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Terbiphenyl bisphosphine tricoordinate cuprous halide complex and its synthesis method and application

A technology of terphenylbisphosphine and cuprous halide, applied in the field of terphenylbisphosphine tricoordinated cuprous halide complex and its synthesis, achieving the effects of high yield, easy operation and simple synthesis method

Active Publication Date: 2020-07-21
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, there are few reports on tricoordinate copper(I) complexes

Method used

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  • Terbiphenyl bisphosphine tricoordinate cuprous halide complex and its synthesis method and application
  • Terbiphenyl bisphosphine tricoordinate cuprous halide complex and its synthesis method and application
  • Terbiphenyl bisphosphine tricoordinate cuprous halide complex and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The 4,4',4",5,5',5"-hexamethyl-(1,1':2',1"-terphenyl)-2,2"-bis(diphenyl The synthetic method of base phosphine) ligand (dbdp), comprises the steps:

[0042] A three-necked flask containing 1,2-dimethyl-4,5-dibromobenzene (1 g, 3.81 mmol) was added 20 mL THF under vacuum, the temperature was lowered to -78 °C, and 2.02 mL normal Butyllithium n-hexane solution (2.5mol / L, 5.06mmol), keep the temperature at -78°C, stir for 1h, add diphenylphosphine chloride (0.56g, 2.53mmol), continue stirring for 2h, then warm to room temperature , after stirring for 12 hours, add 15 mL of water to quench the reaction, extract with dichloromethane to obtain the organic phase, dry and evaporate the organic solvent to obtain a yellow oily liquid, and then use petroleum ether:dichloromethane=4:1 (volume ratio) as the developer 0.55 g of a white solid product was obtained by column chromatography separation, and the yield was 30.5%.

[0043] IR(KBr,ν / cm -1 ) test results are as follows: 307...

Embodiment 2

[0047] The terphenyl bisphosphine tricoordinate cuprous iodide complex (complex 1) of the present embodiment is prepared by the following method, including the following steps:

[0048] Add dbdp (143mg, 0.21mmol) and cuprous iodide (0.21mmol) synthesized in Example 1 into 20mL of dichloromethane, react for 5h, filter, suspend and dry the solvent under reduced pressure to obtain a light yellow-green solid. Then the light yellow-green solid was dissolved in a mixed solvent of 10 mL of dichloromethane / ethanol (V:V=3:1), and a colorless crystal was finally obtained by solvent evaporation at room temperature, that is, the complex 1. The yield 80%.

[0049] The relevant test data of the complex 1 synthesized above are as follows:

[0050] 1 H NMR (600MHz, CDCl 3 ) test results are as follows: δ: 7.96~7.91(m,4H), 7.45~7.42(m, 6H), 7.24~7.20(m,2H), 7.11~7.05(m,6H), 6.94~6.92(m,2H ),6.84~6.79(m,4H), 6.41(s,2H),2.21(s,6H),2.15(s,6H),2.00(s,6H).

[0051] 31 P NMR (240M, CDCl 3 ) t...

Embodiment 3

[0053] The terphenyl bisphosphine tricoordinate cuprous bromide complex (complex 2) of the present embodiment is prepared by the following method, including the following steps:

[0054] The dbdp (143 mg, 0.21 mmol) synthesized in Example 1 and cuprous bromide (0.21 mmol) were added to 20 mL of dichloromethane, reacted for 5 h, filtered, and the solvent was suspended under reduced pressure to obtain a pale yellow-green solid. Then the light yellow-green solid was dissolved in a mixed solvent of 10 mL of dichloromethane / ethanol (V:V=3:1), and a colorless crystal was finally obtained by solvent evaporation at room temperature, that is, the complex 2. The yield For: 78%, the relevant test data of the complex 2 are as follows:

[0055] 1 H NMR (600MHz, CDCl 3 ) test results are as follows: δ: 7.94(s,4H), 7.44~7.40(m,6H), 7.22~7.20(m,2H), 7.09~7.04(m,6H), 6.93~6.90(m,2H), 6.78~6.75(m,4H),6.48~6.47(m,2H),2.21(s,6H),2.15(s,6H),2.00(s,6H).

[0056] 31 P NMR (240M, CDCl 3 ) test ...

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Abstract

The invention relates to a terphenyl bisphosphine tricoordinate cuprous halide complex, a synthesis method and an application thereof, and belongs to the technical field of luminescent materials. The present invention uses 1,2 dimethyl-4,5-dibromobenzene as a starting material to synthesize a terphenyl dilithium reagent through an intermolecular coupling reaction, and then reacts with diphenylphosphine chloride to generate a nucleophilic substitution reaction to synthesize a compound body dbdp, and then use dbdp as a ligand to react with cuprous halide to synthesize the target product of the present invention, and finally characterize the structure and luminescent properties of the target product. The results show that at room temperature, the solid-state terphenylbisphosphine tricoordinated cuprous iodide complex emits green light, and the terphenylbisphosphine tricoordinated cuprous bromide complex and terphenylbisphosphine tricoordinated cuprous chloride The complex emits yellow-green light. The synthesis method of the present invention is simple and easy to operate, and the obtained target product has microsecond-level luminescence lifetime at room temperature, indicating that the luminescence mechanism of the target product is thermally active delayed fluorescence, and has great potential as an electroluminescent material applied to OLEDs.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, more specifically, the invention relates to a terphenyl bisphosphine tricoordinate cuprous halide complex, a synthesis method and an application. Background technique [0002] Controlling the structure and configuration of copper(I) complexes by selecting rigid ligands and groups with steric hindrance is the key to the synthesis of highly efficient luminescent copper(I) complexes. When the P atom in the bisphosphine ligand is connected to the aromatic ring, the compound shows good coordination ability and can form a stable complex with Cu(I). Studies have shown that when the ligand has a large steric hindrance, it will form a three-coordinate planar rigid Cu(I) complex, which can effectively inhibit the non-radiative decay process caused by the "Jahn-Teller distortion" in the excited state, and greatly improve the luminescence efficiency. In 2011, Japanese chemist Osawa et al. rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6596C09K11/06H01L51/54
CPCC09K11/06C07F9/6596C07B2200/13C09K2211/188H10K85/371
Inventor 柳利刘立平
Owner HUBEI UNIV
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