2,6-Diphenylpyridine-based organic emitter for electroluminescent device

Zuo, Jin-Lin; Yang, Jiaxiang; Wang, Fu-Zhi; Dang, Xiangnan; Sun, Jiasen; Zou, Dechun; Tian, Yupeng; Lin, Na; Tao, Xiaofeng; Jiang, Minhua

doi:10.1016/j.jphotochem.2008.06.013

Cited by 9 publications

(2 citation statements)

References 28 publications

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“…In many cases, phenylamine groups can be employed as electron donors, and be linked with an electron-acceptor group to form Dp-A-type molecules (D = donor, A = acceptor), a property that is regarded as ideal for high-performance nonlinear optical (NLO) materials. [9] Recently, our group [10] has synthesized a number of phenylamine derivatives with linear, second-order, and/or third-order NLO properties to study the correlation between the structure and linear/nonlinear optical properties. Our previous work provided a basis for molecular design with high NLO activity.…”

Section: Introductionmentioning

confidence: 99%

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

Kong

Yang

et al. 2013

Chemistry A European J

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A fluorophore-phenylamine derivative (L) has been coupled with silver nanocrystals (NCs) to construct an L-Ag nanohybrid. Owing to synergic effects of the L and Ag components, the exciton-plasmon interactions between L and Ag increase the strength of the donor-acceptor interaction within the nanohybrid, a fact that results in an energy-transfer process and further brings about a dramatic redshift of single-photon absorption and fluorescence, and a decreased fluorescence FL lifetime. The coupling effect also leads to enhancement of a series of nonlinear optical properties, including two-photon-excited fluorescence (TPEF), two-photon-absorption (TPA) cross section (δ), two-photon-absorption coefficient (β), nonlinear refractive index (γ), and third order nonlinear optical susceptibility (χ((3))). The enhanced two-photon fluorescence of the nanohybrid is proven to be potentially useful for two-photon microscopy of live cells, such as HepG2. Moreover, cytotoxicity tests show that the low-micromolar concentrations of the nanohybrid do not cause significant reduction in cell viability over a period of at least 24 h and should be safe for further biological studies.

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Section: Introductionmentioning

confidence: 99%

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

Kong

Yang

et al. 2013

Chemistry A European J

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“…Bebq 2 is a electron-transporting host material which has a high electron mobility of about 10 -4 cm 2 /V-sec and narrow a band-gap energy of about 2.7 eV. [7][8][9] Good electron-transport and energy-transfer characteristics of Bebq 2 and good hole-injection characteristics of 2-TNATA makes it possible to develop a moderate-efficiency redemitting bi-layered device. However, a luminance and efficiency high enough to be applicable in industrial applications have not yet been reported for bi-layered devices.…”

Section: Introductionmentioning

confidence: 99%

High‐efficiency red‐phosphorescent organic light‐emitting diode with the organic structure of 2‐TNATA/Bebq²:SFC‐411/SFC‐137

Jang

Kim

2010

J Soc Info Display

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Abstract— High‐efficiency and simple‐structured red‐emitting phosphorescent devices based on the hole‐injection layer of 4,4′,4″‐tris(2‐naphthylphenyl‐phenylamino)‐triphenylamine [2‐TNATA] and the emissive layer of bis(10‐hydroxybenzo[h] quinolinato)beryllium complex [Bebq2] doped with SFC‐411 (proprietary red phosphorescent dye) have been researched. The fabricated devices are divided into three types depending on whether or not the hole‐transport layer of N,N′‐bis(1 ‐naphthyl)‐N, N'‐diphenyl‐1,1′‐biphenyl‐4,4′‐diamine [NPB] or the electron‐transport layer of SFC‐137 (proprietary electron transporting material) is included. Among the experimental devices, the best electroluminescent characteristics were obtained for the device with an emission structure of 2‐TNATA/Bebq2:SFC‐411/SFC‐137. In this device, current density and luminance were found to be 200 mA/cm2 and 15,000 cd/m2 at an applied voltage of 7 V, respectively. Current efficiencies were 15 and 11.6 cd/A under a luminance of 500 and 5000 cd/m2. The peak wavelength in the electroluminescent spectral distribution and color coordinates on the Commission Internationale de I'Eclairage (CIE) chart were 628 nm and (0.67, 0.33), respectively.

