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Fluorophenyl pyrimidine solid green emission organic light-emitting material and preparation method thereof

A technology of substituted phenylpyrimidines and luminescent materials, which is applied in the field of fluorophenylpyrimidine-based solid-state green light-emitting organic luminescent materials and their preparation, to achieve the effects of improving processing performance and practicability, reducing coplanarity, and enhancing luminescent performance

Active Publication Date: 2017-09-08
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although isopropylmethylsulfonamidofluorophenylpyrimidine derivatives have been paid attention to by researchers and a lot of research has been carried out, the research on this type of compounds in the prior art is mostly limited to synthetic methods, process research, and as The application of pharmaceutical intermediates in the synthesis of rivastatin, but the preparation and research of luminescent materials are rarely reported
[0006] Using 3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl)acrolein as raw material, through polyenone The bridge connects two isopropylmethylsulfonylaminofluorophenylpyrimidine functional groups to form a bisfluorophenylpyrimidine compound, which has solid-state green light emission characteristics. The work involved in the present invention is based on existing Not yet reported in the technology

Method used

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  • Fluorophenyl pyrimidine solid green emission organic light-emitting material and preparation method thereof
  • Fluorophenyl pyrimidine solid green emission organic light-emitting material and preparation method thereof
  • Fluorophenyl pyrimidine solid green emission organic light-emitting material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 4-propyl-2,6-bis(3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino)pyrimidine -5-yl)allyl)-cyclohexanone (compound Ia) preparation

[0034]

[0035] In a 250 ml round bottom flask, mix 4-propylcyclohexanone (1mmol) and 3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methyl) Sulfonylamino)pyrimidin-5-yl)acrolein (2mmol) was dissolved in 100ml of ethanol, and 20ml of potassium hydroxide solution with a mass fraction of 15-20% was added dropwise to the solution under rapid stirring and kept at room temperature. The reaction is stirred for 10-15 hours. After that, the reaction solution was poured into 150 ml of water and left to stand. The obtained solid matter was suction filtered under reduced pressure, washed with water several times, and dried at room temperature. It was recrystallized with ethanol-acetone mixed solvent and dried in vacuum to obtain yellow-green needle-like crystals with a yield of 78%.

[0036] 1 H NMR(300MHz, CDCl 3 / TMS)δ:...

Embodiment 2

[0037] Example 2: 1-propyl-3,5-bis(3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino)pyrimidine -5-yl)allyl)-4-piperidone (compound Ib):

[0038]

[0039] In a 250 ml round bottom flask, mix 4-propylcyclohexanone (1mmol) and 3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methyl) Sulfonylamino)pyrimidin-5-yl)acrolein (2mmol) was dissolved in 100ml of methanol. Under rapid stirring, 20ml of sodium hydroxide solution with a mass fraction of 15-20% was added dropwise to the solution and kept at room temperature. The reaction is stirred for 10-15 hours. After that, the reaction solution was poured into 150 ml of water and left to stand. The obtained solid matter was suction filtered under reduced pressure, washed with water several times, and dried at room temperature. It was recrystallized with ethanol-acetone mixed solvent and dried in vacuum to obtain yellow flake crystals with a yield of 72%.

[0040] 1 H NMR(300MHz, CDCl 3 / TMS)δ:0.91(t,J=7.5Hz,3H),1.26-1.39(...

Embodiment 3

[0041] Example 3: 4-Propyl-2,6-bis(3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidine -5-yl)allyl)-cyclohexanone (compound Ia) preparation

[0042] According to the method of Example 1, the difference is that 4-propylcyclohexanone and 3-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methyl) The molar ratio of sulfonylamino)pyrimidin-5-yl)acrolein is 1:2.3, and the recrystallization solvent used is ethanol.

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Abstract

The invention discloses a fluorophenyl pyrimidine solid green emission organic light-emitting material and a preparation method thereof. The novel fluorophenyl pyrimidine solid green emission organic light-emitting material is formed by binding two types of functional structural units of propyl substituted cycloketone and isopropyl methylsulfonyl amino-fluorophenyl pyrimidine through poly-ketene bridge bonds. The fluorophenyl pyrimidine solid green emission organic light-emitting material can embody solid broadband green emission characteristics when in a solid state. The preparation method of the fluorophenyl pyrimidine solid green emission organic light-emitting material is simple in operation and convenient to synthesize; the obtained fluorophenyl pyrimidine solid green emission organic light-emitting material is high in stability and practicality and can be applied to fields such as luminescent devices, laser dyes, anti-counterfeit technology, fluorescence sensing and biomedical analysis. The fluorophenyl pyrimidine solid green emission organic light-emitting material expands the study and application field of fluorophenyl pyrimidine compounds. As shown in the chemical formula, X is C or N.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of organic light-emitting materials, and specifically relates to a fluorophenylpyrimidine solid-state green light-emitting organic light-emitting material and a preparation method thereof. [0003] Background technique: [0004] Organic light-emitting materials are widely used in organic electroluminescent devices, organic solid-state lasers, organic photovoltaic cells, biomedical fluorescent imaging, organic fluorescent sensors, and anti-counterfeiting materials. The design and development of organic luminescent materials with strong solid-state fluorescence emission, high fluorescence efficiency, and various emission wavelengths is a hot spot in the field of optoelectronic materials and technology, and has very important theoretical significance and practical value. [0005] Isopropylmethanesulfonylamino fluorophenylpyrimidine is an important pharmacodynamic group and an effective functional structural unit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42C09K11/06
CPCC07D239/42C09K11/06C09K2211/1044
Inventor 孙一峰胡建华秦健强汪昭玮张译方陈俊安坤刘梦影叶小机牟德海
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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