Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells
Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells
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DOI：
10.1021/ja910420t
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发表时间：
2010-05-05
影响因子：
15
通讯作者：
Taticchi, Aldo
中科院分区：
文献类型：
--
作者：
Silvestri, Fabio;Marrocchi, Assunta;Taticchi, Aldo
本文报道了一系列5个扩链芳基乙炔类化合物的合成和表征，它们是9，10-双{[m，p]-双己氧基苯基乙炔基蒽（A-P6t，1），9，10-bis-[（p-{[m，p-双（己氧基）苯基]乙炔基}苯基）乙炔基]-蒽（PA-P6t，2），4，7-双-{[m，p-bis己氧基苯基乙炔基}-2，1，3-苯并噻二唑（BTZ-P6t，5），4，7-bis（5-{[m，p-双（己氧基）苯基]乙炔基}噻吩-2-基）-2，1，3-苯并噻二唑（TBTZ-P6 t，6）和7，7 '-（{[间，对-双（己氧基）苯基]乙炔基}-2，1，3-苯并噻二唑-4，4 '-乙炔基）-2，5-噻吩（BTZT-P6 t，7）和两个芳基亚乙烯基，9，10-双-{（E）-[m，p-双9，10-双-[（E）-（p-{（E）-[m，p-双（己氧基）苯基]乙烯基}苯基）乙烯基]-蒽（PA-P6 d，4）。首先描述了光学吸收光谱和电化学氧化还原过程的趋势。接下来，薄膜的微观结构和形态的薄膜沉积在各种条件下从溶液中进行了研究，和有机场效应晶体管（OFFERS）和本体异质结光伏（OPV）电池制造。我们发现，取代炔的分子核心上的烯键显着提高器件的性能。OFET测量表明，所有七种半导体都是FET活性的，并且根据主链结构，当实现最佳膜微结构顺序时，芳基乙炔表现出良好的p型迁移率（μ高达类似于0.1 cm（2）V-1 s（-1））。使用[6，6]-苯基C-61-丁酸甲酯（PCBM）作为电子受体的OPV电池在100 mW/cm（2）的模拟AM 1.5太阳辐照下表现出高达1.3%的功率转换效率（PCE）。这些结果表明，芳基乙炔是有前途的空穴传输材料的p-沟道OFFEs和有前途的有机太阳能电池的应用供体。OFET芳基乙炔空穴迁移率和OPV性能之间的直接相关性进行了鉴定和分析。
We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl} phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that all seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (mu up to similar to 0.1 cm(2) V-1 s(-1)) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C-61-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm(2). These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.