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研究生： 星安娜
Andriana - Polisenawati
論文名稱： 合成苯乙炔-蒽之交替共軛高分子應用於光電材料上
Synthesis of poly(phenylene vinylene-alt-anthracene) derivatives for molecular and polymeric optoelectronic materials
指導教授： 游進陽
Chin-Yang Yu
口試委員: 堀江正樹
Masaki Horie
邱顯堂
Hsien-Tang Chiu
學位類別： 碩士
Master
系所名稱： 工程學院 - 材料科學與工程系
Department of Materials Science and Engineering
論文出版年： 2013
畢業學年度： 101
語文別： 英文
論文頁數： 93
中文關鍵詞： 苯乙炔-蒽之交替高分子 、有機太陽能電池 、順-反異構物
外文關鍵詞： Poly (phenylene vinylene-alt-anthracene), organic photovoltaics, cis-trans-vinylene
相關次數： 點閱：216  下載：0 
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    • 利用縮合反應可合成出含有順-反異構物結構之新型苯乙炔-蒽之交替共軛高分子可應用於有機發光二極體元件上。其分子間之排列方式及順-反異構物含量，決定其光學、電學、能隙及熱性質。分子間及分子內電荷轉移過程可由分子排列結構決定。其中9,10-苯乙炔-蒽之電荷轉移效率較1,5-苯乙炔-蒽為佳。由放光光譜可以得知1,5-苯乙炔-蒽之量子效應遠遠優於9,10-苯乙炔-蒽。

    The new poly(phenylene vinylene-alt-anthracene) derivatives for optoelectronic materials application were synthesized through wittig reaction to see the effect of positional isomerism of phenylene (vinylene-alt-anthracene) on molecular packing and their optoelectronic properties. The analysis of the structure and its properties reveals that π-conjugation, thermal stability and optical properties in this series is affected by different cis-trans conformation and its molecular packing. The charge-transport properties of the compounds are primarily controlled by the solid state packing which is slightly more efficient for the 9,10-distyrylanthracenes compare with 1,5- distyrylanthracenes. The optical and electronic properties of 9,10-distyrylanthracenes and 1,5-distyrylanthracenes were examined by UV-vis spectroscopy and cyclic voltammetry. This two isomers has relatively different photoluminescence emissive both in the solid state and in solution. 1,5-distyrylanthracenes has high fluoresence while 9-10-distyrylanthracenes appears to be more fluorescence quenching.

    Keywords: Poly (phenylene vinylene-alt-anthracene), organic photovoltaics, cis-trans-vinylene

    Abstract i 中文摘要 ii Acknowledgements iii Table of Content iv List of Tables vii List of Figures viii List of Schemes xi Chapter 1. Introduction and Aims 1 1.1. Introduction 2 1.2. Organic semiconductors 2 1.3. Band theory of solids 4 1.4. Introduction to semiconducting polymers 5 1.5. Excitations in conjugated polymers 7 1.6. Photoluminescence and Electroluminescence in the conjugated polymer 8 1.7. Charge transporting materials [21-22] 10 1.7.1. P-type semiconductors 12 1.7.2. N-type semiconductors 13 1.8. Introduction of Organic Light Emitting Diode (OLED) 14 1.9. Introduction of Poly(p-phenylene vinylene) 16 1.10. Introduction of anthracenes and its derivatives 17 1.11. Polymerization via Witting reaction 19 1.12. Aims of the project 22 Chapter 2. Synthesis of poly(phenylene vinylene-alt-anthracene) derivatives 23 2.1. Introduction 24 2.2. Synthesis and characterization 25 2.2.1. Monomer preparation 25 2.2.1.1. Synthesis of 1,4-xylene bis (triphenylphosphoniumbromide)-2,5-didodecyloxy (3) 25 2.2.1.2. Synthesis of anthracene-9,10-dicarbaldehyde (4) 27 2.2.1.3. Synthesis of anthracene-1,5-dicarbaldehyde (7) and anthracene-2,6-dicarbaldehyde (10) 30 2.2.2. Polymerization preparation via witting reaction 34 2.3. Characterization 41 2.3.1. Molecular weight 41 2.3.2. Thermal properties 43 2.3.3. Optical properties 45 2.3.3.1. UV-Vis absorption spectroscopy 45 2.3.4. Electrochemical characterization 51 Chapter 3. Conclusions 54 Chapter 4. Experimental Section 55 4.1. General procedures (Instrumentation and Materials) 56 4.2. Synthesis 57 4.2.1. Synthesis of bis-dodecyloxy benzene 57 4.2.1.1. Synthesis of 1,4-bis(octyloxy)benzene (1) 57 4.2.1.2. Synthesis of 1,4-bis(bromomethyl)-2,5-bis(octyloxy)benzene (2) 57 4.2.1.3. Synthesis of 2,5-didodecyloxy-1,4-xylene-bis (triphenylphosphonium bromide) (3) 58 4.2.2. Synthesis of Anthracenes dicarbaldehyde 59 4.2.2.1. Synthesis of anthracene-9,10-dicarbaldehyde (4) 59 4.2.2.2. Synthesis of 1,5 -diiodo-9,10-anthraquinone (5) 59 4.2.2.3. Synthesis of 1,5-diiodoanthracene (6) 60 4.2.2.4. Synthesis of anthracene-1,5-dicarbaldehyde (7) 61 4.2.2.5. Synthesis of 2,6-diiodo-9,10-anthraquinone (8) 61 4.2.2.6. Synthesis of 2,6-diiodoanthracene (9) 62 4.2.2.7. Synthesis of anthracene-2,6-dicarbaldehyde (10) 63 4.2.3. Synthesis of napthalene-based polymers 63 4.2.3.1. Synthesis of 9-(4-methyl-2,5-bis(octyloxy)styryl)-10-((E)-prop-1-enyl) anthracene (P1) 63 4.2.3.2. Synthesis of 1-(4-methyl-2,5-bis(octyloxy)styryl)-5-((E)-prop-1-enyl) anthracene (P2) 64 4.2.3.3. Synthesis of 9-(4-methyl-2,5-bis(octyloxy)styryl)-10-((E)-prop-1-enyl) anthracene (P1a) 65 4.2.3.4. Synthesis of 1-(4-methyl-2,5-bis(octyloxy)styryl)-5-((E)-prop-1-enyl) anthracene (P2a) 66 References 68 Appendix 73

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