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Organic electroluminescent device comprising an electron buffer layer and an electron transport layer

A technology of electroluminescent devices and electron transport layers, which is applied in the fields of organic chemistry, luminescent materials, organic semiconductor devices, etc., can solve the problems of not specifically disclosing organic electroluminescent devices, etc., and achieve the effect of long life

Active Publication Date: 2022-02-11
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the above references fail to specifically disclose an organic electroluminescent device comprising a compound containing a nitrogen-containing heteroaryl group as an electron buffering material and a compound containing a 5-membered heteroaryl group fused to a phenanthrene as an electron transporting material.

Method used

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  • Organic electroluminescent device comprising an electron buffer layer and an electron transport layer
  • Organic electroluminescent device comprising an electron buffer layer and an electron transport layer
  • Organic electroluminescent device comprising an electron buffer layer and an electron transport layer

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0152] [Example 1] Preparation of compound C-24

[0153]

[0154] 1) Preparation of compound 1-1

[0155] In compound A (CAS: 1044146-16-8, 36g, 124mmol), 4-chloro-2-formylphenylboronic acid (25.2g, 136mmol), tetrakis (triphenylphosphine) palladium (5.7g, 5.0mmol) , sodium carbonate (33 g, 150 mmol), toluene (600 mL), EtOH (150 mL) and distilled water (150 mL) were added to the reaction vessel, and the mixture was stirred at 140° C. for 3 hours. After the reaction was completed, the precipitated solid was washed with distilled water and MeOH. The obtained compound 1-1 was used in the next reaction without further purification.

[0156] 2) Preparation of compound 1-2

[0157] After compound 1-1 (45.6 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.3 g, 217 mmol) and tetrahydrofuran (1500 mL) were introduced into the reaction vessel, the reaction mixture was stirred for 5 minutes, And then potassium tert-butoxide (KOtBu) (1 M in THF, 220 mL) was slowly ...

example 2

[0162] [Example 2] Preparation of compound C-1

[0163]

[0164] 1) Preparation of compound 2-1

[0165] Compound C (10g, 29mmol), bis(pinacolyl) diborane (8.8g, 34.8mmol), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3) (1.3g, 1.45mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (1.2g, 2.9mmol), potassium acetate (KOAc) (8.5g , 87 mmol) and 1,4-dioxane (150 mL) were added to the reaction vessel, and then the mixture was stirred at 140° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and then extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed therefrom with a rotary evaporator. The remaining product was purified by column chromatography to obtain compound 2-1 (10.4 g, yield: 82%).

[0166] 2) Preparation of compound C-1

[0167] In compound 2-1 (10g, 23.8mmol), 2-chloro-4,6-diphenyltriazine (CAS: 3842-55-5, 6.4g, 23.8mmol), three (d...

example 3

[0168] [Example 3] Preparation of compound C-17

[0169]

[0170] In compound C (8g, 23.1mmol), compound D (CAS: 1448296-00-1, 7.7g, 23.1mmol), tetrakis (triphenylphosphine) palladium (1.4g, 1.19mmol), K 2 CO 3 (8.2 g, 60 mmol), toluene (90 mL), EtOH (30 mL) and distilled water (30 mL) were added to the reaction vessel, and the mixture was stirred at 140° C. for 3 hours. After the reaction was completed, the precipitated solid was washed with distilled water and MeOH. The obtained compound was purified by column chromatography to obtain compound C-17 (8.7 g, yield: 77%).

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Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent devices of the present disclosure contain specific combinations of electron buffering materials and electron transporting materials that can provide high efficiency and / or long lifetime.

Description

technical field [0001] The present disclosure relates to an organic electroluminescent device comprising an electron buffer layer and an electron transport layer. Background technique [0002] An electroluminescent (EL) device is a self-luminous device that has the advantage of providing a wider viewing angle, greater contrast ratio, and faster response time. The first organic EL device was developed by Eastman Kodak by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer (see Appl. Phys . Lett.) "51, 913, 1987). [0003] An organic EL device converts electrical energy into light by injecting charges into an organic light-emitting material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of an organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (containing a host ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/54C09K11/06C07D417/04C07D413/04C07D413/10C07D403/04C07D403/10C07D487/04C07D491/06
CPCC07D413/04C07D417/04C07D487/04C09K11/06C07D413/14C07D417/14H10K85/615H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/11H10K2101/40H10K50/166H10K50/165H10K2101/30H10K50/16H10K50/18H10K50/171H10K85/626H10K50/15H10K2102/351
Inventor 安熙春文斗铉赵相熙
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC