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A kind of heterotrinuclear metal organic alkyne complex and its preparation method and application

A metal-organic and complex technology, applied in platinum-based organic compounds, platinum-group organic compounds, organic chemistry, etc., can solve the problems of shortage of iridium resources, incomplete chromaticity, high price, etc., and achieve the improvement of electroluminescence efficiency of devices. Effect

Active Publication Date: 2021-11-05
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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Problems solved by technology

The current commercial luminescent materials for OLEDs are mainly phosphorescent ring metal iridium(III) complexes, whose energy utilization efficiency can reach 100%, but there are challenging problems such as high price, incomplete chromaticity (lack of blue phosphorescent materials), and shortage of iridium resources.

Method used

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  • A kind of heterotrinuclear metal organic alkyne complex and its preparation method and application
  • A kind of heterotrinuclear metal organic alkyne complex and its preparation method and application
  • A kind of heterotrinuclear metal organic alkyne complex and its preparation method and application

Examples

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Effect test

Embodiment 1

[0065] Example 1: Pt 2 Complex Pt 2 (PPh 3 ) 4 (μ-decz)(C≡CPh) 2 preparation of

[0066] Add Pt(PPh 3 ) 2 (C≡CPh)Cl (180mg, 0.21mmol), cuprous iodide (1mg), triethylamine (1mL) were reacted at 50°C for 18 hours. A clear yellow solution was obtained. After the reaction solution was concentrated, the product was purified by silica gel column chromatography, using petroleum ether-dichloromethane (2:1) as the eluent to collect a light yellow product with a yield of 78%. Elemental Analysis C 112 h 93 NP 4 Pt 2 Calculated: C, 68.39; H, 4.77. Measured: C, 68.14; H, 4.82. High resolution mass m / z (%): 1967.5549 (100) [M+H] +(calculated value 1967.5627). H NMR spectrum (400MHz, CD 2 Cl 2 ,ppm):7.85-7.77(m,24H),7.60(m,2H),7.32(t,24H,J=7.36),7.24(t,12H,J=7.32),6.94-6.88(m 6H), 6.73-6.70(m,2H),6.69(s,1H),6.30-6.22(m,4H),1.29(s,18H). Nuclear Magnetic Resonance Phosphorus Spectrum (162MHz,CD 2 Cl 2 ,ppm): 17.9(J Pt-P =2641Hz). Infrared spectrum (KBr, cm -1 ):2109m(C≡C). ...

Embodiment 2

[0067] Example 2: Pt 2 Complex Pt 2 (PPh 3 ) 4 (μ-decz)(C≡C-(9-Ph-carb-3)) 2 preparation of

[0068] The preparation method is basically the same as the method in Example 1, using Pt(PPh 3 ) 2 (C≡C-(9-Ph-carb-3)Cl instead of Pt(PPh 3 ) 2 (C≡CPh)Cl, productive rate: 72%. Elemental analysis C 136 h 107 N 3 P 4 Pt 2 Calculated: C, 71.10; H, 4.69. Measured: C, 70.99; H, 4.81. High-resolution mass spectrum m / z (%): 2297.6781 (100) [M+H] + (calculated value 2297.6793). H NMR spectrum (CD 2 Cl 2 ,ppm):7.95-7.80(m,24H),7.64-7.53(m,6H),7.51-7.39(m,12H),7.39-7.32(m,24H),7.31-7.21(m,12H),6.97 (d, 2H, J=8.48), 6.85(s, 1H), 6.74(s, 2H), 6.33(d, 2H, J=8.44), 1.29(s, 18H). Nuclear Magnetic Resonance Phosphorus Spectrum (162MHz, CD 2 Cl 2 ,ppm): 18.0(J Pt-P =2645Hz). Infrared spectrum (KBr, cm -1 ):2117(w).

Embodiment 3

[0069] Example 3: Pt 2 Complex Pt 2 (PPh 3 ) 4 (μ-debf)(C≡CPh) 2 preparation of

[0070] The preparation method is basically the same as the method in Example 1, using debf-2H to replace decz-2H, productive rate: 70%. Elemental analysis C 104 h 76 OP 4 Pt 2 Calculated: C, 67.31; H, 4.13. Measured: C, 67.21; H, 4.08. High-resolution mass spectrum m / z (%): 1854.4132 (100) [M+H] + (calculated value 1854.4140). H NMR spectrum (CD 2 Cl 2 ,ppm):7.72-7.68(m,26H),7.61-7.57(m,4H),7.36-7.32(m,26H),7.27-7.24(m,14H),6.97-6.92(t,2H,J= 8.38), 6.53-6.51(d, 2H, J=8), 6.46-6.45(d, 2H, J=8.38). Nuclear Magnetic Resonance Phosphorus Spectrum (162MHz, CD 2 Cl 2 ,ppm): 17.77(J Pt-P =2134Hz). Infrared spectrum (KBr, cm -1 ):2110(w).

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Abstract

The invention belongs to the technical field of luminescent materials and organic light emitting diodes, in particular to a phosphorescent Pt 2 M (M=Au(I), Ag(I), Cu(I)) heterotrinuclear metal organic alkyne complexes, their synthesis methods and their applications as phosphorescent materials in organic light-emitting diodes. The heterotrinuclear organometallic alkyne complex represented by the formula (I) of the present invention has strong phosphorescent emission in solution, solid and film. The invention utilizes phosphorescent Pt for the first time 2 The M heterotrinuclear metal organic alkyne complex is used as a light-emitting material to assemble an organic light-emitting device. The organic light-emitting diode prepared by using the heterotrinuclear organic alkyne complex of the invention as the dopant of the light-emitting layer has high-efficiency electroluminescence, and the external quantum conversion efficiency (EQE) is higher than 12.5%.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials and organic light emitting diodes, in particular to a phosphorescent Pt 2 M (M=Au(I), Ag(I), Cu(I)) heterotrinuclear metal organic alkyne complexes, their synthesis methods and their applications as phosphorescent materials in organic light-emitting diodes. Background technique [0002] Organic light-emitting diode (OLED) is a thin-film light-emitting device, which generally includes a multi-layer organic thin film interlayer such as a light-emitting layer between its cathode and anode electrodes, which can convert electrical energy into light energy under the action of a low driving voltage (3-12V). Luminescence has a very broad application prospect in the field of flat panel display and lighting. The core of organic light-emitting diodes is light-emitting thin-film materials. The breakthrough of light-emitting materials is also the key to the realization of high-efficiency electro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C07F19/00C09K11/06H01L51/54H01L51/56
CPCC07F15/0086C07F19/00C09K11/06C09K2211/185C09K2211/188H10K85/6576H10K85/6574H10K85/657H10K85/371H10K85/346H10K85/6572H10K71/00H10K85/361H10K50/11
Inventor 陈忠宁肖晖张续王金云
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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