Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors

Article


Liu, Qian, Sun, Huabin, Blaikie, Chula, Caporale, Chiara, Manzhos, Sergei, Feron, Krishna, MacLeod, Jennifer M., Massi, Massimiliano, Bottle, Steven E., Bell, John, Noh, Yong-Young and Sonar, Prashant. 2018. "Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors." New Journal of Chemistry: a journal for new directions in chemistry. 42 (15), pp. 12374-12385. https://doi.org/10.1039/c8nj01453a
Article Title

Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors

ERA Journal ID1370
Article CategoryArticle
AuthorsLiu, Qian (Author), Sun, Huabin (Author), Blaikie, Chula (Author), Caporale, Chiara (Author), Manzhos, Sergei (Author), Feron, Krishna (Author), MacLeod, Jennifer M. (Author), Massi, Massimiliano (Author), Bottle, Steven E. (Author), Bell, John (Author), Noh, Yong-Young (Author) and Sonar, Prashant (Author)
Journal TitleNew Journal of Chemistry: a journal for new directions in chemistry
Journal Citation42 (15), pp. 12374-12385
Number of Pages12
Year2018
Place of PublicationUnited Kingdom
ISSN1144-0546
1369-9261
Digital Object Identifier (DOI)https://doi.org/10.1039/c8nj01453a
Abstract

Here, we design and synthesize three new diketopyrrolopyrrole (DPP) derivatives with naphthalene, possessing large-scaled π-delocalized electronic structure, as the flanking groups and both linear (n-decyl and n-dodecyl) and branched (2-hexyldecyl)alkyl chains as substitutions as active layer for high performance organic field-effect transistors (OFETs). The thermal, photophysical properties, energy levels and solid state molecular stacking have been studied in detail. All the materials show excellent thermal stability with a decomposition temperature of 400 °C, high semi-crystallinity feature, suitable HOMO & LUMO energy levels, and varying crystalline domain sizes in thin films. Bottom-contact/top-gate transistor devices are thus fabricated to investigate the mobility. Encouragingly, all compounds function well in OFET devices and show significant potential as p-type semiconducting materials. The monomer with the n-decyl alkyl chain (D-DPPN) shows the highest mobility of 0.019 cm2 V-1 s-1, with the Ion/Ioff ratio reaching 106. We for the first time synthesize naphthalene flanked DPP monomers and achieve high mobility in OFET devices when using these monomers without any further functionalization as semiconductors directly. The primary result that high mobility is observed for monomers only opens a new way for further DPP application and provides more possibilities for constructing high performance polymeric and small molecular semiconductors based on this new DPP dye.

