Skip to main content
Log in

Carbazole-based Multiple Resonance Dendrimers with Narrowband Blue Emission for Solution-Processed OLEDs

  • Research Article
  • Published:
Chinese Journal of Polymer Science Aims and scope Submit manuscript

Abstract

Three carbazole-based multiple resonance dendrimers namely D1-BNN, D2-BNN and D3-BNN, are developed for solution-processed narrowband blue organic light-emitting diodes (OLEDs) by introducing the first-, second-, and third-generation carbazole dendrons in periphery of boron, nitrogen-doped polycyclic aromatic hydrocarbon skeleton. Different from D1-BNN containing first-generation carbazole dendron showing moderate photoluminescent quantum efficiency (PLQY) of 68% in solid state and broadened emission bands with full-width at half maximum (FWHM) increasing from 26 nm to 34 nm upon doping concentration growing from 10 wt% to 40 wt%, D3-BNN with the third-generation carbazole dendron exhibits high PLQY of 92% and weak dependence of photoluminescent spectra on doping concentration, which can remain narrowband emissions with unchanged FWHM of 24 nm at same doping concentration range. Solution-processed OLEDs employing D3-BNN as emitter reveal blue electroluminescence at 477 nm with FWHM of 24 nm, and maximum external quantum efficiency (EQE) of 17.3% which is kept at 14.4% at doping concentration of 40 wt%, much superior than the D1-BNN devices showing maximum EQE of 13.0% that drops to 3.7% at 40 wt% doping concentration.

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.

Similar content being viewed by others

References

  1. Albrecht, K.; Matsuoka, K.; Fujita, K.; Yamamoto, K. Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials. Angew. Chem. Int. Ed. 2015, 54, 5677–5682.

    Article  CAS  Google Scholar 

  2. Li, Y. F.; Xie, G. H.; Gong, S. L.; Wu, K. L.; Yang, C. L. Dendronized delayed fluorescence emitters for non-doped, solution-processed organic light-emitting diodes with high efficiency and low efficiency roll-off simultaneously: two parallel emissive channels. Chem. Sci. 2016, 7, 5441–5447.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Sun, K. Y.; Sun, Y. B.; Tian, W. W.; Liu, D.; Feng, Y. L.; Sun, Y. M.; Jiang, W. Thermally activated delayed fluorescence dendrimers with exciplex-forming dendrons for low-voltage-driving and power-efficient solution-processed OLEDs. J. Mater. Chem. C 2018, 6, 43–49.

    Article  CAS  Google Scholar 

  4. Hirata, S.; Sakai, Y.; Masui, K.; Tanaka, H.; Lee, S. Y.; Nomura, H.; Nakamura, N.; Yasumatsu, M.; Nakanotani, H.; Zhang, Q. S.; Shizu, K.; Miyazaki, H.; Adachi, C. Highly efficient blue electroluminescence based on thermally activated delayed fluorescence. Nat. Mater. 2015, 14, 330–336.

    Article  CAS  PubMed  Google Scholar 

  5. Huang, J.; Nie, H.; Zeng, J. J.; Zhuang, Z. Y.; Gan, S. F.; Cai, Y. J.; Guo, J. J.; Su, S. J.; Zhao, Z. J.; Tang, B. Z. Highly efficient nondoped OLEDs with negligible efficiency roll-off fabricated from aggregation-induced delayed fluorescence luminogens. Angew. Chem. Int. Ed. 2017, 56, 12971–12976.

    Article  CAS  Google Scholar 

  6. Franca, L. G.; Danos, A.; Monkman, A. Spiro donor-acceptor TADF emitters: naked TADF free from inhomogeneity caused by donor acceptor bridge bond disorder. Fast rISC and invariant photophysics in solid state hosts. J. Mater. Chem. C 2022, 10, 1313–1325.

    Article  CAS  Google Scholar 

  7. Huang, M. L.; Li, Y. F.; Wu, K. L.; Luo, J. J.; Xie, G. H.; Li, L.; Yang, C. L. Carbazole-dendronized thermally activated delayed fluorescent molecules with small singlet-triplet gaps for solution-processed organic light-emitting diodes. Dyes Pigments 2018, 153, 92–98.

    Article  CAS  Google Scholar 

  8. Ma, Z. H.; Dong, W. Y.; Hou, J. H.; Duan, Q.; Shao, S. Y.; Wang, L. X. Dendritic host materials with non-conjugated adamantane cores for efficient solution-processed blue thermally activated delayed fluorescence OLEDs. J. Mater. Chem. C 2019, 7, 11845–11850.

    Article  CAS  Google Scholar 

  9. Ma, Z. H.; Dong, W. Y.; Lii, X. L.; Chen, P.; Hou, J. H.; Duan, Q.; Shao, S. Y. Cyclohexane-cored dendritic host materials with high triplet energy for efficient solution-processed blue thermally activated delayed fluorescence OLEDs. Dyes Pigments 2020, 174, 108097.

