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Pyridazine iridium complexes containing alkyl steric-hindrance groups, and preparation method and application thereof

An iridium complex and pyridazine technology, applied in the field of pyridazine iridium complex and its preparation, can solve the problems of weak iridium complex luminescence concentration, obvious quenching, expensive raw materials or raw material adaptability, etc. Luminescence quenching, small phosphorescence quenching, and the effect of reducing intermolecular forces

Active Publication Date: 2017-09-15
ANHUI UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0006] Aiming at the problem 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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  • Pyridazine iridium complexes containing alkyl steric-hindrance groups, and preparation method and application thereof
  • Pyridazine iridium complexes containing alkyl steric-hindrance groups, and preparation method and application thereof
  • Pyridazine iridium complexes containing alkyl steric-hindrance groups, and preparation method and application thereof

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 poured into 30mL tetrahydrofuran and 15mL water, N 2 Protection, reflux at 100°C for 12h. 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 0.62 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) ...

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 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 0.78 g of 1,4-diphenyl - 5,6,7,8-Tetrahydro-5,8-ethanephthalazine as a white solid in 25% yield. The nuclear magnetic spectrum and mass spectrum of product are basically the same as in Example 1.

[0049] 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 react...

Embodiment 3

[0051] 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 + ]).

[0052] 1.35g (3mmol) 1,4-bis(p-trifluo...

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Abstract

The invention discloses pyridazine iridium complexes containing alkyl steric-hindrance groups, and a preparation method and application thereof, belonging to the field of organic photoelectric materials. The objective of the invention is to overcome the problems that raw materials for preparation of conventional pyridazine tris-cyclometalated iridium complexes are expensive or have poor adaptability and that conventional iridium complexes are obvious in quenching of luminescence concentration. The pyridazine iridium complexes containing the alkyl steric-hindrance groups in the invention have a general structural formula as shown in a formula (1). The preparation method for the pyridazine iridium complexes comprises the following steps: systhesizing pyridazine ligands containing dicycloalkyl groups; and then reacting the pyridazine ligands containing the dicycloalkyl groups with IrCl3.(tht)3 so as to produce the pyridazine tris-cyclometalated iridium complexes. The prepared iridium complexes are obviously reduced in concentration quenching, and organic electronic luminescent devices prepared from the iridium complexes are greatly improved in doping concentration.

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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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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