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Copper (1) compound with imidazole derivate as compounding body

A technology of imidazole derivatives and complexes, which is applied in the field of copper complexes, can solve problems such as time delay, and achieve the effect of easy synthesis and purification

Inactive Publication Date: 2007-07-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the migration of charges in the light-emitting layer takes a certain amount of time, there is a time delay effect.

Method used

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  • Copper (1) compound with imidazole derivate as compounding body
  • Copper (1) compound with imidazole derivate as compounding body
  • Copper (1) compound with imidazole derivate as compounding body

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1[Cu(Hpm)(POP)][BF 4 ] and the synthesis of Cu(pm)(POP)

[0062] 2-(2'-pyridyl)imidazole (Hpm) (145mg, 1.0mmol) was mixed with 2,2'-bis(diphenylphosphino)diphenyl ether (POP) (538mg, 1.0mmol) and [Cu( CH 3 EN) 4 ][BF 4 ] (314mg, 1.0mmol) were co-dissolved in 10mL of dichloromethane to obtain a light green transparent solution. After stirring at room temperature for 5 hours, an appropriate amount of methanol was added for recrystallization to obtain green needle-like crystals [Cu(Hpm)(POP)][BF 4 ] 810mg, yield 86%. 1HNMR (CDCl 3 , 300MHz): δ12.05(s, 1H), 8.28(d, 1H, J=8.1), 8.03(d, 1H), 7.90(t, 1H, J=7.11), 7.34-6.97(m, 29H) , 6.86 (m, 2H).

[0063] [Cu(Hpm)(pop)][BF 4 ] (275 mg, 0.33 mmol) was first dissolved in 5 mL of dichloromethane. Then, it was added to a solution of NaOH (0.53 g, 13.2 mmol) in 100 mL of methanol. After stirring for 10 hours, the solvent was drawn off to give a sticky mass. Extract with 5mL of dichloromethane, filter to obtai...

Embodiment 2

[0064] Embodiment 2 [Cu (Hpm) (PPh 3 ) 2 ][BF 4 ]Synthesis

[0065] 2-(2'-pyridyl) imidazole (Hpm) (145mg, 1.0mmol) and triphenylphosphine (PPh 3 ) (524mg, 2.0mmol) and [Cu(CH 3 EN) 4 ][BF 4 ] (314mg, 1.0mmol) were co-dissolved in 10mL of dichloromethane to obtain a light green transparent solution. After stirring at room temperature for 5 hours, an appropriate amount of methanol was added for recrystallization to obtain green granular crystals [Cu(Hpm)(PPh 3 ) 2 ][BF 4 ] 750mg, yield 76%. 1 HNMR (CDCl 3 , 300MHz): δ12.07(s, 1H), 8.24(d, 1H, J=8.10), 8.08(s, 1H), 7.89(t, 1H, J=7.50), 7.51(s, 1H), 7.41 -7.22 (m, 30H), 6.99 (s, 2H).

Embodiment 3

[0066] Embodiment 3 [Cu (Hpbm) (POP)] [BF 4 ] and the synthesis of Cu(pbm)(POP)

[0067] 2-(2'-pyridyl)benzimidazole (Hpbm) (195mg, 1.0mmol) was mixed with 2,2'-bis(diphenylphosphino)diphenyl ether (POP) (538mg, 1.0mmol) and four Tetrakis(acetonitrile)copper(I)[Cu(CH 3 EN) 4 ][BF 4 ] (314mg, 1.0mmol) were dissolved in 10mL of dichloromethane, and stirred to obtain a grass-green transparent solution. After stirring at room temperature for 1 hour, 10 mL of ether was added for recrystallization to obtain yellow-green needle crystals [Cu(Hpbm)(POP)][BF 4 ] 680mg, yield 77%. 1 HNMR (CDCl 3 , 300MHz): δ12.15(s, 1H), 8.47(d, 1H, J=8.9), 8.15(d, 1H, J=5.3), 7.90(t, 1H, J=8.9), 7.84(d, 1H, J=9.3Hz), 7.28-7.22(m, 7H), 7.12-7.04(m, 15H), 7.01-6.86(m, 10H).

[0068] [Cu(Hpbm)(POP)][BF 4 ] (295 mg, 0.3 mmol) was dissolved in 5 mL of dichloromethane and added to a solution of NaOH (530 mg, 13.2 mmol) in 100 mL of methanol. After stirring for 10 hours, the solvent was pumped dry. ...

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Abstract

The present invention relates to copper complex with imidazole as ligand. Ionic one-valent copper complex is prepared with pyridyl imidazole, pyridyl benzimidazole or quinolyl benzimidazole as the first ligand, triphenyl phosphine or bridged phenyl phosphine as the second ligand and one-valent copper ion. Neutral copper complex may be further obtained under the action of alkali. The ionic copper complex and the neutral copper complex may convert mutually under the action of acid and alkali. This kind of complex possesses strong room temperature phosphorescence emission and may be used as light emitting material.

Description

technical field [0001] The present invention relates to copper (I) complexes with imidazole derivatives as ligands. It belongs to the technical field of luminescent materials. technical background [0002] Organometallic complexes are an important class of organic electroluminescent materials. Compared with fluorescent complex materials, phosphorescent complexes based on heavy metals can make full use of all energy forms including singlet state (about 1 / 4) and triplet state (about 3 / 4) in organic electroluminescent devices. , the theoretical maximum internal quantum efficiency can reach 100%. In 1998, S.R. Forrest et al. first discovered that applying phosphorescent complexes to organic electroluminescence can greatly improve device efficiency (Nature, 1998, 395, 151-154.). Due to the huge advantages of phosphorescent materials in device efficiency, the research on their application has become one of the main directions in the field of organic electroluminescence. Common...

Claims

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Application Information

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IPC IPC(8): C07F1/08C09K11/06
Inventor 程延祥闵军辉孙伟谢志元王利祥苏光平
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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