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博碩士論文 etd-0719112-171627 詳細資訊
Title page for etd-0719112-171627
論文名稱
Title
新穎發藍光聚芳香醚高分子之合成及其在發光二極體上之應用研究
Synthesis Of Novel Blue-emitting Poly(arylene ether)s with Application to Light Emitting Diodes
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
94
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2012-06-28
繳交日期
Date of Submission
2012-07-19
關鍵字
Keywords
聚芳香醚、咔唑、三苯基胺、有機電激發光二極體、蒽
anthracene, triphenylamine, organic light emitting diode, carbazole, Poly (arylene ether) s polymer
統計
Statistics
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中文摘要
本論文主要以合成新穎藍光聚芳香醚高分子並將其製備成有機高分子發光二極體為研究。其中,主體材料為蒽(Anthracene)二氟單體之衍生物,客體材料為以三苯基胺(Triphenylamine)為延伸結構類似於文獻上所常看見的BD-1之非對稱衍生物,電洞傳輸材料則為結構中帶有咔唑(Carbazole)之二醇衍生物。一般而言,Anthracene衍生物及BD-1為文獻所常看見的主、客體藍光高分子摻雜,主體利用Forster energy transfer方式轉移能量至客體,因此具有良好的發光效率。但由於Anthracene之共平面性佳,在進行蒸鍍時易於結晶,導致漏電產生;且多層結構的蒸鍍亦會阻礙電荷注入到發光層。從分子設計的角度下,本研究(1)利用C-F鍵及Carbazole增加高分子鏈之立體障礙性及藉由氟化改變化合物的最高占用分子軌域-最低未占用分子軌域(HOMO-LUMO)能階位,(2)將電洞傳輸層導入發光層之中。將兩種單體Anthracene衍生物二氟單體及Carbazole之二醇衍生物依適當比例,經由親核性聚縮合反應合成出一種新穎藍光高分子。
在元件部份,將藍光聚芳香醚高分子摻雜少量藍光客體作為元件發光層,元件結構為:ITO/PEDOT:PSS/發光層/LiF/Al,發光層可利用溶劑製程旋轉塗佈方式製作,其優勢在於製程便利及可大面積化。未參雜客體前,藍光高分子製作PLED起始電壓可以降低至4.5 V、最大亮度為7466 cd/m2、效率高達4.2 cd/A。CIE座標方面 (0.15,0.08),相當接近NTSC的官方規定的藍光座標 (0.14,0.08)。當摻雜藍光客體3%時,起始電壓可以降低至4.5 V、最大亮度為12104 cd/m2、效率高達5.79 cd/A。
Abstract
In this thesis, a novel blue Poly (arylene ether) s polymer was prepared for the organic polymer light emitting diodes which was composed of the main material anthracene difluoro monomer derivatives, and object material of triphenylamine with the extension structure similar to the literature seen BD-1 asymmetric derivatives, as the hole transport material of carbazole of the diol derivatives. In general, Anthracene derivatives and BD-1, often seen in the literature as the host, guest blue polymer doping, the main use to Forster energy transfer to transfer energy to the guest, so it has good luminous efficiency. Anthracene, flat Good, easy to crystallization during evaporation, resulting in leakage generated; and the deposition of the multilayer structure will hinder charge injection to the emitting layer. From the angle of the molecular design of this study. (1) Use of the CF bond and Carbazole increase the steric hindrance of the polymer chain and change by fluoride compounds of the highest occupied molecular orbital - lowest unoccupied molecular orbital energy level. (2) The hole transport layer to import into the emitting layer. The two monomers Anthracene derivatives fluoride monomer the Carbazole of diol derivatives via nucleophilic polycondensation synthesis of a novel in proper proportion, Blue polymer.
