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Benzanthracene organic light-emitting material and preparation method thereof

A technology of luminescent materials, benzanthracene, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc.

Inactive Publication Date: 2013-06-12
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing materials still have application problems, such as lifespan, brightness, and efficiency. How to develop materials with excellent performance is the top priority.

Method used

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  • Benzanthracene organic light-emitting material and preparation method thereof
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  • Benzanthracene organic light-emitting material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthesis of compound 001

[0020] The specific synthetic route is shown in the following formula:

[0021]

[0022] 22.47g (50mmol) of 3-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene, 21.69g (75mmol) of N-phenylcarbazolylboronic acid, 10.60g (100mmol) of sodium carbonate ), 250ml of tetrahydrofuran and 125ml of water were added to a three-necked flask, degassed, added 0.58g (0.5mmol) of tetrakis(triphenylphosphine) palladium, heated to 70°C, reacted for 15 hours, cooled to room temperature, and after the solid precipitated, suction filtered, The filter cake was washed with water, ethanol and ether, and then dried to obtain 28.45 g of asymmetric benzanthracene derivatives, with a yield of over 93% and an HPLC purity of over 98%. Mass Spectrum: Calcd. 611.77; Tested 611.74. Elemental Analysis: Calcd: C: 92.27%; H: 5.44%; N: 2.29%; Tested: C: 92.25%; H: 5.45%; N: 2.30%.

[0023]

Embodiment 2

[0024] Embodiment 2: the synthesis of compound 002

[0025] The specific synthetic route is shown in the following formula:

[0026]

[0027] 22.47g (50mmol) of 3-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene, 17.92g (80mmol) of phenanthrene boronic acid, 12.19g (115mmol) of sodium carbonate, 250ml of tetrahydrofuran and Add 125ml of water into a three-necked flask, degas, add tetrakis(triphenylphosphine)palladium 0.69g (0.6mmol), raise the temperature to 80°C, react for 17 hours, cool to room temperature, after the solid precipitates, suction filter, the filter cake is washed with water, After washing with ethanol and ether, 25.51 g of asymmetric benzanthracene derivatives were obtained by drying, with a yield of more than 93% and a purity of more than 98% by HPLC. Mass spectrum: calculated value 548.67; found value 548.66. Elemental analysis: calculated value C: 89.75%; H: 5.14%; N: 5.11%; tested value C: 89.73%; H: 5.15%; N: 5.12%.

[0028]

Embodiment 3

[0029] Embodiment 3: the synthesis of compound 003

[0030] The specific synthetic route is shown in the following formula:

[0031]

[0032] 22.47g (50mmol) of 3-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene, 15.04g (85mmol) of 2-methylbenzoxazolylboronic acid, and 13.78g of sodium carbonate (130mmol), 250ml of tetrahydrofuran and 125ml of water were added to a three-necked flask, degassed, added 0.81g (0.7mmol) of tetrakis(triphenylphosphine)palladium, heated to 85°C, reacted for 19 hours, cooled to room temperature, and after the solid was precipitated, pumped After filtering, the filter cake was washed with water, ethanol and ether, and then dried to obtain 23.14 g of asymmetric benzanthracene derivatives, with a yield of more than 93% and an HPLC purity of more than 98%. Mass spectrum: Calculated value is 501.62; found value is 501.64. Elemental analysis: calculated value C: 88.59%; H: 5.43%; N: 2.79%; O: 3.19%; tested value C: 88.59%; H: 5.42%; N: 2.78%;

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Abstract

A benzanthracene organic light-emitting material is characterized by having a following general structural formula. A group A is a substituted or unsubstituted aryl group forming into a ring and with carbon number of 6-30. The synthesis method provided by the invention is simple, low-cost, easy for purification, and has high yield and good performance in luminous efficiency, brightness, driving voltage, life and stability; the material can be prepared into a display device for application; and at the same time, luminescence peak position can be adjusted.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to organic electroluminescent materials containing novel benzanthracene derivatives. Background technique [0002] Organic electroluminescent technology is the latest generation of flat-panel display technology, which can be used for flat-panel displays and lighting sources. At present, commercial flat-panel displays have been put into the market. Due to its own absolute advantages, the lighting source will soon be industrialized. The electroluminescent device has an all-solid structure, and the organic electroluminescent material is the core and basis of the device. The development of new materials is the driving force behind the continuous progress of electroluminescent technology. The preparation of original materials and device optimization are also research hotspots in the organic electroluminescent industry. [0003] At present, the development of OLED (organi...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C07D471/04C07D263/56C07C13/66C07C1/32
Inventor 马晓宇王辉姜晓晨
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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