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Organic blue luminescent material, and preparation method and application thereof

A blue light-emitting material and a technology for light-emitting materials, which are applied in the field of organic blue light-emitting materials and their preparation, can solve the problem that blue light materials cannot meet industrial production, and achieve the effects of improving light-emitting efficiency, low preparation cost, and good film-forming performance.

Active Publication Date: 2014-05-21
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problem that the existing blue light materials cannot meet the requirements of industrial production, the present invention provides an organic blue light emitting material with high luminous efficiency, low cost, high yield and purity, its preparation method and application

Method used

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  • Organic blue luminescent material, and preparation method and application thereof
  • Organic blue luminescent material, and preparation method and application thereof
  • Organic blue luminescent material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the synthesis of compound 001

[0032] The specific synthetic route is shown in the following formula:

[0033]

[0034] 26.41g of 3-bromo-9-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene, 44.72g of (10-phenyl-9-anthracenyl)boronic acid, 20g of sodium carbonate, Put 250ml of tetrahydrofuran and 125ml of water into a three-necked flask, degas, add 0.9g of tetrakis(triphenylphosphine)palladium, heat up to 70°C, reflux for 30 hours, cool to room temperature, after the solid precipitates, suction filter, filter cake through water, After washing with ethanol and ether, drying to obtain 56.17 g of asymmetric benzanthracene derivatives with the chemical structure formula 001, the yield is over 92%, and the HPLC purity is over 98%. Mass Spectrum: Calculated 875.10; Found 875.05. Elemental analysis: calculated value C: 94.70%; H: 5.30%; test value C: 94.73%; H: 5.27%.

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 002

[0036] The specific synthetic route is shown in the following formula:

[0037]

[0038] Add 26.41g of 3-bromo-9-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene, 22.32g of 6-indenylboronic acid, 20g of sodium carbonate, 250ml of tetrahydrofuran and 125ml of water into three ports bottle, degassed, added 0.9 g of tetrakis(triphenylphosphine)palladium, raised the temperature to 100°C, refluxed for 5 hours, cooled to room temperature, and after the solid precipitated, suction filtered, the filter cake was washed with water, ethanol and ether, and dried After drying, 25.18 g of asymmetric benzanthracene derivatives of the chemical structural formula 002 were obtained, with a yield of more than 93% and an HPLC purity of more than 98%. Mass spectrum: calculated value 598.77; found value 598.75. Elemental analysis: calculated value C: 94.28%; H: 5.72%; test value C: 94.26%; H: 5.74%.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 003

[0040] The specific synthetic route is shown in the following formula:

[0041]

[0042] Add 26.41g of 3-bromo-9-(4-bromonaphthyl)-7,7-dimethyl-7H-benzoanthracene, 29.10g of 3-fluorenylboronic acid, 20g of sodium carbonate, 250ml of tetrahydrofuran and 125ml of water into three ports bottle, degassed, added tetrakis(triphenylphosphine)palladium 0.9g, raised the temperature to 75°C, refluxed for 24 hours, cooled to room temperature, after the solid precipitated, suction filtered, the filter cake was washed with water, ethanol and ether, and dried Dry to obtain 28.44 g of asymmetric benzanthracene derivatives with chemical structural formula 003, the yield is over 90%, and the HPLC purity is greater than 98%. Mass Spectrum: Calculated 698.89; Asserted 698.87. Elemental analysis: calculated value C: 94.52%; H: 5.48%; test value C: 94.50%; H: 5.50%.

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Abstract

The invention relates to an organic blue luminescent material, and a preparation method and application thereof. The invention solves the problem that the existing blue light material can not satisfy the industrial production. The material is a compound prepared by carrying out Suzuki coupling reaction on 3-bromo-9-(4-bromonaphthyl)-7,7-dimethyl-7H-benzanthracene and boric acid containing A substituent group. The material has the advantages of favorable film-forming properties and higher luminescence efficiency, and can emit light blue light; and therefore, the organic blue luminescent material has much higher properties than simple benzanthracene, and the prepared blue light device can satisfy the demands for industrial production. The preparation method greatly enhances the yield, is convenient for operation and easy for purification, and lowers the cost, so that the material has more possibility for further development and application. The material can be used as an organic luminescent material, luminescent main body material or transmission material in an electroluminescent device.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an organic blue light-emitting material and its preparation method and application. Background technique [0002] As a flat-panel display technology, organic electroluminescent devices have many advantages such as self-luminescence, high brightness, wide viewing angle, ultra-thin, low energy consumption, fast response, rollable, and full-color luminescence. Therefore, in the last two decades, the device has achieved rapid development, and its industrialization process is also constantly advancing. But on the whole, there are still many key technical problems that have not been resolved. From the perspective of materials alone, red, green, and blue light materials with excellent performance are the primary conditions for realizing full-color display. However, as far as the current research on organic electroluminescent materials is concerned, in addition to the goo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C13/66C07C1/32C07D213/127C07D277/66C07D263/56C07D307/79H01L51/54
Inventor 马晓宇王辉刘成凯
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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