SpringerLink
Log in

Fluorene- and arylamine-based photo-crosslinkable hole transporting polymer for solution-processed perovskite and organic light-emitting diodes

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

Solution-processable techniques, including spin-coating, roll-to-roll printing, and ink-jet printing, are suitable for large-scale manufacturing and flexible displays owing to their cost-effective and simple fabrication. These techniques are widely used in the fabrication of perovskite light-emitting diodes (PeLEDs) and organic light-emitting diodes (OLEDs). However, the energy level modulation between different functional layers, thickness control of the deposited layer, and interlayer mixing between the deposited and subsequent layers may affect the LED performance due to the poor solvent resistance of the deposited layer. Herein, we designed a novel poly[4,4'-(2-(4-((4-hexylphenyl)(phenyl)amino)phenyl)-9H-fluorene-9,9-diyl)bis(N,N-bis(4-butylphenyl)aniline)] (PFTPA-biTPA) as a hole transport layer (HTL) to modulate the hole injection. Subsequently, we introduced the bis(4-azido-2,3,5,6-tetrafluorobenzoate) (FPA) as a photo-crosslinker into the PFTPA-biTPA to prepare the photo-crosslinked HTL for both PeLED and OLED that inhibit attack from the processing solution and suppress the interlayer mixing between the deposited and subsequent layers. Both PeLEDs and OLEDs with photo-crosslinked PFTPA-biTPA exhibited maximum luminance of 175 and 4260 cd/m2 and maximum external quantum efficiency (EQE) of 4.16 and 10.86%, respectively, thus indicating superior properties to those without and with PFTPA-biTPA as the HTLs. Moreover, the photo-crosslinked PFTPA-biTPA showed significantly improved device stability compared to the reference devices having non-photo-crosslinked HTLs in PeLEDs.

Graphical abstract

Schematic illustration of crosslinked hole transport polymer with enhanced hole transport and solvent resistance

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. B. Ma, F. Lauterwasser, L. Deng, C.S. Zonte, B.J. Kim, J.M. Fréchet, C. Borek, M.E. Thompson, Chem. Mater. 19, 4827 (2007)

    Article  CAS  Google Scholar 

  2. S. Park, J.T. Lim, W.-Y. **, H. Lee, B.-H. Kwon, N.S. Cho, J.-H. Han, J.-W. Kang, S. Yoo, J.-I. Lee, ACS Photonics 4, 1114 (2017)

    Article  CAS  Google Scholar 

  3. Y. Wang, W. Wang, Z. Huang, H. Wang, J. Zhao, J. Yu, D. Ma, J. Mater. Chem. C 6, 7042 (2018)

    Article  CAS  Google Scholar 

  4. L. Qian, Y. Zheng, J. Xue, P.H. Holloway, Nat. Photonics 5, 543 (2011)

    Article  CAS  Google Scholar 

  5. S.D. Stranks, H.J. Snaith, Nat. Nanotechnol. 10, 391 (2015)

    Article  CAS  PubMed  Google Scholar 

  6. J. Wang, N. Wang, Y. **, J. Si, Z.K. Tan, H. Du, L. Cheng, X. Dai, S. Bai, H. He, Z. Ye, M.L. Lai, R.H. Friend, W. Huang, Adv. Mater. 27, 2311 (2015)

    Article  CAS  PubMed  Google Scholar 

  7. J. Li, X. Shan, S.G.R. Bade, T. Geske, Q. Jiang, X. Yang, Z. Yu, J. Phys. Chem. Lett. 7, 4059 (2016)

    Article  CAS  PubMed  Google Scholar 

  8. S.-P. Wang, C.-K. Chang, S.-H. Yang, C.-Y. Chang, Y.-C. Chao, Mater. Res. Express 5, 015037 (2018)

    Article  Google Scholar 

  9. C. Li, N. Wang, A. Guerrero, Y. Zhong, H. Long, Y. Miao, J. Bisquert, J. Wang, S. Huettner, J. Phys. Chem. Lett. 10, 6857 (2019)

