Synthesis and electroluminescent properties of 9,10-diphenylanthracene containing 9H-carbazole derivatives for blue organic light-emitting diodes

Lee, Seul Bee; Park, Soo Na; Kim, Chanwoo; Lee, Hyun Woo; Lee, Ho Won; Kim, Young Kwan; Yoon, Seung Soo

doi:10.1016/j.synthmet.2015.02.037

Cited by 23 publications

(5 citation statements)

References 17 publications

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Section: Nh-heterocyclesmentioning

confidence: 99%

“…The resulting tetradentate species formed Pt(II) complexes used to prepare red phosphorescent OLEDs. Similarly, Kim, Yoon, and and their co-workers were able to couple δ-carboline 538 and 7-bromo-9,10-diphenylanthracene under comparable reaction conditions using an L12 -based catalyst and NaO- t -Bu in toluene (Scheme b) …”

Section: Nh-heterocyclesmentioning

confidence: 99%

“…Similarly, Kim, Yoon, and and their co-workers were able to couple δ-carboline 538 and 7-bromo-9,10-diphenylanthracene under comparable reaction conditions using an L12-based catalyst and NaO-t-Bu in toluene (Scheme 133b). 454 High molecular weight compounds could also be prepared using C−N coupling reactions with carbazole-type molecules (Scheme 134). Cyclic phosphazene dendrimer (539, Scheme 134a), a host material for blue and green OLEDs, was prepared in this manner by Sellingerand co-workers.…”

Section: Carbazolementioning

confidence: 99%

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Nh-heterocyclesmentioning

confidence: 99%

Section: Nh-heterocyclesmentioning

confidence: 99%

Section: Carbazolementioning

confidence: 99%

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…Among them, organic materials owing to their low cost, easy synthesis, and functionalization have attracted more attention in recent years . DPA is a novel organic luminescent material, whose excellent optical property is inseparable from the unique “butterfly” configuration. , The anthracene ring in DPA molecule plays a role as the axis, which is connected with the benzene rings to form two wings of “butterfly” configuration, this unique structure manifestly increased the steric hindrance of molecular. Owing to the presence of benzene rings and CC of olefin in DPA, the interacting π orbitals in conjugated molecules show lower electron energy levels, contributing to the transition of electrons from the ground state to excited states. − To obtain better luminescence characteristics, enhance the luminescence quantum yield, and reduce photon leakage, DPA CNPs were synthesized by the reprecipitation method.…”

Section: Introductionmentioning

confidence: 99%

Aggregation-Induced Electrochemiluminescence Immunosensor Based on 9,10-Diphenylanthracene Cubic Nanoparticles for Ultrasensitive Detection of Aflatoxin B₁

Miao

et al. 2020

ACS Appl. Bio Mater.

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9,10-Diphenylanthracene cubic nanoparticles (DPA CNPs) with aggregation-induced emission characteristic (AIEgens) were synthesized through a facile reprecipitation method; then, a bright and stable electrochemiluminescence (ECL) signal can be observed when the DPA CNPs were modified at the glassy carbon electrode (GCE) in the presence of Tri-n-propylamine (TPA). This phenomenon is ascribed to the molecules with restricted movement that greatly blocked the energy leakage during the relaxation of the excited state, which facilitated the emission of energy in the form of photons. In addition, the size confinement effect of DPA CNPs in the aggregated state effectively enhanced the ECL emission. The application of DPA CNPs with AIE characteristics in an electrochemiluminescence immunosensor has not been reported. In this contribution, a free-label aggregation-induced electrochemiluminescence immunosensor based on DPA CNPs was fabricated and a simple strategy for ultrasensitive detection of aflatoxin B1 (AFB1) was proposed. The ECL signal is quenched linearly in the range of 0.01 pg/mL to 100 ng/mL for AFB1, and the detection limit is 3 fg/mL. In summary, the prepared sensor exhibits high sensitivity, acceptable accuracy, good anti-interference ability and stability, and satisfactory detection toward AFB1 in walnut samples. Therefore, the fabricated immunosensor will have significant applications in the fields of food, medicine, and so on.

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“…In these materials, the diphenylamine moieties have the good electron-donating capabilities and thus improve hole injection and hole-transporting ability in emitting layer. 16,17) Furthermore, the additional bulky t-butyl groups may prevent the self-aggregation by reducing intermolecular interaction. [18][19][20] Therefore, the OLED device using these newly designed compounds as emitting materials would be expected to exhibit the improved EL efficiencies.…”

Section: Introductionmentioning

confidence: 99%

N-(4-tert-Butylphenyl)-N-phenyl-4-(9,10-diphenylanthracen-3-yl)benzenamine for blue organic light-emitting diodes

Kim

Lee

et al. 2016

Jpn. J. Appl. Phys.

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In this study, we have synthesized two blue fluorescent materials based on anthracene derivatives with electron-donating diphenylamine moieties by Suzuki cross-coupling reactions. To explore their electroluminescent properties as blue emitting materials, multilayer devices were fabricated in following sequence: indium–tin-oxide (180 nm)/4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (50 nm)/blue emitters (30 nm)/bathophenanthroline (30 nm)/lithium quinolate (2 nm)/Al (100 nm). Among them, a device using N-(4-tert-butylphenyl)-N-phenyl-4-(9,10-diphenylanthracen-3-yl)benzenamine exhibited efficient blue emission with a luminous, power and external quantum efficiency of 3.11 cd/A, 2.39 lm/W, and 1.82% at 20 mA/cm2, respectively. The Commission International de L’Eclairage coordinates of this device were at 6.0 V.

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Synthesis and electroluminescent properties of 9,10-diphenylanthracene containing 9H-carbazole derivatives for blue organic light-emitting diodes

Cited by 23 publications

References 17 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Aggregation-Induced Electrochemiluminescence Immunosensor Based on 9,10-Diphenylanthracene Cubic Nanoparticles for Ultrasensitive Detection of Aflatoxin B₁

N-(4-tert-Butylphenyl)-N-phenyl-4-(9,10-diphenylanthracen-3-yl)benzenamine for blue organic light-emitting diodes

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Synthesis and electroluminescent properties of 9,10-diphenylanthracene containing 9H-carbazole derivatives for blue organic light-emitting diodes

Cited by 23 publications

References 17 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Aggregation-Induced Electrochemiluminescence Immunosensor Based on 9,10-Diphenylanthracene Cubic Nanoparticles for Ultrasensitive Detection of Aflatoxin B1

N-(4-tert-Butylphenyl)-N-phenyl-4-(9,10-diphenylanthracen-3-yl)benzenamine for blue organic light-emitting diodes

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Product

Resources

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Aggregation-Induced Electrochemiluminescence Immunosensor Based on 9,10-Diphenylanthracene Cubic Nanoparticles for Ultrasensitive Detection of Aflatoxin B₁