Fast delayed emission in new pyridazine-based compounds

Simonas Krotkus; Tomas Matulaitis; Stefan Diesing; Graeme Jeffrey Copley; Emily Archer; Changmin Keum; David Bradford Cordes; Alexandra Martha Zoya Slawin; Malte Christian Gather; Eli Zysman-Colman; Ifor David William Samuel

doi:10.3389/fchem.2020.572862

Fast delayed emission in new pyridazine-based compounds

Simonas Krotkus, Tomas Matulaitis, Stefan Diesing, Graeme Jeffrey Copley, Emily Archer, Changmin Keum, David Bradford Cordes, Alexandra Martha Zoya Slawin, Malte Christian Gather, Eli Zysman-Colman, Ifor David William Samuel

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Abstract

Three novel donor-acceptor molecules comprising the underexplored pyridazine (Pydz) acceptor moiety have been synthesized and their structural, electrochemical and photophysical properties thoroughly characterized. Combining Pydz with two phenoxazine donor units linked via a phenyl bridge in a meta configuration (dPXZMePydz) leads to high reverse intersystem crossing rate k_rISC = 3.9 ∙ 10⁶ s^-1 and fast thermally activated delayed fluorescence (TADF) with <500 ns delayed emission lifetime. Efficient triplet harvesting via the TADF mechanism is demonstrated in OLEDs using dPXZMePydz as the emitter but does not occur for compounds bearing weaker donor units.

Original language	English
Article number	572862
Journal	Frontiers in Chemistry
Volume	8
DOIs	https://doi.org/10.3389/fchem.2020.572862
Publication status	Published - 7 Jan 2021

Keywords

Thermally activated delayed fluorescence (TADF)
Pyridazine
Organic light emission device (OLED)
Reverse intersystem crossing (RISC)
Donor-Acceptor (D-A) architecture

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10.3389/fchem.2020.572862Licence: CC BY

Krotkus_2021_FC_Fastdelayed_CC
Copyright © 2021 Krotkus, Matulaitis, Diesing, Copley, Archer, Keum, Cordes, Slawin, Gather, Zysman-Colman and Samuel. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
Final published version, 2.16 MBLicence: CC BY

Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application
Zysman-Colman, E. (PI)
1/08/18 → 31/01/24
Project: Standard
H2020-MSCA-redTADF: H2020 MSCA IF 2017 (Graeme Copley)
Zysman-Colman, E. (PI)
European Commission
1/04/18 → 31/03/20
Project: Fellowship
TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs
Zysman-Colman, E. (PI)
EPSRC
1/03/17 → 31/03/21
Project: Standard

CCDC 2002948 - 2002949: Experimental Crystal Structure Determination
Krotkus, S. (Creator), Matulaitis, T. (Creator), Diesing, S. (Creator), Copley, G. (Creator), Archer, E. (Creator), Keum, C. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Gather, M. C. (Creator), Zysman-Colman, E. (Creator) & Samuel, I. D. W. (Creator), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc25777x, https://dx.doi.org/10.5517/ccdc.csd.cc25778y
Dataset
Fast Delayed Emission in New Pyridazine-based Compounds (dataset)
Krotkus, S. (Creator), Matulaitis, T. (Creator), Diesing, S. (Creator), Copley, G. J. (Creator), Archer, E. (Creator), Keum, C. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Gather, M. C. (Creator), Zysman-Colman, E. (Creator) & Samuel, I. D. W. (Creator), University of St Andrews, 17 Dec 2020
DOI: 10.17630/3f2695c7-e6d5-4e11-a0b1-dcf1a54d4bb5
Dataset

