3-(N,N-Diphenylamino)carbazole Donor Containing Bipolar Derivatives with Very High Glass Transition Temperatures as Potential TADF Emitters for OLEDs

Tavgenienė, Daiva; Beresneviciute, Raminta; Blaževičius, Dovydas; Kručaitė, Gintarė; Jacunskaite, Greta; Swayamprabha, Sujith Sudheendran; Jou, Jwo‐Huei; Grigalevičius, Saulius

doi:10.3390/coatings12070932

Cited by 4 publications

(5 citation statements)

References 41 publications

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“…To comprehend the thermal stability of the molecules, TGA and DSC experiments were conducted at a heating rate of 10 °C min –1 under nitrogen and argon atmospheres, respectively (Figures S4 and S5, respectively). High thermal stability and good T g of organic molecules are desirable to augment the lifetime of OLED devices . Also, a high glass-transition temperature enhances the film homogeneity and hence results in better device performance. , The presence of twisted aromatic amine units in the molecular architecture was expected to improve thermal stability.…”

Section: Resultsmentioning

confidence: 99%

“…High thermal stability and good T g of organic molecules are desirable to augment the lifetime of OLED devices . Also, a high glass-transition temperature enhances the film homogeneity and hence results in better device performance. , The presence of twisted aromatic amine units in the molecular architecture was expected to improve thermal stability. During DSC analysis, endothermic peaks were observed at 66, 178, and 76 °C, which are probably the glass-transition temperature ( T g ) of TPA-Py , DPA-2Py , and TPA-2Py , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…High thermal stability and good T g of organic molecules are desirable to augment the lifetime of OLED devices. 67 Also, a high glass-transition temperature enhances the film homogeneity and hence results in better device performance. 67,68 The presence of twisted aromatic amine units in the molecular architecture was expected to improve thermal stability.…”

Section: Electrochemical and Thermal Studiesmentioning

confidence: 99%

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Computational Evaluation with Experimental Validation: Arylamine-Based Functional Hole-Transport Materials for Energy-Efficient Solution-Processed OLEDs

Kumar,

Kesavan,

Kumar

et al. 2023

J. Phys. Chem. C

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Ultra-efficient and stable OLED devices can be obtained via effective charge injection, accumulation, and exciton confinement into the emissive layer. However, the leakage of charge and excitons from the EML to adjacent layers can lead to low device performance. Thus, high-triplet-energy charge-transport materials (CTMs) are required to confront these issues. Herein, we demonstrate a class of efficient arylamine derivatives, viz. TPA-Py, TPA-2Py, and DPA-2Py, which were synthesized through the insertion of triphenyl pyridine as an acceptor unit to the aryl amino system to accomplish high triplet energy, thermal stability, and charge transportability during device operation. The charge-transfer analysis of the developed materials was accomplished for the S1 and T1 states through theoretical simulation. The intramolecular hole reorganization energies helped in understanding the hole transportability of these molecules. Single-crystal analysis indicated a considerable dihedral angle across the units, quasiplanar geometries, and the nonexistence of π–π stacking in the solid state. These molecular materials exhibited good thermal stability, which improve the morphological stability of their thin films. All of the molecules possess suitable HOMO energy levels for hole injection and appropriate LUMO energy levels for electron blocking from the emissive layer. Moreover, their high triplet energy (up to 2.69 eV) prevents exciton transfer from the EML to HTL and results in better device performance. The device with DPA-2Py as an HTM in a green OLED showed the maximum current efficiency (CE) and power efficiency (PE) values of ∼74 cd/A and ∼72 lm/W, respectively, with a maximum EQE of ∼21%. The PE of the current device is at par with the highest reported PE so far in solution-processed phosphorescent OLEDs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Electrochemical and Thermal Studiesmentioning

confidence: 99%

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Computational Evaluation with Experimental Validation: Arylamine-Based Functional Hole-Transport Materials for Energy-Efficient Solution-Processed OLEDs

Kumar,

Kesavan,

Kumar

et al. 2023

J. Phys. Chem. C

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“…((4,10-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(4,1-phenylene))bis((4-bromophenyl)methanone) reacted with 9,9-dimethyl-9,10-dihydroacridine under similar conditions to prepare emitter EB12 [ 120 ]. Material EB7 [ 121 ] was synthesized during a simple nucleophilic substitution of 4,4′-diflourobenzophenone with 3-(N,N-diphenylamino)carbazole. Suzuki reaction was chosen as the best procedure for obtaining compound EB8 [ 122 ] from 4,4′-dibromobenzophenone and 9,9-dimethyl-10-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroacridine as initial reactants.…”

