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Difluorinated Oligothiophenes for High‐Efficiency All‐Small‐Molecule Organic Solar Cells: Positional Isomeric Effect of Fluorine Substitution on Performance Variations
Solar RRL ( IF 6.0 ) Pub Date : 2020-01-13 , DOI: 10.1002/solr.201900472 Tainan Duan 1, 2 , Jie Gao 1 , Maxime Babics 3 , Zhipeng Kan 1 , Cheng Zhong 4 , Ranbir Singh 5 , Donghong Yu 2 , Jaewon Lee 6 , Zeyun Xiao 1 , Shirong Lu 1
Solar RRL ( IF 6.0 ) Pub Date : 2020-01-13 , DOI: 10.1002/solr.201900472 Tainan Duan 1, 2 , Jie Gao 1 , Maxime Babics 3 , Zhipeng Kan 1 , Cheng Zhong 4 , Ranbir Singh 5 , Donghong Yu 2 , Jaewon Lee 6 , Zeyun Xiao 1 , Shirong Lu 1
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Three symmetrically difluorinated organic semiconductors (namely D5T2F‐P, D5T2F‐S, and D5T2F‐T) containing rhodanine‐flanked pentathiophene structures are synthesized and used as donors in all‐small‐molecule organic solar cells (ASM‐OSCs) prepared with the small‐molecule acceptor 2,2′‐((2Z,2′Z)‐((4,4,9,9‐tetrahexyl‐4,9‐dihydro‐s‐indaceno[1,2‐b:5,6‐b′]dithiophene‐2,7‐diyl)bis(methanylylidene))bis(5,6‐difluoro‐3‐oxo‐2,3‐dihydro‐1H‐indene‐2,1‐diylidene))dimalononitrile (IDIC‐4F). The different substitutional positions of fluorine atoms (–F) in the conjugated backbone of the donor molecule lead to various material and photovoltaic properties being exhibited. Among the three isomers, the centrally fluorinated D5T2F‐P exhibits a redshifted absorption spectrum, downshifted highest occupied molecular orbital (HOMO) energy level, and improved miscibility with IDIC‐4F in the blend films, all of which result in superior device performance. The power conversion efficiency (PCE) of the ASM‐OSCs based on D5T2F‐P:IDIC‐4F reaches an impressive value of 9.36% with an open‐circuit voltage (VOC) value of 0.86 V and a short‐circuit current density (JSC) value of 16.94 mA cm−2, whereas those of D5T2F‐S (6.11%) and D5T2F‐T (5.42%) are much lower. In comparison, an ASM‐OSC based on the nonfluorinated analogue DRCN5T fabricated under the same conditions exhibits poorer performance (8.03% with IDIC‐4F), revealing 16% enhancement in the PCE achieved through backbone fluorination. The PCE of 9.36% may be one of the highest efficiencies of oligothiophene‐based ASM‐OSCs reported in the literature to date.
中文翻译：
高效全小分子有机太阳能电池的二氟化寡聚噻吩：氟取代对性能变化的位置异构影响
合成了三个包含若丹宁侧翼的五噻吩结构的对称二氟化有机半导体（即D5T2F‐P，D5T2F‐S和D5T2F‐T），并用作由小分子制备的全小分子有机太阳能电池（ASM‐OSC）的供体。分子受体2,2'-（（2Z，2'Z）-（（4,4,9,9-四己基-4,9-二氢-s-茚满[1,2-b：5,6-b ′]二噻吩-2,7-二基）双（亚甲基亚烷基））双（5,6-二氟-3-氧代-2,3-二氢-1H-茚-2,1-二亚甲基））二甲基腈（IDIC-4F） 。供体分子的共轭主链中氟原子（–F）的不同取代位置导致显示出各种材料和光伏特性。在这三种异构体中，中心氟化的D5T2F-P表现出红移的吸收光谱，下移的最高占据分子轨道（HOMO）能级，并改善了与IDIC-4F在混合膜中的混溶性，所有这些都带来了卓越的器件性能。基于D5T2F-P：IDIC-4F的ASM-OSC的功率转换效率（PCE）在开路电压下达到9.36％的惊人值（V OC）值为0.86 V，短路电流密度（J SC）值为16.94 mA cm -2，而D5T2F‐S（6.11％）和D5T2F‐T（5.42％）的值要低得多。相比之下，基于在相同条件下制造的非氟化类似物DRCN5T的ASM‐OSC表现较差（IDIC‐4F为8.03％），表明通过骨架氟化实现的PCE增强了16％。迄今为止，PCE为9.36％可能是基于寡聚噻吩的ASM-OSC的最高效率之一。
更新日期：2020-01-13
中文翻译：
高效全小分子有机太阳能电池的二氟化寡聚噻吩：氟取代对性能变化的位置异构影响
合成了三个包含若丹宁侧翼的五噻吩结构的对称二氟化有机半导体（即D5T2F‐P，D5T2F‐S和D5T2F‐T），并用作由小分子制备的全小分子有机太阳能电池（ASM‐OSC）的供体。分子受体2,2'-（（2Z，2'Z）-（（4,4,9,9-四己基-4,9-二氢-s-茚满[1,2-b：5,6-b ′]二噻吩-2,7-二基）双（亚甲基亚烷基））双（5,6-二氟-3-氧代-2,3-二氢-1H-茚-2,1-二亚甲基））二甲基腈（IDIC-4F） 。供体分子的共轭主链中氟原子（–F）的不同取代位置导致显示出各种材料和光伏特性。在这三种异构体中，中心氟化的D5T2F-P表现出红移的吸收光谱，下移的最高占据分子轨道（HOMO）能级，并改善了与IDIC-4F在混合膜中的混溶性，所有这些都带来了卓越的器件性能。基于D5T2F-P：IDIC-4F的ASM-OSC的功率转换效率（PCE）在开路电压下达到9.36％的惊人值（V OC）值为0.86 V，短路电流密度（J SC）值为16.94 mA cm -2，而D5T2F‐S（6.11％）和D5T2F‐T（5.42％）的值要低得多。相比之下，基于在相同条件下制造的非氟化类似物DRCN5T的ASM‐OSC表现较差（IDIC‐4F为8.03％），表明通过骨架氟化实现的PCE增强了16％。迄今为止，PCE为9.36％可能是基于寡聚噻吩的ASM-OSC的最高效率之一。
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