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Arylamine derivative and organic electroluminescent device thereof

An aromatic amine derivative, electromechanical technology, applied in electric solid devices, electrical components, organic chemistry, etc., can solve the problems of OLED device color purity, low luminous efficiency, low molecular orbital energy level, and shortened service life, etc. Achieve the effect of improving luminous efficiency and color purity, good film formation and stability, and improving performance

Active Publication Date: 2018-11-16
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the hole transport materials currently used in OLED devices have a low highest occupied molecular orbital energy level (HOMO) and a low value of the first triplet excited state (T1), so that the excitons generated in the light-emitting layer are transferred to the hole The interface of the hole transport layer or the inside of the hole transport layer will eventually lead to the luminescence at the interface of the light emitting layer or the charge imbalance in the light emitting layer, so that light will be emitted on the interface of the hole transport layer, and the color purity and luminous efficiency of the OLED device will be changed. low, shortened service life

Method used

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  • Arylamine derivative and organic electroluminescent device thereof
  • Arylamine derivative and organic electroluminescent device thereof
  • Arylamine derivative and organic electroluminescent device thereof

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preparation example Construction

[0079] The preparation method of aromatic amine derivatives described in the present invention can be prepared through the following synthetic route:

[0080]

[0081] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 as above.

[0082] (1) Using 4-iodo-4'-bromobiphenyl (compound A) as raw material, and containing Ar at the same time 1 and Ar 2 The Buchwald-Hartwig coupling reaction of the arylamine produces intermediate (B);

[0083] (2) intermediate (B) and containing Ar 3 The aromatic amine compound of the same by Buchwald-Hartwig coupling reaction, obtains intermediate (C);

[0084] (3) Finally, intermediate (C) and containing Ar 4 Buchwald-Hartwig coupling reaction of the bromide to obtain the target compound (I).

[0085] The present invention has no special limitation on the reaction conditions of the above-mentioned reactions, and the reaction conditions well-known to those skilled in the art can be adopted. The preparation method is simple and the raw materials are readi...

Embodiment 1

[0091] Embodiment 1: the preparation of intermediate B

[0092] Preparation of Intermediate B-1:

[0093]

[0094] Under an argon atmosphere, 17.95g (50mmol) of compound (A), 16.07g (50mmol) of bis(4-biphenyl)amine, and 9.60g (100mmol) of sodium tert-butoxide were dissolved in 500ml of dehydrated toluene, and stirred Then, 0.23 g (1 mmol) of palladium acetate and 0.20 g (1 mmol) of triphenylphosphine were added, the temperature was raised to 80° C., and the reaction was carried out for 8 hours. After the reaction was finished, cool and filter with a diatomaceous earth / silica gel funnel, and the filtrate was distilled under reduced pressure to remove the solvent, and the residue obtained was recrystallized in toluene and dried to obtain 22.93g (41.5mmol) of the intermediate (B-1 ), the yield is 83%.

Embodiment 2

[0095] Embodiment 2: the preparation of compound HT47

[0096]

[0097] (1) Under an argon atmosphere, dissolve 22.10g (40mmol) of intermediate B-1, 5.73g (40mmol) of 1-naphthylamine (compound M-1), and 7.69g (80mmol) of sodium tert-butoxide in 400ml of dehydrated toluene , add 0.18g (0.8mmol) of palladium acetate and 0.16g (0.8mmol) of triphenylphosphine under stirring, and react at 80°C for 8 hours. After cooling, filter through a diatomaceous earth / silica gel funnel, and the filtrate removes the organic solvent by distillation under reduced pressure, and the resulting residue is recrystallized in toluene and dried to obtain 21.64g (35.2mmol) of intermediate C-1 with a yield of 88 %.

[0098] (2) Under an argon atmosphere, 18.47g (30mmol) of intermediate C-1, 10.90g (30mmol) of bromide N-1, 5.77g (60mmol) of sodium tert-butoxide were dissolved in 300ml of dehydrated toluene, 0.14 g (0.6 mmol) of palladium acetate and 0.12 g (0.6 mmol) of triphenylphosphine were added unde...

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Abstract

The invention provides an arylamine derivative and an organic electroluminescent device thereof and relates to the technical field of organic photoelectric materials. The arylamine derivative has theadvantages of simple preparation method, easily obtained raw materials, very good stability, very good film-forming property and good hole transporting ability; and meanwhile, the arylamine derivativehas an appropriate highest occupied molecular orbital energy level (HOMO) and a first triplet energy level (T1) value and can be applied to the OLED device as a luminescence assisting layer to realize balance of charges in a luminescent layer and prevent exciton from diffusing to one side of a hole transporting layer. Therefore, the arylamine derivative provided by the invention is applied to theOLED device as the hole transporting layer and the luminescence assisting layer and has the advantages that the luminescence efficiency of the device can be obviously enhanced, the color purity of the device can be obviously enhanced, the service life of the device can be effectively prolonged, the driving voltage of the device can also be effectively reduced, and the arylamine derivative is an OLED material with excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine derivative and an organic electroluminescent device. Background technique [0002] Organic light-emitting diode (OLED) is a double-injection light-emitting device. Its structure is like a sandwich structure. It is composed of an indium tin oxide anode, a metal cathode and an organic layer between the two. Holes are injected from the anode side, and electrons are injected from the cathode side. The two interact in the light-emitting layer of the organic layer to form excitons. Light energy of organic semiconductor material molecules. The organic layer contains luminescent materials, hole transport materials, electron transport materials and the like. Among them, the function of the hole transport material is mainly to inject and transport holes, and has a high hole mobility (hole mobility), which is beneficial to the injection and transp...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C211/56C07C211/58C07C211/61C07D307/77C07D307/91C07D307/93C07D307/94C07D333/76C07D333/78C07D409/12C07D493/04C07D495/04H01L51/54
CPCC07C211/54C07C211/56C07C211/58C07C211/61C07D307/77C07D307/91C07D307/93C07D307/94C07D333/76C07D333/78C07D409/12C07D493/04C07D495/04H10K85/624H10K85/615H10K85/631H10K85/636H10K85/633H10K85/6576H10K85/6574
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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