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Blue-light semiconductor material containing dipyrazolopyrene, preparation method thereof, and organic light-emitting device made of the material

A dipyrazole and semiconductor technology, which is applied in the direction of semiconductor devices, semiconductor/solid-state device manufacturing, luminescent materials, etc., can solve the problems of device spectrum instability, achieve good electron transport performance, improve charge transfer ability, and low manufacturing cost Effect

Active Publication Date: 2017-03-08
奥来德(上海)光电材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims to solve the technical problem that the spectrum of devices made of existing pyrene-based blue-light materials is unstable under long-term or high-voltage conditions, and provides a blue-light semiconductor material containing bispyrazolopyrene, a preparation method thereof, and organic light emitting device

Method used

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  • Blue-light semiconductor material containing dipyrazolopyrene, preparation method thereof, and organic light-emitting device made of the material
  • Blue-light semiconductor material containing dipyrazolopyrene, preparation method thereof, and organic light-emitting device made of the material
  • Blue-light semiconductor material containing dipyrazolopyrene, preparation method thereof, and organic light-emitting device made of the material

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of compound 1

[0038]

[0039] Under nitrogen protection, put 100mmol of dipyrazolopyrene intermediate, 220mmol of 9-bromo-9H-carbazole, 5mmol of tris(dibenzylideneacetone)dipalladium, 400mmol of sodium tert-butoxide, and 20mmol of tri-tert-butylphosphine into a reaction vessel, and dissolved with 500ml of toluene, 110 ° C reflux reaction for 24h, with thin layer chromatography (TLC) to determine the end point of the reaction, the reaction is complete, cooled to room temperature, through a silica gel funnel, rinsed with dichloromethane, spin-dried, dichloromethane / Petroleum ether was recrystallized, filtered with suction, and dried to obtain 88 mmol of compound 1 with a yield of 88%.

Embodiment 2

[0040] Embodiment 2: the synthesis of compound 2

[0041]

[0042] Under the protection of nitrogen, put 100mmol of dipyrazolopyrene intermediate, 215mmol of 2-bromonaphthalene, tris(dibenzylideneacetone) dipalladium (5mmol), 409mmol of sodium tert-butoxide, and 20mmol of tri-tert-butylphosphine into the reaction In the container, dissolve it with 500ml toluene, reflux at 110°C for 24h, determine the end point of the reaction with thin layer chromatography (TLC), after the reaction is complete, cool to room temperature, pass through a silica gel funnel, rinse with dichloromethane, spin dry, dichloromethane / petroleum ether After recrystallization, suction filtration and drying, 79 mmol of compound 2 was obtained with a yield of 79%.

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 3

[0044]

[0045]Under the protection of nitrogen, put 102 mmol of dipyrazolopyrene intermediate, 219 mmol of 3-bromophenanthrene, 5 mmol of tris(dibenzylideneacetone) dipalladium, 404 mmol of sodium tert-butoxide, and 20 mmol of tri-tert-butylphosphine into a reaction vessel , and dissolved in 500ml of toluene, reflux at 110°C for 24h, use thin-layer chromatography (TLC) to determine the end point of the reaction, after the reaction is complete, cool to room temperature, pass through a silica gel funnel, rinse with dichloromethane, spin dry, dichloromethane / petroleum ether recrystallization , filtered by suction, and dried to obtain 74mmol of compound 3, with a yield of 73%.

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Abstract

The invention relates to a blue-light semiconductor material containing bispyrazolopyrene, a preparation method thereof, and an organic light-emitting device made of the material, which solves the problem that the spectrum of devices made of existing pyrene-based blue-light materials is under long-term or high-voltage conditions Unstable technical issues. The blue-light semiconductor material containing bispyrazolopyrene provided by the present invention reacts bispyrazolopyrene with bromide containing R groups to generate bispyrazolopyrene derivatives containing R substituents. The prepared blue-light semiconductor material containing dipyrazolopyrene has high luminous efficiency, and the high luminous efficiency indicates that the compound can be used as a light-emitting material or a light-emitting host material, especially as a phosphorescent blue host material for organic electroluminescence. The light-emitting device exhibits high efficiency, high brightness and long life, and has the advantages of low manufacturing cost, which reduces the manufacturing cost of the organic electroluminescent device.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a blue-light semiconductor material containing bispyrazolopyrene, a preparation method thereof, and an organic light-emitting device made of the material. Background technique [0002] An organic electroluminescent EL device is hereinafter referred to as an "organic EL device" and generally consists of two opposing electrodes and at least one layer of organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form electron and hole pairs, which cause light emission from organic compounds having fluorescent or phosphorescent properties. [0003] Organic light-emitting diode (OLED) is a new type of flat-panel display device, which has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D487/06C07D519/00C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1007H10K85/631H10K85/626H10K85/657H10K85/6574H10K85/6572
Inventor 尹恩心林文晶
Owner 奥来德(上海)光电材料科技有限公司
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