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High-performance organic light-emitting diode

A light-emitting diode, organic technology, applied in the direction of light-emitting materials, organic chemistry, platinum group organic compounds, etc., can solve the problem of not breaking 16%, restricting the commercial application of related devices, etc., to reduce the preparation cost, improve the energy transfer efficiency, high The effect of electro-optical conversion efficiency

Active Publication Date: 2016-04-13
GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electroluminescent external quantum efficiency of organic light-emitting diodes based on ionic phosphorescent metal complexes has not broken through 16%, which greatly restricts the commercial application of related devices in flat panel display and lighting.

Method used

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  • High-performance organic light-emitting diode

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: Complex [PtAu 2 (dpmp) 2 (C≡C-2-(9-Ph)carb) 2 ](ClO 4 ) 2 (1) Preparation

[0047] [Au(tht) was dissolved in 20mL 2 ]ClO 4 (47.3mg, 0.1mmol) in dichloromethane solution was added Ph 2 P(CH 2 PPh 2 ) 2 (50.6 mg, 0.1 mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡C-2-(9-Ph)carb) 2 (62.5mg, 0.05mmol) in dichloromethane (5mL). The reaction solution turned yellow-green after being stirred at room temperature for 4 hours. The product was purified by silica gel column chromatography using CH 2 Cl 2 -MeCN(8:1) was the eluent to collect the yellow-green product. Yield: 83%. Elemental analysis (C 104 h 82 Au 2 Cl 2 N 2 o 8 P 6 Pt) Calculated: C, 53.53; H, 3.54; N, 1.20. Measured: C, 53.86; H, 3.62; 4 ] + ,1066.5(28)[M-2ClO 4 ] 2+ .Proton NMR spectrum (CDCl 3 ,ppm):8.18-8.14(d,2H,J=7.9Hz),7.96-7.92(d,2H,J=7.9Hz),7.87-7.79(m,6H),7.78-7.66(m,10H), 7.65-7.48(m,18H),7.47-7.41(t,6H,J=7.4Hz),7.39-7.29(m,6H),7.28-7.21(m,4H),7.20-7.06(m,...

Embodiment 2

[0048] Embodiment 2: Complex [PtAu 2 (dpmp) 2 (C≡C-3-(9-Ph)carb) 2 ](ClO 4 ) 2 (2) Preparation.

[0049] The preparation method is basically the same as the method in Example 1, only using Pt(PPh 3 ) 2 (C≡C-3-(9-Ph)carb) 2 Instead of Pt(PPh 3 ) 2 (C≡C-2-(9-Ph)carb) 2 . Yield: 85%. Elemental analysis (C 104 h 82 Au 2 Cl 2 N 2 o 8 P 6 Pt 1 / 2CH 2 Cl 2 ) Calculated: C, 52.82; H, 3.52; N, 1.18. Measured: 52.76; H, 3.37; N, 1.24. Electrospray mass spectrum (%): 2233.4 (100) [M-ClO 4 ] + ,1067.2(46)[M-2ClO 4 ] 2+ . H NMR spectrum (CDCl 3 ,ppm):8.04-7.90(m,10H),7.75-7.65(m,12H),7.64-7.57(m,18H),7.55-7.51(m,10H),7.47-7.40(m,12H),7.30 -7.24(t, 4H, J=7.9Hz), 7.14-7.07(t, 6H, J=7.3Hz), 6.86-6.80(m, 2H), 5.48-5.34(m, 4H), 4.63-4.47(m ,4H). Nuclear Magnetic Resonance Phosphorus Spectrum (CDCl 3 ,ppm):31.2(m,2P,J P-P =30.3Hz), 6.0(m,1P,J P-P =30.2Hz,J Pt-P = 2562Hz). Infrared spectrum (KBr, cm -1 ): 2098(w), 1100(s).

Embodiment 3

[0050] Embodiment 3: Complex [PtAu 2 (dpmp) 2 (C≡C-4-(9-Ph)carb) 2 ](ClO 4 ) 2 (3) Preparation.

[0051] The preparation method is basically the same as the method in Example 1, only using Pt(PPh 3 ) 2 (C≡C-4-(9-Ph)carb) 2 Instead of Pt(PPh 3 ) 2 (C≡C-2-(9-Ph)carb) 2 . The obtained product was dissolved in dichloromethane, n-hexane was slowly added dropwise to the solution, and the product was crystallized at room temperature and kept in the dark for 5 days. Yield: 80%. Elemental analysis (C 104 h 82 Au 2 Cl 2 N 2 o 8 P 6 P·C 6 h 14 ) calcd: C, 54.60; H, 4.00; N, 1.16. Measured values: C, 54.83; H, 3.92; N, 1.08. Electrospray mass spectrum m / z (%): 2233.3 (100) [M-ClO 4 ] + ,1067.1(37)[M-2ClO 4 ] 2+ . H NMR spectrum (CDCl 3 ,ppm):8.11-8.05(d,2H,J=8.0Hz),7.86-7.80(m,8H),7.70-7.65(m,10H),7.44-7.38(m,18H),7.37-7.30(m ,20H),6.96-6.86(m,10H),6.60-6.53(t,4H,J=7.5Hz),6.52-6.48(s,2H),5.23-4.98(m,4H),4.14-4.00(m ,4H). Phosphorus NMR spectrum (CDCl 3 ,ppm...

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Abstract

The invention relates to an ionic phosphorescent metal complex, and a preparation method and application thereof. The structure of the complex is as shown in a general formula (I) which is described in the specification. In the general formula (I), R1 and R2 are same or different and are independently selected from a group consisting of aryl-substituted heteroaryl groups; M is any one selected from the group consisting of Ag(I) and Au(I); A<n-> is ClO4<-->, Pf6<-->, SbF6<-->, BF4<--> and SiF6<2-->; and n is 1 or 2. The invention also relate to an organic light-emitting diode and a preparation method and application thereof. The organic light-emitting diode is prepared with the phosphorescent metal complex as a doping body of a luminescent layer, has high-performance organic electroluminescence and maximum external quantum efficiency of up to 20% and can be applied to panel display.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence and can be applied to the fields of color flat panel display and illumination. Specifically, it relates to the preparation of an organic light-emitting diode based on a phosphorescent metal organic alkyne complex by a solution method, and obtains high-efficiency organic electroluminescence. Background technique [0002] Organic electroluminescence is a light-emitting phenomenon in which an organic light-emitting diode (OLED) directly converts electrical energy into light energy under the action of a low DC voltage of 3-12V. It has very broad applications in the fields of flat panel display and lighting. Compared with traditional lighting and display technologies, organic electroluminescence has many advantages such as full-color display, wide viewing angle, high definition, fast response, low power consumption, and low temperature resistance; and organic light-emitting devices have simpl...

Claims

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Application Information

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IPC IPC(8): C07F19/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0006C09K2211/185H10K85/346
Inventor 陈忠宁徐亮金王金云曾宪崇
Owner GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD
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