Distannylated Bithiophene Imide: Enabling High‐Performance n‐Type Polymer Semiconductors with an Acceptor–Acceptor Backbone
- 29 May 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 59 (34), 14449-14457
- https://doi.org/10.1002/anie.202002292
Abstract
A distannylated electron‐deficient bithiophene imide (BTI‐Tin) monomer was readily synthesized and polymerized with imide‐functionalized co‐units via Stille coupling to afford homopolymer PBTI and copolymer P(BTI‐BTI2), both featuring acceptor‐acceptor backbone with high molecular weight. Benefitting from their improved electronic property and increased molecular weight, both polymers exhibited excellent unipolar n‐type character in transistors with electron mobility up to 2.60 cm2 V‐1 s‐1. When applied as acceptor materials in all‐polymer solar cells, PBTI and P(BTI‐BTI2) achieved high power conversion efficiency (PCE) of 6.67% and 8.61%, respectively. The PCE (6.67%) of polymer PBTI, synthesized from the novel distannylated monomer, is substantially higher than that (0.14%) of the same polymer PBTI*, synthesized from typical dibrominated monomer. The 8.61% PCE of copolymer P(BTI‐BTI2) is also substantially higher than those (< 1%) of homopolymers synthesized from dibrominated monomers. The results demonstrate the great success of BTI‐Tin for facilely accessing structurally novel n‐type polymers with greatly improved device performance.Keywords
Funding Information
- Junta de Andalucía (UMA18- FEDERJA-080)
- National Research Foundation of Korea (2016M1A2A2940911, 2019R1A6A1A11044070)
This publication has 66 references indexed in Scilit:
- Electron-Deficient Poly(p-phenylene vinylene) Provides Electron Mobility over 1 cm2 V–1 s–1 under Ambient ConditionsJournal of the American Chemical Society, 2013
- Bithiophene-Imide-Based Polymeric Semiconductors for Field-Effect Transistors: Synthesis, Structure−Property Correlations, Charge Carrier Polarity, and Device StabilityJournal of the American Chemical Society, 2011
- Rylene and Related Diimides for Organic ElectronicsAdvanced Materials, 2010
- Recombination Dynamics as a Key Determinant of Open Circuit Voltage in Organic Bulk Heterojunction Solar Cells: A Comparison of Four Different Donor PolymersAdvanced Materials, 2010
- A New Class of Semiconducting Polymers for Bulk Heterojunction Solar Cells with Exceptionally High PerformanceAccounts of Chemical Research, 2010
- Synthesis and Characterization of Thiophene-Containing Naphthalene Diimide n-Type Copolymers for OFET ApplicationsMacromolecules, 2010
- A high-mobility electron-transporting polymer for printed transistorsNature, 2009
- n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide SemiconductorsJournal of the American Chemical Society, 2008
- A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar CellsJournal of the American Chemical Society, 2007
- Light-emitting diodes based on conjugated polymersNature, 1990