Aryl five-membered heterocyclic substituted quinoline platinum (II) complex, preparation method thereof and application

A five-membered heterocycle, quinoline platinum technology, applied in the field of aromatic five-membered heterocycle substituted quinoline platinum complexes, can solve the problem of reducing the luminous quantum efficiency and the like

Inactive Publication Date: 2013-08-21
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for most pure organic molecules and light metal complexes, due to the long lifetime and spin prohibition of the triplet state, they exhibit non-radiative transitions, so only the singlet state can be used, which greatly reduces the Luminous Quantum Efficiency

Method used

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  • Aryl five-membered heterocyclic substituted quinoline platinum (II) complex, preparation method thereof and application
  • Aryl five-membered heterocyclic substituted quinoline platinum (II) complex, preparation method thereof and application
  • Aryl five-membered heterocyclic substituted quinoline platinum (II) complex, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of complex [2(Thip-2-Ph)4Me]Pt(acac)

[0039]

[0040] (1) 4-Methylquinoline-2(1 H )-ketone synthesis

[0041] Add 40mL of concentrated sulfuric acid into a three-necked flask with a stirring bar, and gradually add N -Acetoacetanilide 17.7g, add 10mL of concentrated sulfuric acid after adding, heat up to 80°C for 10min, then carefully pour into 400mL of ice water after completion, a large amount of white precipitate precipitates, vacuum filter, wash with water until neutral, at 30°C Vacuum drying gave a white solid with a yield of 87%. Colorless rod-shaped crystals were precipitated by ethanol recrystallization. 1 H NMR (600MHz, CDCl 3 ) δ(ppm): 11.95(br; 1H); 7.70(dd; J =1.20Hz; J =7.20Hz; 1H); 7.52(dt; J =1.20Hz; J =7.20Hz; 1H); 7.42(dd; J =1.20Hz; J =7.20Hz; 1H); 7.26(dt; J =1.20Hz; J =7.20Hz; 1H); 6.61(q; J =1.20Hz; 1H); 2.53(d; J =1.20Hz; 3H).

[0042] (2) Synthesis of 2-chloro-4-methylquinoline

[0043] Take 4-methylqu...

Embodiment 2

[0053] Embodiment 2: the synthesis of complex [2(Thip-2-Ph)3F4Me]Pt(acac)

[0054]

[0055] (1) 3-bromo-4-methylquinoline-2(1 H )-ketone synthesis

[0056] Get the synthetic 4-methylquinoline-2(1 of embodiment 1 H )-ketone 7.0g, bromine 7.04g, anhydrous acetic acid 100mL, anhydrous DMF 45mL. First dissolve 4-methylquinoline-2 (1 H )-ketone solution in anhydrous acetic acid was added to a three-necked flask with a stirrer, protected from light, then heated to 65°C and stirred, then quickly added in anhydrous acetic acid solution of bromine, and after the addition was completed, 45 mL of anhydrous DMF, the reaction solution turns into a brown transparent solution, stirred and reacted at 65°C for 5 hours, the reaction solution turned into light yellow and transparent, stopped heating, and after slow cooling, a large amount of white crystals precipitated, the reaction product was poured into 600mL of water, and a large amount of white flocs were precipitated A white filter ...

Embodiment 3

[0067] Example 3: Synthesis of complex [2(Thip-2-Ph)3,7DiF4Me]Pt(acac)

[0068]

[0069] (1) 3,7-dibromo-4-methylquinoline-2(1 H )-ketone synthesis

[0070] Get the synthetic 4-methylquinoline-2(1 of embodiment 1 H )-ketone 7.0g, bromine 14.07g, anhydrous acetic acid 100mL, anhydrous DMF 45mL. First dissolve 4-methylquinoline-2 (1 H Add the anhydrous acetic acid solution of )-ketone into a three-necked flask with a stirrer, heat to 65°C in the dark and stir, then quickly add the bromine anhydrous acetic acid solution dropwise, and then add 45mL of anhydrous DMF to the reaction solution Turn into a brown transparent liquid, stir and react at 65°C for 10h, the reaction liquid becomes light yellow and transparent, stop heating, cool slowly, a large amount of white crystals are precipitated, the reaction product is poured into 600mL water, a large amount of white flocculent solids are precipitated, pumped A white filter cake was obtained by filtration, washed with water thr...

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Abstract

The invention relates to an aryl five-membered heterocyclic substituted quinoline platinum (II) complex which is as shown in the following structural formula. The complex is prepared according to the following steps: utilizing a C<N> bidentate ligand- aryl five-membered heterocyclic substituted quinoline to react with potassium chloroplatinite so as to obtain a platinum (II) chlorendic dimmer of the corresponding ligand, and utilizing the platinum (II) chlorendic dimmer to react with acetylacetone so as to prepare the complex. The target platinum (II) complex prepared by the method can serve as electroluminescent phosphorescent materials and doped phosphorescent materials to be applied to organic electroluminescent devices, and the substituent groups of different electron-withdrawing groups and electron-donating groups are introduced so as to regulate the phosphorescent light color of the target complex, so that the complex can emit red lights.

Description

technical field [0001] The invention relates to an aromatic five-membered heterocyclic substituted quinoline platinum (II) complex, a preparation method and application of the complex. technical background [0002] Since C. W. Tang first discovered octahydroxyquinoline aluminum (Alq 3 ), the photoluminescence and electroluminescence of organic compounds have received widespread attention. These organic light-emitting compounds are widely used in the fields of organic light-emitting diodes (OLEDs), organic sensing, and bioimaging. According to quantum theory, common organic luminescence is divided into fluorescence luminescence and phosphorescence luminescence. However, for most pure organic molecules and light metal complexes, due to the long lifetime and spin prohibition of the triplet state, they exhibit non-radiative transitions, so only the singlet state can be used, which greatly reduces the Luminous Quantum Efficiency. However, due to the heavy atom effect of heavy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 王华陶鹏赵强景姝汪静霞陈柳青黄维许并社
Owner TAIYUAN UNIV OF TECH
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