Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units

Hua-Xiu Ni; Weidong Sun; Xu-Feng Luo; Li Yuan; Xiao Liang; Xiang-Ji Liao; Liang Zhou; You-Xuan Zheng

doi:10.59717/j.xinn-mater.2023.100041

The Innovation Materials > 2023 Vol. 1 > No. 3 > 100041

Next Article Previous Article

ARTICLE Open Access

Cite PDF

Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units

1.
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
2.
State Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
3.
Shenzhen Research Institute of Nanjing University, Shenzhen 518057, China
4.
These authors contributed equally to this work

More Information

Corresponding authors: yxzheng@nju.edu.cn (Y.Z.); zhoul@ciac.ac.cn (L.Z.)
Received Date: 14 September 2023

Accepted Date: 09 November 2023

Published Online: 15 November 2023

The Innovation Materials 1(3), https://doi.org/10.59717/j.xinn-mater.2023.100041 | Cite this article

GRAPHICAL ABSTRACT

GRAPHICAL ABSTRACT

PUBLIC SUMMARY

PUBLIC SUMMARY
1. Four MR-TADF materials modified with non-planar silyl units suppress intermolecular aggregation and increase the properties.
  
  Organic light-emitting diodes with four materials show good performances with high external quantum efficiencies of up to 34.6%.
  
  One of the material and corresponding OLED exhibit pure green emission with CIE coordinates of (0.14, 0.70).

ABSTRACT

ABSTRACT

The rigid planar structure of multiple resonance thermally activated delayed fluorescence (MR-TADF) molecules based on boron/nitrogen (B/N) frameworks always causes a substantial roll-off in organic light-emitting diodes (OLEDs) due to intermolecular aggregation. Herein, four MR-TADF emitters (tCzMe3Si, tCzPh3Si, tPhCzMe3Si, and tPhCzPh3Si) were synthesized by introducing non-planar trimethyl/triphenyl silyl (Me3Si and Ph3Si) units at the para-carbon position of a B-substituted phenyl ring to reduce the intermolecular interaction. We further modified the peripheral electron donors of the B/N core, replacing 3,6-di-tert-butyl-9H-carbazole with 3,6-bis(4-(tert-butyl)phenyl)-9H-carbazole, resulting in a pure green emission with high photoluminescence quantum yields (up to 96%). Specifically, OLED based on tPhCzPh3Si exhibited a high external quantum efficiency of 34.6% and a pure green light peaking at 512 nm, with Commission Internationale de l’Eclairage coordinates of (0.14, 0.70).

FullText(HTML)

