Skip to main content
Log in

The first application of push-pull systems based on 1,2,5-oxadiazolo[3,4-b]pyrazine in organic light-emitting diodes and perovskite solar cells

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The possibility of using push-pull systems based on furazanopyrazine in organic light-emitting diodes (OLEDs) and photovoltaic film devices was shown for the first time. The emission of all the obtained light-emitting diodes had a yellow-green color, and a maximum brightness of 45600 cd m−2 was achieved at a maximum current efficiency of 2.9 cd A−1. It was determined that the mobility of charge carriers measured in different current modes for these push-pull systems ranged from 10−4 to 4 · 10−6 cm2 V−1 s−1, considerably exceeding the values of the well-known compound Spiro-MeOTAD, widely used in high-efficiency photovoltaic devices.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. A. B. Sheremetev, I. L. Yudin, Russ. Chem. Rev., 2003, 72, 87; DOI: https://doi.org/10.1070/RC2003v072n01ABEH000776.

    Article  CAS  Google Scholar 

  2. N. N. Makhova, L. I. Belen’kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, Russ. Chem. Rev., 2020, 89, 55; DOI: https://doi.org/10.1070/RCR4914.

    Article  CAS  Google Scholar 

  3. V. P. Zelenov, M. E. Minyaev, Russ. Chem. Bull., 2021, 70, 369; DOI: https://doi.org/10.1007/s11172-021-3094-6.

    Article  CAS  Google Scholar 

  4. Y. Oyumi, T. B. Brill, Combustion and Flame, 1987, 68, 209; DOI: https://doi.org/10.1016/0010-2180(87)90058-7.

    Article  CAS  Google Scholar 

  5. A. B. Sheremetev, V. O. Kulagina, N. S. Aleksandrova, D. E. Dmitriev, Y. A. Strelenko, V. P. Lebedev, Y. N. Matyushin, Propellants, Explosives, Pyrotechnics, 1998, 23, 142; DOI: https://doi.org/10.1002/(SICI)1521-4087(199806)23:3<142::AID-PREP142>3.0.CO;2-X.

    Article  CAS  Google Scholar 

  6. H. Gao, Q. Zhang, J. M. Shreeve, J. Mater. Chem. A, 2020, 8, 4193; DOI: https://doi.org/10.1039/C9TA12704F.

    Article  CAS  Google Scholar 

  7. B. Duan, N. Liu, B. Wang, X. Lu, H. Mo, Molecules, 2019, 24, 3213; DOI: https://doi.org/10.3390/molecules24183213.

    Article  PubMed  PubMed Central  Google Scholar 

  8. Y. Pan, J. Li, B. Cheng, W. Zhu, H. Xiao, Comput. Theor. Chem., 2012, 992, 110; DOI: https://doi.org/10.1016/j.comptc.2012.05.013.

    Article  CAS  Google Scholar 

  9. A. B. Sheremetev, V. L. Korolev, A. A. Potemkin, N. S. Aleksandrova, N. V. Palysaeva, T. H. Hoang, V. P. Sinditskii, K. Y. Suponitsky, Asian J. Org. Chem., 2016, 5, 1388; DOI: https://doi.org/10.1002/ajoc.201600386.

    Article  CAS  Google Scholar 

  10. W. Li, J. Tian, X. Qi, K. Wang, Y. Jin, B. Wang, Q. Zhang, Chemistry Select, 2018, 3, 849; DOI: https://doi.org/10.1002/slct.201702678.

    CAS  Google Scholar 

  11. J. Zhang, P. Yin, L. A. Mitchell, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2016, 4, 7430; DOI: https://doi.org/10.1039/C6TA02384C.

    Article  CAS  Google Scholar 

  12. E. V. Verbitskiy, S. Achelle, F. Bureš, P. le Poul, A. Barsella, Y. A. Kvashnin, G. L. Rusinov, F. Robinle Guen, O. N. Chupakhin, V. N. Charushin, J. Photochem. Photobiol., A: Chemistry, 2021, 404, 112900; DOI: https://doi.org/10.1016/j.jphotochem.2020.112900.

    Article  CAS  Google Scholar 

  13. V. I. Ovcharenko, A. B. Sheremetev, K. V. Strizhenko, S. V. Fokin, G. V. Romanenko, A. S. Bogomyakov, V. A. Morozov, M. A. Syroeshkin, A. Ya. Kozmenkova, A. V. Lalova, M. P. Egorov, Mendeleev Commun., 2021, 31, 784; DOI: https://doi.org/10.1016/j.mencom.2021.11.005.

    Article  CAS  Google Scholar 

  14. E. V. Verbitskiy, Y. A. Kvashnin, A. A. Baranova, K. O. Khokhlov, R. D. Chuvashov, Y. A. Yakovleva, N. I. Makarova, E. V. Vetrova, A. V. Metelitsa, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Dyes and Pigments, 2019, 168, 248; DOI: https://doi.org/10.1016/j.dyepig.2019.04.073.

    Article  CAS  Google Scholar 

  15. E. V. Verbitskiy, Yu. A. Kvashnin, A. A. Baranova, Yu. A. Yakovleva, K. O. Khokhlov, G. L. Rusinov, V. N. Charushin, Russ. Chem. Bull., 2018, 67, 1078; DOI: https://doi.org/10.1007/s11172-018-2183-7.

