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研究生： 許令揚
Hsu, Ling-Yang
論文名稱： 雙三配位銥金屬錯合物之合成暨有機發光二極體與生物影像的應用
Synthesis of Bis-tridentate Iridium (III) Complexes and Their Applications in Organic Light-Emitting Diodes and Bio-imaging.
指導教授： 季昀
Chi, Yun
口試委員: 陳建添
Chen, Chien-Tien
李紫原
Lee, Chi-Young
衛子健
Wei, Tzu-Chien
學位類別： 碩士
Master
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2019
畢業學年度： 107
語文別： 中文
論文頁數： 207
中文關鍵詞： 銥金屬 、雙三配位 、有機發光二極體 、生物影像
外文關鍵詞： Iridium, bis-tridentate, OLEDs, bio-imaging
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    • 本篇論文第一系列錯合物主要以 (C^N^N) 負二價配位基為發光團配位基 (chromophore)，搭配不同類型 [(C^N^N)、(C^N^C) 以及 (C^C^C)] 的負一價輔助配位基 (ancillary ligand)，合成出七個雙三牙配位銥金屬錯合物，其中包含中性及陽離子性的錯合物，藉由光物理性質及理論計算的結果，探討當負一價配位基用不同原子進行配位時，金屬與配位基間作用力的改變。由於中性錯合物結構剛性強、中心金屬與配位基交互作用力強，具有傑出的磷光量子效率與高的光穩定性，挑選天藍光錯合物 1.3 及 1.4 進行 OLEDs 元件製作，最大外部量子效率 (EQE) 可分別達 16.7% 及 14.6%。
    第二系列錯合物為第一系列的延伸，於 (C^N^C) 配位基上利用 2,4-bis(trifluoromethyl)phenyl 取代 2,4-difluorophenyl，並搭配不同的 (C^N^N) 配位基，合成出光色與第一系列錯合物截然不同的銥金屬磷光材料，進一步拓展了雙三牙配位銥金屬錯合物在 OLEDs 領域的發展性。
    第三系列的錯合物中，我們利用合成的方法製備出具水溶性的雙三牙配位銥金屬錯合物，首次將 3+3 系統成功應用於生物細胞顯像 (bio-imaging) 領域，用來作為生物體內氧氣的偵測 (oxygen sensing)。利用不同發光配位基及取代基的引入，衍伸出水溶性與生物毒性不盡相同的綠光及紅光發光材料，透過對光物理性質與分子特性的了解，為雙三牙配位銥金屬錯合物在生物細胞顯像領域的發展，開創了一條全新的道路。

    To the first series of complexes in this thesis, we have synthesized seven bis-tridentate iridium complexes bearing same chromophoric chelate (C^N^N) and with different ancillary chelates (C^N^N, C^N^C, and C^C^C), including neutral and cationic complexes. Based on the results of photophysical properties and theoretical calculations, the change of interaction between metal and the ligand was discussed when the monoanionic chelate was coordinated to the metal by using different atoms. The structural rigidity and stronger metal-ligand interaction play the key factor to account for excellent phosphorescence quantum yields and high photostability for the neutral complexes. Among them, we chose sky-blue complexes 1.3 and 1.4 for OLEDs fabrication, giving the external quantum efficiency exceeding 16.7% and 14.6%, respectively.
    The second series of complexes was an extension from the first series. By using 2,4-bis(trifluoromethyl)phenyl instead of 2,4-difluorophenyl in the (C^N^C) chelates, and with different (C^N^N) chelates, we synthesized a series of iridium complexes with different emission color compared to the first series of complexes, further expanding the development of bis-tridentate iridium complexes in the field of OLEDs.
    In the third series of complexes, we synthesized a new type of bis-tridentate iridium complexes with water-soluble characteristics. For the first time, the 3+3 system was successfully applied to the field of bio-imaging for oxygen sensing in living organisms. By using different chromophoric chelates or substituents, we have developed green and red emitters with different water solubility and biological toxicity. Through the understanding of photophysical properties and molecular properties in this series of complexes, we have opened up a new path for the development of bis-tridentate iridium complexes in the field of bio-imaging.

    摘要 1 Abstract 2 第一章、序論 9 第一節、螢光及磷光發光原理 10 第二節、磷光發光材料簡介 13 第三節、OLEDs 的原理及發展 14 一、OLEDs 歷史與簡介 14 二、OLEDs 元件製作與發光原理 15 第四節、磷光發光材料在生物影像 (Bio-imaging) 的發展 19 一、磷光發光材料於 Bio-imaging的優勢 19 二、使用於 Bio-imaging 之材料所需具備的特質 20 三、Bio-imaging 於氧氣偵測 (oxygen sensing) 的應用 21 第五節、文獻回顧 – 銥金屬磷光材料 23 一、銥金屬磷光材料於 OLEDs 的近代發展 23 二、銥金屬磷光材料於 Bio-imaging 的近代發展 38 第六節、研究動機 45 第二章、實驗合成 46 第一節、試藥與儀器 46 一、試藥 46 二、分析儀器及實驗方法 46 第二節、配位基之合成 50 一、C^C^C 配位基之合成 50 二、C^N^C 配位基之合成 53 三、C^N^N 配位基之合成 60 第三節、銥金屬錯合物之合成 70 一、第一系列銥金屬錯合物之合成 70 二、第二系列銥金屬錯合物之合成 77 三、第三系列銥金屬錯合物之合成 80 第三章、結果與討論 94 第一節、第一系列銥金屬錯合物 94 一、錯合物分子設計 94 二、錯合物晶體解析 95 三、光物理性質與分子特性探討 108 四、理論計算 113 五、電化學性質探討 118 六、光穩定測試探討 120 七、OLEDs 元件製備與探討 123 第二節、第二系列銥金屬錯合物 127 一、錯合物分子設計 127 二、錯合物晶體解析 127 三、光物理性質與分子特性探討 130 四、電化學性質探討 134 第三節、第三系列銥金屬錯合物 136 一、錯合物分子設計 136 二、光物理性質與分子特性探討 138 三、氧氣偵測能力 (oxygen sensing property) 探討 143 四、細胞毒性探討 145 五、細胞影像探討 146 六、動物實驗探討 149 第四章、結論 151 第五章、附錄 152 第一節、未收錄於正文的配位基與錯合物之合成 152 一、C^C^C 配位基之合成 152 二、C^N^N 配位基之合成 155 三、銥金屬錯合物之合成 160 第二節、pyrazole 與 triazole 錯合物比較 164 一、錯合物分子設計 164 二、光物理性質與分子特性探討 165 三、電化學性質探討 166 四、OLEDs 元件製備與探討 169 第三節、合成錯合物的失敗反應 173 第四節、嘗試優化雙三配位銥金屬錯合物合成產率 175 第五節、正文中錯合物光譜資料 181 第六節、附錄中錯合物光譜資料 197 第七節、參考文獻 203

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