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研究生:黃孝文
研究生(外文):Shiao-Wen Hwang
論文名稱:主鏈含孤立電子和電洞傳送性發光團之聚芳香醚的合成與光電性質
論文名稱(外文):Synthesis and Characterizations of New Poly(aryl ether)s Containing Isolated Hole and Electron Transporting Fluorophores
指導教授:陳 雲
指導教授(外文):Y. Chen
學位類別:博士
校院名稱:國立成功大學
系所名稱:化學工程學系碩博士班
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:198
中文關鍵詞:聚芳香醚高分子發光二極體
外文關鍵詞:poly(aryl ether)spolymer light emitting diodes (PLED)
相關次數:
  • 被引用被引用:5
  • 點閱點閱:184
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  • 下載下載:12
  • 收藏至我的研究室書目清單書目收藏:0
摘要

本論文將具有電子傳送能力的結構導入發光層主鏈中,用以增加高分子的電子親和性,並經由不同結構的電子傳送和電洞傳送性發光團共聚合,合成十六個含有電子傳送和電洞傳送單位的聚芳香醚高分子,進一步來探討其結構對光電性質的影響。
論文中以�w唑(carbazole)和含有雙苯乙烯基的3,6-�w唑(carbazole)、2,7-芴(fluorene)、2,6-�e(naphthalene)、1,4-苯(phenylene)衍生物單體,作為電洞傳送性發光團,並利用親核性取代反應與電子傳送性發光團單體(1,3,4-噁二唑衍生物或對-四聯苯衍生物)共聚合,合成一系列主鏈含孤立發光團之聚芳香醚高分子,各高分子均可溶於一般之有機溶劑,如四氯乙烷、氯仿。由光致發光(photoluminescence, PL)之研究可以發現,此一系列主鏈含孤立發光團之聚芳香醚高分子,其發光可分為三種情形:(1)高分子之發光由各發光團所貢獻,並保有孤立發光團的高發光效率;(2)在不同發光團間有能量轉移發生,高分子之發光波長和發光效率由能量受者決定;(3)高分子之發光波長比各發光團都長,這與分子鏈間的π-π交互作用有關,高分子薄膜之PL發光波長是在407~498 nm之間,屬於藍光和藍綠光的範圍內。由環伏測量(CV)證實電子是先由電子傳送區段注入,電洞先由電子傳送區段注入,因此高分子電子和電洞注入的能障,可以藉由電子、電洞傳送區段導入而同時降低。藉由各高分子單層元件的製作,可求得各高分子的電致發光光譜,其結果大部分與光致發光光譜一致,這表示電致發光與光致發光屬於同一個發光中心,另外,P1、P2、P10的電致發光光譜分別在480、475、550 nm處多出現了一明顯波峰,這是由於分子間激發態的形成所致。元件結果顯示,雖然高分子電子和電洞注入的能障確實降低,但由於孤立的結構使得電子和電洞還是必須克服各區段間的跳躍(hopping)能障,因此電子和電洞再結合不易,使得發光強度沒有預期的增加。
Abstract

In this work, electron and hole transporting fluorophores were introduced to the poly(aryl ether)s to increase the electron affinity (EA) and decrease the ionisation potential (IP). Sixteen poly(aryl ether)s consisting of alternate isolated hole-transporting and electron-transporting segments were synthesized from the nucleophilic displacement reaction of bis(fluoride) monomers with bis(phenol) monomers. The monomers of hole-transporting segments were synthesized by the Heck reaction. These hole-transporting segments include N-(2-ethylhexyl)-3,6-carbazole, N-(2-ethylhexyl)-3,6- bis(styryl)carbazole, 2,7-bis(styryl)-9,9-dihexyl-fluorene, 2,6-bis(styryl)- 1,5-dihexyloxy- naphthalene and 1,4-bis(styryl)-2,5-dihexyloxybenzene. The p-quaterphenyl or 1,3,4-oxadiazole derivatives were chosen as the electron-transporting segments. These poly(aryl ether)s are soluble in common organic solvents, and exhibit good thermal stability with 5% weight loss temperature above 400oC in nitrogen atmosphere. The photoluminescence emitted from these poly(aryl ether)s could be classified to three kind of types: (1) the emission of polymers contributed from each fluorophore; (2) the emission of polymers was dominated by the energy acceptor, the fluorophores with longer emissive wavelength, via reabsorption or energy transfer; (3) the emissive wavelengths of polymers were longer than each fluorophore due to the interchain interaction (such as excimer or exciplex). The emissive wavelengths of these poly(aryl ether)s are located at 407~498 nm in the blue visible region. The electrolumiescent spectra of most polymers are consistent with the PL spectra except P1、P2 and P10. The additional peaks appeared in the electrolumiescent spectra of P1、P2 and P10 were due to the emission of interchain exciton.
According to the results of cyclic voltammetry experiments, the hole and electron affinities of the isolated polymers can be promoted simultaneously by the introduction of hole and electron transporting segments. However, the isolated hole and electron transporting fluorophores in these poly(aryl ether)s function as hole and electron trap centers. The hole and electron cannot recombine via intrachain migration. Thus, we can imagine that the carrier-hopping barrier between the hole and electron transporting fluorophores may be a factor to influence the exciton formation.
目 錄
第一章 緒論
1-1 前言……………………………………………………………1
1-2 共軛高分子……………………………………………………2
1-3 共軛高分子溶解度之改善……………………………………4
1-4 影響LED發光效率的因素…………………………………8
1-4.1影響PL量子效率的因素……………………………………8
1-4.2多層結構對元件效率的改善………………………………11
1-5 研究目的與動機…………………………………………… …16

