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Hexafluorenylbenzene derivative and application thereof to organic photoelectric functional material

A technology of hexafluorenylbenzene and derivatives is applied in the field of organic optoelectronic functional materials and device preparation, which can solve the problems of low glass transition temperature and decreased stability, and achieve the effect of high-efficiency electroluminescence performance.

Active Publication Date: 2012-12-26
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the low glass transition temperature of ordinary linear aromatic amine transport materials, it often leads to a decrease in the stability of the device after a period of time (Chem. Phys. Lett., 2003, 371, 700)

Method used

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  • Hexafluorenylbenzene derivative and application thereof to organic photoelectric functional material
  • Hexafluorenylbenzene derivative and application thereof to organic photoelectric functional material
  • Hexafluorenylbenzene derivative and application thereof to organic photoelectric functional material

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preparation example Construction

[0030] Compound sample preparation

[0031] The hexafluorenylbenzene derivatives of the present invention can be prepared by Suzuki, Sonagashira coupling and other reactions to prepare substituted difluorene acetylenes, and then through dicobalt octacarbonyl (Co 2 (CO) 8 ) Catalyzed [2+2+2] cycloaddition reaction prepared. The raw materials used in this embodiment are known compounds, which can be purchased in the market, or can be synthesized by methods known in the art.

Embodiment 1

[0032] Example 1: Preparation of hexa-(9,9-di-n-hexylfluorene)benzene (2), the synthetic route is as follows

[0033]

[0034] (1) Preparation of hexa-(9,9-di-n-hexylfluorene)benzene

[0035] In the 100ml flask, add difluorene acetylene, weigh octacarbonyl dicobalt (Co 2 (CO) 8 ), add 80ml of anhydrous and oxygen-free 1,4-dioxane, protect with argon, stir and react at 120°C for 24 hours, pour into water after cooling and filter, the obtained solid is dissolved in chloroform, dried with petroleum ether : Chloroform=10:1 is the column separation of the eluent, and the resulting product is recrystallized with petroleum ether to obtain a white needle-like solid with a yield of 92%. Time-of-flight mass spectrometry: 2072.7. Elemental analysis: theoretical value C: 90.37%, H: 9.63%. Experimental value C: 90.05%, H: 9.44%.

Embodiment 2

[0036] Example 2: Preparation of hexa-(9,9-di-p-tolylfluorene)benzene (3), the synthetic route is as follows

[0037]

[0038] (1) Preparation of hexa-(9,9-di-p-tolylfluorene)benzene (3)

[0039] Referring to the preparation method of hexa-(9,9-n-hexylfluorene)benzene in Example 1, using petroleum ether: chloroform as the eluent = 4:1 (v / v) to pass through the column to obtain a white solid with a yield of 83%. Time-of-flight mass spectrum (m / z): 2144.0. Elemental analysis: theoretical value C: 94.08%, H: 5.92%, experimental value C: 93.86%, H: 5.81%.

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Abstract

The invention discloses a star-shaped compound which uses hexafluorenylbenzene as a skeleton. Six functionalized alkylaryl and heterocycle-substituted fluorine are simultaneously connected onto a benzene ring. The synthesis method of the star-shaped compound is simple and feasible and can be widely used. A hexafluorenylbenzene derivative provided by the invention can be used as luminescent layers and hole transport layers for making electroluminescent devices, has the advantages of high efficiency, high brightness and high spectrum stability, and can be widely used in the field of organic electroluminescence.

Description

technical field [0001] The invention relates to a hexafluorenylbenzene derivative and its application in organic photoelectric functional materials, belonging to the technical field of organic photoelectric functional materials and device preparation. Background technique [0002] The star compound consists of a core and several functionalized branches. Due to its unique structure, it combines the advantages of both small molecules and macromolecules, such as high quantum yield, high thermal stability and film formation, and reproducible preparation , and its material properties can also be precisely tuned by changing the molecular structure. Due to these characteristics, star compounds have attracted extensive attention in various fields in recent years. (Chem.Soc.Rev.2010,39,2695.) [0003] Among the current organic optoelectronic functional materials, polyfluorene and its derivatives have attracted widespread attention. They have high fluorescence quantum yield and good...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/567C07D333/08C07D209/86C07C211/61C07D213/06C09K11/06H01L51/54
Inventor 杨楚罗邹洋尹校君秦金贵
Owner WUHAN UNIV
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