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PreprintCC BYChemRxiv

Red TADF Pyridoquinoxaline-Annulated Curved Nitrogen-Doped PAHs and their use in OLEDs

  • Jakub Wagner1
  • Eglė Tankelevičiūtė2,3,4
  • Haoyang Li2,3
  • Tomas Matulaitis2,3
  • Maja Morawiak1
  • Maciej Jelecki1
  • Ifor D. W. Samuel4,3
  • Eli Zysman-Colman2,3
  • Marcin Lindner1
4 affiliations
  1. 1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw, Poland, 01-224
  2. 2Organic Semiconductor Centre, EaStCHEM School of Chemistry
  3. 3University of St Andrews
  4. 4School of Physics & Astronomy
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Abstract

Curved nitrogen-doped polycyclic aromatic hydrocarbons offer a rigid and nonplanar framework for investigating how donor identity regulates the balance between locally excited and chargetransfer states in thermally activated delayed fluorescence (TADF) emitters. Here, a pyrido[2,3b]quinoxaline unit was integrated into a dibenzo[b,f]azepine-based polycyclic aromatic hydrocarbon scaffold and functionalized with one of 3,6-di-tert-butylcarbazole (TBCzPyN-PAH), diphenylamine (DPAPyN-PAH), 9,9-dimethyl-9,10-dihydroacridine (DMAcPyN-PAH), or phenoxazine (PXZPyN-PAH) donor moieties. The resulting series provides a common acceptor framework in which the electronic and conformational properties of the peripheral donor affect the 2 energies of the excited states. Donor substitution tunes the emission maximum in toluene from 528 to 697 nm. In 2 wt% doped films in CBP, these compounds emit from 519 to 622 nm with PLQY of up to 58%. Temperature-dependent time-resolved photoluminescence confirms TADF for all investigated compounds except for the DPA derivative. Across the TADF-active series, the singlet–triplet energy gap, ΔEST, decreases from 0.22 to 0.03 eV and the delayed fluorescence lifetime shortens from 8.5 ms to 29 μs. Vacuum-deposited OLEDs with TBCzPyN-PAH showed EQEmax, of 21.6% at an electroluminescence maximum of 538 nm, whereas the device with PXZPyN-PAH emitted at 606 nm and showed a lower EQEmax of 7.2% but with a milder efficiency roll-off.

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Cite

BibTeXRIS
BibTeX
@misc{wagner2026tadf,
  title = {{Red TADF Pyridoquinoxaline-Annulated Curved Nitrogen-Doped PAHs and their use in OLEDs}},
  author = {Jakub Wagner and Eglė Tankelevičiūtė and Haoyang Li and Tomas Matulaitis and Maja Morawiak and Maciej Jelecki and Ifor D. W. Samuel and Eli Zysman-Colman and Marcin Lindner},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008900/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008900/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Red TADF Pyridoquinoxaline-Annulated Curved Nitrogen-Doped PAHs and their use in OLEDs
AU  - Jakub Wagner
AU  - Eglė Tankelevičiūtė
AU  - Haoyang Li
AU  - Tomas Matulaitis
AU  - Maja Morawiak
AU  - Maciej Jelecki
AU  - Ifor D. W. Samuel
AU  - Eli Zysman-Colman
AU  - Marcin Lindner
PY  - 2026
DA  - 2026/09/16
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008900/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008900/v1
AB  - Curved nitrogen-doped polycyclic aromatic hydrocarbons offer a rigid and nonplanar framework for investigating how donor identity regulates the balance between locally excited and chargetransfer states in thermally activated delayed fluorescence (TADF) emitters. Here, a pyrido[2,3b]quinoxaline unit was integrated into a dibenzo[b,f]azepine-based polycyclic aromatic hydrocarbon scaffold and functionalized with one of 3,6-di-tert-butylcarbazole (TBCzPyN-PAH), diphenylamine (DPAPyN-PAH), 9,9-dimethyl-9,10-dihydroacridine (DMAcPyN-PAH), or phenoxazine (PXZPyN-PAH) donor moieties. The resulting series provides a common acceptor framework in which the electronic and conformational properties of the peripheral donor affect the 2 energies of the excited states. Donor substitution tunes the emission maximum in toluene from 528 to 697 nm. In 2 wt% doped films in CBP, these compounds emit from 519 to 622 nm with PLQY of up to 58%. Temperature-dependent time-resolved photoluminescence confirms TADF for all investigated compounds except for the DPA derivative. Across the TADF-active series, the singlet–triplet energy gap, ΔEST, decreases from 0.22 to 0.03 eV and the delayed fluorescence lifetime shortens from 8.5 ms to 29 μs. Vacuum-deposited OLEDs with TBCzPyN-PAH showed EQEmax, of 21.6% at an electroluminescence maximum of 538 nm, whereas the device with PXZPyN-PAH emitted at 606 nm and showed a lower EQEmax of 7.2% but with a milder efficiency roll-off.
ER  -