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研究生： 蔡林仁
Tsai, Lin-Jen
論文名稱： 電激發光超分枝聚芴的合成與光電性質
Synthesis and Optoelectronic Properties of Electroluminescent Hyperbranched Polyfluorenes
指導教授： 陳雲
Chen, Yun
學位類別： 博士
Doctor
系所名稱： 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年： 2008
畢業學年度： 96
語文別： 英文
論文頁數： 172
中文關鍵詞： 超分枝 、聚芴
外文關鍵詞： hyperbranched, polyfluorene
相關次數： 點閱：61  下載：2 
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    • Several strategies have been made to minimize intermolecular interactions of polyfluorenes, such as longer and branched side chains or bulky substituents, copolymerization techniques, dendrimer attachment, end-capping with bulky groups, cross-linking, oligomer and hyperbranched structure approaches. Among them hyperbranched structures are one of the most versatile and promising ways to develop electroluminescent polymers with diminished intermolecular interactions and added functional groups. In this dissertation, we synthesized a series of totally new tri-functional branching monomers for the preparation of copolyfluorenes, such as 3,4,5-tris(4-bromo- phenyl)-4H-1,2,4-triazole (A), 3-(3,5-dibromophenyl)-5- (4-bromophenyl)-4-(4-(hexyloxy) phenyl)-4H-1,2,4-triazole (B), 2,4,7-tris(bromo- methyl)-9,9-dihexyl-fluorene (D), 2,4,7- tris[methylene(triphenyl-phosphonium bromide)]-9,9-dihexylfluorene (E) and 2-bromo- 5,7-divinyl-9,9-dihexylfluorene (F). Furthermore, the corresponding bi-functional monomers: 3-(3-bromophenyl)-5-(4-bromophenyl)-4-(4-(hexyloxy)phenyl)-4H-1,2,4- triazole (C), 2,7-bis(bromomethyl)-9,9-dihexylfluorene (D’), 2,7-bis[methylene(triphenyl- phosphonium bromide)]-9,9-dihexylfluorene (E’) and 2-bromo-7-vinyl-9,9- dihexylfluorene (F’) were also synthesized for the preparation of model linear polyfluorenes. All hyperbranched polymers were synthesized conveniently via a one-step polymerization by A3 + A’2 + B2, A3 + B2, A3, and AB2 approaches. All monomers and polymers were identified by 1H NMR, FT-IR and elemental analysis. The thermal properties of these polymers were analyzed with thermogravimetric analysis. The optical, electrochemical and electroluminescent properties of these polymers were investigated in detail to elucidate the branched structure-property relationship.
    In chapters 4~5, in order to suppress the interchain interaction, hyperbranched polyfluorenes HPFA (4%~22%) and HPFB (5%~13%) were polymerized by an A3 + A’2 + B2 approach via Suzuki coupling reaction. These polymers contain A (4~22 mol%) and B (4.8~13.3 mol%) as branch units. Model linear polyfluorenes LPFA0%, LPFB0% and LPFC (4%~13%) were also prepared for comparative studies. The hyperbranched polymers showed good solubility in common organic solvents such as CHCl3, toluene, and CH2Cl2 and exhibited excellent thermal stability with decomposition temperatures higher than 432oC. From optical absorption analysis, an interesting linear relationship between 1/λmax and 1/(1-ntriazole) were correlated for both HPFAs (4%~22%) and HPFBs (5%~13%), which was not observed in linear LPFC (4%~13%). The hyperbranched structures of HPFA4%~HPFA22% and HPFB13% suppress detrimental excimer formation (~550 nm) effectively during thermal annealing process. For HPFA6%~HPFA22%, however, a novel PL emission (~520 nm) was appeared after thermal annealing that had been attributed to complexes formed between triazole and pendant carbazole chromophores. The maximal brightness (current efficiency) of the electroluminescent devices (ITO/PEDOT:PSS/HPFB5%~HPFB13%/Ca/Al) was improved from 828 cd/m2 (0.19 cd/A) to 2054 cd/m2 (0.46 cd/A) with increasing triazole concentration. The results suggest that incorporation of aromatic 1,2,4-triazole branch units is effective in improving thermal stability and EL performance of polyfluorenes.
