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A series of V-shaped small molecule non-fullerene electron acceptors for efficient bulk-heterojunction devices

机译:一系列V形小分子非富勒烯电子受高效散装 - 异质结装置

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摘要

Two simple semiconducting acceptor-acceptor(1)-donor-acceptor (A-A(1)-D-A) modular, small molecule non-fullerene electron acceptors, 2-(4-(7-hexadecyl-1,3,6,8-tetraoxo-3,6,7,8-tetrahydrobenzo[lmn][3,8]phenanthrolin-2(1H)-yl)phenyl)-3-(6-((4-(7-hexadecyl-1,3,6,8-tetraoxo-3,6,7,8-tetrahydrobenzo[lmn] [3,8] phenanthrolin-2(1H)-yl)phenyl)ethynyl)-9-octyl-9H-carbazol-3-yl)buta-1,3-diene-1,1,4,4-tetracarbonitrile (NDICz-5) and 2-(4-(3,3-dicyano-2-(4-(7-hexadecyl-1,3,6,8-tetraoxo-3,6,7,8-tetrahydrobenzo[lmn][3,8] phenanthrolin-2(1H)-yl) phenyl)-1-(6-((4-(7-hexadecyl-1, 3,6,8-tetraoxo-3,6,7,8-tetrahydrobenzo [lmn][3,8] phenanthrolin-2(1H)-yl) phenybethynyl)-9-octyl-9H-carbazol-3-yl)allylidene)cyclohexa-2,5-dien-1-ylidene)malononitrile (NDICz-6), were designed, synthesized and characterized for application in solution-processable bulk-heterojunction solar cells. The optoelectronic and photovoltaic properties of NDICz-5 and NDICz-6 were directly compared with those of a structural analogue, 7,7'-(((9-oetyl-9H-carbazole-3,6-diyl)bis(ethyne-2,1-diyl))bis(4,1-phenylene))bis (2-hexadecylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone) (NDICz-4), which was designed based on an A-D-A format. All of these new materials were designed to be V-shaped and comprised an electron rich carbazole donor core (D) together with electron deficient naphthalene diimide terminal core (A). In the simple A-D-A system, naphthalene diimide was the terminal functionality, whereas in the A-A(1)-D-A system, tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ) derived functionalities were incorporated as A(1) units by keeping D/A units constant. The inclusion of A(1) was mainly done to induce cross-conjugation within the molecular backbone and hence to improve light-harvesting. The physical and optoelectronic properties were characterized by ultraviolet-visible, thermogravimetric analysis, photo-electron spectroscopy in air and cyclic voltammetry. These new materials exhibited energy levels complementing those of the conventional donor polymer poly(3-hexyl thiophene) (P3HT). Solution-processable bulk-heterojunction devices were fabricated with NDICz-4, NDICz-5 and NDICz-6 as non-fullerene electron acceptors. Studies on the photovoltaic properties revealed that the best P3HT: NDI-Cz6-based device showed an impressive enhanced power conversion efficiency of 7.58%, an increase of around two-fold with respect to as-cast blend, after solvent vapor annealing using carbon disulfide. Not only are the results among the best in the current literature using the conventional donor polymer P3HT, but clearly demonstrate that A-A(1)-D-A type, V-shaped small molecules are promising non-fullerene acceptors in the research field of organic solar cells.
机译:两种简单半导体受体 - 受体(1)-Donor-acealor(AA(1)-DA)模块化,小分子非富勒烯电子受体,2-(4-(7-十六烷基-1,3,6,8-四氧化硅) -3,6,7,8-四氢苯并[LMN] [3,8]菲利蛋白-2(1H) - 基)苯基)-3-(6 - ((4-(4-十六烷基-1,3,6, 8-四氧-3,6,7,8-四氢苯肼[LMN] [3,8]菲林-2(1H) - 基)苯基)乙炔基)-9-辛基-9H-咔唑-3-基)BATA-1 ,3-二烯-1,1,4,4-四羰基腈(NDICZ-5)和2-(4-(3,3-二氰-2-(4-(7-十六烷基-1,3,6,8-)四氧-3,6,7,8-四氢苯肼[LMN] [3,8]菲利林-2(1H) - 基)苯基)-1-(6 - ((4-(4-十六烷基-1,3,6) ,8-四氧化氢-3,6,7,8-四氢苯肼[LMN] [3,8]菲利林-2(1H) - 苯基)苯基甲基丙烯基)-9-辛基-9H-咔唑-3-基)烯丙基)环己 - 设计,合成和特征在于溶液加工的散装 - 异质结太阳能电池,设计,合成和表征2,5-DIEN-1- ylidene)。NDICZ-5和NDICZ-6的光电和光伏性能直接与结构类似物,7,7'相比 - (((9-硝基-9H-咔唑-3,6-二基)双(乙炔-2,1-二基))双(4,1-亚苯基))双(2-十六烷基苯并[LMN] [3,8菲基于ADA格式设计的菲利啉-1,3,6,8(2H,7H)-TetOne)(NDICZ-4)。所有这些新材料都设计为V形,并包括电子富含咔唑供体芯(D),以及电子缺乏萘二酰亚胺末端芯(A)。在简单的ADA系统中,萘二酰亚胺是末端官能团,而在AA(1)-DA系统中,通过保持D / A单元恒定地作为(1)单元并入四环乙烯(TCNE)和四环喹啉二甲烷(TCNQ)衍生的官能团。包含(1)的包含以诱导分子骨架内的交叉缀合,从而改善光收获。通过紫外线可见,热重分析,空气和循环伏安法中的光电性能,其特征在于紫外线可见光,热再定分析。这些新材料表现出能量水平补充常规供体聚合物聚(3-己噻吩)(P3HT)的能量水平。溶液可加工的体外 - 异质结装置用NDICZ-4,NdicZ-5和NdicZ-6制备,作为非富烯电子受体。光伏性能的研究表明,最佳的P3HT:基于NDI-CZ6的装置显示出令人印象深刻的增强功率转换效率为7.58%,在使用二硫化碳蒸汽退火的溶剂蒸汽退火后,相对于浇铸共混物的围绕两倍增加。 。使用常规供体聚合物P3HT的当前文献中最好的结果是最佳的,但清楚地证明AA(1)-DA型,V形小分子在有机太阳能电池的研究领域中是有前的非富勒烯受体。

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