第二章 文獻回顧
2-1前言……………………………………………………………19
2-2分子軌域與分子能態間的躍遷……………………………19
2-3分子間激發態(interchain exciton)………………………………24
2-4發光波長之調整…………………………………………………27
2-5電極與有機層界面性質之調整…………………………………34
2-6含孤立發光團高分子……………………………………………37
2-7含電子電洞傳送結構之共聚高分子……………………………39

第三章 實驗內容
3-1 實驗儀器與裝置………………………………………………42
3-2 鑑定儀器………………………………………………………43
3-3物性測量儀器……………………………………………………43
3-4 藥品……………………………………………………………45
3-5 合成步驟與結果………………………………………………47
3-5.1具電洞傳送性單體的合成步驟……………………………47
3-5.2具電子傳送性單體的合成步驟……………………………59
3-5.3模式化合物之合成步驟……………………………………61
3-5.4聚芳香醚高分子之合成步驟………………………………64
3-6循環伏安實驗……………………………………………………66
3-7相對量子效率……………………………………………………69
3-8單層元件試作……………………………………………………70
3-9計算化學…………………………………………………………72

第四章 模式化合物之結構與物性研究
4-1前言………………………………………………………………94
4-2模式化合物之合成結果與鑑定……………………………94
4-2.1 具電洞傳送性單體之合成……………………………94
4-2.2 具電子傳送性單體之合成……………………………97
4-3模式化合物之光學性質…………………………………………99
4-3.1 電洞傳送性發光團…………………………………………99
4-3.2 電子傳送性發光團………………………………………106
4-3.3 模式化合物之相對量子效率……………………………108
4-4 結語……………………………………………………………110

第五章 含電洞傳送性�w唑雜環之聚芳香醚的合成與性質研究
5-1前言……………………………………………………………112
5-2高分子之合成與鑑定……………………………………112
5-3高分子之熱分析…………………………………………116
5-4高分子之光學性質………………………………………119
5-4.1高分子在溶液中的光學性質………………………119
5-4.2 三氟甲基和氰基側基對發光性質之影響………………128
5-4.3 高分子薄膜的光學性質……………………………129
5-4.4 高分子薄膜發光的熱穩定性………………………133
5-5 結語……………………………………………………………136

第六章 含電洞傳送性碳氫環(芴、�e或苯)之聚芳香醚的合成與性質研究
6-1前言…………………………………………………………137
6-2高分子之合成與鑑定……………………………………137
6-3高分子之熱分析…………………………………………140
6-4高分子之光學性質………………………………………141
6-4.1高分子在溶液中的光學性質………………………141
6-4.2 高分子薄膜的光學性質……………………………148
6-4.3 高分子薄膜發光的熱穩定性………………………153
6-5 結語……………………………………………………………156

第七章 含電子和電洞傳送性發光團之聚芳香醚的電化學性質
7-1前言……………………………………………………………157
7-2電化學性質之結果與討論………………………………157
7-3 結語……………………………………………………………168

第八章 含孤立電子和電洞傳送性發光團之聚芳香醚的電致發光研究
8-1前言……………………………………………………………170
8-2電致發光(EL)特性………………………………………170
8-3影響元件效能的因素…………………………………………176
8-3.1 ITO界面對元件效能的影響………………………176
8-3.2 孤立結構的影響…………………………………………181
8-4 結語……………………………………………………………183

第九章 總結……………………………………………………185

參考文獻……………………………………………………………187

著作目錄……………………………………………………………196

自述…………………………………………………………………198
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