Aza-naphthalene derivative, synthesis method and electronic device thereof

A technology for electronic devices and derivatives is applied in the fields of electronic devices, azanaphthalene derivatives and their synthesis, and achieves the effects of excellent electron transport performance, low driving voltage and simple preparation method.

Pending Publication Date: 2020-08-14
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, the future direction of organic electroluminescent devices is to develop high-efficiency, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems

Method used

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  • Aza-naphthalene derivative, synthesis method and electronic device thereof
  • Aza-naphthalene derivative, synthesis method and electronic device thereof
  • Aza-naphthalene derivative, synthesis method and electronic device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Embodiment 1: the synthesis of compound 1-31

[0123] (Synthesis of intermediate M1)

[0124] The synthetic route of intermediate M1 is as follows:

[0125]

[0126] Add benzohydrazide (2.3g, 20mmol), 2-bromoacetophenone (2.0g, 10mmol), sodium acetate (2.0g, 15mmol) and 120mL mixed solvent (ethanol: acetic acid=7: 3 (V / V)), reflux and stirred for 12 hours. After the reaction was complete, the solid was collected by suction filtration and washed with a small amount of absolute ethanol. The crude product was further purified by column chromatography (petroleum ether:dichloromethane=3:1 (V / V)). The solvent was evaporated, and after drying, 1.3 g of light yellow solid was obtained with a yield of 58%. MS (EI): m / z: 233.58 [M + ]. Anal.calcd for C 15 h 11 N 3 (%): C 77.23, H 4.75, N 18.01; found: C 77.10, H 4.70, N 17.90. (Synthesis of Intermediate M3)

[0127] The synthetic route of intermediate M2 is as follows:

[0128]

[0129] Under an argon atmosphere...

Embodiment 2

[0134] Embodiment 2: the synthesis of compound 1-8

[0135] (Synthesis of Compounds 1-8)

[0136] Compound 1-8 synthetic route is as follows:

[0137]

[0138] In a 250mL two-necked flask, 7.2g (23.0mmol) M2, 9.6g (29.0mmol) 5,7-dihydro-5-phenylindolo[2,3-B]carbazole, 3.0g (29.0mmol) ) sodium tert-butoxide, 0.1g (0.3mmol) tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) tris(dibenzylideneacetone) dipalladium, after degassing the reaction system, under the protection of nitrogen, add 150mL of toluene was stirred and heated to reflux for 12 hours. After the reaction was complete, the system was cooled to room temperature, filtered under reduced pressure, and the filter residue was washed with a large amount of dichloromethane, and the filtrate was concentrated to obtain a crude product, which was eluted with petroleum ether:dichloromethane=2:3 (volume ratio) The reagent was separated and purified on a silica gel column to obtain 13.0 g of a white solid with a yie...

Embodiment 3

[0139] Embodiment 3: the synthesis of compound 1-14

[0140] (Synthesis of Compound 1-14)

[0141] Compound 1-14 synthetic route is as follows:

[0142]

[0143] Under nitrogen, add 13.8g (47.8mmol) triphenylamine 4-borate, 8.4g (79.6mmol) anhydrous sodium carbonate, 12.7g (39.8mmol) M2, 470.8mg (4.8mmol) ) tetrakis(triphenylphosphine palladium) and 100 mL mixed solvent (toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux and reacted overnight under reflux. After the reaction was completed, the heating was stopped, and the reaction system was cooled to room temperature by itself. The reaction solution was poured into about 200 mL of water, and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 3:2 (V / V)) to obtain a red solid 17.7g, yield 84%. MS (EI): m / z: ...

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Abstract

The invention relates to the technical field of organic photoelectric materials. The present invention relates to an aza-naphthalene derivative, a synthesis method thereof, and an electronic device containing the aza-naphthalene derivative. The aza-naphthalene derivative is represented by a general formula (1), wherein L1 to L3 each independently represents one or more of a single bond, a carbonylgroup, an aromatic hydrocarbon group having 6 to 18 carbon atoms, and an aromatic heterocyclic group having 5 to 18 carbon atoms. According to the aza-naphthalene derivative disclosed by the invention, an aza-naphthalene rigid structure is introduced, so that the obtained aza-naphthalene derivative is excellent in film-forming property and thermal stability, and can be used for preparing an organic light-emitting device, an organic field effect transistor and an organic solar cell. In addition, the aza-naphthalene derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, improve the brightness, prolong the service life and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to azinaphthalene derivatives, a synthesis method thereof, and an electronic device containing azanaphthalene derivatives. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode, a metal cathode, and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. I...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/50H01L51/54H01L51/05H01L51/30H01L51/42H01L51/46
CPCC07D471/04C07D519/00C09K11/06C09K2211/1029C09K2211/1059C09K2211/1044C09K2211/1014C09K2211/1033H10K85/657H10K85/6572H10K10/00H10K30/00H10K50/11H10K50/171H10K50/18H10K50/15H10K50/16H10K50/17Y02E10/549
Inventor 崔林松朱向东张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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