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Blue light naphthalimide fluorescent compound

A naphthalimide and compound technology, which is applied in the field of naphthalimide compounds, can solve the problems of fluorescence quenching, device performance degradation, efficiency decline, etc., and achieve the effect of high solid-state fluorescence quantum efficiency

Inactive Publication Date: 2010-02-17
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the biggest defect of the doping process is that as the working time of the device increases, the Joule heat generated by it will promote the migration of molecules, so that the originally uniformly dispersed guest molecules will be separated from the host material due to aggregation, which will not only cause fluorescence quenching. The phenomenon of extinguishing, but also produces black spots that do not emit light, which degrades the performance of the device
This is because this molecule has a flat plate in its spatial structure, which leads to the accumulation between molecules, which makes its solid fluorescence emission wavelength red-shift relative to the solution fluorescence, from pure blue to blue-green. At the same time, the quantum efficiency of solid fluorescence is due to decrease due to concentration quenching

Method used

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  • Blue light naphthalimide fluorescent compound

Examples

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Effect test

Embodiment 1

[0042] The naphthalimide derivative in this example is N-(2-hydroxyethyl)-4-(4-tert-butylphenoxy)-1,8-naphthalimide (PONA1). The fluorescence of its solution is blue, and the fluorescence emission is at 429nm; the solid fluorescence is blue-green, and the fluorescence emission is at 471nm. By introducing a large sterically hindered tert-butyl group to the 4-position of 4-phenoxy, the purpose of increasing the molecular volume, reducing the intermolecular force, and improving the quantum yield of solid fluorescence is realized. The quantum efficiency of solid fluorescence is 41.56%. . The preparation process of the target compound described in this example includes: 1) Aminolysis reaction with 2-ethanolamine with 4-bromo-1,8-naphthalene dicarboxylic anhydride as the starting material; 2) Substitution reaction with phenol derivatives There are two steps.

[0043] 1) Amination reaction of 4-bromo-1,8-naphthalene dicarboxylic anhydride and 2-ethanolamine to generate N-(2-hydroxy...

Embodiment 2

[0050] The naphthalimide derivative in this example is N-(2-hydroxyethyl)-4-(2-tert-butylphenoxy)-1,8-naphthalimide (PONA2). The fluorescence of its solution is blue, and the fluorescence emission is at 432nm; the solid fluorescence is pure blue, and the fluorescence emission is at 448nm. By introducing a large sterically hindered tert-butyl group to the 2-position of 4-phenoxy group, the coplanarity of the benzene ring, oxygen atom and naphthalimide ring can be reduced, and the degree of conjugation can be reduced, so that the solid-state fluorescence emission spectrum The purpose of tuning from teal to pure blue. The preparation process of the target compound described in this example is the same as that in Example 1. Its reaction formula is as follows:

[0051]

[0052] The synthesis method is the same as in Example 1, except that the raw material is changed from 4-tert-butylphenol to 2-tert-butylphenol. The crude product was purified by column chromatography (eluent:...

Embodiment 3

[0054] The naphthalimide derivative in this example is N-(2-hydroxyethyl)-4-(2,4-di-tert-butylphenoxy)-1,8-naphthalimide (PONA3). The fluorescence of its solution is blue, and the fluorescence emission is at 432nm; the solid fluorescence is pure blue, and the fluorescence emission is at 448nm. By introducing two large sterically hindered tert-butyl groups to the 2- and 4-positions of 4-phenoxy, the following simultaneously can be achieved: 1) increasing molecular volume, reducing intermolecular forces, and improving solid fluorescence quantum yield; 2) The purpose of reducing the coplanarity of the benzene ring, the oxygen atom and the naphthalimide ring, and reducing the degree of conjugation, so that the solid fluorescence emission spectrum is tuned from blue-green to pure blue. Its solid fluorescence quantum efficiency is 28.59%. The preparation process of the target compound described in this example is the same as that in Example 1. Its reaction formula is as follows: ...

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Abstract

The invention relates to a blue light naphthalimide fluorescent compound with high solid fluorescence efficiency, which has the structure general formula shown at right, wherein R1 radical is 2-hydroxyethyl or 2-acetoxyl ethyl, R2 is hydrogen atom or tert-butyl group, and R3 is hydrogen atom or tert-butyl group. By introducing the tert-butyl group with large steric hindrance into the benzene ringof the 4-position phenoxyl substitutional group of 1, 8- naphthalimide, the invention increases the volume of target fluorescent molecules and reduces the mutual actions among the fluorescent molecules so as to reduce the concentration quenching action and enhance the solid fluorescence quantum efficiency. By introducing the tert-butyl group with large steric hindrance into the 2-position of the benzene ring of the 4-position phenoxyl substitutional group, the invention reduces the coplanarity of the benzene ring, oxygen atoms and a naphthalimide ring so as to ensure that the solid fluorescenttransmitted wavelength of the target fluorescent molecules shifts from aquamarine blue to ethereal blue.

Description

1. Technical field [0001] The invention relates to a class of naphthalimide compounds with blue fluorescent properties, in particular to a class of blue light naphthalimide compounds with high solid fluorescence quantum efficiency. 2. Background technology [0002] Organic electroluminescent materials are the core components of organic electroluminescent devices, because luminescent materials can determine the luminous color, brightness and efficiency of devices. In order to realize full-color display, it is necessary to develop red, green, and blue primary color light materials with good photothermal stability and high fluorescence quantum efficiency. So far, only green light-emitting materials have met the practical requirements. Relatively speaking, the performance of red and blue light-emitting fluorescent devices is poor. Especially for blue electroluminescent devices, the highest luminous efficiency reported in the literature is only 9.1lm / W, and the color purity is ...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06
Inventor 卢志云王毅陈静黄艳谢明贵
Owner SICHUAN UNIV
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