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4,7-diarylthieno[2, 3-d] pyridazine cyclometalated iridium complex and preparation method thereof

An iridium complex, 3-d technology, applied in indium organic compounds, platinum group organic compounds, chemical instruments and methods, etc., can solve the problem of low quantum efficiency of pyridazine iridium complexes

Active Publication Date: 2020-07-07
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the problems that existing ring metal iridium complexes are very sensitive to oxygen and the quantum efficiency of pyridazine iridium complexes is not high, the present invention provides a 4,7 -Diarylthieno[2,3-d]pyridazine cyclometal iridium complexes, through the fusion of thiophene groups and pyridazine groups to prepare cyclometalated ligands and to synthesize cyclometal iridium complexes, reaching The purpose of further improving the luminous efficiency and reducing the sensitivity to oxygen molecules under the premise of maintaining the stability of the iridium complex

Method used

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  • 4,7-diarylthieno[2, 3-d] pyridazine cyclometalated iridium complex and preparation method thereof
  • 4,7-diarylthieno[2, 3-d] pyridazine cyclometalated iridium complex and preparation method thereof
  • 4,7-diarylthieno[2, 3-d] pyridazine cyclometalated iridium complex and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Add 3.8g (20mmol) of 3-trifluoromethylphenylboronic acid, 2.05g (10mmol) of 4,7-dichlorothieno[2,3-d]pyridazine and 1.4g (10mmol) of anhydrous potassium carbonate into 120mL In the tube, add 0.2g (0.3mmol) Pd(dppf)Cl 2 , the solvent was 15mL tetrahydrofuran and 10mL water, heated to 130°C, and reacted under nitrogen atmosphere for 12 hours. After the reaction, cool to room temperature, spin dry THF, extract with dichloromethane to obtain the lower organic phase, dry with anhydrous sodium sulfate, spin dry, and purify the product by column chromatography. The polarity of the developer is petroleum ether: Ethyl acetate = 1:1, 3.8 g of 4,7-bis(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine as a white solid was obtained with a yield of 90%.

[0064] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ8.53(s,1H),8.42(d,J=7.8Hz,1H),8.29(s,1H),8.21(d,J=7.8Hz,1H),8.01(d,J=5.5Hz, 1H), 7.88-7.84(m, 2H), 7.80-7.74(m, 3H). 19 F NMR (377MHz, CDCl 3 )δ-62.60(s,3F),-62.69(s,3F). P...

Embodiment 2

[0070] Add 3.8g (20mmol) of 3-trifluoromethylphenylboronic acid, 2.05g (10mmol) of 4,7-dichlorothieno[2,3-d]pyridazine and 1.4g (10mmol) of anhydrous potassium carbonate into 120mL In the tube, add 0.2g (0.3mmol) Pd(dppf)Cl 2 , the solvent was 15mL tetrahydrofuran and 10mL water, heated to 130°C, and reacted under nitrogen atmosphere for 12 hours. After the reaction, cool to room temperature, spin dry THF, extract with dichloromethane to obtain the lower organic phase, dry with anhydrous sodium sulfate, spin dry, and purify the product by column chromatography. The polarity of the developer is petroleum ether: Ethyl acetate = 1:1, 3.8 g of 4,7-bis(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine as a white solid was obtained with a yield of 90%.

[0071] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ8.53(s,1H),8.42(d,J=7.8Hz,1H),8.29(s,1H),8.21(d,J=7.8Hz,1H),8.01(d,J=5.5Hz, 1H), 7.88-7.84(m, 2H), 7.80-7.74(m, 3H). 19 F NMR (377MHz, CDCl 3 )δ-62.60(s,3F),-62.69(s,3F). P...

Embodiment 3

[0077] Add 3.8g (20mmol) of 3-trifluoromethylphenylboronic acid, 2.05g (10mmol) of 4,7-dichlorothieno[2,3-d]pyridazine and 1.4g (10mmol) of anhydrous potassium carbonate into 120mL In the tube, add 0.2g (0.3mmol) Pd(dppf)Cl 2 , the solvent was 15mL tetrahydrofuran and 10mL water, heated to 130°C, and reacted under nitrogen atmosphere for 12 hours. After the reaction, cool to room temperature, spin dry THF, extract with dichloromethane to obtain the lower organic phase, dry with anhydrous sodium sulfate, spin dry, and purify the product by column chromatography. The polarity of the developer is petroleum ether: Ethyl acetate = 1:1, 3.8 g of 4,7-bis(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine as a white solid was obtained with a yield of 90%.

[0078] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ8.53(s,1H),8.42(d,J=7.8Hz,1H),8.29(s,1H),8.21(d,J=7.8Hz,1H),8.01(d,J=5.5Hz, 1H), 7.88-7.84(m, 2H), 7.80-7.74(m, 3H). 19 F NMR (377MHz, CDCl 3 )δ-62.60(s,3F),-62.69(s,3F). P...

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Abstract

The invention discloses a 4,7-diarylthieno[2, 3-d] pyridazine cyclometalated iridium complex and a preparation method thereof, which belongs to the field of organic photoelectric materials. Accordingto the 4,7-diarylthieno[2,3-d] pyridazine cyclometalated iridium complex disclosed by the invention, the problems that an existing cyclometalated iridium complex is very sensitive to oxygen and a pyridazine iridium complex is not high in quantum efficiency are solved; the preparation method comprises the following steps: substituted phenylboronic acid or boric acid ester is added into chlorothieno[2, 3-d]pyridazine, meanwhile, 4,7-diarylthieno[2,3-d] pyridazine ligands are obtained through a reaction for a period of time in the presence of alkali, a catalyst and a solvent, and the molar ratioof chlorine to substituted phenylboronic acid or boric acid ester in chlorothieno [2,3-d] pyridazine is 1: 1; and the obtained 4, 7-diarylthieno [2,3-d] pyridazine ligand is mixed with iridium trichloride and a solvent, and a reaction is carried out for a period of time to obtain the thieno[2,3-d] pyridazine cyclometalated iridium complex.

Description

technical field [0001] The invention relates to a class of luminescent materials, in particular to a class of cyclometal iridium complex phosphorescent materials with 4,7-diarylthieno[2,3-d]pyridazine derivatives as ligands and a preparation method thereof . Background technique [0002] In recent years, compared with liquid crystal display (LCD), organic electroluminescence (OLED) has significant advantages such as low lighting voltage, high efficiency, light weight, low power consumption, and short switching time, so it has received extensive attention. And because it has excellent characteristics such as self-illumination, no need for backlight, high contrast, thin thickness, wide viewing angle, fast response speed, can be used for flexible panels, wide operating temperature range, and relatively simple structure and manufacturing process, it is considered to be a Emerging technology for the next generation of flat panel displays. In phosphorescent metal complexes, heav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0033C09K11/06C09K2211/185
Inventor 童碧海梅群英程伟田勇攀赵卓姚永林
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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