共軛添加劑對有機光伏太陽能電池之熱穩定性探討

趙英捷

doi:10.6342/NTU201704510

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共轭添加剂对有机光伏太阳能电池之热稳定性探讨

Study of Conjugated Additives for Thermally Stable Organic Photovoltaics

赵英捷 , 博士　　导师：郑如忠　　

繁体中文 DOI： 10.6342/NTU201704510

有机光伏电池；聚合物太阳能电池；分子间作用力；交联剂；热稳定性； EMD衍生物；高穿透度； organic photovoltaics ； polymer solar cells ； intermolecular interaction ； crosslinker ； thermal stability ； Emeraldicene derivatives ； high transparency

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摘要 │ 参考文献 (161) │ 国际计量

摘要〈TOP〉

Part Ⅰ.具有末端官能基的共轭小分子添加剂
在这项工作中，我们准备了四个星形共轭小分子，三苯胺二噻吩（TBT）衍生物，即TBT-H，TBT-Br，TBT-OH和TBT-N3分别具有不同端基，氢化物，溴化物，羟基和叠氮化物末端官能基。这些TBT衍生物应用於有机光伏电池的活性层的添加剂，以研究分子间相互作用（TBT-H，TBT-OH）或交联（TBT-N3，TBT-Br）对有机光伏的长期热稳定性的影响设备。从混合膜形态，光电子和器件性能的分析，我们观察到在加热添加剂TBT-N3和TBT-Br的设备中在150°C的加速加热测试期间的热稳定性的显着增强。这两种添加剂作为交联剂，并构造有效阻止热促进的富勒烯的聚集，从而导致高度稳定的形态。当与相应的正常器件比较时，P3HT导入TBT-N3的元件表现出更大的稳定性。在150°C下144小时之後，光电转换效率（PCE）仍能保持高达2.5％。由於这种增强，制造了基於非晶低带隙聚合物PTB7添加了TBT-N3。我们观察到器件稳定性的显着改进，在150 °C加热的加速实验下，保持其初始PCE的约60％（从5.0％至3.3％）。相反，相应的正常器件的PCE衰减到其初始值的0.01％。

Part II. 可见光高穿透的共轭高分子
在本研究中，我们合成了两种EMD高分子衍生物、分别为PBTEMD和PFEMD。这些EMD衍生物聚合物用作在聚合物太阳能电池的活性层中当作给体与PC71BM共混之共混膜，以研究它们的光电性能和其相关的光伏性能。据我们所知，这是第一个使用EMD衍生物应用於有机太阳能电池的研究。我们比较了其分子结构，相关的吸收、能阶、热性能和有机太阳能电池的热稳定性。因为PEEMD的主吸收处於近红外光谱（600nm至800nm）的范围内。PFEMD的共混膜膜厚为95nm时其透明度高於80％，并且所构造的器件在AM 1.5G（100mW cm -2）下显示最高2.5％的光电功率转换效率。除此之外，我们观察到交联型添加剂（TBT-N3）的元件其热稳定性有显着提高。在150°C加热的加速实验下，仍能保持约60％的初始PCE。相反的其相对应的正常器件其PCE衰减到其初始值的0.01％，己微乎其微。
 
Part III. 添加多功能添加剂对有机光伏增强器件性能和稳定性的影响
在本研究中，我们开发了以二酮吡咯并吡咯（DPP）为核心的新型添加剂具有末端叠氮官能基团的烷基链以及不同推拉电子性与交联官能基的共轭臂，分别命名为；DPPBTDA，DPPPDA和DPPTPTA。为了研究导入添加剂对光电效率与热稳定性提升的影响，我们分别将DPPBTDA，DPPPDA和DPPTPTA掺入以商业化且具有高效率的有机导电高分子（PTB7-Th）作为供体和富勒烯衍生物（PC61BM）作为受体组成的活性层中。探讨不同添加量的DPPBTDA、DPPPDA或DPPTPTA於倒置结构中的形貌变化与光电特性。在光伏性能方面，5 wt％DPPBTDA时展现了6.75 ％的功率转换效率，而5％DPPPDA的OPV显示7.35％的PCE。其中呈现最高光电转换效率的为PTB7-Th：PC61BM与DPPTPTA为3 wt％时呈现高达8.11％的光电转换效率，达到了20%的效率提升。於热交联反应的部分我们利用FT-IR和DSC进行分析，发现所设计的添加剂其反应温度会受其熔点与结晶度所影响。由FT-IR的结果得知本研究所设计的三个添加剂皆能与PC61BM产生交联反应。其加热後的结晶现象也由光学显微镜（OM）的结果得以证实。加入交联剂的活性层在150°C下加热18小时後仅观察到很少的富勒烯晶体，反观未添加交联剂的PTB7-Th:PC61BM共混膜在150°C下加热6小时後便观察到其共混膜产生大量的PCBM结晶。其OM所观察到的现象与光电转换效率相似，未导入添加剂的PTB7-Th:PC61BM共混膜於6小时後便不具光电转换效率，再导入添加剂的部分，其中导入5 wt％的DPPTPTA 在150°C下加热18小时後，功率转换效率保持在4.02％。由电荷迁移率以及AFM的分析结果中得知阶梯状的能阶能有效的提高光电转换效率，且经交联反应後能有效提高PTB7-Th:PC61BM共混膜的热稳定性。

