4-phosphino-1,5-naphthyridine derivative copper (i) complex luminescent material and application

A technology of naphthyridine copper and complex, applied in the field of optoelectronic materials

Inactive Publication Date: 2012-07-11
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0012] In conclusion, quinoline-based asymmetric N^P ligands are widely used in the synthesis of metal complexes such as Cu(I), Ni(I), Ru(II) and Pd(II) (J.Organomet.Chem. , 1997,535,183; Inorg.Chem., 2003,42,785.), while metal complexes based on the asymmetric N^P ligand of naphthyridine have not been reported

Method used

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  • 4-phosphino-1,5-naphthyridine derivative copper (i) complex luminescent material and application

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Embodiment 1

[0032] Embodiment 1: [Cu(ND) 2 ](PF 6 ) (1) synthesis

[0033] Under the protection of argon, 10mL CH containing ND (0.41g, 1.3mmol) 2 Cl 2 The solution was slowly added to the solution containing [Cu(NCCH 3 ) 4 ](PF 6 ) (0.24g, 0.65mmol) in 30mL methanol solution, stirred at room temperature for 2h and then filtered, and the filtrate was desolventized in vacuo to obtain a red solid. The solid was washed with ether and recrystallized from tetrahydrofuran / methanol / ether (2:1:6 v / v / v) to obtain red crystals [Cu(ND) 2 ](PF 6 ) 0.85g, yield 78%. The crystal structure of the complex is determined by X-ray single crystal diffractometer, and its crystallographic parameters are: space group P21 / C, a=14.386(3), b=23.133(5), c=23.326(5), α= 90.00, β=105.24(3), γ=90.00°,

[0034]

Embodiment 2

[0035] Embodiment 2: [Cu(mND) 2 ](PF 6 ) (2) synthesis

[0036] Under argon protection condition, 10ml CH containing mND (0.33g, 1.0mmol) 2 Cl 2 The solution was slowly added to the solution containing [Cu(NCCH 3 ) 4 ](PF 6 ) (0.19g, 0.5mmol) in 30mL of methanol solution, stirred at room temperature for 2h and then filtered, and the filtrate was desolventized in vacuo to obtain an orange solid. The solid was washed with ether and recrystallized from tetrahydrofuran / methanol / ether (2:1:6v / v / v) to obtain orange crystals [Cu(mND) 2 ](PF 6 ) 0.59g, yield 62%. The crystal structure of the complex is determined by X-ray single crystal diffractometer, and its crystallographic parameters are: space group C2 / C, a=16.242(3), b=17.274(4), c=17.517(4), α= 90.00, β=117.20(3), γ=90.00°,

[0037]

Embodiment 3

[0038] Embodiment 3: [Cu(ND)(PPh 3 ) 2 ](PF 6 ) (3) synthesis

[0039] Under argon protection condition, 15ml CH containing ND (0.55g, 1.75mmol) 2 Cl 2 The solution was slowly added to the solution containing [Cu(NCCH 3 ) 4 ](PF 6 ) (0.65g, 1.75mmol) in 35mL methanol solution, stirred at room temperature for 1h and then added triphenylphosphine (PPh 3 ) (0.92g, 3.5mmol) in 15ml CH 2 Cl 2 The solution was stirred at room temperature for 1 h and then filtered, and the solvent was removed from the filtrate in vacuo to obtain a yellow solid. The solid was washed with ether and recrystallized from tetrahydrofuran / methanol / ether (2:1:6 v / v / v) to obtain yellow crystals [Cu(ND)(PPh 3 ) 2 ](PF 6 ) 1.51g, yield 82.3%. The crystal structure of the complex is determined by X-ray single crystal diffractometer, and its crystallographic parameters are: space group P21 / c, a=12.520(3), b=16.408(3), c=26.583(5), α= 90.00, β=93.58(3), γ=90.00°,

[0040]

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Abstract

The invention provides a 4-phosphino-1,5-naphthyridine derivative copper (I) complex luminescent material and application. The copper (I) complex firstly introduces 1,5-naphthyridine to asymmetrical N^P ligand, and has lower photochemical energy gap and electrochemical energy gap as compared with typical 8-phosphino-copper oxinate (I) complex. The complex can be used as the luminescent layer or electron transmission layer of organic light-emitting diodes.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a 4-phosphino-1,5-naphthyridine derivative copper (I) complex luminescent material and its application. The compound has light-emitting properties and can be used as a light-emitting layer or an electron-transporting layer of an organic light-emitting diode. technical background [0002] In recent years, with the wide application of Organic Light-emitting diodes (OLEDs) in high-tech fields such as thin-film display and lighting, people have put forward higher requirements for the design and selection of organic light-emitting materials. Copper (I) complex luminescent materials have become a hot spot in the field of organic electroluminescence due to their low price and environmental friendliness (Annu. Rep. Prog. Chem., Sect. A, 2010, 106, 526.). [0003] In order to improve the luminescent properties of copper (I) complex luminescent materials, a lot ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00C09K11/06H01L51/54
Inventor 朱红军陈琛何广科王昆彦姜鹏施路朱晓林刘劲芳宋广亮
Owner NANJING UNIV OF TECH
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