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Metalloporphyrin complex and organic electroluminescent device thereof

An organic light-emitting device, metalloporphyrin technology, applied in the field of metalloporphyrin complexes and organic electroluminescent devices, can solve problems such as few literature and patent reports, achieve good thermal stability and environmental stability, luminescence High efficiency, good rigidity and flexibility

Inactive Publication Date: 2019-12-27
JILIN TEACHERS INST OF ENG & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because porphyrin has a large conjugated system of 18 π electrons, the electron mobility in its ring is very good, so most porphyrin compounds have good photoelectric properties, but metalloporphyrin complexes are used as the guest of light-emitting materials There are few literature and patent reports on doped materials

Method used

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  • Metalloporphyrin complex and organic electroluminescent device thereof
  • Metalloporphyrin complex and organic electroluminescent device thereof
  • Metalloporphyrin complex and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of compound 1

[0048]

[0049] Preparation of Compound 1-3

[0050] Benzaldehyde (4mL, 40mmol) and freshly distilled pyrrole (2.8mL, 40mmol) were slowly and continuously added dropwise to the boiling propionic acid solution, and the reaction reflux time was 0.5 hours. After cooling to room temperature, place in the refrigerator to freeze overnight, and filter the next day. The filter cake is washed several times with methanol solution to obtain a blue-purple solid, which is dried to obtain a crude product. The first purple color band was collected by dichloromethane column chromatography, and the dichloromethane was evaporated to obtain blue-purple powder crystal compound 1-3 (1.29 g, yield 23.2%).

[0051] Preparation of compound 1

[0052] Add compound 1-3 (0.2100g, 0.2mmol) and ferric nitrate hexahydrate (0.2900g, 1mmol) into 20mL N,N-dimethylformamide (DMF), reflux for half an hour, cool to room temperature, and directly add 50mL of acetone, a bri...

Embodiment 2

[0054] Preparation of compound 15

[0055]

[0056] Preparation of compound 15

[0057] Compound 15 was obtained by replacing 1-1 in Example 1 with 15-1 shown above, and 1-3 with 15-3 shown above. Mass Spectrum m / z: 1132.42 (calculated: 1132.43). Theoretical element content (%) C 80 h 60 FeN 4 : C, 84.79; H, 5.34; Fe, 4.93; N, 4.94 Measured element content (%): C, 84.78; H, 5.33; Fe, 4.92; N, 4.95. It was confirmed above that the obtained product was the target product 15.

Embodiment 3

[0059] Preparation of Compound 24

[0060]

[0061] Preparation of Compound 24

[0062] Replace 1-1 in Example 1 with 24-1 as shown above, 1-3 with 24-3 as shown above, and replace ferric nitrate hexahydrate in the reaction with manganese nitrate hexahydrate to obtain compound 24. Mass Spectrum m / z: 827.15 (calculated: 827.16). Theoretical element content (%) C 52 h 28 MnN 4 o 4 H, 3.41; Mn, 6.64; N, 6.77; O, 7.73 Measured element content (%): C, 75.46; H, 3.42; Mn, 6.63; It was confirmed above that the obtained product was the target product 24.

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Abstract

The invention provides a metalloporphyrin complex and an organic electroluminescent device thereof, and belongs to the technical field of organic photoelectric materials. The invention discloses a metalloporphyrin complex, which contains a porphyrin-containing unit and has a macrocyclic delocalized [pi] electron conjugated system with a planar structure. The quantum efficiency of charge transfer and energy transfer reactions is high, the quantum efficiency has good electron buffering performance and photoelectric magnetism, good rigidity and flexibility and good thermal stability and environmental stability, collision between triplet excitons is reduced, and the problem of roll-off of the efficiency of the device under high current density is solved. The organic light-emitting device prepared by using the complex as an object doping material has the advantages of low driving voltage and high light-emitting efficiency, and is an organic light-emitting material with excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a metal porphyrin complex and an organic electroluminescence device thereof. Background technique [0002] In the past two decades, the application of phosphorescent materials in organic electroluminescence has attracted extensive attention in the academic community. The related phosphorescent compounds include Pt(II), Pd(II), Au with planar structure and d8 electronic configuration. (III) complexes, and Ru(II), Rh(III), Re(I), Ir(III), Os(II) and other complexes with octahedral structure and d6 electron configuration. Among them, complexes of osmium, iridium, platinum, and ruthenium have been studied more. They all have better luminous efficiency and a shorter phosphorescent half-life, thereby greatly reducing the probability of non-radiative decay. The efficiency and lifetime of green and yellow organic phosphorescent materials can basically meet the re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06H01L51/50H01L51/54
CPCC07D487/22C09K11/06C09K2211/187C09K2211/188H10K85/30H10K85/331H10K85/371H10K85/381H10K50/11
Inventor 张弘杨晓东
Owner JILIN TEACHERS INST OF ENG & TECH
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