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A kind of pyridazine iridium complex containing alkyl hindering group and its preparation method and application

A technology of iridium complexes and pyridazines, which is applied in the field of pyridazine iridium complexes and their preparation, can solve the problems of expensive raw materials or raw material adaptability, weak luminescence concentration of iridium complexes, obvious quenching, etc., and achieve reduction Luminescence quenching, phosphorescence quenching is small, and the effect of reducing the intermolecular force

Active Publication Date: 2019-08-02
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
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Problems solved by technology

[0006] Aiming at the problems that the preparation of the existing pyridazine tricyclometalated iridium complexes requires expensive raw materials or the raw materials are not well adaptable and the problem that the luminescence concentration of the iridium complexes is obviously quenched, the present invention provides a bicycloalkyl-containing Pyridazine iridium complex and preparation method thereof

Method used

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  • A kind of pyridazine iridium complex containing alkyl hindering group and its preparation method and application
  • A kind of pyridazine iridium complex containing alkyl hindering group and its preparation method and application
  • A kind of pyridazine iridium complex containing alkyl hindering group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 2.3g (10mmol) 1,4-dichloro-5,6,7,8-tetrahydro-5,8-ethanephthalazine, 2.4g (20mmol) phenylboronic acid and 1.4g (10mmol) potassium carbonate to 250mL In the round bottom flask, add 0.23g (0.2mmol) Pd (PPh 3 ) 4 , then pour 30mL THF and 15mL water, N 2 Protection, reflux at 100°C for 12h. Cool, spin dry tetrahydrofuran, extract with dichloromethane to obtain the lower organic phase, spin dry, and separate by silica gel column chromatography with petroleum ether: ethyl acetate = 1:1 eluent to obtain 0.62 g of 1,4-diphenyl - 5,6,7,8-Tetrahydro-5,8-ethanephthalazine as a white solid in 20% yield. The NMR spectrum of the product is: 1 H NMR (400MHz, CDCl 3 )δ7.71(dd,J=7.5,5.8Hz,5H),7.54-7.48(m,5H),3.44(s,2H),1.88(d,J=8.0Hz,4H),1.46(d,J =7.6Hz, 4H). The mass spectrum of product is: MS ((+)-ESI): m / z=313.33 (calcd.313.17forC 22 h 21 N 2 ,[M+H + ]).

[0045] 0.94g (3mmol) 1,4-diphenyl-5,6,7,8-tetrahydro-5,8-ethanephthalazine, 0.56g (1mmol) IrCl 3 · (tht) 3 , 0...

Embodiment 2

[0048] Add 2.3g (10mmol) 1,4-dichloro-5,6,7,8-tetrahydro-5,8-ethanephthalazine, 4.8g (40mmol) phenylboronic acid and 8.4g (60mmol) potassium carbonate to 500mL In the round bottom flask, add 1.15g (1mmol) Pd (PPh 3 ) 4 , then poured into 60mL tetrahydrofuran and 30mL water, N 2 Protection, reflux at 150°C for 5h. Cool, spin dry THF, extract with dichloromethane to obtain the lower organic phase, spin dry, and separate by silica gel column chromatography with petroleum ether: ethyl acetate = 1:1 eluent to obtain 0.78 g of 1,4-diphenyl - 5,6,7,8-Tetrahydro-5,8-ethanephthalazine as a white solid in 25% yield. The NMR and mass spectra of the product are basically the same

[0049] Example 1.

[0050]1.57g (5mmol) 1,4-diphenyl-5,6,7,8-tetrahydro-5,8-ethanephthalazine, 0.56g (1mmol) IrCl 3 · (tht) 3 , 0.246g (3mmol) anhydrous sodium acetate and 60mL decahydronaphthalene solution, N 2 Protected and reacted at 250°C for 40h. Cool down after the reaction, distill off decahydr...

Embodiment 3

[0052] 2.3g (10mmol) 1,4-dichloro-5,6,7,8-tetrahydro-5,8-ethanephthalazine, 5.4g (20mmol) 4-(trifluoromethyl)phenylboronic acid pina Add alcohol ester and 1.4g (10mmol) potassium carbonate to a 250mL round bottom flask, add 0.2g (0.3mmol) PdCl 2 (dppf), then pour 30mL tetrahydrofuran and 15mL water, N 2 Protection, reflux at 100°C for 12h. Cool, spin dry tetrahydrofuran, extract with dichloromethane to obtain the lower organic phase, spin dry, and use petroleum ether: ethyl acetate = 1:1 eluent silica gel column chromatography to obtain 2.0 g 1,4-bis(p- Trifluoromethylphenyl)-5,6,7,8-tetrahydro-5,8-ethanephthalazine as a white solid, yield 44%. The NMR spectrum of the product is: 1 H NMR (400MHz, CDCl 3 ) δ 7.82 (s, 8H), 3.40 (s, 2H), 1.93 (d, J=8.0Hz, 4H), 1.47 (d, J=7.8Hz, 4H). 19 F NMR (CDCl 3 ,367MHz) δ-62.73(s,6F). The mass spectrum of product is: MS ((+)-ESI): m / z=449.42 (calcd.449.14for C 24 h 19 f 6 N 2 ,[M+H + ]).

[0053] 1.35g (3mmol) 1,4-bis(p-trifluor...

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Abstract

The invention discloses a pyridazine iridium complex containing an alkyl steric hindrance group, a preparation method and an application thereof, and belongs to the field of organic photoelectric materials. The method solves the problems in the prior art that the preparation of the pyridazine tricyclometalated iridium complexes requires expensive raw materials or the raw materials have poor adaptability and the problem that the luminescence concentration of the iridium complexes is obviously quenched. The general structural formula of the pyridazine iridium complex containing an alkyl hindering group of the present invention is shown in formula (1), and the preparation method is: first synthesize a pyridazine ligand containing a bicycloalkyl group, and then synthesize the bicycloalkyl group The pyridazine ligand and IrCl 3 .(tht) 3 The reaction generates pyridazine tricyclic metallized iridium complexes, the concentration quenching of the obtained iridium complexes is significantly reduced, and the doping concentration of the organic electronic light-emitting device prepared thereby is greatly increased.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and more specifically relates to a pyridazine iridium complex containing an alkyl steric group and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have self-illumination, no backlight, high contrast, thin thickness, wide viewing angle, fast response speed, can be used for flexible panels, wide operating temperature range, simple structure and manufacturing process, etc. Excellent characteristics, considered to be the next generation of flat panel display emerging application technology. In phosphorescent metal complexes, the introduction of heavy metal atoms can increase the spin-orbit coupling, thereby shortening the phosphorescence lifetime and improving the luminous efficiency, and the internal quantum efficiency can reach 100%. Among these complexes, iridium complexes have good luminescent properties, such as high colo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 童碧海陈熳马秀芳梅群波周世雄胡伟康
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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