順式二苯乙烯/芴螺旋體之三取代衍生物於有機電激發光二極體之應用

The Trisubstituted Derivatives of Spirally Configured cis-Stilbene/Fluorene Hybrid Templates for Organic Light Emitting Diode

張安泰(An-Tai Chang)

指導教授 ： 陳建添

國立清華大學/理學院/化學系所/碩士(2017年)

摘要

我們合成出以一系列順式二苯乙烯/芴螺旋體之三取代衍生物，期望能透過芴基片段延伸不同特性的官能基，能夠調控材料的載子傳輸和光電特性。本篇論文分為三個部分：第一個部分是將三取代衍生物應用於電子傳輸層；第二部分是合成天藍色螢光客體材料；第三部分是合成新型順式二苯乙烯/雙茚並芴雙螺旋體，並作為主體材料。
在第一部分中，我們在順式二苯乙烯片段的 C3,C7 位引入間氰苯基、吡啶，並在芴基片段的 C2’ 或是 C3’ 引入不同的推拉電子基團。應用於綠色磷光元件的電子傳輸層時，以 (mCNF)2S3PY 有最好的效能，在亮度 1,000 cd/m2 下，電流效率、功率效率與外部量子效率為 58.5 cd/A、56.9 lm/W 與 16.9%。應用於藍色螢光元件時，以(mCNF)2S2PY 有最好的效能，在亮度 1,000 cd/m2 下，電流效率、功率效率與外部量子效率為 9.9 cd/A、5.1 lm/W 與 7.5%。
在第二部分中，我們在順式二苯乙烯片段的 C3,C7 位引入二苯胺基，並在芴基片段的 C2’ 或是 C3’ 引入二苯胺基，分別為(DA)2S2DA 與 (DA)2S3DA。兩個螢光客體材料當搭配 AND均有TTA效應，效能超越一般螢光客體的 5% 理論效率。以 (DA)2S2DA 有最好的效能，在亮度 1,000 cd/m2 下，電流效率、功率效率與外部量子效率為 12.9 cd/A、5.8 lm/W 與 9.0%，並且 CIEy座標為0.21。
在第三部分中，我們合成了順式二苯乙烯/雙茚並芴雙螺旋體，為一個純碳氫化合物，並作為藍色螢光元件的主體材料時，在亮度 100 cd/m2 下，電流效率、功率效率與外部量子效率為 6.5 cd/A、2.5 lm/W 與 4.9%。作為橘紅色磷光元件的主體材料，在元件亮度 100 cd/m2 下，電流效率、功率效率與外部量子效率為 7.5 cd/A、5.8 lm/W 與 4.1 %。

關鍵字

順式二苯乙烯 ； 芴螺旋體 ； 有機電激發光二極體

並列摘要

In this thesis, a series of 3,7,2’/3’-trisubstituent spirally configured cis-stilbene/fluorene hybird derivatives were synthesized. The photoelectronic properties of these compounds have been tuned by modifying different functional group. These compounds were applied as electron transport layers, blue-emitting dopent and host materials.
Pyridine and benzonitrile groups were chosen to modify theelectron-transport properties of the cis-stilbene/fluorine hybrid core. The green phosphorescent device fabricated using (mCNF)2S3PY as electron transport layer showed the best performance with current efficiency of 58.5 cd/A, power efficiency of 56.9 lm/W, and external quantum efficiency (EQE) of 16.9% at 1,000 cd/m2. The blue fluorescent device fabricated using (mCNF)2S2PY as electron transport layer showed the best performance with current efficiency of 9.9 cd/A, power efficiency of 5.1 lm/W, and external quantum efficiency (EQE) of 7.5% at 1,000 cd/m2.
Diarylamine is a wisely used functional group for blue emitting and hole-transport materials. Incorporation of cis-stilbene/fluorine hybrids with diphenyl amine capping groups, skyblue fluorescent emitter materials were synthesized, named after (DA)2S2DA and (DA)2S3DA.When combined with AND, both of them showed the triplet-tirplet annihilation (TTA) effects. (DA)2S2DA exhibited high performance with current efficiency of 12.9 cd/A, power efficiency of 5.8 lm/W, EQE of 9.0% , and CIEy of 0.21 at 1,000 cd/m2.
A cis-stillene/6,12-dihydroindeno[1,2-b]fluorene hybrid, bisprially configured, model compound was also synthesized as fluorescent or PhOLED host material. Its resulting blue fluorescent device exhibits performance with current efficiency of 6.5 cd/A, power efficiency of 2.5 lm/W, EQE of 4.9% at 100 cd/m2, and orange phosphorescent device exhibits performance with current efficiency of 7.5 cd/A, power efficiency of 5.8 lm/W, EQE of 4.1% at 100 cd/m2.

並列關鍵字

cis-Stilbene ； Fluorene ； Spirally ； OLED

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