Benzophenanthroline derivative and application thereof

A technology of benzophenanthroline and derivatives, which is applied in the field of organic electroluminescence, can solve the problems of reducing device efficiency, easy crystallization or agglomeration, shortening device life, etc., achieves wide energy gap, improves triplet energy level, The effect of improving performance

Inactive Publication Date: 2019-01-04
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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  • Benzophenanthroline derivative and application thereof
  • Benzophenanthroline derivative and application thereof
  • Benzophenanthroline derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0057] Synthesis Example 1. Preparation of intermediate M1, the synthesis route is as follows:

[0058]

[0059] 2,3-Diaminonaphthalene (20mmol, 3.16g), methyl acrylate (60mmol, 5.16g), AlCl3 (60mmol, 7.92g) were mixed and dissolved in 50ml of xylene, slowly heated to reflux and stirred, TLC monitored the end of the reaction , The reaction is completed in 5 hours. Quench with water, extract with toluene, concentrate the extract, and pass through a silica gel column. The eluent is petroleum ether: ethyl acetate=5:1. The eluent is concentrated to obtain intermediate M1-A (4.0g, yield 60%) ).

[0060] Intermediate M1-A (12mmol, 4.0g) was dissolved in 40mL of PPA, heated under reflux and stirred for reaction, and the end of the reaction was monitored by TLC. The reaction was completed in 2 hours. The reaction solution was added to water for quenching, extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and spin-dried under reduced pressure to obtain an oily...

Embodiment 6

[0083] Example 6. Synthesis of compound A2, the synthetic route is as follows:

[0084]

[0085] Step 1: Synthesis of M5

[0086] Under the protection of nitrogen, add 2.67g of 2,4-dimethylaniline (molecular weight 121,

[0087] 22mmol), 2,4-dimethyl bromobenzene 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, the oil bath was slowly heated to reflux for the reaction, and the end of the reaction was monitored by TLC. The reaction was completed in 10 hours. Cool, add water to quench the reaction, extract with 50 ml of dichloromethane, dry the organic phase with anhydrous MgSO4, evaporate the organic phase to dryness, and separate the obtained solid by column chromatography to obtain 3.8 g of white solid with a molecular weight of 225 and a yield of 85%.

[0088] The second step: the implementat...

Embodiment 7

[0090] Example 7. Synthesis of compound A3, the synthetic route is as follows:

[0091]

[0092] Step 1: Synthesis of M6

[0093] The method is the same as the synthesis of M5 in Example 6, except that 2,4-dimethylaniline and 2,4-dimethylbromobenzene are replaced with 4-cyclohexylaniline and 4-cyclohexylbromobenzene respectively, and the results are separated by column chromatography. The white product was 5.5 g, and the yield was 83%.

[0094] The second step: the implementation process is the same as that in Example 5, except that diphenylamine is replaced with intermediate M6 to synthesize the product.

[0095] Product MS (m / e): 892, elemental analysis (C62H68N4): theoretical C: 86.05%, H: 7.67%, N: 6.27%; measured value C: 86.00%, H: 7.63%, N: 6.37%.

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Abstract

The invention discloses a kind of benzophenanthroline derivative and application thereof in preparation in the field of organic electroluminescent display and illumination technology. The invention also provides an organic electroluminescent device, which comprises the benzophenanthroline derivative. Compared with an existing organic electroluminescent device, the organic electroluminescent deviceof the invention has better luminous performance, can be driven by a lower voltage, and has lower power consumption and longer service life.

Description

Technical field [0001] The present invention belongs to the field of organic electroluminescence, and specifically relates to a benzophenanthroline derivative and an organic electroluminescence device using the benzophenanthroline derivative. Background technique [0002] In 1998, Professor Ma Yuguang of Jilin University doped poly-N-vinylcarbazole (PVK) with osmium complex [Os(CN) 2 (PPh 3 ) 2 bpy] An electro-phosphorescent device was prepared (Synthetic Metals, 1998, 94:245-248). In the same year, Thomson and Forrest collaborated to dope the phosphorescent material octaethylporphyrin platinum (PtOEP) into 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer of the electroluminescent device to increase the internal quantum efficiency and external quantum efficiency respectively 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. Unlike tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1088C09K2211/1029H10K85/615H10K85/633H10K85/636H10K85/6574H10K85/6572
Inventor 孙恩涛张向慧范洪涛高文正
Owner BEIJING ETERNAL MATERIAL TECH
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