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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 organic light-emitting devices and novel arylamine compounds, can solve the problems of high driving voltage, short life, low efficiency, etc., achieve long-life devices, prevent recrystallization, and high efficiency Effect

Pending Publication Date: 2019-01-15
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

[0128] The synthesis of preparation example 1.IM

[0129]

[0130] In order to synthesize the target compound, the preparation of the IM is synthesized by any one of the above-mentioned steps, and may not be limited thereto.

[0131] The synthesis method of the following IM1 is as follows.

[0132]

[0133] In a round bottom flask, dissolve 27.6 g of [1,1'-biphenyl]-4-ylboronic acid, 50.0 g of 4-bromo-4'-iodo-1,1'-biphenyl in 800 ml of 1, After 4-dioxane, 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 after adding water, the reaction was terminated. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and recrystallized to obtain 50.4 g (yield 74%) of intermediate IM1.

[0134] By the same method as above IM1, using different starting materials, the following IM2 to IM13 were synthesized.

[0135]

[0136]

[0137]

preparation example 2

[0138] Synthesis of Preparation Example 2.OP

[0139] The following synthesis method of OP1 is as follows.

[0140]

[0141] In a round bottom flask, 15.0 g of the above 2-bromo-9,9-dimethyl-9H-fluorene, 5.6 g of aniline, 7.9 g of t-BuONa, Pd 2 (dba) 3 2.0g, (t-Bu) 3 After dissolving 2.5ml of P in 200ml of toluene, reflux and stir. The reaction was confirmed by thin layer chromatography (TLC), and after adding water, the reaction was terminated. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then recrystallized to obtain 11.75 g (yield 75%) of OP1.

[0142] By the same method as above OP1, using different starting materials, the following OP2 to OP3 were synthesized.

[0143]

[0144]

Synthetic example 1

[0145] Synthesis Example 1. Synthesis of Compound 1

[0146]

[0147] In a round bottom flask, 5.0 g of IM 1, 3.7 g of OP1, 1.9 g of t-BuONa, Pd 2 (dba) 3 0.5g, (t-Bu) 3 After dissolving 0.5 ml of P in 130 ml of toluene, it was stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC), and after adding water, the reaction was terminated. The organic layer was extracted with methylcellulose (MC), and filtered under reduced pressure, followed by column purification and recrystallization to obtain 5.36 g (yield 70%) of Compound 1.

[0148] 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 prime) or a hole injection layer (HIL), hole injection andtransport properties can be increased, and high efficiency and long life 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/60H01L51/54
CPCC07C211/60C07C2603/18H10K85/615H10K85/626H10K85/633C07C211/61H10K50/156
Inventor 咸昊完安贤哲姜京敏金熙宙金东骏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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