    Article  CAS  Google Scholar 

  16. Y. A. Kvashnin, E. V. Verbitskiy, O. S. Eltsov, P. A. Slepukhin, A. R. Tameev, N. V. Nekrasova, G. L. Rusinov, J.-M. Nunzi, O. N. Chupakhin, V. N. Charushin, ACS Omega, 2020, 5, 8200; DOI: https://doi.org/10.1021/acsomega.0c00479.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. A. Aukštuolis, M. Girtan, G. Mousdis, R. Mallet, M. Socol, M. Rasheed, A. Stanculescu, Proc. Romanian Acad. A, 2017, 18, 34.

    Google Scholar 

  18. Y. A. Kvashnin, N. A. Kazin, E. V. Verbitskiy, T. S. Svalova, A. V. Ivanova, A. N. Kozitsina, P. A. Sle-pukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, ARKIVOC, 2016, V, 279; DOI: https://doi.org/10.3998/ark.5550190.p009.828.

    Article  Google Scholar 

  19. O. D. Iakobson, O. L. Gribkova, A. R. Tameev, J.-M. Nunzi, Scientific Reports, 2021, 11, 5005; DOI: https://doi.org/10.1038/s41598-021-84452-x.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. J. H. Youn, S. J. Baek, H. P. Kim, D. H. Nam, Y. Lee, J. G. Lee, J. Jang, J. Mater. Chem. C, 2013, 1, 3250; DOI: https://doi.org/10.1039/C3TC00855J.

    Article  CAS  Google Scholar 

  21. A. E. Alexandrov, A. R. Tameev, A. S. Steparuk, R. A. Irgashev, G. L. Rusinov, Russ. Chem. Bull., 2019, 68, 1204; DOI: https://doi.org/10.1007/s11172-019-2541-0.

    Article  CAS  Google Scholar 

  22. A. R. Tameev, A. R. Yusupov, A. V. Vannikov, M. G. Tedoradze, Yu. Yu. Enakieva, Yu. G. Gorbunova, A. Yu. Tsivadze, Protection of Metals and Physical Chemistry of Surfaces, 2018, 54, 1076.

    Article  CAS  Google Scholar 

  23. V. V. Malov, T. Ghosh, V. C. Nair, M. M. Maslov, K. P. Katin, K. N. Narayanan Unni, A. R. Tameev, Mendeleev Commun., 2019, 29, 218. DOI: https://doi.org/10.1016/j.mencom.2019.03.035.

    Article  CAS  Google Scholar 

  24. M. Lampert, P. Mark, Inzhektsionnye toki v tverdykh telakh [Injection Currents in Solids], Moscow, Mir, 1973, 416 pp. (in Russian).

    Google Scholar 

  25. D. S. Saranin, V. N. Mazov, L. O. Luchnikov, D. A. Lypenko, P. A. Gostishev, D. S. Muratov, D. A. Podgorny, D. M. Migunov, S. I. Didenko, M. N. Orlova, D. V. Kuznetsov, A. R. Tameev, A. Di Carlo, J. Mater. Chem. C, 2018, 6, 6179; DOI: https://doi.org/10.1039/C8TC01169A.

    Article  CAS  Google Scholar 

  26. O. L. Gribkova, V. A. Kabanova, A. R. Tameev, A. A. Nekrasov, Technical Physics Letters, 2019, 45, 858; DOI: https://doi.org/10.1134/S1063785019090050.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Verbitskiy.

Additional information

Egor Vladimirovich Verbitskiy, born in 1981, Doctor of Chemical Sciences, in 2021 was elected to the position of Director of the I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences. During his work at the IOS UB RAS, he was repeatedly the responsible executor and supervisor of grants from the Russian Foundation for Basic Research (from 2010 to the present), the Russian Science Foundation (from 2015 to the present), the Council for Grants of the President of the Russian Federation (program for the state support for young Russian scientists — candidates of science for 2014–2015, support programs for leading scientific schools in 2012, 2014, and 2016), programs for fundamental and oriented scientific research of the Ural Branch of the Russian Academy of Sciences. In 2011, he was the winner of the Sverdlovsk Region Governor’s Prize for young scientists in the nomination “for the best work in the field of inorganic and organic chemistry” and the Academician I. Ya. Postovsky Prize for young scientists for the study of the reactivity of 1,3- and 1,4-diazines; in 2014, as part of the team of authors of the research work “Development of new organic materials for molecular electronics and photonics”, was awarded the Academician I. Ya. Postovsky Prize.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 2, pp. 527–533, February, 2023.

No human or animal subjects were used in this research.

The authors declare no competing interests.

This work was financially supported by the Russian Science Foundation (Project No. 18-13-00409 P).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Steparuk, A.S., Kvashnin, Y.A., Rusinov, G.L. et al. The first application of push-pull systems based on 1,2,5-oxadiazolo[3,4-b]pyrazine in organic light-emitting diodes and perovskite solar cells. Russ Chem Bull 72, 527–533 (2023). https://doi.org/10.1007/s11172-023-3816-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3816-7

Key words

Navigation