4.8 Article

Blue TADF Emitters Based on Indenocarbazole Derivatives with High Photoluminescence and Electroluminescence Efficiencies

Journal

ACS APPLIED MATERIALS & INTERFACES
Volume 11, Issue 11, Pages 10758-10767

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acsami.8b20699

Keywords

thermally activated delayed fluorescence (TADF); indenocarbazole derivatives; substituted position; substituents; photophysical properties

Funding

  1. NSFC/China [51573065, 51727809]
  2. China Postdoctoral Science Foundation [2017M620321]
  3. science and technology support program of Hubei Province [2015BAA075]
  4. Royal Society, UK [IEC\NSFC\170130]

Ask authors/readers for more resources

A series of blue thermally activated delayed fluorescence (TADF) emitters were designed and synthesized using 2,4,6-triphenyl-1,3,5-triazine as the acceptor unit and indenocarbazole derivatives as the electron donating moiety. In contrast with other six-membered heterocycles, like phenothiazine, phenoxazine, and dihydroacridine, where the TADF efficiency is affected by the presence of different conformers, indenocarbazole derivatives do not show this effect. Therefore, InCz23FlTz, InCz23DPhTz, InCz23DMeTz, and InCz34DPhTz allow the investigation of the effect of different substituents and substitution positions on TADF properties, without the influence of different conformations. We have demonstrated that the substituted position on the carbazole and different substituents in the same position have clear influence on the donor character of indenocarbazole derivatives. Also, the color purity of blue emission and excited states could be adjusted by substituents and substituted position, and thus excellent blue emitters can be obtained. Besides, the four compounds show relatively small TADF contribution under optical excitation; however, excellent performances are obtained in the electroluminescent devices, especially with InCz34DPhTz, which shows a maximum external quantum efficiency of around 26%. In the end, we find an effective way to design high-efficiency blue TADF materials and deeply study the relation between the structure and property in indenocarbazole derivatives.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Organic

Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence: Linking Donor Units to Influence Molecular Conformation

Matthias Hempe, Alastair K. Harrison, Jonathan S. Ward, Andrei S. Batsanov, Mark A. Fox, Fernando B. Dias, Martin R. Bryce

Summary: This study presents a synthetic methodology to covalently link donors to form cyclophane-based thermally activated delayed fluorescence (TADF) molecules, showing that the cyclophane molecular architecture alters the conformational distribution of the donor units and retains rotational freedom crucial for efficient TADF. Despite their different structures, cyclophanes and their nonbridged precursors exhibit similar photophysical properties emitting through similar excited states. Linking donor units to form a cyclophane suppresses detrimental conformations, establishing a versatile strategy while maintaining excellent photophysical properties.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Optics

Intramolecular interchromophore singlet-singlet and triplet-singlet energy transfer in a metal-free donor-acceptor emitter

Ines G. Tavares, Erki Enkvist, Joosep Kaimre, Asko Uri, Fernando B. Dias

Summary: This work investigates the intramolecular energy transfer between two thiophene donors and a perylene bisimide acceptor, demonstrating the transfer of energy from the thiophene donor's excited triplet state to the perylene bisimide acceptor's singlet state. The designed organic luminophore, ARC-1467, shows delayed fluorescence of perylene bisimide upon excitation of the donor unit, indicating the occurrence of energy transfer from the triplet state of the donor unit to the perylene bisimide acceptor.

JOURNAL OF LUMINESCENCE (2021)

Article Engineering, Environmental

Realize efficient organic afterglow from simple halogenated acridan derivatives

Xialei Lv, Xiaosong Cao, Han Wu, Hong Lin, Fan Ni, Hong Huang, Yang Zou, Chuluo Yang

Summary: This study presents a twisted donor-acceptor (D-A) system by simple conjugation of acridan and aryl halide to construct efficient and ultralong room-temperature phosphorescence (RTP) luminogens, demonstrating high phosphorescence quantum efficiency and long lifetime. This offers rare examples of efficient and long-lived phosphors based on acridan building block, shedding light on the inherent photophysical mechanism of RTP materials and paving a way to design highly promising RTP luminogens.

CHEMICAL ENGINEERING JOURNAL (2021)

Article Chemistry, Multidisciplinary

Asymmetrical-Dendronized TADF Emitters for Efficient Non-doped Solution-Processed OLEDs by Eliminating Degenerate Excited States and Creating Solely Thermal Equilibrium Routes

Chensen Li, Alastair K. Harrison, Yuchao Liu, Zhennan Zhao, Cheng Zeng, Fernando B. Dias, Zhongjie Ren, Shouke Yan, Martin R. Bryce

Summary: The mechanism of thermally activated delayed fluorescence (TADF) in dendrimers is not clear. This study focuses on fully-conjugated or fully-nonconjugated structures and their impact on TADF efficiency. The researchers synthesized asymmetrical half-dendronized and half-dendronized-half-encapsulated emitters to eliminate degenerate excited states and enhance the spin-flip process. By utilizing a encapsulating tricarbazole unit, nonradiative decay is reduced and TADF performance is improved. The non-doped solution-processed devices achieved high external quantum efficiency (EQE) with low efficiency roll-off at different brightness levels.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Materials Science, Multidisciplinary

