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Terphenyl biphosphine three-coordination cuprous halide complex as well as 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 easy operation, high yield and simple synthesis method

Active Publication Date: 2018-11-06
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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  • Terphenyl biphosphine three-coordination cuprous halide complex as well as synthesis method and application
  • Terphenyl biphosphine three-coordination cuprous halide complex as well as synthesis method and application
  • Terphenyl biphosphine three-coordination cuprous halide complex as well as synthesis method and application

Examples

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 biphosphine three-coordination cuprous halide complex as well as a synthesis method and application and belongs to the technical field of light emitting materials.According to the complex, 1,2-dimethyl-4,5-dibromo-benzene is adopted as initial raw materials, a terphenyl bilithium reagent is synthesized through intermolecular coupling reactions, ligand dbdp issynthesized through a nucleophilic substitution reaction with diphenyl chlorphonium, dbdp is adopted as ligand to react with cuprous halide to synthesize a target product provided by the invention, and finally structures and light emission properties of the target product are represented. Results show that at a normal temperature, a solid terphenyl biphosphine three-coordination cuprous iodide complex emits green light, and a terphenyl biphosphine three-coordination cuprous bromide complex and a terphenyl biphosphine three-coordination cuprous chloride complex emit yellow and green light. Thesynthesis method is simple and easy to operate, in addition, the prepared target product has a microsecond-grade service life at the room temperature, and the result shows that the target product hasa light emission mechanism of thermal activity delayed fluorescence and has great potential of being used as an electroluminescent material applied to OLEDs (Organic Light Emitting Diodes).

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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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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