Metal platinum (II) and palladium (II) complexes, organic light emitting devices and display or lighting devices

An organic light-emitting device, metal platinum technology, applied in organic chemistry, luminescent materials, electric solid-state devices, etc., can solve the problems of bidentate ligands that are easy to twist, low rigidity, vibration, etc., and achieve non-radiative attenuation suppression and good thermal stability Sexuality and broad application prospects

Active Publication Date: 2022-07-29
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent molecular efficiency of aluminum complexes is low, so they cannot be used as ideal light-emitting layer materials.
In 2016, Ilya Taydakov et al. designed a bidentate platinum complex based on 8-hydroxyquinoline, which achieved red-orange light emission at 640nm, but its quantum efficiency in solution can only reach about 1.5%.
[0006] 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. Metal platinum (II) complex molecules need a second complex 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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  • Metal platinum (II) and palladium (II) complexes, organic light emitting devices and display or lighting devices
  • Metal platinum (II) and palladium (II) complexes, organic light emitting devices and display or lighting devices
  • Metal platinum (II) and palladium (II) complexes, organic light emitting devices and display or lighting devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0132] Example 1: The platinum complex Pt1 can be synthesized as follows:

[0133]

[0134] Synthesis of intermediate 8-methoxyquinoline: In a 100mL there-necked flask with a magnetic rotor, add 8-hydroxyquinoline (5.00g, 34.5mmol, 1.00 equivalent), N,N-dimethylformamide ( 40mL), then it was placed in a low temperature bath and stirred, and after the temperature was lowered, sodium hydrogen (1.38g, 34.5mmol, 1.00 equiv.) with a mass fraction of 60% was slowly added, and iodomethane (5.14g, 36.3g) was added after being placed at room temperature. mmol, 1.05 equivalents), 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 und...

Embodiment 2

[0140]Example 2: The platinum complex Pt3 can be synthesized as follows:

[0141]

[0142] Synthesis of 5-bromo-8-methoxyquinoline: add 8-methoxyquinoline (4.76 g, 29.9 mmol, 1.00 equiv) to a 500 mL there-necked flask with a magnetic rotor, add 230 mL of acetonitrile, and then slowly add N-Bromosuccinimide (5.32 g, 31.3 mmol, 1.05 equiv) was reacted for 8 hours. The reaction mixture was added with aqueous sodium sulfite to quench the reaction, diluted with dichloromethane, extracted three times with dichloromethane, and the organic phases were combined and dried over anhydrous sodium sulfate. The crude product was separated and purified by silica gel column chromatography, eluent (dichloromethane / ethyl acetate = 10:1), and the solvent was distilled off under reduced pressure to obtain 5.8 g of a pale yellow solid with a yield of 82%. used directly in the next reaction.

[0143] Synthesis of intermediate 3-A: 5-bromo-8-methoxyquinoline (500 mg, 2.1 mmol, 1.00 equiv.), p-te...

Embodiment 3

[0149] Example 3: The platinum complex Pt10 can be synthesized as follows:

[0150]

[0151] Synthesis of intermediate L10-Me: add 2-bromo-8-methoxyquinoline (1.00 equiv.), M-10 (1.05 equiv.), CuI (0.1 equiv.), 2 -picolinic acid (0.2 equiv), K 3 CO 4 (2.1 equivalents), after the nitrogen was purged three times, dimethyl sulfoxide was added by injection, the temperature was increased to 120° C., and the reaction was carried out for 48 hours. The reaction mixture was quenched with water, diluted with ethyl acetate, extracted three times with ethyl acetate and dried with anhydrous sodium sulfate. The obtained crude product was separated and purified by silica gel column chromatography, and the solvent was distilled off under reduced pressure to obtain the product L10-Me.

[0152] Synthesis of intermediate L10: add L10-Me (1.00 equiv.), a mixed system of hydrogen bromide and acetic acid to a three-necked flask with a magnetic rotor in turn, and heat up to 120°C for reflux rea...

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Abstract

The invention provides a metal platinum (II) and palladium (II) complex, an organic light-emitting device and a display or lighting device, and the structure of the metal platinum (II) and palladium (II) complex is as shown in the following formula (I). The cyclometalated platinum (II) and palladium (II) complex based on a tetradentate ligand has relatively strong rigidity, can effectively inhibit non-radiative transition generated by molecular vibration, and can be applied to the field of organic light-emitting devices, such as organic light-emitting devices, organic light-emitting devices, organic light-emitting devices, organic light-emitting devices, organic light-emitting devices, organic light-emitting devices, organic light-emitting devices, organic light-emitting devices and the like. The quantum efficiency and the luminous intensity are relatively high. Meanwhile, the tetradentate phosphorescent metal complex disclosed by the invention is a novel parent nucleus structure, and a series of efficient phosphorescent metal platinum complexes can be developed. The material has an excellent application prospect in the fields of OLED display, illumination and the like, especially in the field of light-emitting layer materials.

Description

technical field [0001] The invention relates to a metal platinum (II) and palladium (II) complex, in particular to a metal platinum (II) and palladium (II) complex, an organic light-emitting device and a display or lighting device, belonging to the technical field of organic light-emitting materials . Background technique [0002] Organic Light-Emitting Diode (OLED) is a new generation of full-color display and lighting technology. Compared with the shortcomings of liquid crystal display, such as slow response speed, small viewing angle, need for backlight, and high energy consumption, OLED, as an autonomous light-emitting device, does not require a backlight and saves energy; and its driving voltage is low, response speed is fast, and resolution and contrast are high. , Wide viewing angle, excellent low temperature performance; OLED devices can be made thinner and can be made into flexible structures. In addition, it also has the advantages of low production cost, simple ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0086C07F15/006C09K11/06C09K2211/185H10K85/341H10K85/346H10K50/11Y02E10/549
Inventor 李贵杰佘远斌黄笛升赵晓宇
Owner ZHEJIANG UNIV OF TECH
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