Section: Benzophenone-based Emitters Employing a Symmetric D–a–d Stru...mentioning

confidence: 99%

A Review of Benzophenone-Based Derivatives for Organic Light-Emitting Diodes

Blazevicius,

Grigalevicius

2024

Nanomaterials

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Organic light-emitting diodes (OLEDs) have garnered considerable attention in academic and industrial circles due to their potential applications in flat-panel displays and solid-state lighting technologies, leveraging the advantages offered by organic electroactive derivatives over their inorganic counterparts. The thin and flexible design of OLEDs enables the development of innovative lighting solutions, facilitating the creation of customizable and contoured lighting panels. Among the diverse electroactive components employed in the molecular design of OLED materials, the benzophenone core has attracted much attention as a fragment for the synthesis of organic semiconductors. On the other hand, benzophenone also functions as a classical phosphor with high intersystem crossing efficiency. This characteristic makes it a compelling candidate for effective reverse intersystem crossing, with potential in leading to the development of thermally activated delayed fluorescent (TADF) emitters. These emitting materials witnessed a pronounced interest in recent years due to their incorporation in metal-free electroactive frameworks and the capability to convert triplet excitons into emissive singlet excitons through reverse intersystem crossing (RISC), consequently achieving exceptionally high external quantum efficiencies (EQEs). This review article comprehensively overviews the synthetic pathways, thermal characteristics, electrochemical behaviour, and photophysical properties of derivatives based on benzophenone. Furthermore, we explore their applications in OLED devices, both as host materials and emitters, shedding light on the promising opportunities that benzophenone-based compounds present in advancing OLED technology.

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“…((4,10-Dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(4,1phenylene))bis((4-bromophenyl)methanone) reacted with 9,9-dimethyl-9,10-dihydroacridine under similar conditions to prepare emitter EB12 [120]. Material EB7 [121] was synthesized during a simple nucleophilic substitution of 4,4 ′ -diflourobenzophenone with 3-(N,N-diphenylamino)carbazole. Suzuki reaction was chosen as the best procedure for obtaining compound EB8 [122] from 4,4 ′ -dibromobenzophenone and 9,9-dimethyl-10phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroacridine as initial reactants.…”

Section: Benzophenone-based Emitters Employing a Symmetric D-a-d Stru...mentioning

confidence: 99%

A Review on Benzophenone-Based Derivatives for Organic Light Emitting Diodes

Blazevicius,

Grigalevicius

2024

Preprint

View full text Add to dashboard Cite

Organic light-emitting diodes (OLEDs) have garnered considerable attention in academic and industrial circles due to their potential applications in flat panel displays and solid-state lighting technologies, leveraging the advantages offered by organic electroactive derivatives over their inorganic counterparts. The thin and flexible design of OLEDs enables the development of innovative lighting solutions, facilitating the creation of customizable and contoured lighting panels. Among the diverse electroactive components employed in the molecular design of OLED materials, the benzophenone core has attracted much attention as fragment for synthesis of organic semiconductors. On the other hand, the benzophenone also functions as a classical phosphor with high intersystem crossing efficiency. This characteristic makes it as compelling candidate for effective reverse intersystem crossing, potentially leading to the development of thermally activated delayed fluorescent (TADF) emitters. These emitting materials witnessed a pronounced interest in recent years due to their incorporation in metal-free electroactive frameworks and the capability to convert triplet excitons into emissive singlet excitons through reverse intersystem crossing (RISC), consequently achieving exceptionally high external quantum efficiencies (EQEs). This review article comprehensively overviews the synthetic pathways, thermal characteristics, electrochemical behaviour and photo-physical properties of the derivatives based on benzophenone. Furthermore, we explore their applications in OLED devices, both as host materials and emitters, shedding light on the promising opportunities that benzophenone-based compounds present in advancing OLED technology.

show abstract

3-(N,N-Diphenylamino)carbazole Donor Containing Bipolar Derivatives with Very High Glass Transition Temperatures as Potential TADF Emitters for OLEDs

Cited by 4 publications

References 41 publications

Computational Evaluation with Experimental Validation: Arylamine-Based Functional Hole-Transport Materials for Energy-Efficient Solution-Processed OLEDs

Computational Evaluation with Experimental Validation: Arylamine-Based Functional Hole-Transport Materials for Energy-Efficient Solution-Processed OLEDs

A Review of Benzophenone-Based Derivatives for Organic Light-Emitting Diodes

A Review on Benzophenone-Based Derivatives for Organic Light Emitting Diodes

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