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Thieno[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 and difficulty in synthesizing pyridazine intermediates and other problems, to achieve the effect of increasing electron cloud density, improving hole transport ability, and easy preparation.

Pending Publication Date: 2020-07-03
ANHUI UNIVERSITY OF TECHNOLOGY
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AI Technical Summary

Problems solved by technology

[0008] Aiming at the problems that existing cyclometal iridium complexes are very sensitive to oxygen and the quantum efficiency of pyridazine iridium complexes is not high, the present invention provides a thieno[2,3-d]pyridazine cyclometal iridium complex, The cyclometalated ligand is prepared by fusing the thiophene group with the pyridazine group and used to synthesize the cyclometalated iridium complex, which achieves the goal of further improving the luminous efficiency and reducing the sensitivity to oxygen molecules while maintaining the stability of the iridium complex. Purpose
[0009] The present invention also provides a method for synthesizing monochloro-substituted thieno[2,3-d]pyridazine intermediates, the purpose of which is to solve the problem of difficult synthesis of monochloro-substituted thieno[2,3-d]pyridazine intermediates

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Dissolve 1.89g (15mmol) of 3-methylthiophene-2-carbaldehyde in 30mlTHF and place in a 250ml three-necked flask, and 3.74g (15mmol) of (3-(trifluoromethyl)phenyl)magnesium bromide in 50mlTHF In a constant pressure dropping funnel, N 2 After the dropwise addition, stir at room temperature for 2 hours, then add hydrochloric acid to hydrolyze and adjust the pH to 3-7 to obtain (3-methylthiophen-2-yl)(3-(trifluoromethyl)phenyl)methanol as a white solid 3.1 g, yield 76%.

[0057] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ7.74-7.72 (m, 2H), 7.58-7.54 (m, 1H), 7.45-7.43 (m, 1H), 7.38-7.32 (m, 1H), 7.18 (d, J=9.2Hz, 1H) , 6.36(s, 1H), 3.83(s, 1H), 2.35(s, 3H). 19 F NMR (377MHz, CDCl 3 ) δ-62.12 (s, 3F). Product mass spectrum: MS ((+)-ESI): m / z=272.2647 (calcd.272.2852for [C 13 h 11 f 3 OS][M+H] + ). The structural formula of the product is as follows:

[0058]

[0059] Take 2.72g (10mmol) (3-methylthiophen-2-yl) (3-(trifluoromethyl)phenyl)methanol and add 31.6...

Embodiment 2

[0075] The preparation method of 4-chloro-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine used in this example is basically the same as that of Example 1, the difference is that the reaction The amount of compound was increased to give 3.2 g of 4-chloro-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine.

[0076] 3.2g (10mmol) 4-chloro-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine, 1.4g (10mmol) 2,6-dimethylbenzenesulfide Phenol and 2.8g (20mmol) sodium hydroxide were added to a 150mL round bottom flask, then poured into 30mL dry DMF, N 2 protection, and reacted at 130°C for 10 hours. Cool, distill off DMF under reduced pressure, and separate by silica gel column chromatography with petroleum ether: ethyl acetate = 9:1 eluent to obtain 4-(2,6-dimethylphenylthio)-7-(3-( Trifluoromethyl)phenyl)thieno[2,3-d]pyridazine was 3.5 g of white solid, and the yield was 84%.

[0077] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ8.31 (s, 1H), 8.22 (d, J = 7.8Hz, 1H), 7....

Embodiment 3

[0083] The preparation method of 4-chloro-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine used in this example is basically the same as that in Example 2.

[0084] 3.2g (10mmol) 4-chloro-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine, 5.3g(12mmol)bis(3,5-bis(tri Fluoromethyl) phenyl) amine and 0.5g (20mmol) lithium diisopropylamide were added to a 150mL round bottom flask, then poured into 80mL dry tetrahydrofuran, N 2 protection, and reacted at room temperature for 12 hours. The product was precipitated by adding water, filtered and dried, and separated by silica gel column chromatography with petroleum ether:ethyl acetate=6:1 eluent to obtain 4-(bis(3,5-bis(trifluoromethyl)phenyl)amino )-7-(3-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazine was 4.8 g of white solid, and the yield was 67%.

[0085] NMR of the product: 1 H NMR (400MHz, CDCl 3 )δ8.31(s, 1H), 8.20(d, J=10.3Hz, 1H), 7.63(d, J=5.9Hz, 2H), 7.43-7.35(m, 2H), 7.30-7.27(m, 2H ), 7.25-7.20 (m, 1H), 7.07 ...

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Abstract

The invention discloses a thieno[2,3-d]pyridazine cyclometalated iridium complex and a preparation method thereof, belonging to the field of organic photoelectric materials. The thieno[2,3-d]pyridazine cyclometalated iridium complex provided by the invention overcomes the problems that an existing cyclometalated iridium complex is very sensitive to oxygen, and the quantum efficiency of the existing pyridazine iridium complex is not high. The preparation method comprises the following steps: synthesizing a monochloro-substituted thieno[2,3-d]pyridazine intermediate through a four-step reaction;mixing the monochloro-substituted thieno[2,3-d]pyridazine intermediate with substituted phenol, substituted thiophenol, substituted aniline or substituted carbazole active hydrogen-containing compounds dissolved in an organic solvent, adding alkali, and carrying out a reaction to generate thieno[2,3-d]pyridazine ligand; and mixing the obtained thieno[2,3-d]pyridazine ligand with iridium trichloride and a solvent, and carrying out a reaction 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 thieno[2,3-d]pyridazine cyclometal iridium complex 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, heavy metal atoms are introduced, and through the heavy atom effect, spin-orbi...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342
Inventor 童碧海周跃跃梅群英田勇攀赵卓姚永林
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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