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A High Performance Organic Light Emitting Diode

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

Active Publication Date: 2018-07-17
GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD
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  • Summary
  • 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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  • A High Performance Organic Light Emitting Diode
  • A High Performance Organic Light Emitting Diode
  • A 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 present invention relates to an ionic phosphorescent metal complex and its preparation method and application. The structure of the complex is shown in general formula (I), wherein R1 and R2 are the same or different, independently selected from: aryl substituted The heteroaryl group, M is optionally: Ag(I), Au(I), An for ClO4-, PF6-, SbF6-, BF4-, SiF62-, etc., n is 1,2. The present invention also relates to an organic light-emitting diode and its preparation method and application. The organic light-emitting diode prepared by using the phosphorescent metal complex described in the present invention as a light-emitting layer dopant has high-performance organic electroluminescence, The maximum external quantum efficiency breaks through 20%, which can be applied to flat 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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Patent Type & Authority Patents(China)
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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