Incorporation of Thieno[3,2-b]pyrrole into Diketopyrrolopyrrole-Based Copolymers for Efficient Organic Field Effect Transistors

被引:24
作者
Bulumulla, Chandima [1 ]
Kularatne, Ruvanthi N. [1 ]
Gunawardhana, Ruwan [1 ]
Nguyen, Hien Q. [1 ]
McCandless, Gregory T. [1 ]
Biewer, Michael C. [1 ]
Stefan, Mihaela C. [1 ,2 ]
机构
[1] Univ Texas Dallas, Dept Chem & Biochem, Richardson, TX 75080 USA
[2] Univ Texas Dallas, Dept Bioengn, Richardson, TX 75080 USA
关键词
THIN-FILM TRANSISTORS; POLYMER SOLAR-CELLS; CONJUGATED POLYMERS; SMALL MOLECULES; CARRIER MOBILITY; HOLE MOBILITIES; SIDE-CHAINS; PERFORMANCE; SEMICONDUCTORS; AMBIPOLAR;
D O I
10.1021/acsmacrolett.8b00236
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Recent advancements in organic field effect transistors have switched chemists' focus from synthesizing libraries of organic semiconductors to a more targeted approach where chemical alterations are performed on known semi-conductors to further improve electronic properties. Among successful semi-conducting polymer candidates, copolymers based on diketopyrrolopyrrole-and thieno[3,2-b]thiophene [P(DPP-TT)] have been subjected to modifications on the diketopyrrolopyrrole unit by using flanking groups and side chain engineering. Thieno[3,2-b]thiophene moiety, however, has seen minimal modifications due to the limited number of modifying sites. Isoelectronic thieno[3,2-b]pyrrole could serve as an alternative since it is easily tunable via N-alkylation reactions. Therefore, for the first time, we report the replacement of the thieno[3,2-b]thiophene unit of P(DPP-TT) with thieno[3,2-b]pyrrole unit and its performance in p-channel field effect transistors. The copolymer exhibits linear characteristics to achieve a relatively high average hole mobility of 0.12 cm(2) V-1 s(-1) in bottom-gate/top-contact field effect transistors with threshold voltages as low as 0 V. These preliminary results highlight the potential of this thieno[3,2-b]pyrrole monomer for utilization in organic field effect transistors.
引用
收藏
页码:629 / 634
页数:11
相关论文
共 61 条
[1]   Investigation of Structure-Property Relationships in Diketopyrrolopyrrole-Based Polymer Semiconductors via Side-Chain Engineering [J].
Back, Jang Yeol ;
Yu, Hojeong ;
Song, Inho ;
Kang, Il ;
Ahn, Hyungju ;
Shin, Tae Joo ;
Kwon, Soon-Ki ;
Oh, Joon Hak ;
Kim, Yun-Hi .
CHEMISTRY OF MATERIALS, 2015, 27 (05) :1732-1739
[2]   Copolymers of diketopyrrolopyrrole and thienothiophene for photovoltaic cells [J].
Bijleveld, Johan C. ;
Verstrijden, R. A. Melanie ;
Wienk, Martijn M. ;
Janssen, Rene A. J. .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (25) :9224-9231
[3]   Mobility overestimation due to gated contacts in organic field-effect transistors [J].
Bittle, Emily G. ;
Basham, James I. ;
Jackson, Thomas N. ;
Jurchescu, Oana D. ;
Gundlach, David J. .
NATURE COMMUNICATIONS, 2016, 7
[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]   Thieno[3,2-b]pyrrole-benzothiadiazole Banana-Shaped Small Molecules for Organic Field-Effect Transistors [J].
Bulumulla, Chandima ;
Gunawardhana, Ruwan ;
Kularatne, Ruvanthi N. ;
Hill, Madison E. ;
McCandless, Gregory T. ;
Biewer, Michael C. ;
Stefan, Mihaela C. .
ACS APPLIED MATERIALS & INTERFACES, 2018, 10 (14) :11818-11825
[6]   Biaxially Extended Conjugated Polymers with Thieno[3,2-b]thiophene Building Block for High Performance Field-Effect Transistor Applications [J].
Chao, Pei-Yin ;
Wu, Hung-Chin ;
Lu, Chien ;
Hong, Chian-Wen ;
Chen, Wen-Chang .
MACROMOLECULES, 2015, 48 (16) :5596-5604
[7]   Unsubstituted Benzodithiophene-Based Conjugated Polymers for High-Performance Organic Field-Effect Transistors and Organic Solar Cells [J].
Chen, Weichao ;
Xiao, Manjun ;
Han, Liangliang ;
Zhang, Jidong ;
Jiang, Huanxiang ;
Gu, Chuantao ;
Shen, Wenfei ;
Yang, Renqiang .
ACS APPLIED MATERIALS & INTERFACES, 2016, 8 (30) :19665-19671
[8]   High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2-b]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities [J].
Chen, Zhuoying ;
Lee, Mi Jung ;
Ashraf, Raja Shahid ;
Gu, Yun ;
Albert-Seifried, Sebastian ;
Nielsen, Martin Meedom ;
Schroeder, Bob ;
Anthopoulos, Thomas D. ;
Heeney, Martin ;
McCulloch, Iain ;
Sirringhaus, Henning .
ADVANCED MATERIALS, 2012, 24 (05) :647-+
[9]   A Pseudo-Regular Alternating Conjugated Copolymer Using an Asymmetric Monomer: A High-Mobility Organic Transistor in Nonchlorinated Solvents [J].
Choi, Hyun Ho ;
Baek, Jang Yeol ;
Song, Eunjoo ;
Kang, Boseok ;
Cho, Kilwon ;
Kwon, Soon-Ki ;
Kim, Yun-Hi .
ADVANCED MATERIALS, 2015, 27 (24) :3626-3631
[10]   Evaluation of (E)-1,2-di(furan-2-yl)ethene as building unit in diketopyrrolopyrrole alternating copolymers for transistors [J].
Du, Jia ;
Bulumulla, Chandima ;
Mejia, Israel ;
McCandless, Gregory T. ;
Biewer, Michael C. ;
Stefan, Mihaela C. .
POLYMER CHEMISTRY, 2017, 8 (39) :6181-6187