REFERENCES

[1]	Tang, C.W., and VanSlyke S.A. (1987). Organic electroluminescent diodes. Appl. Phys. Lett. 51: 913−915. DOI: 10.1063/1.98799. View in Article CrossRef Google Scholar
[2]	Zhang, Q., Li, J., Shizu, K., et al. (2012). Design of efficient thermally activated delayed fluorescence materials for pure blue organic light emitting diodes. J. Am. Chem. Soc. 134: 14706−14709. DOI: 10.1021/ja306538w. View in Article CrossRef Google Scholar
[3]	Li, J., Nakagawa, T., MacDonald, J., et al. (2013). Highly efficient organic light-emitting diode based on a hidden thermally activated delayed fluorescence channel in a heptazine derivative. Adv. Mater. 25: 3319−3323. DOI: 10.1002/adma.201300575. View in Article CrossRef Google Scholar
[4]	Tao, Y., Yuan, K., Chen, T., et al. (2014). Thermally activated delayed fluorescence materials towards the breakthrough of organoelectronics. Adv. Mater. 26: 7931−7958. DOI: 10.1002/adma.201402532. View in Article CrossRef Google Scholar
[5]	Zhang, Q., Kuwabara, H., Potscavage, W.J., et al. (2014). Anthraquinone-based intramolecular charge-transfer compounds: computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence. J. Am. Chem. Soc. 136: 18070−18081. DOI: 10.1021/ja510144h. View in Article CrossRef Google Scholar
[6]	Zhang, Q., Li, B., Huang, S., et al. (2014). Efficient blue organic light-emitting diodes employing thermally activated delayed fluorescence. Nat. Photonics. 8: 326−332. DOI: 10.1038/nphoton.2014.12. View in Article CrossRef Google Scholar
[7]	Wu, S., Aonuma, M., Zhang, Q., et al. (2014). High-efficiency deep-blue organic light-emitting diodes based on a thermally activated delayed fluorescence emitter. J. Mater. Chem. C. 2: 421−424. DOI: 10.1039/C3TC31936A. View in Article CrossRef Google Scholar
[8]	Kawasumi, K., Wu, T., Zhu, T., et al. (2015). Thermally activated delayed fluorescence materials based on homoconjugation effect of donor-acceptor triptycenes. J. Am. Chem. Soc. 137: 11908−11911. DOI: 10.1021/jacs.5b07932. View in Article CrossRef Google Scholar
[9]	Noda, H., Nakanotani H., and Adachi C. (2018). Excited state engineering for efficient reverse intersystem crossing. Sci. Adv. 4: eaao6910. DOI: 10.1126/sciadv.aao6910. View in Article CrossRef Google Scholar
[10]	Park, I.S., Matsuo, K., Aizawa, N., et al. (2018). High-performance dibenzoheteraborin-based thermally activated delayed fluorescence emitters: molecular architectonics for concurrently achieving narrowband emission and efficient triplet-singlet spin conversion. Adv. Funct. Mater. 28: 1802031. DOI: 10.1002/adfm.201802031. View in Article CrossRef Google Scholar
[11]	Cui, L.S., Gillett, A.J., Zhang, S.F., et al. (2020). Fast spin-flip enables efficient and stable organic electroluminescence from charge-transfer states. Nat. Photonics. 14: 636−642. DOI: 10.1038/s41566-020-0668-z. View in Article CrossRef Google Scholar
[12]	Wada, Y., Nakagawa, H., Matsumoto, S., et al. (2020). Organic light emitters exhibiting very fast reverse intersystem crossing. Nat. Photonics. 14: 643−649. DOI: 10.1038/s41566-020-0667-0. View in Article CrossRef Google Scholar
[13]	Zhang, D., Song, X., Gillett, A.J., et al. (2020). Efficient and stable deep-blue fluorescent organic light-emitting diodes employing a sensitizer with fast triplet upconversion. Adv. Mater. 32: e1908355. DOI: 10.1002/adma.201908355. View in Article CrossRef Google Scholar
[14]	Wang, H., Xie, L., Peng, Q., et al. (2014). Novel thermally activated delayed fluorescence materials-thioxanthone derivatives and their applications for highly efficient OLEDs. Adv. Mater. 26: 5198−5204. DOI: 10.1002/adma.201401393. View in Article CrossRef Google Scholar
[15]	Luo, X.F., Zhang, L.X., Zheng, Y.X., et al. (2022). Improving reverse intersystem crossing of MR-TADF emitters for OLEDs. J. Semicond. 43: 110202. DOI: 10.1088/1674-4926/43/11/110202. View in Article CrossRef Google Scholar
[16]	Im, Y., Kim, M., Cho, Y.J., et al. (2017). Molecular design strategy of organic thermally activated delayed fluorescence emitters. Chem. Mater. 29: 1946−1963. DOI: 10.1021/acs.chemmater.6b05324. View in Article CrossRef Google Scholar
[17]	Santoro, F., Lami, A., Improta, R., et al. (2008). Effective method for the computation of optical spectra of large molecules at finite temperature including the Duschinsky and Herzberg-Teller effect: the Qx band of porphyrin as a case study. J. Chem. Phys. 128: 224311. DOI: 10.1063/1.2929846. View in Article CrossRef Google Scholar
[18]	Uoyama, H., Goushi, K., Shizu, K., et al. (2012). Highly efficient organic light-emitting diodes from delayed fluorescence. Nature 492: 234−238. DOI: 10.1038/nature11687. View in Article CrossRef Google Scholar
