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系統識別號 U0002-2607201500254600
中文論文名稱 小分子有機光伏打電池材料偶極性茚並茚衍生物的合成與性質檢測
英文論文名稱 The synthesis and investigation of novel dipolar dihydroindenoindene derivatives for small molecular organic photovoltaic solar cell
校院名稱 淡江大學
系所名稱(中) 化學學系碩士班
系所名稱(英) Department of Chemistry
學年度 103
學期 2
出版年 104
研究生中文姓名 蕭凱倫
研究生英文姓名 Kai-Lun Hsiao
學號 699180096
學位類別 碩士
語文別 中文
口試日期 2015-06-24
論文頁數 83頁
口試委員 指導教授-謝仁傑
委員-謝仁傑
委員-陳志欣
委員-莊士卿
中文關鍵字 太陽能電池  有機光伏打電池  茚並茚 
英文關鍵字 Solar cell  OPV  TDI 
學科別分類 學科別自然科學化學
中文摘要 有機光伏打電池是利用化學合成的有機材料塗佈於元件上,厚度只需幾百奈米即可,藉由調整其能隙,使太陽能電池能對太陽光有更廣的吸收範圍,期待它有更高的吸光係數,以及更好的光電轉換效率。
  此論文主要是合成出有機光伏打電池之主動層,在製程上欲以 5,5,10,10-tetraphenyl-5,10-dihydro-indeno[2,1-a]-indene ( TDI ) 作為基本模板,組合 arylamine (電子供體片段, D )和 aryl-2-methylene-malononitrile (電子受體片段, A ) 形成 D-TDI-A 的吸光分子,先以理論計算推算適合的電子供體片段和電子受體片段,再依據理論計算結果,合成光學特性較佳的化合物,經由光學儀器分析,比較和理論計算結果的誤差,得到Da-TDI-Aa 為吸光範圍最寬的化合物。
英文摘要 Organic photovoltaic cells (OPV) utilizes organic material- which is chemically synthesized- to coat on the component: only a few hundred nanometers is required. By adjusting its energy gap, the solar cell could have a broader absorption range to the sunlight, which hypothetically would to achieve a higher absorption coefficient, and therefore better photoelectric conversion efficiency.
This thesis discusses the procedure for synthesizing the active layer of OPV. In the procedure, the 5,5,10,10-tetraphenyl-5,10-dihydro-indeno [2,1-a] -indene (TDI) is used as the basic template. The TDI is then combine with arylamine (electron donor fragment, D) and aryl-2-methyl-enemalononitrile (electron acceptor fragment, A) to form a D-TDI-A light-absorbing molecule. Calculation is then performed to determine the theoretically suitable electron donor fragments and electron acceptor fragments. Then based on the calculation result to synthesize the compound, which has better optical properties. The theoretical results and the experimental results are then compared with each other through analysis by optical instruments. The analysis result suggested that the Da-TDI-Aa is the compounds which has the widest range of absorbance.
論文目次 第一章 緒論
1.1前言 1
1.2有機太陽能電池 3
1.3 有機光伏打電池 ( OPV ) 元件、裝置 5
1.3.1有機光伏打電池原理 5
1.3.2吸光活性層(Active Layer) 8
1.3.3界面層(Interfacial Layer) 10
1.3.4 PEDOT:PSS 10
1.3.5銦錫氧化物(ITO)層 11
1.3.6 電極 11
1.4 小型有機光伏打電池元件 ( SM-OPV devices ) 11
第二章 偶極茚並茚衍生物的合成與性質測試
2.1文獻探討 13
2.2 分子設計 15
2.3 分子合成及光學分析 18
2.4討論 23
第三章 合成實驗
3.1 實驗儀器 25
3.2 合成步驟 27
3.3 溶劑純化除水、除氧 42
3.3.1 除水 42
3.3.2 除氧 43
3.4 實驗藥品 44
參考文獻 46
附錄
一、 核磁共振光譜圖 54
1化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 54
2化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 55
4化合物之1H NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 56
4化合物之13C NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 57
5化合物之1H NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 58
5化合物之13C NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 59
8化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 60
9化合物之1H NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 61
9化合物之13C NMR ( 600MHz, CDCl3 ) 核磁共振光譜圖 62
11a化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 63
11b化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 64
12a化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 65
12b化合物之1H NMR ( 300MHz, CDCl3 ) 核磁共振光譜圖 66
二、MS 圖譜 67
8化合物之MS質譜 67
8化合物之HR-MS高解析質譜 68
9化合物之MS質譜 69
9化合物之HR-MS高解析質譜 70
11a化合物之MS質譜 71
11a化合物之HR-MS高解析質譜 72
11b化合物之MS質譜 73
11b化合物之HR-MS高解析質譜 74
12a化合物之MS質譜 75
12a化合物之HR-MS高解析質譜 76
12b化合物之MS質譜 77
12b化合物之HR-MS高解析質譜 78
三、UV-VIS 光譜 79
8化合物之UV-VIS光譜 79
12a化合物之UV-VIS光譜 80
12b化合物之UV-VIS光譜 81
四、CV 光譜 82
12a化合物之CV光譜 82
12b化合物之CV光譜 83
圖目錄
圖1-1、太陽能電池的分類 4
圖1-2、釕類錯合物(a) N719 (b) BlackDye 5
圖1-3、有機光伏打電池元件電子激發 6
圖1-4、有機光伏打電池元件電子、電洞形成 6
圖1-5、有機光伏打電池元件電子、電洞分離 7
圖1-6、電子、電洞分別往不同方向傳輸 7
圖1-7、有機光伏打電池元件裝置結構 8
圖 1-8、PCBM的分子結構 9
圖1-9、吸光活性層(Active Layer)混合方式 : (a) Bilayer (b) Bulk Heterojunction 10
圖1-10、PEDOT:PSS的分子結構 11
圖1-11、CuPc -酞菁分子類 12
圖2-1、吳忠幟教授所發表的染料敏化太陽能電池元系件之分子結構 13
圖2-2、N719 之分子結構 14
圖2-3、 Da-TDI-Aa、Db-TDI-Ab、Db-TDI-Ad UV_Vis 光譜疊圖 21
流程圖目錄
流程圖2-1、TDI分子的合成策略 18
流程圖2-2、分子Da-TDI-Aa 的合成策略 19
流程圖2-3、分子Db-TDI-Ab、Db-TDI-Ad 的合成策略 20
流程圖3-1、1化合物之合成 27
流程圖3-2、2化合物之合成 28
流程圖3-3、3化合物之合成 29
流程圖3-4、4化合物之合成 30
流程圖3-5、5化合物之合成 31
流程圖3-6、6化合物之合成 32
流程圖3-7、7化合物之合成 33
流程圖3-8、8化合物之合成 34
流程圖3-9、9化合物之合成 35
流程圖3-10、10化合物之合成 36
流程圖3-11、11化合物之合成 37
流程圖3-12、12化合物之合成 38
流程圖3-13、13化合物之合成 39
流程圖3-14、14化合物之合成 40
流程圖3-15、15化合物之合成 41
表目錄
表2-1、D-TDI-A 組合表 15~16
表2-2、最大吸收波長 (λMAX ) 及200~700 nm 吸收光範圍積分 22
表2-3、D-TDI-A元件在二氯甲烷的吸收波長以方法TD-BHandHLYP/6-31G(d)計算 23
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