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Cyano-Substituted Head-to-Head Polythiophenes: Enabling High-Performance n-Type Organic Thin-Film Transistors
Hang Wang1,2; Jun Huang2,4; Mohammad Afsar Uddin3; Bin Liu2; Peng Chen2; Shengbin Shi2; Yumin Tang2; Guichuan Xing5; Shiming Zhang1; Han Young Woo3; Han Guo2; Xugang Guo2
Source PublicationACS Applied Materials and Interfaces

Polythiophenes, built on the electron-rich thiophene unit, typically possess high-lying energy levels of the lowest unoccupied molecular orbitals (LUMOs) and show hole-transporting properties. In this study, we develop a series of n-type polythiophenes, P1-P3, based on head-to-head-linked 3,3′-dialkoxy-4,4′-dicyano-2,2′-bithiophene (BTCNOR) with distinct side chains. The BTCNOR unit shows not only highly planar backbone conformation enabled by the intramolecular noncovalent sulfur-oxygen interaction but also significantly suppressed LUMO level attributed to the cyano-substitution. Hence, all BTCNOR-based polymer semiconductors exhibit low-lying LUMO levels, which are -1.0 eV lower than that of regioregular poly(3-hexylthiophene) (rr-P3HT), a benchmark p-type polymer semiconductor. Consequently, all of the three polymers can enable unipolar n-type transport characteristics in organic thin-film transistors (OTFTs) with low off-currents (I s) of 10 -10 A and large current on/off ratios (I /I s) at the level of 10 . Among them, polymer P2 with a 2-ethylhexyl side chain offers the highest film ordering, leading to the best device performance with an excellent electron mobility (μ ) of 0.31 cm V s in off-center spin-cast OTFTs. To the best of our knowledge, this is the first report of n-type polythiophenes with electron mobility comparable to the hole mobility of the benchmark p-type rr-P3HT and approaching the electron mobility of the most-studied n-type polymer, poly(naphthalene diimide-alt-bithiophene) (i.e., N2200). The change of charge carrier polarity from p-type (rr-P3HT) to n-type (P2) with comparable mobility demonstrates the obvious effectiveness of our structural modification. Adoption of n-hexadecyl (P1) and 2-butyloctyl (P3) side chains leads to reduced film ordering and results in 1-2 orders of magnitude lower μ s, showing the critical role of side chains in optimizing device performance. This study demonstrates the unique structural features of head-to-head linkage containing BTCNOR for constructing high-performance n-type polymers, i.e., the alkoxy chain for backbone conformation locking and providing polymer solubility as well as the strong electron-withdrawing cyano group for lowering LUMO levels and enabling n-type performance. The design strategy of BTCNOR-based polymers provides useful guidelines for developing n-type polythiophenes.

KeywordConformation Lock Cyano-functionalization Head-to-head Linkage N-type Organic Thin-film Transistors Polythiophene
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Indexed BySCI
WOS Research AreaScience & Technology - Other Topics ; Materials Science
WOS SubjectNanoscience & Nanotechnology ; Materials Science, Multidisciplinary
WOS IDWOS:000461538000048
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Cited Times [WOS]:10   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
Affiliation1.Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, Jiangsu, China
2.Department of Materials Science and Engineering, The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen 518055, Guangdong, China
3.Research Institute for Natural Sciences, Department of Chemistry, Korea University, Seoul 136-713, South Korea
4.Center for Advanced Low-Dimension Materials, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Donghua University, Shanghai 201620, China
5.Institute of Applied Physics and Materials Engineering, University of Macau, Macao 999078, China
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GB/T 7714
Hang Wang,Jun Huang,Mohammad Afsar Uddin,et al. Cyano-Substituted Head-to-Head Polythiophenes: Enabling High-Performance n-Type Organic Thin-Film Transistors[J]. ACS Applied Materials and Interfaces,2019,11(10):10089-10098.
APA Hang Wang.,Jun Huang.,Mohammad Afsar Uddin.,Bin Liu.,Peng Chen.,...&Xugang Guo.(2019).Cyano-Substituted Head-to-Head Polythiophenes: Enabling High-Performance n-Type Organic Thin-Film Transistors.ACS Applied Materials and Interfaces,11(10),10089-10098.
MLA Hang Wang,et al."Cyano-Substituted Head-to-Head Polythiophenes: Enabling High-Performance n-Type Organic Thin-Film Transistors".ACS Applied Materials and Interfaces 11.10(2019):10089-10098.
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