Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields

Dongyang Chen; Yu Kusakabe; Yongxia Ren; Dianming Sun; Pachaiyappan Rajamalli; Yoshimasa Wada; Katsuaki Suzuki; Hironori Kaji; Eli Zysman-Colman

doi:10.1021/acs.joc.1c01101

Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields

Dongyang Chen, Yu Kusakabe, Yongxia Ren, Dianming Sun, Pachaiyappan Rajamalli, Yoshimasa Wada, Katsuaki Suzuki, Hironori Kaji, Eli Zysman-Colman

Research output: Contribution to journal › Article › peer-review

Abstract

Three multichromophore thermally activated delayed fluorescence (TADF) molecules, p-di2CzPN, m-di2CzPN, and 1,3,5-tri2CzPN, were synthesized and characterized. These molecules were designed by connecting the TADF moiety 4,5-di(9H-carbazol-9- yl)phthalonitrile (2CzPN) to different positions of a central benzene ring scaffold. Three highly soluble emitters all exhibited near quantitative photoluminescence quantum yields (Φ_PL) in toluene. High Φ_PLs were also achieved in doped films, 59% and 70% for p-di2CzPN and m-di2CzPN in 10 wt% DPEPO doped films, respectively, and 54% for 1,3,5-tri2CzPN in 20 wt% doped CBP film. The rate constant of reverse intersystem crossing (k_RISC) for p-di2CzPN and m-di2CzPN in DPEPO films reached 1.1×10⁵ and 0.7×10⁵ s⁻¹, respectively, and k_RISC for 1,3,5-tri2CzPN in CBP film reached 1.7×10⁵ s⁻¹. A solution-processed organic light-emitting diode based on 1,3,5-tri2CzPN exhibited a sky-blue emission with CIE coordinate of (0.22, 0.44), and achieved a maximum external quantum efficiency of 7.1%.

Original language	English
Journal	The Journal of Organic Chemistry
Volume	Articles ASAP
Early online date	29 Jul 2021
DOIs	https://doi.org/10.1021/acs.joc.1c01101
Publication status	E-pub ahead of print - 29 Jul 2021

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10.1021/acs.joc.1c01101

Chen_2021_JoOC_Multichoromophore_molecular_AAM
Copyright © 2021 American Chemical Society. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.joc.1c01101
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Chen, D., Kusakabe, Y., Ren, Y., Sun, D., Rajamalli, P., Wada, Y., Suzuki, K., Kaji, H., & Zysman-Colman, E. (2021). Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields. The Journal of Organic Chemistry, Articles ASAP. Advance online publication. https://doi.org/10.1021/acs.joc.1c01101

@article{0bc53ed60ea3464981f72cce52caa715,

title = "Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields",

abstract = "Three multichromophore thermally activated delayed fluorescence (TADF) molecules, p-di2CzPN, m-di2CzPN, and 1,3,5-tri2CzPN, were synthesized and characterized. These molecules were designed by connecting the TADF moiety 4,5-di(9H-carbazol-9- yl)phthalonitrile (2CzPN) to different positions of a central benzene ring scaffold. Three highly soluble emitters all exhibited near quantitative photoluminescence quantum yields (ΦPL) in toluene. High ΦPLs were also achieved in doped films, 59% and 70% for p-di2CzPN and m-di2CzPN in 10 wt% DPEPO doped films, respectively, and 54% for 1,3,5-tri2CzPN in 20 wt% doped CBP film. The rate constant of reverse intersystem crossing (kRISC) for p-di2CzPN and m-di2CzPN in DPEPO films reached 1.1×105 and 0.7×105 s−1, respectively, and kRISC for 1,3,5-tri2CzPN in CBP film reached 1.7×105 s−1. A solution-processed organic light-emitting diode based on 1,3,5-tri2CzPN exhibited a sky-blue emission with CIE coordinate of (0.22, 0.44), and achieved a maximum external quantum efficiency of 7.1%.",

author = "Dongyang Chen and Yu Kusakabe and Yongxia Ren and Dianming Sun and Pachaiyappan Rajamalli and Yoshimasa Wada and Katsuaki Suzuki and Hironori Kaji and Eli Zysman-Colman",

note = "D.C thanks the China Scholarship Council (201603780001). P. R acknowledges support from a Marie Sk{\l}odowska-Curie Individual Fellowship (No. 749557). D. S. acknowledges support from the Marie Sk{\l}odowska-Curie Individual Fellowship (No. 838009). We acknowledge support from the Engineering and Physical Sciences Research Council of the United Kingdom (grant EP/P010482/1), from the International Collaborative Research Program of Institute for Chemical Research, Kyoto University (Nos. 2020-37 and 2021-37), and from JSPS KAKENHI Grant Number JP20H05840 (Grant-in-Aid for Transformative Research Areas, “Dynamic Exciton”).",

year = "2021",

month = jul,

day = "29",

doi = "10.1021/acs.joc.1c01101",

language = "English",

volume = "Articles ASAP",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields

