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Carbazole-containing compound and organic electroluminescent device thereof

A compound and carbazole technology, applied in the field of carbazole-containing compounds and organic electroluminescent devices, can solve the problems of poor application effect of blue light devices, adverse effects of organic materials, poor practicability, etc., to avoid adverse effects, improve Excellent luminous efficiency, stability and durability

Active Publication Date: 2020-10-16
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The material currently used for the cover layer is relatively single, and the practicability is poor, such as tris (8-hydroxyquinoline) aluminum (Alq 3 ) as the cover layer of green top-emitting devices can achieve better light extraction efficiency, but the application effect in blue light devices is not good
In addition, ultraviolet light in sunlight will enter the device through the semi-transmissive electrode, causing adverse effects on the organic materials inside the device

Method used

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  • Carbazole-containing compound and organic electroluminescent device thereof
  • Carbazole-containing compound and organic electroluminescent device thereof
  • Carbazole-containing compound and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0071] Preparation of Intermediate C:

[0072]

[0073] Compound A and compound B reacted through Suzuki coupling to obtain intermediate C;

[0074] Preparation of Intermediate E:

[0075]

[0076] Intermediate C and compound D were reacted by Suzuki coupling to obtain intermediate E;

[0077] The preparation of the compound containing carbazole shown in general formula (I):

[0078]

[0079] Intermediate E reacts with compound F via Buchwald-Hartwig to obtain a carbazole-containing compound represented by general formula (I).

[0080] Among them, the X 1 、X 2 independently selected from an oxygen atom or a sulfur atom;

[0081] Ar is selected from alkyl groups with 1 to 12 carbon atoms, aryl groups with 6 to 30 carbon atoms, heteroaryl groups with 3 to 30 carbon atoms, -NR 3 R 4 one of the R 3 , R 4 Independently selected from one of an aryl group with 6 to 30 carbon atoms and a heteroaryl group with 3 to 30 carbon atoms, the heteroaryl group contains at lea...

Synthetic example 1

[0105] Synthesis Example 1: Synthesis of Compound A

[0106] Synthesis of compound A-1:

[0107]

[0108] 3.25g (10mmol) 3,6-dibromocarbazole, 6.10g (24mmol) biboronic acid pinacol ester, 0.50g (0.6mmol) 1,1'-bis(diphenylphosphine)-ferrocene- Palladium dichloride (II) dichloromethane complex and 5.90 g (60 mmol) of potassium acetate were dissolved in 80 ml of toluene, and the reaction was carried out under reflux for 10 hours. Cool to room temperature, wash with distilled water, extract with toluene, filter the organic phase with a diatomaceous earth bed, distill off the organic solvent under reduced pressure, and recrystallize in heptane / toluene to obtain 3.73g (8.9mmol) of compound A-1, HPLC purity 99.5%, yield 89%.

[0109] Synthesis of compound A-2:

[0110]

[0111] Replace 3,6-dibromocarbazole with an equimolar amount of 2,7-dibromocarbazole, and the other steps are the same as those of compound A-1 to obtain 3.65g (8.7mmol) of compound A-2 , the HPLC purity wa...

Synthetic example 2

[0112] Synthesis Example 2: Synthesis of Compound 3

[0113]

[0114] 2.10g (5mmol) compound A-1, 2.12g (10mmol) compound B-1, 0.23g (0.2mmol) tetrakis (triphenylphosphine) palladium are dissolved in the mixed solvent of 30ml toluene and 15ml sodium carbonate aqueous solution (2M) In, reflux reaction for 8 hours. Cool to room temperature, extract with toluene, wash the organic phase with saturated brine, dry, and purify by column chromatography to obtain 1.67 g (3.9 mmol) of compound E-1, the HPLC purity is 99.0%, and the yield is 78%.

[0115] 0.86g (2mmol) compound E-1 was dissolved in the NMP of 20ml, then added 0.80g (2.6mmol) compound F-1, 0.28g (2mmol) sodium sulfate, 0.28g (2mmol) potassium carbonate and 0.04g (0.6 mmol) copper, reacted at 200°C for 24 hours. Cool to room temperature, remove the solvent by distillation under reduced pressure, wash with distilled water, and extract with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, then re...

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Abstract

The invention provides a carbazole-containing compound and an organic electroluminescent device thereof, and belongs to the technical field of organic photoelectric materials. In order to improve theluminous efficiency of the device and prolong the service life of the device, the carbazole-containing compound provided by the invention has high temperature resistance and ultraviolet light resistance, has good film stability and durability when being used as a covering layer, can effectively reduce the adverse effect of ultraviolet light in sunlight on organic materials in the device, thereby delaying the aging of the organic material and further prolonging the service life of the device; meanwhile, the carbazole-containing compound has a high refractive index, so that total reflection of light in the device can be reduced, and the luminous efficiency of the device is further improved. Therefore, the carbazole-containing compound provided by the invention is an OLED material with excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a compound containing carbazole and an organic electroluminescence device thereof. Background technique [0002] Compared with liquid crystal devices, organic light-emitting diodes (Organic Light-Emitting Diode, hereinafter referred to as OLEDs) have advantages such as high brightness, wide viewing angle, and high definition. Therefore, there are more and more researches on OLEDs. [0003] Deng Qingyun and others superimposed organic layers together to form a light-emitting device in 1987. On this basis, many OLED researchers have continuously optimized OLED devices and materials. So far, OLEDs are divided into two categories according to the direction of light emission: bottom-emitting devices and top-emitting devices. The light emission direction of the bottom emission device is from the side of the transparent anode, and the top emission device uses a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D417/14H01L51/52H01L51/54
CPCC07D413/14C07D417/14H10K85/624H10K85/622H10K85/615H10K85/626H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/858H10K2102/3026
Inventor 周雯庭孙可一苗玉鹤赵璐
Owner CHANGCHUN HYPERIONS TECH CO LTD
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