Novel aromatic extended carbazoles as a chemical platform of bipolar hosts for improved lifetime in phosphorescent organic light-emitting diodes

Kim, Sung Moo; Yun, Ju Hui; Han, Si Hyun; Lee, Jun Yeob

doi:10.1016/j.jiec.2019.12.036

Cited by 4 publications

(7 citation statements)

References 28 publications

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“…Instrumentation: 1 H, 13 C, and 11 B NMR spectra were recorded on a Bruker Avance III 300 (Bruker, 301 MHz for 1 H), a Bruker Avance DRX 300 (Bruker, 300 MHz for 1 H, and 75 MHz for 13 C), a Bruker Avance III 400 (Bruker, 400 MHz for 1 H,101 MHz for 13 C, and 128 MHz for 11 B), a Bruker Avance III 500 (Bruker, 500 MHz for 1 H, and 126 MHz for 13 C), a Bruker Avance III 600 (Bruker, 600 MHz for 1 H and 151 MHz for 13 C), or a Bruker Avance Neo 700 (Bruker, 700 MHz for 1 H and 176 MHz for 13 C). CDCl 3 (Sigma Aldrich, 99.8 %), CD 2 Cl 2 (Sigma Aldrich, 99.5 %), or (CD 3 ) 2 CO (Sigma Aldrich, 99.5 %) were used to dissolve the samples.…”

Section: Methodsmentioning

confidence: 99%

“…2H),7.95 (d,J = 8.2 Hz,2H),7.76 (d,J = 8.2 Hz,2H),7.47 (ddd,J = 8.1,6.9,1.1 Hz,2H),2H),7.33 (ddd,J = 8.3,6.8,1.2 Hz,2H),7.19 (ddd,J = 8.9,7.1,1.6 Hz,4H),2H),1.26 (s,9H) ppm. 13 C NMR (101 MHz, (CD 3 ) 2 CO) δ 149. 1, 146.2, 144.6, 138.0, 136.3, 131.1, 129.5, 128.7, 127.0, 126.7, 126.3, 125.5, 125.0, 121.4, 34.7, 31.8 ppm.…”

Section: N-(4-tert-butylphenyl)-n-(naphthalen-1-yl)naphthalen-1-aminementioning

confidence: 99%

“…22-7.14 (m, 2H), 7.00 (d, J = 8.0 Hz, 2H), 6.75-6.66 (m, 2H), 1.27 (s, 9H) ppm. 13 C NMR (75 MHz, CD 2 Cl 2 ) δ 148. 0, 145.7, 145.4, 133.7, 131.6, 130.4, 128.1, 127.9, 127.4, 126.4, 125.4, 125.1, 121.6, 119.5, 34.5, 31.…”

Section: N-(4-tert-butylphenyl)-n-(naphthalen-1-yl)naphthalen-1-aminementioning

confidence: 99%

“…45-7.42 (m, 2H), 7.39-7.36 (m, 2H), 7.35 (d, J = 8.0, 2H), 7.32-7.29 (m, 4H), 7.26-7.23 (m, 2H), 6.75-6.74 (m, 2H), 1.41 (s, 18H), 1.27 (s, 9H) ppm. 13 C NMR (151 MHz, (CD 3 ) 2 CO) δ 153.7, 149. 1, 146.1, 146.0, 144.77, 144.75, 137.0, 135.7, 134.4, 134.3, 132.8, 131.0, 128.4, 127.4, 127.3, 127.2, 127.0, 126.8, 125.4, 125.03, 124.96, 124.9, 121.6, 121.5, 35.4, 34.7, 31.7, 31.5 ppm.…”

Section: -(4-tert-butyl-2-chlorophenyl)-n-[4-(4-tert-butyl-2-chloroph...mentioning

confidence: 99%

“…[12] The structurally related compound 2 was implemented as a hole transport material with improved stability in OLEDs by Lee and coworkers. [13] Only recently, structurally appealing corannulene-carbazole hybrids such as 3 were disclosed by Tanaka and coworkers. [14] However, in spite of this indisputable progress π-expanded carbazoles incorporating cyclopentannulated all-carbon polycyclic moieties still remain scarce.…”

