Electron-Rich Anthracene Semiconductors Containing Triarylamine for Solution-Processed Small-Molecule Organic Solar Cells

被引:15
作者
Choi, Hyeju [2 ]
Ko, Haye Min [2 ]
Cho, Nara [2 ]
Song, Kihyung [3 ]
Lee, Jae Kwan [1 ]
Ko, Jaejung [2 ]
机构
[1] Chosun Univ, Dept Chem Educ, Kwangju 501759, South Korea
[2] Korea Univ, Dept New Mat Chem, Chungnam 330700, South Korea
[3] Korea Natl Univ Educ, Dept Chem Educ, Chungbuk 333791, South Korea
基金
新加坡国家研究基金会;
关键词
anthracenes; bulk heterojunctions; charge transfer; semiconductor; solar cells; PHOTOVOLTAIC CELLS; CHARGE-TRANSPORT; TRIPHENYLAMINE; EFFICIENCY;
D O I
10.1002/cssc.201200242
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New electron-rich anthracene derivatives containing triarylamine hole stabilizers, 2,6-bis[5,5'-bis(N,N'-diphenylaniline)-2,2'-bithiophen-5-yl]-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBTTPA) and 2,6-bis(5,5'-bis{4-[bis(9,9-dimethyl-9H-fluoren-2-yl)amino]phenyl}-2,2'-bithiophen-5-yl)-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBTbisDMFA), linked with p-conjugated bithiophene bridges, were synthesized and their photovoltaic characteristics were investigated in solution-processed small-molecule organic solar cells (SMOSCs). These new materials exhibited superior intramolecular charge transfer from triarylamine to anthracene, leading to a more electron-rich anthracene core that facilitated electron transfer into phenyl-C61-butyric acid methyl ester. Compared with TIPSAntBT and triarylamine, these materials show a threefold improvement in hole-transporting properties and better photovoltaic performance in solution-processed SMOSCs, with the best power conversion efficiency being 2.96?% at a high open-circuit voltage of 0.85 V.
引用
收藏
页码:2045 / 2052
页数:8
相关论文
共 33 条
[1]   Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors:: Studies on structural, electrochemical and charge transport properties [J].
Chen, ZJ ;
Debije, MG ;
Debaerdemaeker, T ;
Osswald, P ;
Würthner, F .
CHEMPHYSCHEM, 2004, 5 (01) :137-140
[2]   Synthesis of annulated thiophene perylene bisimide analogues: their applications to bulk heterojunction organic solar cells [J].
Choi, Hyunbong ;
Paek, Sanghyun ;
Song, Juman ;
Kim, Chulwoo ;
Cho, Nara ;
Ko, Jaejung .
CHEMICAL COMMUNICATIONS, 2011, 47 (19) :5509-5511
[3]   Solution-Processed Organic Photovoltaic Cells with Anthracene Derivatives [J].
Chung, Dae Sung ;
Park, Jong Won ;
Yun, Won Min ;
Cha, Hyojung ;
Kim, Yun-Hi ;
Kwon, Soon-Ki ;
Park, Chan Eon .
CHEMSUSCHEM, 2010, 3 (06) :742-748
[4]   High mobility organic single crystal transistors based on soluble triisopropylsilylethynyl anthracene derivatives [J].
Chung, Dae Sung ;
Park, Jong Won ;
Park, Jong-Hwa ;
Moon, Dohyun ;
Kim, Ghyung Hwa ;
Lee, Heung-Soo ;
Lee, Dong Hoon ;
Shim, Hong-Ku ;
Kwon, Soon-Ki ;
Park, Chan Eon .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (03) :524-530
[5]   Light-emitting organic solar cells based on a 3D conjugated system with internal charge transfer [J].
Cravino, Antonio ;
Leriche, Philippe ;
Aleveque, Olivier ;
Roquet, Sophie ;
Roncali, Jean .
ADVANCED MATERIALS, 2006, 18 (22) :3033-+
[6]   Manipulation of the Open-Circuit Voltage of Organic Solar Cells by Desymmetrization of the Structure of Acceptor-Donor-Acceptor Molecules [J].
Demeter, Dora ;
Rousseau, Theodulf ;
Leriche, Philippe ;
Cauchy, Thomas ;
Po, Riccardo ;
Roncali, Jean .
ADVANCED FUNCTIONAL MATERIALS, 2011, 21 (22) :4379-4387
[7]   Solar cell efficiency tables (Version 38) [J].
Green, Martin A. ;
Emery, Keith ;
Hishikawa, Yoshihiro ;
Warta, Wilhelm ;
Dunlop, Ewan D. .
PROGRESS IN PHOTOVOLTAICS, 2011, 19 (05) :565-572
[8]   Molecular engineering of Diketopyrrolopyrrole-based photosensitizer for solution processed small molecule bulk heterojunction solar cells [J].
Jeong, Ban-Seok ;
Choi, Hyunbong ;
Cho, Nara ;
Ko, Haye Min ;
Lim, Woocherl ;
Song, Kihyung ;
Lee, Jae Kwan ;
Ko, Jaejung .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2011, 95 (07) :1731-1740
[9]   Molecular engineering of organic sensitizers containing indole moiety for dye-sensitized solar cells [J].
Kim, Duckhyun ;
Kang, Moon-Sung ;
Song, Kihyung ;
Kang, Sang Ook ;
Ko, Jaejung .
TETRAHEDRON, 2008, 64 (45) :10417-10424
[10]   Molecular engineering of push-pull chromophore for efficient bulk-heterojunction morphology in solution processed small molecule organic photovoltaics [J].
Ko, Haye Min ;
Choi, Hyunbong ;
Paek, Sanghyun ;
Kim, Kyungjun ;
Song, Kihyung ;
Lee, Jae Kwan ;
Ko, Jaejung .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (20) :7248-7253