File

Cite this

@article{e394f78f6ddf4df6ab8d36b0596a80ad,

title = "Fast delayed emission in new pyridazine-based compounds",

abstract = "Three novel donor-acceptor molecules comprising the underexplored pyridazine (Pydz) acceptor moiety have been synthesized and their structural, electrochemical and photophysical properties thoroughly characterized. Combining Pydz with two phenoxazine donor units linked via a phenyl bridge in a meta configuration (dPXZMePydz) leads to high reverse intersystem crossing rate krISC = 3.9 ∙ 106 s-1 and fast thermally activated delayed fluorescence (TADF) with <500 ns delayed emission lifetime. Efficient triplet harvesting via the TADF mechanism is demonstrated in OLEDs using dPXZMePydz as the emitter but does not occur for compounds bearing weaker donor units.",

keywords = "Thermally activated delayed fluorescence (TADF), Pyridazine, Organic light emission device (OLED), Reverse intersystem crossing (RISC), Donor-Acceptor (D-A) architecture",

author = "Simonas Krotkus and Tomas Matulaitis and Stefan Diesing and Copley, {Graeme Jeffrey} and Emily Archer and Changmin Keum and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Gather, {Malte Christian} and Eli Zysman-Colman and Samuel, {Ifor David William}",

note = "We thank the EPSRC for financial support (grants EP/P010482/1 and EP/R035164/1). We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analytical services. G.C. acknowledges funding by the European Commission through a Marie Sk{\l}odowska Individual Fellowship (No. 799302). C.K. acknowledges support from the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1A6A3A03012331).",

year = "2021",

month = jan,

day = "7",

doi = "10.3389/fchem.2020.572862",

language = "English",

volume = "8",

journal = "Frontiers in Chemistry",

issn = "2296-2646",

publisher = "Frontiers Media S. A.",

}

TY - JOUR

T1 - Fast delayed emission in new pyridazine-based compounds

AU - Krotkus, Simonas

AU - Matulaitis, Tomas

AU - Diesing, Stefan

AU - Copley, Graeme Jeffrey

AU - Archer, Emily

AU - Keum, Changmin

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Gather, Malte Christian

AU - Zysman-Colman, Eli

AU - Samuel, Ifor David William

N1 - We thank the EPSRC for financial support (grants EP/P010482/1 and EP/R035164/1). We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analytical services. G.C. acknowledges funding by the European Commission through a Marie Skłodowska Individual Fellowship (No. 799302). C.K. acknowledges support from the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1A6A3A03012331).

PY - 2021/1/7

Y1 - 2021/1/7

N2 - Three novel donor-acceptor molecules comprising the underexplored pyridazine (Pydz) acceptor moiety have been synthesized and their structural, electrochemical and photophysical properties thoroughly characterized. Combining Pydz with two phenoxazine donor units linked via a phenyl bridge in a meta configuration (dPXZMePydz) leads to high reverse intersystem crossing rate krISC = 3.9 ∙ 106 s-1 and fast thermally activated delayed fluorescence (TADF) with <500 ns delayed emission lifetime. Efficient triplet harvesting via the TADF mechanism is demonstrated in OLEDs using dPXZMePydz as the emitter but does not occur for compounds bearing weaker donor units.

AB - Three novel donor-acceptor molecules comprising the underexplored pyridazine (Pydz) acceptor moiety have been synthesized and their structural, electrochemical and photophysical properties thoroughly characterized. Combining Pydz with two phenoxazine donor units linked via a phenyl bridge in a meta configuration (dPXZMePydz) leads to high reverse intersystem crossing rate krISC = 3.9 ∙ 106 s-1 and fast thermally activated delayed fluorescence (TADF) with <500 ns delayed emission lifetime. Efficient triplet harvesting via the TADF mechanism is demonstrated in OLEDs using dPXZMePydz as the emitter but does not occur for compounds bearing weaker donor units.

KW - Thermally activated delayed fluorescence (TADF)

KW - Pyridazine

KW - Organic light emission device (OLED)

KW - Reverse intersystem crossing (RISC)

KW - Donor-Acceptor (D-A) architecture

U2 - 10.3389/fchem.2020.572862

DO - 10.3389/fchem.2020.572862

M3 - Article

SN - 2296-2646

VL - 8

JO - Frontiers in Chemistry

JF - Frontiers in Chemistry

M1 - 572862

ER -

Fast delayed emission in new pyridazine-based compounds

Abstract

Keywords

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Projects

Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application

H2020-MSCA-redTADF: H2020 MSCA IF 2017 (Graeme Copley)

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

Datasets

CCDC 2002948 - 2002949: Experimental Crystal Structure Determination

Fast Delayed Emission in New Pyridazine-based Compounds (dataset)

Cite this