    Article  CAS  Google Scholar 

  10. Ma, R. R.; Ma, Z. H.; Wang, X. D.; Si, Z. J.; Duan, Q.; Shao, S. Y. Alkoxy-capped carbazole dendrimers as host materials for highly efficient narrowband electroluminescence by solution process. Chem. Eng. J. 2022, 447, 137517.

    Article  CAS  Google Scholar 

  11. Zhou, T.; Qian, Y.; Wang, H. J.; Feng, Q. Y.; Xie, L. H.; Huang, W. Recent advances in substituent effects of blue thermally activated delayed fluorescence small molecules. Acta Chim. Sinica 2021, 79, 557–574.

    Article  CAS  Google Scholar 

  12. Hatakeyama, T.; Shiren, K.; Nakajima, K.; Nomura, S.; Nakatsuka, S.; Kinoshita, K.; Ni, J. P.; Ono, Y.; Ikuta, T. Ultrapure blue thermally activated delayed fluorescence molecules: efficient HOMO-LUMO separation by the multiple resonance effect. Adv. Mater. 2016, 28, 2777–2781.

    Article  CAS  PubMed  Google Scholar 

  13. Li, X.; Shi, Y. Z.; Wang, K.; Zhang, M.; Zheng, C. J.; Sun, D. M.; Dai, G. L.; Fan, X. C.; Wang, D. Q.; Liu, W.; Li, Y. Q.; Yu, J.; Ou, X. M.; Adachi, C.; Zhang, X. H. Thermally activated delayed fluorescence carbonyl derivatives for organic light-emitting diodes with extremely narrow full width at half-maximum. ACS Appl. Mater. Interfaces 2019, 11, 13472–13480.

    Article  CAS  PubMed  Google Scholar 

  14. Han, S. H.; Jeong, J. H.; Yoo, J. W.; Lee, J. Y. Ideal blue thermally activated delayed fluorescence emission assisted by a thermally activated delayed fluorescence assistant dopant through a fast reverse intersystem crossing mediated cascade energy transfer process. J. Mater. Chem. C 2019, 7, 3082–3089.

    Article  CAS  Google Scholar 

  15. Zhang, Y. W.; Zhang, D. D.; Wei, J. B.; Liu, Z. Y.; Lu, Y.; Duan, L. Multi-resonance induced thermally activated delayed fluorophores for narrowband green OLEDs. Angew. Chem. Int. Ed. 2019, 58, 16912–16917.

    Article  CAS  Google Scholar 

  16. Yuan, Y.; Tang, X.; Du, X. Y.; Hu, Y.; Yu, Y. J.; Jiang, Z. Q.; Liao, L. S.; Lee, S. T. The design of fused amine/carbonyl system for efficient thermally activated delayed fluorescence: novel multiple resonance core and electron acceptor. Adv. Opt. Mater. 2019, 7, 1801536.

    Article  Google Scholar 

  17. Kondo, Y.; Yoshiura, K.; Kitera, S.; Nishi, H.; Oda, S.; Gotoh, H.; Sasada, Y.; Yanai, M.; Hatakeyama, T. Narrowband deep-blue organic light-emitting diode featuring an organoboron-based emitter. Nat. Photon. 2019, 13, 678–682.

    Article  CAS  Google Scholar 

  18. Ikeda, N.; Oda, S.; Matsumoto, R.; Yoshioka, M.; Fukushima, D.; Yoshiura, K.; Yasuda, N.; Hatakeyama, T. Solution-processable pure green thermally activated delayed fluorescence emitter based on the multiple resonance effect. Adv. Mater. 2020, 32, 2004072.

    Article  CAS  Google Scholar 

  19. Xu, Y. C.; Cheng, Z.; Li, Z. Q.; Liang, B. Y.; Wang, J. X.; Wei, J. B.; Zhang, Z. L.; Wang, Y. Molecular-structure and device-configuration optimizations toward highly efficient green electroluminescence with narrowband emission and high color purity. Adv. Opt. Mater. 2020, 8, 1902142.

    Article  CAS  Google Scholar 

  20. Xu, Y. C.; Li, C. L.; Li, Z. Q.; Wang, Q. Y.; Cai, X. L.; Wei, J. B.; Wang, Y. Constructing charge-transfer excited states based on frontier molecular orbital engineering: narrowband green electroluminescence with high color purity and efficiency. Angew. Chem. Int. Ed. 2020, 59, 17442–17446.

    Article  CAS  Google Scholar 

  21. Qiu, Y. T.; Xia, H.; Miao, J. S.; Huang, Z. Y.; Li, N. Q.; Cao, X. S.; Han, J. M.; Zhou, C. J.; Zhong, C.; Yang, C. L. Narrowing the electroluminescence spectra of multiresonance emitters for high-performance blue OLEDs by a peripheral decoration strategy. ACS Appl. Mater. Interfaces 2021, 13, 59035–59042.

