Rational design of quinoxaline-based bipolar host materials for highly efficient red phosphorescent organic light-emitting diodes

Feng, Zilong; Gao, Zhixiang; Qu, Wenshan; Yang, Tingting; Li, Jiangang; Wang, Lixiong

doi:10.1039/c9ra01149h

Cited by 13 publications

(2 citation statements)

References 43 publications

(52 reference statements)

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“…Apart from biomedicine, quinoxaline derivatives have a crucial role to play as pesticides, herbicides [11], and insecticides [12]. Additionally, they can be utilized in high‐efficiency phosphorescent light‐emitting diodes [13] and solar cells [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Abdelwadoud,

Gomaa,

Geies

2023

Journal of Heterocyclic Chem

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In this paper, we present the synthesis of new selenoloquinoxaline derivatives starting from 2‐chloroquinoxaline‐3‐carbonitrile 1. The compound 1 was subjected to a reaction with selenium metal in the presence of NaBH4 as a reducing agent in ethanol, under a nitrogen atmosphere. This reaction resulted in the formation of the sodium salt of 3‐cyanoquinoxaline‐2‐selenolate, which was subsequently reacted with α‐halogenated carbonyl compounds in situ. This reaction produced a series of newly synthesized 3‐aminoselenolo[2,3‐b]quinoxaline‐2‐substituents. Ethyl 3‐aminoselenolo[2,3‐b]quinoxaline‐2‐carboxylate 3a was hydrolyzed by sodium hydroxide to give the corresponding sodium salt 9. This salt was then refluxed with acetic anhydride to produce oxazinone compound 10. The reaction of compound 10 with ammonium acetate afforded pyrimidoselenolo[2,3‐b]quinoxaline derivative 11. Compound 11 was then chlorinated using phosphorous oxychloride to give the corresponding chlorocompound.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Abdelwadoud,

Gomaa,

Geies

2023

Journal of Heterocyclic Chem

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“…Moreover, bipolar host materials can provide proper carrier balance while supporting an effective carrier recombination at the emission layer [53][54][55][56][57]. Mostly, bipolar materials can be utilized for host materials as well as fluorescent emitters.…”

Section: Introductionmentioning

confidence: 99%

Fluorene–Triphenylamine-Based Bipolar Materials: Fluorescent Emitter and Host for Yellow Phosphorescent OLEDs

et al. 2020

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In this study, two new bipolar materials were designed and synthesized: N1-(9,9-diphenyl-9H-fluoren-2-yl)-N1-(4,6-diphenylpyrimidin-2-yl)-N4,N4-diphenylbenzene-1,4-diamine (FLU-TPA/PYR) and N1-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-N1-(9,9-diphenyl-9H-fluoren-2-yl)-N4,N4 diphenylbenzene-1,4-diamine (FLU-TPA/TRZ). We fabricated two different devices, namely a yellow phosphorescent organic light-emitting diode (PhOLED) and a non-doped fluorescent OLED emitter with both FLU-TPA/PYR and FLU-TPA/TRZ. The FLU-TPA/PYR host-based yellow PhOLED device showed better maximum current, power and external quantum efficiencies at 21.70 cd/A, 13.64 lm/W and 7.75%, respectively. The observed efficiencies were better than those of the triazine-based FLU-TPA/TRZ. The non-doped fluorescent device with the triazine-based FLU-TPA/TRZ material demonstrated current, power and external quantum efficiencies of 10.30 cd/A, 6.47 lm/W and 3.57%, respectively.

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Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics

et al. 2023

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Quinoxaline has recently gained interest as monomer in conjugated copolymers because of its easy synthetic accessibility and successful use in highly efficient organic solar cells. In this contribution, we introduce a quinoxaline–fluorene-co-polymer, PFQ10, synthesized by copolymerization of 5,8-dibromo-6,7-difluoro-2-[(2-hexyldecyl)oxy]quinoxaline and 9,9-dioctyl-9H-9-fluorene-2,7-bis(boronic acid pinacol ester) using the Suzuki–Miyaura reaction. By optimization of the reaction conditions, polymers with molecular weights up to 17.2 kDa and a low dispersity of 1.3 were obtained. PFQ10 showed blue photoluminescence with an emission maximum at 459 nm and a relative fluorescence quantum yield of 0.37. As proof of principle, PFQ10 was employed in organic light-emitting diodes and showed a blue–green electroluminescence. Graphical abstract

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Rational design of quinoxaline-based bipolar host materials for highly efficient red phosphorescent organic light-emitting diodes

Abstract: Two novel bipolar carbazole/diphenylquinoxaline-based host materials 3-(2,3-diphenylquinoxalin-6-yl)-9-phenyl-9H-carbazole (M1) and 3-(4-(2,3-diphenylquinoxalin-6-yl)phenyl)-9-phenyl-9H-carbazole (M2) have been rationally designed and synthesized.

Cited by 13 publications

References 43 publications

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Synthesis and characterizations of some new selenolo[2,3‐b]quinoxaline derivatives

Fluorene–Triphenylamine-Based Bipolar Materials: Fluorescent Emitter and Host for Yellow Phosphorescent OLEDs

Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics

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