用於高分子太陽能電池中含有玉紅省之非富勒烯電子接受材料之合成及性質探討

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研究生：	葉日景 Jih-Ching Yeh
論文名稱：	用於高分子太陽能電池中含有玉紅省之非富勒烯電子接受材料之合成及性質探討 Synthesis and Characterization of Diindeno[1,2-g:1’,2’-s]rubicene-based Non-fullerene Electron Acceptor for Polymer Solar Cells
指導教授：	陳錦地
口試委員:
學位類別：	碩士 Master
系所名稱：	理學院 - 化學學系 Department of Chemistry
論文出版年：	2019
畢業學年度：	107
語文別：	中文
論文頁數：	155
中文關鍵詞：	太陽能、非富勒烯、電子接受材料
相關次數：	點閱：8 下載：0
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本論文中主要合成DIR (Diindeno[1,2-g:1’,2’-s]rubicene)衍生物，作為高分子太陽能電池中的電子受體，在設計中使用了具有ICT現象之A-D-A結構，以DIR做為D的部分並有直鏈(octyl)及分岔鏈(2-Ethyl-1-hexyl)兩種碳鏈之DIR核心，在A的部分則使用三種拉電子基團5,5-Dimethyl-1,3-cyclohexanedione (DCD)、2-(3-Oxo-inden-1-ylidene)malononitrile (IC)、2-(5,6-Difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC2Cl)來搭配，合成出共計6種由DIR作為核心之非富勒烯電子受體(NFA)，分別為OcDCD、OcIC、OcIC2Cl、EHDCD、EHIC、EHIC2Cl。在本篇論文中對此6種非富勒烯電子受體進行一系列量測，包含熱性質、吸收光譜、能階的量測、理論計算出之電子雲分佈圖，來評估取代高分子太陽能電池中PCBM電子受體材料。
藉由A-D-A結構使ICT現象增強使吸收波長產生紅移，原先未接上拉電子基團之DIR主要吸收落在300~400 nm(近紫外光吸收峰)，在接上了拉電子基團後使主要吸收轉換至500~650 nm(可見光吸收峰)，同時由於PCBM之主要吸收皆落在400 nm以下，可以看出本論文設計之NFA有較好太陽光吸收。同時在引入強拉電子基團時會使LUMO能階有顯著的下降，使LUMO能階下降至接近PCBM的，以達到更好拆解高分子的激子。

In this work, DIR (Diindeno[1,2-g:1',2'-s]rubicene) derivatives are synthesized as electron acceptors in polymer solar cells. In this design, an A-D-A structure with ICT phenomenon is used. The system uses DIR as part of D and has two DIR cores, which are linear (octyl) and branched (2-Ethyl-1-hexyl) carbon chains. In the part of A, three kinds of electron withdrawing groups, 5,5-Dimethyl-1,3-cyclohexanedione (DCD), 2-(3-Oxo-inden-1-ylidene)malononitrile (IC), 2-(5,6-Difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (IC2Cl). By substitution, a total of six non-fullerene electron acceptors with DIR as the core were synthesized, which were OcDCD, OcIC, OcIC2Cl, EHDCD, EHIC, and EHIC2Cl. We performed a series of measurements on these six non-fullerene electron acceptors (NFA). These include thermal properties, absorption spectra, energy level measurements, theoretical calculation of energy level electronic cloud distribution. Evaluation of PCBM electron acceptor materials in substituted polymer solar cells from the above results.
The absorption of the ICT phenomenon is enhanced by the A-D-A structure, and the absorption wavelength is red-shifted. The original DIR structure is mainly absorbed at 300-400 nm (near ultraviolet absorption peak), and the main absorption is red-shifted to 500-650 nm (visible light absorption peak) after the electron-withdrawing group is attached. At the same time, when the strong electron withdrawing group is introduced, the LUMO energy level is significantly decreased, and the LUMO energy level is lowered to be close to the PCBM, so as to achieve a better disassembly of the polymer exciton.

一、緒論    1
1-1 前言    1
1-2 太陽光光譜    1
1-3太陽能電池元件量測參數    2
1-4有機光伏太陽能電池    4
1-5 電子供體 (Donor)    8
1-6 電子受體 (Acceptor)    10
1-6-1 富勒烯電子受體 (Fullerene acceptor)    10
1-6-2 非富勒烯小分子電子受體 (Non-fullerene acceptor, NFA)    11
1-6-2-1 苝二亞醯胺 (perylene diimide, PDI)    12
1-6-2-2 吡咯並吡咯二酮 (Diketopyrrolopyrrole, DPP)    13
1-6-2-3 芴 (Fluorene)    14
1-6-2-4 二環戊烷並苯二噻吩 (Indacenodithiophene, IDT)    15
1-7 NFA用在有機太陽能電池近期的發展及討論    16
1-8 分子內電荷轉移效應 (Intramolecular charge transfer, ICT)    20
1-9 玉紅省(Rubicene)結構之討論    24
1-10 研究動機    26
二、實驗內容    30
2-1 使用藥品及溶劑    30
2-2 儀器設備    32
2-3 實驗流程    35
2-3-1 DIR核心的合成路徑    35
2-3-1 親電子基團之合成合成路徑    36
2-3-1 有機小分子電子受體之合成    37
2-4 合成步驟    38
三、結果與討論    54
3-1 合成討論    54
3-2理論計算    57
3-3熱性質    70
3-3-1 TGA測量    70
3-3-2 DSC量測    71
3-4 光學性質    73
3-4-1 DIR系列化合物之溶液及薄膜吸收光譜    73
3-4-2 DIR系列化合物之溶劑色位移之吸收光譜    74
3-5 低能量光電子公函數量測    77
3-6 電化學性質    78
3-7 P4TD系列高分子電子供體材料性質    82
3-7-1 UV-vis光譜測量    83
3-7-2 電化學性質    84
3-8 有機高分子太陽能電池元件預測    86
四、結論    90
五、參考資料    91
附錄    94

                                

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