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Iron‐Catalyzed Aerobic Oxidative Cleavage and Construction of C−N Bonds: A Facile Method for Synthesis of 2,4,6‐Trisubstituted Pyridines

et al. 2018

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Abundant and inexpensive iron, readily catalyzed the oxidative tandem reactions of arylalkylketones and benzylamines using molecular oxygen as the green oxidant in one-pot solvent-free conditions. 2,4,6-Triaryl pyridines containing a wide variety of functional groups are synthe-sized from easily available starting materials. The synthetic importance of this reaction protocol has been demonstrated by preparing topoisomerase I and II inhibitors, and other valuable pyridine derivatives. Key intermediates are isolated and a plausible mechanism has been proposed.[a] Prof. -(1,3-Benzodioxol-5-yl)-2,6-diphenylpyridine (4 j). Yield: 67%, pale yellow solid, Melting point: 151-152°C (Lit.: 152-153°C); [25] 1 H NMR (400 MHz, CDCl 3 ) δ 8.21-8.18 (m, 4H), 7.82 (s, 2H), 7.54-7.49 (m, 4H), 7.47-7.43 (m, 2H), 7.27-7.23 (m, 2H), 6.96 (d, J = 7.6 Hz, 1H), 6.06 (s, HRMS (ESI, m/z): calcd for C 24 H 17 NO 2 [M + H] + 352.1332, found 352.1336. 4-(1-Naphthaylenyl)-2,6-diphenylpyridine (4 k). Yield: 85%, white crystalline solid, Melting point: 133-134°C (Lit.: 134-135°C); [24] 1 H NMR (400 MHz, CDCl 3 ) δ 8.22 (d, J = 6.8 Hz, 4H), 7.96 (d, J = 8.4 Hz, 2H), 7.85 (s, 2H), 7.61-7.57 (m, 2H), 7.55-7.49 (m, 7H), 7.46-7.43 (m, HRMS (ESI, m/z): calcd for C 27 H 19 N [M + H] + 358.1590, found 358.1592. 2,6-Diphenyl-4-(thiophen-2-yl)pyridine (4 l). Yield: 87%, white solid, Melting point: 162-163°C (Lit.: 162-164°C); [22] 1 H NMR (400 MHz, CDCl 3 ) δ 8.29-8.26 (m, 4H), 7.94 (s, 2H), 7.67-7.66 (m,1H), 7.64-7.59 (m, 4H), 7.57-7.53 (m, 2H), 7.49-7.48 (m, 1H), 7.24-7.22 (m, 1H); 13 C HRMS (ESI, m/z): calcd for C 21 H 15 NS [M + H] + 314.0448, found 314.1000. 4-(Furan-2-yl)-2,6-diphenylpyridine (4 m). Yield: 74%, white solid, Melting point: 168-169°C (Lit.: 170-171°C); [24] 1 H NMR (400 MHz, CDCl 3 ) δ 8.21-8.18 (m, 4H), 7.94 (s, 2H), 7.59 (d, J = 2.0 Hz, 1H), 7.54-7.49 (m, 4H), 7.47-7.42 (m, 2H), 6.99-6.98 (m, 1H), 6.58 (dd, J = 3.6, 2.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 157. 5, 151.9, 143.6, 139.4, 139.0, 129.1, 128.7, 127.0, 112.9, 112.1,108.5; HRMS (ESI, m/z): calcd for C 21 H 15 NO [M + H] + 298.1226, found 298.1227.

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2,6-Diphenylpyridine-based organic emitter for electroluminescent device

Cited by 9 publications

References 28 publications

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

High‐efficiency red‐phosphorescent organic light‐emitting diode with the organic structure of 2‐TNATA/Bebq²:SFC‐411/SFC‐137

Iron‐Catalyzed Aerobic Oxidative Cleavage and Construction of C−N Bonds: A Facile Method for Synthesis of 2,4,6‐Trisubstituted Pyridines

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2,6-Diphenylpyridine-based organic emitter for electroluminescent device

Cited by 9 publications

References 28 publications

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

A Self‐Assembled Nanohybrid Composed of Fluorophore–Phenylamine Nanorods and Ag Nanocrystals: Energy Transfer, Wavelength Shift of Fluorescence and TPEF Applications for Live‐Cell Imaging

High‐efficiency red‐phosphorescent organic light‐emitting diode with the organic structure of 2‐TNATA/Bebq2:SFC‐411/SFC‐137

Iron‐Catalyzed Aerobic Oxidative Cleavage and Construction of C−N Bonds: A Facile Method for Synthesis of 2,4,6‐Trisubstituted Pyridines

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High‐efficiency red‐phosphorescent organic light‐emitting diode with the organic structure of 2‐TNATA/Bebq²:SFC‐411/SFC‐137