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研究生:余井元
研究生(外文):Ching-Yuan Yu
論文名稱:新穎電致磷光材料之合成及光物理性質探討
論文名稱(外文):The Studies on Synthesis and Photophysical Properties of Novel Electrophosphorescent Materials
指導教授:歐陽文忠歐陽文忠引用關係
指導教授(外文):W.-C. Ou-Yang
學位類別:碩士
校院名稱:國立高雄應用科技大學
系所名稱:化學工程與材料工程系
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:2009
畢業學年度:97
語文別:中文
論文頁數:197
中文關鍵詞:有機發光二極體銥金屬錯合物鈴木偶合法
外文關鍵詞:Ir-complexPHPLEDSuzuki Cross Coupling Reaction
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本研究以Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hexyl-3,7-pheno-
thiazine)、Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hexyl-3,7-phenothiazine-5-oxide)、Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hexyl-3,7-phenothiazine-5,5-dioxide)、Poly(9,9-dioctylfluorene-2,7-diyl-alt-9-hexyl-3,6-carbazole)、Poly(9,9-dioctylfluorene-alt-2,5-pyridine)五種共軛聚合物為host材料,磷光體Ir-complex為guest材料,利用Suzuki Cross coupling方法,將共軛聚合物與不同比例的Ir-complex化學鍵結成磷光共聚物材料,可作為在電致磷光發光二極體Electrophosphorescent light-emitting diodes (PHPLED)的應用。
由實驗結果顯示,電致磷光材料皆在300 ℃才有明顯的裂解(熱裂解溫度Td :ca. 300 ℃),故皆具有良好之熱穩定性。由偏光顯微鏡圖像分析,固體膜呈現無定型均勻的薄膜。UV-vis吸收主要皆由共軛高分子吸收能量。由PL圖譜可知電致磷光材料隨著Ir complex含量增加其特性峰有紅位移的現象,在1 w/v%溶液狀態下磷光放射波長ca. 560 nm,固體膜磷光放射波長ca. 625 nm。電化學性質方面,電子傳遞基團Ir-complex導入量增加,聚合物LUMO能階明顯下降,改善了電子注入的能力。元件性質,電致磷光材料隨Ir-complex含量增加,輝度值降低,由EL圖譜可知磷光放射波長ca. 640 nm,CIE色座標往紅色飽和光區移動,兩者趨勢相吻合。
In this study, we successfully synthesized the novel electrophosphoresc-
ent materials such as PFPTZ、PFPTZ-S、PFPTZ-SS、PFCZ、PFPY as the host, and copolymerized with various ratios of Ir-complex as the guest by Suzuki Cross coupling reaction.
The results showed that these electrophosphorescent materials exhibited good thermal stability with 5% weight loss temperatures which were above 3000C in nitrogen atmosphere. The amorphous solid films of electrophosphorescent materials were clear seen from the polarization microscopy images. The UV-vis absorption of the electrophosphorescent materials almost absorbed by the fluorescent conjugate polymer (the host). As the amount of Ir-complex was increased, the characteristic peaks of the photoluminescence spectra of these electrophosphorescent materials had exhibited further red-shift. The phosphorescent emission peaks of electrophosphorescent materials were around 560 nm in 1 w/v% solution and the phosphorescent emission peaks were around 625 nm in the solid film. The LUMO level of these electrophosphorescent materials were lowered due to the introduction of Ir-complex units. The maximum luminance of devices were lowered with increasing amount of Ir- complex. The phosphorescent emission peaks of the electrophosphorescent materials were around 640 nm and the coordinated points of C.I.E. were shifting saturated red region, which were consistent with PL spectra.
目錄
中文摘要…………………………………………………………… I

