柯維丹

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姓名	Venkatesan(Govindan) 查詢紙本館藏	畢業系所	化學學系
論文名稱	柯維丹 (Venkatesan Govindan)
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摘要(中)	摘要本篇論文研究合成有機小分子應用在反式有機太陽能電池中作為 donor，在反式鈣鈦礦太陽能電池中作為電洞傳遞層材料，以及在一般式鈣鈦礦太陽能電池中作為電子傳遞層材料，並探討這些材料分子的物化性質、結構與材料性質的關係及材料組裝成元件後的光伏表現。第一部分研究以diketopyrrolopyrrole (DPP) 作為acceptor ， ethylenedioxythiophene (EDOT) 、triphenylamine (TPA) 、alkyl thiophene (AT) 作為donor ，利用direct alkylation 合成donor–donor–acceptor–donor– donor (D1–D2–A–D2–D1)類型的四個小分子(SM1, SM2, SM3, SM4)，以及利用Stille coupling合成acceptor–donor–acceptor (A–D–A)類型的兩個小分子 (SM5, SM6)，作為donor應用在反式有機太陽能電池中(PCBM為acceptor， ZnO為電子傳遞層，MoO3為電洞傳遞層)，因SM2有最低的HOMO能階，因此以SM2作為donor所組裝之元件有最高的VOC值，為0.82V。SM5和SM6 為結構異構物，但由於SM6和SM5相比有較好的溶解度和較低的HOMO能階，因此以SM6所組裝的元件有較好的光電轉換效率。第二部份研究合成雜環 spiro-typed 的分子做為電洞傳遞層材料，分別以spiro[fluorene-9,9’-xanthene] (SFX) 和spiro[fluorene-9,9’-thioxanthene] (SFT)為結構核心合成產率高成本低的SFX-TPAM、SFX-TPA、SFT-TPAM、 SFT-TPA等四個化合物。以這四個小分子作為電洞傳遞層(HTL)應用在元件中，元件架構為glass/ITO/HTL/CH3NH3PbI3/ C60/BCP/Ag。其中以SFXTPAM 作為HTL ，在不添加dopant 的條件下所組裝的元件和以spiro- OMeTAD作為電洞傳遞層所組裝的元件相比，有較好的光電轉換效率，為 10.23% 。第三部份的研究則包含三個以fullerene (C60及C70)為結構核心，bis(2- (2-((tert-butoxycarbonyl)amino)ethoxy)ethyl) malonate (4b)作為取代基，合成三個電子傳遞層修飾材料(C60-RT2、C60-RT6及C70-RT2)應用在一般式鈣鈦礦太陽能電池元件中。這三個材料對極性質子溶劑(甲醇、乙醇及水)有很好的溶解度，在一般式太陽能電池元件的製程中，混在TiO2漿料中使用，可以製作低溫TiO2。以TiO2+C60-RT2、TiO2+C60-RT6、TiO2+C70-RT6作為電子傳遞層所組裝之元件光電轉換效率分別為16.37%、18.03%及17.10%，較以TiO2作為電子傳遞層所組裝之元件效率(14.92%)來得高。
摘要(英)	Abstract This thesis is the work on the organic semiconductors for applications as electron donor (p-type) materials in organic solar cells (OSCs), hole transporting materials (HTMs) in inverted perovskite solar cells (p-i-n PSCs) and electron transporting materials (ETMs) in regular perovskite solar cells (n-i-p PSCs). The synthesis and physicochemical characterization of new materials (P-type, HTMs and ETMs) were reported. The structure-property relationship and the photovoltaic performance of the corresponding cells were investigated. The first part focuses on synthesis of four donor–donor–acceptor–donor– donor (D1–D2–A–D2–D1) type small molecules (SM1, SM2, SM3 and SM4), in which diketopyrrolopyrrole (DPP) was used as an acceptor (DPP) core and 3,4-ethylenedioxythiophene (EDOT), triphenylamine (TPA) or alkyl thiophene (AT) acted as a donor using direct arylation reaction. The inverted small molecule solar cell (using PCBM as an acceptor, and ZnO and MoO3 as the electron and hole transporters, respectively) based on SM2 has the highest value of Voc (0.82 V) due to SM2 having the lowest HOMO level. Two acceptor– donor–acceptor type (A–D–A) molecules (SM5 and SM6) were also synthesized by Stille coupling, in which DPP and EDOT were used as the acceptor and donor, respectively. SM5 and SM6 are structural isomers, however the inverted cell based on SM6 has a much higher PCE than that based on SM5, due to SM6 having better solubility and a lower HOMO energy level. The second part targets on four heterocyclic spiro-typed hole transporting materials (HTMs) carrying spiro[fluorene-9,9’-xanthene] (SFX) such as SFXTPAM and SFX-TPA or spiro[fluorene-9,9’-thioxanthene] (SFT) unit such as SFT-TPAM and SFT-TPA were synthesized through low cost facile route with high yields. The photovoltaic performance of the inverted PSCs based on these small molecular hole transporting materials with the device architecture of glass/ITO/HTM/CH3NH3PbI3/C60/BCP/Ag was studied. Inverted PSC based on dopant-free SFX-TPAM HTM achieves a power conversion efficiency of10.23% under the illumination of standard one Sun lighting, which is better than that (8.17%) of the cell based on