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Ionic type phosphorescent Ag6Cu complex and its preparation method and use

A complex and ion-type technology, applied in the field of preparation of organic light-emitting diodes, can solve problems such as incomplete chromaticity, high price, and shortage of iridium resources, and achieve high electrical-optical conversion efficiency and excellent performance.

Inactive Publication Date: 2016-04-20
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are challenging problems such as high price, incomplete chromaticity (lack of blue phosphorescent materials), shortage of iridium resources, and difficulty in preparing large-scale devices.

Method used

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  • Ionic type phosphorescent Ag6Cu complex and its preparation method and use
  • Ionic type phosphorescent Ag6Cu complex and its preparation method and use
  • Ionic type phosphorescent Ag6Cu complex and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0053] Embodiment 1: Complex [Ag 6 Cu{CH(PPh 2 ) 3} 2 (Ph 2 PO 2 ) 3 (C≡CC 6 h 4 Bu t -4) 3 ](ClO 4 )(1) Preparation

[0054] CH(PPh was dissolved in 30mL 2 ) 3 (56.8mg, 0.1mmol) in dichloromethane solution was added 4-tert-butyl phenylacetylene silver (AgC≡CC 6 h 4 Bu t -4) n (79.5 mg, 0.3 mmol). After stirring for 15 minutes, [Cu(MeCN) 4 ](ClO 4 ) (16.4mg, 0.05mmol) and diphenylphosphonic acid (32.7mg, 0.15mmol). The reaction solution turned into a bright yellow solution after being stirred at room temperature for 4 hours. After filtration, the filtrate was concentrated to 3 mL, and 10 mL of petroleum ether was slowly added dropwise to the concentrated liquid, and yellow crystals were obtained after standing for a week. Yield: 61%. Elemental analysis (C 146 h 131 Ag 6 ClCuO 10 P 9 ) Calculated: C, 57.11; H, 4.30. Measured: C, 56.94; H, 4.19. Electrospray mass spectrometry m / z (%): 2971.3 [M-ClO 4 ] + . Nuclear Magnetic Resonance Phosphorus Spectr...

Embodiment 2

[0055] Embodiment 2: Complex [Ag 6 Cu{CH(PPh 2 ) 3} 2 (Ph 2 PO 2 ) 3 (C≡CC 6 h 4 CF 3 -4) 3 ](ClO 4 ) (2) preparation.

[0056] The preparation method is basically the same as the method in Example 1, only using 4-trifluoromethyl phenylacetylene silver (AgC≡CC 6 h 4 CF 3 -4) n Substitute for 4-tert-butylphenylacetylene silver (AgC≡CC 6 h 4 Bu t -4) n . Yield: 63%. Elemental analysis (C 137 h 104 Ag 6 ClCuF 9 o 10 P 9 ) Calculated value: C, 52.97; H, 3.37. Measured value: C, 52.78; H, 3.41. Electrospray mass spectrum (%): 3006.4 [M-ClO 4 ] + . H NMR spectrum (CD 2 Cl 2 ,ppm):8.04-7.92(m,24H),7.83-7.65(m,10H),7.32-7.26(m,8H),7.26-7.13(m,18H),7.01(t,12H,J=7.4Hz ), 6.70(t, 24H, J=7.4Hz), 6.58-6.54(m, 6H), 5.62-5.46(m, 2H). Nuclear Magnetic Resonance Phosphorus Spectrum (CD 2 Cl 2 ,ppm):22.4(s,3P,Ph 2 PO 2 ),13.3(m,6P,CH(PPh 2 ) 3 ,J Ag-P =571Hz,J P-P = 35Hz). Infrared spectrum (KBr, cm -1 ):2041w(C≡C),1097s(ClO 4 ).

Embodiment 3

[0057] Embodiment 3: Complex [Ag 6 Cu{CH(PPh 2 ) 3} 2 (Ph 2 PO 2 ) 3 (C≡C-9-Phcarb-2) 3 ](ClO 4) (3) preparation.

[0058] The preparation method is basically the same as the method in Example 1, only using 9-phenylcarbazole-2-acetylene silver (AgC≡C-9-Phcarb-2) n Substitute for 4-tert-butylphenylacetylene silver (AgC≡CC 6 h 4 Bu t -4) n . Yield: 65%. Elemental analysis (C 170 h 128 Ag 6 ClCuN 3 o 10 P 9 ) Calculated: C, 60.09; H, 3.80, N, 1.24. Measured values: C, C, 59.91; H, 3.70; N, 1.27. Electrospray mass spectrum m / z(%): 3297.0[M-ClO 4 ] + . H NMR spectrum (CD 2 Cl 2 ,ppm):8.10-7.98(m,30H),7.75-7.67(m,14H),7.29-7.23(m,8H),7.16-7.09(m,22H),7.00(t,16H,J=6.8Hz ), 6.75-6.63 (m, 30H), 6.34 (d, 6H, J=8.6Hz), 5.63-5.52 (m, 2H). Phosphorus NMR spectrum (CD 2 Cl 2 ,ppm):21.5(s,3P,Ph 2 PO 2 ),12.0(m,6P,CH(PPh 2 ) 3 ,J Ag-P =561Hz,J P-P = 36Hz). Infrared spectrum (KBr, cm -1 ):2011w(C≡C),1095s(ClO 4 ).

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Abstract

The invention relates to an ionic type phosphorescent Ag6Cu complex and its preparation method and use. The ionic type phosphorescent Ag6Cu complex has a structural formula of [Ag6Cu{HC(PPh2)3}2(C[triple-bond]CR)3{Ph2P(=X)X}3]<+>A<n->1 / n, wherein X represents the same or different groups of O, S and Se, R represents the same or different groups of aryl, heterocyclic aryl and -aryl-heterocyclic aryl, the heterocyclic aryl and aryl can be replaced through one or more substituents, the substituents are respectively selected from alkyl, alkenyl, alkynyl, alkyloxy, amino, halogen, halogenated alkyl and aryl, and A<n-> represents ClO<4->, PF<6->, SbF<6->, BF<4-> or SiF6<2-> and n is 1 or 2. The invention also relates to an organic light-emitting diode and its preparation method and use. The phosphorescent metal complex is a doped luminescent layer. The prepared organic light-emitting diode produces high performance organic electroluminescence and can be used for 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 related to a class of Ag 6 Cu heteroheptanuclear metal-organic alkyne complexes for the preparation of organic light-emitting diodes. 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 simple structure, ultra-light, ultra-thin , flexible and foldable and...

Claims

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Application Information

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IPC IPC(8): C07F9/50C09K11/06H01L51/54
Inventor 陈忠宁徐亮金王金云舒辉星
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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