High mobility diketopyrrolopyrrole (DPP)-based organic semiconductor materials for organic thin film transistors and photovoltaics

被引:641
作者
Li, Yuning [1 ,2 ]
Sonar, Prashant [3 ]
Murphy, Leanne [1 ,2 ]
Hong, Wei [1 ,2 ]
机构
[1] Univ Waterloo, Dept Chem Engn, Waterloo, ON N2L 3G1, Canada
[2] Univ Waterloo, WIN, Waterloo, ON N2L 3G1, Canada
[3] ASTAR, IMRE, Singapore 117602, Singapore
基金
加拿大自然科学与工程研究理事会;
关键词
FIELD-EFFECT TRANSISTORS; POLYMER SOLAR-CELLS; HIGH-PERFORMANCE AMBIPOLAR; LOW-BAND-GAP; CONJUGATED POLYMERS; CHARGE-TRANSPORT; SMALL MOLECULES; ENERGY-TRANSFER; SIDE-CHAINS; COPOLYMER;
D O I
10.1039/c3ee00015j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In recent years, the electron-accepting diketopyrrolopyrrole (DPP) moiety has been receiving considerable attention for constructing donor-acceptor (D-A) type organic semiconductors for a variety of applications, particularly for organic thin film transistors (OTFTs) and organic photovoltaics (OPVs). Through association of the DPP unit with appropriate electron donating building blocks, the resulting D-A molecules interact strongly in the solid state through intermolecular D-A and pi-pi interactions, leading to highly ordered structures at the molecular and microscopic levels. The closely packed molecules and crystalline domains are beneficial for intermolecular and interdomain (or intergranular) charge transport. Furthermore, the energy levels can be readily adjusted, affording p-type, n-type, or ambipolar organic semiconductors with highly efficient charge transport properties in OTFTs. In the past few years, a number of DPP-based small molecular and polymeric semiconductors have been reported to show mobility close to or greater than 1 cm(2) V-1 s(-1). DPP-based polymer semiconductors have achieved record high mobility values for p-type (hole mobility: 10.5 cm(2) V-1 s(-1)), n-type (electron mobility: 3 cm(2) V-1 s(-1)), and ambipolar (hole/electron mobilities: 1.18/1.86 cm(2) V-1 s(-1)) OTFTs among the known polymer semiconductors. Many DPP-based organic semiconductors have favourable energy levels and band gaps along with high hole mobility, which enable them as promising donor materials for OPVs. Power conversion efficiencies (PCE) of up to 6.05% were achieved for OPVs using DPP-based polymers, demonstrating their potential usefulness for the organic solar cell technology. This article provides an overview of the recent exciting progress made in DPP-containing polymers and small molecules that have shown high charge carrier mobility, around 0.1 cm(2) V-1 s(-1) or greater. It focuses on the structural design, optoelectronic properties, molecular organization, morphology, as well as performances in OTFTs and OPVs of these high mobility DPP-based materials.
引用
收藏
页码:1684 / 1710
页数:27
相关论文
共 91 条
[21]   Characteristics of High-Performance Ambipolar Organic Field-Effect Transistors Based on a Diketopyrrolopyrrole-Benzothiadiazole Copolymer [J].
Ha, Tae-Jun ;
Sonar, Prashant ;
Singh, Samarendra P. ;
Dodabalapur, Ananth .
IEEE TRANSACTIONS ON ELECTRON DEVICES, 2012, 59 (05) :1494-1500
[22]   High mobility top-gate and dual-gate polymer thin-film transistors based on diketopyrrolopyrrole-naphthalene copolymer [J].
Ha, Tae-Jun ;
Sonar, Prashant ;
Dodabalapur, Ananth .
APPLIED PHYSICS LETTERS, 2011, 98 (25)
[23]   Charge- and energy-transfer processes at polymer/polymer interfaces:: A joint experimental and theoretical study [J].
Halls, JJM ;
Cornil, J ;
dos Santos, DA ;
Silbey, R ;
Hwang, DH ;
Holmes, AB ;
Brédas, JL ;
Friend, RH .
PHYSICAL REVIEW B, 1999, 60 (08) :5721-5727
[24]   AB-INITIO STUDIES OF THE DIPOLE POLARIZABILITIES OF CONJUGATED MOLECULES .5. THE 5-MEMBERED HETEROCYCLICS C(4)H(4)E (E=BH, ALH, CH2, SIH2, NH, PH, O AND S) [J].
HINCHLIFFE, A ;
SOSCUN, HJ .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1995, 331 (1-2) :109-125
[25]   A conjugated polyazine containing diketopyrrolopyrrole for ambipolar organic thin film transistors [J].
Hong, Wei ;
Sun, Bin ;
Aziz, Hany ;
Park, Won-Tae ;
Noh, Yong-Young ;
Li, Yuning .
CHEMICAL COMMUNICATIONS, 2012, 48 (67) :8413-8415
[26]   5,11-Conjugation-extended low-bandgap anthradithiophene-containing polymer exhibiting enhanced thin-film order and field-effect mobility [J].
Jiang, Ying ;
Mei, Jianguo ;
Ayzner, Alexander L. ;
Toney, Michael F. ;
Bao, Zhenan .
CHEMICAL COMMUNICATIONS, 2012, 48 (58) :7286-7288
[27]   Bulk heterojunction solar cells based on a low-bandgap carbazole-diketopyrrolopyrrole copolymer [J].
Jo, Jang ;
Gendron, David ;
Najari, Ahmed ;
Moon, Ji Sun ;
Cho, Shinuk ;
Leclerc, Mario ;
Heeger, Alan J. .
APPLIED PHYSICS LETTERS, 2010, 97 (20)
[28]   Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport [J].
Jones, Brooks A. ;
Facchetti, Antonio ;
Wasielewski, Michael R. ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15259-15278
[29]   A high mobility conjugated polymer based on dithienothiophene and diketopyrrolopyrrole for organic photovoltaics [J].
Jung, Jae Woong ;
Liu, Feng ;
Russell, Thomas P. ;
Jo, Won Ho .
ENERGY & ENVIRONMENTAL SCIENCE, 2012, 5 (05) :6857-6861
[30]   Recent Advances in White Organic Light-Emitting Materials and Devices (WOLEDs) [J].
Kamtekar, Kiran T. ;
Monkman, Andrew P. ;
Bryce, Martin R. .
ADVANCED MATERIALS, 2010, 22 (05) :572-582