[en] Two multiresonant thermally activated delayed fluorescence (MR-TADF) emitters are presented and it is shown how further borylation of a deep-blue MR-TADF emitter, DIDOBNA-N, both blueshifts and narrows the emission producing a new near-UV MR-TADF emitter, MesB-DIDOBNA-N, are shown. DIDOBNA-N emits bright blue light (ΦPL = 444 nm, FWHM = 64 nm, ΦPL = 81%, τd = 23 ms, 1.5 wt% in TSPO1). The deep-blue organic light-emitting diode (OLED) based on this twisted MR-TADF compound shows a very high maximum external quantum efficiency (EQEmax ) of 15.3% for a device with CIEy of 0.073. The fused planar MR-TADF emitter, MesB-DIDOBNA-N shows efficient and narrowband near-UV emission (λPL = 402 nm, FWHM = 19 nm, ΦPL = 74.7%, τd = 133 ms, 1.5 wt% in TSPO1). The best OLED with MesB-DIDOBNA-N, doped in a co-host, shows the highest efficiency reported for a near-UV OLED at 16.2%. With a CIEy coordinate of 0.049, this device also shows the bluest EL reported for a MR-TADF OLED to date.
Disciplines :
Chemistry
Author, co-author :
Suresh, Subeesh Madayanad; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
Zhang, Le; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK ; Organic Semiconductor Centre, SUPA School of Physics and Astronomy, University of St Andrews, St Andrews, KY16 9SS, UK
Matulaitis, Tomas; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
Hall, David ; Université de Mons - UMONS ; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
Si, Changfeng; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
Ricci, Gaetano; Laboratory for Computational Modeling of Functional Materials, Namur Institute of Structured Matter, Université de Namur, Rue de Bruxelles, 61, Namur, 5000, Belgium
Slawin, Alexandra M Z; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
Warriner, Stuart; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, UK
Beljonne, David ; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux
Olivier, Yoann ; Université de Mons - UMONS > Faculté des Science > Service de Chimie des matériaux nouveaux ; Laboratory for Computational Modeling of Functional Materials, Namur Institute of Structured Matter, Université de Namur, Rue de Bruxelles, 61, Namur, 5000, Belgium
Samuel, Ifor D W; Organic Semiconductor Centre, SUPA School of Physics and Astronomy, University of St Andrews, St Andrews, KY16 9SS, UK
Zysman-Colman, Eli ; Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
R400 - Institut de Recherche en Science et Ingénierie des Matériaux Complexys
Funders :
Horizon 2020 Framework Programme Leverhulme Trust Engineering and Physical Sciences Research Council
Funding text :
S.M.S. and L.Z. contributed equally to this work. This project has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska Curie grant agreement No 838885 (NarrowbandSSL). S.M.S. acknowledges support from the Marie Skłodowska-Curie Individual Fellowship (grant agreement No 838885 NarrowbandSSL). The authors would like to thank the Leverhulme Trust (RPG-2016-047) for financial support. E.Z.-C. and I.D.W.S. acknowledge support from EPSRC (EP/L017008, EP/P010482/1). Computational resources have been provided by the Consortium des Équipements de Calcul Intensif (CÉCI), funded by the Fonds de la Recherche Scientifiques de Belgique (F. R. S.-FNRS) under Grant No. 2.5020.11, as well as the Tier-1 supercomputer of the Fédération Wallonie-Bruxelles, infrastructure funded by the Walloon Region under the grant agreement n1117545. Y.O. acknowledges funding by the Fonds de la Recherche Scientifique-FNRS under Grant n°F.4534.21 (MIS-IMAGINE). D.B. is a FNRS Research Director. G.R. acknowledges a grant from the “Fonds pour la formation à la Recherche dans l'Industrie et dans l'Agriculture” (FRIA) of the FRS-FNRS.S.M.S. and L.Z. contributed equally to this work. This project has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska Curie grant agreement No 838885 (NarrowbandSSL). S.M.S. acknowledges support from the Marie Skłodowska‐Curie Individual Fellowship (grant agreement No 838885 NarrowbandSSL). The authors would like to thank the Leverhulme Trust (RPG‐2016‐047) for financial support. E.Z.‐C. and I.D.W.S. acknowledge support from EPSRC (EP/L017008, EP/P010482/1). Computational resources have been provided by the Consortium des Équipements de Calcul Intensif (CÉCI), funded by the Fonds de la Recherche Scientifiques de Belgique (F. R. S.‐FNRS) under Grant No. 2.5020.11, as well as the Tier‐1 supercomputer of the Fédération Wallonie‐Bruxelles, infrastructure funded by the Walloon Region under the grant agreement n1117545. Y.O. acknowledges funding by the Fonds de la Recherche Scientifique‐FNRS under Grant n°F.4534.21 (MIS‐IMAGINE). D.B. is a FNRS Research Director. G.R. acknowledges a grant from the “Fonds pour la formation à la Recherche dans l'Industrie et dans l'Agriculture” (FRIA) of the FRS‐FNRS.