并列摘要〈TOP〉

Part Ⅰ. Conjugated small molecule additives with terminal functional groups
In this work, we prepared four star-shaped conjugated small molecules, the triphenylamine dithiophene (TBT) derivatives, namely TBT-H, TBT-Br, TBT-OH, and TBT-N3 presenting hydride, bromide, hydroxyl, and azide terminal functional groups, respectively. These TBT derivatives were used as additives in the active layers of organic photovoltaics to investigate the effect of intermolecular interactions (TBT-H, TBT-OH) or crosslinking (TBT-N3, TBT-Br) on the long-term thermal stability of the devices. From analyses of blend film morphologies, and optoelectronic and device performance, we observed significant enhancements in thermal stability during accelerated heating tests at 150 °C for the devices incorporated with the additives TBT-N3 and TBT-Br.  These two additives functioned as crosslinkers, and constructed local borders that effectively impeded heat-promoted fullerene aggregation, thereby leading to highly stable morphologies.  When compared with corresponding normal devices, the TBT-N3–derived devices based on poly(3-hexylthiophene) exhibited greater stability, with the power conversion efficiency (PCE) remaining as high as 2.5% after 144 h at 150 °C. Because of this enhancement, a device based on an amorphous low-bandgap polymer, namely poly(thieno[3,4-b]thiophene-alt-benzodithiophene), with the addition of TBT-N3 was fabricated.  We observed a significant improvement in device stability, retaining approximately 60% (from 5.0 to 3.3%) of its initial PCE under accelerated heating (150 °C). In contrast, the PCE of the corresponding normal device decayed to 0.01% of its initial value.

Part II. Visibly Transparent Low Bandgap Conjugated Polymers
In this study, we synthesized two emeraldicene (EMD) based conjugated polymers, by polymerization with 4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole and (2-ethylhexyl) -9H-fluorene, namely PBTEMD and PFEMD, respectively. These EMD derivatives polymers were used as donor materials that blend with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) in the active layers of polymer solar cells (PSCs) to investigate their optoelectronic properties and related photovoltaic performance. To best of our knowledge, this is the first study using EMD derivatives for PSC application. We compared their molecular structure, related absorption, energy levels, thermal properties and thermal stability for PSC application. The main absorption of PFEMD is in the range of near IR spectrum (600nm to 800nm). We obtained transparency of greater than 85% for the blend film of PFEMD and the constructed device exhibited the power conversion of 2.5 % under AM 1.5 G (100 mW cm−2). Apart from that, we observed a significant enhancement in thermal stability for the device incorporating an additive crosslinker (TBT-N3), which retaining approximately 60% of its initial PCE under accelerated heating (150 °C). In contrast, the PCE of the corresponding normal device decayed to 0.01% of its initial value.

Part III. Enhancement Device Performance and Stability of Organic Photovoltaics via Incorporating Multifunctional additive
A novel type of crosslinkers based on diketopyrrolopyrrole (DPP) as core, azide groups on the terminal of alkyl chains along with bithienyl, phenyl or terphenyl as conjugated arms (DPPBTDA, DPPPDA and DPPTPTA, accordingly) were developed. In order to investigate the enhancement of efficiency and thermal stability caused by crosslinkers, DPPBTDA, DPPPDA and DPPTPTA were respectively blend into the active layer which consists of a high performance conducting polymer (PTH7-Th) and a fullerene derivative (PC61BM). Inverted organic photovoltaics (OPVs) were fabricated by spin-coating the blends of PTB7-Th as donor, PC61BM as acceptor and different amounts of DPPBTDA, DPPPDA or DPPTPTA. In terms of photovoltaic performance, the OPV with 5% DPPBTDA showed the power conversion efficiency (PCE) of 6.75 % whereas the OPV with 5% DPPPDA showed a PCE of 7.35 %. Furthermore, a PCE of 8.11 % was observed for the PTB7-TH:PC61BM blending with 3 % DPPTPTA. On the other hand, the morphology of active layer has to be carefully controlled to offer optimum photovoltaic performances. According to FT-IR and UV-vis analysis, the crosslinking reaction did occur between the additives and PC61BM. The optical microscope (OM) result also indicates that only few fullerene crystals can be observed in the active layers with the crosslinkers upon heating the samples at 150˚C for 18 hours. Especially, the device with 5% DPPTPTA remained a power conversion efficiency of 4.02 % after heated at 150˚C for 18 h. Apart from that, the result of charge mobilities and atomic force microscope (AFM) showed ladder type energy level can be increase photovoltaics performance, and further enhance the thermal stability via crosslinking reactions.

参考文献 ( 161 ) 〈TOP〉

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连结：

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