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Metal palladium (II) compound with bridged phenyl-phenyl-carbazole structure unit and application of compound

A structural unit and metal palladium technology, which is applied in the field of tetradentate ring metal palladium complex phosphorescence and delayed fluorescence or pure phosphorescence luminescent materials, and can solve the problems that have not yet been reported.

Active Publication Date: 2019-05-14
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Metal palladium (II) compound with bridged phenyl-phenyl-carbazole structure unit and application of compound
  • Metal palladium (II) compound with bridged phenyl-phenyl-carbazole structure unit and application of compound
  • Metal palladium (II) compound with bridged phenyl-phenyl-carbazole structure unit and application of compound

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Experimental program
Comparison scheme
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-bromocarbazole (7.38g, 30mmol, 1.0eq), cuprous iodide (113.8mg, 0.3mmol, 0.01eq ), 1-methylimidazole (49.26mg, 0.6mmol, 0.02eq), lithium tert-butoxide (4.84g, 60mmol, 2.0eq). 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 the solvent, then apply the sample by dry method, use silica gel column chromatography to separate and purify, and the eluent is petroleum ether / ethyl acetate=20:1, and obtain 11.31 g of white solid. 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), 8.2...

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 (1.04g, 0.9mmol, 0.03eq), 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 dry method, and use silica gel column chromatography to separate and purify. The eluent is petroleum ether / ethyl acetate=20:1 to obtain 5.29g of white solid , The yield is 69%. used directly in the next reaction.

[0250] Synthesis of intermediate 11: Add intermedia...

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Abstract

The invention provides a metal palladium (II) compound with a bridged phenyl-phenyl-carbazole structure unit and an application of the compound. Metal palladium (II) has a structure as shown in a general formula (I). According to a luminescent material, structures of ligands around a metal center are adjusted, structures of substituent groups on the ligands are adjusted and controlled, so that optical physical properties a four-toothed ring metal palladium (II) compound are adjusted and controlled, and the compound has the advantages of high stability and efficiency. The compound has wide application prospects in the fields of displaying, lighting and the like of an OLED (organic light emitting diode).

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-carbazole 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 absorptio...

Claims

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Application Information

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Patent Type & Authority Applications(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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