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Solid broadband green-light emission crystal material and preparation method thereof

A crystal material and broadband technology, applied in the field of solid-state broadband green light-emitting crystal materials and their preparation, can solve problems affecting device performance and achieve enhanced luminous performance, easy control, and less weathering effects

Active Publication Date: 2017-10-10
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

However, in practical applications, organic light-emitting materials often exist in the form of solid films or other aggregates. At the same time, organic light-emitting materials will inevitably crystallize under external conditions such as heat during use, thereby affecting device performance.

Method used

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  • Solid broadband green-light emission crystal material and preparation method thereof
  • Solid broadband green-light emission crystal material and preparation method thereof
  • Solid broadband green-light emission crystal material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of solid-state broadband green light emitting crystal material (Compound I)

[0029]

[0030] Dissolve 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein (30mmol) and 4-aminoantipyrine (30mmol) in 100ml In the water ethanol, 0.5 ml of glacial acetic acid was added dropwise with rapid stirring, and the reaction was refluxed for 3 hours under stirring; then, the ethanol was removed by rotary evaporation, and the obtained solid matter was filtered under reduced pressure and dried to obtain the target product; the crude product was reconstituted with methanol or ethanol After two crystallizations, ethanol was used as a solvent, and the crystals were naturally volatilized at room temperature. After 10 days, light brown massive crystals suitable for X-ray single crystal diffraction measurement were obtained, and the yield was 87%.

[0031] The obtained product was determined to be the target product by proton nuclear magnetic resonance spectrum, carbon n...

Embodiment 2

[0033] Example 2: Synthesis of solid-state broadband green light emitting crystal material (Compound I)

[0034] Obtained according to the method of Example 1, except that 3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)acrolein and 4-aminoantipyrine The molar ratio of is 1:1.1, and the organic solvent used in the reaction is chloroform.

Embodiment 3

[0035] Example 3: Crystal structure determination

[0036] In order to further determine the molecular structure of the crystal material, the crystal of the solid broadband green light emitting crystal material prepared in Example 1 was analyzed by X-ray single crystal structure. Select a single crystal of a suitable size under a microscope. The size of the single crystal used for single crystal structure determination is 0.400x 0.340x 0.270mm, which is light brown. The crystal structure determination was carried out on the Bruker Smart1000CCD X-ray single crystal diffractometer, using Cu K monochromated by graphite α Rays Diffraction data was collected at 150(2)K. The crystal structure was solved by the direct method, and the software used was SHELXS-2013 and SHELXL-2014. All non-hydrogen atoms are obtained by difference Fourier synthesis and difference electron density function correction, and all hydrogen atom coordinates are obtained from the difference electron density fun...

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PUM

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Abstract

The invention discloses a solid broadband green-light emission crystal material which is as shown in a formula I. Indole and pyrazolone serving as functional structure units are combined through an aza butadiene bridge bond phase to form a bis-heterocyclic organic light-emitting crystal material of aza butadiene bridging. The material has good green-light emission characteristics in crystalline state and solution. The material serving as an organic light-emitting material is used for the fields of light-emitting devices, laser dyes, fluorescence sensing, anti-counterfeiting techniques and biomedical analysis.

Description

Technical field: [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a solid-state broadband green light emitting crystal material and a preparation method thereof. Background technique: [0002] Organic light-emitting materials are widely used in organic electroluminescent devices (OLED), organic solid-state lasers, organic photovoltaic cells, biomedical fluorescent imaging, organic fluorescent sensors, and anti-counterfeiting materials. In most cases, organic light-emitting materials show strong fluorescence in dilute solutions, but only weak fluorescence in solid, aggregate or crystalline state, and even fluorescence quenching occurs. However, in practical applications, organic light-emitting materials often exist in solid thin films or other aggregate forms. At the same time, organic light-emitting materials are inevitably crystallized due to external conditions such as heat during use, which affects device performance. T...

Claims

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Application Information

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IPC IPC(8): C07D403/12C09K11/06
CPCC07B2200/13C07D403/12C09K11/06C09K2211/1029C09K2211/1044
Inventor 孙一峰吉国强胡建华秦健强刘梦影陈俊汪昭玮张译方安坤牟德海
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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