[2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes

Yan Xu; Hassan Hafeez; Jasmin Seibert; Sen Wu; Jhon Sebastian Oviedo Ortiz; Jeanne Crassous; Stefan Bräse; Ifor D. W. Samuel; Eli Zysman-Colman

doi:10.1002/adfm.202402036

[2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes

Yan Xu, Hassan Hafeez, Jasmin Seibert, Sen Wu, Jhon Sebastian Oviedo Ortiz, Jeanne Crassous, Stefan Bräse, Ifor D. W. Samuel^*, Eli Zysman-Colman^*

^*Corresponding author for this work

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

1 Citation (Scopus)

27 Downloads (Pure)

Abstract

The study reports two pairs of chiral multi-resonant thermally activated delayed fluorescence (MR-TADF) materials PCP-DiKTa and Czp-DiKTa by decorating a known MR-TADF core, DiKTa, with different [2.2]paracyclophane (PCP) based planar chiral groups. PCP-DiKTa shows narrow sky-blue emission with a full width at half maximum (FWHM) of 44 nm, while the emission of Czp-DiKTa is slightly broader with a FWHM of 66 nm and redshifted. Both emitters show high photoluminescence quantum yields of 93 and 99% for PCP-DiKTa and Czp-DiKTa, respectively. Enantiomerically pure samples of both compounds show chiroptical properties in the ground state while only Czp-DiKTa exhibits chiroptical activity in the excited state, with dissymmetry factors (|g_PL|) of 4 × 10⁻⁴. Organic light-emitting diodes (OLEDs) with PCP-DiKTa and Czp-DiKTa show maximum external quantum efficiencies (EQE_max) of 25.7 and 29.2%, with λ_ELof 489 and 518 nm, and FWHMs of 53 and 69 nm, respectively. These EQE_max values are higher than those of other reported devices employing PCP-based D-A type emitters. This work demonstrates that the PCP moiety is not only a powerful building block to develop planar chiral emitters but one that is compatible with the fabrication of high efficiency devices.

Original language	English
Number of pages	9
Journal	Advanced Functional Materials
Volume	Early View
Early online date	21 Mar 2024
DOIs	https://doi.org/10.1002/adfm.202402036
Publication status	E-pub ahead of print - 21 Mar 2024

Keywords

[2.2]Paracyclophane
Circularly polarized luminescence
Multiresonant thermally activated delayed fluorescence
Organic light-emitting diodes

Access to Document

10.1002/adfm.202402036Licence: CC BY

Xu_2024_AFM_2.2Paracyclophane-substituted-chiral_CC
Copyright © 2024 The Authors. Advanced Functional Materials published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 4.26 MBLicence: CC BY

Cite this

Xu, Y., Hafeez, H., Seibert, J., Wu, S., Ortiz, J. S. O., Crassous, J., Bräse, S., Samuel, I. D. W., & Zysman-Colman, E. (2024). [2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes. Advanced Functional Materials, Early View. Advance online publication. https://doi.org/10.1002/adfm.202402036

@article{3bc69b59ec30438a9b5f7e2ade529b40,

title = "[2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes",

abstract = "The study reports two pairs of chiral multi-resonant thermally activated delayed fluorescence (MR-TADF) materials PCP-DiKTa and Czp-DiKTa by decorating a known MR-TADF core, DiKTa, with different [2.2]paracyclophane (PCP) based planar chiral groups. PCP-DiKTa shows narrow sky-blue emission with a full width at half maximum (FWHM) of 44 nm, while the emission of Czp-DiKTa is slightly broader with a FWHM of 66 nm and redshifted. Both emitters show high photoluminescence quantum yields of 93 and 99% for PCP-DiKTa and Czp-DiKTa, respectively. Enantiomerically pure samples of both compounds show chiroptical properties in the ground state while only Czp-DiKTa exhibits chiroptical activity in the excited state, with dissymmetry factors (|gPL|) of 4 × 10−4. Organic light-emitting diodes (OLEDs) with PCP-DiKTa and Czp-DiKTa show maximum external quantum efficiencies (EQEmax) of 25.7 and 29.2%, with λEL of 489 and 518 nm, and FWHMs of 53 and 69 nm, respectively. These EQEmax values are higher than those of other reported devices employing PCP-based D-A type emitters. This work demonstrates that the PCP moiety is not only a powerful building block to develop planar chiral emitters but one that is compatible with the fabrication of high efficiency devices.",

keywords = "[2.2]Paracyclophane, Circularly polarized luminescence, Multiresonant thermally activated delayed fluorescence, Organic light-emitting diodes",

author = "Yan Xu and Hassan Hafeez and Jasmin Seibert and Sen Wu and Ortiz, {Jhon Sebastian Oviedo} and Jeanne Crassous and Stefan Br{\"a}se and Samuel, {Ifor D. W.} and Eli Zysman-Colman",

