, Metal Complexation and Conductivity Studies on Bisthiazole
Analogues to Polyaniline ..................................................................................................35
2.1 Uncomplexed Conducting Materials .........................................................................36
2.1.1 Synthesis and Characterization ................................................................37
2.1.2 Photophysical and Electrochemical Properties..........................................43
2.2 Complexation Studies ..................................................................................................44
2.2.1 Ambipolar p-Type and n-Type Oligomer ..................................................47
2.2.2 Metallopolymers......................................................................................51
2.3 Conclusion.....................................................................................................................53
2.4 References .....................................................................................................................54
Chapter 3 Polymeric Materials Containing 9,10-Anthrylene Units...........................56
3.1 Polyphenylenes and Polyphenyleneethynylenes with 9,10-Anthrylene Subunits .....
..............................................................................................................................................57
3.1.1 Synthesis and Characterization ................................................................59
ii3.1.2 Electrochemical Properties.......................................................................64
3.1.3 Photophysical Properties..........................................................................65
3.1.4 Electroluminescence (EL) Properties .......................................................71
3.1.5 Conclusion............................................................................................... 72
3.2 Synthesis and Photochemical Properties of Ladderised Poly(p-phenylene-alt-9,10-
anthrylene)s ........................................................................................................................73
3.2.1 Synthesis and Characterization ................................................................75
3.2.2 Synthesis of model compounds (SLMC and LMC)..................................79
3.2.3 Photophysical Properties..........................................................................82
3.2.4 Thermal and Photochemical Properties.....................................................85
3.2.5 Electrochemical Properties.......................................................................89
3.2.6 Conclusion............................................................................................... 90
3.3 References .....................................................................................................................92
Chapter 4 Polymeric Materials Containing Phenanthrylene Units .............................95
4.1 Poly-2,7- and 3,6-phenanthrylenes as Polyphenylene and Polyphenylenevinylene
Analogues............................................................................................................................96
4.1.1 Synthesis and Characterization .............................................................. 100
4.1.2 Synthesis of 2,7- and 3,6-Linked Model Trimers and Their Characterization
...................................................................................................................... 109
4.1.3 Electrochemical Properties..................................................................... 110
4.1.4 Photoluminescence Properties................................................................ 112
4.1.5 Steady State Photoexcitation Dynamics.................................................. 121
iii4.1.6 Electroluminescence (EL) Properties ..................................................... 125
4.1.7 Thermal Stability of EL Devices ............................................................ 127
4.1.8 Dynamic Light Scattering Studies .......................................................... 130
4.1.8.1 Behavior of 3,6-PAP ...............................................................................................................130
4.1.8.2 Behavior of 2,7-PAP ...............................................................................................................132
4.1.9 Conclusion............................................................................................. 137
4.2 Columnar Mesophase Formation of Cyclohexaphenylene-based Macrocycles........
............................................................................................................................................138
4.2.1 Introduction.............................................................................................. 139
4.2.2 Thermal Characterization............................................................................ 141
4.2.3 Photophysical Studies ............................................................................ 142
4.2.4 Self-assembly Behavior ......................................................................... 143
4.2