Spirobifluorene derivative and application of spirobifluorene derivative in field of organic electroluminescence

A spirobifluorene and compound technology, which is applied to spirobifluorene derivatives and their application in the field of organic electroluminescence, can solve the problems of limited application, low molecular triplet energy level, etc. The effect of long-life device performance and high stability

Active Publication Date: 2017-09-08
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 triple

Method used

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  • Spirobifluorene derivative and application of spirobifluorene derivative in field of organic electroluminescence
  • Spirobifluorene derivative and application of spirobifluorene derivative in field of organic electroluminescence
  • Spirobifluorene derivative and application of spirobifluorene derivative in field of organic electroluminescence

Examples

Experimental program
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Example Embodiment

[0073]

[0074] The 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 from the spirobifluorene derivatives functionalized at the 3 and / or 6 positions, and then the group -L is introduced through a metal-catalyzed coupling reaction 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-functionalized compound, and the group -L 1 -R 1 And / or -L 2 -R 2 A compound derived from the functionalization of a boric acid deriv...

Example Embodiment

[0091] 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: add 10.0g (36.21mmol) 2-amino-4'-bromo-benzophenone and 80mL water into a 250 mL three-necked flask equipped with a thermometer, dropping funnel and mechanical stirring. Slowly add 5.0g, 98% (50mmol) concentrated sulfuric acid under stirring, stir for 30 minutes, cool to 0℃, dropwise add 1.5g (21mmol) sodium nitrite dissolved in 5mL water solution, after the addition, keep this 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 pale yellow crystalline solid. The solid is separated by column chromatography (350 mesh silica gel, the eluent is petroleum ether: dichloromethane = 20:1 (V / V)), the solvent is evaporated, and after dryin...

Example Embodiment

[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 ), 0.26 g (0.23 mmol) of tetrakis(triphenylphosphine) palladium, 1.77 g (12.8 mmol) of anhydrous potassium carbonate, 50 mL of tetrahydrofuran, 8 mL of water, under the protection of argon, the reaction was stirred at 70°C for 30 hours, and the reaction was completed. Evaporate the solvent, dissolve the residue with 50mL of dichloromethane and 50mL of water, wash with water, separate the organic layer, extract the aqueous layer twice with 15mL of dichloromethane, combine the organic layers, wash twice with 50mL of water to neutral, evaporate the solvent Afterwards, the residue was separated by column chromatography (silica gel is 350 mesh, the eluent is petroleu...

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Abstract

The invention relates to a spirobifluorene derivative and application of the spirobifluorene derivative in the field of organic electroluminescence. A compound provided by the invention can be used in electronic devices, particularly organic electroluminescent devices, organic field-effect transistors and organic solar cells and is particularly suitable for a light-emitting host material, an exciton blocking material or an electron transport material for preparing the organic electroluminescent devices. In addition, the invention also relates to the electronic device comprising the compound.

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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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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