旋環雙芴衍生物與濕式製程有機發光二極體材料之開發探究及其光電應用

Chi-Yen Lin; 林季延

請用此 Handle URI 來引用此文件： http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48736

完整後設資料紀錄

DC 欄位	值	語言
dc.contributor.advisor	汪根欉
dc.contributor.author	Chi-Yen Lin	en
dc.contributor.author	林季延	zh_TW
dc.date.accessioned	2021-06-15T07:11:09Z	-
dc.date.available	2015-10-22
dc.date.copyright	2010-10-22
dc.date.issued	2010
dc.date.submitted	2010-10-11
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dc.identifier.uri	http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48736	-
dc.description.abstract	1. 以旋環雙芴為主體材料之光電應用以旋環雙芴為主體的寡聚合物或高分子材料，近年來常被應用於有機光電材料之研究中。本論文裡我們在其2,2'的位置引入左右不對稱之取代基團，此兩相正交相互獨立的共軛鏈，除可避免分子堆疊外，更使欲設計之分子具光學異構物之特質。首先，我們將帶有二羫基之旋環雙芴與拆旋試劑作用，可分離出左旋之(S)-BrSOH及右旋之(R)-BrSOH，最後再引入發光基團pyrene，即可合成出具有旋極化放光之發光材料 (glum ~ 0.001)。此外，在此正交之旋環雙芴核心架構下，我們引入推拉電子基團，使兩兩錨定基團之距離為10.05 A，讓其能夠以類似N719 的雙牙基形式緊緊吸附於TiO2上，提高吸附率，進而達到高效率之染料光敏化太陽能電池 (3.75%)。最後，我們更將左右不對稱之推拉旋環雙芴衍生物 (CN1) 吸附在金的電極表面進行電聚合反應，藉由調控電化學沉積之週期來修飾金電極表面之功函數。 2. 濕式製程有機發光二極體材料之開發探究相較於真空沉積技術，濕式製程具有製備簡單及成本低廉的特性，可望成為下一代OLEDs面板的主流。因此，本論文構想即針對如何克服薄膜材料對塗佈或噴印溶劑的穩定性問題加以探討，並進一步瞭解其複雜的介面關係。其中我們所開發之新型交聯式材料及離子性電子傳輸材料便可有效克服溶劑侵蝕或混合到前一層薄膜材料之問題。首先，我們合成出一系列熱聚型電洞注入材料、電洞傳輸材料、發光材料及電子傳輸材料。此類材料塗佈於基板後，可經由交聯聚合反應以達到抗溶劑侵蝕的效果。其中，熱聚型電洞傳輸材料具有相當高的穩定度及載子傳導特性 (大約 10-4 cm2 V-1 s-1)。原子力顯微鏡則進一步提供我們熱聚分子薄膜形貌的資訊，對於我們在聚合材料評估、開發及元件應用可做完整且有系統的研究。最後，離子性電子傳輸材料可藉由溶劑極性之不同，成功塗佈並製備多層式OLED元件。我們更針對其側鏈取代離子之不同，量測其電荷傳導特性及元件表現。另外，退火對於離子性共軛高分子之影響，可藉由Hofmann elimination來解釋側鏈離子之脫附。其操作機制可以由電子傳輸層之厚度及離子密度來加以調控。	zh_TW
dc.description.abstract	1. Spirobifluorene-Based Materials for Optoelectronic Applications Recently, molecules possessing a 9,9'-spirobifluorene core are used widely in organic optoelectronics. In this dissertation, different functional groups were introduced to form 2,2'-A,7,7'-B-substituted spirobifluorene (left-right asymmetric). The bridging of two chromophores perpendicularly via a sp3-hybridized atom into a spiro configuration hinders the aggregation between molecules. In addition, optically active enantiomer is possible to obtain in the left-right asymmetric system. First, (S)-BrSOH and (R)-BrSOH were resolved by clathrate formation between racemic dissymmetric 2,2'-dihydroxy-7,7'-dibromo-9,9'-spirobifluorene and the resolving reagent. New enantiomerically pure spiro compounds bearing pyrene moieties were synthesized and capable of preferentially absorbing and emitting circularly polarized light (glum ~ 0.001). Second, a new dye (SSD1) featuring two donor/acceptor chromophores aligned in a spiro configuration with two anchoring groups separated at a distance of 10.05 A (closely matching the distance between the adsorption sites of the anatase TiO2 surface) undergoes efficient dye adherence on TiO2 films. A dye-sensitized solar cell incorporating SSD1 exhibited a power conversion efficiency of 3.75%. Third, spirobifluorene-based donor (triphenylamine)–acceptor (cyano) bipolar systems has been investigated. Organic films (CN1) were formed on gold electrode by electrochemical polymerization. The gold surface work function can be changed over more than 0.4 eV depending on the numbers of electrochemical deposition cycles. 