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Polysubstituted phenylquinoline platinum (II) complex as well as preparation method and application thereof

A phenylquinoline platinum, multi-substitution technology, applied in the field of multi-substituted phenylquinoline platinum complexes, can solve the problem of reducing the quantum efficiency of luminescence

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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  • Polysubstituted phenylquinoline platinum (II) complex as well as preparation method and application thereof
  • Polysubstituted phenylquinoline platinum (II) complex as well as preparation method and application thereof
  • Polysubstituted phenylquinoline platinum (II) complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis of complex [2(4FPh)4Me]Pt(acac)

[0040]

[0041] (1) 4-Methylquinoline-2(1 H )-Ketone synthesis

[0042] Put 40mL concentrated sulfuric acid into a three-necked flask with a stirrer, gradually add 17.7g N-acetoacetanilide at room temperature, add 10mL concentrated sulfuric acid after the addition, heat up to 80℃ and react for 10min, carefully pour into 400mL ice water, and precipitate A large amount of white precipitate, filtered under reduced pressure, washed with water until neutral, dried under vacuum at 30°C to obtain 4-methylquinoline-2 (1 H )-Ketone white solid, colorless rod-shaped crystals are precipitated out by ethanol recrystallization, the yield is 87%. 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).

[0043] (2) Synthesis of 2-chloro-4-methylquinoline

...

Embodiment 2

[0051] Example 2: Synthesis of complex (2Ph4Me)Pt(acac)

[0052]

[0053] (1) Synthesis of 2-phenyl-4-methylquinoline

[0054] Take 3.0 g of 2-chloro-4-methylquinoline synthesized in Example 1, 2.06 g of phenylboronic acid, and Pd(PPh 3 ) 4 640mg, 20mL of saturated sodium carbonate aqueous solution, 10mL of anhydrous methanol, 40mL of toluene, were added to a three-necked flask with a stirrer, nitrogen gas, reflux reaction for 14h, discard the water layer, and extract the toluene layer with an aqueous sulfuric acid solution of appropriate concentration. After the extraction is complete, the acidic aqueous layer is combined and filtered to obtain a colorless and clear aqueous layer. The acidic aqueous phase is adjusted to weakly alkaline with potassium hydroxide solution of appropriate concentration, and a large amount of white solid is precipitated. The target product is obtained by static filtration or extraction with ethyl acetate. After vacuum drying at 35°C, 3.55 g of white cr...

Embodiment 3

[0067] Example 3: Synthesis of complex [2(224FPh)4Me]Pt(acac)

[0068]

[0069] (1) Synthesis of 2-(2,4-difluorophenyl)-4-methylquinoline

[0070] Take 3.0 g of 2-chloro-4-methylquinoline synthesized in Example 1, 2.67 g of 2,4-difluorophenylboronic acid, and Pd(PPh 3 ) 4 640mg, 20mL of saturated sodium carbonate aqueous solution, 10mL of anhydrous methanol, 40mL of toluene, were added to a three-necked flask with a stirrer, nitrogen gas, reflux reaction for 14h, after the reaction, the water layer was discarded, and the toluene was extracted with an aqueous sulfuric acid solution of appropriate concentration After multiple extractions, combine the acidic water layers and filter to obtain a colorless and clear water layer. Adjust the acidic water phase to weakly alkaline with a potassium hydroxide solution of appropriate concentration. A large amount of white solids precipitate out, static filtration or extraction with ethyl acetate The target product was obtained, which was vacuu...

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Abstract

The invention relates to a polysubstituted phenylquinoline platinum (II) complex which is expressed in the structural formula shown in the specification. The complex is prepared through the following steps of: utilizing a C<N> bidentate ligand-2-aryl-polysubstituted 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 from yellow lights to orange yellow lights and orange red lights.

Description

Technical field [0001] The invention relates to a multi-substituted phenylquinoline platinum (II) complex, a preparation method and application of the complex. technical background [0002] Since 1987, C. W. Tang first discovered aluminum octahydroxyquinoline (Alq 3 Since the electroluminescence of ), the photoluminescence and electroluminescence of organic compounds have received extensive attention. These organic light-emitting compounds are widely used in organic light-emitting diodes (OLEDs), organic sensing, and biological imaging. According to quantum theory, common organic light emission is divided into fluorescent light emission and phosphorescent light emission. However, for most of the pure organic molecules and light metal complexes, due to the long lifetime and spin forbidden of their triplet states, which exhibit non-radiative transitions, they can only use their singlet states to greatly reduce the Luminous quantum efficiency. The transition metal due to the heav...

Claims

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Application Information

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