[19]	Komino, T., Tanaka H., and Adachi C., (2014). Selectively controlled orientational order in linear-shaped thermally activated delayed fluorescent dopants. Chem. Mater. 26 : 3665-3671. DOI: 10.1021/cm500802p. View in Article Google Scholar
[20]	Hirata, S., Sakai, Y., Masui, K., et al. (2015). Highly efficient blue electroluminescence based on thermally activated delayed fluorescence. Nat. Mater. 14: 330−336. DOI: 10.1038/nmat4154. View in Article CrossRef Google Scholar
[21]	Cui, L.S., Deng, Y.L., Tsang, D.P., et al. (2016). Controlling synergistic oxidation processes for efficient and stable blue thermally activated delayed fluorescence devices. Adv. Mater. 28: 7620−7625. DOI: 10.1002/adma.201602127. View in Article CrossRef Google Scholar
[22]	Hatakeyama, T., Shiren, K., Nakajima, K., et al. (2016). Ultrapure blue thermally activated delayed fluorescence molecules: efficient HOMO-LUMO separation by the multiple resonance effect. Adv. Mater. 28: 2777−2781. DOI: 10.1002/adma.201505491. View in Article CrossRef Google Scholar
[23]	Xu, Y., Cheng, Z., Li, Z., et al. (2020). Molecular-structure and device-configuration optimizations toward highly efficient green electroluminescence with narrowband emission and high color purity. Adv. Opt.Mater. 8: 1902142. DOI: 10.1002/adom.201902142. View in Article CrossRef Google Scholar
[24]	Yang, M., Park, I.S., and Yasuda T. (2020). Full-color, narrowband, and high-efficiency electroluminescence from boron and carbazole embedded polycyclic heteroaromatics. J. Am. Chem. Soc. 142: 19468−19472. DOI: 10.1021/jacs.0c10081. View in Article CrossRef Google Scholar
[25]	Zhang, Y., Zhang, D., Wei, J., et al. (2019). Multi-resonance induced thermally activated delayed fluorophores for narrowband green OLEDs. Angew.Chem. Int. Ed. 58: 16912−16917. DOI: 10.1002/anie.201911266. View in Article CrossRef Google Scholar
[26]	Matsui, K., Oda, S., Yoshiura, K., et al. (2018). One-shot multiple borylation toward BN-doped nanographenes. J. Am. Chem. Soc. 140: 1195−1198. DOI: 10.1021/jacs.7b10578. View in Article CrossRef Google Scholar
[27]	Suresh, S.M., Duda, E., Hall, D., et al. (2020). A deep blue B,N-doped heptacene emitter that shows both thermally activated delayed fluorescence and delayed fluorescence by triplet-triplet annihilation. J. Am. Chem. Soc. 142: 6588−6599. DOI: 10.1021/jacs.9b13704. View in Article CrossRef Google Scholar
[28]	Tanaka, H., Oda, S., Ricci, G., et al. (2021). Hypsochromic shift of multiple-resonance-induced thermally activated delayed fluorescence by oxygen atom incorporation. Angew. Chem. Int. Ed. 60: 17910−17914. DOI: 10.1002/anie.202105032. View in Article CrossRef Google Scholar
[29]	Yang, M., Shikita, S., Min, H., et al. (2021). Wide-range color tuning of narrowband emission in multi-resonance organoboron delayed fluorescence materials through rational imine/amine functionalization. Angew. Chem. Int. Ed. 60: 23142−23147. DOI: 10.1002/anie.202109335. View in Article CrossRef Google Scholar
[30]	Jiang, P., Miao, J., Cao, X., et al. (2022). Quenching-resistant multiresonance TADF emitter realizes 40% external quantum efficiency in narrowband electroluminescence at high doping level. Adv. Mater. 34: e2106954. DOI: 10.1002/adma.202106954. View in Article CrossRef Google Scholar
[31]	Yan, Z. P., Yuan, L., Zhang, Y., et al. (2022). A chiral dual-core organoboron structure realizes dual-channel enhanced ultrapure blue emission and highly efficient circularly polarized electroluminescence. Adv. Mater. 34: e2204253. DOI: 10.1002/adma.202204253. View in Article CrossRef Google Scholar
[32]	Ikeda, N., Oda, S., Matsumoto, R., et al. (2020). Solution-processable pure green thermally activated delayed fluorescence emitter based on the multiple resonance effect. Adv. Mater. 32: e2004072. DOI: 10.1002/adma.202004072. View in Article CrossRef Google Scholar
[33]	Jiang, P., Zhan, L., Cao, X., et al. (2021). Simple acridan-based multi-resonance structures enable highly efficient narrowband green TADF electroluminescence. Adv. Opt. Mater. 9: 2100825. DOI: 10.1002/adom.202100825. View in Article CrossRef Google Scholar
[34]	Zhang, Y., Li, G., Wang, L., et al. (2022). Fusion of multi-resonance fragment with conventional polycyclic aromatic hydrocarbon for nearly BT.2020 green emission. Angew. Chem. Int. Ed. 61 : e202202380. DOI: 10.1002/anie.202202380. View in Article Google Scholar
