1,3,2-苯並二氮雜硼衍生物之合成、性質探討及其在藍色磷光有機發光二極體及陰離子偵測之應用

Synthesis and Characterization of Substituted 1,3,2-Benzodiazaborole and Their Applications in Blue Phosphorescent Organic Light Emitting Diodes and Anion Detection

10.6342/NTU201703805

楊曉彤

硼氮吲哚 ； 有機含硼化合物 ； 1,3,2-苯並二氮雜硼 ； 陰離子偵測 ； OLED ； B-N indole ； organoboron ； 1,3,2-benzodiazaborole ； anion detection ； OLED

國立臺灣大學化學系學位論文

2017年

碩士

梁文傑

繁體中文

隨着藍光材料快速的發展，介於有機材料和無機材料之間的含硼化合物也引起廣泛的討論。因此，我們引入等電子體的概念，設計了一系列以1,3,2-苯並二氮雜硼為中心的分子。 我們成功克服立體障礙的限制，以取代基位置分為鄰位及間位系列，合成了具有不同的官能基的衍生物。因1,3,2-苯並二氮雜硼具有10個π電子及硼原子的空pz軌域，展示了獨特的光電性質，且其具有高三重態能階。故我們引入咔唑基團，以提高其熱穩定性，以及調整其傳電洞的能力，應用於藍色磷光有機發光二極體元件的製作。 元件部分以本系列熱穩定性最佳的dCb作為主發光材料，FIrpic為客發光材料之元件，最大亮度為11680 cd/m2，最大發光效率為18.07 Cd/A，最大發光功率為13.23 lm/W，最大外部量子效率為8.25%。以dCb作為電子阻擋層，最大亮度為20890 cd/m2，最大發光效率為51.66 Cd/A，最大發光功率為39.10 lm/W，最大外部量子效率為25.35%。 同時，我們也把本系列化合物應於陰離子檢測，對於F-及OH-最為明顯，於10-5M可以肉眼辦別。以目前初步的測試，此系列化合物具有作為多重離子偵離器的潛力。

For blue light emissing materials developed rapidly, not only the classic organic molecule, but also a new trend of organoboron draws attendion. We induce the concept of isostere of boron-nitrogen and carbon-carbon of indole to form B-N indole. This thesis reports a synthesis method of a series of 1,3,2-benzodiazaborole derivatives which is at the interface between organic and inorganic chemistry. Overcoming the steric effect, we achieved ortho substituted series and meta substituted series. With 10 π electrons and the empty p orbital of boron, these molecules show special photoproperties. The emission spectra reveal that 1,3,2-benzodiazaborole derivatives maintain high triplet energy. We induce carbazole to increase the thermal stability and adjust the hole transport ability for the application in blue phosphorescent organic light emitting diode(PhOLED). The PhOLED device with dCb as host, exhibits maximum luminance of 11680 cd/m2, maximum current efficiency of 18.07 cd/A, the maximum power efficiency of 13.23 lm/W, the maximum external quantum efficiency of 8.25%. The PhOLED device with dCb as electron blocking layer, shows maximum luminance of 20890 cd/m2, maximum current efficiency of 51.66 cd/A, the maximum power efficiency 39.10 lm/W, the maximum external quantum efficiency of 25.35%. In the anion detection experiment, we find out fluoride ion and hydroxide ion can be dectected by naked eye in 10-5M. These molecules have the potential application in sensor array for multianion detection.

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