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Spiro-structured organic electroluminescent composition and preparation method thereof

A spiro-ring structure and luminescent technology, applied in organic light-emitting devices, luminescent materials, organic chemistry, etc., can solve the problems of low purity of luminescent materials, difficult crystallization between molecules, slow luminous efficiency, etc., to achieve color purity, not easy to aggregate, Effect of Low Driving Voltage

Inactive Publication Date: 2018-04-20
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a spiro-ring structure organic electroluminescent composition and its preparation method to solve the problems of low purity and slow luminous efficiency of the luminescent material in the prior art, and has intermolecular Not easy to crystallize, not easy to aggregate, has the advantages of appropriate molecular weight, good film stability, suitable HOMO and LUMO energy levels, etc.

Method used

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  • Spiro-structured organic electroluminescent composition and preparation method thereof
  • Spiro-structured organic electroluminescent composition and preparation method thereof
  • Spiro-structured organic electroluminescent composition and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the preparation of compound 1:

[0054]

[0055] (1) Preparation of Intermediate I: In a 1L three-necked flask, add 9,9-dimethylacridine (41.9g, 0.20mol), o-bromoiodobenzene (62.2g, 0.22mol), sodium tert-butoxide ( 28.8g, 0.30mol), palladium acetate (0.45g, 2.0mmol), P(t-Bu) 3 HBF 4 (1.16g, 4mmol) and 500mL xylene, reacted at 120-130°C for 12h, after the reaction was over, 100g of water was added to the reaction system to quench the reaction, filtered, the filtrate was decompressed and desolvated, purified by column chromatography, and then purified by toluene, Petroleum ether was recrystallized to obtain Intermediate I with a yield of 82.37%;

[0056] (2) Preparation of intermediate II: Add the above-mentioned intermediate I (54.6g, 0.15mol) into a 1L three-necked flask, add 200g of tetrahydrofuran, cool down to -78°C, add dropwise a n-hexane solution of n-butyllithium (0.16 mol), the dropwise addition was completed, and the reaction was carried out...

Embodiment 2

[0059] Embodiment 2: the preparation of compound 2:

[0060]

[0061] Referring to Example 1, in the preparation process, the raw material 9,9-dimethylacridine was replaced with 9,9-diphenylacridine to obtain compound 2 with a yield of 45.47%.

[0062] High resolution mass spectrometry, molecular formula C 44 h 27 Br 2 N, theoretical value 727.0510, test value 727.0522.

Embodiment 3

[0063] Embodiment 3: the preparation of compound C01:

[0064]

[0065] In a 250ml three-necked flask, under nitrogen protection, compound 1 (6.03g, 0.01mol), phenylboronic acid (2.68g, 0.022mol), potassium carbonate (5.52g, 0.04mol), tetrakistriphenylphosphine palladium ( 232mg, 0.2mmol), 12mL water and 60mL toluene, reacted at 80-85°C for 10h, after the reaction was completed, filtered, the filtrate was desolvated under reduced pressure, purified by column chromatography, and then recrystallized by toluene and petroleum ether to obtain the target product C01. The rate is 83.28%.

[0066] High resolution mass spectrometry, molecular formula C 46 h 33 N, theoretical value 599.2613, test value 599.2627.

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Abstract

The invention discloses a spiro-structured organic electroluminescent composition and a preparation method thereof. The composition is not prone to crystallize among molecules, is not likely to aggregate, and has proper molecular weight, good film stability and suitable HOMO and LUMO energy levels. The composition can be used as a luminescent layer of an OLED device and can be applied to the fieldof organic electroluminescence. When the composition is used as a luminescent layer material of an OLED luminescent device, the manufactured OLED device is good in photoelectric property. The composition can be taken as a luminescent layer material and is applied to the field of organic electroluminescent device manufacture.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and in particular relates to a spiro-ring structure organic electroluminescence composition and a preparation method thereof. Background technique [0002] Organic electroluminescent diodes (OLEDs) were produced in the 1980s. They have many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which make them the most favorable competitors for the next generation of flat panel display technology. , has received great attention from people, and after more than 20 years of development, the technology has gradually matured. [0003] At present, organic electroluminescent technology is mainly used in two fields, namely full-color display and white lighting. Commodities based on OLED display technology have gradually realized industrialization, for example, in products such as smart phones and curved TVs. , this technique has been widely used. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D471/10H01L51/50H01L51/54
CPCC09K11/06C07D471/10C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092C09K2211/1059H10K85/626H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2102/00H10K2102/301
Inventor 高自良张成新巨成良慈振华冯鑫刘伟涛
Owner VALIANT CO LTD
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