A polyketene compound, its application as a dual-fluorescent emission organic light-emitting material and its preparation method

A technology for luminescent materials and compounds, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of difficult industrialized production, difficult product separation, complex synthesis routes, etc., to promote solid-state luminescence performance, reduce mutual effect, the effect of enhancing the luminous performance

Active Publication Date: 2020-07-07
INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Organic conjugated polyene compounds have attracted widespread attention due to their unique electronic structures and optoelectronic properties. However, in the prior art, the synthesis routes of such compounds are complicated, the conditions are strict, the separation of products is difficult, and the cost is high. Poor practicability makes it difficult to popularize and produce industrially, which limits its effective application

Method used

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  • A polyketene compound, its application as a dual-fluorescent emission organic light-emitting material and its preparation method
  • A polyketene compound, its application as a dual-fluorescent emission organic light-emitting material and its preparation method
  • A polyketene compound, its application as a dual-fluorescent emission organic light-emitting material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: 1,10-bis(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-1,3,7,9-decatetraene-5, Preparation of 6-diketone (I):

[0028] In a dry 250mL round bottom flask, add 2,3-butanedione (0.01mol), 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl ) acrolein (0.02mol), and anhydrous methanol (150mL), then add piperidine (0.5mL) to the solution under rapid stirring, stir and reflux for 9 hours, cool to room temperature after the reaction, and separate out a brown solid substance , filtered under reduced pressure, washed twice with absolute ethanol to obtain the crude product, the crude product was recrystallized with ethanol-acetone mixed solvent (volume ratio of ethanol and acetone is 3:1), dried in vacuum to obtain brown solid 1,10- bis(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-1,3,7,9-decatetraene-5,6-dione. The yield was 18%.

[0029] The obtained product was determined to be the target product by proton nuclear magnetic resonance spectrum and carbon nuclear magne...

Embodiment 2

[0031] Example 2: 1,10-bis(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-1,3,7,9-decatetraene-5, Preparation of 6-diketone (I):

[0032] In a dry 250mL round bottom flask, add 2,3-butanedione (0.01mol), 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl ) acrolein (0.022mol), and absolute ethanol (150mL), then add piperidine (0.5mL) to the solution under rapid stirring, stir and reflux for 5 hours, cool to room temperature after the reaction, and separate out a brown solid substance , filtered under reduced pressure, washed twice with anhydrous methanol to obtain the crude product, the crude product was recrystallized with ethanol-acetone mixed solvent (the volume ratio of ethanol and acetone was 3:1), and dried in vacuo to obtain a brown solid 1,10- bis(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-1,3,7,9-decatetraene-5,6-dione. The yield was 19%.

Embodiment 3

[0033] Embodiment 3: Solid-state luminescent performance test

[0034] The solid-state photoluminescence spectrum is measured with a Horiba Jobin-Yvon LabRam HR800 laser Raman spectrometer, the excitation light source is a 325nm He–Cd laser, and the polyketene compound prepared in Example 1 is used for solid-state luminescence performance testing. The test results are shown in figure 1 .

[0035] Depend on figure 1It can be seen that the polyketene compound obtained in Example 1 exhibits dual fluorescence emission characteristics under 325nm laser excitation, and its emission spectrum covers almost the entire visible region, and is accompanied by a shoulder structure in the short-wave region. The emission wavelengths of its dual emission peaks are 597nm and 638nm respectively, and the maximum emission wavelength is 638nm. Therefore, the molecule emits strong red fluorescence.

[0036] The above results show that the polyketene compound, as a dual-fluorescence emission organi...

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Abstract

The present invention discloses a polyketene compound shown as a formula I. Two fluorophenylindole functional groups are connected through a polyene dione bridge bond to form the polyketene organic light-emitting material having a bi-fluorescence emitting characteristic, and the material is endowed with a solid red light emitting characteristic, compatibility and processability. The polyketene compound as the bi-fluorescence emitting organic light-emitting material shows a good red light emitting characteristic in a solid state. The polyketene bi-fluorescence emitting organic light-emitting material can be adopted directly as a red light emitting material and used in fields such as light-emitting devices, laser dye, anti-counterfeiting technology, light-converting materials, fluorescence sensitivity and biomedical analysis.

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a polyketene compound, its application as a dual fluorescent emission organic luminescent material and its preparation method. Background technique: [0002] Organic light-emitting materials are widely used in organic light-emitting devices, organic solid-state lasers, organic photovoltaic cells, organic fluorescent sensors, bioluminescent imaging, and light-transforming materials. The most prominent feature is that it can convert various forms of absorbed energy into light radiation. One of the key issues to be solved in the development of organic light-emitting materials is how to improve the solid-state emission properties of organic materials, because in most cases, although organic light-emitting materials show strong fluorescence in dilute solutions, they often fluoresce in solid or aggregated states. Quenching, there is only weak fluorescence or alm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C09K11/06
CPCC07D209/12C09K11/06C09K2211/1007C09K2211/1029
Inventor 孙一峰管啸晓魏俊锋汪昭玮张译方刘梦影谢宇达钱友荣李天龙潘文龙
Owner INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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