    Article  CAS  PubMed  Google Scholar 

  22. Park, J.; Lim, J.; Lee, J. H.; Jang, B.; Han, J. H.; Yoon, S. S.; Lee, J. Y. Asymmetric blue multiresonance TADF emitters with a narrow emission band. ACS Appl. Mater. Interfaces 2021, 13, 45798–45805.

    Article  CAS  PubMed  Google Scholar 

  23. Qi, Y. Y.; Ning, W. M.; Zou, Y.; Cao, X. S.; Gong, S. L.; Yang, C. L. Peripheral decoration of multi-resonance molecules as a versatile approach for simultaneous long-wavelength and narrowband emission. Adv. Funct. Mater. 2021, 31, 2102017.

    Article  CAS  Google Scholar 

  24. Yang, M. L.; Shikita, S.; Min, H.; Park, I. S.; Shibata, H.; Amanokura, N.; Yasuda, T. Wide-range color tuning of narrowband emission in multi-resonance organoboron delayed fluorescence materials through rational imine/amine functionalization. Angew. Chem. Int. Ed. 2021, 60, 23142–23147.

    Article  CAS  Google Scholar 

  25. Nagata, M.; Min, H.; Watanabe, E.; Fukumoto, H.; Mizuhata, Y.; Tokitoh, N.; Agou, T.; Yasuda, T. Fused-nonacyclic multi-resonance delayed fluorescence emitter based on ladder-thiaborin exhibiting narrowband sky-blue emission with accelerated reverse intersystem crossing. Angew. Chem. Int. Ed. 2021, 60, 20280–20285.

    Article  CAS  Google Scholar 

  26. Pershin, A.; Hall, D.; Lemaur, V.; Sancho-Garcia, J. C.; Muccioli, L.; Zysman-Colman, E.; Beljonne, D.; Olivier, Y. Highly emissive excitons with reduced exchange energy in thermally activated delayed fluorescent molecules. Nat. Commun. 2019, 10, 597.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Stavrou, K.; Danos, A.; Hama, T.; Hatakeyama, T.; Monkman, A. Hot vibrational states in a high-performance multiple resonance emitter and the effect of excimer quenching on organic light-emitting diodes. ACS Appl. Mater. Interfaces 2021, 13, 8643–8655.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Zhang, Y. W.; Wei, J. B.; Zhang, D. D.; Yin, C.; Li, G. M.; Liu, Z. Y.; Jia, X. Q.; Qiao, J.; Duan, L. Sterically wrapped multiple resonance fluorophors for suppression of concentration quenching and spectrum broadening. Angew. Chem. Int. Ed. 2022, 61, https://doi.org/10.1002/anie.202113206.

  29. Jiang, P. C.; Miao, J. S.; Cao, X. S.; Xia, H.; Pan, K.; Hua, T.; Lv, X. L.; Huang, Z. Y.; Zou, Y.; Yang, C. L. Quenching-resistant multiresonance TADF emitter realizes 40% external quantum efficiency in narrowband electroluminescence at high doping level. Adv. Mater. 2022, 34, https://doi.org/10.1002/adma.202106954.

  30. Wang, T.; Zou, Y.; Huang, Z. Y.; Li, N. Q.; Miao, J. S.; Yang, C. L. Narrowband emissive TADF conjugated polymers towards highly efficient solution-processible OLEDs. Angew. Chem. Int. Ed. 2022, 61, e202211172.

  31. Zhao, L.; Wang, S. M.; Lu, J. H.; Ding, J. Q.; Wang, L. X. Solution processable red iridium dendrimers containing oligocarbazole dendrons for efficient nondoped and doped phosphorescent OLEDs. J. Mater. Chem. C 2017, 5, 9753–9760.

    Article  CAS  Google Scholar 

  32. Pan, K. C.; Li, S. W.; Ho, Y. Y.; Shiu, Y. J.; Tsai, W. L.; Jiao, M.; Lee, W. K.; Wu, C. C.; Chung, C. L.; Chatterjee, T.; Li, Y. S.; Wong, K. T.; Hu, H. C.; Chen, C. C.; Lee, M. T. Efficient and tunable thermally activated delayed fluorescence emitters having orientation-adjustable CN-substituted pyridine and pyrimidine acceptor units. Adv. Funct. Mater. 2016, 26, 7560–7571.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 52073282, 52122309, 51833009 and 21975247), the CAS-Croucher Funding Scheme for Joint Laboratories: PolyU-CIAC Joint Laboratory (No. 121522KYSB20200040) and the Open Project of State Key Laboratory of Supramolecular Structure and Materials (No. sklssm2023019). The authors also acknowledge Network and Computing Center, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Lei Zhao, Cui-Yan Tong or Li-Xiang Wang.

Additional information

Notes

The authors declare no competing financial interest.

Electronic Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, JP., Chen, L., Zhao, L. et al. Carbazole-based Multiple Resonance Dendrimers with Narrowband Blue Emission for Solution-Processed OLEDs. Chin J Polym Sci 41, 802–810 (2023). https://doi.org/10.1007/s10118-023-2977-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10118-023-2977-4

Keywords

Navigation