Dibenzo-18-crown-6-based cyclometalated iridium complex and application thereof

A technology of iridium complex and metal iridium, which is applied to compounds containing elements of Group 8/9/10/18 of the periodic table, indium organic compounds, platinum group organic compounds, etc., can solve the problem of reducing the luminous efficiency, lifetime, concentration of devices quenching, the reduction of the efficiency of phosphorescent devices, etc., to avoid the quenching effect, improve the luminescence performance, and improve the luminescence performance.

Active Publication Date: 2015-04-01
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main problems of polymer electrophosphorescent devices are: (1) When the organic small molecule phosphorescent material (guest) is doped into the polymer host material, under the action of an electric field, the aggregation of phosphorescent molecules is easy to occur, resulting in phase separation, resulting in concentration Quenching, reducing the luminous efficiency and lifetime of the device; (2) Under high current density, the efficiency of electrophosphorescent devices decreases rapidly

Method used

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  • Dibenzo-18-crown-6-based cyclometalated iridium complex and application thereof
  • Dibenzo-18-crown-6-based cyclometalated iridium complex and application thereof
  • Dibenzo-18-crown-6-based cyclometalated iridium complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of Dibenzo-18-Crown-6 Borate

[0049]

[0050] (1) Synthesis of dibenzo-18-crown-6

[0051] Put 22 g (0.2 mol) catechol, 30.03 g (0.21 mol) 1-chloro-2-(2-chloroethoxy) ethane and 110.4 g potassium carbonate in a 500 mL round bottom flask, add 350 mL of N,N-dimethylformamide (DMF) solution, the reaction was heated to reflux, and the reaction was stirred for 24 h. Cool to room temperature, pour into a large amount of water, and extract with dichloromethane 3 times. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the organic solvent was distilled off. Purified by column chromatography (silica gel as the stationary phase, petroleum ether: ethyl acetate = 4:1 as the eluent) to obtain 7.57 g of a white solid with a yield of 21%. 1 H NMR (300 MHz, CDCl 3 , TMS) δ (ppm): 6.88 (s, 8H), 4.16~4.13 (t, J = 4.36 Hz, 8H), 3.93~3.90 (t, J = 4.35 Hz, 8H).

[0052] (2) Synthesis of 4-bromo-dibenzo-18-crown-6

[0053] Add 3.6 g ...

Embodiment 2

[0057] Bromination fac -Synthesis of three (2-phenylpyridine) iridium

[0058]

[0059] (1) fac -Three (2-phenylpyridine) iridium (Ⅲ) [ fac -Ir(ppy) 3 ]Synthesis

[0060] Add 1.5 g (10 mmol) of 2-phenylpyridine, 21 mL of ethylene glycol monoethyl ether and 7 mL of water into a 50 mL three-neck flask, and quickly add 1.4 g (4.0 mmol) of IrCl under argon protection 3 ·3H 2 O, 100 °C constant temperature reaction for 20 h. After cooling, a yellow solid was produced, which was filtered by suction, washed with water and a little ethanol successively, and dried in vacuum to obtain 2.42 g of a yellow powder. The product was directly used in the next reaction without further separation and purification.

[0061] In a 50 mL three-neck flask, add 0.8 g (0.75 mmoL) of the reaction product of the previous step, 0.62 g (4.0 mmoL) of 2-phenylpyridine, 424 mg (4.0 mmoL) of sodium carbonate, 0.6 mL of acetylacetone, and 0.6 mL of three Ethylamine and ethylene glycol 30 mL. Under t...

Embodiment 7

[0069] Dibenzo-18-crown-6 radicalization fac -Synthesis of three (2-phenylpyridine) iridium

[0070]

[0071] (1) Two (2-phenylpyridine)-(2-(5-(18-crown-6-yl)phenyl)pyridine) iridium (Ⅲ) [(ppy) 2 Synthesis of Ir(ppycr)]

[0072] 368 mg (0.5 mmol) of bis(2-phenylpyridine)-(2-(5-bromophenyl)pyridine)iridium(Ⅲ)[(ppy) 2 Ir(ppyBr)], 292 mg (0.6 mmol) of dibenzo-18-crown-6 borate and 20 mL of 2.0 M potassium carbonate aqueous solution, as well as 40 mL of toluene and 20 mL of ethanol were added to a 150 mL two-necked flask, and argon Add 30 mg (0.025 mmol) tetrakis(triphenylphosphine) palladium under gas protection, heat to 90 °C, and react for 24 h. After cooling to room temperature, the reaction solution was poured into deionized water, extracted three times with dichloromethane, and the organic phases were combined and washed with water. Anhydrous MgSO 4 After drying overnight, the volatile solvent was evaporated by a rotary evaporator. The crude product was separated an...

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Abstract

The invention discloses an electrophosphorescent material containing a dibenzo-18-crown-6-based cyclometalated iridium complex, and an application thereof in a polymer electroluminescent device. According to the cyclometalated iridium complex disclosed by the invention, because dibenzo-18-crown-6 has a quite high steric hindrance, intermolecular aggregation can be effectively reduced, thus avoiding a triplet-triplet (T-T) quenching effect. Meanwhile, the dibenzo-18-crown-6 group has an electron transmission capacity to a certain extent and is capable of effectively adjusting the electron injection and transmission capacities of the iridium complex, thus greatly improving the luminescent performance of the material in the electroluminescent device. The cyclometalated iridium complex disclosed by the invention can be used as a green luminescent material and applied to an organic electroluminescent device, thus providing a new way for obtaining an efficient organic electrophosphorescent material.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a class of electroluminescent materials containing dibenzo-18-crown-6 base cyclometal iridium complexes and the application of the complexes in polymer electroluminescent devices. Background technique [0002] In 1998, Ma Yuguang's group at Jilin University first used the osmium complex [Os(CN) 2 (pph 3 ) 2 BPy] was doped into polyvinyl carbazole (PVK) to prepare phosphorescent electroluminescent devices, but because of its low efficiency, it failed to attract attention (Synth. Met., 1998, 94, 245). Almost at the same time, the Forrest group of Princeton University and the Thompson group of the University of Southern California also reported that platinum octaethylporphyrin (PtOEP) was doped into the small molecule host material aluminum octahydroxyquinoline (Alq 3 ), a high-efficiency phosphorescent device was obtained, with internal quantum efficiency and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D405/10C09K11/06H01L51/54
CPCC09K11/06C07D405/10C07F15/0033C09K2211/185C09K2211/1088C09K2211/1029H10K85/342
Inventor 梁爱辉黄贵陈永亮钟声亮
Owner JIANGXI NORMAL UNIV
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