[35]	Wu, X., Huang, J.W., Su, B.K., et al. (2022). Fabrication of crcularly polarized MR-TADF emitters with asymmetrical peripheral-lock enhancing helical B/N-doped nanographenes. Adv. Mater. 34: e2105080. DOI: 10.1002/adma.202105080. View in Article CrossRef Google Scholar
[36]	Fan, X.C., Wang, K., Shi, Y.Z., et al. (2023). Ultrapure green organic light-emitting diodes based on highly distorted fused π-conjugated molecular design. Nat. Photonics. 17: 280−285. DOI: 10.1038/s41566-022-01106-8. View in Article CrossRef Google Scholar
[37]	Wang, Q., Xu, Y., Huang, T., et al. (2023). Precisely slight regulation of emission maxima and construction of highly efficient electroluminescent materials with high color purity. Angew. Chem. Int. Ed., 62: e202301930. DOI: 10.1002/anie.202301930. View in Article CrossRef Google Scholar
[38]	Li, J.K., Chen, X.Y., Guo, Y.L., et al. (2021). B,N-embedded double hetero[7]helicenes with strong chiroptical responses in the visible light region. J. Am. Chem. Soc. 143: 17958−17963. DOI: 10.1021/jacs.1c09058. View in Article CrossRef Google Scholar
[39]	Zhang, Y., Zhang, D., Huang, T., et al. (2021). Multi-resonance deep-red emitters with shallow potential-energy surfaces to surpass energy-gap law. Angew.Chem. Int. Ed. 60: 20498−20503. DOI: 10.1002/anie.202107848. View in Article CrossRef Google Scholar
[40]	Liu, Y., Xiao, X., Ran, Y., et al. (2021). Molecular design of thermally activated delayed fluorescent emitters for narrowband orange-red OLEDs boosted by a cyano-functionalization strategy. Chem. Sci. 12: 9408−9412. DOI: 10.1039/D1SC02042K. View in Article CrossRef Google Scholar
[41]	Zou, Y., Hu, J., Yu, M., et al. (2022). High performance narrowband pure-red OLEDs with external quantum efficiencies up to 36.1% and ultra-low efficiency roll-off. Adv. Mater. 34 : 2201442. DOI: 10.1002/adma.202201442. View in Article Google Scholar
[42]	Cheng, Y.C., Fan, X.C., Huang, F., et al. (2022). A highly twisted carbazole-fused DABNA derivative as an orange-red TADF emitter for OLEDs with nearly 40% EQE. Angew. Chem. Int. Ed. 61: e202212575. DOI: 10.1002/anie.202212575. View in Article CrossRef Google Scholar
[43]	Xu, Y., Li, C., Li, Z., et al. (2022). Highly efficient electroluminescent materials with high color purity based on strong acceptor attachment onto B–N-containing multiple resonance frameworks. CCS Chemistry. 4: 2065−2079. DOI: 10.31635/ccschem.021.202101033. View in Article CrossRef Google Scholar
[44]	Zhang, Y., Zhang, D., Wei, J., et al. (2020). Achieving pure green electroluminescence with CIEy of 0.69 and EQE of 28.2% from an aza-fused multi-resonance emitter. Angew. Chem. Int. Ed. 59 : 17499-17503. DOI: 10.1002/anie.202008264. View in Article Google Scholar
[45]	Luo, X.F., Song, S.Q., Ni, H.X., et al. (2022). Multiple-resonance-induced thermally activated delayed fluorescence materials based on indolo[3,2,1-jk]carbazole with an efficient narrowband pure-green electroluminescence. Angew. Chem. Int. Ed. 61: e202209984. DOI: 10.1002/anie.202209984. View in Article CrossRef Google Scholar
[46]	Rothe, C., King, S.M., and Monkman A.P. (2006). Direct measurement of the singlet generation yield in polymer light-emitting diodes. Phys. Rev. Lett. 97: 076602. DOI: 10.1103/PhysRevLett.97.076602. View in Article CrossRef Google Scholar
[47]	Notsuka, N., Kabe, R., Goushi, K., et al. (2017). Confinement of long-lived triplet excitons in organic semiconducting host-guest systems. Adv. Funct. Mater. 27: 1703902. DOI: 10.1002/adfm.201703902. View in Article CrossRef Google Scholar
[48]	Lee, K.H., and Lee J.Y. (2019). Paradigm change of blue emitters: thermally activated fluorescence emitters as long-living fluorescence emitters by triplet exciton quenching. Org. Electron. 75: 105377. DOI: 10.1016/j.orgel.2019.105377. View in Article CrossRef Google Scholar
[49]	Smit, J.H., van der Velde, J.H.M., Huang, J., et al. (2019). On the impact of competing intra- and intermolecular triplet-state quenching on photobleaching and photoswitching kinetics of organic fluorophores. Phys. Chem. Chem. Phys. 21: 3721−3733. DOI: 10.1039/C8CP05063E. View in Article CrossRef Google Scholar
[50]	Zhang, Y., Wei, J., Zhang, D., et al. (2022). Sterically wrapped multiple resonance fluorophors for suppression of concentration quenching and spectrum broadening. Angew. Chem. Int. Ed. 61: e202113206. DOI: 10.1002/anie.202113206. View in Article CrossRef Google Scholar
[51]	Liao, X.J., Pu, D., Yuan, L., et al. (2023). Planar chiral multiple resonance thermally activated delayed fluorescence materials for efficient circularly polarized electroluminescence. Angew. Chem. Int. Ed. 62: e202217045. DOI: 10.1002/anie.202217045. View in Article CrossRef Google Scholar

