Novel compound and organic electroluminescent device including the same

A technology of organic light-emitting devices and compounds, applied in the field of novel compounds and organic electroluminescent devices containing them, can solve the problems of high driving voltage, low efficiency, short life, etc., achieve high color purity, high luminous efficiency, and prolong life Effect

Active Publication Date: 2018-06-05
DONGJIN SEMICHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, many compounds have been known as substances used in such organic light-emitting devices, but in the case of organic light-emitting devices using hitherto known substances, there is a continuous demand for high driving voltage, low efficiency and short life. develop new materials

Method used

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  • Novel compound and organic electroluminescent device including the same
  • Novel compound and organic electroluminescent device including the same
  • Novel compound and organic electroluminescent device including the same

Examples

Experimental program
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Effect test

no. 1 approach

[0035] The first embodiment of the present invention provides a compound represented by the following chemical formula 1:

[0036] chemical formula 1

[0037]

[0038] In the above chemical formula, X is O or S, L 1 and L 2 are independently directly coupled, substituted or unsubstituted C 6 -C 30 Arylene or substituted or unsubstituted C 3 -C 30 Heteroarylene, Ar 1 to Ar 4 are independently substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 3 -C 30 In the heteroaryl group, m and n are each independently 0 or 1, and the sum of m and n is 1 or more.

[0039] In an example of the present invention, in the compound of the above chemical formula 1, the third position of carbazole is fixed at the second position of the dibenzofuran or dibenzothiophene structure, and in the case of changing this binding position, For example, in the case of combining with the fourth position of the dibenzofuran or dibenzothiophene structure, relatively low T...

Synthetic example 1

[0179] Synthesis Example 1: Synthesis of Intermediate (I-1)

[0180]

[0181] Under argon or nitrogen atmosphere, in 65.2g (200mM) of 2,8-dibromodibenzo[b,d]furan, 60.3g (210mM) of (9-phenyl-9H-carbazol-3-yl ) boric acid, 4.7g (4mM) tetrakis (triphenylphosphine) palladium (0), add 600ml of toluene, concentration of 2M Na 2 CO 3 300ml of aqueous solution was heated under reflux for 15 hours. After the reaction is over, use dichloromethane (dichloromethane) to extract, and put MgSO 4 to filter. After removing the solvent of the filtered organic layer, purification was performed by column chromatography to obtain 58.7 g of intermediate I-1 (3-(8-bromodibenzo[b,d]furan-2-yl)-9- phenyl-9H-carbazole) (yield 61%).

[0182] m / z: 487.06 (100.0%), 489.06 (96.4%), 488.06 (33.2%), 490.06 (32.1%), 491.06 (4.7%), 489.06 (2.3%), 489.06 (1.4%), 489.06 (0.8%) )

Synthetic example 2

[0183] Synthesis Example 2: Synthesis of Intermediate (I-2)

[0184]

[0185] Under argon or nitrogen atmosphere, in 84.0g (200mM) of 2,8-diiododibenzo[b,d]furan, 60.3g (210mM) of (9-phenyl-9H-carbazol-3-yl ) boric acid, 4.7g (4mM) tetrakis (triphenylphosphine) palladium (0), add 600ml of toluene, concentration of 2M Na 2 CO 3 300ml of aqueous solution was heated under reflux for 10 hours. After the reaction, use dichloromethane to extract, and put MgSO 4 to filter. After removing the solvent of the filtered organic layer, it was purified by column chromatography to obtain 42.8 g of intermediate 1-2(3-(8-iodobenzo[b,d]furan-2-yl)-9-benzene base-9H-carbazole) (yield 39%).

[0186] m / z: 535.04 (100.0%), 536.05 (31.7%), 537.05 (2.3%), 537.05 (1.9%)

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Abstract

The invention relates to a novel compound comprising carbazole, dibenzofuran, or dibenzothiophene and an organic electroluminescent device including the same.

Description

technical field [0001] The present invention relates to novel compounds and organic electroluminescent devices comprising them. Background technique [0002] In organic light emitting diodes, materials used as organic layers can be roughly classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. according to functions. Moreover, the above-mentioned luminescent materials can be classified into high molecular weight and low molecular weight according to the molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to the light emitting mechanism. Luminescent colors are classified into blue, green, red luminescent materials and yellow and orange luminescent materials required to reflect better natural colors. Also, in order to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D409/04C09K11/06H01L51/54H10K99/00
CPCC09K11/06C07D405/04C07D409/04C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1014C09K2211/1011H10K85/615H10K85/631H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/6572Y02E10/549C07C211/54H10K50/11H10K50/17
Inventor 权桐热安贤哲咸昊完姜京敏金熙宙金东骏闵丙哲金槿泰韩政佑林东焕林大喆
Owner DONGJIN SEMICHEM CO LTD
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