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Platinum(ii) complex phosphorescent materials based on azapyrazole-carbazole-phenylpyridine and their applications

A phenylpyridine and azapyrazole technology, which is applied in the field of platinum complex phosphorescent materials based on azapyrazole-carbazole-phenylpyridine, can solve the problem of reduced chemical stability of complexes, low phosphorescence quantum efficiency, rigidity lower problem

Active Publication Date: 2022-05-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The rigidity of the bidentate ring metal platinum (II) complex is low, and the two bidentate ligands are easy to twist and vibrate so that the phosphorescence quantum efficiency is low (Inorg.Chem.2002, 41, 3055); although the tridentate ligand contains Cyclometallic platinum(II) complexes can increase the phosphorescent quantum efficiency of metal complexes due to the enhanced molecular rigidity (Inorg.Chem.2010, 49, 11276), but the second ligands contained (such as Cl-, phenoxy anion, alkyne anion, carbene, etc.) will reduce the chemical stability of the complex, so bidentate and tridentate ring metal platinum (II) complex phosphorescent materials are not conducive to the preparation of stable and efficient OLED devices

Method used

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  • Platinum(ii) complex phosphorescent materials based on azapyrazole-carbazole-phenylpyridine and their applications
  • Platinum(ii) complex phosphorescent materials based on azapyrazole-carbazole-phenylpyridine and their applications
  • Platinum(ii) complex phosphorescent materials based on azapyrazole-carbazole-phenylpyridine and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: The synthesis route of tetracyclic metal platinum (II) complex phosphorescent material Pt1 is as follows:

[0030]

[0031] (1) Intermediate ACzbPhNO 2 Synthesis of: Add 4'-iodo-2-nitro-1,1'-biphenyl (500mg, 4.46mmol, 1.5 equivalents), azacarbazole (1.45g, 2.97mmol, 1.0 equivalent), cuprous iodide (566mg, 2.97mmol, 10mol%), trans-1,2-cyclohexanediamine (339mg, 2.97mmol, 10mol%) and sodium tert-butoxide (600mg, 6.24 mmol, 2.1 equivalents), then the nitrogen was replaced three times, and dimethyl sulfoxide (13 mL) was added under the protection of nitrogen. Repeat the above operation three times. Stir and react the four sealed tubes in an oil bath at 110°C for 1 day, cool to room temperature, mix the four reaction solutions, add ethyl acetate for extraction, wash the organic layer twice with water, and extract the aqueous layer three times with ethyl acetate . The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solven...

Embodiment 2

[0035] Example 2: The synthetic route of tetracyclic metal platinum (II) complex phosphorescent material Pt2 is as follows:

[0036]

[0037] (1) Synthesis of ligand L (ACzCz-2): add AczCzH (350mg, 1.05mmol, 1.0eq), 4-Br (459mg, 1.58mmol, 1.5eq), three (Dibenzylideneacetone) dipalladium (38mg, 0.042mmol, 4mol%), 2-(di-tert-butylphosphine) biphenyl (25mg, 0.084mmol, 8mol%) and sodium tert-butoxide (202mg, 2.1mmol, 2.0 equivalents) and then the nitrogen was replaced three times, and toluene (15 mL) was added under the protection of nitrogen. The mixture was stirred and reacted in an oil bath at 110° C. for 3 days, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel chromatography, eluent: petroleum ether / ethyl acetate=10:1-5:1, and the product L (ACzCz-2) was obtained as a white solid 515 mg, yield 90%. 1 HNMR (400MHz, CDCl 3 ): δ1.44(s,9H),7.22(dd,J=7.2,5.2Hz,1H),7.26-7.2...

Embodiment 3

[0039] Example 3: The synthetic route of tetracyclic metal platinum (II) complex phosphorescent material Pt3 is as follows:

[0040]

[0041] (1) Synthesis of ligand L (ACzCz-3): Add AczCzH (350mg, 1.05mmol, 1.0eq), 5-Br (481mg, 1.58mmol, 1.5eq), three (Dibenzylideneacetone) dipalladium (38mg, 0.042mmol, 4mol%), 2-(di-tert-butylphosphine) biphenyl (25mg, 0.084mmol, 8mol%) and sodium tert-butoxide (202mg, 2.1mmol, 2.0 equivalents) and then the nitrogen was replaced three times, and toluene (15 mL) was added under the protection of nitrogen. The mixture was stirred and reacted in an oil bath at 110° C. for 3 days, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, eluent: petroleum ether / ethyl acetate=10:1-5:1, to obtain the product L (ACzCz-3), 512 mg of white solid, yield 90%. 1 HNMR (500MHz, DMSO-d 6 ):δ1.39(s,9H),2.37(s,3H),7.19-7.20(m,1H),7.31-...

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Abstract

The invention provides a platinum (II) complex phosphorescent material based on azapyrazole-carbazole-phenylpyridine and its application. The large conjugated phenylpyridine structural unit can reduce the lowest excited triplet state energy level of the material molecule, and develop green to red light-emitting materials, and the photophysical properties of the material can be efficiently adjusted through the regulation of the substituents on the ligand.

Description

technical field [0001] The invention relates to a phosphorescent material and its application, in particular to a platinum (II) complex phosphorescent material based on azapyrazole-carbazole-phenylpyridine and its application. Background technique [0002] Liquid crystal display requires a backlight source, which consumes a lot of energy; liquid crystal molecules are greatly affected by temperature, and there is a limitation of a narrow temperature range; in addition, components such as optical filters are required to complicate the structure of the device. In contrast, each pixel of an organic phosphorescent diode (OLED) can emit light independently. Therefore, OLED has developed into a new generation of full-color display technology, has broad application prospects, and has received extensive attention from domestic and foreign industries. [0003] Due to its heavy atom effect, ring metal phosphorescent materials can make full use of all singlet and triplet excitons gener...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54H01L51/46
CPCC07D471/04C09K11/06C09K2211/185H10K85/346
Inventor 佘远斌李贵杰许克伟
Owner ZHEJIANG UNIV OF TECH