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Spirobifluorene Derivatives and Their Applications in the Field of Organic Electroluminescence

A technology of spirobifluorene and compounds, which is applied to spirobifluorene derivatives and its application in the field of organic electroluminescence, can solve the problems of limited application and low triplet energy level of molecules, and achieve the purpose of suppressing energy consumption, The effect of long-life device performance and high stability

Active Publication Date: 2021-03-19
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the derivatives of the 2-position and 4-position generally have a large degree of conjugation, and the triplet energy level of the molecule is low, which greatly limits its application in blue organic electroluminescent devices.

Method used

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  • Spirobifluorene Derivatives and Their Applications in the Field of Organic Electroluminescence
  • Spirobifluorene Derivatives and Their Applications in the Field of Organic Electroluminescence
  • Spirobifluorene Derivatives and Their Applications in the Field of Organic Electroluminescence

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preparation example Construction

[0073]

[0074] Compounds according to the present invention can be prepared by synthetic procedures known to those of ordinary skill in the art, such as bromination, Suzuki coupling, Hartwig-Buchwald coupling, and the like.

[0075] The synthesis of the compounds of the present invention usually starts with 3- and / or 6-functionalized spirobifluorene derivatives, followed by the introduction of the group -L by metal-catalyzed coupling reactions such as Suzuki coupling 1 -R 1 and / or -L 2 -R 2 .

[0076] In a preferred embodiment of the present invention, the spirobifluorene derivative is a compound functionalized with a boronic acid derivative, and the group -L 1 -R 1 and / or -L 2 -R 2 Derived from halogen-functionalized compounds. In another preferred embodiment of the present invention, the spirobifluorene derivative is a halogen-functional compound, and the group -L 1 -R 1 and / or -L 2 -R 2 Compounds derived from functionalization of boronic acid derivatives.

[...

preparation example

[0092] Synthesis of Intermediate 1:

[0093] The structural formula and synthetic route of intermediate 1 are shown in the following formula:

[0094]

[0095]The preparation method of the compound of formula M1 is: in the 250 mL there-necked flask equipped with thermometer, dropping funnel and mechanical stirring, add 10.0g (36.21mmol) 2-amino-4'-bromo-benzophenone and 80mL water, Slowly add 5.0g, 98% (50mmol) concentrated sulfuric acid dropwise under stirring, stir for 30 minutes, cool to 0°C, add dropwise a solution of 1.5g (21mmol) sodium nitrite dissolved in 5mL water, after the dropwise addition, keep the After 30 minutes, the temperature was slowly raised to 60°C. After the bubbles were completely released, it was cooled to room temperature and filtered to obtain a light yellow crystalline solid. The solid was separated by column chromatography (350 mesh silica gel, the eluent was petroleum ether:dichloromethane=20:1 (V / V)), the solvent was evaporated, and after dry...

preparation example 1

[0098] Preparation Example 1: Synthesis of Compound 1-75

[0099] The structural formula and synthetic route of compound 1-75 are shown in the following formula:

[0100]

[0101] In a 200mL Schlenk bottle, add 1.50g (4.16mmol) of 3-boronic acid-9,9' spirobifluorene, 0.47g (2.08mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine ), tetrakis(triphenylphosphine)palladium 0.26g (0.23 mmol), anhydrous potassium carbonate 1.77g (12.8mmol), tetrahydrofuran 50mL, water 8mL, under the protection of argon gas, stirred and reacted at 70°C for 30 hours, and the reaction was completed. Evaporate the solvent, dissolve the residue with 50mL dichloromethane and 50mL water, wash with water, separate the organic layer, extract the water layer twice with 15mL dichloromethane, combine the organic layers, wash twice with 50mL water until neutral, evaporate the solvent Finally, the residue was separated by column chromatography (silica gel was 350 mesh, and the eluent was petroleum ether: chloroform...

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Abstract

The invention relates to spirobifluorene derivatives and their application in the field of organic electroluminescence. The compound of the present invention can be used in electronic devices, especially organic electroluminescent devices, organic field effect transistors, and organic solar cells, and is especially suitable for preparing light-emitting host materials, exciton blocking materials or electron transport materials of organic electroluminescent devices. In addition, the invention also relates to electronic devices comprising said compounds.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to the use of meta-substituted spirobifluorene compounds and the compounds of the present invention in electronic devices, especially in organic electroluminescent devices, organic field effect transistors, and organic solar cells, especially in organic electroluminescent devices. It is used as a luminescent host material, an exciton blocking material or an electron transport material in a luminescent device, and also relates to an electronic device containing the compound. Background technique [0002] Luminescent materials that meet various information display requirements are developing rapidly in today's information age. Luminescent materials are mainly divided into inorganic and organic [0003] Two types, compared with inorganic materials, organic materials have relatively higher luminous efficiency and wider range of luminous color selection, and have t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/72C07C22/08C07C49/792C07D209/86C07D235/18C07D251/26C07D271/107C07D307/91C07D333/76C07D403/04C07D403/10C07D403/14C07D405/04C07D405/10C07D409/04C07D409/10C07D409/14C09K11/06H01L51/54
CPCC09K11/06C07C13/72C07C22/08C07C49/792C07D209/86C07D235/18C07D251/26C07D271/107C07D307/91C07D333/76C07D403/04C07D403/10C07D403/14C07D405/04C07D405/10C07D409/04C07D409/10C07D409/14C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1044C09K2211/1011H10K85/624H10K85/626H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572Y02E10/549
Inventor 陈华王慧
Owner 维思普新材料(苏州)有限公司
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