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Novel compound and organic electroluminescent device including the same

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

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

[0139] The synthesis of preparation example 1.IM

[0140]

[0141] In order to synthesize the target compound, the synthesis is carried out through the above-mentioned steps to prepare IM.

[0142] The synthesis method of the following IM1 is as follows.

[0143]

[0144] In a round bottom flask, 48.5 g of [1,1':3',1"-tetraphenyl]-5'-ylboronic acid, 50.0 g of 1-bromo-4-iodobenzene were dissolved in 1000 ml of 1, 4-dioxane, and put into 265ml of K 2 CO 3 (2M) and 6.1g of Pd(PPh 3 ) 4 Thereafter, the mixture 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), filtered under reduced pressure, and recrystallized to obtain 50.4 g (yield 74%) of intermediate IM1.

[0145] The following IM2 to IM9 were synthesized by changing the starting materials in the same manner as above IM1.

[0146]

[0147]

preparation example 2

[0148] Synthesis of Preparation Example 2.OP

[0149] The following synthesis method of OP1 is as follows.

[0150]

[0151] 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, 2.0 g of Pd 2 (dba)3 , 2.5ml of (t-Bu) 3 After P was dissolved in 200 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), filtered under reduced pressure, and then recrystallized to obtain 11.75 g (yield 75%) of OP1.

[0152] The following OP2 to OP12 were synthesized by changing the starting materials in the same manner as above OP1.

[0153]

[0154]

Synthetic example 1

[0155] Synthesis Example 1. Synthesis of Compound 1

[0156]

[0157] In a round bottom flask, 3.0 g of IM1, 2.8 g of OP2, 1.1 g of t-BuONa, 0.3 g of Pd 2 (dba) 3 , 0.3ml of (t-Bu) 3 After P was dissolved in 90 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 3.37 g (yield 65%) of Compound 1.

[0158] m / z: 665.31 (100.0%), 666.31 (56.0%), 667.31 (15.1%), 668.32 (2.7%)

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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 compounds and organic light-emitting 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 incr...

Claims

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Application Information

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IPC IPC(8): C07C211/61C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/61C09K2211/1011C09K2211/1014C09K2211/1007H10K85/615H10K85/633H10K50/12H10K50/17H10K50/15
Inventor 咸昊完安贤哲姜京敏金东骏闵丙哲文锺勋徐净雅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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