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Phosphorescent PtM<2> (M = Cu, Ag and Au) complex and organic light emitting diode thereof

A technology of complexes and metal complexes, which is applied in the fields of compounds, luminescent materials, organic chemistry, etc. containing elements of Group 8/9/10/18 of the periodic table, which can solve the problems of difficult solution printing and film formation, and achieve strong phosphorescence. The effect of the launch

Active Publication Date: 2020-11-10
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&lt;2&gt; (M = Cu, Ag and Au) complex and organic light emitting diode thereof
  • Phosphorescent PtM&lt;2&gt; (M = Cu, Ag and Au) complex and organic light emitting diode thereof
  • Phosphorescent PtM&lt;2&gt; (M = Cu, Ag and Au) complex and organic light emitting diode thereof

Examples

Experimental program
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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 a preparation method and application thereof. The structure of the complex is represented by a general formula (I) as shownin the specification. In the formula (I), R1 and R2 are the same or different, and are independently selected from alkyl, aryl and heteroaryl groups; the alkyl, aryl and heteroaryl groups are optionally substituted by the group consisting of halogen, an alkyl group, an alkoxy group, an alkylthio group, an amino group, an alkylamino group, a dialkylamino group, an arylamino group, a diarylamino group, a halogenated alkyl group, a cyano group, a nitro group, an alkenyl group, an aryl group and a heteroaryl group optionally substituted by 1 to 3 aryl groups; R3 is one optionally selected from thegroup consisting of halogen, an alkyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an amino group, an alkylamino group, a dialkylamino group, a cyano group, a nitro group, an alkenyl group and the like; and M is optionally selected from Cu (I), Ag (I) and Au (I). The invention further relates to an organic light-emitting diode and a preparation method and application thereof. The organic light-emitting diode prepared by taking the phosphorescent metal complex as a light-emitting layer dopant has high-performance organic electroluminescence and can be applied to illuminationand 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 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 Applications(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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