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A kind of quinoline derivatives and application thereof

A technology of quinolines and derivatives, applied in the field of organic electroluminescence, which can solve problems such as easy crystallization or agglomeration, lower device efficiency, and lower device life, and achieve high triplet state, wide energy gap, and improved performance.

Active Publication Date: 2022-02-22
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Materials with low Tg temperature have poor thermal stability and are easy to crystallize or agglomerate, which will greatly reduce the life of the device and seriously reduce the efficiency of the device

Method used

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  • A kind of quinoline derivatives and application thereof
  • A kind of quinoline derivatives and application thereof
  • A kind of quinoline derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1. Intermediate M1 The preparation example of

[0045] Its synthetic route is as follows:

[0046]

[0047] 2,7 Diaminonaphthalene (20mmol, 3.16g) and triethylamine (60mmol, 6.06g) were mixed and dissolved in 50ml of dichloromethane, lowered to 0°C, and 3-ethanediol was added dropwise with a constant pressure dropping funnel under stirring. After the dropwise addition of oxyacryloyl chloride (50 mmol, 6.7 g), the temperature was slowly raised to room temperature and stirred. The end point of the reaction was monitored by TLC, and the reaction was completed in 5 hours. Quenched with water, extracted with dichloromethane, the extract was concentrated, passed through a silica gel column, the eluent was petroleum ether:dichloromethane=9:1, and the eluent was concentrated to obtain intermediate M1-A (6.01g, yield 85%).

[0048] Intermediate M1-A (17mmol, 6g) was dissolved in 60mL of dichloromethane, the mixture was lowered to 0°C, methanesulfonic acid (51mmol,...

Embodiment 2

[0051] Embodiment 2. The synthesis of compound A1, the synthetic route is as follows:

[0052]

[0053] Under nitrogen protection, add 3.38g of diphenylamine (molecular weight 169, 20mmol) and 40ml of anhydrous toluene into a 100ml three-necked reaction flask, cool to -78°C, and slowly add 8.8ml of n-BuLi (2.4M, 21mmol) . After dropping, the reaction was stirred for 30 minutes, and the temperature naturally rose to -30°C. Add intermediate M12.83g (molecular weight 298, 9.5mmol), Pd2(dba)3 174mg (molecular weight 916, 0.19mmol), P(tBu)3 55mg (molecular weight 202, 0.27mmol) under nitrogen flow. After the addition was completed, the oil bath was slowly heated to reflux for reaction, and the end point of the reaction was monitored by TLC, and the reaction was completed in 8 hours. Cool, add water to quench the reaction, extract with 50ml of dichloromethane, the organic phase is dried with anhydrous MgSO4, the organic phase is evaporated to dryness, and the obtained solid is ...

Embodiment 3

[0055] Embodiment 3. The synthesis of compound A2, the synthetic route is as follows:

[0056]

[0057] Step 1: Synthesis of M2

[0058] Under nitrogen protection, add 2,4-dimethylaniline 2.67g (molecular weight 121,

[0059] 22mmol), 2,4-dimethylbromobenzene 3.68g (molecular weight 184, 20mmol), sodium tert-butoxide 5.76g (molecular weight 96, 60mmol), Pd2(dba) 3 183mg (molecular weight 916, 0.2mmol), P( tBu)3 121 mg (molecular weight 202, 0.6 mmol). Anhydrous toluene 50ml. After the addition was completed, the oil bath was slowly heated to reflux for reaction, and the end point of the reaction was monitored by TLC, and the reaction was completed in 10 hours. Cool, add water to quench the reaction, extract with 50ml of dichloromethane, the organic phase is dried with anhydrous MgSO4, the organic phase is evaporated to dryness, and the obtained solid is separated by column chromatography to obtain 3.8g white solid, molecular weight 225, yield 85%.

[0060] The second st...

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Abstract

A quinoline derivative and its application and organic electroluminescence device, the quinoline derivative has a structure as shown in the general formula (1): the quinoline derivative provided by the invention is used in organic In the electromechanical luminescent device, the driving voltage can be reduced, the current efficiency can be improved, and the device life can be improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to a quinoline derivative, its application and an organic electroluminescence device. Background technique [0002] In 1998, Professor Ma Yuguang of Jilin University doped poly-N-vinylcarbazole (PVK) with an osmium complex [Os(CN) 2 (PPh 3 ) 2 bpy] prepared an electrophosphorescent device (Synthetic Metals, 1998, 94:245-248). In the same year, Thomson and Forrest collaborated to dope the phosphorescent material platinum octaethylporphyrin (PtOEP) on 8-hydroxyquinoline aluminum (Alq 3 ) as the light-emitting layer of the electroluminescent device, the internal quantum efficiency and external quantum efficiency are increased to 23%, 4% (Nature, 1998,395:151-154; Appl.Phys.Lett.,1999,75:4 -6). Since then, organic light-emitting devices based on phosphorescent metal complexes have developed rapidly. Different from traditional organic small molecules and conjugated polyme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1088C09K2211/1092C09K2211/1029H10K85/6574H10K85/6576H10K85/6572
Inventor 孙恩涛张向慧范洪涛高文正
Owner BEIJING ETERNAL MATERIAL TECH
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