    Article  CAS  PubMed  Google Scholar 

  10. Y. Shynkarenko, M.I. Bodnarchuk, C. Bernasconi, Y. Berezovska, V. Verteletskyi, S.T. Ochsenbein, M.V. Kovalenko, ACS Energy Lett. 4, 2703 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. N. Kirkwood, B. Singh, P. Mulvaney, Adv. Mater. Interfaces 3, 1600868 (2016)

    Article  Google Scholar 

  12. Y. Zou, M. Ban, Y. Yang, S. Bai, C. Wu, Y. Han, T. Wu, Y. Tan, Q. Huang, X. Gao, T. Song, Q. Zhang, B. Sun, ACS Appl. Mater. Interfaces 10, 24320 (2018)

    Article  CAS  PubMed  Google Scholar 

  13. Y. Liu, T. Wu, Y. Liu, T. Song, B. Sun, APL Mater. 7, 021102 (2019)

    Article  Google Scholar 

  14. Y.S. Shin, Y.J. Yoon, J. Heo, S. Song, J.W. Kim, S.Y. Park, H.W. Cho, G.H. Kim, J.Y. Kim, ACS Appl. Mater. Interfaces 12, 35740 (2020)

    Article  CAS  PubMed  Google Scholar 

  15. C. Zou, Y. Liu, D.S. Ginger, L.Y. Lin, ACS Nano 14, 6076 (2020)

    Article  CAS  PubMed  Google Scholar 

  16. Z. Yu, W.H. Jeong, K. Kang, H. Song, X. Shen, H. Ahn, S.W. Lee, X. Fan, J.W. Jang, S.R. Ha, J.W. Min, J.H. Park, J. Han, E.D. Jung, M.H. Song, D.W. Chang, W.B. Im, S.H. Park, H. Choi, B.R. Lee, J. Mater. Chem. A 10, 13928 (2022)

    Article  CAS  Google Scholar 

  17. Y.H. Kim, H. Cho, J.H. Heo, T.S. Kim, N. Myoung, C.L. Lee, S.H. Im, T.W. Lee, Adv. Mater. 27, 1248 (2015)

    Article  CAS  PubMed  Google Scholar 

  18. C.-Y. Lin, Y.-C. Lin, W.-Y. Hung, K.-T. Wong, R.C. Kwong, S.C. **a, Y.-H. Chen, C.-I. Wu, J. Mater. Chem. 19, 3618 (2009)

    Article  CAS  Google Scholar 

  19. R. Li, L. Cai, Y. Zou, H. Xu, Y. Tan, Y. Wang, J. Li, X. Wang, Y. Li, Y. Qin, D. Liang, T. Song, B. Sun, ACS Appl. Mater. Interfaces 12, 36681 (2020)

    Article  CAS  PubMed  Google Scholar 

  20. W. Sun, L. **e, X. Guo, W. Su, Q. Zhang, ACS Appl. Mater. Interfaces 12, 58369 (2020)

    Article  CAS  PubMed  Google Scholar 

  21. J. Wang, H. Liu, S. Wu, Y. Jia, H. Yu, X. Li, S. Wang, Chem. Eng. J. 391, 123479 (2020)

    Article  CAS  Google Scholar 

  22. J. Zhao, J.A. Bardecker, A.M. Munro, M.S. Liu, Y. Niu, I.-K. Ding, J. Luo, B. Chen, A.K.-Y. Jen, D.S. Ginger, Nano. Lett. 6, 463 (2006)

    Article  CAS  PubMed  Google Scholar 

  23. S.K. Ahn, T. Ban, P. Sakthivel, S.-H. **, Y.-S. Gal, J.H. Lee, Macromol. Res. 20, 459 (2012)

    Article  CAS  Google Scholar 

  24. C.A. Zuniga, J. Abdallah, W. Haske, Y. Zhang, I. Coropceanu, S. Barlow, B. Kippelen, S.R. Marder, Adv. Mater. 25, 1739 (2013)

    Article  CAS  PubMed  Google Scholar 

  25. C.F. Huang, M.L. Keshtov, F.C. Chen, ACS Appl. Mater. Interfaces 8, 27006 (2016)

    Article  CAS  PubMed  Google Scholar 

  26. F.R.P. Limberg, T. Schneider, S. Höfle, F. Reisbeck, S. Janietz, A. Colsmann, H. Krüger, Adv. Func. Mater. 26, 8505 (2016)

