一、有機電激發光元件之新穎紅色客發光體材料的合成與應用 二、新穎綠色客發光體材料的合成與其元件穩定性質探討

Abstract

一、有機電激發光元件之新穎紅色客發光體材料的合成與應用 研究生：林葳君 指導教授：陳金鑫 博士 國立交通大學應用化學研究所 摘要 根據本實驗室研究經驗，在客發光體材料中引進具立體阻礙的第三丁基，能有效地提升元件發光效率與抗濃度驟息現象。因此我們合成出以DPP (6,13-diphenylpentacene)架構為主，且具立體阻礙的第三丁基之新穎紅色客發光體材料—6,13-di[4-(tert-butyl)phenyl]pentacene (簡稱2tb-DPP )與2,9-di-tert-butyl-6,13-bis-(4-tert-butyl-phenyl)-pentacene (簡稱4tb-DPP)。其中4tb-DPP的第三丁基位於pentacene上，但無論處於固態或溶於溶劑中都相當不穩定；然而在可自由旋轉的苯環上接有第三丁基的2tb-DPP，則發現其熱穩定度較DPP好，元件發光效率更提升了兩倍，而且色飽和度也獲得改善，當以濃度1.5%摻雜於主發光體Alq3時，CIEx,y座標值可達(0.626, 0.356)。 二、新穎綠色客發光體材料的合成與其元件穩定性質探討 研究生：林葳君 指導教授：陳金鑫 博士 國立交通大學應用化學研究所 摘要 我們擷取在julolidine環上接有五個具立體阻礙甲基的10-(1,3-benzothiazol-2-yl)-1,1,5,5,7-pentamethyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one (簡稱C-545P)分子設計的概念，其無論在發光效率或抗濃度驟息能力方面，都比市面上廣泛應用的10-(1,3-benzothiazol-2-yl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one (簡稱C-545T)要好；另一方面與僅具有「一半」julolidine結構，但化學結構較穩定的tetrahydroquinoline做結合，合成出新穎綠色客發光體材料—3-(1,3-benzothiazol-2-yl)-9-ethyl-6,8,8-trimethyl-6,7,8,9-tetrahydro-2H-pyrano[3,2-g]quinolin-2-one (簡稱C-543ET)，希望藉此保有此類含coumarin結構之綠色摻雜物良好的發光性質，同時提升分子的穩定度，並更進一步地提升元件穩定度。 經由UV輻射實驗證實，C-543ET在化學結構上比其他含coumarin結構之綠色摻雜物穩定，而且元件發光性質並沒有因結構改變而變差。在元件穩定性方面也初步發現，化學結構較穩定的C-543ET，其元件穩定度並不會隨摻雜濃度改變而改變；反之，C-545T的元件穩定度則會隨摻雜濃度的增加而降低。

Synthesis and Application of Novel Red Dopants for Organic Light Emitting Devices Student : Wei Chung Lin Advisor : Dr. Chin Hsin Chen Institute of Applied Chemistry National Chiao Tung University Abstract Bulky t-butyl substituted red dopants based on 6,13-diphenylpentacene (DPP) -- 6,13-di[4-(tert-butyl)phenyl]pentacene (2tb-DPP) and 2,9-di-tert-butyl-6,13-bis-(4-tert-butyl-phenyl)-pentacene (4tb-DPP) have been synthesized. It was observed that the presence of t-butyl groups on the pentacene skeleton actually made the materials less stable either in solid state or in solution. However, the incorporation of t-butyl groups onto the phenyl pendants as in 2tb-DPP, exhibited better thermal characteristics. At 1.5% doping concentration in device structure of ITO / CFx / NPB (110 nm) / wt% dopant + Alq3 (30 nm) / Alq3 (55 nm) / LiF / Al and 20 mA/cm2 constant current drive condition, the EL efficiency of 2tb-DPP attained 1.13 cd/A which is twice that of DPP and the color coordinates of CIEx,y = (0.626, 0.356). Synthesis and Device Reliability Study of Novel Green Dopants for Organic Light Emitting Devices Student : Wei Chung Lin Advisor : Dr. Chin Hsin Chen Institute of Applied Chemistry National Chiao Tung University Abstract We extracted the molecular design of which placed five methyl steric spacers on julolidine, whose luminance yield and resistance to concentration quenching were found to be better than the commercially available 10-(1,3-benzothiazol-2-yl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one (C-545T). A new green dopant -- 3-(1,3-benzothiazol-2-yl)-9-ethyl-6,8,8-trimethyl-6,7,8,9-tetrahydro-2H-pyrano-[3,2-g]quinolin-2-one (C-543ET) with stable tetrahydroquinoline of 〝half〞 julolidine skeleton was synthesized. It is expected to retain high luminance characteristics of 10-(1,3-benzothiazol-2-yl)-1,1,5,5,7-pentamethyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one (C-545P) as well as photoluminescent stability due to the lack of〝julolidine〞. By means of irradiation experiments, it was found that C-543ET is the most stable structure within the family of coumarin based green dopants, and the device performance of C-543ET is equal to C-545T. The operational device stability of C-543ET has been found to be independent of doping concentration which the lifetime of C-545T decreases with increasing dopant concentration.