New design of polyphenylene dendrimers for full-color light-emitting diodes [Elektronische Ressource] / vorgelegt von Tianshi Qin

Tianshi Qin

Informations

• Publié par: johannes_gutenberg-universitat_mainz
• Publié le: 01 janvier 2010
• Nombre de lectures: 14
• Langue: English
• Poids de l'ouvrage: 28 Mo

Extrait

New Design of Polyphenylene Dendrimers
for Full-Color Light-Emitting Diodes

Dissertation

zur Erlangung des Grades
"Doktor der Naturwissenschaften"

dem Fachbereich Chemie und Pharmazie
der Johannes Gutenberg-Universität in Mainz
vorgelegt von

Tianshi Qin
geboren in Nanjing, P. R. China
Mainz, 2010

Table of contents
Chapter 1 Introduction: A mini-review of functioinzeadl polyphenylene
dendrimers ........................................................................... .1 ...................
1.1 Dendrimer chemistry - a short overv .ie.w.......................................... 1. .....
1.1.1 Divergent synthesis ................................................ .2. .........
1.1.2 Convergent synthesis ............................................. .4. ...........
1.2 Polyphenylene dendrime r.s........................................................................................... 4
1.3 Synthesis of polyphenylene dendrim .e.r.s......................................... 6. .....
1.4 Functionalization of polyphenylene dendrim e.r.s........................... 1.0. ...................
1.4.1 Functionalization in the Core .................................... .1.0. ...............
1.4.2 Functionalization on the scaffold ................................................. .1.3. .................
1.4.3 Functionalization on the surface ................................. .2.1. .................
1.5 Dendritic macromolecules for organic light-tienmgit diodes (OLEDs )..................... 24
1.6 Motivation ............................................................... 2.7 ..........
References ....................................................................................................................... 3.0. ..
Chapter 2 Polytriphenylene dendrimers: A unique digens for blue light-
emitting materials ........................................... .3.5. .....................
2.1 Motivation in design of blue fluorescent dmenerdsr i........................ ....................... 35
2.2 Blue fluorescent polytriphenylene dendrim .e.rs.................................... 3.9. .................
2.2.1 Design of cyclopentaphenanthrenone deriv aAtiBve-type building unit ....... 40 2
2.2.2 Synthesis of first- to third-generatiroipnh penolyletne dendrimers .............. 42
2.2.3 Characterization of the polytriphenylene rdimenedrs ..................................... 46
2.3 Visualization and simulatio .n....................................................................................... 49
2.3.1 Crystal structure of the first generatyitornip hpoenl ylene dendrimer ............ 49
2.3.2 Molecular modeling ............................................... .5.2. ...........
2.4 Physical properties of polytriphenylene denedrsim ........................4. ....................... 5
2.4.1 Photophysical properties in solution ............................. .5.4. ...................
2.4.2 Photophysical properties in thin film. ............................ .5.7 ....................
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2.4.3 Stability of polytriphenylene dendrime.r.s. ....................... .5.8. ......................
2.5 Blue OLEDs based on polytriphenylene dendrim e.r.s.....................6.0. ........................
2.5.1 Stability of polytriphenylene dendrimer b OaLsEeDds .................................... 60
2.5.2 Fabrication of polytriphenylene dendrimer ebda OsLEDs ............................... 62
2.5.3 Performance of polytriphenylene dendrimere db aOsLEDs ............................ 62
2.6 Blue fluorescent pyrene cored polytriphenyledneen drimers .................................. 68
2.6.1 Synthesis of pyrene cored polytriphenylened ridmeers ................................ 68
2.6.2 Characterization of pyrene cored polytriphleenney dendrimers .................... 70
2.6.3 Photophysical properties .......................................... .71. ..............
2.6.4 Comparison of PL and EL properties betweGe2n aTnPd PYG2 ....................... 74
2.7 Summar y.................................................................. 7.7 .......
References ....................................................................................................................... 8.0. ..
Chapter 3 A divergent synthesis of very large farics-[2t -phenylpyridyl]
iridium(III) cored polyphenylene dendrimers: molalerc usize effect on the