2. Development of All Solution-Processed Multilayer Organic Light-Emitting Diodes (OLEDs) Compared to vacuum deposition technique, solution-based deposition is more attractive for next generation OLEDs because of the simple process and low instrumental cost. The overall theme of this dissertation is to overcome the difficulty in achieving purely all-solution processing multiple-layer OLEDs and understanding the resulting complex interfaces. In order to alleviate the interfacial mixing problem, two promising approaches are investigated here. The first approach is the use of an organic-soluble precursor that becomes insoluble through crosslinkable reactions. With such a concept, thermally crosslinkable hole injection materials (HIMs) and/or hole transport materials (HTMs), emitting materials (EMs), and electron transport materials (ETMs) were designed and synthesized. These crosslinked HTMs, studied using time-of-flight techniques, exhibited remarkable stability and non-dispersive hole transport properties, with values of	en
dc.description.provenance	Made available in DSpace on 2021-06-15T07:11:09Z (GMT). No. of bitstreams: 1 ntu-99-F94223012-1.pdf: 15894753 bytes, checksum: 5b544618e9da25cff02d1d3549a67627 (MD5) Previous issue date: 2010	en
dc.description.tableofcontents	Part I Spirobifluorene-Based Materials for Optoelectronic Applications 1 Spirobifluorene-Based Materials for Optoelectronic Applications 1 1.1 Introduction 1 1.1.1 Spirobifluorene with Asymmetric Substitution Patterns on the Fluorene Units 2 1.1.2 Optoelectronic Applications of Spirobifluorene-Based Materials 4 1.2 Chiral 2,2',7,7'-Substituted Spirobifluorenes and Their Chiroptical Properties 8 1.3 Spirobifluorene Derivative for Dye-Sensitized Solar Cell Application 22 1.4 Engineering of Gold Surface Work Function by Electrodeposition of Spirobifluorene Donor-Acceptor Bipolar Systems 34 1.5 Conclusions 52 1.6 Experimental details 54 1.7 References 68 Part II Development of All Solution-Processed Multilayer Organic Light-Emitting Diodes (OLEDs) 2 Crosslinkable Organic Materials for Use in Organic Light-Emitting Diodes 75 2.1 Introduction 75 2.1.1 Multilayer Structure of OLED Device 76 2.1.2 Deposition of Organic Layer 77 2.1.3 Multiple-Layer Deposition from Solution 79 2.2 Thermally Crosslinkable Hole Transport Materials 83 2.2.1 Trifluorovinyl Ether-Based Hole Transport Materials 86 2.2.2 Styrene-Based Hole Transport Materials 97 2.3 Thermally Crosslinkable Hole Injection Materials 108 2.4 Thermally Crosslinkable Emitting Materials 122 2.5 Thermally Crosslinkable Electron Transport Materials 148 2.6 Conclusions 156 2.7 Experimental details 158 2.8 References 183 3 Structure-Function-Property Relationships in Conjugated Polyelectrolytes 191 3.1 Introduction 191 3.2 Charge Reversal in CPEs Electron Injection Layers: Cationic versus Anionic 195 3.3 Effect of Thermal Annealing on Polymer Light-Emitting Diodes Utilizing Cationic Conjugated Polyelectrolytes as Electron Injection Layers 201 3.4 Conclusions 208 3.5 Experimental details 209 3.6 References 210 Appendix A 1H and 13C NMR Spectra 215 Appendix B TGA and DSC Analyses of 4C6-T3 243 Appendix C X-Ray Crystallography Data 245
dc.language.iso	zh-TW
dc.title	旋環雙芴衍生物與濕式製程有機發光二極體材料之開發探究及其光電應用	zh_TW
dc.title	Development and Optoelectronic Applications of Spirobifluorene-Based Materials and Solution-Processable OLEDs Materials	en
dc.type	Thesis
dc.date.schoolyear	99-1
dc.description.degree	博士
dc.contributor.oralexamcommittee	洪文誼,蘇海清,林建村,周必泰
dc.subject.keyword	旋環雙芴,光電應用,濕式製程,有機發光二極體,聚合反應,	zh_TW
dc.subject.keyword	Spirobifluorene,Optoelectronic Applications,Solution-Process,Organic Light-Emitting Diodes,Polymerizable Reactions,	en
dc.relation.page	257
dc.rights.note	有償授權
dc.date.accepted	2010-10-12
dc.contributor.author-college	理學院	zh_TW
dc.contributor.author-dept	化學研究所	zh_TW
顯示於系所單位：	化學系

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