Enhancement of thermally activated delayed fluorescence properties by substitution of ancillary halogen in a multiple resonance-like diplatinum(ii) complex

Piotr Pander, Andrey Zaytsev, Amit Sil, J. A. Gareth Williams, Valery N. Kozhevnikov, Fernando B. Dias

Summary: In this study, we investigated the influence of chloro-to-iodo exchange on the thermally activated delayed fluorescence (TADF) of a dinuclear platinum(ii) complex featuring monodentate halide ancillary ligands. The results showed that the iodine analogue exhibited improved luminescence properties with a significantly higher radiative decay rate constant compared to the chloro analogue. This study provides the first practical strategy to enhance the TADF properties of diplatinum(ii) complexes by iodination.

JOURNAL OF MATERIALS CHEMISTRY C (2022)

Article Chemistry, Physical

Novel Easy to Synthesize Benzonitrile Compounds with Mixed Carbazole and Phenoxazine Substituents Exhibiting Dual Emission and TADF Properties

Antonio Maggiore, Yangyang Qu, Regis Guillot, Piotr Pander, Marharyta Vasylieva, Przemyslaw Data, Fernando B. Dias, Pierre Audebert, Gilles Clavier, Fabien Miomandre

Summary: This study investigates the photophysical and electrochemical properties of a new class of fluorinated benzonitrile compounds that are substituted with mixed phenoxazine and carbazole units. The compounds exhibit dual broad emission due to both localized and charge-transfer absorptions over a large range of the UV-vis spectrum. In solution, their photoluminescence quantum yields vary from a few percent to 18% in a more rigid environment. Additionally, the compounds demonstrate thermally activated delayed fluorescence, which is influenced by the number of phenoxazine substituents. Electrochemistry also reveals significant changes in the reduction mechanisms based on the remaining fluorine atoms on the benzonitrile core.

JOURNAL OF PHYSICAL CHEMISTRY B (2022)

Article Chemistry, Analytical

Zinc Phthalocyanine Sensing Mechanism Quantification for Potential Application in Chemical Warfare Agent Detectors

Paulina Powroznik, Barbara Solecka, Piotr Pander, Wieslaw Jakubik, Fernando B. Dias, Maciej Krzywiecki

Summary: Rapid and accurate detection of lethal volatile compounds is crucial for current and future societal security. This study utilizes thermal desorption spectroscopy (TDS) to investigate the adsorption of DMMP, a sarin analogue, on ZnPc, and employs quantum chemistry calculations to determine desorption activation energies. The comprehensive understanding of the DMMP desorption processes from ZnPc obtained in this work serves as the foundation for successful future applications of sarin ZnPc-based sensors. Impedance spectroscopy confirms the sensing capability of the studied material at room temperature, demonstrating ZnPc's potential as a promising sarin sensor candidate.

SENSORS (2022)

Article Chemistry, Inorganic & Nuclear

Electroluminescence of Tetradentate Pt(II) Complexes: O∧N∧N∧O versus C∧N∧N∧O Coordination

Piotr Pander, Larissa Gomes Franca, Fernando B. Dias, Valery N. Kozhevnikov

Summary: Alkylation of a phenolic hydroxyl group in a salen-type ligand changes its coordination mode and allows the synthesis of a new luminescent Pt(II) complex 2. While the complex is not luminescent in solution, it exhibits emission in the solid state, making it suitable for organic light-emitting diodes. Complex 2 shows high external quantum efficiency and luminance in a vacuum-deposited device. Comparative analysis shows that the luminescent properties of O<^>N<^>N<^>O and C<^>N<^>N<^>O complexes are coincidental, and the two complexes display different electrochemical behavior.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Inorganic & Nuclear

Unusual Excimer/Dimer Behavior of a Highly Soluble C,N Platinum(II) Complex with a Spiro-Fluorene Motif

Piotr Pander, Andrey V. Zaytsev, Larissa Gomes Franca, Fernando B. Dias, Valery N. Kozhevnikov

Summary: In this work, we introduced a spiro-fluorene unit into a phenylpyridine (CN)-type ligand to deplanarize the structure and increase the solubility of a platinum(II) complex. This approach is highly important in the design of platinum(II) complexes to overcome low solubility and offers an alternative to using bulky alkyl groups. The nonplanar structure is also beneficial for vacuum-deposition techniques and eliminates the undesired feature of containing sp(3) hybridized carbon atoms.

INORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Synergistic Halide- and Ligand-Exchanges of All-Inorganic Perovskite Nanocrystals for Near-Unity and Spectrally Stable Red Emission

Kaiwang Chen, Dengliang Zhang, Qing Du, Wei Hong, Yue Liang, Xingxing Duan, Shangwei Feng, Linfeng Lan, Lei Wang, Jiangshan Chen, Dongge Ma

Summary: This study presents a method to prepare stable pure red emission and high-PLQY-mixed-halide perovskite nanocrystals through simultaneous halide-exchange and ligand-exchange. By introducing ZnI2 for anion exchange, CsPbBr3 nanocrystals can be transformed to CsPbBrxI3-x nanocrystals. The luminescence properties can be regulated by the ZnI2 exchange process, allowing the fabrication of red CsPbBrxI3-x nanocrystals with near-unity PLQY and a stable emission peak.

NANOMATERIALS (2023)

Article Chemistry, Inorganic & Nuclear

9-Borafluoren-9-yl and diphenylboron tetracoordinate complexes of F- and Cl-substituted 8-quinolinolato ligands: synthesis, molecular and electronic structures, fluorescence and application in OLED devices

Carina B. Fialho, Tiago F. C. Cruz, Ana I. Rodrigues, Maria Jose Calhorda, Luis F. Vieira Ferreira, Piotr Pander, Fernando B. Dias, Jorge Morgado, Antonio L. Macanita, Pedro T. Gomes

Summary: Six new four-coordinate tetrahedral boron complexes with 9-borafluoren-9-yl and diphenylboron cores attached to 8-quinolinolato ligand chromophores have been synthesized and characterized. These complexes exhibit delayed fluorescence (DF) in solid films, originating from triplet-triplet annihilation (TTA). Density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies provide insights into the physical properties and electronic structures of these new luminophores. Furthermore, these compounds have been successfully applied as emitters in organic light-emitting diodes (OLEDs), achieving green-blue electroluminescence with good external quantum efficiency (EQE) and high luminance.

DALTON TRANSACTIONS (2023)

Article Chemistry, Multidisciplinary

Thermally activated delayed fluorescence in a deep red dinuclear iridium(iii) complex: a hidden mechanism for short luminescence lifetimes

Piotr Pander, Andrey V. Zaytsev, Amit Sil, Glib V. Baryshnikov, Farhan Siddique, J. A. Gareth Williams, Fernando B. Dias, Valery N. Kozhevnikov

Summary: This study discovers a new luminescence mechanism called thermally activated delayed fluorescence (TADF) in iridium(III) complexes. By incorporating a faster fluorescent radiative decay pathway, the design of iridium(III) complexes can be improved in terms of luminescence efficiency and performance.

CHEMICAL SCIENCE (2023)

Article Chemistry, Multidisciplinary

Near-infrared electroluminescence beyond 940 nm in Pt(N∧C∧N)X complexes: influencing aggregation with the ancillary ligand X

Rebecca J. Salthouse, Piotr Pander, Dmitry S. Yufit, Fernando B. Dias, J. A. Gareth Williams

Summary: We conducted a study on aggregate excited states formed by complexes of the type Pt(NC)X, where N<^>C<^>N represents a tridentate cyclometallating ligand, and X = SCN or I. We found that the identity of the monodentate ligand strongly influenced aggregation in film. The use of X = SCN promoted the formation of larger aggregates, while X = I limited aggregation to dimers. By exploiting the propensity of SCN complexes to form extended aggregates, we achieved an unprecedented NIR-emitting OLED.

CHEMICAL SCIENCE (2022)

Article Materials Science, Multidisciplinary

Excimer or aggregate? Near infrared electro- and photoluminescence from multimolecular excited states of N∧C∧N-coordinated platinum(ii) complexes

Piotr Pander, Amit Sil, Rebecca J. Salthouse, Christopher W. Harris, Melissa T. Walden, Dmitry S. Yufit, J. A. Gareth Williams, Fernando B. Dias

Summary: This study presents an experimental and theoretical investigation on the aggregate excited states formed by Pt(NCN)Cl complexes. The complexes exhibit near-infrared photoluminescence in films and electroluminescence in OLED devices. The study provides insights into the kinetic properties of Pt-Pt excimers and proposes an alternative OLED architecture to reduce the use of precious-metal compounds.

JOURNAL OF MATERIALS CHEMISTRY C (2022)

Article Materials Science, Multidisciplinary

The role of dinuclearity in promoting thermally activated delayed fluorescence (TADF) in cyclometallated, N∧C∧N-coordinated platinum(ii) complexes

Piotr Pander, Andrey Zaytsev, Amit Sil, J. A. Gareth Williams, Pierre-Henri Lanoe, Valery N. Kozhevnikov, Fernando B. Dias

Summary: Through synthesis and analysis, we have discovered a di-Pt(ii) complex that exhibits dual luminescent behavior and activates thermally activated delayed fluorescence. Compared with the mono-Pt(ii) analogue, the di-Pt(ii) complex has a larger singlet radiative rate constant, a smaller singlet-triplet energy gap, and a longer phosphorescence decay lifetime. This bimetallic structure promotes conditions favorable for TADF, showcasing high efficiency in emitting near infrared electroluminescence.

JOURNAL OF MATERIALS CHEMISTRY C (2021)

No Data Available