Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications

Chenfei Li; Campbell Frank Ross Mackenzie; Said A. Said; Amlan Kumar Pal; Mohammed A. Haghighatbin; Azin Babaei; Michele Sessolo; David Bradford Cordes; Alexandra Martha Zoya Slawin; Paul C J Kamer; Henk Bolink; Conor F. Hogan; Eli Zysman-Colman

doi:10.1021/acs.inorgchem.1c00804

Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications

Chenfei Li, Campbell Frank Ross Mackenzie, Said A. Said, Amlan Kumar Pal, Mohammed A. Haghighatbin, Azin Babaei, Michele Sessolo, David Bradford Cordes, Alexandra Martha Zoya Slawin, Paul C J Kamer, Henk Bolink, Conor F. Hogan, Eli Zysman-Colman

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

Abstract

We report a series of seven cationic heteroleptic copper(I) complexes of the form [Cu(P^P)(dmphen)]BF₄, where dmphen is 2,9-dimethyl-1,10-phenanthroline and P^P is a diphosphine chelate, in which the effect of the bite angle of the diphosphine ligand on the photophysical properties of the complexes was studied. Several of the complexes exhibit moderately high photoluminescence quantum yields in the solid state, with Φ_PL of up to 35%, and in solution, with Φ_PL of up to 98%. We were able to correlate the powder photoluminescence quantum yields with the % V_bur of the P^P ligand. The most emissive complexes were used to fabricate both organic light-emitting diodes and light-emitting electrochemical cells (LECs), both of which showed moderate performance. Compared to the benchmark copper(I)-based LECs, [Cu(dnbp)(DPEPhos)]⁺ (maximum external quantum efficiency, EQE_max = 16%), complex 3 (EQE_max = 1.85%) showed a much longer device lifetime (t_1/2 = 1.25 h and >16.5 h for [Cu(dnbp)(DPEPhos)]⁺ and complex 3, respectively). The electrochemiluminescence (ECL) properties of several complexes were also studied, which, to the best of our knowledge, constitutes the first ECL study for heteroleptic copper(I) complexes. Notably, complexes exhibiting more reversible electrochemistry were associated with higher annihilation ECL as well as better performance in a LEC.

Original language	English
Number of pages	17
Journal	Inorganic Chemistry
Volume	Articles ASAP
Early online date	1 Jul 2021
DOIs	https://doi.org/10.1021/acs.inorgchem.1c00804
Publication status	E-pub ahead of print - 1 Jul 2021

Keywords

Redox reactions
Ligands
Crystal structure
Organophosphorus compounds
Nuclear magnetic resonance spectroscopy

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10.1021/acs.inorgchem.1c00804

Cu-xantphos-manuscript ver 38
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.inorgchem.1c00804
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Li, C., Mackenzie, C. F. R., Said, S. A., Pal, A. K., Haghighatbin, M. A., Babaei, A., Sessolo, M., Cordes, D. B., Slawin, A. M. Z., Kamer, P. C. J., Bolink, H., Hogan, C. F., & Zysman-Colman, E. (2021). Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications. Inorganic Chemistry, Articles ASAP. Advance online publication. https://doi.org/10.1021/acs.inorgchem.1c00804

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title = "Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications",

abstract = "We report a series of seven cationic heteroleptic copper(I) complexes of the form [Cu(P^P)(dmphen)]BF4, where dmphen is 2,9-dimethyl-1,10-phenanthroline and P^P is a diphosphine chelate, in which the effect of the bite angle of the diphosphine ligand on the photophysical properties of the complexes was studied. Several of the complexes exhibit moderately high photoluminescence quantum yields in the solid state, with ΦPL of up to 35%, and in solution, with ΦPL of up to 98%. We were able to correlate the powder photoluminescence quantum yields with the % Vbur of the P^P ligand. The most emissive complexes were used to fabricate both organic light-emitting diodes and light-emitting electrochemical cells (LECs), both of which showed moderate performance. Compared to the benchmark copper(I)-based LECs, [Cu(dnbp)(DPEPhos)]+ (maximum external quantum efficiency, EQEmax = 16%), complex 3 (EQEmax = 1.85%) showed a much longer device lifetime (t1/2 = 1.25 h and >16.5 h for [Cu(dnbp)(DPEPhos)]+ and complex 3, respectively). The electrochemiluminescence (ECL) properties of several complexes were also studied, which, to the best of our knowledge, constitutes the first ECL study for heteroleptic copper(I) complexes. Notably, complexes exhibiting more reversible electrochemistry were associated with higher annihilation ECL as well as better performance in a LEC.",

keywords = "Redox reactions, Ligands, Crystal structure, Organophosphorus compounds, Nuclear magnetic resonance spectroscopy",

author = "Chenfei Li and Mackenzie, {Campbell Frank Ross} and Said, {Said A.} and Pal, {Amlan Kumar} and Haghighatbin, {Mohammed A.} and Azin Babaei and Michele Sessolo and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Kamer, {Paul C J} and Henk Bolink and Hogan, {Conor F.} and Eli Zysman-Colman",

note = "Funding: C.L. thanks the Prof. & Mrs Purdie Bequests Scholarship and AstraZeneca for a PhD Studentship. The St Andrews researchers thank the Engineering and Physical Sciences Research Council (EP/M02105X/1 and EP/R035164/1) for financial support. A.K.P. acknowledges the Leverhulme Trust and the University of St Andrews for an Early Career Fellowship (ECF-2017-326). H.J.B. and M.S. acknowledge funding from the Spanish Ministry of Science, Innovation and Universities (MAT2017‐88821‐R and RYC-2016-21316, respectively). C.F.H. acknowledges the support of the Australian Research Council (ARC) Discovery grant scheme (DP200102947).",

