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Benzofuran [2,3-b] pyrazine derivative as well as application thereof in organic electric fluorescent device

A technology of pyrazine derivatives and benzofuran, which is applied in the field of photoelectric materials and applications, can solve the problems of poor electron-withdrawing ability and limited types, and achieve the effect of high-efficiency electroluminescent performance

Active Publication Date: 2016-08-24
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the types of electron-withdrawing groups that can be used are very limited, so it is very important to design and invent new electron-withdrawing groups
[0003] As far as we know, benzofuran has a fixed conjugated structure and has good carrier transport ability, but its electron-withdrawing ability is far inferior to benzimidazoles, triazines, and boranes

Method used

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  • Benzofuran [2,3-b] pyrazine derivative as well as application thereof in organic electric fluorescent device
  • Benzofuran [2,3-b] pyrazine derivative as well as application thereof in organic electric fluorescent device
  • Benzofuran [2,3-b] pyrazine derivative as well as application thereof in organic electric fluorescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The chemical structure is The preparation method of benzofurano [2,3-b] pyrazine derivative (TPA-4-BFPz) is as follows:

[0023] Step 1: Add 5.0 grams of 2-methoxyphenylboronic acid, 8.3 grams of 3,5-dibromo-2-aminopyrazine, 13.6 grams of potassium carbonate, and 1.7 grams of tetraphenylphosphine palladium into a 500-ml flask, and then add Add 250 milliliters of toluene and 40 milliliters of water in the flask, reflux for 24 hours under the protection of argon, extract with ethyl acetate after cooling, spin dry after the organic layer is dried with anhydrous sodium sulfate, pass through the column with ethyl acetate / petroleum ether, Spin-dried to obtain 5.5 grams of 5-bromo-3-(2-methoxyphenyl)pyrazine-2-amino, with a yield of 60%;

[0024] Step 2: Add 4.5 grams of 5-bromo-3-(2-methoxyphenyl)pyrazine-2-amino to 20 milliliters of tetrahydrofuran and 40 milliliters of glacial acetic acid mixture, cool to minus 10 degrees Celsius, and then use constant Slowly add 6.6 gra...

Embodiment 2

[0027] The chemical structure is The preparation method of the benzofuro [2,3-b] pyrazine derivative is as follows:

[0028] Step 1 is the same as Step 1 in Example 1;

[0029] Step 2 is the same as Step 1 in Example 1;

[0030] Step 3: 2.4 grams of 2-bromobenzofuran (2,3-b) pyrazine, 5.38 grams of N, N-diphenyl-3-borate aniline, 6.0 grams of potassium carbonate, 0.6 grams of tetratriphenyl Phosphine palladium was added to a mixture of 200 ml of toluene and 20 ml of water, refluxed under argon for 48 hours, cooled to room temperature, extracted, spin-dried, and sublimated to obtain 2.0 g of benzofuro[2,3-b]pyrazine derivatives The yield was 50%.

Embodiment 3

[0032] The chemical structure is The preparation method of the benzofuro [2,3-b] pyrazine derivative is as follows:

[0033] Step 1 is the same as Step 1 in Example 1;

[0034] Step 2 is the same as Step 1 in Example 1;

[0035] Step 3: 2.4 grams of 2-bromobenzofuran (2,3-b) pyrazine, 4.0 grams of 9-phenyl-3-carbazole boronic acid, 6.0 grams of potassium carbonate, and 0.6 grams of tetraphenylphosphine palladium were added to In a mixed solution of 200 milliliters of toluene and 20 milliliters of water, reflux under argon for 48 hours, cool to room temperature, extract, spin dry, and sublimate to obtain 2.5 grams of benzofuro[2,3-b]pyrazine derivatives, the yield was 62.5%.

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Abstract

The invention provides a benzofuran [2,3-b] pyrazine derivative as well as application thereof in an organic electric fluorescent device. The chemical structural formula of the benzofuran [2,3-b] pyrazine derivative is as shown in the specification. In the formula, A is carbazole at different sites and a derivative of carbazole, triphenylamine at different sites and a derivative of triphenylamine, spirofluorene closed loop triphenylamine at different sites and a derivative of spirofluorene closed loop triphenylamine, spirofluorene at different sites and a derivative of spirofluorene, or acridine at different sites and a derivative of acridine. The benzofuran [2,3-b] pyrazine derivative provided by the invention can be used as a light emitting body to prepare the organic electric fluorescent device, an efficient electroluminescence property can be achieved, the maximum light emitting efficiency can be up to 11.5 Cantera per ampere, and the external quantum efficiency is up to 4.44%, which is approximate to the theoretical boundary value of 5% of a fluorescent material as the light emitting body in the organic electric fluorescent device.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to benzofurano[2,3-b]pyrazine derivatives and their application in organic electroluminescent devices. Background technique [0002] Since Professor Deng Qingyun and his collaborators proposed organic electroluminescent devices in 1987, fluorescent materials have been playing a pivotal role in this field. Especially in recent years, due to the proposal of thermally activated delayed fluorescence, fluorescent materials with electron-pushing groups-electron-withdrawing groups have become a hot spot again. Fluorescent materials with electron-pushing groups-electron-withdrawing groups have the characteristic that electron-withdrawing groups and electron-donating groups are connected by π bonds in structure. However, the types of electron-withdrawing groups that can be used at present are very limited, so it is very important to design and in...

Claims

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Application Information

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IPC IPC(8): C07D491/048C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D491/048C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1044H10K85/624H10K85/631H10K85/636H10K85/657H10K85/6572H10K50/00
Inventor 廖良生薛苗苗
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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