    Article  CAS  Google Scholar 

  27. Z. Zhu, D. Zhao, C.-C. Chueh, X. Shi, Z. Li, A.K.Y. Jen, Joule 2, 168 (2018)

    Article  CAS  Google Scholar 

  28. C.C. Lin, S.Y. Yeh, W.L. Huang, Y.X. Xu, Y.S. Huang, T.H. Yeh, C.H. Tien, L.C. Chen, Z.L. Tseng, Polym. (Basel) 12, 2243 (2020)

    Article  CAS  Google Scholar 

  29. K.W. Tsai, M.K. Hung, Y.H. Mao, S.A. Chen, Adv. Func. Mater. 29, 1901025 (2019)

    Article  Google Scholar 

  30. J. Lee, H. Han, J. Lee, S.C. Yoon, C. Lee, J. Mater. Chem. C 2, 1474 (2014)

    Article  CAS  Google Scholar 

  31. J. Park, C. Lee, J. Jung, H. Kang, K.-H. Kim, B. Ma, B.J. Kim, Adv. Func. Mater. 24, 7588 (2014)

    Article  CAS  Google Scholar 

  32. Y. Zou, Y. Liu, M. Ban, Q. Huang, T. Sun, Q. Zhang, T. Song, B. Sun, Nanoscale Horiz 2, 156 (2017)

    Article  CAS  PubMed  Google Scholar 

  33. R.Q. Png, P.J. Chia, J.C. Tang, B. Liu, S. Sivaramakrishnan, M. Zhou, S.H. Khong, H.S. Chan, J.H. Burroughes, L.L. Chua, R.H. Friend, P.K. Ho, Nat. Mater. 9, 152 (2010)

    Article  CAS  PubMed  Google Scholar 

  34. G.W. Preston, A.J. Wilson, Chem. Soc. Rev. 42, 3289 (2013)

    Article  CAS  PubMed  Google Scholar 

  35. S.-H. Jeong, S. Ahn, T.-W. Lee, Macromol. Res. 27, 2 (2018)

    Article  Google Scholar 

  36. J.Y. Park, J.H. Jang, J.H. Lee, D.H. Hwang, J. Nanosci. Nanotechnol. 20, 4661 (2020)

    Article  PubMed  Google Scholar 

  37. C. He, Q. He, X. Yang, G. Wu, C. Yang, F. Bai, Z. Shuai, L. Wang, Y. Li, J. Phys. Chem. C 111, 8661 (2007)

    Article  CAS  Google Scholar 

  38. Z. Ge, T. Hayakawa, S. Ando, M. Ueda, T. Akiike, H. Miyamoto, T. Kajita, M.-A. Kakimoto, Adv. Func. Mater. 18, 584 (2008)

    Article  CAS  Google Scholar 

  39. W. Xu, B. Peng, J. Chen, M. Liang, F. Cai, J. Phys. Chem. C 112, 874 (2008)

    Article  CAS  Google Scholar 

  40. H.T. Lin, C.L. Huang, G.S. Liou, ACS Appl. Mater. Interfaces 11, 11684 (2019)

    Article  CAS  PubMed  Google Scholar 

  41. J.Y. Kim, G. Kwak, Y.C. Choi, D.-H. Kim, Y.S. Han, J. Ind. Eng. Chem. 73, 175 (2019)

    Article  CAS  Google Scholar 

  42. H. Hong, M.Y. Jo, Y.E. Ha, J.H. Kim, Macromol. Res. 21, 321 (2013)

    Article  CAS  Google Scholar 

  43. M. Schock, S. Brase, Molecules 25, 1009 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. J. Li, L. Xu, T. Wang, J. Song, J. Chen, J. Xue, Y. Dong, B. Cai, Q. Shan, B. Han, H. Zeng, Adv. Mater. 29, 1603885 (2017)