Section: Introductionmentioning

confidence: 99%

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A Symmetrically π‐Expanded Carbazole Incorporating Fluoranthene Moieties

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A novel doubly cyclopentannulated carbazole which is accessible through a successive π‐expansion of di(1‐naphthylamine) is disclosed. The carbazole moiety is generated in the final step through intramolecular oxidative coupling. The π‐expansion of carbazole resulted in strongly altered optoelectronic and electrochemical properties. The solid‐state structure features an interesting packing motif with alternating face‐to‐face π⋅⋅⋅π and edge‐to‐face C−H⋅⋅⋅π interactions. The experimental findings were corroborated by theoretical calculations.

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Section: Methodsmentioning

confidence: 99%

Section: N-(4-tert-butylphenyl)-n-(naphthalen-1-yl)naphthalen-1-aminementioning

confidence: 99%

Section: N-(4-tert-butylphenyl)-n-(naphthalen-1-yl)naphthalen-1-aminementioning

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Section: -(4-tert-butyl-2-chlorophenyl)-n-[4-(4-tert-butyl-2-chloroph...mentioning

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Section: Introductionmentioning

confidence: 99%

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Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Söderberg

Berkowitz

2022

Organic Reactions

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This chapter presents a comprehensive review of reductive cyclizations of 2‐nitro‐ and β‐nitrostyrenes, 2‐nitrobiphenyls, and 1‐nitro‐1,3‐dienes to furnish indoles, carbazoles, and pyrroles, respectively, as well as heteroatom analogs thereof. Two variations of the reductive cyclization are discussed: the Cadogan–Sundberg reaction, which is mediated by ternary phosphorus compounds, and the Watanabe–Cenini–Söderberg reaction, which employs a palladium catalyst in the presence of carbon monoxide. A few closely related reductive cyclizations are also presented, as are comparisons with other cyclizations that form the nitrogen–carbon bond of indoles and derivatives.

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Functional Carbazole‐Fullerene Complexes: A New Perspective of Carbazoles Acting as Nano‐Octopus to Capture Globular Fullerenes

Liu

Wang

Fan

et al. 2021

Chemistry A European J

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Fullerene host-guest constructs have attracted increasing attention owing to their molecular-level hybrid arrangements. However, the usage of simple carbazolic derivatives to bind with fullerenes is rare. In this research, three novel carbazolic derivatives, containing a tunable bridging linker and carbazole units for the capturing of fullerenes, are rationally designed. Unlike the general concave-convex interactions, fullerenes could interact with the planar carbazole subunits to form 2-dimensional hexagonal/ quadrilateral cocrystals with alternating stacking patterns of 1 : 1 or 1 : 2 stoichiometry, as well as the controllable fullerene packing modes. At the meanwhile, good electron-transporting performances and significant photovoltaic effects were realized when a continuous C 60••• C 60 interaction channel existed. The results indicate that the introduction of such carbazolic system into fullerene receptor would provide new insights into novel fullerene host-guest architectures for versatile applications.

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Novel aromatic extended carbazoles as a chemical platform of bipolar hosts for improved lifetime in phosphorescent organic light-emitting diodes

Cited by 4 publications

References 28 publications

A Symmetrically π‐Expanded Carbazole Incorporating Fluoranthene Moieties

A Symmetrically π‐Expanded Carbazole Incorporating Fluoranthene Moieties

Reductive Cyclization of 2‐Nitro‐ and β‐Nitrostyrenes, 2‐Nitrobiphenyls, and 1‐Nitro‐1,3‐Dienes to Indoles, Carbazoles, and Pyrroles

Functional Carbazole‐Fullerene Complexes: A New Perspective of Carbazoles Acting as Nano‐Octopus to Capture Globular Fullerenes

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