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Compounds and organic electroluminescent devices

An electroluminescence device and compound technology are applied in the application field of the compound in the field of organic electroluminescence display and lighting technology, and can solve the problems of reducing the recombination probability, increasing the working voltage of the device, reducing the luminous efficiency of the device, and the like

Active Publication Date: 2019-11-08
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Generally speaking, most electron transport materials have high electron affinity, so they have a strong ability to accept electrons, but compared with hole transport materials, common electron transport materials such as AlQ 3 The electron mobility of (octahydroxyquinoline aluminum) is much lower than the hole mobility of the hole transport material, so in OLED devices, on the one hand, it will cause the injection and transport of carriers to be unbalanced and cause the gap between holes and electrons. The recombination probability of the device is reduced, thereby reducing the luminous efficiency of the device. On the other hand, the electron transport material with lower electron mobility will lead to an increase in the operating voltage of the device, thereby affecting the power efficiency, which is not good for energy saving.

Method used

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  • Compounds and organic electroluminescent devices
  • Compounds and organic electroluminescent devices
  • Compounds and organic electroluminescent devices

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] Th...

Embodiment 1

[0126] Example 1: Preparation of compound 1-121

[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 dropping process kept the temperature 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 respectively, and dried in the 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 dr...

Embodiment 2

[0138] Example 2: Preparation of compound 1-124

[0139]

[0140]

[0141] Preparation of compound 2-1

[0142] The compound 5-bromo-2,4-dichloropyrimidine (45.2g, 200mmol) was added into a flask containing 500mL of ethanol, and hydrazine hydrate (37.5g, 600mol, 80% aqueous solution) was added dropwise at 5°C under stirring. Keep the temperature 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 the air to obtain compound 2-1 (33.3 g, 75%) as an off-white solid.

[0143] Preparation of compound 2-2

[0144] Compound 2-1 (33.3g, 0.15mol) was added to a flask containing 350mL of ethanol, and benzaldehyde (20.7g, 0.2mol) was added dropwise under stirring at room temperature. Rinse with ethanol and n-hexane, and dry to obtain compound 2-2 (28 g, 60%) as a yellow solid.

[0145] Preparation of compound 2-3

[0146] Com...

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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, phenanthrenyl, substituted or unsubstituted anthracenyl, the substituents of the anthracenyl are selected from phenyl, biphenyl, terphenyl, 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 compound, an organic electroluminescence device using the compound, and the application of the compound in the field of organic electroluminescence display and lighting technology. Background technique [0002] At present, with the continuous advancement of OLED technology in the two major fields of lighting and display, people are paying more attention to the research on its core materials. An organic electroluminescent device with high efficiency and long life is usually the result of an optimized combination of device structure and various organic materials. Results Common functional organic materials include: hole injection materials, hole transport materials, electron injection materials, electron transport materials, luminescent host materials and luminescent guest (dye) and so on. In order to prepare light-emitting devices with better performance, the industry has been committed to developing new organic el...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D471/14C07D495/14H01L51/50H01L51/54
CPCC07D471/14C07D487/04C07D495/14H10K85/615H10K85/657H10K85/6572H10K50/16
Inventor 孙恩涛刘嵩邢其锋张向慧
Owner BEIJING ETERNAL MATERIAL TECH
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