Keywordsorganic field effect transistors; isoindigotin; semiconducting polymers
ANZSRC Field of Research 2020340399. Macromolecular and materials chemistry not elsewhere classified
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Byline AffiliationsQueensland University of Technology
Dongguk University, Korea
Curtin University
National University of Singapore
University of Newcastle
Institution of OriginUniversity of Southern Queensland
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Jiao, Yalong, Ma, Fengxian, Bell, John, Bilic, Ante and Du, Aijun. 2016. "Two-dimensional boron hydride sheets: High stability, massless dirac fermions, and excellent mechanical properties." Angewandte Chemie. 55 (35), pp. 10292-10295. https://doi.org/10.1002/anie.201604369
Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells
Do, Thu-Trang, Subbiah, Jegadesan, Manzhos, Sergei, Jones, David J, Bell, John M and Sonar, Prashant. 2018. "Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells." Organic Electronics. 62, pp. 12-20. https://doi.org/10.1016/j.orgel.2018.06.040
Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks
Do, Thu Trang, Pham, Hong Duc, Manzhos, Sergei, Bell, John M and Sonar, Prashant. 2017. "Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks." ACS Applied Materials and Interfaces. 9 (20), pp. 16967-16976. https://doi.org/10.1021/acsami.6b16395
Vinylene and benzo[c] [1,2,5]thiadiazole: Effect of the pi-spacer unit on the properties of bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing polymers for n-channel organic field-effect transistors
Do, Thu Trang, Patil, Basanagouda B, Singh, Samarendra P, Yambem, Soniya D, Feron, Krishna, Ostrikov, Kostya (Ken), Bell, John M and Sonar, Prashant. 2018. "Vinylene and benzo[c] [1,2,5]thiadiazole: Effect of the pi-spacer unit on the properties of bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing polymers for n-channel organic field-effect transistors." RSC Advances: an international journal to further the chemical sciences. 8 (68), pp. 38919-38928. https://doi.org/10.1039/c8ra08890j
Indenofluorene-based-copolymers: Influence of electron-deficient benzothiadiazole (BT) and benzooxadiazole (BO) moieties on light emitting devices
Do, Thu-Trang, Matsuki, Keiichiro, Sakanoue, Tomo, Wong, Fu-Lung, Manzhos, Sergei, Lee, Chun-Sing, Bell, John, Takenobu, Taishi and Sonar, Prashant. 2019. "Indenofluorene-based-copolymers: Influence of electron-deficient benzothiadiazole (BT) and benzooxadiazole (BO) moieties on light emitting devices." Organic Electronics. 70, pp. 14-24. https://doi.org/10.1016/j.orgel.2019.03.050
Microstructure and mechanical properties of titanium/steel bimetallic joints
Chu, Qiaoling, Bai, Ruixiang, Zhang, Min, Li, Jihong, Lei, Zhenkun, Hu, Ning, Bell, John M and Yan, Cheng. 2017. "Microstructure and mechanical properties of titanium/steel bimetallic joints." Materials Characterization. 132, pp. 330-337. https://doi.org/10.1016/j.matchar.2017.08.025
Correction: Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors (New Journal of Chemistry (2018) 42 (12374–12385) DOI: 10.1039/C8NJ01453A)
Liu, Qian, Sun, Huabin, Blaikie, Chula, Caporale, Chiara, Manzhos, Sergei, Feron, Krishna, MacLeod, Jennifer M., Massi, Massimiliano, Bottle, Steven E., Bell, John, Noh, Yong-Young and Sonar, Prashant. 2018. "Correction: Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors (New Journal of Chemistry (2018) 42 (12374–12385) DOI: 10.1039/C8NJ01453A)." New Journal of Chemistry: a journal for new directions in chemistry. 42 (19), p. 16384. https://doi.org/10.1039/C8NJ90083C
Benefit assessment of battery plus solar for customers and the grid
Boulaire, Fanny, Narimani, Afsaneh, Bell, John, Drogemuller, Robin, Vine, Desley, Buys, Laurie and Walker, Geoffrey. 2019. "Benefit assessment of battery plus solar for customers and the grid." Energy Strategy Reviews. 26. https://doi.org/10.1016/j.esr.2019.100372
Atypical defect motions in brittle layered sodium titanate nanowires
Bo, Arixin, Chen, Kai, Pickering, Edmund, Zhan, Haifei, Bell, John, Du, Aijun, Zhang, Yongqiang, Wang, Xiaoguang, Zhu, Huaiyong, Shan, Zhiwei and Gu, Yuantong. 2018. "Atypical defect motions in brittle layered sodium titanate nanowires." Journal of Physical Chemistry Letters. 9 (20), pp. 6052-6059. https://doi.org/10.1021/acs.jpclett.8b02349
Building energy optimisation under uncertainty using ACOMV algorithm
Bamdad, Keivan, Cholette, Michael E, Guan, Lisa and Bell, John. 2018. "Building energy optimisation under uncertainty using ACOMV algorithm." Energy and Buildings. 167, pp. 322-333. https://doi.org/10.1016/j.enbuild.2018.02.053
Ant colony algorithm for building energy optimisation problems and comparison with benchmark algorithms
Bamdad, Keivan, Cholette, Michael E, Guan, Lisa and Bell, John. 2017. "Ant colony algorithm for building energy optimisation problems and comparison with benchmark algorithms." Energy and Buildings. 154, pp. 404-414. https://doi.org/10.1016/j.enbuild.2017.08.071
Low hysteresis perovskite solar cells using an electron-beam evaporated WO3-x thin film as the electron transport layer
Ali, Fawad, Pham, Ngoc Duy, Fan, Lijuan, Tiong, Vincent, Ostrikov, Ken, Bell, John M., Wang, Hongxia and Tesfamichael, Tuquabo. 2019. "Low hysteresis perovskite solar cells using an electron-beam evaporated WO3-x thin film as the electron transport layer." ACS Applied Energy Materials. 2 (8), pp. 5456-5464. https://doi.org/10.1021/acsaem.9b00547
Tuning the amount of oxygen vacancies in sputter-deposited SnOx films for enhancing the performance of perovskite solar cells
Ali, Fawad, Pham, Ngoc Duy, Bradford, H. Jonathan, Khoshsirat, Nima, Ostrikov, Ken, Bell, John M, Wang, Hongxia and Tesfamichael, Tuquabo. 2018. "Tuning the amount of oxygen vacancies in sputter-deposited SnOx films for enhancing the performance of perovskite solar cells." ChemSusChem: chemistry and sustainability, energy and materials. 11 (18), pp. 3096-3103. https://doi.org/10.1002/cssc.201801541
Stretchable respiration sensors: Advanced designs and multifunctional platforms for wearable physiological monitoring
Dinh, Toan, Nguyen, Thanh, Phan, Hoang-Phuong, Nguyen, Nam-Trung, Dao, Dzung Viet and Bell, John. 2020. "Stretchable respiration sensors: Advanced designs and multifunctional platforms for wearable physiological monitoring." Biosensors and Bioelectronics. 166. https://doi.org/10.1016/j.bios.2020.112460
Investigation on Temperature-Dependent Electrical Conductivity of Carbon Nanotube/Epoxy Composites for Sustainable Energy Applications
Njuguna, Michael K., Galpaya, Dilini, Yan, Cheng, Colwell, Colwell, Will, Geoffrey, Hu, Ning, Yarlagadda, Prasad and Bell, John M.. 2015. "Investigation on Temperature-Dependent Electrical Conductivity of Carbon Nanotube/Epoxy Composites for Sustainable Energy Applications." Journal of Nanoscience and Nanotechnology. 15 (9), pp. 6957-6964. https://doi.org/10.1166/jnn.2015.10514
Ethanol sensitivity of thermally evaporated nanostructured WO3 thin films doped and implanted with Fe
Ahsan, M., Ahmad, M. Z., Tesfamichael, T., Bell, J. and Yarlagadda, Prasad K. D. V.. 2013. "Ethanol sensitivity of thermally evaporated nanostructured WO3 thin films doped and implanted with Fe." 2nd International Conference on Measurement, Instrumentation and Automation (ICMIA 2013). China 23 - 24 Apr 2013 Scientific.Net. https://doi.org/10.4028/www.scientific.net/AMM.333-335.1938