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Fluoreno-aza-naphthalene derivative, synthesis method and electronic device thereof

A technology for electronic devices and aziridines, which is applied in the field of electronic devices, fluorenazine derivatives and their synthesis, and achieves the effects of simple preparation methods, broad industrialization prospects, and reduced driving voltage

Pending Publication Date: 2020-08-18
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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  • Fluoreno-aza-naphthalene derivative, synthesis method and electronic device thereof
  • Fluoreno-aza-naphthalene derivative, synthesis method and electronic device thereof
  • Fluoreno-aza-naphthalene derivative, synthesis method and electronic device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] Embodiment 1: the synthesis of compound 2-15

[0136] (Synthesis of intermediate M1)

[0137] The synthetic route of intermediate M1 is as follows:

[0138]

[0139] P-bromobenzohydrazide (4.3g, 20mmol), ninhydrin (3.6g, 20mmol), ammonium acetate (12.0g, 90mmol) and 120mL acetic acid were successively added into a 250mL single-necked flask, and the reaction was stirred under reflux 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, 3.9 g of a light yellow solid was obtained, with a yield of 58%. MS (EI): m / z: 336.58 [M + ]. Anal.calcdforC 16 h 8 BrN 3 O (%): C 56.83, H 2.38, N 12.43; found: C 56.75, H 2.35, N 12.40.

[0140] (Synthesis of Intermediate M2)

[0141] The synthetic route of intermediate M2 is as foll...

Embodiment 2

[0156] Embodiment 2: the synthesis of compound 2-41

[0157] (Synthesis of compound 2-41)

[0158] The synthetic route of compound 2-41 is as follows:

[0159]

[0160] In a 250mL two-necked flask, add 9.2g (23.0mmol) M4, 5.2g (29.0mmol) carbazole, 3.0g (29.0mmol) sodium tert-butoxide, 0.1g (0.3mmol) tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) of tris(dibenzylideneacetone)dipalladium, after degassing the reaction system, under the protection of nitrogen, add 150mL of toluene, stir and heat 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 10.3 g of a white solid with a yield of 92%. MS (EI): m / z 488....

Embodiment 3

[0161] Embodiment 3: the synthesis of compound 2-1

[0162] (Synthesis of compound 2-1)

[0163] Compound 2-1 synthetic route is as follows:

[0164]

[0165] In a 250mL two-necked flask, add 9.2g (23.0mmol) M4, 5.2g (29.0mmol) diphenylamine, 3.0g (29.0mmol) sodium tert-butoxide, 0.1g (0.3mmol) tri-tert-butylphosphine tetrafluoroborate, 0.27g (0.3mmol) of tris(dibenzylideneacetone)dipalladium, after degassing the reaction system, under the protection of nitrogen, add 150mL of toluene, stir and heat 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 10.3 g of a white solid with a yield of 92%. MS (EI): m / z 490.43 [M+...

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PUM

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Abstract

The invention relates to the technical field of organic photoelectric materials, and specifically relates to a fluorene aza-naphthalene derivative, a synthesis method thereof, and an electronic devicecontaining the fluorene aza-naphthalene derivative, the fluorene aza-naphthalene derivative being represented by general formula (1), in which Y represents one or more of C (R1) 2, NR1, O, S, SO2, P(= O) R1, Si (R1) 2, Ge (R1) 2, or a single bond. According to the fluoreno-aza-naphthalene derivative disclosed by the invention, a fluoreno-aza-naphthalene rigid structure is introduced, so that theobtained fluoreno-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 fluoreno-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 driving voltage, improve efficiency and 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 a fluorenazinaphthalene derivative, a synthesis method thereof, and an electronic device containing the fluorenazanaphthalene derivative. 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 i...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C07F5/02C07F7/08C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07D471/04C07D519/00C07F5/027C07F7/0812C09K11/06C09K2211/1014C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/622H10K85/631H10K85/322H10K85/654H10K85/6576H10K85/6574H10K85/657H10K10/46H10K85/40H10K30/00H10K85/6572H10K50/18H10K50/16H10K50/15H10K50/17H10K50/11Y02E10/549
Inventor 崔林松朱向东张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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