    In chapters 6~8, another series of novel hyperbranched structures (polymers and oligomer) HPFV0.04~HPFV0.17, HPFPPV-oxa and HOFV were synthesized using D, E and F as branching monomers, respectively. The HPFV0.04~HPFV0.17 were prepared by an A3 approach via the Gilch reaction, while HPFPPV-oxa was prepared by an A3 + B2 approach using the Wittig reaction followed by end-capping with oxadiazole compound. The HOFV was prepared by an AB2 approach using the Heck reaction. Linear model polymers LPFV0.17, LPFPPV-oxa and LOFV were also prepared for comparison. An interesting linear relationship between degree of branch (DB) and feed concentration ratio had been correlated for HPFV0.04~HPFV0.17. The HPFPPV-oxa showed energy funnel effect and enhanced fluorescence efficiency owing to hyperbranched structure. Electrochemical results and semi-empirical MNDO calculation for HPFV0.04~HPFV0.17, HOFV and HPFPPV-oxa revealed that reduction started from the dendritic unit and oxadiazole compound, respectively. The cross-linkable terminal vinyl groups of HOFV led to cured HOFV-cured after thermal treatment, which was confirmed by IR, DSC, absorption spectra, NMR, AFM and SEM. Furthermore, the electroluminescent performance of the devices (ITO/PEDOT:PSS/polymer/Ca/Al) were investigated and correlated with hyperbranched structures.

    Table of Contents Abstract …………………………………………………I Acknowledgments…… …………………………………III List of Schemes……… ………………………………VII List of Tables ………………………………………VIII List of Figures ………………………………………IX Chapter 1 Introduction of PLED and Hyperbranched Polymers 1-1 Development Background of PLED 1 1-2 Common Polymerization for Electroluminescent Polymers 4 1-3 Some Common Electroluminescent Fluorophore Derivatives 9 1-4 Introduction of Hyperbranched Polymers 1-4-1 Development Background of Hyperbranched Polymers 14 1-4-2 The General Synthesis Methodology of Hyperbranched Polymers 16 1-4-3 General Properties of Hyperbranched Polymers 18 1-4-4 Common Application of Hyperbranched Polymers 20 1-4-5 Review of Hyperbranched Structures for Electroluminescent Polymers 21 1-5 Research Motivation 24 Chapter 2 Review and Theoretical Background 26 2.1 Principle of Photoluminescence 26 2.2 The Quantum Yield 28 2-3 The Native of Emissive States 30 2-4 The Emission of Intermolecular Interaction 34 2-5 Energy Transfer and Funnel Effect 37 2-6 Semi-empirical MNDO Calculation 40 2-7 Degree of Branch (DB) in Hyperbranched Polymers 41 2-8 Color Matching Functions and Chromaticity Diagram 43 Chapter 3 Experimental Section 45 3-1 Instruments 45 3-2 Measurements 45 3-3 Materials 48 3-4 Synthetic Routes of Monomers and Polymers 50 3-4-1 Synthesis of Monomers 50 3-4-2 Synthesis of Polymers 61 Chapter 4 Novel Hyperbranched Polyfluorenes Containing Electron-transporting Triphenyl-1,2,4-triazole as Branch Unit 94 4-1 Introduction 95 4-2 Experiment 96 4-3 Result and Discussion 97 4-3-1 Synthesis and Characterization 97 4-3-2 Optical Properties 98 4-3-3 Electrochemical Properties 102 4-3-4 Device Properties 104 4-4 Summary 105 Chapter 5 Hyperbranched Luminescent Polyfluorenes Containing Aromatic Triazole Branching Units 106 5-1 Introduction 107 5-2 Experimental 108 5-3 Results and Discussion 109 5-3-1 Synthesis and Characterization 109 5-3-2 Optical Properties 110 5-3-3 Electrochemical Properties 114 5-3-4 Device Properties 115 5-4 Summary 118 Chapter 6 Hyperbranched poly(fluorenevinylene) from a 2,4,7-Tri-functional Fluorene Monomer with Different Degree of Branch 119 6-1 Introduction 120 6-2 Experiment 121 6-3 Results and Discussion 122 6-3-1 Synthesis and Characterization 122 6-3-2 Optical Properties 126 6-3-3 Electrochemical Properties 129 6-3-4 Device Properties 131 6-4 Summary 132 Chapter 7 Hyperbranched Copoly(fluorenevinylene) from a 2,4,7-Tri-functional Fluorene Monomer………………………………………………………..133 7-1 Introduction 134 7-2 Experiment 135 7-3 Results and Discussion 135 7-3-1 Synthesis and Characterization 135 7-3-2 Optical Properties 137 7-3-3 Electrochemical Properties 139 7-3-4 Device Properties 141 7-4 Summary 143 Chapter 8 Hyperbranched and Thermally Cross-linkable Oligomer from a New 2,5,7-Tri-functional Fluorene Monomer 144 8-1 Introduction 145 8-2 Experiment 146 8-3 Results and Discussion 146 8-3-1 Synthesis and Characterization 146 8-3-2 Optical Properties 152 8-3-3 Electrochemical Properties 154 8-3-4 Device Properties 156 8-4 Summary 158 Chapter 9 Conclusion 159 Referencnces and Notes 161 Appendix . 170 Curriculum Vitae 170 List of Publications 171

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