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非摻雜型芳香取代呋喃螢光分子的合成及螢光特性 = Synthesis a...

國立高雄大學應用化學系碩士班

非摻雜型芳香取代呋喃螢光分子的合成及螢光特性 = Synthesis and Characterization of Non-doped Aryl-substituted Furan Fluorophores

紀錄類型:	書目-語言資料,印刷品 : 單行本
並列題名:	Synthesis and Characterization of Non-doped Aryl-substituted Furan Fluorophores
作者:	洪羽婷,
其他團體作者:	國立高雄大學
出版地:	[高雄市]
出版者:	撰者;
出版年:	2011[民100]
面頁冊數:	220面圖，表格 : 30公分;
標題:	呋喃螢光分子
標題:	furan fluorophores
電子資源:	http://handle.ncl.edu.tw/11296/ndltd/75095101126329703911
附註:	參考書目：面128-131
摘要註:	本研究期望合成有機發光二極體的藍色螢光材料，且在非摻雜的條件下，還是可以有高的螢光亮度。選擇呋喃分子為主體，在周圍導入具立體結構的取代基，穩定其熱性質，且導入的取代基具發光效果，並誘發其發光特性。在分子的設計上則分成兩大類，一為呋喃主體分子直接接上發光團官能基，這部分的分子可藉由環化反應得到以呋喃為主體的螢光分子；二為呋喃主體分子與發光團官能基中以一苯環連接，這部分的螢光分子可利用Suzuki-Miyamura耦合反應導入不同的發光團官能基。過程中，將利用核磁共振光譜(NMR)、質譜儀(Mass)等光譜儀器鑑定分子的結構。分子設計上藉由改變官能基的立體結構及分子的共振長度，用以討論分子結構的改變對螢光分子的電化學及光物理特性的影響。將目標分子以紫外光-可見光光譜儀、螢光光譜儀及磷光光譜儀測量其光物理性質；並利用示差掃描卡計(DSC)和熱分析儀(TGA)了解分子的熱性質；且以循環電位儀(CV)量測氧化電位並藉由計算推斷出分子的HOMO/LUMO值及能隙(Energy Gap)。研究結果顯示，導入的發色團官能基，共振短，可以使分子的光色坐落在藍色波長上(422-465 nm)；且當導入立體結構大的官能基或增加分子的分子量時，因削減分子的平面性，所以可有效的提升螢光效率；利用呋喃分子為中心分子時，可以增加分子的HOMO值(4.97-5.43 eV)，並藉由分子的共振長度來調制LUMO值(2.1-2.51 eV)，進而控制能隙(2.87-2.97 eV)。結果顯示，分子的能隙夠大時，是有潛力成為磷光發光體(Host)。而結構改變對分子特性的影響，發現，當導入主體分子中的官能基具有較大的立體結構時，可以有效的提升分子的玻璃轉移溫度（Tg），尤其當導入spirobifluorene的官能基時，Tg溫度更可高達197 ℃。證實，立障大的官能基的確可以有效的穩定分子的熱性質。結果顯示，目標分子皆為發藍色光的螢光分子，並且在無摻雜的條件下也可以有好的螢光特性；而結構的設計下也使其成為熱穩定性高的材料分子。但若要成為藍色光的磷光主發光體材料，則需將HOMO/LUMO能階向上位移，其更接近藍色磷光主發光體的特質。不過從磷光特性看來，還是有潛力可作為不同色光的磷光主發光體。 This research expected to synthesize the blue fluorescence material of organic light-emitting diodes, and they still possessed high quantum efficiency in non-doped system. We used furan as cores, and fluorescence properties of these furan fluorophores were induced and stabilized the thermal properties by manipulating the surrounding aryl groups of fluorescence properties. There were two parts of molecular design: one was the furan fluorophores connect the chromophores directly, these furan fluorophores were synthesized by cyclization reaction; the other one was the furan fluorophores connect the chromophores by a aromatic compound(a phenyl group), these furan fluorophores were synthesized by Suzuki-Miyaura cross coupling reaction to insert the different chromophores. And the structures of fluorescent molecules were identified by NMR and Mass spectra. By regulating the structure of functional groups and the length of molecular resonance investigated the electrochemical and photophysical properties. Photophysical properties of the furan fluorophores were characterized from UV-visible and fluorescence spectra; thermal properties of the furan fluorophores were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), and the HOMO/LUMO and energy gap of furan fluorophores were measured and calculated by cyclic voltammetry (CV). In our research, when the chromophores with short resonances were inserted, they exhibited blue emissions; and when the chromophores with bulky functional groups or enhanced the weight, it reduced the molecular plane, so it can elevate the fluorescence quantum yields; we use the furan as cores, it can increase the HOMO level (4.97-5.43 eV). By tuning the length of molecular resonance to control the energy gap (2.87-2.97 eV). The results revealed that these furan fluorophores with higher energy gap had potential for phosphorescent hosts. The influence of molecular characteristic by the changing the structure, we found that furan fluorophores with rigid structures can effectively raise the glass transition temperature of the molecular, especially when the functional groups is spirobifluorene, the glass transition temperature can be as high 197 oC. It can verify that the bulky structure can stabilize the thermal properties effectively. These results indicated that these fluorophores had blue emission, good fluorescent characteristics in non-doped system and excellent thermal stability. But if these fluorophores went to be the material of blue phosphorescent hosts, the HOMO/LUMO level had to shift upward to closer the characteristics of blue phosphorescent hosts. However, it still had potential for the phosphorescent hosts of different colors by phosphorescent characteristics.

