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Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material

A technology of triarylphenanthrene and blue light materials, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of device performance influence, film loosening, etc., to enhance compatibility, enhance luminous intensity, reduce The effect of the quenching effect

Inactive Publication Date: 2014-07-30
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the parent anthracene itself has relatively serious defects. It is a planar molecule and is easy to crystallize. The formed film is loose, which has a great impact on the performance of the device.

Method used

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  • Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material
  • Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material
  • Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, the structure and synthesis of 1-(2-naphthyl)-2,3-bis(2-benzoxazolyl)anthracene

[0025]

[0026] Weigh 400mg (1.48mmol) of 1-(2-naphthyl)-2-(2-benzoxazolyl)acetylene in an internal immersion photoreactor, add 80ml of acetonitrile, and ultrasonically dissolve it completely, the solution is colored liquid and then sealed. Under a nitrogen protection environment, a 300W medium-pressure mercury lamp was used to illuminate, and the reaction was monitored by TLC at any time. After 2 hours, it was found that only a new point was generated, and the light was continued, and the color of the solution gradually became darker. After 6 hours, the basic reaction of the raw materials was completed, and the reaction was stopped. The solvent was spin-dried to obtain a tan solid, which was separated by 100-200 mesh silica gel column chromatography, and the precipitant was dichloromethane: ethyl acetate = 1: 1 to obtain 260 mg of white powder with a yield of 65%, m.p.: ...

Embodiment 2

[0027] Example 2. The structure and synthesis of 1-(1-naphthyl)-2,3-bis(2-benzoxazolyl)phenanthrene

[0028]

[0029] 1.00 g of 1-(1-naphthyl)-2-(2-benzoxazolyl)acetylene was dissolved in 150 ml of acetonitrile to obtain a clear light yellow solution. After adopting a 300W medium-pressure mercury lamp to irradiate for 6 hours, it was found by spotting that the reaction was substantially complete, and the acetonitrile solvent was spin-dried, and column chromatography was carried out with PE: EA: DCM=90: 1: 1 to obtain 0.721g of pure product, and the yield was 72%, m.p.: 224-228°C, 1 H NMR (400MHz, CDCl 3 , 25°C, TMS): δ9.93(s, 1H, J=8.4Hz), 9.10-9.08(d, 1H, J=8.4Hz), 7.2-7.90(m, 1H), 7.55-7.40(m, 6H), 7.34-7.30 (m, 1H), 7.26-7.12 (m, 6H) ppm; 13 C NMR (400MHz, CDCl 3 , 25°C, TMS): 6161.1, 160.5, 149.9, 149.7, 141.2, 140.9, 140.3, 133.7, 132.3, 132.2, 132.1, 131.7, 130.6, 129.1, 128.0, 127.7, 127.7, 1267.3, 1257.2, 12 , 124.5, 124.2, 124.1, 124.0, 124.0, 123.8, 123.7, 12...

Embodiment 3

[0030] Example three, the structure and synthesis of 1-(2-naphthyl)-2,3-bis(5-tert-butyl-2-benzoxazolyl)anthracene

[0031]

[0032]Using 1-(2-naphthyl)-2-(5-tert-butyl-2-benzoxazolyl)acetylene as raw material, it was prepared under the same reaction conditions as in Example 1. Yield 70%, m.p.: 232-234°C; 1 H NMR (400MHz, CDCl 3 , 25°C, TMS): δ (ppm) 9.01 (s, 1H), 7.98 (d, 1H, J=8.8Hz), 7.93-7.86 (m, 3H), 7.81-7.77 (m, 2H), 7.68 ( d, 1H, J=7.6Hz), 7.55-7.53(m, 3H), 7.46-7.38(m, 4H), 7.28(s, 2H), 7.24(m, 4H), 1.31(d, 18H, J= 2Hz); 13 CNMR (400MHz, CDCl 3 ,25℃,TMS):δ(ppm)161.59,161.40,148.77,148.64,147.99,147.09,142.89,141.59,141.34,138.16,134.52,134.43,133.39,132.53,130.67,130.42,130.34,130.21,128.83,128.74 , 128.46, 128.27, 127.94, 127.70, 127.27, 127.11, 127.05, 126.13, 126.04, 125.07, 123.06, 122.37, 116.67, 116.43, 109.38, 109.35, 364.84, 3114.82, 3MS (IES + )[M+H] + calculated for C 46 h 39 N 2 o 2 : 651.3012, found: 651.3016.

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Abstract

The invention discloses a novel blue ray material with a 1,2,3-triaryl anthracene or 1,2,3-triaryl phenanthrene structure and a preparation method of the blue ray material. Derivatives of 1-(1-naphthyl)-2-(2-benzoxazolyl) acetylene and 1-(2-naphthyl)-2-(2-benzoxazolyl) acetylene are adopted as raw materials, a light ring addition reaction between hetero-aryl acetylenes is carried out in acetonitrile under irradiation of ultraviolet light. Maximum ultraviolet absorption wavelength of the novel triaryl anthracene or phenanthrene derivative is 280-300nm, shoulder peak of the novel triaryl anthracene or phenanthrene derivative extends to 380nm, and the novel triaryl anthracene or phenanthrene derivative can emit blue fluorescent lights with maximum emission wavelength of 380-400nm and shoulder peak extending to 500nm.

Description

Technical field: [0001] The invention relates to the field of organic photoelectric functional materials, in particular to organic blue light materials with anthracene or phenanthrene structure. Background technique: [0002] Organic electroluminescent technology is a new type of display technology developed in recent years, gradually replacing traditional electronic display and liquid crystal display technology. Organic electroluminescent technology has the advantages of high brightness, simple functional molecular structure, low energy consumption, large viewing angle, adjustable luminous wavelength, and active luminescence. Research hotspots. [0003] Among color organic electroluminescent display materials, the development of blue light materials is an important key technology. Compared with green light and red light, blue light has the shortest wavelength and the highest energy. Through energy transfer, green light and red light can be obtained, and then combined with...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D263/57
Inventor 庄俊鹏刘杰郝海军牛俊宇
Owner BEIJING UNIV OF CHEM TECH
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