    Article  Google Scholar 

  45. S. Kang, R. Jillella, J. Jeong, Y.I. Park, Y.J. Pu, J. Park, ACS Appl. Mater. Interfaces 12, 51756 (2020)

    Article  CAS  PubMed  Google Scholar 

  46. P. Tao, Y. Li, A. Rungta, A. Viswanath, J. Gao, B.C. Benicewicz, R.W. Siegel, L.S. Schadler, J. Mater. Chem. 21, 18623 (2011)

    Article  CAS  Google Scholar 

  47. H. Ha, Y.J. Shim, D.H. Lee, E.Y. Park, I.H. Lee, S.K. Yoon, M.C. Suh, ACS Appl. Mater. Interfaces 13, 21954 (2021)

    Article  CAS  PubMed  Google Scholar 

  48. Z. Yu, S.R. Ha, J.H. Park, E.D. Jung, W.H. Jeong, S. Kim, M.H. Song, J.-M. Kim, S. Lee, S.H. Park, H. Choi, B.R. Lee, J. Power Sources 478, 228810 (2020)

    Article  CAS  Google Scholar 

  49. D. Fan, R. Zhang, Y. Li, C. Shan, W. Li, Y. Wang, F. Xu, H. Fan, Z. Sun, X. Li, M. Zhao, A.K.K. Kyaw, G. Li, J. Wang, W. Huang, Front. Chem. 9, 746365 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. Y. **a, G. Yan, J. Lin, Nanomaterials (Basel) 11, 3119 (2021)

    Article  CAS  PubMed  Google Scholar 

  51. Y.-Q.-Q. Yi, J. Yang, L. **e, Y. Liu, W. Su, Z. Cui, Chem. Eng. J. 439, 135702 (2022)

    Article  CAS  Google Scholar 

  52. H. Shen, W. Cao, N.T. Shewmon, C. Yang, L.S. Li, J. Xue, Nano. Lett. 15, 1211 (2015)

    Article  CAS  PubMed  Google Scholar 

  53. E. Yoon, K.Y. Jang, J. Park, T.W. Lee, Adv. Mater. Interfaces 8, 2001712 (2020)

    Article  Google Scholar 

  54. G. Nedelcu, L. Protesescu, S. Yakunin, M.I. Bodnarchuk, M.J. Grotevent, M.V. Kovalenko, Nano. Lett. 15, 5635 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. H. Yu, G. Tian, W. Xu, S. Wang, H. Zhang, J. Niu, X. Chen, Front. Chem. 6, 381 (2018)

    Article  PubMed  PubMed Central  Google Scholar 

  56. Q. Zheng, F. You, J. Xu, J. **ong, X. Xue, P. Cai, X. Zhang, H. Wang, B. Wei, L. Wang, Org. Electron. 46, 7 (2017)

    Article  CAS  Google Scholar 

  57. Z.P. Yang, H.C. Su, Adv. Func. Mater. 30, 1906788 (2020)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by a Research Grant of Pukyong National University(2021).

Author information

Author notes

  1. Jeong Yong Park and Ji Won Jang have equally contributed to this work.

Authors and Affiliations

  1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, 46241, Republic of Korea

    Jeong Yong Park, Jae-Ho Jang, Seon Lee Kwak & Do-Hoon Hwang

  2. Department of Chemistry, Research Institute for Convergence of Basic Science and Research Institute for Natural Sciences, Hanyang University, Seoul, 04763, Republic of Korea

    Ji Won Jang & Hyosung Choi

  3. Department of Physics, Pukyong National University, Busan, 48513, Republic of Korea

    **nyu Shen & Bo Ram Lee

Authors
  1. Jeong Yong Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ji Won Jang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. **nyu Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jae-Ho Jang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Seon Lee Kwak
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hyosung Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Bo Ram Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Do-Hoon Hwang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Bo Ram Lee or Do-Hoon Hwang.

Ethics declarations

Conflict of interest

The authors declare that there are no conflicts of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 1744 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Park, J.Y., Jang, J.W., Shen, X. et al. Fluorene- and arylamine-based photo-crosslinkable hole transporting polymer for solution-processed perovskite and organic light-emitting diodes. Macromol. Res. 31, 721–732 (2023). https://doi.org/10.1007/s13233-023-00151-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-023-00151-8

Keywords

Search

Navigation