performance of green phosphorescent materials ................................ 85
3.1 Phosphorescent materials and their applicat ioinn sOLEDs ...................................... 85
3.2 Iridium(III) dendrimers, a self-host phospchenotr esystem .................................... 87
3.3 Green Phosphorescent Ir(ppyc)ored polyphenylene dendrimer s.......................... 90 3
3.3.1 Synthesis of the Ir( pdpeyr)ivative core ....................................... 91 3
3.3.2 Characterization of the Ir( pdpeyr)ivative core ......................................... .9.2. ...3
3.3.1 Synthesis of Ir(p pcoyr)ed polyphenylene dendrimers ....................... 93 3
3.3.4 Characterization of Ir(p pcoy)red polyphenylene .......................... .9.6 ..3
3.4 Visualization and simulation of Ir(p pcoyr)ed polyphenylene dendrimers ....... 99 3
3.4 Physical properties of Ir(p pcyo)red polyphenylene dendrimer s.......................... 101 3
3.4.1 UV-vis absorption and photoluminescence srpoescctopic measurements ... 101
3.4.2 Photoluminescence quantum yield ........................... .1.0.4. .......................
3.4.3 Electrochemical properties ...................................... .1.0.5. ...............
3.5 Green PhOLEDs based on Ir(ppy )cored polyphenylene dendrimer s.................... 106 3
3.5.1 Non-doped green phosphorescent OLEDs ............................................. 106
3.5.2 TCTA doped green phosphorescent OLEDs ............................................. 111
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3.6 Summar y................................................................ 1.1.4. .......
References .................................................................... 1.1.6. ...
Chapter 4 fac-Tris(2-benzo[b]thiophenylpyridyl)d iurim(III) cored
polyphenylene dendrimers with peripheral triphenymlaines: surface
functionalization of red phosphorescent materials. ............................. 122
4.1 From green to red – color tuning of Ir(pIlIeI)x ecso .m........................ ..................... 122
4.2 Red phosphorescent Ir(bt pc)ored polyphenylene dendrimer s............................ 124 3
4.2.1 Synthesis of Ir( bdtepr)ivative core ............................................................... 125 3
4.2.2 Synthesis and characterization of Ir (cbotrpe)d polyphenylene dendrimers 126 3
4.3 Physical properties of Ir(bctopr)ed polyphenylene dendrimer s........................... 130 3
4.3.1 UV-Vis absorption spectroscopic measureme.n.t ......................................... 130
4.3.2 Photoluminescence spectroscopic measuremen.t. ....................................... 132
4.3.3 Electrochemical properties ...................................... .1.3.4. ...............
4.4 Red PhOLEDs based on Ir(bt pc)ored polyphenylene dendrimer s........................ 135 3
4.5 Theoretical study on the lowest excited stfa teir idoium(III) complexe s............... 138
4.6 Red phosphorescent Ir(piq c)ored polyphenylene dendrimer .s............................ 140 3
4.7 Comparison of photophysical properties betwdeiefnf erent Ir(III) cor e.s............. 142
References .................................................................... 1.4.8. ...
Chapter 5 Conclusion and outlook .............................................. 152
Chapter 6 Experimental section .................................................. 159
6.1 Reagents and analysis instrume n.t.s............................................... 1.59
6.2 General synthetic procedures ........................................................ 162
6.3 Syntheses of the blue fluorescent dendrimehrasp (teCr 2 ).................................... 163
6.4 Syntheses of the Green Phosphorescent dendrsim (eCrhapter 3.)........................ 178
6.5 Syntheses of red phosphorescent dendrimers p(tCerh a4 ).................................... 190
Publication and Patent ............................................................ 205
Curriculum Vitae .............................................................0.6. .................... 2
Acknowledgements......................E.r.ro .r.!. B..o.o.k.m..a.rk not defin ed.

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Index of Abbreviations
AFM atomic force microscopy
Alq 8-hydroxyquinolinealuminum 3
ATRP atom transfer radical polymerization
CAN cerium ammonium nitrate
CBP 4-bis-(carbazol-9-yl)biphenyl
CIE Commission Internationale de L’Eclairage
CV cyclic voltammetry
DCM dichloromethane
EL electroluminescence
EQE extern quantum yield
ETL electron transporting layer
FD MS field desorption mass spectroscopy
FRET Förster resonance energy transfer
FWHM full width of half maximum
GPC Gel permeation chromatography
HBL hole blocking layer
HOMO highest occupied molecular orbital
Ir(btp) fac-tris(2-benzo[