中文摘要

OLED
我們利用上盤二苯并環庚烷 (dibenzosuberane) 10號跟11號位置上融合奎咢啉 (Quinoxaline) 系統且下盤片段融合不同的芳香族化合物形成螺旋烯分子 (helicene) 來討論其系列分子在有機電致發光材料上的運用。
首先我們在上盤喹咢啉 (Quinoxaline) 分子之對位位子融合上不同的官能基，希望借由結合雙功能性 (bifunction) 與偶極 (dipolar) 的特性，使材料之間更能有效形成光激子 (exciton)，並且利用這些系統的衍生物，去做一系列在有機電致發光材料的研究和探討。
而我們利用差相掃瞄卡計法 (DSC) 和熱重量分析儀 (TGA) 去測量這些系統的熱穩定性，除了以咔唑環 (flavone) 為下盤片段之化合物2e之熱穩定比較不好以外，對其他的系統而言熱穩定性質都不錯，其中當分子量越大或下盤片段之立障越大時，其熱穩定性就會越好。接著對這些系統的衍生物進行吸收，放射光譜，螢光量子產率的測量;同時也利用循環伏特安培法評估其氧化還原行為和測定其HOMO-LUMO能階。接著搭配合適的電子傳輸層或電洞傳輸層製作發光二極體元件，並測量其光電性質，目前以化合物1g作為發光層的效果最好，其最大波長為516 nm，其半波寬長為98 nm，且元件操作在電流密度20 mA/cm2時，電流效應 (Luminance Efficiency) 為7.21 cd/A，功率 (Power Efficiency) 為2.18 lm/W，外部量子效率 (External Quantum Efficiency) 為2.3 %。

NLO
我們用茀環 (fluorene) 之2，7號位置接上不同取代基為上盤而在下盤片段融合上咔唑環 (flavone) 分子，討論這個螺旋烯分子的非線性光學性質。這一類的分子有相當好的電荷轉移 (charge transfer) 特性可以誘導出非線性光學的性質，而其模式是藉由中間雙鍵扭張構形之變化使得fluorene上盤模版成為極優良的電子受體，而其電子受體之能力則由在C2和C7位置二芳香胺來調控。螺旋烯分子的上下盤有著扭曲的雙鍵結構，由已發表的文章指出，如果分子內的π-電子系統有著扭曲的結構，可以增強其非線性光學的特性。我們得到最大的非線性光學數值是化合物4h大小為5.1x10-45，比較標準品DANS 之8.8x10-46可以看得出來雖然我們的化合物缺少了好的電子受體，但是在C2和C7位置二芳香胺來調控下可得NLO性質高於DANS，故可以期待作為一個不錯的非線性光學材料。

Abstract

OLED
A series of helicene derivatives based on dibenzosuberane which is fused quinoxaline on position number 10 and number 11 were prepared for applications in organic light-emitting diodes. These molecular material structures are confirmed by NMR and single X-ray diffraction structures .
Differential scanning calorimetry and thermogravimetric analysis studies were carried out to measure the thermal stability of these molecular materials . The redox behaviors and HOMO / LUMO energy differences are evaluated by the cyclic voltammetry experiments. These compounds were subjected to optoelectronic studies by fabricated the OLEDs with a device configuration of ITO/ NPB / compound / Alq3 / LiF / Al . Among them , the compound 1g led to the best device performance and hold maximum external quantum efficiency of 2.3%.

NLO
We introduced the 2,7-substuted fluorene of helicene to be employed in non-linear optical materials. These molecular material structures are also confirmed by NMR and single X-ray diffraction structures.
From the UV-VIS and the emission spectra , we know about the stokes shift was very large in these compounds . And using DFT-calculation we can find the charge transfer happened very easy inside the molecular structure . Finally , we test the properties of NLO by EFISH , and the biggest value is the compound 4h (5.1x10-45) , compare to the standand DANS (8.8x10-46) .

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