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10-azaanthracene derivative, and preparation method and applications thereof

A technology of anthracene derivatives and fused heterocycles, which is applied in the field of 10-nitroanthracene derivatives and its preparation, can solve the problems of increasing material cost budget and OLED device manufacturing cost, so as to improve external quantum efficiency and transmittance , cost-saving effect

Active Publication Date: 2017-02-15
CHANGCHUN HYPERIONS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation of an additional layer of CPL material not only needs to increase the cost budget of the material, but also needs to add a separate evaporation chamber, which increases the preparation cost of OLED devices.

Method used

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  • 10-azaanthracene derivative, and preparation method and applications thereof
  • 10-azaanthracene derivative, and preparation method and applications thereof
  • 10-azaanthracene derivative, and preparation method and applications thereof

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preparation example Construction

[0045] The present invention also provides a preparation method of the 10-aza(hetero)anthracene derivative, including:

[0046] The compound represented by formula (A) and the compound represented by formula (B) undergo a coupling reaction under the protection of nitrogen to obtain the 10-aza(hetero)anthracene derivative represented by formula (I):

[0047]

[0048] Wherein, X is a substituted or unsubstituted C6-C60 arylamino group or a substituted or unsubstituted C6-C60 fused heterocyclic ring.

[0049] According to the present invention, the intermediate represented by formula (A) is prepared according to the following method:

[0050] (1) reacting 4,5-dibromo-2-nitrobenzaldehyde represented by formula A-1 with 4-bromocyclohexanol represented by C to obtain a compound represented by formula A-2;

[0051] (2) Reacting the compound represented by formula A-2 with elemental bromine to obtain the intermediate represented by formula (A).

[0052]

[0053] In the present invention, the rea...

Embodiment 1

[0061] Example 1: Preparation of Intermediate A

[0062] (1) Synthesis of compound A-2: 154g (0.5mol) of 4,5-dibromo-2-nitrobenzaldehyde (compound A-1), 89g (0.5mol) of 4- Bromocyclohexanol (compound C), 28g (0.05mol) of 1,1'-bis(diphenylphosphine)ferrocene, and 1L of chlorobenzene, then the temperature was raised to 150°C, and the reaction was fully stirred for 24 hours. After the reaction, it was filtered with Celite, washed with toluene and hexane, concentrated, and purified by column chromatography to obtain 73 g of compound A-2 with a yield of 35%. Mass spectrum m / z: 415.96 (calculated value: 415.91). Theoretical element content (%) C 13 H 6 Br 3 N: C, 37.54; H, 1.45; Br, 57.64; N, 3.37. Measured element content (%): C, 37.45; H, 1.37; Br, 57.58; N, 3.15. The above results confirm that the obtained product is the target product.

[0063] (2) Synthesis of Intermediate A: Add 111g (0.83mol) of anhydrous aluminum trichloride to a three-necked flask, add 166g (0.4mol) of compo...

Embodiment 2

[0064] Example 2: Synthesis of compound TM1

[0065] Add 494mg (1mmol) of Intermediate A and 231mg (0.2mmol) of tetrakis(triphenylphosphine) palladium mixture to 10ml of toluene with removal of air, 2 Under protection, heat the system to 60°C and stir for 5 minutes. 1272 mg (4.4 mmol) of triphenylamine-4-boronic acid, 2.5 ml of de-aired ethanol, and 5 ml of de-aired 2M sodium carbonate aqueous solution were sequentially added to the system, and stirred at 80°C for 24 hours. The reaction system was poured into a large amount of water and extracted with dichloromethane. The organic layer was washed sequentially with saturated brine and water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure. After the remaining solid was purified by column chromatography (hexane / dichloromethane=4:4, V / V), it was recrystallized from a mixed solution of hexane / chloroform to obtain 829 mg (0.72 mmol) of compound TM1 with a yield of 72 %. Mass spectrum m / z: 1152.46 (calcu...

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Abstract

The invention provides a 10-azaanthracene derivative, and a preparation method and applications thereof, and belongs to the technical field of organic photoelectric material. The 10-azaanthracene derivative possesses higher light extraction efficiency via optimization on molecular structure design, can be used for preparing organic electroluminescence devices, especially can be taken as a light extraction material in the organic electroluminescence devices, and is capable of increasing luminous efficiency of OLED devices effectively, and obtaining OLED devices better than conventional OLED devices. The invention also provides a preparation method of the 10-azaanthracene derivative. The preparation method is simple; and raw materials are easily available.

Description

Technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a 10-aza (hetero)anthracene derivative, and a preparation method and application thereof. Background technique [0002] The research of organic electroluminescence phenomenon began in the 1960s. In 1963, Pope of New York University in the United States observed electroluminescence on anthracene single crystals for the first time; in 1987, Tang et al. of Kodak Company reported the use of 8-hydroxyquinoline Aluminum and aromatic diamines with hole transport properties are made into high-quality films and made into organic light-emitting devices; in 1990, Friend et al. reported the phenomenon of polymer electroluminescence at low voltage; in 1998, Forrest et al., Princeton University, USA Discovered the phenomenon of phosphorescent light emission; since 2000, OLED has received great attention from the industry and has begun to enter the industrialization stage. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D401/14H01L51/52H01L51/54
CPCC07D219/02C07D401/14H10K85/633H10K85/631H10K85/6572H10K50/85
Inventor 周雯庭郭建华
Owner CHANGCHUN HYPERIONS TECH CO LTD
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