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phosphorescent ptm 2 (m = Cu, Ag, Au) complexes and their organic light-emitting diodes

A technology of light-emitting diodes and complexes, applied in the field of novel PtM2 heterotrinuclear complex light-emitting materials and organic light-emitting diodes, can solve the problems of difficult solution printing and film formation, and achieve improved energy transfer efficiency, improved luminous color purity, maximum The effect of high current efficiency

Active Publication Date: 2022-02-18
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Electroneutral iridium(III) complexes are easy to evaporate in vacuum and are suitable for vacuum coating to prepare OLEDs, but it is difficult to form films by solution printing due to solubility problems

Method used

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  • phosphorescent ptm <sub>2</sub> (m = Cu, Ag, Au) complexes and their organic light-emitting diodes
  • phosphorescent ptm <sub>2</sub> (m = Cu, Ag, Au) complexes and their organic light-emitting diodes
  • phosphorescent ptm <sub>2</sub> (m = Cu, Ag, Au) complexes and their organic light-emitting diodes

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: Complex [PtAu 2 (dTolmp) 2 (C≡CC 6 h 3 (OMe) 2 -2,4) 2 ](CF 3 SO 3 ) 2 (1) Preparation

[0063] [Au(tht) was dissolved in 20mL 2 ](CF 3 SO 3 ) (0.1 mmol) in dichloromethane was added dTolmp (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). The reaction 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: 83%. High resolution mass spectrometry [M-2CF 3 SO 3 ] 2+ Calculated value: 1018.2208, measured value: 1018.2207. H NMR spectrum (CD 2 Cl 2 ,ppm):8.12-8.09(m,4H),7.77-7.72(m,4H),7.37-7.31(m,8H),7.18-7.14(m,14H),6.98-6.91(m,8H),6.76 -6.72(t,4H),6.67-6.65(d,2H),6.43-6.37(m,4H),5.04-5.01(m,8H),3.90,3.86(s,12H),2.22, 2.13(s, 24H). Nuclear Magnetic Resonance Phosphorus Spectrum (CD 2 Cl 2 ,ppm):20.28(m,4P,J P–P =33.10Hz), 8.24...

Embodiment 2

[0064] Embodiment 2: Complex [PtAg 2 (dTolmp) 2 (C≡C-4-TPA) 2 ](ClO 4 ) 2 (2) Preparation.

[0065] [Ag(tht)](ClO 4 ) (0.1 mmol) in dichloromethane was added dTolmp (0.1 mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡C-4-TPA) 2 (0.05 mmol) in dichloromethane (5 mL). The reaction 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: 78%. High resolution mass spectrometry [M-2ClO 4 ] 2+ Calculated value: 1036.2117, measured value: 1036.2098. H NMR spectrum (CD 2 Cl 2 , ppm):8.12-7.90(m,7H),7.65-7.58(m,4H),7.46-6.94(m,44H),6.88-6.58(m,12H), 6.39-6.25(m,3H),6.66 -6.62(t,2H),6.59-6.56(m,3H),6.43-6.41(d,1H),6.22-6.16(m,3H),4.73-4.04(m,8H),2.16-2.01(m, 24H). Nuclear Magnetic Resonance Phosphorus Spectrum (CD 2 Cl 2 ,ppm): 12.94,11.50(m,2P,J Pt–P =2442Hz,J Pt–P =2407Hz,J P–P =33.3Hz), -12.25, -16.10, -19.32 (m, 4P, J Ag–P ...

Embodiment 3

[0066] Embodiment 3: Complex [PtAg 2 (dTolmp) 2 (C≡C-4-Ph-9-Carb) 2 ](CF 3 SO 3 ) 2 (3) Preparation.

[0067] [Ag(tht)](ClO 4 ) (0.1 mmol) in dichloromethane was added dTolmp (0.1 mmol). After stirring for 30 minutes, Pt(PPh 3 ) 2 (C≡C-4-Ph-9-Carb) 2 (0.05 mmol) in dichloromethane (5 mL). The reaction 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: 80%. High resolution mass spectrometry [M-2CF 3 SO 3 ] 2+ Calculated value: 1034.1960, measured value: 1034.1960. H NMR spectrum (CD 2 Cl 2 ,ppm):8.26-8.17(m,11H),7.83-7.71(m,4H),7.58-7.32(m,24H), 7.29-7.05(m,18H),7.00-6.93(m,4H),6.87 -6.73(m,4H),6.56-6.54(d,1H), 4.98-4.27(m,8H),2.31-2.12(m,24H). NMR phosphorous spectrum (CD 2 Cl 2 ,ppm): 12.93and 12.03(m,2P,J Pt–P =2431Hz,J Pt–P =2386Hz,J P–P =33.2Hz), -12.39, -16.31, -19.52 (m, 4P, J Ag–P =522Hz,J P–P =43.5Hz). Infrar...

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Abstract

The present invention relates to an ionic phosphorescent metal complex and its preparation method and use. The structure of the complex is shown in general formula (I), wherein, R 1 and R 2 The same or different, independently selected from: alkyl, aryl, heteroaryl; said alkyl, aryl, heteroaryl are optionally substituted by 1-5 of the following groups: halogen, alkyl, alkoxy , alkylthio, amino, alkylamino, dialkylamino, arylamino, diarylamino, haloalkyl, cyano, nitro, alkenyl, aryl, optionally substituted by 1-3 aryl groups The heteroaryl; R 3 Optionally halogen, alkyl, haloalkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, cyano, nitro, alkenyl, etc.; M is optionally: Cu(I), Ag(I), Au(I). 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 the light-emitting layer dopant has high-performance organic electroluminescence, and can be applied for lighting and flat panel displays.

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 the new type of PtM 2 The (M=Cu, Ag, Au) heterotrinuclear complex light-emitting material and its organic light-emitting diode obtain 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, the biggest advantage of OLED is active self-illumination. It not only has many advantages such as full-color display, wide viewing angle, high definition, fast response, low power consumption, and low temperature resistance, but also or...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C07F15/00C09K11/06H01L51/50H01L51/56H01L51/54H10K99/00
CPCC07F15/0086C09K11/06C09K2211/185C09K2211/1029C09K2211/1092C09K2211/1059C09K2211/1007C09K2211/1014C09K2211/1048H10K85/346H10K50/12H10K71/00C09K11/02C07F19/00H10K85/361H10K85/371H10K50/11H10K2101/10H10K2101/90C09K2211/188
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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