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A kind of benzoxazole solid fluorescent material

A technology of benzoxazoles and fluorescent materials, applied in the field of fluorescent materials, can solve the problems of low efficiency, lack of blue-light material building groups, low color purity, etc.

Active Publication Date: 2022-08-05
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the marketed red and green OLED materials, blue light materials have not been widely used due to many problems such as lack of building groups, complex structure, low color purity, and low efficiency.

Method used

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  • A kind of benzoxazole solid fluorescent material
  • A kind of benzoxazole solid fluorescent material
  • A kind of benzoxazole solid fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of compound BZ-1

[0038] Structural formula:

[0039]

[0040] Chinese name: 2-phenoxybenzo[d]oxazole

[0041] English name: 2-phenoxybenzo[d]oxazole

[0042] Synthesis method: dissolve phenol (0.6110g, 6.48mmol) in 20ml of acetonitrile, add anhydrous potassium carbonate (0.8960g, 6.48mmol), and reflux for 1h. 2-Chlorobenzoxazole (0.9060 g, 5.9 mmol) was added to the above solution, and the heating was continued for 4 h under reflux. After the reaction was completed, suction filtration was performed to obtain the filtrate, and the organic solvent was spun off to obtain a crude product. Add n-hexane for recrystallization to obtain 0.87 g of a white solid product with a yield of 70%. 1 H NMR (500MHz, CDCl 3 )δ7.52(d, J=7.4Hz, 1H), 7.50–7.45 (m, 2H), 7.45–7.40 (m, 3H), 7.31 (d, J=7.3Hz, 1H), 7.29–7.21 (m , 2H). 13 C NMR (126MHz, CDCl 3 )δ161.20,151.73,147.39,139.72,128.93,125.40,123.48,122.39,119.12,117.72,108.85.

Embodiment 2

[0043] Example 2: Synthesis of Compound BZ-2

[0044]

[0045] Chinese name: 2-(4-methoxyphenoxy)benzo[d]oxazole

[0046] English name: 2-(4-methoxyphenoxy)benzo[d]oxazole

[0047] Synthesis method: Dissolve 4-methoxyphenol (0.4450g, 3.58mmol) in 20ml of acetonitrile, add anhydrous potassium carbonate (0.4950g, 3.58mmol), and reflux for 1h. 2-Chlorobenzoxazole (0.5 g, 3.26 mmol) was added to the above solution, and the heating was continued for 4 h under reflux. After the reaction was completed, dichloromethane was added for suction filtration to obtain a filtrate, and the organic solvent was spun off to obtain a crude product. Add n-hexane for recrystallization to obtain 0.5260 g of a white solid product with a yield of 67%. 1 H NMR (500MHz, CDCl 3 )δ7.50(d,J=7.4Hz,1H),7.41(d,J=9.1Hz,1H),7.32(d,J=9.0Hz,2H),7.28–7.20(m,2H),6.97( d, J=9.0Hz, 2H). 13 C NMR (126MHz, CDCl 3 )δ162.82,157.65,148.44,146.28,140.77,124.41,123.24,121.22,118.64,114.85,109.80,55.63.

Embodiment 3

[0048] Example 3: Synthesis of compound BZ-3

[0049]

[0050]Chinese name: 2-(4-Chlorophenoxy)benzo[d]oxazole

[0051] English name: 2-(4-chlorophenoxy)benzo[d]oxazole

[0052] Synthesis method: Dissolve 4-chlorophenol (0.4610g, 3.59mmol) in 20ml of acetonitrile, add anhydrous potassium carbonate (0.4950g, 3.58mmol), and reflux for 1h. 2-Chlorobenzoxazole (0.5 g, 3.26 mmol) was added to the above solution, and the heating was continued for 4 h under reflux. After the reaction was completed, dichloromethane was added for suction filtration to obtain a filtrate, and the organic solvent was spun off to obtain a crude product. Add n-hexane for recrystallization to obtain 0.52 g of a white solid product with a yield of 65%. 1 H NMR (500MHz, CDCl 3 )δ7.52(d,J=8.9Hz,1H),7.45-7.41(m,3H),7.39(d,J=9.0Hz,2H),7.30-7.23(m,2H). 13 C NMR (126MHz, CDCl 3 )δ160.85,150.10,147.38,139.49,130.82,128.97,123.62,122.61,120.55,117.76,108.93.

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Abstract

The invention discloses a benzoxazole solid fluorescent material and a preparation method thereof, belonging to the field of functional materials. The benzoxazole compounds described in the present invention have a simple molecular skeleton structure, and the synthesis method is simple and convenient. Such fluorescent materials have almost no fluorescence in dilute solutions, but have strong fluorescence in concentrated solutions, exhibiting aggregation-induced luminescence properties. In the solid state, the maximum emission wavelength of such molecules can cover the range of ultraviolet light to blue light, with good fluorescence quantum yield, and has potential applications in the field of optoelectronics.

Description

【Technical field】 [0001] The invention relates to the technical field of fluorescent materials, in particular to a benzoxazole-based solid fluorescent material. 【Background technique】 [0002] Organic light-emitting devices (OLEDs) have the advantages of bright colors, high contrast, and flexible display. As a new generation of flat panel display technology, they have attracted extensive attention of researchers and have broad application prospects. The fluorescence of traditional organic fluorescent materials will be quenched in the aggregated state or solid state, which seriously restricts the practical application of organic fluorescent materials. Since 2001, Tang Benzhong's research group has developed a series of fluorescent molecules with aggregation-induced emission characteristics, and proposed the mechanism of intramolecular rotation limitation and intramolecular vibration limitation, which has promoted the application of organic fluorescent materials in optoelectro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/58C09K11/06
CPCC07D263/58C09K11/06C09K2211/1033
Inventor 陈绍晋胡志强孟媛媛夹强杜春晖王鲲鹏
Owner QINGDAO UNIV OF SCI & TECH
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