非摻雜型芳香取代呋喃螢光分子的合成及螢光特性 = Synthesis and Characterization of Non-doped Aryl-substituted Furan Fluorophores
洪, 羽婷

非摻雜型芳香取代呋喃螢光分子的合成及螢光特性 = Synthesis and Characterization of Non-doped Aryl-substituted Furan Fluorophores / 洪羽婷撰 - [高雄市] : 撰者, 2011[民100]. - 220面 ; 圖，表格 ; 30公分.
參考書目：面128-131.
呋喃螢光分子furan fluorophores

非摻雜型芳香取代呋喃螢光分子的合成及螢光特性 = Synthesis and Characterization of Non-doped Aryl-substituted Furan Fluorophores
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330 $a 本研究期望合成有機發光二極體的藍色螢光材料，且在非摻雜的條件下，還是可以有高的螢光亮度。選擇呋喃分子為主體，在周圍導入具立體結構的取代基，穩定其熱性質，且導入的取代基具發光效果，並誘發其發光特性。在分子的設計上則分成兩大類，一為呋喃主體分子直接接上發光團官能基，這部分的分子可藉由環化反應得到以呋喃為主體的螢光分子；二為呋喃主體分子與發光團官能基中以一苯環連接，這部分的螢光分子可利用Suzuki-Miyamura耦合反應導入不同的發光團官能基。過程中，將利用核磁共振光譜(NMR)、質譜儀(Mass)等光譜儀器鑑定分子的結構。分子設計上藉由改變官能基的立體結構及分子的共振長度，用以討論分子結構的改變對螢光分子的電化學及光物理特性的影響。將目標分子以紫外光-可見光光譜儀、螢光光譜儀及磷光光譜儀測量其光物理性質；並利用示差掃描卡計(DSC)和熱分析儀(TGA)了解分子的熱性質；且以循環電位儀(CV)量測氧化電位並藉由計算推斷出分子的HOMO/LUMO值及能隙(Energy Gap)。研究結果顯示，導入的發色團官能基，共振短，可以使分子的光色坐落在藍色波長上(422-465 nm)；且當導入立體結構大的官能基或增加分子的分子量時，因削減分子的平面性，所以可有效的提升螢光效率；利用呋喃分子為中心分子時，可以增加分子的HOMO值(4.97-5.43 eV)，並藉由分子的共振長度來調制LUMO值(2.1-2.51 eV)，進而控制能隙(2.87-2.97 eV)。結果顯示，分子的能隙夠大時，是有潛力成為磷光發光體(Host)。而結構改變對分子特性的影響，發現，當導入主體分子中的官能基具有較大的立體結構時，可以有效的提升分子的玻璃轉移溫度（Tg），尤其當導入spirobifluorene的官能基時，Tg溫度更可高達197 ℃。證實，立障大的官能基的確可以有效的穩定分子的熱性質。結果顯示，目標分子皆為發藍色光的螢光分子，並且在無摻雜的條件下也可以有好的螢光特性；而結構的設計下也使其成為熱穩定性高的材料分子。但若要成為藍色光的磷光主發光體材料，則需將HOMO/LUMO能階向上位移，其更接近藍色磷光主發光體的特質。不過從磷光特性看來，還是有潛力可作為不同色光的磷光主發光體。 This research expected to synthesize the blue fluorescence material of organic light-emitting diodes, and they still possessed high quantum efficiency in non-doped system. We used furan as cores, and fluorescence properties of these furan fluorophores were induced and stabilized the thermal properties by manipulating the surrounding aryl groups of fluorescence properties. There were two parts of molecular design: one was the furan fluorophores connect the chromophores directly, these furan fluorophores were synthesized by cyclization reaction; the other one was the furan fluorophores connect the chromophores by a aromatic compound(a phenyl group), these furan fluorophores were synthesized by Suzuki-Miyaura cross coupling reaction to insert the different chromophores. And the structures of fluorescent molecules were identified by NMR and Mass spectra. By regulating the structure of functional groups and the length of molecular resonance investigated the electrochemical and photophysical properties. Photophysical properties of the furan fluorophores were characterized from UV-visible and fluorescence spectra; thermal properties of the furan fluorophores were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), and the HOMO/LUMO and energy gap of furan fluorophores were measured and calculated by cyclic voltammetry (CV). In our research, when the chromophores with short resonances were inserted, they exhibited blue emissions; and when the chromophores with bulky functional groups or enhanced the weight, it reduced the molecular plane, so it can elevate the fluorescence quantum yields; we use the furan as cores, it can increase the HOMO level (4.97-5.43 eV). By tuning the length of molecular resonance to control the energy gap (2.87-2.97 eV). The results revealed that these furan fluorophores with higher energy gap had potential for phosphorescent hosts. The influence of molecular characteristic by the changing the structure, we found that furan fluorophores with rigid structures can effectively raise the glass transition temperature of the molecular, especially when the functional groups is spirobifluorene, the glass transition temperature can be as high 197 oC. It can verify that the bulky structure can stabilize the thermal properties effectively. These results indicated that these fluorophores had blue emission, good fluorescent characteristics in non-doped system and excellent thermal stability. But if these fluorophores went to be the material of blue phosphorescent hosts, the HOMO/LUMO level had to shift upward to closer the characteristics of blue phosphorescent hosts. However, it still had potential for the phosphorescent hosts of different colors by phosphorescent characteristics.
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