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Copper (I) coordination compound and application thereof

A technology of complexes and ligands, applied in copper organic compounds, compounds of Group 5/15 elements of the periodic table, electrical components, etc., can solve problems affecting the stability of electroluminescent devices, etc.

Active Publication Date: 2013-02-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Chinese patent document with application number 200610130886.7 discloses a copper (I) complex with imidazole derivatives as ligands. The copper (I) complex uses imidazole derivatives as ligands and simultaneously forms ionic copper (I) complexes. Compounds and neutral copper (I) complexes, and the neutral imidazole derived copper (I) complexes reported in the literature are easily transformed into ionic copper (I) complexes with their surrounding environment, thereby affecting electroluminescent devices stability

Method used

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  • Copper (I) coordination compound and application thereof
  • Copper (I) coordination compound and application thereof
  • Copper (I) coordination compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Under argon, add 1.0mmol 2,2'-pyridylindole, 0.12g NaH 0.12g and 10ml tetrahydrofuran in reaction flask A;

[0085] Under argon, add 1.0mmol CuI, 2.0mmol PPh to reaction bottle B 3 and 10ml tetrahydrofuran, stirred at room temperature for 2h;

[0086] Filter the solution in reaction flask A, add the clear liquid obtained by filtration into reaction flask B, drain the solvent after stirring at room temperature for 2 h, extract the residue with 10 ml of dichloromethane, transfer the obtained clear liquid to reaction flask C, and 10ml methyl alcohol is added on the described dichloromethane solution layer, obtains copper (I) complex crystal 0.65g by liquid-liquid diffusion method, is called for short [Cu (pi) (PPh 3 ) 2 ], the yield is 84%, the structural formula is shown in formula IV, and the crystal structure diagram is as follows figure 1 shown. The copper (I) complex prepared in this example was detected by a 600MHz nuclear magnetic resonance spectrometer, and the...

Embodiment 2

[0088] Under argon, add 1.0mmol 2,2'-pyridylindole, 0.12NaH and 10ml THF in reaction flask A;

[0089] Under the condition of argon, add 1.0mmol CuI, 1.0mmol POP and 10ml tetrahydrofuran to reaction flask B, and stir at room temperature for 2h;

[0090] Filter the solution in reaction flask A, add the clear liquid obtained by filtration into reaction flask B, drain the solvent after stirring at room temperature for 2 h, extract the residue with 10 ml of dichloromethane, transfer the obtained clear liquid to another reaction flask C, Carefully add 10ml of methanol to the dichloromethane solution layer, and obtain 0.57g of copper (I) complex crystals by liquid-liquid diffusion method, referred to as [Cu(pi)(POP)], the yield is 72%, and the structural formula is as follows: V is shown. The copper (I) complex prepared in this example was detected by a 600MHz nuclear magnetic resonance spectrometer, and the result was: Mp: 210°C; 1 H NMR (600MHz, CDCl 3 )δ6.57(t, J=7.5Hz, 1H), 6...

Embodiment 3

[0093] Under argon atmosphere, add 1.0mmol 2,2'-quinolinolindole, 0.12g NaH and 10ml tetrahydrofuran in reaction flask A;

[0094] Under argon, add 1.0mmol CuI, 2.0mmol PPh to reaction bottle B 3 and 10ml tetrahydrofuran, stirred at room temperature for 2h;

[0095] Filter the solution in reaction bottle A, add the filtered clear liquid into reaction bottle B, stir at room temperature for 2 hours, then drain the solvent, extract the residue with 10ml of dichloromethane, transfer the clear liquid to reaction bottle C, add 10ml of methanol to On the dichloromethane solution layer, obtain copper (I) complex crystal 0.68g by liquid-liquid diffusion method, be called for short [Cu (qi) (PPh 3 ) 2 ], the yield is 81%, and the structural formula is as shown in formula VI. The copper (I) complex prepared in this example was detected by a 600MHz nuclear magnetic resonance spectrometer, and the result was: Mp: 157°C; 1 HNMR (600MHz, CDCl 3 )δ6.81(m, 2H), 6.98(m, 2H), 7.10-7.17(m, 1...

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Abstract

The invention provides a copper (I) coordination compound. The copper (I) coordination compound has the structure as shown in formula I, wherein the indole derivative ligand is shown in the specification, two individual aryl phosphine ligands or bridging aryl phosphine bidentate ligands are also shown in the specification, and each phosphorus atom of the aryl phosphine ligands at least has one aryl substituent, and the other substituent is one of the aryl and C1-C30 alkyls. The copper (I) coordination compound provided by the invention is the neutral copper (I) coordination compound. Compared with the ionized coordination compound, the neutral copper (I) coordination compound can be used to overcome the time delay effect of the luminescent device caused by the ionic migration resistance due to the fact that the neutral copper (I) coordination compound has no other coordination atoms. In addition, due to the absence of other coordination atoms in the copper (I) coordination compound, the neutral copper (I) coordination compound of the indole derivatives has small possibility of reacting with the surrounding environment to be converted into the ionized copper (I) coordination compound, therefore the copper (I) coordination compound provided by the invention can be used in organic electroluminescent devices and sensors.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a copper (I) complex and its application. Background technique [0002] Organic electroluminescence is a phenomenon in which organic materials are excited by electrical energy to emit light. In 1998, S.R. Forrest et al. first discovered that the application of phosphorescent complexes to organic electroluminescent materials can greatly improve the efficiency of devices. Due to the great advantages of organic electroluminescent materials with phosphorescent complexes in devices, the research on them has become one of the main directions in the field of organic electroluminescence. Moreover, since the heavy metal-based phosphorescent complex can fully utilize all energy forms including singlet and triplet states, its maximum internal quantum efficiency is high, so organic electroluminescent materials have high electroluminescence efficiency. [0003] Among various ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C07F1/08C07F9/6558C07F9/50C09K11/06H01L51/54
Inventor 程延祥刘晓辉孙伟李晓谢志元王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI