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A tetradentate ring metal platinum (ii) and palladium (ii) complex luminescent material containing quinoline structural unit and its application

A structural unit, metal platinum technology, applied in the fields of light-emitting materials, organic chemistry, electrical components, etc., can solve the problems of reduced chemical stability and thermal stability of complexes, low phosphorescence quantum efficiency, vibration, etc., to improve chemical stability. and thermal stability, inhibition of non-radiative transitions, and the effect of broad application prospects

Active Publication Date: 2022-07-26
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Cyclic metal platinum(II) complexes based on bidentate ligands have low molecular rigidity, and the two bidentate ligands are easy to distort and vibrate, resulting in non-radiative attenuation, resulting in low phosphorescence quantum efficiency; and ring metals based on tridentate ligands. The metal platinum (II) complex molecule needs a second coordination anion (such as alkyne anion, Cl-, carbene, etc.), which will also lead to a decrease in the chemical and thermal stability of the complex; the above reasons are not conducive to its use as a phosphorescent material Application in OLED devices

Method used

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  • A tetradentate ring metal platinum (ii) and palladium (ii) complex luminescent material containing quinoline structural unit and its application
  • A tetradentate ring metal platinum (ii) and palladium (ii) complex luminescent material containing quinoline structural unit and its application
  • A tetradentate ring metal platinum (ii) and palladium (ii) complex luminescent material containing quinoline structural unit and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115] Example 1: The platinum complex Pt1 can be synthesized as follows:

[0116]

[0117] Synthesis of the intermediate 8-methoxyquinoline: To a 100-mL there-necked flask with a magnetic rotor, add 8-hydroxyquinoline (5.00 g, 34.5 mmol, 1.00 equiv), N,N-dimethylformaldehyde amide (40 ml), then placed in a low-temperature bath and stirred, slowly adding 60% sodium hydrogen (1.38 g, 34.5 mmol, 1.00 equiv) by mass fraction after the temperature was lowered, adding iodomethane ( 5.14 g, 36.3 mmol, 1.05 equiv), reacted for 8h. The reaction mixture was quenched by adding ethanol, the solvent was distilled off under reduced pressure, extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and the obtained crude product was separated and purified by silica gel column chromatography, eluent (petroleum ether) / acetone) = 2:1, and the solvent was distilled off under reduced pressure to obtain 4.76 g of a black-red solid with ...

Embodiment 2

[0123] Example 2: The platinum complex Pt2 can be synthesized as follows:

[0124]

[0125] Synthesis of L2-Me: 2-bromo-8-methoxyquinoline (234 mg, 0.99 mmol, 1.05 equiv), B (400 mg, 0.94 mmol) were added to a 50 mL three-necked flask with a magnetic rotor. , 1.00 equiv.) Pd (PPh 3 ) 4 (32.5 mg, 0.03 mmol, 0.03 equiv), K 2 CO 3 (324 mg, 2.34 mmol, 2.50 equiv), after three nitrogen purges, dioxane / H was added by injection 2 O=6:1 ml, the temperature was increased to 85°C, and the reaction was carried out for 24 hours. The reaction mixture was quenched by adding water, diluted by adding ethyl acetate, extracted three times with ethyl acetate and then dried by adding anhydrous sodium sulfate. The obtained crude product was separated and purified by silica gel column chromatography, eluent (petroleum ether / ethyl acetate=6: 1), the solvent was distilled off under reduced pressure to obtain 333 mg of a white foamy solid with a yield of 78%. 1 HNMR (500MHz, CDCl 3 ):δ1.70(s...

Embodiment 3

[0128] Example 3: The platinum complex Pt3 can be synthesized as follows:

[0129]

[0130] Synthesis of 5-bromo-8-methoxyquinoline: add 8-methoxyquinoline (4.76 g, 29.9 mmol, 1.00 equiv) to a 500-ml three-necked flask with a magnetic rotor, add 230 ml of acetonitrile, After that, N-bromosuccinimide (5.32 g, 31.3 mmol, 1.05 equiv) was slowly added, and the reaction was carried out for 8 hours. The reaction mixture was quenched by adding aqueous sodium sulfite solution, diluted by adding dichloromethane, extracted three times with dichloromethane, and the organic phases were combined and dried by adding anhydrous sodium sulfate. The crude product was separated and purified by silica gel column chromatography, and the solvent was distilled off under reduced pressure with the eluent (dichloromethane / ethyl acetate=10:1) to obtain 5.8 g of a pale yellow solid with a yield of 82%. used directly in the next reaction.

[0131] Synthesis of intermediate 3-A: 5-bromo-8-methoxyquino...

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Abstract

The present invention relates to the technical field of organic light-emitting materials, and provides a metal platinum (II) and palladium (II) complex light-emitting material containing a quinoline structural unit, as shown below. Compared with the bidentate ligand platinum complexes, the tetradentate ligand-based cyclometal platinum(II) and palladium(II) complexes provided by the present invention have strong molecular rigidity and can effectively suppress non-radiation generated by molecular vibration. The quantum efficiency will be greatly improved, and it has broad application prospects in many fields such as OLED display and lighting.

Description

【Technical field】 [0001] The invention relates to the technical field of metal organic light-emitting materials, in particular to a tetradentate ring metal platinum (II) and palladium (II) complex light-emitting material containing a quinoline structural unit and an application thereof. 【Background technique】 [0002] Organic Light-Emitting Diode (OLED) is a new generation of full-color display and lighting technology. OLED is an autonomous light-emitting device that does not require a backlight and is energy-saving; it has low driving voltage, fast response speed, high resolution and contrast, wide viewing angle, and wide temperature range; it can also use cheap glass as a substrate, if flexible A flexible display device can be prepared by using the plastic as a substrate; in addition, it has the advantages of low cost, simple production process, and large-area production. Therefore, OLED has broad and huge application prospects in high-end electronic products and aerospac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D487/04C09K11/06H01L51/54
CPCC07D401/14C07D487/04C09K11/06C09K2211/185C09K2211/1029C09K2211/1044C09K2211/1059H10K85/346C07F15/0086H10K50/12H10K50/11C09K2211/1007
Inventor 李贵杰黄笛升佘远斌赵晓宇王子兴
Owner ZHEJIANG UNIV OF TECH
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