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Compounds and their applications in the field of organic electroluminescence

A technology for electroluminescent devices and compounds, applied in the directions of organic chemistry, luminescent materials, circuits, etc., can solve the problem of not specifically disclosing organic electroluminescent compounds, etc.

Active Publication Date: 2020-02-21
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above references do not specifically disclose an organic electroluminescent compound in which a compound represented by the general formula (I) described later is introduced as an electron-deficient group into the structure of a host material.

Method used

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  • Compounds and their applications in the field of organic electroluminescence
  • Compounds and their applications in the field of organic electroluminescence
  • Compounds and their applications in the field of organic electroluminescence

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0119] Preparation of intermediate M1:

[0120]

[0121] Using 2,4-dichloropyrimidine (or its derivatives) as the starting material, first react with hydrazine hydrate to replace the 4-position chlorine atom with relatively high activity of 2,4-dichloropyrimidine (or its derivatives) to generate Intermediate A. Intermediate A further condenses with aldehyde to remove a molecule of water to generate intermediate B. Intermediate B reacts with iodobenzene acetate for oxidative ring closure to generate the first type of intermediate M1.

[0122] Preparation of Intermediate M2:

[0123]

[0124] Using 2,4-dichloropyrimidine (or its derivatives) as the starting material, first react with ammonia water to replace the highly active 4-position chlorine atom of 2,4-dichloropyrimidine (or its derivatives) to generate intermediate C . Intermediate C is further reacted with α-bromo(hetero)aryl or alkyl ethyl ketone to generate the second type of intermediate M2.

[0125] The syn...

Embodiment 1

[0126] Embodiment 1: the preparation of compound 1I-12

[0127]

[0128] Preparation of Compound 1-1

[0129] After dissolving 2,4-dichloropyrimidine (500g, 3.38mol) in 10L ethanol in a flask, hydrazine hydrate (634g, 10.14mol, 80% aqueous solution) was added dropwise at 5°C under stirring, and the temperature was kept below 10°C. After the dropwise addition, the mixture was naturally raised to room temperature for 1 hour, and the precipitated solid was filtered with suction, washed with water and ethanol, and dried in air to obtain compound 1-1 (389 g, 80%) as an off-white solid.

[0130] Preparation of compound 1-2

[0131] Compound 1-1 (144g, 1mol) was added to a flask containing 1.5L of ethanol, and benzaldehyde (138g, 1.3mol) was added dropwise under stirring at room temperature. After the addition was complete, stirring was continued for 30 minutes, and the obtained solid was filtered and washed with ethanol and Rinse with n-hexane and dry to obtain compound 1-2 (1...

Embodiment 2

[0138] Embodiment 2: the preparation of compound 1II-12

[0139]

[0140] Preparation of compound 2-1

[0141] Add p-chlorophenylboronic acid (7.8g, 50mmol), compound 1-3 (11.5g, 50mmol), potassium carbonate (20.7g, 150mmol) into a flask containing 1,4-dioxane / water (300mL / 100mL) , Pd(PPh 3 ) 4 (578 mg, 0.5 mmol). After the addition was completed, the mixture was reacted at 80° C. for 8 hours under stirring, and the end point of the reaction was monitored by TLC. Separate the liquids, extract the aqueous phase with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, and spin off the solvent under reduced pressure. Compound 2-1 (10.7 g, yield 70%) was obtained by separation and purification by column chromatography.

[0142] Preparation of compound 1II-12

[0143] Add compound 2-1 (6.12g, 20mmol), compound 1-4 (8.46g, 20mmol), sodium tert-butoxide (5.8g, 60mmol) into a flask containing 200mL xylene, and add Pd under stirring under a ...

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Abstract

The present invention provides a compound represented by the following general formula (I) or (II): wherein, X is selected from CR 4 or N; R 1 ~R 4 independently selected from hydrogen, C1-C10 alkyl, substituted or unsubstituted C5-C60 aryl or heteroaryl, the aryl or heteroaryl substituents are selected from deuterium, fluorine, methyl, Methoxy, cyano, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, furyl, thienyl, indenyl, benzofuryl, benzothienyl, substituted or unsubstituted indolyl , dibenzofuryl, dibenzothienyl, substituted or unsubstituted carbazolyl, benzocarbazolyl, dibenzocarbazolyl, the substituents of the indolyl and carbazolyl are selected from benzene Base, biphenyl, naphthyl, phenanthrenyl; The dotted line and Cy in the general formula (II) represent a five-membered or six-membered aromatic ring or aromatic heterocyclic ring fused to a pyrimidine ring. The compound can be used in organic electroluminescent devices. The present invention also provides an organic electroluminescent device comprising the above compound.

Description

technical field [0001] The present invention relates to a new class of organic heterocyclic compound and the application of the compound in organic electroluminescent devices. Background technique [0002] In recent years, organic light-emitting devices based on phosphorescent metal complexes have developed rapidly. Different from traditional small organic molecules and conjugated polymer materials, transition metal complexes can simultaneously obtain singlet and triplet excitons, achieving a theoretical maximum internal quantum efficiency of 100% (non-patent document 1). [0003] In classic phosphorescent OLED devices, in addition to luminescent dyes, host materials are also indispensable. Phosphorescent dyes are usually not used alone as a light-emitting layer, but are doped in a suitable host material to form a host-guest light-emitting system to weaken the high-concentration quenching effect of triplet excitons. In order to achieve effective energy transfer, it is gene...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/00H01L51/54C09K11/06C07D487/04C07D471/14C07D495/14
CPCC09K11/06C07D471/14C07D487/04C07D495/14C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/1088H10K85/657H10K85/6572
Inventor 孙恩涛刘嵩高文正张向慧
Owner BEIJING ETERNAL MATERIAL TECH
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