N-containing fused ring compound and application thereof in organic electronic device

A technology of organic compounds and ring atoms, applied in the field of electroluminescent materials, can solve the problems of stability and insufficient rigidity of luminescent host materials, and achieve the effects of improving luminous efficiency and life, reducing roll-off and improving rigidity

Active Publication Date: 2021-05-11
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In view of the above deficiencies in the prior art, the object of the present invention is to provide a kind of N-containing fused ring compound, a mixture containing it, a composition, an organic electronic device and its application, aiming at solving the problem of insufficient stability and rigidity of the existing luminescent host materials The problem

Method used

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  • N-containing fused ring compound and application thereof in organic electronic device
  • N-containing fused ring compound and application thereof in organic electronic device
  • N-containing fused ring compound and application thereof in organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] The synthetic route of compound (1) is as follows:

[0168]

[0169]

[0170] Synthesis of intermediate 3:

[0171] Under nitrogen protection atmosphere, in a dry three-necked flask, add 1mmol of intermediate 1 and 2.1mmol of intermediate 2 respectively, pour 100ml of DMSO as a solvent, add dry K 2 CO 3 As a base, react at 120°C for 8 hours, monitor the reaction by TLC, after the reaction is complete, cool the reaction solution to room temperature, add water and dichloromethane in sequence, wash the reaction solution with water for several times, and extract the aqueous phase with dichloromethane Multiple times, the organic phases were combined and washed with anhydrous Na 2 CO 3 Dry, filter, and spin dry the reaction solution to obtain a crude product, which is recrystallized from ethyl acetate to obtain 0.78 mmol of intermediate 3, with a reaction yield of 78%, MS (ASAP) = 960.7.

[0172] Synthesis of intermediate 4:

[0173] Under nitrogen protection atmos...

Embodiment 2

[0176]

[0177] The synthetic route of compound (2) is as follows:

[0178]

[0179] Synthesis of intermediate 3:

[0180] The synthesis method is exactly the same as the synthesis method of intermediate 3 in compound (1), except that the raw material is changed from bromocarbazole to bromonaphthalene carbazole (intermediate 2), and the yield is 82.1%. MS (ASAP) = 1127.1.

[0181] Synthesis of Intermediate 4:

[0182]The synthesis method is exactly the same as the synthesis method of intermediate 4 in compound (1), and the yield is 30.5%. MS (ASAP) = 807.5.

[0183] Synthesis of intermediate 5:

[0184] In a 1000ml bottle, add intermediate 4 (57mmol), reduced iron powder (239.4mmol), ammonium chloride (239.4mmol) and 10ml of concentrated hydrochloric acid and 800ml of MeOH / THF / H 2 O mixed solvents were heated to 70° C. to react in the air environment, and the reaction was tracked by TLC. After the reaction is complete, cool to room temperature, remove the solvent i...

Embodiment 3

[0188]

[0189] The synthetic route of compound (3) is as follows:

[0190]

[0191] Synthesis of Intermediate 3:

[0192] The synthesis method is exactly the same as the synthesis method of intermediate 3 in compound (1), the solvent is changed from DMSO to DMF, and the yield is 83.4%. MS (ASAP) = 1161.0.

[0193] Synthesis of Intermediate 4:

[0194] The synthesis method is exactly the same as the synthesis method of intermediate 4 in compound (1), and the yield is 28.5%. MS (ASAP) = 841.4.

[0195] Synthesis of compound (3):

[0196] The synthesis method is exactly the same as that in compound (1), and the yield is about 31.2%. MS (ASAP) = 612.5.

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Abstract

The invention relates to an N-containing fused ring compound, which has a structure as shown in a general formula (1). The organic compound is high in rigidity and high in material stability, can be used as a main body material or a luminescent material to be applied to an organic electronic device, and is convenient for improving the luminous efficiency and prolonging the service life of the organic electronic device; and a solution for light-emitting device with low manufacturing cost, high efficiency, long service life and low roll-off is provided.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on November 6, 2019, with the application number 201911073605.2, and the invention title is "A N-containing fused ring compound and its application in organic electronic devices", the entire content Incorporated in this application by reference. technical field [0002] The invention relates to the field of electroluminescent materials, in particular to an N-containing condensed ring compound and its application in organic electronic devices. Background technique [0003] Due to the diversity of organic semiconductor materials in synthesis, relatively low fabrication cost, and excellent optical and electrical properties, organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat panel displays and lighting. [0004] In order to improve the luminous efficiency of organic light-emitting diodes, various light-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22C07D487/22C07D491/22C07F5/02C07F9/6584H01L51/54H01L51/50
CPCC07F5/027C07D487/22C07F9/6584C07D471/22C07D491/22H10K85/654H10K85/6572H10K85/657H10K50/11Y02E10/549
Inventor 黄宏张静
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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