Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs

Zhen Zhang; Stefan Diesing; Ettore Crovini; Abhishek Kumar Gupta; Eduard Spuling; Xuemin Gua; Olaf Fuhr; Martin Nieger; Zahid Hassan; Ifor D. W. Samuel; Stefan Bräse; Eli Zysman-Colman

doi:10.1021/acs.orglett.1c02273

Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs

Zhen Zhang, Stefan Diesing, Ettore Crovini, Abhishek Kumar Gupta, Eduard Spuling, Xuemin Gua, Olaf Fuhr, Martin Nieger, Zahid Hassan, Ifor D. W. Samuel, Stefan Bräse, Eli Zysman-Colman

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

Abstract

Conjugation-extended carbazolophane donors, dicarbazolophanes (DCzp), were designed and synthesized using a multifold stepwise Pd-catalyzed Buchwald–Hartwig amination/ring cyclization process. Furthermore, elaboration of the DCzp core is possible with the introduction of pendant carbazole derivative groups. This provides a way to tune the optoelectronic properties of the thermally activated delayed fluorescence (TADF) compounds DCzpTRZtBu, dtBuCzDCzpTRZtBu, and dMeOCzDCzpTRZtBu. Solution-processed organic light-emitting diodes (OLEDs) were fabricated and achieved a maximum external quantum efficiency (EQE_max) of 8.2% and an EQE of 7.9% at 100 cd/m².

Original language	English
Journal	Organic Letters
Volume	Articles ASAP
Early online date	13 Aug 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c02273
Publication status	E-pub ahead of print - 13 Aug 2021

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Zhang_2021_ OL_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.orglett.1c02273
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Zhang, Z., Diesing, S., Crovini, E., Gupta, A. K., Spuling, E., Gua, X., Fuhr, O., Nieger, M., Hassan, Z., Samuel, I. D. W., Bräse, S., & Zysman-Colman, E. (2021). Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs. Organic Letters, Articles ASAP. Advance online publication. https://doi.org/10.1021/acs.orglett.1c02273

@article{71fc1bc769a5489b836195715fce0286,

title = "Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs",

abstract = "Conjugation-extended carbazolophane donors, dicarbazolophanes (DCzp), were designed and synthesized using a multifold stepwise Pd-catalyzed Buchwald–Hartwig amination/ring cyclization process. Furthermore, elaboration of the DCzp core is possible with the introduction of pendant carbazole derivative groups. This provides a way to tune the optoelectronic properties of the thermally activated delayed fluorescence (TADF) compounds DCzpTRZtBu, dtBuCzDCzpTRZtBu, and dMeOCzDCzpTRZtBu. Solution-processed organic light-emitting diodes (OLEDs) were fabricated and achieved a maximum external quantum efficiency (EQEmax) of 8.2% and an EQE of 7.9% at 100 cd/m2.",

author = "Zhen Zhang and Stefan Diesing and Ettore Crovini and Gupta, {Abhishek Kumar} and Eduard Spuling and Xuemin Gua and Olaf Fuhr and Martin Nieger and Zahid Hassan and Samuel, {Ifor D. W.} and Stefan Br{\"a}se and Eli Zysman-Colman",

note = "The German Research Foundation (formally Deutsche Forschungsgemeinschaft DFG) in the framework of SFB1176 Co-operative Research Centre “Molecular Structuring of Soft Matter” (CRC1176, A4, B3, C2, C6) and the cluster “3D Matter Made to Order” funded under Germany{\textquoteright}s Excellence Strategy 2082/1–390761711 are acknowledged for financial contributions. A. K. G. is thankful to the Royal Society for a Newton International Fellowship NF171163. E. Z.-C. and I. D. W. S. acknowledge support from EPSRC (EP/L017008, EP/P010482/1, EP/R035164/1). E. C. and E. Z.-C. acknowledge the EU Horizon 2020 grant agreement no. 812872 (TADFlife).",

year = "2021",

month = aug,

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doi = "10.1021/acs.orglett.1c02273",

language = "English",

volume = "Articles ASAP",

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Zhang, Z, Diesing, S, Crovini, E, Gupta, AK, Spuling, E, Gua, X, Fuhr, O, Nieger, M, Hassan, Z, Samuel, IDW, Bräse, S & Zysman-Colman, E 2021, 'Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs', Organic Letters, vol. Articles ASAP. https://doi.org/10.1021/acs.orglett.1c02273

