Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl Side Chains

被引:381
作者
Zhang, Xinran [1 ]
Richter, Lee J. [2 ]
DeLongchamp, Dean M. [1 ]
Kline, R. Joseph [1 ]
Hammond, Matthew R. [1 ]
McCulloch, Iain [4 ,5 ]
Heeney, Martin [4 ,5 ]
Ashraf, Raja S. [4 ,5 ]
Smith, Jeremy N. [5 ,6 ]
Anthopoulos, Thomas D. [5 ,6 ]
Schroeder, Bob [7 ]
Geerts, Yves H. [7 ]
Fischer, Daniel A. [3 ]
Toney, Michael F. [8 ]
机构
[1] NIST, Div Polymers, Gaithersburg, MD 20899 USA
[2] NIST, Surface & Microanal Sci Div, Gaithersburg, MD 20899 USA
[3] NIST, Div Ceram, Gaithersburg, MD 20899 USA
[4] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[5] Univ London Imperial Coll Sci Technol & Med, Ctr Plast Elect, London SW7 2AZ, England
[6] Univ London Imperial Coll Sci Technol & Med, Dept Phys, London SW7 2AZ, England
[7] Univ Libre Bruxelles, Fac Sci, Lab Chim Polymeres, B-1050 Brussels, Belgium
[8] Stanford Synchrotron Radiat Lightsource, Menlo Pk, CA 94025 USA
关键词
FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; HIGH-PERFORMANCE; CHARGE-TRANSPORT; CARRIER MOBILITY; COPOLYMERS; POLY(3-ALKYLTHIOPHENES); MORPHOLOGY; TEXTURE; ORDER;
D O I
10.1021/ja204515s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe a series of highly soluble diketo pyrrolo-pyrrole (DPP)-bithiophene copolymers exhibiting field effect hole mobilities up to 0.74 cm(2) V(-1) s(-1), with a common synthetic motif of bulky 2-octyldodecyl side groups on the conjugated backbone. Spectroscopy, diffraction, and microscopy measurements reveal a transition in molecular packing behavior from a preferentially edge-on orientation of the conjugated plane to a preferentially face-on orientation as the attachment density of the side chains increases. Thermal annealing generally reduces both the face-on population and the misoriented edge-on domains. The highest hole mobilities of this series were obtained from edge-on molecular packing and in-plane liquid-crystalline texture, but films with a bimodal orientation distribution and no discernible in-plane texture exhibited surprisingly comparable mobilities. The high hole mobility may therefore arise from the molecular packing feature common to the entire polymer series: backbones that are strictly oriented parallel to the substrate plane and coplanar with other backbones in the same layer.
引用
收藏
页码:15073 / 15084
页数:12
相关论文
共 53 条
[1]   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
[2]   Ink-jet printed p-type polymer electronics based on liquid-crystalline polymer semiconductors [J].
Baklar, Mohammed ;
Woebkenberg, Paul H. ;
Sparrowe, David ;
Goncalves, Magda ;
McCulloch, Iain ;
Heeney, Martin ;
Anthopoulos, Thomas ;
Stingelin, Natalie .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (10) :1927-1931
[3]   Poly(diketopyrrolopyrrole-terthiophene) for Ambipolar Logic and Photovoltaics [J].
Bijleveld, Johan C. ;
Zoombelt, Arjan P. ;
Mathijssen, Simon G. J. ;
Wienk, Martijn M. ;
Turbiez, Mathieu ;
de Leeuw, Dago M. ;
Janssen, Rene A. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :16616-+
[4]   Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices [J].
Bronstein, Hugo ;
Chen, Zhuoying ;
Ashraf, Rap Shahid ;
Zhang, Weimin ;
Du, Junping ;
Durrant, James R. ;
Tuladhar, Pabitra Shakya ;
Song, Kigook ;
Watkins, Scott E. ;
Geerts, Yves ;
Wienk, Martijn M. ;
Janssen, Rene A. J. ;
Anthopoulos, Thomas ;
Sirringhaus, Henning ;
Heeney, Martin ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3272-3275
[5]   High-mobility ambipolar near-infrared light-emitting polymer field-effect transistors [J].
Buergi, Lukas ;
Turbiez, Mathieu ;
Pfeiffer, Reto ;
Bienewald, Frank ;
Kirner, Hans-Joerg ;
Winnewisser, Carsten .
ADVANCED MATERIALS, 2008, 20 (11) :2217-2224
[6]   X-ray scattering study of thin films of poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene) [J].
Chabinyc, Michael L. ;
Toney, Michael F. ;
Kline, R. Joseph ;
McCulloch, Iain ;
Heeney, Martin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3226-3237
[7]   Lamination method for the study of interfaces in polymeric thin film transistors [J].
Chabinyc, ML ;
Salleo, A ;
Wu, YL ;
Liu, P ;
Ong, BS ;
Heeney, M ;
McCulloch, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :13928-13929
[8]   REGIOCONTROLLED SYNTHESIS OF POLY(3-ALKYLTHIOPHENES) MEDIATED BY RIEKE ZINC - THEIR CHARACTERIZATION AND SOLID-STATE PROPERTIES [J].
CHEN, TA ;
WU, XM ;
RIEKE, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :233-244
[9]   Molecular basis of mesophase ordering in a thiophene-based copolymer [J].
DeLongchamp, Dean M. ;
Kline, R. Joseph ;
Jung, Youngsuk ;
Lin, Eric K. ;
Fischer, Daniel A. ;
Gundlach, David J. ;
Cotts, Sarah K. ;
Moad, Andrew J. ;
Richter, Lee J. ;
Toney, Michael F. ;
Heeney, Martin ;
McCulloch, Iain .
MACROMOLECULES, 2008, 41 (15) :5709-5715
[10]   High carrier mobility polythiophene thin films: Structure determination by experiment and theory [J].
DeLongchamp, Dean M. ;
Kline, R. Joseph ;
Lin, Eric K. ;
Fischer, Daniel A. ;
Richter, Lee J. ;
Lucas, Leah A. ;
Heeney, Martin ;
McCulloch, Iain ;
Northrup, John E. .
ADVANCED MATERIALS, 2007, 19 (06) :833-+