本實驗室所開發之順式二苯乙烯/芴螺旋體系統之衍生物應用於有機光電材料已有10年歷史。在此，我們延續順式二苯乙烯/芴螺旋體系統，以含氮雜環之模板合成出一系列1-氮二苯環庚烯/芴螺旋體之衍生物，並在C3及C8位置上引入不同拉電子官能基及芳香胺官能基，期望能透過此全新模板發展出高效率之電子傳輸層以及客體發光材料。此外，我們合成出具有雙極性特徵之吖啶/芴螺旋體衍生物，嘗試將其應用於綠色磷光元件之電子傳輸層材料。
第一部分，我們於1-氮二苯環庚烯片段引入苯氰基、嘧啶、吡啶，將其應用於綠色磷光元件之電子傳輸層時，1-aza-STIF-mPhCN 和1-aza-STIF-ppy有最好的效能。在亮度1000 cd/m2下時，外部量子效率分別為 19.8% 和 20.5%，電流效率和功率效率分別為68.6 cd/A、67.6 lm/W和72.3 cd/A、58.5 lm/W。應用於藍色螢光元件時，1-aza-STIF-pmPh 和1-aza-STIF-ppy有亮眼的表現。在亮度1000 cd/m2下時，外部量子效率分別為 6.8% 和 7.3%，電流效率和功率效率分別為10.1 cd/A、3.6 lm/W和10.8 cd/A、5.5 lm/W。
第二部分，我們於1-氮二苯環庚烯片段引入二苯胺、三苯胺，將其應用於藍色螢光材料，在亮度1000 cd/m2下，搭配主體材料α,β-ADN時，摻雜 3 wt%的 dpa-aza-STIF-tpa 有最好的效能，在亮度 1,000 cd/m2 下，外部量子效率為 4.0%，電流效率和功率效率分別為 5.4 cd/A 、 2.3 lm/W，並且 CIEy座標為0.19，此外，摻雜1 wt%時CIEy座標為0.09，為具有潛力之深藍螢光客體材料。
第三部分，我們以吖啶/芴螺旋體為模板引入苯氰基，將其應用於綠色磷光元件之電子傳輸層材料時，以FNAc-mPhCN元件效能略勝一籌，在亮度1000 cd/m2下時，外部量子效率為 17.4% ，電流效率和功率效率分別為61.4 cd/A、55.6 lm/W。

Derivatives of cis-stilbene/fluorene system which applied to organic optoelectronic materials have been developed by our group for more than ten years. As a rational extension of our existing STIF systems, a series of spirally configured 1-azadibenzosuberene/fluorene (1-aza-STIF) derivatives were synthesized based on 1-azadibenzosuberenone template. Five different electron withdrawing groups or two different arylamino groups were attached on the C3 and C8 position of the core template. We expected that these compounds could be applied to electron-transporting materials (ETMs) and blue-emitting dopants in OLED applications in hope to achieve high efficiency by ultilizing the brand-new template. Moreover, two acridine/fluorene derivatives provided with bipolar characteristics have been synthesized and were applied to green phosphorescent organic light-emitting diodes (PHOLEDs) as ETMs.
Phenylcyano groups, pyrimidinyl groups, pyridinyl groups were chosen to optimize the electron-transporting properties based on previous experience. The green PHOLEDs using 1-aza-STIF-mPhCN and 1-aza-STIF-ppy , respectively, as electron transport layers exhibited the best performance with EQEs of 19.8% and 20.5%, CEs/PEs of 68.6 cd/A / 67.6 lm/W, and 72.3 cd/A / 58.5 lm/W at 1000 cd/m2. The blue fluorescent device fabricated by using 1-aza-STIF-pmPh and 1-aza-STIF-ppy, respectively, as electron transport layer showed the best performance with EQEs of 6.8% and 7.3%, CEs/PEs of 10.1 cd/A / 3.6 lm/W, and 10.8 cd/A / 5.5 lm/W at 1000 cd/m2, respectively.
In addition, arylamino groups were widely used as blue-emitting and hole-transport materials. Herein, we synthesized three compounds that acted as blue dopants by choosing diphenylamino groups and triphenylamino groups. When combined with the host material α,β-ADN, 3 wt% dpa-aza-STIF-tpa exhibited best performance with EQE of 4.0%, and CE/PE of 5.4 cd/A / 2.3 lm/W and CIEy of 0.19 at 1,000 cd/m2. Moreover, the device showed the CIEy of 0.09 at 1,000 cd/m2 when doping with 1 wt% dpa-aza-STIF-tpa, indicating it’s potential for deep-blue emitter.
On the other hand, two spirally configured acridine/fluorene derivatives which were combined with phenylcyano groups were applied to green PHOLEDs as ETMs. The results of device performance showed that FNAc-mPhCN were slightly better than the other, with EQE of 17.4%, and CE/PE of 61.4 cd/A / 55.6 lm/W at 1000 cd/m2.

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