基于均三嗪与DPP结构小分子光伏材料的合成与表征
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摘要
有机小分子太阳能电池材料是一类具有很大应用潜力的光伏材料,它具备了合成成本低,污染小,柔韧性好等诸多优点。同时,与聚合物材料相比又具有合成重复性好,容易提纯的优势。目前使用小分子给体材料的有机太阳能电池的光电转化效率大多在4%以下,而且与聚合物太阳能电池相比,对小分子BHJ结构电池尚缺乏系统的研究,新型材料稀少且效率相对较低。这也充分说明,发展新型有机太阳能电池小分子材料具有非常广泛的发展空间。因此设计合成溶解性、成膜性好,宽吸收,高电荷迁移率的小分子光伏材料成为我们研究的主要目标。
本论文先后使用了吡咯并吡咯烷酮结构(DPP)和1,3,5—均三嗪结构为中心来合成有机小分子光伏材料。
吡咯并吡咯烷酮结构(DPP)是由内酰胺构成的共轭平面双环结构,DPP类衍生物具有相对较低的HOMO、LUMO能级和较宽的吸收光谱。通过设计合成以DPP为核的共轭有机小分子可实现材料的宽吸收、高电荷传输性能。同时,通过在内酰胺结构的氮原子上引入烷基链可明显改善材料的溶解性及成膜性。本论文合成了三种以DPP为中心的有机小分子光伏材料,并且结合理论计算对三种材料的光物理与电化学性能进行了测试。三种材料的带隙宽度,LUMO与HOMO能级,吸收光谱范围都符合相应有机光伏材料的要求。其中D-A-D结构的小分子材料(DHFDPP)具有最好的成膜性,我们选择它作为光伏电池给体材料,通过溶液过程制备了本体异质结结构器件,对材料进行了初步的光伏性能测试,得到的能量转化效率为0.5%。器件的进一步优化还在进行中。
均三嗪结构是苯环上的1,3,5位碳原子被氮原子所取代的杂环芳烃,是一种强的吸电子基团,在配合物与光电材料方面有着广泛的应用,在太阳能电池领域研究较少。本论文使用2,4,6-三对甲酰基苯基-1,3,5-三嗪与对硝基苯乙氰为反应底物来合成小分子光伏材料。在合成反应底物2,4,6-三对甲酰基苯基-1,3,5-三嗪的过程中,发现使用Ni催化碳碳偶联反应可以在温和条件下合成均三嗪衍生物。因此本论文优化了这一合成方法,并合成了一系列的均三嗪衍生物。
Organic solar cells (OSCs) have attracted considerable interest due to their potential for large-scale, cost-effective and environmentally friendly power generation. In OSCs, small molecules (SMs) are of increasing interest due to their outstandingly high absorption coefficients and simple purification procedures in contrast to commonly used conjugated donor polymers, such as poly (3-hexylthiophene)(P3HT). However, most of the energy conversion efficiency obtained from the devices which used small molecule materials is in4%the following. Besides these, a small number of new materials and the lack of a systematic study of SMs research based on the bulk heterojunction (BHJ) concept are very obvious. That is to say the research of new small molecule materials for organic photovoltaic cells has very wide development space. So the main target of our research is to synthesize small molecule photovoltaic materials which have favourable solubility, wide absorption spectrum and high charge transfer efficiency.
In this article, we choose1,3,5-triazines and Diketopyrrolopyrrole (DPP) as the central structure to synthesize small molecule photovoltaic materials.
Diketopyrrolopyrrole (DPP) is a specific structure with two conjugate rings which is composed of the structures of lactams. The small molecules based on DPP have strong interaction because of the p-p functions. So the structure has low HOMO, LUMO and narrow energy band gap. Through the design and synthesis of small molecule materials based on DPP, we can synthesize the SMs which have wide absorption spectrum and high charge transfer efficiency. And by contecting the alkyl chain to the N atom in the structure of lactam, the solubility of the small molecule can be improved obviously. In this article, we have synthesized three small molecule photovoltaic materials based on DPP. And according to the theoretical calculation result, we have tested the HOMO, LUMO and the absorption spectrum of the materials, all of which meet the demand of being OSCs materials. Among the three small molecule materials, the structure of DHFDPP has the best ability of forming the film. So we used this material as the donor and made the solution-processed bulk heterojunction device. Then we tested the photovoltaic performance of the device and the energy conversion efficiency is0.5%, the work of optimizating the device is still in progress.