CITED BY

ABOUT THIS ARTICLE

Cite this article:

Ni H., Sun W., Luo X., et al., (2023). Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units. The Innovation Materials 1(3), 100041. https://doi.org/10.59717/j.xinn-mater.2023.100041

Ni H., Sun W., Luo X., et al., (2023). Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units. The Innovation Materials 1(3), 100041. https://doi.org/10.59717/j.xinn-mater.2023.100041

Standard PDF

Extended PDF

Figures(6) Tables(2)

Article Metrics

Article views(3620) PDF downloads(970) Cited by(0)

Relative Articles

Article Contents

ABOUT THIS ARTICLE

Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units

GRAPHICAL ABSTRACT

PUBLIC SUMMARY

ABSTRACT

REFERENCES

ABOUT THIS ARTICLE

Cite this article:

Share

Article Metrics

Relative Articles

Catalog

{{newsColumn.name}}

Journal links

{{newsColumn.name}}

Stay connected

Peripherally non-planar multiple resonance induced thermally activated delayed fluorescence materials containing silyl units

GRAPHICAL ABSTRACT

PUBLIC SUMMARY

ABSTRACT

REFERENCES

ABOUT THIS ARTICLE

Cite this article:

Share

Article Metrics

Relative Articles

Catalog

Export File

Citation

Format

Content

{{newsColumn.name}}

Journal links

{{newsColumn.name}}

Stay connected