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標題: | 含不同電性與具有咔唑立障結構之芘基衍生物合成、性質探討以及在藍光有機發光二極體的應用 Synthesis and Characterization of Pyrene Derivatives Containing Different Electricity and Ortho-linked Carbazole Substituted and Their Applications in Blue Light Organic Light Emitting Diodes |
作者: | 張琦琦 Chi-Chi Chang |
指導教授: | 梁文傑 Man-kit Leung |
關鍵字: | 苯並咪唑,咔唑,芘,生命期,深藍色有機發光二極體, benzimidazole,carbazole,pyrene,lifetime,ifespan,blue organic light emitting diode, |
出版年 : | 2022 |
學位: | 碩士 |
摘要: | 本論文設計不同電性的取代基,分別為具有拉電子性之苯並咪唑(Benzimidazole,Bz) 和具有推電子性之咔唑 (Carbazole,Cbz),接在芘 (Pyrene)的1號碳上,合成化合物 BzP 和 CbzP,以及將咔唑連接在1-苯基芘 (1-phenyl pyrene) 的苯環兩側鄰位和對位上,合成化合物 D-CbzP 和 T-CbzP。
由於過往的研究報導中,尚未有相關研究明確指出是哪一原因極大程度影響了芘系統之元件生命期 (Lifetime),於是本文設計了三項實驗,透過系統化的方式逐一排除可能主導芘基系統在元件壽命耗損的原因,利用化合物 BzP 和 CbzP 之拉、推電子性質,可穩定或改善在發光二極體工作中可能產生的帶不同電性的自由基(Radical),期許找出主導芘基系統之元件生命期的關鍵原因,延長元件的使用壽命;化合物 D-CbzP 和 T-CbzP則利用扭曲且擁擠的構象,避免分子間的芘環距離過近產生高能量的激發雙體 (Excimer) 造成元件損耗,也預防了 π-π 堆疊 (π-π stacking) 作用,維持深藍色光之發光表現。 元件表現上,材料的光色皆落在深藍色到藍色的範圍,化合物 T-CbzP 有最佳的放光表現,最大發光效率為15.95 cd/A,最大發光功率為12.55 lm/W,最大外部量子效率 (EQE) 達12.09 %,為一優秀之doped深藍色有機發光二極體。化合物 BzP 也有不錯的放光表現,最為突出的是極佳的生命期 (T50) 長達164分鐘,綜合密度泛函理論 (DFT)、晶體數據、電化學數據等分析後,推測當傳遞電子電洞的芘基之排列為平行且距離適當的情況下,傳遞通道順通無阻將有助於生命期的延長,但引導芘基系統元件獲得高生命期的原因還需要更多的研究討論、包含造成元件耗損的原因與機制等等。 In this thesis, substituents with different electrical properties (electron-withdrawing benzimidazole and electron-pushing carbazole) were designed, which were attached to the C1-linked to pyrene unit, named BzP and CbzP. And synthesized D-CbzP and T-CbzP by connecting carbazole to the ortho and para positions of the 1-phenylpyrene. Since the previous reports, there is no relevant research that clearly pointed out what dominates the lifetime of the pyrene system components extremely. Therefore, three experiments were designed in this thesis to systematically exclude the possibly dominant lifetime of pyrene groups one by one. The method finding out the components consume the life is that push-pull electronics of BzP and CbzP can be used to stabilize the radicals with different charges which may be generated in OLED. Hope to find out the key reasons that dominate the life of the components of the pyrene-based system to extend the life of the components. Another method is to use the distorted and crowded D-CbzP and T-CbzP to avoid the intermolecular pyrene-pyrene too close to generate high-energy unstable excimers, which cause component loss, and steric hindrance prevent π-π stacking to maintain the light color performance of dark blue light. In terms of component performance, the light color of the materials falled in the dark blue to blue range. T-CbzP has the best luminous performance, the maximum current efficiency is 15.95 cd/A, the maximum power efficiency is 12.55 lm/W, and the external quantum efficiency is 12.09 %, which is an excellent doped dark blue organic light emitting diode. BzP also exhibits good performance, most notably an excellent lifetime (T50) of 164 minutes. After comprehensive analysis of density functional theory, single crystal data, electrochemical data, etc., it is speculated that when the pyrene groups that transmit electrons and holes are arranged in parallel and the distance is appropriate, the unobstructed transmission channel will help to prolong the life span. However, the reason that lead the pyrene-based system components to obtain a high lifetime still need more research and discussion, including the causes and mechanisms of component wear and tear, and so on. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/87292 |
DOI: | 10.6342/NTU202204233 |
全文授權: | 同意授權(全球公開) |
電子全文公開日期: | 2024-09-30 |
顯示於系所單位: | 化學系 |
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ntu-111-1.pdf 此日期後於網路公開 2024-09-30 | 5.4 MB | Adobe PDF |
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