A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics

被引:166
作者
Wang, Suhao [1 ]
Sun, Hengda [1 ]
Erdmann, Tim [2 ,3 ,4 ,9 ]
Wang, Gang [5 ,6 ]
Fazzi, Daniele [7 ,10 ]
Lappan, Uwe [3 ]
Puttisong, Yuttapoom [8 ]
Chen, Zhihua [4 ]
Berggren, Magnus [1 ]
Crispin, Xavier [1 ]
Kiriy, Anton [2 ,3 ]
Voit, Brigitte [2 ,3 ]
Marks, Tobin J. [5 ,6 ]
Fabiano, Simone [1 ,4 ,5 ,6 ]
Facchetti, Antonio [4 ,5 ,6 ]
机构
[1] Linkoping Univ, Dept Sci & Technol, Lab Organ Elect, SE-60174 Norrkoping, Sweden
[2] Tech Univ Dresden, Ctr Advancing Elect Dresden, D-01062 Dresden, Germany
[3] Leibniz Inst Polymerforsch Dresden eV, D-01069 Dresden, Germany
[4] Flexterra Corp, 8025 Lamon Ave, Skokie, IL 60077 USA
[5] Northwestern Univ, Dept Chem, 2145 Sheridan Rd, Evanston, IL 60208 USA
[6] Northwestern Univ, Mat Res Ctr, 2145 Sheridan Rd, Evanston, IL 60208 USA
[7] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany
[8] Linkoping Univ, Dept Phys Chem & Biol, SE-58183 Linkoping, Sweden
[9] IBM Almaden Res Ctr, 650 Harry Rd, San Jose, CA 95120 USA
[10] Univ Cologne, Dept Chem, Inst Phys Chem, Luxemburger Str 116, D-50939 Cologne, Germany
基金
瑞典研究理事会;
关键词
donor-acceptor polymers; doping; NDI-based polymers; n-type polymers; organic thermoelectrics; CHARGE-TRANSPORT; HIGH-PERFORMANCE; CONDUCTING POLYMERS; CONJUGATED POLYMERS; ELECTRON-MOBILITY; MOLECULAR DESIGN; SOLAR-CELLS; TRANSISTORS; DIIMIDE; SEMICONDUCTORS;
D O I
10.1002/adma.201801898
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of a novel naphthalenediimide (NDI)-bithiazole (Tz2)-based polymer [P(NDI2OD-Tz2)] is reported, and structural, thin-film morphological, as well as charge transport and thermoelectric properties are compared to the parent and widely investigated NDI-bithiophene (T2) polymer [P(NDI2OD-T2)]. Since the steric repulsions in Tz2 are far lower than in T2, P(NDI2OD-Tz2) exhibits a more planar and rigid backbone, enhancing p-p chain stacking and intermolecular interactions. In addition, the electron-deficient nature of Tz2 enhances the polymer electron affinity, thus reducing the polymer donor-acceptor character. When n-doped with amines, P(NDI2OD-Tz2) achieves electrical conductivity (approximate to 0.1 S cm(-1)) and a power factor (1.5 mu W m(-1) K-2) far greater than those of P(NDI2OD-T2) (0.003 S cm(-1) and 0.012 mu W m(-1) K-2, respectively). These results demonstrate that planarized NDI-based polymers with reduced donor-acceptor character can achieve substantial electrical conductivity and thermoelectric response.
引用
收藏
页数:6
相关论文
共 56 条
[1]   Range and energetics of charge hopping in organic semiconductors [J].
Abdalla, Hassan ;
Zuo, Guangzheng ;
Kemerink, Martijn .
PHYSICAL REVIEW B, 2017, 96 (24)
[2]   Materials and Applications for Large Area Electronics: Solution-Based Approaches [J].
Arias, Ana Claudia ;
MacKenzie, J. Devin ;
McCulloch, Iain ;
Rivnay, Jonathan ;
Salleo, Alberto .
CHEMICAL REVIEWS, 2010, 110 (01) :3-24
[3]   Preparation of halogenated derivatives of thiazolo[5,4-d]thiazole via direct electrophilic aromatic substitution [J].
Benin, Vladimir ;
Yeates, Alan T. ;
Dudis, Douglas .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (03) :811-819
[4]  
Bubnova O, 2014, NAT MATER, V13, P190, DOI [10.1038/nmat3824, 10.1038/NMAT3824]
[5]  
Bubnova O, 2011, NAT MATER, V10, P429, DOI [10.1038/nmat3012, 10.1038/NMAT3012]
[6]   Very Low Degree of Energetic Disorder as the Origin of High Mobility in an n-channel Polymer Semiconductor [J].
Caironi, Mario ;
Bird, Matt ;
Fazzi, Daniele ;
Chen, Zhihua ;
Di Pietro, Riccardo ;
Newman, Christopher ;
Facchetti, Antonio ;
Sirringhaus, Henning .
ADVANCED FUNCTIONAL MATERIALS, 2011, 21 (17) :3371-3381
[7]   How intermolecular geometrical disorder affects the molecular doping of donor-acceptor copolymers [J].
Di Nuzzo, Daniele ;
Fontanesi, Claudio ;
Jones, Rebecca ;
Allard, Sybille ;
Dumsch, Ines ;
Scherf, Ullrich ;
von Hauff, Elizabeth ;
Schumacher, Stefan ;
Da Como, Enrico .
NATURE COMMUNICATIONS, 2015, 6
[8]   The chemical and structural origin of efficient p-type doping in P3HT [J].
Duong, Duc T. ;
Wang, Chenchen ;
Antono, Erin ;
Toney, Michael F. ;
Salleo, Alberto .
ORGANIC ELECTRONICS, 2013, 14 (05) :1330-1336
[9]   Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers [J].
Eckstein, Brian J. ;
Melkonyan, Ferdinand S. ;
Manley, Eric F. ;
Fabiano, Simone ;
Moua, Aidan R. ;
Chen, Lin X. ;
Facchetti, Antonio ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (41) :14356-14359
[10]   Poly(ethylene imine) Impurities Induce n-doping Reaction in Organic (Semi)Conductors [J].
Fabiano, Simone ;
Braun, Slawomir ;
Liu, Xianjie ;
Weverberghs, Eric ;
Gerbaux, Pascal ;
Fahlman, Mats ;
Berggren, Magnus ;
Crispin, Xavier .
ADVANCED MATERIALS, 2014, 26 (34) :6000-+