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A kind of metal palladium (ii) complex containing bridged phenyl-phenyl-pyrazole structural unit and its application

A structural unit, the technology of metal palladium, which is applied in the field of four-ring metal palladium complex phosphorescence and delayed fluorescence or pure phosphorescence luminescent materials, can solve the problems that have not been reported yet, achieve the reduction of conjugation degree, enhance rigidity, and wide application foreground effect

Active Publication Date: 2022-01-21
ZHEJIANG UNIV OF TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although there have been some reports in the literature on phosphorescent materials of divalent cyclometallic palladium(II) metal complexes, there are no reports on tetradentate cyclometallic palladium(II) complexes containing bridged phenyl-phenyl-pyrazole structural units. See the report

Method used

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  • A kind of metal palladium (ii) complex containing bridged phenyl-phenyl-pyrazole structural unit and its application
  • A kind of metal palladium (ii) complex containing bridged phenyl-phenyl-pyrazole structural unit and its application
  • A kind of metal palladium (ii) complex containing bridged phenyl-phenyl-pyrazole structural unit and its application

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Experimental program
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Effect test

Embodiment 1

[0231] Embodiment 1: palladium complex Pd3 can be synthesized according to the following route:

[0232]

[0233] Synthesis of Intermediate 1: Add 2-bromopyrazole (7.38g, 30 mmol, 1.0 equiv), cuprous iodide (113.8mg, 0.3mmol, 0.01 eq), 1-methylimidazole (49.26 mg, 0.6 mmol, 0.02 eq), lithium tert-butoxide (4.84 g, 60 mmol, 2.0 eq). The nitrogen was replaced three times, and then 2-bromo-4-tert-butylpyridine (7.71g, 36mmol, 1.2eq), 1-methylimidazole (49.3mg, 0.6mmol, 0.02eq), 50mL toluene, oil The bath temperature was raised to 130°C for 24 hours. Cool to room temperature, distill under reduced pressure, remove solvent, then dry loading, adopt silica gel column chromatography column to carry out separation and purification, eluent is sherwood oil / ethyl acetate=20:1, obtains white solid 11.31g, collects The rate is 99%. 1 H NMR (500MHz, DMSO-d 6 ):δ1.39(s,9H),7.45 –7.56(m,3H),7.37(t,J=7.5Hz,1H),7.72(d,J=8.4Hz,2H),7.94(d,J= 1.5Hz, 1H), 8.23 ​​(d, J = 8.0Hz, 1H), 8.27–8....

Embodiment 2

[0247] Embodiment 2: palladium complex Pd14 can be synthesized according to the following route:

[0248]

[0249] Synthesis of Intermediate 10: Add Intermediate 4 (6.90g, 30mmol, 1.0eq), 2,5-dimethylphenylboronic acid (3.84g, 31.5mmol ,1.05eq),Pd(PPh 3 ) 4 (1.04 g, 0.9 mmol, 0.03 equiv), K 2 CO 3 (8.29g, 60mmol, 2.0 equivalents), the nitrogen was replaced three times, and 1,4-dioxane (30mL) and H 2 O (15 mL). The temperature of the oil bath was raised to 100°C and the reaction was stirred for 6.0 hours, cooled to room temperature, extracted three times with 30 mL of ethyl acetate, and washed with anhydrous Na 2 SO 4 Dry the organic phase, then filter, distill under reduced pressure, remove the solvent, apply the dry method, and use a silica gel column chromatography column to separate and purify, and the eluent is sherwood oil / ethyl acetate=20:1 to obtain 5.29g of a white solid , The yield is 69%. used directly in the next reaction.

[0250] Synthesis of intermedi...

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Abstract

The invention relates to the technical field of organic light-emitting materials, and provides a tetradentate ring metal palladium (II) complex light-emitting material containing a bridged phenyl-phenyl-pyrazole structural unit. The tetravalent metal palladium (II) has a structure represented by the general formula (I). The luminescent material provided by the present invention regulates the photophysical properties of the tetradentate ring metal palladium (II) complex by adjusting the structure of the ligand surrounding the metal center and the structure of the substituent on the ligand, and has high stability and high stability. The advantage of high efficiency; it has broad application prospects in many fields such as OLED display and lighting.

Description

【Technical field】 [0001] The invention relates to the technical field of organic luminescent materials, in particular to a tetradentate ring metal palladium (II) complex phosphorescence and delayed fluorescence or pure phosphorescence luminescent material containing a bridged phenyl-phenyl-pyrazole structural unit and its application . 【Background technique】 [0002] Compounds capable of absorbing and / or emitting light are useful in a variety of optical and electroluminescent devices, including: light-absorbing devices, solar- and photosensitive devices, organic light-emitting diodes (OLEDs), light-emitting devices, or both Devices that absorb in turn enable light emission and as markers for biological applications. Much research has been devoted to the discovery and optimization of organic and organometallic materials for use in optical and electroluminescent devices. In general, research in this area aims to achieve a number of goals, including improvements in absorption...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
Inventor 李贵杰佘远斌杨玉宁黄达陈少海
Owner ZHEJIANG UNIV OF TECH
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