Blue phosphorescent organic light-emitting devices based on carbazole/thioxanthene-S,S-dioxide with a high glass transition temperature

Jeon, Young Pyo; Kim, Kyu Sung; Lee, Kyeong Kyun; Moon, In Kyu; Choo, D. C.; Lee, Jun Yeob; Kim, Tae Whan

doi:10.1039/c5tc00279f

Cited by 29 publications

(14 citation statements)

References 54 publications

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“…We also measured the T g of new m‐ CBPPO host, which was above 100 °C. The obtained value was relatively higher when compared to the T g of conventional host materials mCP, 4,4′‐bis(9‐carbazolyl)‐biphenyl and 4,4′‐bis(9‐carbazolyl)‐2,2′‐dimethylbiphenyl (55, 62, and 94 °C, respectively) . The systematic design strategy of m‐ CBPPO allowed us to achieve a high T d and T g .…”

Section: Resultsmentioning

confidence: 94%

High Efficiency Deep‐Blue Phosphorescent Organic Light‐Emitting Diodes with CIE x, y (≤ 0.15) and Low Efficiency Roll‐Off by Employing a High Triplet Energy Bipolar Host Material

Maheshwaran

Sree

Park

et al. 2018

Adv Funct Materials

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124

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Recently, bipolar host materials are the most promising candidates for achieving high performance phosphorescent organic light-emitting diodes (PHOLEDs) in order to maximize recombination efficiency. However, the development of host material with high triplet energy (E T ) is still a great challenge to date to overcome the limitations associated with the present PHOLEDs. Herein, a highly efficient donor-π-acceptor (D-π-A) type bipolar host (4′-(9H-carbazol-9-yl)-2,2′-dimethyl-[1,1′-biphenyl]-4-yl)diphenylphosphine oxide (m-CBPPO) comprising of carbazole, 2,2′-dimethylbiphenyl and diphenylphosphoryl as D-π-A unit, respectively, is developed. Interestingly, a high E T of 3.02 eV is observed for m-CBPPO due to highly twisted conformation. Furthermore, the new host material is incorporated in PHOLEDs as emissive layer with a new carbene type Ir(cb) 3 material as a deep-blue emitter. The optimized devices show an excellent external quantum efficiency (EQE) of 24.8%with a notable Commission internationale de l'éclairage (x, y) ≤ 0.15, (0.136, 0.138) and high electroluminescence performance with extremely low efficiency roll-off. Overall, the above EQE is the highest reported for deep-blue PHOLEDs with very low efficiency roll-off and also indicate the importance of appropriate host for the development of high performance deep-blue PHOLEDs.

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Section: Resultsmentioning

confidence: 94%

High Efficiency Deep‐Blue Phosphorescent Organic Light‐Emitting Diodes with CIE x, y (≤ 0.15) and Low Efficiency Roll‐Off by Employing a High Triplet Energy Bipolar Host Material

Maheshwaran

Sree

Park

et al. 2018

Adv Funct Materials

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124

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“…1 H NMR (CDCl 3 , 400 MHz): δ 3.78 (s, 3H), 6.73 (dd, J = 6.8, 2.8 Hz, 2H), 6.77 (dd, J = 6.8, 2.8 Hz, 2H), 6.97−7.01 (m, 4H), 7.22 (td, J = 7.6, 1.2 Hz, 2H), 7.58 (dd, J = 7.6, 1.6 Hz, 2H). 13 C NMR (CDCl 3 , 100 MHz): δ 55. 4, 114.3, 121.5, 123.7, 125.7, 128.2, 128.5, 134.5, 141.1, 146.2, 155.1.…”

Section: Discussionmentioning

confidence: 99%

Palladium-Catalyzed Annulation of Phenazastannines with 9-(Dibromomethylene)fluorene and -(thio)xanthenes: Facile Synthesis of Acridine Moiety-Containing Bis(tricyclic) Aromatic Enes

Shimizu

Nishimura

Mineyama

et al. 2019

Org. Process Res. Dev.

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Growing interest has been paid to bis-(tricyclic) aromatic enes as key components of functional organic materials such as molecular switches and chargetransporting materials. Currently, the synthetic approaches to the overcrowded alkenes are limited to McMurry coupling and Barton−Kellog olefination. This communication reports that palladium-catalyzed double cross-coupling reaction of phenazastannines with 9-(dibromomethylene)fluorene, -xanthene, -thioxanthene, and -thioxanthene-S,S-dioxide serves as a facile synthetic approach to bis(tricyclic) aromatic enes such as 9-(9Hfluoren-9-ylidene)acridines, 9-(9H-oxanthen-9-ylidene)acridines, 9-(9H-thioxanthen-9-ylidene)acridines, and 9-(10,10-dioxido-9H-thioxanthen-9-ylidene)acridines.

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“…In recent years, sulfone was introduced as an electron-accepting building block in luminescent materials for organic light-emitting diodes (OLEDs) [27][28][29][30][31][32][33][34][35] . The structure of diphenyl sulfone has also been applied [36][37][38][39][40][41] .…”

Section: Formation Of Intramolecular Dimer Radical Ions Of Diphenyl Smentioning

confidence: 99%

Formation of intramolecular dimer radical ions of diphenyl sulfones

Okamoto

Kawai

Kozawa

2020

Sci Rep

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Dimer radical ions of aromatic molecules in which excess charge is localized in a pair of rings have been extensively investigated. While dimer radical cations of aromatics have been previously produced in the condensed phase, the number of molecules that form dimer anions is very limited. In this study, we report the formation of intramolecular dimer radical ions (cations and anions) of diphenyl sulfone derivatives (DPs) by electron beam pulse radiolysis in the liquid phase at room temperature. The density functional theory (DFT) calculations also showed the formation of the dimer radical ions. The torsion barrier of the phenyl ring of DPs was also calculated. It was found that the dimer radical ions show the larger barrier than the neutral state. Finally, stability of the dimer radical anion is dependent on not only the inductive effect of the sulfonyl group but the conjugation involving the d-orbital of the S atom and the phenyl rings.

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Blue phosphorescent organic light-emitting devices based on carbazole/thioxanthene-S,S-dioxide with a high glass transition temperature

Abstract: A bipolar host material for blue organic light-emitting devices was synthesized by incorporating electron-donating carbazole and electron-accepting thioxanthene-S,S-dioxide into one molecule using a solventless green reaction.

Cited by 29 publications

References 54 publications

High Efficiency Deep‐Blue Phosphorescent Organic Light‐Emitting Diodes with CIE x, y (≤ 0.15) and Low Efficiency Roll‐Off by Employing a High Triplet Energy Bipolar Host Material

High Efficiency Deep‐Blue Phosphorescent Organic Light‐Emitting Diodes with CIE x, y (≤ 0.15) and Low Efficiency Roll‐Off by Employing a High Triplet Energy Bipolar Host Material

Palladium-Catalyzed Annulation of Phenazastannines with 9-(Dibromomethylene)fluorene and -(thio)xanthenes: Facile Synthesis of Acridine Moiety-Containing Bis(tricyclic) Aromatic Enes

Formation of intramolecular dimer radical ions of diphenyl sulfones

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