Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes

Pavel Arsenyan; Alla Petrenko; Audrius Bucinskas; Ehsan Ullah Rashid; Kuan Wei Chen; Jiun Haw Lee; Tien Lung Chiu; Oleksandr Bezvikonnyi; Dmytro Volyniuk; Sergey Belyakov; Juozas V. Grazulevicius

doi:10.1002/aelm.202500554

Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes

Pavel Arsenyan^*
, Alla Petrenko
, Audrius Bucinskas
, Ehsan Ullah Rashid
, Kuan Wei Chen
, Jiun Haw Lee^*
, Tien Lung Chiu^*
, Oleksandr Bezvikonnyi
, Dmytro Volyniuk
, Sergey Belyakov
, Juozas V. Grazulevicius^*

^*Corresponding author for this work

Laboratory of Organic Materials, Institute of Solid State Physics

Latvian Academy of Sciences
Kaunas University of Technology
National Taiwan University
Yuan Ze University

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

Abstract

The aim of this work is the exploration of the impact of the methoxy-, methoxyethoxy- and tert-butyl functional groups on the structure-property relationships of the derivatives of anthracene and carbazole exhibiting triplet-triplet annihilation (TTA) upconversion. The synthesis of three new organic semiconductors that possess tert-butyl, methoxy, or methoxyethoxy side groups linked via C-3 and C-6 positions of carbazole fragments is reported. The compounds exhibit high thermal stability with 5% weight loss temperatures in the range of 377–413 °C. The emitter with tert-butylcarbazole moiety exhibits a high photoluminescence quantum yield (PLQY) of 68.2%, ionization energy of 5.65 eV. The occurrence of TTA is discussed in detail, drawing on both experimental data and theoretical analysis. Organic light emitting diode based on the neat layer of the emitter shows maximum external quantum efficiency (EQE) of 3.1%. Optimization of the device structure using a host-guest system allows to increase the EQE to 10.7%. It is shown that high EQE is a result of improved horizontal molecular alignment, TTA upconversion and high PLQY.

Original language	English
Article number	e00554
Journal	Advanced Electronic Materials
Volume	11
Issue number	20
DOIs	https://doi.org/10.1002/aelm.202500554
Publication status	Published - 3 Dec 2025

Keywords

OLEDs
TTA
anthracene
methoxy
tert-butyl

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10.1002/aelm.202500554

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Arsenyan, P., Petrenko, A., Bucinskas, A., Rashid, E. U., Chen, K. W., Lee, J. H., Chiu, T. L., Bezvikonnyi, O., Volyniuk, D., Belyakov, S., & Grazulevicius, J. V. (2025). Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes. Advanced Electronic Materials, 11(20), Article e00554. https://doi.org/10.1002/aelm.202500554

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title = "Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes",

abstract = "The aim of this work is the exploration of the impact of the methoxy-, methoxyethoxy- and tert-butyl functional groups on the structure-property relationships of the derivatives of anthracene and carbazole exhibiting triplet-triplet annihilation (TTA) upconversion. The synthesis of three new organic semiconductors that possess tert-butyl, methoxy, or methoxyethoxy side groups linked via C-3 and C-6 positions of carbazole fragments is reported. The compounds exhibit high thermal stability with 5\% weight loss temperatures in the range of 377–413 °C. The emitter with tert-butylcarbazole moiety exhibits a high photoluminescence quantum yield (PLQY) of 68.2\%, ionization energy of 5.65 eV. The occurrence of TTA is discussed in detail, drawing on both experimental data and theoretical analysis. Organic light emitting diode based on the neat layer of the emitter shows maximum external quantum efficiency (EQE) of 3.1\%. Optimization of the device structure using a host-guest system allows to increase the EQE to 10.7\%. It is shown that high EQE is a result of improved horizontal molecular alignment, TTA upconversion and high PLQY.",

keywords = "OLEDs, TTA, anthracene, methoxy, tert-butyl",

author = "Pavel Arsenyan and Alla Petrenko and Audrius Bucinskas and Rashid, \{Ehsan Ullah\} and Chen, \{Kuan Wei\} and Lee, \{Jiun Haw\} and Chiu, \{Tien Lung\} and Oleksandr Bezvikonnyi and Dmytro Volyniuk and Sergey Belyakov and Grazulevicius, \{Juozas V.\}",

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month = dec,

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doi = "10.1002/aelm.202500554",

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T1 - Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes

AU - Arsenyan, Pavel

AU - Petrenko, Alla

AU - Bucinskas, Audrius

AU - Rashid, Ehsan Ullah

AU - Chen, Kuan Wei

AU - Lee, Jiun Haw

AU - Chiu, Tien Lung

AU - Bezvikonnyi, Oleksandr

AU - Volyniuk, Dmytro

AU - Belyakov, Sergey

AU - Grazulevicius, Juozas V.

PY - 2025/12/3

Y1 - 2025/12/3

N2 - The aim of this work is the exploration of the impact of the methoxy-, methoxyethoxy- and tert-butyl functional groups on the structure-property relationships of the derivatives of anthracene and carbazole exhibiting triplet-triplet annihilation (TTA) upconversion. The synthesis of three new organic semiconductors that possess tert-butyl, methoxy, or methoxyethoxy side groups linked via C-3 and C-6 positions of carbazole fragments is reported. The compounds exhibit high thermal stability with 5% weight loss temperatures in the range of 377–413 °C. The emitter with tert-butylcarbazole moiety exhibits a high photoluminescence quantum yield (PLQY) of 68.2%, ionization energy of 5.65 eV. The occurrence of TTA is discussed in detail, drawing on both experimental data and theoretical analysis. Organic light emitting diode based on the neat layer of the emitter shows maximum external quantum efficiency (EQE) of 3.1%. Optimization of the device structure using a host-guest system allows to increase the EQE to 10.7%. It is shown that high EQE is a result of improved horizontal molecular alignment, TTA upconversion and high PLQY.

AB - The aim of this work is the exploration of the impact of the methoxy-, methoxyethoxy- and tert-butyl functional groups on the structure-property relationships of the derivatives of anthracene and carbazole exhibiting triplet-triplet annihilation (TTA) upconversion. The synthesis of three new organic semiconductors that possess tert-butyl, methoxy, or methoxyethoxy side groups linked via C-3 and C-6 positions of carbazole fragments is reported. The compounds exhibit high thermal stability with 5% weight loss temperatures in the range of 377–413 °C. The emitter with tert-butylcarbazole moiety exhibits a high photoluminescence quantum yield (PLQY) of 68.2%, ionization energy of 5.65 eV. The occurrence of TTA is discussed in detail, drawing on both experimental data and theoretical analysis. Organic light emitting diode based on the neat layer of the emitter shows maximum external quantum efficiency (EQE) of 3.1%. Optimization of the device structure using a host-guest system allows to increase the EQE to 10.7%. It is shown that high EQE is a result of improved horizontal molecular alignment, TTA upconversion and high PLQY.

KW - OLEDs

KW - TTA

KW - anthracene

KW - methoxy

KW - tert-butyl

UR - https://www.scopus.com/pages/publications/105021267423

U2 - 10.1002/aelm.202500554

DO - 10.1002/aelm.202500554

M3 - Article

AN - SCOPUS:105021267423

SN - 2199-160X

VL - 11

JO - Advanced Electronic Materials

JF - Advanced Electronic Materials

IS - 20

M1 - e00554

ER -

Boosting Triplet-Triplet Annihilation Upconversion in OLEDs via Substituent Control in Dicarbazolyl Anthracenes

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Keywords

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