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Benzophenanthroline derivatives and their applications

A technology of benzophenanthroline and derivatives is applied in the field of organic electroluminescence devices, which can solve the problem that the molecular energy gap and triplet energy level cannot be effectively improved, the host bipolar characteristics cannot be realized, and the lack of electron donating groups can be solved. and other problems, to achieve the effects of high carrier transport and luminous efficiency, high melting point and high luminous efficiency

Active Publication Date: 2021-04-30
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] U.S. patent application publications US2013 / 0099206A1 and US 2014 / 0151650 A1 reported fused heterocyclic aromatic hydrocarbon compounds containing phenanthroline. Among them, the molecular structure of the compound disclosed in US2013 / 0099206 A1 lacks an electron-donating group, and cannot realize the dual Polar characteristics; although the molecular structure of the compound disclosed in US2014 / 0151650 A1 contains some electron-donating groups, the electron-donating groups and electron-deficient groups are not directly connected, so the energy gap and triplet energy level of the molecule cannot be effectively improved , thus limiting the scope of application of such materials as host materials

Method used

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  • Benzophenanthroline derivatives and their applications
  • Benzophenanthroline derivatives and their applications
  • Benzophenanthroline derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0060] Synthetic Example 1. The preparation of intermediate M1, its synthetic route is as follows:

[0061]

[0062] 1,4-Diaminonaphthalene (20mmol, 3.16g) and triethylamine (60mmol, 6.06g) were mixed and dissolved in 50ml of dichloromethane, lowered to 0°C, and 3- Ethoxyacryloyl chloride (50mmol, 6.7g), after the dropwise addition, was slowly warmed up to room temperature and stirred, the reaction end 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=8:1, and the eluent was concentrated to obtain intermediate M1-A (6.44g, yield 91%).

[0063] Intermediate M1-A (17mmol, 6g) was dissolved in 60mL of dichloromethane, the mixture was lowered to 0°C, methanesulfonic acid (51mmol, 4.9g) was added dropwise with a constant pressure dropping funnel, and after the addition was completed, it was raised to...

Embodiment 3

[0071] Embodiment 3. The synthesis of compound A2, the synthetic route is as follows:

[0072]

[0073] Step 1: Synthesis of M2

[0074] Under nitrogen protection, add 2,4-dimethylaniline 2.67g (molecular weight 121,

[0075] 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%.

[0076] The second st...

Embodiment 4

[0078] Embodiment 4. The synthesis of compound A3, the synthetic route is as follows:

[0079]

[0080] Step 1: Synthesis of M3

[0081] The method is the same as the synthesis of M2 in Example 3, except that 2,4-dimethylaniline and 2,4-dimethylbromobenzene are replaced by 4-cyclohexylaniline and 4-cyclohexylbromobenzene respectively, and separated by column chromatography to obtain 5.5 g of white product, yield 83%.

[0082] The second step: the implementation process is the same as in Example 2, except that diphenylamine is replaced by intermediate M3 to synthesize the product.

[0083] Product MS (m / e): 892, elemental analysis (C62H68N4): theoretical value C: 86.05%, H: 7.67%, N: 6.27%; found value C: 86.00%, H: 7.63%, N: 6.37%.

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Abstract

The invention discloses a benzophenanthroline derivative and the application of the derivative in the technical field of preparing organic electroluminescence display and lighting. The invention also provides an organic electroluminescence device, which comprises The benzophenanthroline derivatives. Compared with the existing organic electroluminescent device, the organic electroluminescent device of the present invention has better luminous performance, can be driven at a lower voltage, has lower power consumption, and has a longer service life.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and the invention relates to a novel benzophenanthroline derivative and an organic electroluminescent device using the benzophenanthroline derivative. 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 cooperated to dope the phosphorescent material platinum octaethylporphyrin (PtOEP) in 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer of the electroluminescent device, so that the internal quantum efficiency and external quantum efficiency were improved 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....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04H01L51/54
CPCC07D471/04H10K85/631H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6574H10K85/6572
Inventor 孙恩涛高文正范洪涛任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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