推拉電子基β位取代BODIPY染料之合成與鑒定及其在染料敏化太陽能電池之應用

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王儷靜(Li-Jing Wang) 查詢紙本館藏

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化學學系

論文名稱

推拉電子基β位取代BODIPY染料之合成與鑒定及其在染料敏化太陽能電池之應用
(Synthesis and Characterization of Donor-Acceptor β-Substituted BODIPY and their Application for Dye Sensitized Solar Cells)

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摘要(中)

本論文主要合成BODIPY ( 4,4-difluoro-4-bora-3a,4a-diaza-s-indancene ) 衍生物，並以其做為染料敏化太陽能電池 ( dye- sensitized solar cells，DSSCs) 之光敏化劑。結構設計採Donor-π-Acceptor ( D-π-A ) 共軛系統，以BODIPY為π-conjugation system，在BODIPY之β位取代上分別與triphenylamine unit、(diphenylamino)thiophenyl unit、bis(4- methoxyphenyl)aminothiophenyl unit三種不同之推電子基鍵結以及拉電子基cyanoacrylic acid鍵結。另外亦有合成4,4-dihydroxyaryl- diaza-s-indacene之BODIPY衍生物，並且首次將此染料用於DSSCs上。以核磁共振光譜儀(NMR)、質譜儀鑑定化合物之結構；紫外-可見光光譜儀測量化合物之吸收光譜圖；由循環電位儀與光電子光譜儀測量與計算得知化合物之HOMO、LUMO能階；利用密度泛函理論計算出染料分子最穩定之結構以及含時密度泛函理論計算 HOMO 與 LUMO 能階分子軌域的分佈與其相對應之能階，以及模擬染料在激發態時電子躍遷之情形；並將染料應用於DSSCs探討其元件性能。其中染料PPB具有最高之能量轉換效率 ( Jsc = 5.73mA / cm2, Voc = 590 mV, FF = 0.70, η = 2.36 % )。經由實驗測量與理論計算發現將氟置換為氧時使用4-tert-butylcatechol 與pyrocatechol會使PCC、PPtC與PTtC之HOMO能階轉移，降低電子注入效率。
元件製程中的製程方法也會影響效率之高低，利用不同的方法將染料吸附上二氧化鈦、不同之溶劑將染料配製出不同濃度、不同的染料浸泡時間、不同之電解液等方式將元件最佳化。

摘要(英)

In this thesis, we synthesize the derivatives of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s- indancene), and apply these derivatives in dye sensitized solar cells. Use the conjugated system of Donor-π-Acceptor (D-π-A) on the design, and BODIPY play the role of π-conjugation system, bounding with differdent donor substituent such as triphenylamine unit, (diphenylamino)thiophenyl unit, bis(4-methoxyphenyl)aminothiophenyl unit, and acceptor substituent is cyanoacrylic acid on the β-substituent of BODIPY. On the other hand, we synthesize the derivatives of 4,4-dihydroxyaryl-diaza-s-indacene and for the first time apply these dye in dye sensitized solar cells. These compounds are characterized by 1H NMR, 13C NMR, mass spectrometry, their absorption spectrum were estimated by UV-visible spectrometer, and their energy level of HOMO and LUMO in solution and adsorb on TiO2 were estimated by cyclic voltammetry and low-energy photoelectron spectrometer, respectively, use density functional theory and time-dependent density functional theory to imitate the orbital and energy levels of HOMO and LUMO, and apply in DSSCs.
The highest power conversion efficiency in this thesis is PPB ( Jsc = 5.73mA / cm2, Voc = 590 mV, FF = 0.70, η = 2.36 % ). Through measure and TDDFT, displace the fluorine by 4-tert-butylcatechol and pyrocatechol will change the energy level of HOMO, and decrease the electron injection.
Fabricating solar cell devices is the crucial factor of power conversion efficient. By different way of adsorb, solvent, concentration, time and electrolyte will optimization the efficient.

關鍵字(中)

★ 染料敏化太陽能電池
★ BODIPY
★ D-π-A 共軛系統

關鍵字(英)

★ BODIPY
★ Donor-π-Acceptor conjugation system
★ Dye Sensitized Solar Cells

論文目次

摘要.......................................................i
Abstract..................................................ii
謝誌.....................................................iii
目錄......................................................iv
圖目錄....................................................vii
表目錄....................................................xii
第1章緒論...................................................1
1-1前言....................................................1
1-2太陽能電池的發展與種類......................................2
1-2-1矽基半導體型太陽能電池 ( Silicon type )...................4
1-2-2化合物半導體型太陽能電池 ( Compound type )................8
1-2-3有機材料型太陽能電池 (organic type).....................12
1-3太陽放射光譜圖...........................................19
1-4染料敏化太陽能電池的結構、工作原理與元件量測參數................22
1-4-1染料敏化太陽能電池結構...................................22
1-4-2染料敏化太陽能電池工作原理...............................27
1-4-3太陽能電池元件量測參數...................................31
1-5染料敏化劑..............................................36
1-5-1含金屬錯合物之有機染料 ( metal complex dye)..............39
1-5-2不含金屬有機染料 ( metal-free organic dye ).............44
1-6 BODIPY簡介............................................56
1-6-1 BODIPY在染料敏化太陽能電池上之應用.......................58
1-6-2 BODIPY在有機光伏電池上之應用............................72
1-7研究動機................................................77
第2章實驗..................................................79
2-1藥品...................................................79
2-2溶劑之前處理.............................................81
2-3實驗儀器................................................82
2-4合成流程 (scheme).......................................86
第3章結果與討論............................................109
3-1合成與討論.............................................109
3-2染料之光學測定..........................................110
3-2-1紫外-可見光吸收光譜及莫耳消光係數.........................111
3-2-2染料在二氧化鈦上之吸收光譜與吸附量........................126
3-3染料之電位測定..........................................131
3-3-1染料之電化學量測.......................................131
3-3-2 染料之低能量光電子光譜儀 ( Low-Energy Photoelecton Spectrometer )量測................137
3-4 DFT理論計算染料之HOMO / LUMO 能階.......................143
3-5元件與測量.............................................159
3-5-1浸泡時間與共吸附劑之元件最佳化...........................159
3-5-2浸泡溶劑之最佳化.......................................162
3-5-3 最佳化之元件與測量....................................163
第4章結論.................................................173
參考文獻..................................................174
附圖.....................................................184

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指導教授

陳錦地、吳春桂
(Chin-Ti Chen、Chun-Guey Wu)

審核日期

2012-8-8

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