Triphenylene-based polymers for organic electronics [Elektronische Ressource] / vorgelegt von Moussa Saleh

Informations

• Publié par: johannes_gutenberg-universitat_mainz
• Publié le: 01 janvier 2010
• Nombre de lectures: 30
• Langue: English
• Poids de l'ouvrage: 14 Mo

Extrait

Triphenylene-based Polymers for Organic Electronics
Dissertation
zur Erlangung des Grades
“Doktor der Naturwissenschaften”
am Fachbereich Chemie, Pharmazie und Geowissenchaften der
Johannes Gutenberg-Universität Mainz
vorgelegt von
Moussa Saleh
geboren in Tripolis, Libyen
Mainz, 2010IITable of contents
Chapter 1. Foreword................................................................................................................ 1
1.1 Background on -Conjugated Polymers .................................................................... 3
1.2 Poly(para-phenylene)-Type Polymers as Blue-emitters............................................. 5
1.3 Synthetic Approaches to Poly(para-Phenylene)- Type Polymers .............................. 6
1.3.1 Oxidative condensation of aromatic hydrocarbons............................................ 7
1.3.2 Transition metal-mediated coupling reactions ................................................... 9
1.4 Organic Light Emitting Diodes ................................................................................ 18
1.4.1 Electroluminescence......................................................................................... 19
1.4.2 Basic processes and parameters in electroluminescent devices ....................... 19
1.4.3 Multilayer PLED devices ................................................................................. 23
1.5 General motivation................................................................................................... 25
1.6 References ................................................................................................................ 31
Chapter 2. Triphenylene-Based Conjugated Polymers for Blue Polymeric Light Emitting
Diodes .................................................................................................................. 40
2.1 Introduction .............................................................................................................. 40
2.2 Synthesis and characterization of conjugated polytriphenylenes............................. 44
2.2.1 Monomer synthesis........................................................................................... 44
2.2.2 Polymer synthesis............................................................................................. 48
2.3 Photophysical properties of triphenylene-based monomers and polymers.............. 55
2.3.1 Absorption and photoluminescence of triphenylene monomers ...................... 55
2.3.2 Optical properties of triphenylene-based polymers.......................................... 58
2.4 Electrochemical properties of triphenylene-based polymers ................................... 67
2.5 Thermogravimetric analysis (TGA) ......................................................................... 69
2.6 Supramolecular organization of triphenylene-based polymers................................ 70
2.6.1 Supramolecular organization of triphenylene-alt-arylene copolymers ............ 73
2.6.2 Supramolecular organization of polytriphenylene homopolymers .................. 76
2.7 Application of triphenylene-based polymers in polymeric light emitting diodes .... 78
2.8 Conclusions .............................................................................................................. 88
2.9 References ................................................................................................................ 91
Chapter 3. Triphenylene-Pyrene, Triphenylene-Fluorene, and Triphenylene-Carbazole-
based Copolymers for OLED applications ...................................................... 97
3.1 Introduction 97
3.2 Triphenylene-Pyrene copolymer (P )...................................................................... 9910
III3.2.1 Synthesis and characterization ......................................................................... 99
3.2.2 Photophysical properties of polymer P ........................................................ 10110
3.2.3 Electrochemical properties of polymer P .................................................... 10610
3.2.4 Application of Triphenylene-Pyrene co-polymer (P ) in blue PLEDs ......... 10810
3.3 Triphenylene-Fluorene co-polymers (P and P )................................................. 11211 12
3.3.1 Synthesis and Characterizations..................................................................... 112
3.3.2 Photophysical properties of polymers P and P .......................................... 11311 12
3.3.3 Electrochemical properties of polymers P and P ...................................... 11811 12
3.3.4 Differential scanning calorimetry (DSC) ....................................................... 119
3.3.5 Thermogravimetric analysis (TGA) ............................................................... 120
3.3.6 Supramolecular organization of polymers P and P ................................... 12111 12
3.3.7 Application of Triphenylene-Fluorene co-polymers (P and P ) in polymeric 11 12
light emitting diodes....................................................................................... 124
3.4 Triphenylene-Carbazole co-polymer (P ) ............................................................. 13113
3.4.1 Synthesis and characterization ....................................................................... 131
3.4.2 Photophysical properties of polymer P ........................................................ 13213
3.4.3 Electrochemical properties of polymer P .................................................... 13613
3.4.4 Differential scanning calorimetry................................................................... 137
3.4.5 Thermogravimetric analysis........................................................................... 138
3.4.6 Supramolecular organization of polymer (P ) .............................................. 13913
3.5 Conclusions ............................................................................................................ 143
3.6 References ................................................................................................................ 146
Chapter 4. From Triphenylene-based Polymers to Graphene Nanoribbons.................. 148
4.1 Introduction 148
4.2 Synthesis of GNRs using Scholl reaction conditions............................................. 152
4.2.1 Synthesis of 6,11-Bis-(4-tert-butyl-phenyl)-1,2,3,4-tetraphenyl-triphenylene
(model compound) ......................................................................................... 152
4.2.2 Synthesis of GNR-20...................................................................................... 156
4.2.3 Synthesis of GNR-21...................................................................................... 160
4.2.4 Synthesis of GNR-22...................................................................................... 165
4.2.5 Micro-Raman analysis.................................................................................... 168
4.3 Surface-mediated GNRs synthesis ......................................................................... 175
4.3.1 Synthesis of precursor monomers .................................................................. 176
4.3.2 Synthesis of GNRs ......................................................................................... 178
IV4.4 References .............................................................................................................. 185
Chapter 5. Outlook and Conclusion Remarks................................................................... 189
Chapter 6. Experimental Section........................................................................................ 194
Publication ............................................................................................................................ 223
VIndex of Abbreviations
CIE Commission Internationale de L’Eclairage
DCM dichloromethane
DSC differential scanning calorimetry
EL electroluminescence
ETL electron transporting layer
FD MS field desorption mass spectroscopy
FRET Forster resonance energy transfer
GPC Gel permeation chromatography
h hour
HBC hexa-peri-hexabenzocoronene
HBL hole blocking layer
HOMO highest occupied molecular orbital
ITO indium tin oxide
I-V-L current density and luminescence versus voltage
LUMO lowest unoccupied molecular orbital
MALDI-TOF matrix-assisted laser desorption ionization –time of flight
MeOH methanol
min minute
MS mass spectroscopy
NMR nuclear magnetic resonance
OLED organic light emitting diode
PAH polycyclic aromatic hydrocarbons
PEDOT:PSS poly(styrene sulphonic ester) doped poly(ethylenedioxy-
thiophene)
VIPF polyfluorene
PL photoluminescence
PLED Polymeric light emitting diode
RGB red, green, and blue
RT room temperature
STM scanning tunneling microscopy
TBAF tetrabutylammonium fluoride
TCNQ 7,7,8,8-tetracyanoquinodimethane
TGA thermogravimetric analysis
THF tetrahydrofuran
UV-vis ultraviolet/visible
WAXS wide angle X-ray scattering
VII Chapter 1
Chapter 1
Foreword
thWith the invention of the transistor around the middle of the 20 century, inorganic
semiconductors like