note = "The authors aregrateful to the EPSRC for financial support (grant EP/W0151371/1and EP/W007517/1). Y.X. thanks the China Scholarship Council(202106310038) for support. J.S. thanks the J{\"u}rgen Manchot Foundation, the Karlsruhe School of Optics and Photonics, and Dr. Erik Strandberg and Bianca Posselt, for their help in ECD measurements.The authors thank the European Commission Research ExecutiveAgency (Grant Agreement number: 101073045−TADFsolutions−HORIZON-MSCA-2021-DN) and the EPSRC (EP/X026175/1) for financial support. The authors acknowledge the Minist{\`e}re de l{\textquoteright}EnseignementSup{\'e}rieur et de la Recherche and the Centre National de la RechercheScientifique (CNRS).",

year = "2024",

month = mar,

day = "21",

doi = "10.1002/adfm.202402036",

language = "English",

volume = "Early View",

journal = "Advanced Functional Materials",

issn = "1616-301X",

publisher = "John Wiley & Sons, Ltd",

}

TY - JOUR

T1 - [2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes

AU - Xu, Yan

AU - Hafeez, Hassan

AU - Seibert, Jasmin

AU - Wu, Sen

AU - Ortiz, Jhon Sebastian Oviedo

AU - Crassous, Jeanne

AU - Bräse, Stefan

AU - Samuel, Ifor D. W.

AU - Zysman-Colman, Eli

N1 - The authors aregrateful to the EPSRC for financial support (grant EP/W0151371/1and EP/W007517/1). Y.X. thanks the China Scholarship Council(202106310038) for support. J.S. thanks the Jürgen Manchot Foundation, the Karlsruhe School of Optics and Photonics, and Dr. Erik Strandberg and Bianca Posselt, for their help in ECD measurements.The authors thank the European Commission Research ExecutiveAgency (Grant Agreement number: 101073045−TADFsolutions−HORIZON-MSCA-2021-DN) and the EPSRC (EP/X026175/1) for financial support. The authors acknowledge the Ministère de l’EnseignementSupérieur et de la Recherche and the Centre National de la RechercheScientifique (CNRS).

PY - 2024/3/21

Y1 - 2024/3/21

N2 - The study reports two pairs of chiral multi-resonant thermally activated delayed fluorescence (MR-TADF) materials PCP-DiKTa and Czp-DiKTa by decorating a known MR-TADF core, DiKTa, with different [2.2]paracyclophane (PCP) based planar chiral groups. PCP-DiKTa shows narrow sky-blue emission with a full width at half maximum (FWHM) of 44 nm, while the emission of Czp-DiKTa is slightly broader with a FWHM of 66 nm and redshifted. Both emitters show high photoluminescence quantum yields of 93 and 99% for PCP-DiKTa and Czp-DiKTa, respectively. Enantiomerically pure samples of both compounds show chiroptical properties in the ground state while only Czp-DiKTa exhibits chiroptical activity in the excited state, with dissymmetry factors (|gPL|) of 4 × 10−4. Organic light-emitting diodes (OLEDs) with PCP-DiKTa and Czp-DiKTa show maximum external quantum efficiencies (EQEmax) of 25.7 and 29.2%, with λEL of 489 and 518 nm, and FWHMs of 53 and 69 nm, respectively. These EQEmax values are higher than those of other reported devices employing PCP-based D-A type emitters. This work demonstrates that the PCP moiety is not only a powerful building block to develop planar chiral emitters but one that is compatible with the fabrication of high efficiency devices.

AB - The study reports two pairs of chiral multi-resonant thermally activated delayed fluorescence (MR-TADF) materials PCP-DiKTa and Czp-DiKTa by decorating a known MR-TADF core, DiKTa, with different [2.2]paracyclophane (PCP) based planar chiral groups. PCP-DiKTa shows narrow sky-blue emission with a full width at half maximum (FWHM) of 44 nm, while the emission of Czp-DiKTa is slightly broader with a FWHM of 66 nm and redshifted. Both emitters show high photoluminescence quantum yields of 93 and 99% for PCP-DiKTa and Czp-DiKTa, respectively. Enantiomerically pure samples of both compounds show chiroptical properties in the ground state while only Czp-DiKTa exhibits chiroptical activity in the excited state, with dissymmetry factors (|gPL|) of 4 × 10−4. Organic light-emitting diodes (OLEDs) with PCP-DiKTa and Czp-DiKTa show maximum external quantum efficiencies (EQEmax) of 25.7 and 29.2%, with λEL of 489 and 518 nm, and FWHMs of 53 and 69 nm, respectively. These EQEmax values are higher than those of other reported devices employing PCP-based D-A type emitters. This work demonstrates that the PCP moiety is not only a powerful building block to develop planar chiral emitters but one that is compatible with the fabrication of high efficiency devices.

KW - [2.2]Paracyclophane

KW - Circularly polarized luminescence

KW - Multiresonant thermally activated delayed fluorescence

KW - Organic light-emitting diodes

UR - https://doi.org/10.26434/chemrxiv-2024-ds8tw

U2 - 10.1002/adfm.202402036

DO - 10.1002/adfm.202402036

M3 - Article

SN - 1616-301X

VL - Early View

JO - Advanced Functional Materials

JF - Advanced Functional Materials

ER -

[2.2]Paracyclophane-substituted chiral multiresonant thermally activated delayed fluorescence emitters for efficient organic light-emitting diodes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Allan Watson Programme Grant: Boron: Beyond the Reagent

TADF Solutions: TADF SOLUTIONS: addressing the challenges of high-performance solution-processed OLEDs using sustainable materials