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Silicon-containing benzanthracene-based organic light-emitting material and its preparation method and application

A technology of luminescent material and benzanthracene, applied in luminescent materials, silicon organic compounds, organic chemistry, etc., can solve the problems of low cost, blue light materials cannot meet industrial production, etc., and achieve low cost, high yield, and film-forming performance. Good results

Active Publication Date: 2015-10-28
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem that the existing blue light materials cannot meet the requirements of industrial production, the present invention provides a silicon-containing benzanthracene-based organic light-emitting material with high luminous efficiency, low cost, high yield and purity, and its preparation method and application

Method used

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  • Silicon-containing benzanthracene-based organic light-emitting material and its preparation method and application
  • Silicon-containing benzanthracene-based organic light-emitting material and its preparation method and application
  • Silicon-containing benzanthracene-based organic light-emitting material and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of compound A101

[0038] The specific synthetic route is shown in the following formula:

[0039]

[0040] Mix silicon-containing benzanthracene bromide (B) 17.50 (50mol) g, N-phenyl-3-carbazolylboronic acid (A) 21.53 (75mol) g, sodium carbonate 15.90 (150mol) g, toluene 250ml and water Add 125ml into a three-necked flask, degas, add tetrakis(triphenylphosphine) palladium 0.57 (0.5mol)g, heat up to reflux, react for 24 hours, cool to room temperature, after the solid precipitates, filter with suction, and wash the filter cake with water and ethanol After washing with diethyl ether, drying to obtain 23.30 g of A101 product, the yield is over 93%, and the HPLC purity is over 98%. Mass Spectrum: Calculated 501.19; Found 501.15. Elemental analysis: Calculated value: C: 86.19%; H: 5.42%; N: 2.79%; Si: 5.60%; Tested value: C: 86.14%; H: 5.40%; N: 2.75%; Si: 5.58%.

Embodiment 2

[0041] Embodiment 2: the synthesis of compound B102

[0042] The specific synthetic route is shown in the following formula:

[0043]

[0044]Silicon-containing benzanthracene bromide (B) 17.50g (50mol), 4-(1,10-phenanthroline) naphthyl boronic acid (A) 31.52g (90mol), sodium carbonate 16.56g (160mol), toluene Add 250ml and 125ml of water into a three-neck flask, degas, add tetrakis(triphenylphosphine)palladium 0.69g (0.6mol), heat up to reflux, react for 25 hours, cool to room temperature, after the solid precipitates, filter with suction, and wash the filter cake with water After washing with ethanol and ether, dry to obtain 25.3 g of B102 product, the yield is more than 90%, and the HPLC purity is greater than 98%. Mass Spectrum: Calculated 564.20; Found 564.18. Elemental analysis: Calculated value: C: 85.07%; H: 5.00%; N: 4.96%; Si: 4.97%; Test value: C: 85.05%; H: 4.98%; N: 4.94%; Si: 4.95%.

Embodiment 3

[0045] Embodiment 3: the synthesis of compound B104

[0046] The specific synthetic route is shown in the following formula:

[0047]

[0048] 17.50g (50mol) of silicon-containing benzanthracene bromide (B), 41.52g (100mol) of 4-(4-triphenylamine)naphthylboronic acid (A), 18.02g (170mol) of sodium carbonate, 250ml of toluene and water Add 125ml into a three-necked flask, degas, add tetrakis(triphenylphosphine)palladium 0.80g (0.7mol), heat up to reflux, react for 26 hours, cool to room temperature, after the solid precipitates, filter with suction, and wash the filter cake with water and ethanol After washing with diethyl ether, 28.34 g of B104 product was obtained by drying, with a yield of more than 90% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 629.86; Found 629.84. Elemental analysis: Calculated value is C: 87.72%; H: 5.60%; N: 2.22; Si: 4.99%; Tested value is C: 87.73%; H: 5.61%; N: 2.21; Si: 4.98%.

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Abstract

The invention relates to a silicon-containing benzanthracene organic luminescent material, a preparation method and application thereof, and solves the problem that existing blue-light emitting materials cannot meet industrial production. With a benzanthracene compound as a basic skeleton, the organic luminescent material provided by the invention is obtained by taking a silicon-containing benzanthracene bromide and boric acid containing R1 and R2 substituents as raw materials, and subjecting them to Suzuki coupling reaction, and has the characteristics of good film-forming property and high luminous efficiency. The preparation method of the organic luminescent material changes the reaction solvent into a common solvent, is easy to operate and purify, greatly increases the yield, reduces the cost, and makes further development and application of the series of compounds possible, thus meeting the requirements of industrial production. The material can be used as an organic luminescent material, a luminescent host material or transport material in electroluminescent devices.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a silicon-containing benzanthracene organic light-emitting material and its preparation method and application. Background technique [0002] The preparation and device design of new organic and polymer optoelectronic materials is a very active field in the world. Compared with liquid crystal flat-panel displays, organic and polymer electroluminescent flat-panel displays (OLEDs and PLEDs) have significant characteristics such as active light emission, no angle dependence, good contrast, light, thin, and low energy consumption, and have broad application prospects. The primary colors red, green, and blue are necessary for an effective full-color display. Among them, blue light materials can be used as doped host materials for red and green light materials due to their wide energy gaps. In addition, blue light can also obtain red light and green light th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10C09K11/06C07F7/08H01L51/54
Inventor 马晓宇王辉李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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