TY - JOUR

T1 - Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs

AU - Zhang, Zhen

AU - Diesing, Stefan

AU - Crovini, Ettore

AU - Gupta, Abhishek Kumar

AU - Spuling, Eduard

AU - Gua, Xuemin

AU - Fuhr, Olaf

AU - Nieger, Martin

AU - Hassan, Zahid

AU - Samuel, Ifor D. W.

AU - Bräse, Stefan

AU - Zysman-Colman, Eli

N1 - The German Research Foundation (formally Deutsche Forschungsgemeinschaft DFG) in the framework of SFB1176 Co-operative Research Centre “Molecular Structuring of Soft Matter” (CRC1176, A4, B3, C2, C6) and the cluster “3D Matter Made to Order” funded under Germany’s Excellence Strategy 2082/1–390761711 are acknowledged for financial contributions. A. K. G. is thankful to the Royal Society for a Newton International Fellowship NF171163. E. Z.-C. and I. D. W. S. acknowledge support from EPSRC (EP/L017008, EP/P010482/1, EP/R035164/1). E. C. and E. Z.-C. acknowledge the EU Horizon 2020 grant agreement no. 812872 (TADFlife).

PY - 2021/8/13

Y1 - 2021/8/13

N2 - Conjugation-extended carbazolophane donors, dicarbazolophanes (DCzp), were designed and synthesized using a multifold stepwise Pd-catalyzed Buchwald–Hartwig amination/ring cyclization process. Furthermore, elaboration of the DCzp core is possible with the introduction of pendant carbazole derivative groups. This provides a way to tune the optoelectronic properties of the thermally activated delayed fluorescence (TADF) compounds DCzpTRZtBu, dtBuCzDCzpTRZtBu, and dMeOCzDCzpTRZtBu. Solution-processed organic light-emitting diodes (OLEDs) were fabricated and achieved a maximum external quantum efficiency (EQEmax) of 8.2% and an EQE of 7.9% at 100 cd/m2.

AB - Conjugation-extended carbazolophane donors, dicarbazolophanes (DCzp), were designed and synthesized using a multifold stepwise Pd-catalyzed Buchwald–Hartwig amination/ring cyclization process. Furthermore, elaboration of the DCzp core is possible with the introduction of pendant carbazole derivative groups. This provides a way to tune the optoelectronic properties of the thermally activated delayed fluorescence (TADF) compounds DCzpTRZtBu, dtBuCzDCzpTRZtBu, and dMeOCzDCzpTRZtBu. Solution-processed organic light-emitting diodes (OLEDs) were fabricated and achieved a maximum external quantum efficiency (EQEmax) of 8.2% and an EQE of 7.9% at 100 cd/m2.

UR - https://doi.org/10.33774/chemrxiv-2021-z10sw

U2 - 10.1021/acs.orglett.1c02273

DO - 10.1021/acs.orglett.1c02273

M3 - Article

SN - 1523-7060

VL - Articles ASAP

JO - Organic Letters

JF - Organic Letters

ER -

Molecular design and synthesis of dicarbazolophane-based centro-symmetric through-space donors for solution-processed thermally activated delayed fluorescence OLEDs

Abstract

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H2020 - ITN ELI ZYSMAN-COLMAN: H2020 MSCA ITN TADFlife

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

Thermally Activated Delayed Fluorescenc: Thermally Activated Delayed Fluorescence Materials for Displays and Photodynamic Theory