G. Hong, X. Gan, C. Leonhardt, Z. Zhang, J. Seibert, J. M. Busch, S. Bräse, Adv. Mater. 2021, 33, 2005630.
In BT.2020-2 (10/2015), Vol. 2015-10, International Telecommunication Union, Geneva, Switzerland 2015.
a) X. Cai, S.-J. Su, Adv. Funct. Mater. 2018, 28, 1802558;
b) H. Fu, Y.-M. Cheng, P.-T. Chou, Y. Chi, Mater. Today 2011, 14, 472.
a) M. Y. Wong, E. Zysman-Colman, Adv. Mater. 2017, 29, 1605444;
b) N. Aizawa, A. Matsumoto, T. Yasuda, Sci. Adv. 2021, 7, eabe5769.
H. Lee, D. Karthik, R. Lampande, J. H. Ryu, J. H. Kwon, Front. Chem. 2020, 8, 373.
a) S. M. Suresh, D. Hall, D. Beljonne, Y. Olivier, E. Zysman-Colman, Adv. Funct. Mater. 2020, 30, 1908677;
b) J.-W. Huang, Y.-C. Hsu, X. Wu, S. Wang, X.-Q. Gan, W.-Q. Zheng, H. Zhang, Y.-Z. Gong, W.-Y. Hung, P.-T. Chou, W. Zhu, J. Mater. Chem. C 2022, 10, 7866.
J. M. Ha, S. H. Hur, A. Pathak, J.-E. Jeong, H. Y. Woo, NPG Asia Mater. 2021, 13, 53.
S. Chen, H. Xu, Chem. Soc. Rev. 2021, 50, 8639.
J. Shinar, R. Shinar, J. Phys. D: Appl. Phys. 2008, 41, 133001.
a) D. S. Thakare, S. K. Omanwar, P. L. Muthal, S. M. Dhopte, V. K. Kondawar, S. V. Moharil, Phys. Status Solidi 2004, 201, 574.
H. V. Santen, J. H. M. Neijzen, Jpn. J. Appl. Phys. 2003, 42, 1110.
L. T. T. Nhung, H. Nagata, A. Takahashi, M. Aihara, T. Okamoto, T. Shimohata, K. Mawatari, M. Akutagawa, Y. Kinouchi, M. Haraguchi, J. Med. Invest. 2012, 59, 53.
a) H. Zhang, G. Li, X. Guo, K. Zhang, B. Zhang, X. Guo, Y. Li, J. Fan, Z. Wang, D. Ma, B. Z. Tang, Angew. Chem., Int. Ed. 2021, 60, 22241;
b) J. Chen, H. Liu, J. Guo, J. Wang, N. Qiu, S. Xiao, J. Chi, D. Yang, D. Ma, Z. Zhao, B. Z. Tang, Angew. Chem., Int. Ed. 2022, 61, e202116810.
Y. Xu, P. Xu, D. Hu, Y. Ma, Chem. Soc. Rev. 2021, 50, 1030.
H. Hirai, K. Nakajima, S. Nakatsuka, K. Shiren, J. Ni, S. Nomura, T. Ikuta, T. Hatakeyama, Angew. Chem., Int. Ed. 2015, 54, 13581.
N. Ikeda, S. Oda, R. Matsumoto, M. Yoshioka, D. Fukushima, K. Yoshiura, N. Yasuda, T. Hatakeyama, Adv. Mater. 2020, 32, 2004072.
