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Novel compound and organic electroluminescent device including the same

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

Pending Publication Date: 2019-03-19
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
Comparison scheme
Effect test

preparation example 1

[0150] The synthesis of preparation example 1.IM

[0151] The intermediate IM for the synthesis of the target compound can be synthesized as follows, but not limited thereto.

[0152] h = halogen atom

[0153]

[0154] h = halogen atom

[0155]

[0156] h = halogen atom

[0157] or

[0158] h = halogen atom

[0159]

[0160] The reactant IM1 used to synthesize the target compound was synthesized as follows:

[0161] The synthesis method of the following IM1 is as follows.

[0162]

[0163] In a round bottom flask, dissolve 27.6 g of [1,1'-biphenyl]-4-ylboronic acid and 50.0 g of 4-bromo-4'-iodo-1,1'-biphenyl in 1,4- Dioxane (1,4-dioxan) 800ml, put K 2 CO 3 (2M)210ml and Pd(PPh 3 ) 4 After 4.8 g, reflux and stir. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated after adding water. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then recrystallized to obtain 15...

preparation example 2

[0167] Preparation Example 2: Synthesis of OP

[0168] The following synthesis method of OP1 is as follows.

[0169]

[0170] In a round bottom flask, 10.0 g of the above-mentioned 3-bromo-9,9-diphenyl-9H-fluorene, 3.8 g of aniline, 5.3 g of t-BuONa, Pd 2 (dba) 3 1.4g, (t-Bu) 3 1.6 ml of P was dissolved in 150 ml of toluene, and stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated after adding water. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then recrystallized to obtain 7.3 g of OP1 (yield 70%).

[0171] Using the same method as OP1 above, using different starting materials, the following OP2 to OP5 were synthesized.

[0172]

[0173]

Synthetic example 1

[0174] Synthesis Example 1. Synthesis of Compound 1

[0175]

[0176] In a round bottom flask, IM1 7.0g, OP1 5.2g, t-BuONa 2.6g, Pd 2 (dba) 3 0.7g, (t-Bu) 3 P0.7ml was dissolved in 200ml of toluene, and stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated after adding water. The organic layer was extracted with methylcellulose (MC) and filtered under reduced pressure, followed by column purification and recrystallization to obtain 7.07 g of Compound 1 (yield 66%).

[0177] m / z: 589.28 (100.0%), 590.28 (49.1%), 591.28 (11.8%), 592.29 (1.8%)

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Abstract

The present invention relates to a novel arylamine compound. When used as a hole transport layer (HTL), a light emitting auxiliary layer (HT) or a hole injection layer (HIL), hole injection and transport properties can be increased, and therefore high efficiency and long service lifetime effects of the device can be provided.

Description

technical field [0001] The present invention relates to novel arylamine compounds and organic light-emitting devices comprising the same. 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...

Claims

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Application Information

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IPC IPC(8): C07C211/61C09K11/06H01L51/54
CPCC09K11/06C07C211/61C07C2603/18C09K2211/1014C09K2211/1011H10K85/633H10K85/631H10K85/615H10K50/11
Inventor 咸昊完安贤哲姜京敏金东骏朴旻洙闵丙哲文锺勋李萤振林东焕林大喆金昇好权桐热李成圭
Owner DONGJIN SEMICHEM CO LTD
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