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Rigid triphosphine-supported phosphorescent Pt-M complex and organic light emitting diode thereof

A technology of light-emitting diodes and complexes, applied in the fields of light-emitting materials, organic chemistry, platinum group organic compounds, etc., can solve the problems of lack of exploration, limited research on phosphorescent multi-nuclear complexes, etc., and achieve the effect of strong phosphorescence emission

Active Publication Date: 2020-11-24
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, compared with a large variety of phosphorescent mononuclear metal complexes, the current research on phosphorescent multinuclear complexes and their OLED applications is very limited, and there is a lack of systematic and in-depth exploration

Method used

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  • Rigid triphosphine-supported phosphorescent Pt-M complex and organic light emitting diode thereof
  • Rigid triphosphine-supported phosphorescent Pt-M complex and organic light emitting diode thereof
  • Rigid triphosphine-supported phosphorescent Pt-M complex and organic light emitting diode thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: Complex [PtAu 2 (dBpimp) 2 (C≡CC 6 h 3 (OMe) 2 -2,4) 2 ](CF 3 SO 3 ) 2 (1) Preparation

[0058] [Au(tht) was dissolved in 20mL 2 ](CF 3 SO 3 ) (0.1 mmol) in dichloromethane solution was added dBpimp (0.1 mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡CC 6 h 3 (OMe) 2 -2,4) 2 (0.05 mmol) in dichloromethane (5 mL), and the reaction solution was 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 collected as eluent to give pure product. Yield: 26%. High resolution mass spectrometry [M-2CF 3 SO 3 ] 2+ Calculated value: 958.1268, Measured value: 958.1256. H NMR spectrum (CD 2 Cl 2 ,ppm):8.78-8.75(m,4H),8.15-8.10(m,4H),7.98-7.90(m,10H),7.78-7.74(t,4H),7.68-7.64(t,4H),7.55 -7.51(m,4H),7.39-7.33(m,6H),7.02-7.00(m,8H),6.75-6.73(m,2H),6.52-6.51(d,2H),4.96-4.89(m, 4H), 4.00-3.85(m, 10H), 3.63(s, 6H). Phosphorus NMR spectrum (CD 2 Cl 2 ,ppm):20.28(...

Embodiment 2

[0059] Embodiment 2: Complex [Pt 2 Au(dBpimp) 2 (C≡CC 6 h 5 ) 4 ](CF 3 SO 3 ) (2) preparation.

[0060] [Au(tht) was dissolved in 20mL 2 ](CF 3 SO 3 ) (0.05mmol) in dichloromethane solution was added dBpimp (0.1mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡CC 6 h 6 ) 2 (0.1 mmol) in dichloromethane (5 mL). The reaction solution turned orange 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 orange product. Yield: 80%. High resolution mass spectrometry [M-ClO 4 ] + Calculated value: 1996.2882, Measured value: 1996.2880. H NMR spectrum (CD 2 Cl 2 ,ppm):8.82-8.79(m,4H),8.16-8.14(m,4H),7.88-7.81(m,8H),7.72-7.69(t,2H),7.63-7.59(t,4H),7.51 -7.35(m,16H),7.31-27(m,2H),7.21-7.13(m,14H),6.85-6.81(m,4H),6.62-6.60(m,4H),4.32-4.25and 3.52- 3.48(m,8H). Phosphorus NMR spectrum (CD 2 Cl 2 ,ppm):-2.95(m,2P,J Pt–P =2618Hz,J P–P =26.78Hz)...

Embodiment 3

[0061] Embodiment 3: Complex [Pt 2 Au(dBpimp) 2 (C≡CC 6 h 3 (OMe) 2 -2,4) 4 ](ClO 4 ) (3) preparation.

[0062] [Au(tht) was dissolved in 20mL 2 ]ClO 4 (0.05 mmol) in dichloromethane was added dBpimp (0.1 mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡CC 6 h 3 (OMe) 2 -2,4) 2 (0.1 mmol) in dichloromethane (5 mL). The reaction solution turned orange 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 orange product. Yield: 80%. High resolution mass spectrometry [M-ClO 4 ] + Calculated: 2236.3728, Measured: 2236.3727. H NMR spectrum (CD 2 Cl 2 ,ppm):8.81-8.78(m,4H),8.07-8.06(m,4H),7.86-7.78(m,8H),7.57-7.53(m,6H),7.43-7.31(m,16H),7.06 -7.04(d,2H),6.78-6.75(m,4H),6.66-6.64(d,2H),6.46-6.45(d,2H),6.35-6.33(m,2H),6.22(br,2H) , 6.17-6.14 (m, 2H), 4.51-4.48 (m, 8H), 3.91-3.82 (m, 12H), 3.56-3.42 (m, 16H). Phosphorus NMR spectrum (CD 2...

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Abstract

The invention relates to a rigid triphosphine-supported phosphorescent Pt-M complex and a preparation method and application thereof. The structure of the complex is shown as a general formula (I) and / or a general formula (II) (please see the specification for the formulas), wherein R1 and R2 are the same or different; wherein R1 and R2 are independently selected from aryl, heteroaryl and heteroaryl aryl, and the heteroaryl and aryl are optionally substituted by 1-5 of the following groups: alkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, arylamino, diarylamino, halogen, haloalkyl, cyano, nitro, alkenyl, alkynyl, aryl and heteroaryl optionally substituted by 1-3 aryls; and wherein M is optionally selected from Cu (I), Ag (I) and Au (I), A<n-> is ClO4<->, CF3SO3<->, PF6<->, SbF6<->, BF4<->, SiF6<2-> and the like, and n is 1 or 2. The invention further relates to an organic light emitting diode and a preparation method and application thereof, the ionic phosphorescent Pt-M complex is used as a light-emitting layer dopant, and the prepared organic light emitting diode has high-performance organic electroluminescence and can be applied to illumination and 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. It specifically relates to a Pt-M complex phosphorescent material supported by a rigid triphosphine ligand and its application in an organic light-emitting diode. A high-efficiency organic light-emitting diode based on a phosphorescent Pt-M complex is prepared by a solution method. Background technique [0002] An organic light emitting diode (OLED) is a device with a sandwich structure consisting of an anode, a luminescent film and a cathode, which can convert electricity into light under the action of a low DC voltage of 3-12V, that is, organic electroluminescence. Compared with the first-generation display technology represented by cathode ray tube (CRT) and the second-generation display technology represented by plasma (PDP) and liquid crystal (LCD), OLED, as the core of the third-generation display techno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0086C09K11/06C09K2211/185C09K2211/188H10K85/346H10K85/371H10K50/11
Inventor 陈忠宁张礼仪施林熙王金云王兆亿
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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