D. Liang, Y. Peng, Y. Fu, M. J. Shearer, J. Zhang, J. Zhai, Y. Zhang, R. J. Hamers, T. L. Andrew, S. Jin, ACS Nano 2016, 10, 6897.
D. H. Ahn, S. W. Kim, H. Lee, I. J. Ko, D. Karthik, J. Y. Lee, J. H. Kwon, Nat. Photonics 2019, 13, 540.
H. J. Kim, M. Godumala, S. K. Kim, J. Yoon, C. Y. Kim, H. Park, J. H. Kwon, M. J. Cho, D. H. Choi, Adv. Opt. Mater. 2020, 8, 1902175.
H. Lim, H. J. Cheon, S.-J. Woo, S.-K. Kwon, Y.-H. Kim, J.-J. Kim, Adv. Mater. 2020, 32, 2004083.
J. Hwang, C. W. Koh, J. M. Ha, H. Y. Woo, S. Park, M. J. Cho, D. H. Choi, ACS Appl. Mater. Interfaces 2021, 13, 61454.
Y. Lee, J.-I. Hong, Adv. Opt. Mater. 2021, 9, 2100406.
Y. Gan, X. Peng, W. Qiu, L. Wang, D. Li, W. Xie, D. Liu, M. Li, J. Lin, S.-J. Su, Chem. Eng. J. 2022, 430, 133030.
H. L. Lee, W. J. Chung, J. Y. Lee, Small 2020, 16, 1907569.
D. Hall, K. Stavrou, E. Duda, A. Danos, S. Bagnich, S. Warriner, A. M. Z. Slawin, D. Beljonne, A. Köhler, A. Monkman, Y. Olivier, E. Zysman-Colman, Mater. Horiz. 2022, 9, 1068.
S. M. Suresh, E. Duda, D. Hall, Z. Yao, S. Bagnich, A. M. Z. Slawin, H. Bässler, D. Beljonne, M. Buck, Y. Olivier, A. Köhler, E. Zysman-Colman, J. Am. Chem. Soc. 2020, 142, 6588.
K. Stavrou, S. M. Suresh, D. Hall, A. Danos, N. Kukhta, A. Slawin, S. Warriner, D. Beljonne, Y. Olivier, A. Monkman, E. Zysman-Colman, Adv. Opt. Mater. 2022, 10, 2200688.
S. Madayanad Suresh, L. Zhang, D. Hall, C. Si, G. Ricci, T. Matulaitis, A. M. Z. Slawin, S. Warriner, Y. Olivier, I. D. W. Samuel, E. Zysman-Colman, Angew. Chem., Int. Ed. 2023, 62, e202215522.
H. J. Kim, T. Yasuda, Adv. Opt. Mater. 2022, 10, 2201714.
T. Agou, J. Kobayashi, T. Kawashima, Org. Lett. 2006, 8, 2241.
D. Hall, J. C. Sancho, A. Pershin, D. Beljonne, E. Zysman-Colman, Y. Olivier, J. Chem. Theory Comput. 2022, 18, 4903.
a) M. K. Etherington, J. Gibson, H. F. Higginbotham, T. J. Penfold, A. P. Monkman, Nat. Commun. 2016, 7, 13680;
b) M. Hempe, N. A. Kukhta, A. Danos, M. A. Fox, A. S. Batsanov, A. P. Monkman, M. R. Bryce, Chem. Mater. 2021, 33, 3066;
d) V. V. Patil, H. L. Lee, I. Kim, K. H. Lee, W. J. Chung, J. Kim, S. Park, H. Choi, W.-J. Son, S. O. Jeon, J. Y. Lee, Adv. Sci. 2021, 8, 2101137.
Y. Olivier, J. C. Sancho-Garcia, L. Muccioli, G. D'Avino, D. Beljonne, J. Phys. Chem. Lett. 2018, 9, 6149.
N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877.
a) D. Song, Y. Yu, L. Yue, D. Zhong, Y. Zhang, X. Yang, Y. Sun, G. Zhou, Z. Wu, J. Mater. Chem. C 2019, 7, 11953;
b) D. H. Ahn, J. H. Maeng, H. Lee, H. Yoo, R. Lampande, J. Y. Lee, J. H. Kwon, Adv. Opt. Mater. 2020, 8, 2000102.
