Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof

A technology of decyl imidazole and luminescent materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the complex synthesis of imidazole compounds, poor material solubility, compatibility and processability, fluorescence quenching, etc. problems, achieving good optical properties, improving processability, and preventing concentration quenching

Active Publication Date: 2016-08-10
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

[0005] Although imidazole compounds have been developed and applied to a greater extent, there are still problems such as the complex structure or large conjugated imidazole compound synthesis is relatively complex, there is fluorescence quenching phenomenon, material solubility, compatibility and processability Poor and other disadvantages

Method used

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  • Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof
  • Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof
  • Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: Synthesis of decyl imidazole blue light emitting organic luminescent material (compound I)

[0030] a. Synthesis of Intermediate (Compound II)

[0031] In a dry 250 ml flask, add 4-(1-n-decylphenanthrene[9,10-d]imidazol-2-yl)benzohydrazide (compound III) (0.01mol) and 2-diphenyl Phosphinebenzaldehyde (compound IV) (0.01mol) and 100 milliliters of absolute ethanol were stirred and refluxed for 5 hours, and the ethanol was evaporated under reduced pressure to precipitate a white solid. The crude product was recrystallized with ethanol to obtain an intermediate (compound II). The yield was 77%. The melting point is 200-202°C. ESI-MS m / z: 765.4 (M+H)+.

[0032] b. Synthesis of decyl imidazole blue light-emitting organic light-emitting materials (compound I)

[0033] The above-mentioned intermediate (compound II) was dissolved in 100 milliliters of dichloromethane, and under rapid stirring, 10 milliliters of 30% hydrogen peroxide was added dropwise at room te...

Embodiment 2

[0036] Synthesis of Decylimidazole Blue Light Emitting Organic Light-Emitting Material (Compound I)

[0037] a. Synthesis of Intermediate (Compound II)

[0038] In a dry 250 ml flask, add 4-(1-n-decylphenanthrene[9,10-d]imidazol-2-yl)benzohydrazide (compound III) (0.01mol) and 2-diphenyl Phosphinebenzaldehyde (compound IV) (0.011mol) and 100 milliliters of anhydrous methanol were stirred and refluxed for 7 hours, and methanol was evaporated under reduced pressure to precipitate a white solid. The crude product was recrystallized with ethanol to obtain an intermediate (compound II). The yield was 79%. ESI-MS m / z: 763.3 (M-H)-.

[0039] b. Synthesis of decyl imidazole blue light-emitting organic light-emitting materials (compound I)

[0040] The above intermediate (compound II) was dissolved in 100 ml of dichloromethane, and under rapid stirring, 20 ml of 30% hydrogen peroxide was added dropwise at room temperature, and the stirring reaction was continued for 5 hours at room ...

Embodiment 3

[0042] Synthesis of Decylimidazole Blue Light Emitting Organic Light-Emitting Material (Compound I)

[0043] a. Synthesis of Intermediate (Compound II)

[0044] In a dry 250 ml flask, add 4-(1-n-decylphenanthrene[9,10-d]imidazol-2-yl)benzohydrazide (compound III) (0.01mol) and 2-diphenyl Phosphinebenzaldehyde (compound IV) (0.011mol) and 100 milliliters of chloroform, stirred and refluxed for 6 hours, evaporated chloroform under reduced pressure, and precipitated a white solid, and the crude product was recrystallized with ethanol to obtain an intermediate (compound II). 75%. ESI-MS m / z: 765.4 (M+H)+.

[0045] b. Synthesis of decyl imidazole blue light-emitting organic light-emitting materials (compound I)

[0046] The above intermediate (compound II) was dissolved in 100 ml of dichloromethane, and under rapid stirring, 15 ml of 30% hydrogen peroxide was added dropwise at room temperature, and the stirring reaction was continued for 4 hours at room temperature, and then 50 ...

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Abstract

The invention discloses a decyl imidazole blue-light emission organic light-emitting material and a preparation method thereof .N-decyl is introduced into an imidazole structure unit, a phenanthroimidazole compound obtained through triphenylphosphine oxide functionalization is formed, the solid light-emitting characteristics, flame retardance, compatibility and machinability of the material are achieved while the solubility of the material is improved, and meanwhile the blue-light emitting characteristics of the material are kept .The preparation method is easy to implement and environmentally friendly, synthesis is convenient, the adopted solvents can be recycled and reduced, the obtained product is easy to purify and can be used as the blue-light conversion material for agricultural film production, the light quality of agricultural films is improved, the material can also be used as the blue-light emitting material for the fields of light-emitting devices, anti-fake materials, fluorescent sensing and the like, and the material can be used through solvent dissolution processing and can also be used as a solid material to be directly used, so that use is quite convenient .

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a decyl imidazole blue-light emitting organic luminescent material and a preparation method thereof. Background technique: [0002] Organic light-emitting materials are widely used in organic electroluminescent devices, organic solid-state lasers, organic photovoltaic cells, organic fluorescent sensors, light conversion agents and other fields. With the rapid development of modern science and technology, the application fields of organic light-emitting materials continue to expand, and there is an urgent need to develop solid-state organic light-emitting materials with high efficiency, low price, different emission wavelengths, multi-functions, and excellent performance to meet the needs of many current technical fields. [0003] In general, although organic light-emitting materials show strong fluorescence in dilute solutions, fluorescence quenching often ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506C09K11/06
CPCC07F9/65068C09K11/06C09K2211/1044
Inventor 叶小机张东娣孙一峰汪昭玮吉国强李兴宋化灿牟德海
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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