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Spirobifluorene compound, electron transport composition and organic electroluminescent device

A technology of electron transport and electron transport layer, which is used in electric solid devices, electrical components, organic chemistry, etc. It can solve the problems of short life and high evaporation temperature, and achieve the effect of prolonging life, reducing evaporation temperature and ensuring stability.

Pending Publication Date: 2022-04-22
CHANGZHOU TRONLY EARLY OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The main purpose of the present invention is to provide a spirobifluorene compound, an electron transport composition and an organic electroluminescent device to solve the problems of high evaporation temperature and short life of the organic electroluminescent device in the prior art

Method used

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  • Spirobifluorene compound, electron transport composition and organic electroluminescent device
  • Spirobifluorene compound, electron transport composition and organic electroluminescent device
  • Spirobifluorene compound, electron transport composition and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0049] In a three-necked flask, add 2-bromo-2'-chloro-9,9'-spirobifluorene (30.0g, 69.8mmol), bisboronic acid pinacol ester (18.6g, 73.3mmol) and 1,4-di Hexane (300mL), filled with nitrogen and stirred for 15 minutes, then added potassium acetate (13.8g, 139.6mmol), 1,1'-bis(diphenylphosphine)ferrocenedichloropalladium(II) (1.0g , 1.4mmol), heated to reflux for 2.5 hours. After the reaction was completed, cool to room temperature, filter with silica gel, and evaporate the filtrate to remove the solvent in vacuo to obtain the crude product, which was slurried with n-hexane / toluene (V:V=10:3) for 1 hour, suction filtered, and washed twice with n-hexane to obtain 30.0 g of compound I-1 was off-white solid powder, with a yield of 81% and a purity of 99.02%.

[0050] In a three-necked flask, add intermediate I-1 (30.0g, 62.9mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (16.8g, 62.9mmol), potassium carbonate ( 26.0g, 157.2mmol), tetrakis-(triphenylphosphine)palladium (1.4g), toluene...

preparation Embodiment 2

[0057] In a three-necked flask, add intermediate I-1 (30.0g, 62.9mmol), 2-chloro-4,6-bis(9,9'-dimethylfluorene)-1,3,5-triazine (31.5 g, 62.9 mmol), potassium carbonate (26.0 g, 157.2 mmol), tetrakis-(triphenylphosphine) palladium (1.4 g), toluene (250 mL), ethanol (50 mL) and water (80 mL), heated under nitrogen Reflux for 10 hours. After the reaction was completed, cool to room temperature, extract with toluene and water, take the organic layer and filter it with silica gel, evaporate the filtrate to remove the solvent in vacuo to obtain a crude product, which was recrystallized with a mixed solvent of dichloromethane / ethanol to obtain 46 g of compound I as a white solid powder -4, the yield was 90%, and the purity was 99.7%.

[0058] In a three-necked flask, add intermediate I-4 (42.0g, 51.6mmol), pinacol diboronate (15.7g, 61.9mmol) and toluene (300mL), fill with nitrogen and stir for 15 minutes, then add potassium acetate (10.1 g, 103.2 mmol), tris(dibenzylidene indeneac...

preparation Embodiment 3

[0064]In a three-necked flask, add intermediate I-1 (30.0g, 62.9mmol), 2-chloro-4,6-bis(1-naphthyl)-1,3,5-triazine (23.14g, 62.9mmol) , potassium carbonate (26.0g, 157.2mmol), tetrakis-(triphenylphosphine)palladium (1.4g), toluene (250mL), ethanol (50mL) and water (80mL), heated to reflux for 10 hours under nitrogen protection. After the reaction is completed, cool to room temperature, extract with toluene and water, take the organic layer and filter it with silica gel, evaporate the filtrate to remove the solvent in vacuo to obtain a crude product, which is recrystallized with a mixed solvent of dichloromethane / ethanol to obtain 40 g of compound I as a white solid powder -6 with a yield of 93% and a purity of 99.2%.

[0065] In a three-necked flask, add intermediate I-6 (35.0g, 51.6mmol), pinacol diborate (15.7g, 61.9mmol) and toluene (500mL), fill with nitrogen and stir for 15 minutes, then add potassium acetate (10.1 g, 103.2 mmol), tris(dibenzylidene indeneacetone) dipall...

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Abstract

The invention provides a spirobifluorene compound, an electron transport composition and an organic electroluminescent device. The spirobifluorene compound has the following general formula I, wherein R1 and R2 are respectively and independently selected from any one of H, substituted or non-substituted straight-chain alkyl of C1-C10, substituted or non-substituted branched alkyl of C3-C10, and substituted or non-substituted aryl of C6-C30, and R1 and R2 are respectively and independently selected from any one of H, substituted or non-substituted straight-chain alkyl of C1-C10, substituted or non-substituted branched alkyl of C3-C10 and substituted or non-substituted aryl of C6-C30; r3 and R4 are respectively and independently selected from any one of H, C1-C4 straight-chain alkyl, isopropyl and tert-butyl, and at least one of R3 and R4 is H; ar is selected from a substituted or unsubstituted fused aromatic ring group or a fused heteroaromatic ring group of C8-C18, and fused aryl carbon in Ar is combined with spirobifluorene. When the spirobifluorene compound is used as an electron transport material in an organic electroluminescent device, the evaporation temperature of the device is reduced, the working voltage of the device is reduced, and the service life of the device is prolonged.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a spirobifluorene compound, an electron transport composition and an organic electroluminescence device. Background technique [0002] Organic light emitting diodes (organic light emitting diodes, OLED) have the advantages of lightness, thinness, self-luminescence, low power consumption, no backlight, wide viewing angle, fast response and flexibility, and have gradually replaced liquid crystal display panels to become a new generation flat panel display, and also has great potential in flexible display. The carrier mobility of traditional electron transport materials is one-thousandth of that of hole transport materials, and their thermal stability is not good, which often leads to the problem of rapid roll-off of luminous efficiency or poor device life. According to relevant literature, the charge consumption ratio of electron transport materials is up to 35...

Claims

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Application Information

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IPC IPC(8): C07D403/10C07D405/10C07D409/10H01L51/50H01L51/54
CPCC07D403/10C07D405/10C07D409/10H10K85/615H10K85/624H10K85/654H10K85/6576H10K85/6572H10K85/6574H10K50/16
Inventor 陈俊蓉孙霞王仁宗周宇
Owner CHANGZHOU TRONLY EARLY OPTOELECTRONICS MATERIAL CO LTD
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