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A Class of Phosphorescent Luminescent Materials of Tetradental Cyclometal Platinum(ii) Complexes

A phosphorescence luminescent material, metal platinum technology, applied in the direction of luminescent materials, platinum-based organic compounds, platinum-group organic compounds, etc., can solve the problem of high purity of luminous color, achieve high phosphorescent quantum efficiency, easy modification and adjustment, and definite molecular weight Effect

Active Publication Date: 2021-11-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although people's research on phosphorescent materials of cyclometallic iridium (III) and platinum (II) complexes is deepening, there are still many problems in the field of OLEDs, such as phosphorescent materials with high emission color purity, saturated and efficient red light materials, The stability of fluorine-containing blue phosphorescent materials, stable and efficient blue phosphorescent materials and other issues, phosphorescent materials that can meet the needs of commercialization are still extremely limited.

Method used

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  • A Class of Phosphorescent Luminescent Materials of Tetradental Cyclometal Platinum(ii) Complexes
  • A Class of Phosphorescent Luminescent Materials of Tetradental Cyclometal Platinum(ii) Complexes
  • A Class of Phosphorescent Luminescent Materials of Tetradental Cyclometal Platinum(ii) Complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: The synthetic route of the phosphorescent material Pt1 of tetracyclic metal platinum complex is as follows:

[0038]

[0039] Synthesis of 2-(3-methoxyphenyl)-2H-1,2,3-triazole 1A and 1-(3-methoxyphenyl)-2H-1,2,3-triazole 1A' : Add 2H-1,2,3-triazole (2.04g, 30.0mmol, 1.0eq) and CuI (571.0mg, 3.0mmol, 0.10eq) to a 100mL three-neck flask with a magnetic rotor and a condenser, and prepare Body L-proline (690.0mg, 6mmol, 0.20eq) and K 2 CO 3 (8.29g, 60.0mmol, 2.0eq). The nitrogen was purged three times, then 3-methoxybromobenzene (7.53 mL, 60.0 mmol, 2.0 eq) and solvent dimethyl sulfoxide (60 mL) were added. The reaction mixture was placed in an oil bath at 120° C. for 3 days. Cool to room temperature, add 100 mL of water to quench the reaction, add 100 mL of ethyl acetate to dilute, filter with diatomaceous earth, and wash thoroughly with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate. Filtration, the solvent was distilled off ...

Embodiment 2

[0043] Embodiment 2: The synthesis route of tetradentate ring metal platinum complex phosphorescent material Pt2 is as follows:

[0044]

[0045] Synthesis of 1-(3-hydroxyphenyl)-1H-1,2,3-triazole 1B: 1-(3-methoxyphenyl)-1H-1,2,3- Triazole 1A' (1.36g, 7.70mmol) and concentrated hydrobromic acid (20.0mL, concentration 48%) and acetic acid (40.0mL) were refluxed at 120°C for 2 days in a one-necked flask equipped with a magnetic stirrer and a condenser . Then the mixture was allowed to cool to room temperature naturally, and the organic solvent and water were distilled off under reduced pressure, and the resulting mixture was neutralized with sodium bicarbonate solution until no bubbles occurred. Extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain 1.24 g of the target product as a brown solid, with a yield of 99%. 1 HNMR (500MHz, DMSO-d 6 ): δ6.86-6.89(m,1H),7.30-7.31(m,2H),7.37-7.39...

Embodiment 3

[0048] Example 3: The synthetic route of tetradentate ring metal platinum complex phosphorescent material Pt3 is as follows:

[0049]

[0050] Synthesis of 2-(3-hydroxyphenyl)-1,3,4-oxadiazole:

[0051] A mixture of methyl 3-hydroxybenzoate (6.85g, 45.0mmol), hydrazine hydrate (11.2mL, 80% aqueous solution) and ethanol (60mL) was heated to reflux for 48 hours, then cooled to room temperature, the precipitate was filtered off, washed with cold water, After drying, 4.34 g of the target product 3-hydroxybenzoic hydrazide was obtained with a yield of 63%. Then the obtained 3-hydroxybenzoic hydrazide (4.34 g, 28.5 mmol) was mixed with trimethoxymethane (19.7 mL), and heated to reflux for 24 hours. After cooling, excess trimethoxymethane was removed under reduced pressure, and the resulting crude product was separated and purified by silica gel column chromatography to obtain 4.24 g of the target product with a yield of 92%. 1 H NMR (500MHz, DMSO-d 6 ):δ7.01-7.03(m,1H),7.40-7....

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Abstract

The present invention discloses a class of four-dentate ring metal platinum (II) phosphorescent luminescent material as shown in formula (I): wherein, the five-membered heteroaromatic group Ar is selected from one of the following: 2H-1, 2,3‑triazole where X 1 =N,X 2 =N,X 3 =CH); 1H-1,2,3-triazole wherein, X 1 =CH,X 2 =N,X 3 = N; 1,3,4-oxadiazole wherein, X 1 =O,X 2 =C,X 3 = N; oxazole wherein, X 1 =O,X 2 =C,X 3 =CH or thiazole wherein, X 1 =S,X 2 =C,X 3 =CH. The application of one or two or more of the four-ring metal platinum (II) phosphorescent luminescent materials in the present invention as a light-emitting layer of an organic light-emitting device. The four-ring metal platinum (II) phosphorescent luminescent material of the present invention has strong molecular rigidity, can effectively reduce the energy consumed by molecular vibration, has high phosphorescent quantum efficiency, and has good chemical stability and thermal stability.

Description

technical field [0001] The invention relates to the field of phosphorescent luminescent materials, in particular to a class of tetradentate ring metal platinum (II) complex phosphorescent materials containing five-membered heteroaromatic rings. Background technique [0002] OLED is an Organic Light-Emitting Diode (Organic Light-Emitting Diode) or an Organic Light-Emitting Device (Organic Light-Emitting Device), also known as an Organic Electroluminescent Device. Organic electroluminescence refers to a luminescent phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular luminescent materials directly convert electrical energy into light energy under the action of a forward bias electric field. Generally, OLED devices have at least one organic layer between the anode and cathode. Under the action of the forward bias voltage derived from the current, the anode and cathode inject holes and electrons into the organic layer, respectively, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07F15/0086C09K2211/1029C09K2211/1059C09K2211/1033C09K2211/1037C09K2211/1048C09K2211/185H10K85/346H10K50/11
Inventor 李贵杰佘远斌赵向东方坤
Owner ZHEJIANG UNIV OF TECH
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