BN-Anthracene for High-Mobility Organic Optoelectronic Materials through Periphery Engineering

被引:71
作者
Li, Wanhui [1 ]
Du, Cheng-Zhuo [1 ]
Chen, Xing-Yu [1 ]
Fu, Lin [1 ]
Gao, Rong-Rong [1 ]
Yao, Ze-Fan [2 ]
Wang, Jie-Yu [2 ]
Hu, Wenping
Pei, Jian [2 ]
Wang, Xiao-Ye [1 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Peking Univ, Coll Chem & Mol Engn, Ctr Soft Matter Sci & Engn,Beijing Natl Lab Mol S, Key Lab Bioorgan Chem & Mol Engn Minist Educ, Beijing 100871, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
Boron; Heterocycles; Organic Semiconductors; Polyarenes; Transistors; FIELD-EFFECT TRANSISTORS; HETEROAROMATIC-COMPOUNDS; REGIOSELECTIVE FUNCTIONALIZATION; PYRENE; SEMICONDUCTORS; REACTIVITY;
D O I
10.1002/anie.202201464
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite the remarkable synthetic accomplishments in creating diverse polycyclic aromatic hydrocarbons with B-N bonds (BN-PAHs), their optoelectronic applications have been less exploited. Herein, we report the achievement of high-mobility organic semiconductors based on existing BN-PAHs through a "periphery engineering" strategy. Tetraphenyl- and diphenyl-substituted BN-anthracenes (TPBNA and DPBNA, respectively) are designed and synthesized. DPBNA exhibits the highest hole mobility of 1.3 cm(2) V-1 s(-1) in organic field-effect transistors, significantly outperforming TPBNA and all the reported BN-PAHs. Remarkably, this is the first BN-PAH with mobility over 1 cm(2 )V(-1) s(-1), which is a benchmark value for practical applications as compared with amorphous silicon. Furthermore, high-performance phototransistors based on DPBNA are also demonstrated, implying the high potential of BN-PAHs for optoelectronic applications when the "periphery engineering" strategy is implemented.
引用
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页数:6
相关论文
共 67 条
[1]   A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position [J].
Abengozar, Alberto ;
Sucunza, David ;
Garcia-Garcia, Patricia ;
Sampedro, Diego ;
Perez-Redondo, Adrian ;
Vaquero, Juan J. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) :7113-7122
[2]   Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives [J].
Abengozar, Alberto ;
Garcia-Garcia, Patricia ;
Sucunza, David ;
Sampedro, Diego ;
Perez-Reclondo, Adrian ;
Vaquero, Juan J. .
ORGANIC LETTERS, 2019, 21 (08) :2550-2554
[3]   Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene [J].
Abengozar, Alberto ;
Garcia-Garcia, Patricia ;
Sucunza, David ;
Manuel Frutos, Luis ;
Castano, Obis ;
Sampedro, Diego ;
Perez-Redondo, Adrian ;
Vaquero, Juan J. .
ORGANIC LETTERS, 2017, 19 (13) :3458-3461
[4]  
[Anonymous], 2013, ANGEW CHEM, V125, P4642
[5]  
[Anonymous], 2013, ANGEW CHEM, V125, P3199
[6]  
[Anonymous], 2007, ANGEW CHEM, V119, P5028
[7]  
[Anonymous], 2012, ANGEW CHEM
[8]  
[Anonymous], 2019, ANGEW CHEM-GER EDIT, V131, P10818
[9]  
[Anonymous], 2019, Angew. Chem, V131, P11501
[10]  
[Anonymous], 2015, ANGEW CHEM, V127, P15289