Alkylated Selenophene-Based Ladder-Type Monomers via a Facile Route for High-Performance Thin-Film Transistor Applications

被引：106

作者：

Fei, Zhuping ^{[1
,3
]}

Han, Yang ^{[1
,2
,3
]}

Gann, Eliot ^{[4
]}

Hodsden, Thomas ^{[1
,3
]}

Chesman, Anthony S. R. ^{[5
]}

McNeill, Christopher R. ^{[4
]}

Anthopoulos, Thomas D. ^{[2
,3
,6
]}

Heeney, Martin ^{[1
,3
]}

机构：

[1] Imperial Coll London, Dept Chem, Exhibit Rd, London SW7 2AZ, England

[2] Imperial Coll London, Dept Phys, Exhibit Rd, London SW7 2AZ, England

[3] Imperial Coll London, Ctr Plast Elect, Exhibit Rd, London SW7 2AZ, England

[4] Monash Univ, Dept Mat Sci & Engn, Clayton, Vic 3800, Australia

[5] CSIRO Mfg, Ian Wark Labs, Clayton, Vic 3168, Australia

[6] King Abdullah Univ Sci & Technol, Div Phys Sci & Engn, Thuwal 239556900, Saudi Arabia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 25期

基金：

澳大利亚研究理事会; 英国工程与自然科学研究理事会;

关键词：

FIELD-EFFECT TRANSISTORS; HETEROJUNCTION SOLAR-CELLS; DONOR-ACCEPTOR POLYMERS; MOBILITY CONJUGATED POLYMERS; SEMICONDUCTING POLYMERS; NAPHTHALENE DIIMIDE; SIDE-CHAIN; PHOTOVOLTAIC APPLICATIONS; OPTOELECTRONIC PROPERTIES; ORGANIC TRANSISTORS;

D O I：

10.1021/jacs.7b03099

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the synthesis of two new selenophene-containing ladder-type monomers, cyclopentadiselenophene (CPDS) and indacenodiselenophene (IDSe), via a 2-fold and 4-fold Pd-catalyzed coupling with a 1,1-diborylmethane derivative. Copolymers with benzothiadiazole were prepared in high yield by Suzuki polymerization to afford materials which exhibited excellent solubility in a range of nonchlorinated solvents. The CPDS copolymer exhibited a band gap of just 1.18 eV, which is among the lowest reported for donor-acceptor polymers. Thin-film transistors were fabricated using environmentally benign, nonchlorinated solvents, with the CPDS and IDSe copolymers exhibiting hole mobility up to 0.15 and 6.4 cm2 V-1 s(-1), respectively. This high performance was achieved without the undesirable peak in mobility often observed at low gate voltages due to parasitic contact resistance.

引用

页码：8552 / 8561

页数：10

共 82 条

[1] Influence of the heteroatom on the optoelectronic properties and transistor performance of soluble thiophene-, selenophene- and tellurophene-vinylene copolymers [J].

Al-Hashimi, Mohammed ;

Han, Yang ;

Smith, Jeremy ;

Bazzi, Hassan S. ;

Alqaradawi, Siham Yousuf A. ;

Watkins, Scott E. ;

Anthopoulos, Thomas D. ;

Heeney, Martin .

CHEMICAL SCIENCE, 2016, 7 (02) :1093-1099

[2] Selenophene vs. thiophene in benzothiadiazole-based low energy gap donor-acceptor polymers for photovoltaic applications [J].

Alghamdi, Abdulaziz A. B. ;

Watters, Darren C. ;

Yi, Hunan ;

Al-Faifi, Solyman ;

Almeataq, Mohammed S. ;

Coles, David ;

Kingsley, James ;

Lidzey, David G. ;

Iraqi, Ahmed .

JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (16) :5165-5171

[3] Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells [J].

Ashraf, Raja Shahid ;

Meager, Iain ;

Nikolka, Mark ;

Kirkus, Mindaugas ;

Planells, Miquel ;

Schroeder, Bob C. ;

Holliday, Sarah ;

Hurhangee, Michael ;

Nielsen, Christian B. ;

Sirringhaus, Henning ;

McCulloch, Iain .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (03) :1314-1321

[4] 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

[5] 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

[6] New Selenophene-Based Low-Band Gap Conjugated Polymers for Organic Photovoltaics [J].

Chang, Ching-Chih ;

Chen, Chih-Ping ;

Chou, Ho-Hsiu ;

Liao, Chuang-Yi ;

Chan, Shu-Hua ;

Cheng, Chien-Hong .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (21) :4550-4557

[7] A New Pentacyclic Indacenodiselenophene Arene and Its Donor-Acceptor Copolymers for Solution-Processable Polymer Solar Cells and Transistors: Synthesis, Characterization, and Investigation of Alkyl/Alkoxy Side-Chain Effect [J].

Chang, Huan-Hsuan ;

Tsai, Che-En ;

Lai, Yu-Ying ;

Liang, Wei-Wei ;

Hsu, So-Lin ;

Hsu, Chain-Shu ;

Cheng, Yen-Ju .

MACROMOLECULES, 2013, 46 (19) :7715-7726

[8] Recent progress in non-fullerene small molecule acceptors in organic solar cells (OSCs) [J].

Chen, Wangqiao ;

Zhang, Qichun .

JOURNAL OF MATERIALS CHEMISTRY C, 2017, 5 (06) :1275-1302

[9] Environmentally benign fabrication processes for high-performance polymeric semiconductors [J].

Cho, Jangwhan ;

Yu, Seong Hoon ;

Chung, Dae Sung .

JOURNAL OF MATERIALS CHEMISTRY C, 2017, 5 (11) :2745-2757

[10] To bend or not to bend - are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity? [J].

Conboy, Gary ;

Spencer, Howard J. ;

Angioni, Enrico ;

Kanibolotsky, Alexander L. ;

Findlay, Neil J. ;

Coles, Simon J. ;

Wilson, Claire ;

Pitak, Mateusz B. ;

Risko, Chad ;

Coropceanu, Veaceslav ;

Bredas, Jean-Luc ;

Skabara, Peter J. .

MATERIALS HORIZONS, 2016, 3 (04) :333-339

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