Abstract……………………………………………………………... III

致謝…………………………………………………………………. IV

目錄………………………………………………………………… V

表目錄……………………………………………………………… X

圖目錄……………………………………………………………… XI

第一章 緒論……………………………………………………… 1
1.1、前言………………………………………………… 1
1.2、理論背景…………………………………………… 2
1.3、文獻回顧…………………………………………… 8
1.4、研究動機…………………………………………… 15
第二章 實驗內容………………………………………………… 16
2.1、實驗藥品…………………………………………… 16
2.2、材料合成…………………………………………… 19
2.2.1、9,9-dioctylfluorene……………………………… 19
2.2.2、2,7-Dibromo-9,9-dioctylfluorene………………… 20
2.2.3、9,9-dioctylfluorene-2,7-Diboronic acid………… 20
2.2.4、10-n-Hexylphenothiazine………………………… 22
2.2.5、3,7-Dibromo-10-n-hexylphenothiazine………… 22
2.2.6、3,7-Dibromo-10-n-hexylphenothiazine-5-oxide… 23
2.2.7、3,7-Dibromo-10-n-hexylphenothiazine-5,5
-dioxide…………………………………………...
23
2.2.8、9-hexylcarbazole………………………………… 24
2.2.9、3,6-Dibromo-9-hexylcarbazole…………………… 25
2.2.10、Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hex
yl-3,7-phenothiazine)…………………………
25
2.2.11、Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hex
yl-3,7-phenothiazine-5-oxide)…………………
26
2.2.12、Poly(9,9-dioctylfluorene-2,7-diyl-alt-10-n-hex
yl-3,7-phenothiazine-5,5-dioxide)……………
28
2.2.13、Poly(9,9-dioctylfluorene-2,7-diyl-alt-9-hexyl-
3,6-carbazole)…………………………………
29
2.2.14、Poly(9,9-dioctylfluorene-alt-2,5-pyridine)… 31
2.2.15、1,4-dibromonaphthalene………………………… 32
2.2.16、1-bromonaphthalene-4-boronic acid…………… 32
2.2.17、5-bromo-2-(4-bromonaphthalen-1-yl)pyridine… 33
2.2.18、phenylboronic acid……………………………… 34
2.2.19、2-phenylpyridine………………………………... 34
2.2.20、μ-chloro-bridged dimmer……………………… 35
2.2.21、Ir-complex……………………………………… 35
2.3、合成電致磷光材料………………………………… 37
2.4、實驗儀器…………………………………………… 39
2.5、附錄………………………………………………… 41
第三章 材料化學結構鑑定……………………………………… 55
3.1、實驗方法…………………………………………… 55
3.2、傅利葉轉換紅外線光譜儀(FTIR)………………… 56
3.3、核磁共振光譜儀(1H-NMR)……………………… 56
3.4、元素分析儀(EA)………………………………… 57
第四章 材料物理性質探討……………………………… 73
4.1、實驗方法…………………………………………… 73
4.2、凝膠滲透儀分析…………………………………… 74
4.3、熱穩定分析………………………………………… 86
4.4、偏光顯微鏡分析…………………………………… 91
4.5、結論………………………………………………… 101
第五章 材料光物理性質探討…………………………………… 102
5.1、紫外光-可見光吸收光譜………………………….. 102
5.2、螢光光譜儀(PL)……………………………… 106
5.2.1、THF溶液螢光光譜分析………………………… 108
5.2.2、Toluene溶液螢光光譜分析…………………….. 120
5.2.3、固態膜螢光光譜分析…………………………… 128
5.2.4、摻合系統螢光光譜分析………………………… 135
5.3、CIE 色座標………………………………………… 144
第六章 電化學與元件特性……………………………………… 149
6.1、循環伏安實驗……………………………………… 149
6.1.2、材料電化學特性………………………………… 152
6.1.3、電化學性質結論………………………………… 170
6.2、元件製作…………………………………………… 171
6.2.1、ITO玻璃蝕刻…………………………………… 171
6.2.2、清洗ITO玻璃…………………………………… 171
6.2.3、元件建構………………………………………… 172
6.2.4、元件量測………………………………………… 173
6.2.5、元件I-V-L特性………………………………… 174
6.2.6、EL分析…………………………………………... 184
6.2.7、CIE座標分析…………………………………… 187
6.2.8、元件分析結論…………………………………… 190
第七章 結論……………………………………………………… 192
參考文獻………………………………………………………......... 194
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