- 1,5-naphthyridine organic light-emitting compound and synthetic method and application thereof
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The invention discloses a 4,8-substituted 1,5-naphthyridine derivative blue-light organic photoelectric material, which comprises the following ingredients: 4,8-dibenzyl-1,5-naphthyridine, 4,8-di(4-trifluoromethylphenyl)-1,5-naphthyridine, 4,8-di(4-phenoxylphenyl)-1,5-naphthyridine, 4,8-di(2-(9,9-n-butylfluorenyl)-1,5-naphthyridine and 4,8-di(4-(dibenzylamino)phenyl)-1,5-naphthyridine. The maximum UV absorption wavelength of the compound is within the range of 294-399 nm, the largest fluorescence emission spectrum is within the range of 521-434 nm, and half-peak width is about 70 nm. The compound is an ideal potential blue-light organic photoelectric material.
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Paragraph 0049; 0050; 0051
(2017/06/02)
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- Novel multifunctional organic semiconductor materials based on 4,8-substituted 1,5-naphthyridine: Synthesis, single crystal structures, opto-electrical properties and quantum chemistry calculation
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A series of 4,8-substituted 1,5-naphthyridines (1a-1h) have been successfully synthesised by a Suzuki cross-coupling between 4,8-dibromo-1,5- naphthyridine (4) and the corresponding boronic acids (2a-2h) in the presence of catalytic palladium acetate in yields of 41.4-75.8% and have ben well characterized. They are thermally robust with high phase transition temperatures (above 186 °C). Compounds 1b, 1e and 1f crystallized in the monoclinic crystal system with the space groups P21/c, P21/c and P21/n, respectively. All of them show the lowest energy absorption bands (λmaxAbs: 294-320 nm), revealing low optical band gaps (2.77-3.79 eV). These materials emit blue fluorescence with λmaxEm ranging from 434-521 nm in dilute solution in dichloromethane and 400-501 nm in the solid state. 4,8-Substituted 1,5-naphthyridines 1a-1h have estimated electron affinities (EA) of (2.38-2.72 eV) suitable for electron-transport materials and ionization potentials (IP) of 4.85-5.04 eV facilitate excellent hole-injecting/hole-transport materials properties. Quantum chemical calculations using DFT B3LYP/6-31G* showed nearly identical the lowest unoccupied molecular orbitals (LUMO) of -2.39 to -2.19 eV and the highest occupied molecular orbitals (HOMO) of -5.33 to -6.84 eV. These results demonstrate the 4,8-substituted 1,5-naphthyridines 1a-1h with a simple architecture might be promising blue-emitting (or blue-green-emitting) materials, electron-transport materials and hole-injecting/hole-transport materials for applications for developing high-efficiency OLEDs.
- Wang, Kun-Yan,Chen, Chen,Liu, Jin-Fang,Wang, Qin,Chang, Jin,Zhu, Hong-Jun,Li, Chong
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p. 6693 - 6704
(2012/09/22)
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