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Tetradentate ONCN platinum complex containing multi-nitrogen heterocyclic ring

A platinum complex, nitrogen heterocycle technology, applied in the field of OLED materials, can solve the problems of difficult molecular purification of divalent platinum complexes, easy to be attacked by halogen, unfavorable materials, etc., to enhance electron cloud density, increase steric hindrance, improve The effect of binding capacity

Pending Publication Date: 2022-07-15
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, OLED devices based on metal platinum complexes have been greatly developed, but due to the planar structure of its molecules, compared with the three-dimensional six-coordinated metal iridium, the four-coordinated divalent metal platinum is exposed outside, resulting in Solve the problems of divalent platinum complex molecular purification, difficult sublimation, easy to be attacked by halogens, etc., which is not conducive to the commercialization of materials

Method used

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  • Tetradentate ONCN platinum complex containing multi-nitrogen heterocyclic ring
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  • Tetradentate ONCN platinum complex containing multi-nitrogen heterocyclic ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of complex 3

[0033]

[0034] Synthesis of intermediate B: In a 250ml three-necked flask, add compound A (12g, 50mmol), dissolve in 100ml of anhydrous tetrahydrofuran, install a constant pressure dropping funnel, evacuate nitrogen three times, and stir at -78°C for 30 minutes. Take n-butyllithium (29.9ml, 2.5M) into a constant pressure dropping funnel, slowly drop it into the reaction solution, and stir at the same temperature for 30 minutes after all drops are completed. Take isopropanol pinacol borate (13.9g, 75mmol) into the reaction solution, then move the whole reactor to normal temperature and stir for 1 hour, after the reaction is finished, the water layer is separated and filtered off, and the organic phase is filtered through anhydrous sulfuric acid. After sodium drying, rotary evaporation was performed to obtain 10.5 g of white powder B with a yield of 72.83%.

[0035] Synthesis of intermediate D: in a 250ml single-necked flask, add i...

Embodiment 2

[0041] Example 2: Synthesis of complex 11

[0042]

[0043] Synthesis of intermediate J: in a 250ml single-necked flask, add intermediate E (10.0g, 17.27mmol), compound I (7.6g, 51.80mmol), tetrakistriphenylphosphine palladium (0.50g, 0.86mmol), anhydrous Potassium phosphate (11.4g, 43.17mmol), 160ml of toluene / ethanol / water=5 / 2 / 1 mixed solution was used as the reaction solvent, stirred in an oil bath at 50°C under nitrogen protection for 16 hours, after the reaction was completed, 100ml of water and 50ml of After extraction with ethyl acetate three times, the organic phase was dried over anhydrous sodium sulfate and then chromatographed on silica gel column (the chromatographic solution was n-hexane:ethyl acetate=10:1). The crude product obtained was concentrated, stirred and crystallized with 50 ml of methanol to obtain 8.40 g of white Solid J, yield 86.70%. Hydrogen nuclear magnetic spectrum: 1H NMR (400MHz, CDCl3) δ9.06 (d, J=0.8Hz, 1H), 8.82 (s, 1H), 8.31 (d, J=7.8Hz,...

Embodiment 3

[0051] Under a nitrogen atmosphere, weigh about 5.0 mg of fully dried samples of platinum complexes 3 and 11 respectively, set the heating scanning speed to 10 °C / min, the scanning range is 25-800 °C, and the measured thermal decomposition temperatures are 383.74 °C, 419.71°C (the temperature corresponding to 0.5% thermal weight loss), indicating that this type of complex has very good thermal stability.

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Abstract

The invention relates to a tetradentate ONCN platinum complex containing a multi-nitrogen heterocyclic ring. The structural formula of the tetradentate ONCN platinum complex is shown as a formula (I). According to the compound, the electron cloud density of molecules is dispersed through introduction of multi-nitrogen heterocyclic rings, so that neat arrangement of the molecules is avoided in the purification process. Compared with a previous pyridine structure, the compound has higher electron cloud density, on one hand, the coordination binding capacity is improved, the molecular stability is improved, and on the other hand, the electron cloud density near metal platinum on a mother ring is enhanced, so that high-efficiency luminous efficiency is obtained, groups of R1-R5 on a right benzene ring increase the steric hindrance of molecules, and the luminous efficiency is improved. The intermolecular aggregation effect is effectively reduced.

Description

technical field [0001] The invention relates to the field of OLED materials, in particular to a tetradentate ONCN platinum complex containing nitrogen heterocycle on the parent ligand Background technique [0002] Organic Light Emitting Diodes (OLEDs) have the advantages of self-luminescence, high color purity, low startup voltage, fast response speed, and the ability to prepare flexible displays. They have become a new generation of display technology and are currently mainly used in high-end display panels. The general device mainly includes cathode and anode, electron transport material, light-emitting layer material, hole transport material and is prepared by layer-by-layer evaporation, and the material of the light-emitting layer is the core material of the whole device. [0003] Platinum(II) complexes have d 8 Metal orbitals, whose coordination is a planar four-coordination structure, have triplet phosphorescence lifetimes comparable to those of metal iridium complexe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0086C09K11/06C09K2211/185H10K85/346H10K50/11H10K50/12H10K85/00C07F15/00
Inventor 吴信蔚刘宇谭庭钊戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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