W. H. Melhuish, J. Phys. Chem. 1961, 65, 229.
Y. Tsuchiya, S. Diesing, F. Bencheikh, Y. Wada, P. L. dos Santos, H. Kaji, E. Zysman-Colman, I. D. W. Samuel, C. Adachi, J. Phys. Chem. A 2021, 125, 8074.
Z. Shuai, Chin. J. Chem. 2020, 38, 1223.
D. Sun, S. M. Suresh, D. Hall, M. Zhang, C. Si, D. B. Cordes, A. M. Z. Slawin, Y. Olivier, X. Zhang, E. Zysman-Colman, Mater. Chem. Front. 2020, 4, 2018.
a) S. Wu, W. Li, K. Yoshida, D. Hall, S. Madayanad Suresh, T. Sayner, J. Gong, D. Beljonne, Y. Olivier, I. D. W. Samuel, E. Zysman-Colman, ACS Appl. Mater. Interfaces 2022, 14, 22341;
b) J. A. Knöller, G. Meng, X. Wang, D. Hall, A. Pershin, D. Beljonne, Y. Olivier, S. Laschat, E. Zysman-Colman, S. Wang, Angew. Chem., Int. Ed. 2020, 59, 3156.
J. R. Lakowicz, in Principles of Fluorescence Spectroscopy (Ed: J. R. Lakowicz), Springer US, Boston, MA, USA 1983, pp. 257–301.
S. O. Jeon, S. E. Jang, H. S. Son, J. Y. Lee, Adv. Mater. 2011, 23, 1436.
a) T. Northey, J. Stacey, T. J. Penfold, J. Mater. Chem. C 2017, 5, 11001;
b) T. Serevičius, R. Skaisgiris, J. Dodonova, I. Fiodorova, K. Genevičius, S. Tumkevičius, K. Kazlauskas, S. Juršėnas, J. Phys. Chem. Lett. 2022, 13, 1839.
I. S. Park, H. Min, J. U. Kim, T. Yasuda, Adv. Opt. Mater. 2021, 9, 2101282.
a) M. Nagata, H. Min, E. Watanabe, H. Fukumoto, Y. Mizuhata, N. Tokitoh, T. Agou, T. Yasuda, Angew. Chem., Int. Ed. 2021, 60, 20280;
b) S. Oda, B. Kawakami, Y. Yamasaki, R. Matsumoto, M. Yoshioka, D. Fukushima, S. Nakatsuka, T. Hatakeyama, J. Am. Chem. Soc. 2022, 144, 106;
c) J. Bian, S. Chen, L. Qiu, R. Tian, Y. Man, Y. Wang, S. Chen, J. Zhang, C. Duan, C. Han, H. Xu, Adv. Mater. 2022, 34, 2110547.
a) B. van der Zee, Y. Li, G.-J. A. H. Wetzelaer, P. W. M. Blom, Adv. Electron. Mater. 2022, 8, 2101261;
b) M. Hasan, S. Saggar, A. Shukla, F. Bencheikh, J. Sobus, S. K. M. McGregor, C. Adachi, S.-C. Lo, E. B. Namdas, Nat. Commun. 2022, 13, 254.
a) S.-G. Ihn, D. Jeong, E. S. Kwon, S. Kim, Y. S. Chung, M. Sim, J. Chwae, Y. Koishikawa, S. O. Jeon, J. S. Kim, J. Kim, S. Nam, I. Kim, S. Park, D. S. Kim, H. Choi, S. Kim, Adv. Sci. 2022, 9, 2102141;
b) S.-G. Ihn, N. Lee, S. O. Jeon, M. Sim, H. Kang, Y. Jung, D. H. Huh, Y. M. Son, S. Y. Lee, M. Numata, H. Miyazaki, R. Gómez-Bombarelli, J. Aguilera-Iparraguirre, T. Hirzel, A. Aspuru-Guzik, S. Kim, S. Lee, Adv. Sci. 2017, 4, 1600502.