Component parts, the Blue poly aromatic ether polymer doped with a small amount of blue light-emitting guest as a component layer of the component structure: ITO / PEDOT: PSS / emitting layer / LiF / Al light-emitting layer can make use of spin coating of solvent process, and its advantage is the convenience of the process and a large area. The undoped guest before the Blue polymer production the PLED starting voltage can be reduced to 4.5 V, and maximum brightness 7 466 cd/m2, efficiency as high as 4.2 cd / A. C.I.E. coordinates of (0.15,0.08), very close to the official regulations of the NTSC Blue coordinates (0.14,0.08). When doped with 3% of the guest, the starting voltage can be reduced to 4.5 V, maximum brightness of 12104 cd/m2 and efficiency as high as 5.79 cd/A.
目次 Table of Contents
摘要 i
Abstract ii
目錄 iv
圖次 vi
表次 vii
第一章 緒論 1
1.1 研究背景 1
1.2 有機發光二極體原理 5
1.3 能量轉移機制 7
1.3.1 輻射能量轉移 7
1.3.2 非輻射能量轉移 8
1.4 量子效率 9
1.5有機發光二極體OLED和PLED之比較 10
1.5.1 設備、製程層面 10
1.5.2 材料、元件層面 10
1.6 文獻回顧 11
1.7 研究動機 14
第二章 儀器介紹 15
2.1 藥品 15
2.2 熱示差掃描卡量計(Differential scanning calorimetry,DSC) 16
2.3 熱重分析儀(Thermogravimetric analyzer,TGA) 18
2.4 紫外與可見光光譜儀(UV-VIS SPECTROMETER,UV-Vis) 20
2.5 螢光光譜儀(Fluorescence spectrometer,PL) 22
2.6核磁共振光譜儀(nuclear magnetic resonance,NMR) 24
2.7傅利葉轉換式質譜儀(Fourier-transfer mass spectrometry,FT-MS spectrometry) 25
2.8 飛行時間式電荷傳輸特性量測系統(Time-of-Flight System,TOF) 26
2.9 偏光顯微鏡(Polarized Optical Microscopy,POM) 27
第三章 實驗 28
3.1材料製備流程 28
3.1.1藍光主體及電洞傳輸材料製備流程 28
3.1.2 藍光高分子及藍光客體製備流程 29
3.2 藍光單體合成 30
3.2.1 4-Fluoro-3-(trifluoromethyl)phenylboronic acid 30
3.2.2 9,10-bis(4-fluoro-3-(trifluoromethyl)phenyl)anthracene 32
3.3 電洞傳輸材料合成 34
3.3.1 3,6-dibromo-9H-carbazole 34
3.3.2 3,6-dibromo-9-(2-ethylhexyl)-9H-carbazole 36
3.3.3 9-(2-ethylhexyl)-3,6-bis(4-methoxyphenyl)-9H-carbazole 38
3.3.4 4,4'-(9-(2-ethylhexyl)-9H-carbazole-3,6-diyl)diphenol 40
3.4 藍光客體合成 42
3.4.1 2-((4-(4-bromobenzyl)phenyl)(phenyl)phosphino)benzene-1-ylium bromide 42
3.4.2 (E)-4-(4-bromostyryl)-N,N-diphenylaniline 43
3.4.3 (E)-4-(2-(3',4'-dimethoxy-[1,1'-biphenyl]-4-yl)vinyl)-N,N-diphenylaniline 45
3.5 藍光高分子合成 47
3.6元件 49
3.6.1 元件製作流程 49
3.6.2 基本元件 50
3.6.3 HOST-GUEST電激發光元件 50
第四章 結果與討論 52
4.1 材料分析 52
4.1.1單體熱裂解分析 52
4.1.2偏光顯微鏡與熱示差掃描卡量計 54
4.1.3 遷移率 57
4.2 材料光學分析(UV-Vis & PL) 59
4.3 元件量測 62
4.3.1 基本元件量測 62
4.3.2 HOST-GUEST電激發光元件 64
第五章 結論 66
參考文獻 67
附錄 70
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