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Title: Non‐Conjugated Flexible Linkers in Semiconducting Polymers: A Pathway to Improved Processability without Compromising Device Performance

Journal Article · · Advanced Electronic Materials
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  1. Department of Chemical Engineering Stanford University 443 Via Ortega Stanford CA 94305 USA
  2. Department of Chemical Engineering Stanford University 443 Via Ortega Stanford CA 94305 USA, Stanford Synchrotron Radiation Lightsource SLAC National Accelerator Laboratory Menlo Park CA 94025 USA
  3. Stanford Synchrotron Radiation Lightsource SLAC National Accelerator Laboratory Menlo Park CA 94025 USA

Semiconducting polymers, in contrast to inorganic silicon, are solution processable and can potentially be printed cost efficiently on flexible large‐area substrates. However to do so it is of paramount importance to formulate the polymeric semiconductors into inks with specific viscosities. Herein, the synthesis of a new highly soluble isoindigo monomer and its incorporation into low bandgap semiconducting polymers is presented. Non‐conjugated flexible linkers are introduced into the conjugated backbone in order to modulate the materials processability. The viscoelastic properties of the new polymers are studied in detail by means of rheometry and dynamical mechanical analysis. The solution viscosity is directly proportional to the content of non‐conjugated linkers in the polymer backbone. In organic field‐effect transistors maximum hole mobilities of 1.7 cm 2 V −1 s −1 are achieved with the new polymers. Due to the enhanced solubility all‐polymer solar cells are fabricated by solution shearing, reaching power conversion efficiency values of 3.7%.

Sponsoring Organization:
USDOE
Grant/Contract Number:
DE‐AC02‐76SF00515
OSTI ID:
1401673
Journal Information:
Advanced Electronic Materials, Journal Name: Advanced Electronic Materials Vol. 2 Journal Issue: 7; ISSN 2199-160X
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 60 works
Citation information provided by
Web of Science

References (39)

The path to ubiquitous and low-cost organic electronic appliances on plastic journal April 2004
Side-Chain Engineering of Isoindigo-Containing Conjugated Polymers Using Polystyrene for High-Performance Bulk Heterojunction Solar Cells journal December 2013
Synthesis of copolymer based on naphthalene diimide connected with a non-conjugated flexible linker journal July 2013
Liquid-crystalline semiconducting polymers with high charge-carrier mobility journal March 2006
Isoindigo, a Versatile Electron-Deficient Unit For High-Performance Organic Electronics journal September 2013
Molecular Motion in Ultrathin Polystyrene Films:  Dynamic Mechanical Analysis of Surface and Interfacial Effects journal November 2005
On the Glass Transition of Polymer Semiconductors and Its Impact on Polymer Solar Cell Stability journal March 2015
The relationship between the degree of branching and glass transition temperature of branched polyethylene: experiment and simulation journal January 2014
Differential AC-chip calorimeter for glass transition measurements in ultrathin films journal January 2006
Flow-enhanced solution printing of all-polymer solar cells journal August 2015
Roles of Flexible Chains in Organic Semiconducting Materials journal July 2013
Influence of Alkyl Chain Branching Positions on the Hole Mobilities of Polymer Thin-Film Transistors journal September 2012
Organic materials for printed electronics journal January 2007
Photocurrent Enhancement from Diketopyrrolopyrrole Polymer Solar Cells through Alkyl-Chain Branching Point Manipulation journal July 2013
High-Performance Air-Stable Organic Field-Effect Transistors: Isoindigo-Based Conjugated Polymers journal April 2011
Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers journal February 2014
Side Chain Engineering in Solution-Processable Conjugated Polymers journal September 2013
Removal of Palladium Nanoparticles from Polymer Materials journal February 2005
Computational Modeling of Isoindigo-Based Polymers Used in Organic Solar Cells journal August 2013
Understanding the Electronic Structure of Isoindigo in Conjugated Systems: A Combined Theoretical and Experimental Approach. journal November 2013
Controlling conjugated polymer morphology and charge carrier transport with a flexible-linker approach journal January 2014
High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2- b ]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities journal October 2011
Phase behaviour of liquid-crystalline polymer/fullerene organic photovoltaic blends: thermal stability and miscibility journal January 2011
Stretchable, Large-area Organic Electronics journal May 2010
Benzotrithiophene Copolymers: Influence of Molecular Packing and Energy Levels on Charge Carrier Mobility journal April 2014
Conjugation-Break Spacers in Semiconducting Polymers: Impact on Polymer Processability and Charge Transport Properties journal March 2015
A Ru-Catalyzed Tandem Alkyne−Enone Coupling/Michael Addition:  Synthesis of 4-Methylene-2,6- cis -tetrahydropyrans journal October 2005
Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature journal May 2012
Sub-glass transition annealing enhances polymer solar cell performance journal January 2014
2,5-Bis(2-octyldodecyl)pyrrolo[3,4- c ]pyrrole-1,4-(2 H ,5 H )-dione-Based Donor–Acceptor Alternating Copolymer Bearing 5,5′-Di(thiophen-2-yl)-2,2′-biselenophene Exhibiting 1.5 cm 2 ·V –1 ·s –1 Hole Mobility in Thin-Film Transistors journal July 2011
Impact of Polystyrene Oligomer Side Chains on Naphthalene Diimide-Bithiophene Polymers as n-Type Semiconductors for Organic Field-Effect Transistors journal January 2016
The First Efficient Catalyzed Acylation of Allylsilanes 1 journal January 1996
Chain Folding and Diffusion in Monodisperse Long n -Alkanes by Solid-State NMR journal June 2009
Influence of thermal ageing on the stability of polymer bulk heterojunction solar cells journal March 2007
Quaterthiophene-based dimers containing an ethylene bridge: molecular design, synthesis, and optoelectronic properties journal January 2012
Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl Side Chains journal September 2011
High Performance All-Polymer Solar Cell via Polymer Side-Chain Engineering journal March 2014
Direct Reduction of Alcohols:  Highly Chemoselective Reducing System for Secondary or Tertiary Alcohols Using Chlorodiphenylsilane with a Catalytic Amount of Indium Trichloride journal November 2001
Stretchable Figures of Merit in Deformable Electronics journal November 2015

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