AU - Chen, Dongyang

AU - Kusakabe, Yu

AU - Ren, Yongxia

AU - Sun, Dianming

AU - Rajamalli, Pachaiyappan

AU - Wada, Yoshimasa

AU - Suzuki, Katsuaki

AU - Kaji, Hironori

AU - Zysman-Colman, Eli

N1 - D.C thanks the China Scholarship Council (201603780001). P. R acknowledges support from a Marie Skłodowska-Curie Individual Fellowship (No. 749557). D. S. acknowledges support from the Marie Skłodowska-Curie Individual Fellowship (No. 838009). We acknowledge support from the Engineering and Physical Sciences Research Council of the United Kingdom (grant EP/P010482/1), from the International Collaborative Research Program of Institute for Chemical Research, Kyoto University (Nos. 2020-37 and 2021-37), and from JSPS KAKENHI Grant Number JP20H05840 (Grant-in-Aid for Transformative Research Areas, “Dynamic Exciton”).

PY - 2021/7/29

Y1 - 2021/7/29

N2 - Three multichromophore thermally activated delayed fluorescence (TADF) molecules, p-di2CzPN, m-di2CzPN, and 1,3,5-tri2CzPN, were synthesized and characterized. These molecules were designed by connecting the TADF moiety 4,5-di(9H-carbazol-9- yl)phthalonitrile (2CzPN) to different positions of a central benzene ring scaffold. Three highly soluble emitters all exhibited near quantitative photoluminescence quantum yields (ΦPL) in toluene. High ΦPLs were also achieved in doped films, 59% and 70% for p-di2CzPN and m-di2CzPN in 10 wt% DPEPO doped films, respectively, and 54% for 1,3,5-tri2CzPN in 20 wt% doped CBP film. The rate constant of reverse intersystem crossing (kRISC) for p-di2CzPN and m-di2CzPN in DPEPO films reached 1.1×105 and 0.7×105 s−1, respectively, and kRISC for 1,3,5-tri2CzPN in CBP film reached 1.7×105 s−1. A solution-processed organic light-emitting diode based on 1,3,5-tri2CzPN exhibited a sky-blue emission with CIE coordinate of (0.22, 0.44), and achieved a maximum external quantum efficiency of 7.1%.

AB - Three multichromophore thermally activated delayed fluorescence (TADF) molecules, p-di2CzPN, m-di2CzPN, and 1,3,5-tri2CzPN, were synthesized and characterized. These molecules were designed by connecting the TADF moiety 4,5-di(9H-carbazol-9- yl)phthalonitrile (2CzPN) to different positions of a central benzene ring scaffold. Three highly soluble emitters all exhibited near quantitative photoluminescence quantum yields (ΦPL) in toluene. High ΦPLs were also achieved in doped films, 59% and 70% for p-di2CzPN and m-di2CzPN in 10 wt% DPEPO doped films, respectively, and 54% for 1,3,5-tri2CzPN in 20 wt% doped CBP film. The rate constant of reverse intersystem crossing (kRISC) for p-di2CzPN and m-di2CzPN in DPEPO films reached 1.1×105 and 0.7×105 s−1, respectively, and kRISC for 1,3,5-tri2CzPN in CBP film reached 1.7×105 s−1. A solution-processed organic light-emitting diode based on 1,3,5-tri2CzPN exhibited a sky-blue emission with CIE coordinate of (0.22, 0.44), and achieved a maximum external quantum efficiency of 7.1%.

UR - https://doi.org/10.26434/chemrxiv.14560860.v1

U2 - 10.1021/acs.joc.1c01101

DO - 10.1021/acs.joc.1c01101

M3 - Article

SN - 0022-3263

VL - Articles ASAP

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

ER -

Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields

Abstract

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Other files and links

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H2020 MSCA IF 2018 (Dianming Sun): H2020 MSCA IF 2018 (Dianming Sun)

TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs

DENTADFE: DENTADFE

Multichromophore Molecular Design for Thermally Activated Delayed Fluorescence Emitters with Near-Unity Photoluminescence Quantum Yields (dataset)

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Multichromophore molecular design for efficient thermally activated delayed-fluorescence emitters with near-unity photoluminescence quantum yields

Abstract

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Other files and links

Fingerprint

Projects

H2020 MSCA IF 2018 (Dianming Sun): H2020 MSCA IF 2018 (Dianming Sun)

TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs

DENTADFE: DENTADFE

Datasets

Multichromophore Molecular Design for Thermally Activated Delayed Fluorescence Emitters with Near-Unity Photoluminescence Quantum Yields (dataset)

Cite this