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Double-ring metal platinum (II) coordination compound taking pyridazine derivative as ligand as well as preparation method and application of coordination compound

A technology of pyridazine derivatives and complexes, applied in the field of bicyclic metal platinum complexes and their preparation, can solve the problems of unsatisfactory luminescent properties of products, cumbersome synthetic routes, expensive raw materials, etc., to reduce the probability of redox and prevent molecular aggregation , cheap effect

Inactive Publication Date: 2019-04-26
ANHUI UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0010] Aiming at the problems that the existing preparation of bicyclic metal platinum (II) complexes requires expensive raw materials, cumbersome synthetic routes, poor repeatability and unsatisfactory luminescent properties of the product, the present invention provides a bicyclic metal platinum (II) complex with pyridazine derivatives as ligands II) Complexes and their preparation methods and applications. The preparation method of the present invention uses pyridazine derivatives as ligands to improve the reactivity of ligands and platinum, so that they can react with divalent platinum salts to generate pyridazines with a high yield in one step. Bicyclic Metal Platinum(II) Complexes

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  • Double-ring metal platinum (II) coordination compound taking pyridazine derivative as ligand as well as preparation method and application of coordination compound
  • Double-ring metal platinum (II) coordination compound taking pyridazine derivative as ligand as well as preparation method and application of coordination compound
  • Double-ring metal platinum (II) coordination compound taking pyridazine derivative as ligand as well as preparation method and application of coordination compound

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Experimental program
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Effect test

Embodiment 1

[0048] 2.3g (10mmol) 3,6-dichloro-4,5-cyclohexyl (1',4') pyridazine, 3.8g (20mmol) m-trifluoromethylbenzeneboronic acid and 1.4g (10mmol) potassium carbonate Add to a 250mL round bottom flask, add 0.2g (0.3mmol) PdCl 2 (dppf), then pour 30mL tetrahydrofuran and 15mL water, N 2 Protection, reflux at 100°C for 12h. Cool, spin dry THF, extract with dichloromethane to obtain the lower organic phase, spin dry, and use petroleum ether: ethyl acetate = 1:1 eluent silica gel column chromatography to obtain 4.1g 3,6-bis( Trifluoromethylphenyl)-4,5-cyclohex(1',4')pyridazine as a white solid in 91% yield. The NMR spectrum of the product is: 1 HNMR (400MHz, CDCl 3 )δ8.00(s, 2H), 7.92(d, J=7.6Hz, 2H), 7.82(d, J=7.8Hz, 2H), 7.72(t, J=7.7Hz, 2H), 3.43(s, 2H), 1.98 (d, J = 7.9 Hz, 4H), 1.52 (d, J = 7.5 Hz, 4H). 19 F NMR (CDCl 3 , 367MHz) δ-62.86 (s, 6F). The mass spectrum of product is: MS ((+)-ESI): m / z=449.67 (calcd.449.14forC 24 h 19 f 6 N 2 , [M+H + ]).

[0049] 1.8g (4mmol)...

Embodiment 2

[0052] Add 10g (68mmol) of 3,6-dichloropyridazine, 12.8g (68mmol) of m-trifluoromethylbenzeneboronic acid and 9.38g (68mmol) of potassium carbonate into a 500mL round bottom flask, and add [1,1 ， -bis(diphenylphosphino)ferrocene]palladium dichloride (PdCl 2 (dppf)) 1.1g (1.6mmol), then pour 45mL tetrahydrofuran and 30mL water, N 2 Protection, reflux for 12h. Cooled, spin-dried THF, extracted with dichloromethane solution, spin-dried the organic phase, and separated by silica gel column chromatography with petroleum ether:ethyl acetate=3:1 eluent to obtain 10.2g 3-(3-trifluoromethyl Phenyl)-6-chloropyridazine as a white solid, yield 58%. The NMR and MS data of the product are: 1 H NMR (400MHz, CDCl 3 )δ8.31(s, 1H), 8.26(d, J=7.8Hz, 1H), 7.88(d, J=9.0Hz, 1H), 7.78(d, J=7.8Hz, 1H), 7.67(t, J=7.8Hz, 1H), 7.62(d, J=9.0Hz, 1H); 19 F NMR (376MHz, CDCl 3 )δ-62.66 (s, 3F).MS ((+)-ESI): m / z=259.02 (calcd.259.03forC 11 h 7 CIF 3 N 2 , [M+H + ]).

[0053] Add 5 g (19 mmol) 3-...

Embodiment 3

[0057] 3-(3-trifluoromethylphenyl)-6-chloropyridazine 1.3g (5mmol), 2,4,6-trimethylphenol 0.8g (6mmol) were placed in a 120mL reaction flask, and the reaction Add potassium carbonate 1.4g (10mmol) in the bottle, with N,N-dimethylformamide 50mL as solvent, pass into N 2 Sealing protection, the reaction was refluxed for 12 hours, the reaction was completed and cooled to room temperature, the organic phase was extracted with ethyl acetate, and the organic phase was back-extracted with water, and the organic phase was spin-dried with petroleum ether and ethyl acetate at a ratio of 5:1. After separation by column chromatography, 1.4 g of white solid 3-(3-trifluoromethyl)-6-(2,4,6-trimethylphenoxy)pyridazine was obtained with a yield of 76%. The NMR and MS data of the product are: 1 H NMR (400MHz, CDCl 3 )δ8.34(s, 1H), 8.23(d, J=8Hz, 1H), 7.93(d, J=9.2Hz, 1H), 7.72(d, J=8.0Hz, 1H), 7.63(t, J =8.0Hz, 1H), 7.27(t, J=6.0Hz, 1H), 7.27(s, 2H), 2.32(s, 3H), 2.15(s, 6H); 19 F NMR (376M...

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Abstract

The invention discloses a double-ring metal platinum (II) coordination compound taking a pyridazine derivative as ligand as well as a preparation method and application of the coordination compound, and belongs to the technical field of organic photoelectric materials. The preparation method of the double-ring metal platinum (II) coordination compound taking the pyridazine derivative as the ligandcomprises the following steps: synthesizing pyridazine ligand and mixing the pyridazine ligand with a bivalent platinum salt and a solvent to generate the double-ring metal platinum (II) coordinationcompound taking the pyridazine derivative as the ligand. The ligand has high reaction activity with platinum and can react with the bivalent platinum salt to generate the high-yield pyridazine double-ring metal platinum (II) coordination compound through one step. The generated pyridazine double-ring metal platinum (II) coordination compound has the advantages of high stability and high luminescent quantum efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a bicyclic metal platinum (II) complex with pyridazine derivatives as ligands, a preparation method and application thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have self-illumination, no need for backlight, high contrast, thin thickness, wide viewing angle, fast response, can be used for flexible panels, wide operating temperature range, simple structure and manufacturing process, etc. Excellent characteristics, is considered to be the emerging technology of the next generation of flat panel displays. From the perspective of organic light-emitting materials used in OLEDs, the internal quantum efficiency of the electroluminescent device can theoretically reach 100% due to the heavy atom effect of phosphorescent metal complexes, and in these phosphorescent complexes, the ring metal platinum (II) The complex is on...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K50/11
Inventor 童碧海梅群波张千峰陈熳王月
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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