The structure of triazines is a strong electron withdrawing group. The derivatives of the triazines have been widely used in many respects, such as metal complexes, liquid crystal materials and organic photoelectronic materials. But few articles have reported the OSCs materials based on triazines. So we use the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines and the nitrophenyl acetonitrile as the raw materials to synthesize the small molecule OSCs materials. In the progress of synthesizing the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines, we found that the derives of1,3,5-triazines can be synthesized thourgh the Ni catalyst reactions under mild conditions. So we have optimizated the synthesis method and synthesized a series of derives based on1,3,5-triazines.
本论文先后使用了吡咯并吡咯烷酮结构(DPP)和1,3,5—均三嗪结构为中心来合成有机小分子光伏材料。
吡咯并吡咯烷酮结构(DPP)是由内酰胺构成的共轭平面双环结构,DPP类衍生物具有相对较低的HOMO、LUMO能级和较宽的吸收光谱。通过设计合成以DPP为核的共轭有机小分子可实现材料的宽吸收、高电荷传输性能。同时,通过在内酰胺结构的氮原子上引入烷基链可明显改善材料的溶解性及成膜性。本论文合成了三种以DPP为中心的有机小分子光伏材料,并且结合理论计算对三种材料的光物理与电化学性能进行了测试。三种材料的带隙宽度,LUMO与HOMO能级,吸收光谱范围都符合相应有机光伏材料的要求。其中D-A-D结构的小分子材料(DHFDPP)具有最好的成膜性,我们选择它作为光伏电池给体材料,通过溶液过程制备了本体异质结结构器件,对材料进行了初步的光伏性能测试,得到的能量转化效率为0.5%。器件的进一步优化还在进行中。
均三嗪结构是苯环上的1,3,5位碳原子被氮原子所取代的杂环芳烃,是一种强的吸电子基团,在配合物与光电材料方面有着广泛的应用,在太阳能电池领域研究较少。本论文使用2,4,6-三对甲酰基苯基-1,3,5-三嗪与对硝基苯乙氰为反应底物来合成小分子光伏材料。在合成反应底物2,4,6-三对甲酰基苯基-1,3,5-三嗪的过程中,发现使用Ni催化碳碳偶联反应可以在温和条件下合成均三嗪衍生物。因此本论文优化了这一合成方法,并合成了一系列的均三嗪衍生物。
Organic solar cells (OSCs) have attracted considerable interest due to their potential for large-scale, cost-effective and environmentally friendly power generation. In OSCs, small molecules (SMs) are of increasing interest due to their outstandingly high absorption coefficients and simple purification procedures in contrast to commonly used conjugated donor polymers, such as poly (3-hexylthiophene)(P3HT). However, most of the energy conversion efficiency obtained from the devices which used small molecule materials is in4%the following. Besides these, a small number of new materials and the lack of a systematic study of SMs research based on the bulk heterojunction (BHJ) concept are very obvious. That is to say the research of new small molecule materials for organic photovoltaic cells has very wide development space. So the main target of our research is to synthesize small molecule photovoltaic materials which have favourable solubility, wide absorption spectrum and high charge transfer efficiency.
In this article, we choose1,3,5-triazines and Diketopyrrolopyrrole (DPP) as the central structure to synthesize small molecule photovoltaic materials.
Diketopyrrolopyrrole (DPP) is a specific structure with two conjugate rings which is composed of the structures of lactams. The small molecules based on DPP have strong interaction because of the p-p functions. So the structure has low HOMO, LUMO and narrow energy band gap. Through the design and synthesis of small molecule materials based on DPP, we can synthesize the SMs which have wide absorption spectrum and high charge transfer efficiency. And by contecting the alkyl chain to the N atom in the structure of lactam, the solubility of the small molecule can be improved obviously. In this article, we have synthesized three small molecule photovoltaic materials based on DPP. And according to the theoretical calculation result, we have tested the HOMO, LUMO and the absorption spectrum of the materials, all of which meet the demand of being OSCs materials. Among the three small molecule materials, the structure of DHFDPP has the best ability of forming the film. So we used this material as the donor and made the solution-processed bulk heterojunction device. Then we tested the photovoltaic performance of the device and the energy conversion efficiency is0.5%, the work of optimizating the device is still in progress.
The structure of triazines is a strong electron withdrawing group. The derivatives of the triazines have been widely used in many respects, such as metal complexes, liquid crystal materials and organic photoelectronic materials. But few articles have reported the OSCs materials based on triazines. So we use the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines and the nitrophenyl acetonitrile as the raw materials to synthesize the small molecule OSCs materials. In the progress of synthesizing the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines, we found that the derives of1,3,5-triazines can be synthesized thourgh the Ni catalyst reactions under mild conditions. So we have optimizated the synthesis method and synthesized a series of derives based on1,3,5-triazines.
引文
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