year = "2021",

month = jul,

day = "1",

doi = "10.1021/acs.inorgchem.1c00804",

language = "English",

volume = "Articles ASAP",

journal = "Inorganic Chemistry",

issn = "0020-1669",

publisher = "American Chemical Society (ACS)",

}

Li, C, Mackenzie, CFR, Said, SA, Pal, AK, Haghighatbin, MA, Babaei, A, Sessolo, M, Cordes, DB , Slawin, AMZ, Kamer, PCJ, Bolink, H, Hogan, CF & Zysman-Colman, E 2021, 'Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications', Inorganic Chemistry, vol. Articles ASAP. https://doi.org/10.1021/acs.inorgchem.1c00804

TY - JOUR

T1 - Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes

T2 - impact on the performance of electroluminescence applications

AU - Li, Chenfei

AU - Mackenzie, Campbell Frank Ross

AU - Said, Said A.

AU - Pal, Amlan Kumar

AU - Haghighatbin, Mohammed A.

AU - Babaei, Azin

AU - Sessolo, Michele

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Kamer, Paul C J

AU - Bolink, Henk

AU - Hogan, Conor F.

AU - Zysman-Colman, Eli

N1 - Funding: C.L. thanks the Prof. & Mrs Purdie Bequests Scholarship and AstraZeneca for a PhD Studentship. The St Andrews researchers thank the Engineering and Physical Sciences Research Council (EP/M02105X/1 and EP/R035164/1) for financial support. A.K.P. acknowledges the Leverhulme Trust and the University of St Andrews for an Early Career Fellowship (ECF-2017-326). H.J.B. and M.S. acknowledge funding from the Spanish Ministry of Science, Innovation and Universities (MAT2017‐88821‐R and RYC-2016-21316, respectively). C.F.H. acknowledges the support of the Australian Research Council (ARC) Discovery grant scheme (DP200102947).

PY - 2021/7/1

Y1 - 2021/7/1

N2 - We report a series of seven cationic heteroleptic copper(I) complexes of the form [Cu(P^P)(dmphen)]BF4, where dmphen is 2,9-dimethyl-1,10-phenanthroline and P^P is a diphosphine chelate, in which the effect of the bite angle of the diphosphine ligand on the photophysical properties of the complexes was studied. Several of the complexes exhibit moderately high photoluminescence quantum yields in the solid state, with ΦPL of up to 35%, and in solution, with ΦPL of up to 98%. We were able to correlate the powder photoluminescence quantum yields with the % Vbur of the P^P ligand. The most emissive complexes were used to fabricate both organic light-emitting diodes and light-emitting electrochemical cells (LECs), both of which showed moderate performance. Compared to the benchmark copper(I)-based LECs, [Cu(dnbp)(DPEPhos)]+ (maximum external quantum efficiency, EQEmax = 16%), complex 3 (EQEmax = 1.85%) showed a much longer device lifetime (t1/2 = 1.25 h and >16.5 h for [Cu(dnbp)(DPEPhos)]+ and complex 3, respectively). The electrochemiluminescence (ECL) properties of several complexes were also studied, which, to the best of our knowledge, constitutes the first ECL study for heteroleptic copper(I) complexes. Notably, complexes exhibiting more reversible electrochemistry were associated with higher annihilation ECL as well as better performance in a LEC.

AB - We report a series of seven cationic heteroleptic copper(I) complexes of the form [Cu(P^P)(dmphen)]BF4, where dmphen is 2,9-dimethyl-1,10-phenanthroline and P^P is a diphosphine chelate, in which the effect of the bite angle of the diphosphine ligand on the photophysical properties of the complexes was studied. Several of the complexes exhibit moderately high photoluminescence quantum yields in the solid state, with ΦPL of up to 35%, and in solution, with ΦPL of up to 98%. We were able to correlate the powder photoluminescence quantum yields with the % Vbur of the P^P ligand. The most emissive complexes were used to fabricate both organic light-emitting diodes and light-emitting electrochemical cells (LECs), both of which showed moderate performance. Compared to the benchmark copper(I)-based LECs, [Cu(dnbp)(DPEPhos)]+ (maximum external quantum efficiency, EQEmax = 16%), complex 3 (EQEmax = 1.85%) showed a much longer device lifetime (t1/2 = 1.25 h and >16.5 h for [Cu(dnbp)(DPEPhos)]+ and complex 3, respectively). The electrochemiluminescence (ECL) properties of several complexes were also studied, which, to the best of our knowledge, constitutes the first ECL study for heteroleptic copper(I) complexes. Notably, complexes exhibiting more reversible electrochemistry were associated with higher annihilation ECL as well as better performance in a LEC.

KW - Redox reactions

KW - Ligands

KW - Crystal structure

KW - Organophosphorus compounds

KW - Nuclear magnetic resonance spectroscopy

UR - https://doi.org/10.26434/chemrxiv.14046449.v1

U2 - 10.1021/acs.inorgchem.1c00804

DO - 10.1021/acs.inorgchem.1c00804

M3 - Article

SN - 0020-1669

VL - Articles ASAP

JO - Inorganic Chemistry

JF - Inorganic Chemistry

ER -

Wide-bite-angle disphosphine ligands in thermally activated delayed fluorescent copper(I) complexes: impact on the performance of electroluminescence applications

Abstract

Keywords

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