dopant-free spiro-OMeTAD. The third part is the preparation and photovoltaic application of three fullerene based ETMs (C60-RT2, C60-RT6 and C70-RT2), in which fullerene (C60 and C70) as core unit and bis(2-(2-((tert-butoxycarbonyl)amino)ethoxy)ethyl) malonate (4b) was used as a substituent. All three fullerene exhibit very good solubility in polar protic solvents (such as methanol, ethanol and water), which is beneficial for making of low temperature processed ETMs for regular PSCs. The new fullerene derivatives were mixed with low temperature processed TiO2 to be used as ETMs in regular PSCs (FTO/ETMs/PSK/Spiro- OMeTAD/MoO3/Ag). Cells based on new ETMs have the PCE of 16.37% (TiO2+C60-RT2), 18.03% (TiO2+C60-RT6) and 17.10% (TiO2+C60-RT6), which is higher than that (14.92%) of the cell based on TiO2 ETL. The work of this thesis provides valuable guideline for designing charge transporting materials for photovoltaic application.
關鍵字(中)	★ Organic molecules ★ Hole transporting materials ★ Electronic transporting materials ★ Perovskite solar cells	關鍵字(英)
論文目次	Chinese Abstract i English Abstract iii Acknowledgements v Table of the contents .vi List of Figures .ix List of Tables.xii List of Schemes .xiii Explanation of symbols .xiv Chapter one: Introduction .1 1-1 Background 1 1-2 Photovoltaics 1 1-3 Organic solar cells (OSCs) .3 1-3-1 Device architecture .3 1-3-2 Working mechanism of OSCs.5 1-3-3 Photovoltaic characteristics.7 1-3-4 High performance donor small molecule .8 1-3-5 Acceptor materials 10 1-3-6 Diketopyrrolo[3,4-c]pyrrolopyrrole (DPP) based donor materials for OSCs. 11 1-4 Perovskite solar cells (PSCs)15 1-4-1 Device architecture and working mechanism of perovskite solar cells 16 1-4-2 Hole transporting materials for inverted PSCs19 1-4-3 Spiro-type hole transporting materials for inverted PSCs.19 1-4-4 Electron transporting materials .22 1-4-5 Fullerene based electron transporting materials for regular PSCs 22 1-5 Objective of this thesis34 Chapter Two: Facile synthesis of low band-gap DPP–EDOT containing small molecules for solar cell applications.38 2-1 Synthesis and characterizations of the small molecule SM1-SM6.38 2-2 Optical properties44 2-3 Electrochemical properties. 47 2-4 Small molecules in inverted heterojunction device .50 2-5 Conclusion 53 2-6 Experimental section 54 2-6-1 Synthesis of DPP based small molecule (SM1-SM6).54 2-6-2 Physicochemical studies69 2-6-3 Device fabrication and characterization70 Chapter Three: Heterocyclic spiro-type hole transporting materials for perovskite solar cell applications73 3-1 Synthesis and characterization of HTMs .73 3-2 Optical properties75 3-3 Electrochemical properties. 79 3-4 Photovoltaic performance.82 3-5 Conclusion 87 3-6 Experimental section 88 3-6-1 Synthesis of Spiro-type hole transporting materials (SFX-TPAM, SFX-TPA, SFT-TPAM and SFT-TPA).88 3-6-2 Physicochemical studies 96 3-6-3 Device fabrication and characterization 98 Chapter Four: Synthesis of fullerene based electron transporting materials for perovskite solar cell applications .100 4-1 Synthesis and characterization of Fullerene ETMs 100 4-2 Optical properties 105 4-3 Electrochemical properties .106 4-4 Photovoltaic performance.109 4-5 Conclusion 118 4-6 Experimental section 119 4-6-1 Synthesis of fullerene based electron transporting materials(C60-RT1, C60-RT2, C60-RT6 and C70-RT2).119 4-6-2 Physicochemical studies125 4-6-3 Device fabrication and characterization126 Chapter Five: Conclusions .128 Future Work .130 Reference 133
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指導教授	Chun-Guey Wu(Chun-Guey Wu)	審核日期	2019-4-16
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