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3,4-diazaspirofluorene derivative and synthetic method thereof and electronic device containing 3,4-diazaspirofluorene derivative

A technology of fluorene derivatives and diazaspiro, which is applied in the field of organic optoelectronic materials to achieve good film-forming properties and thermal stability, good application effects, high electron injection and movement rates

Pending Publication Date: 2020-02-11
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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  • 3,4-diazaspirofluorene derivative and synthetic method thereof and electronic device containing 3,4-diazaspirofluorene derivative
  • 3,4-diazaspirofluorene derivative and synthetic method thereof and electronic device containing 3,4-diazaspirofluorene derivative
  • 3,4-diazaspirofluorene derivative and synthetic method thereof and electronic device containing 3,4-diazaspirofluorene derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] Embodiment 1: the synthesis of compound 15

[0157] (Synthesis of Intermediate 1-1)

[0158] The synthetic route of intermediate 1-1 is as follows:

[0159]

[0160] Under the protection of nitrogen, 2-bromobiphenyl (2.0 g, 8.9 mmol) and 150 mL of anhydrous tetrahydrofuran were added into a dry and clean 250 mL three-necked flask, and stirred and dissolved at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was completed. Then 3-(4-bromophenyl)-5H-indolo[1,2-c]pyridazin-5-one (2.7g, 8.1mmol) was added in one go, and the cooling bath was removed after the addition, and the reaction was spontaneous Warm to room temperature and continue stirring overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0161] The above white solid was transferred to a 250 mL...

Embodiment 2

[0166] Embodiment 2: the synthesis of compound 99

[0167] (Synthesis of Intermediate 1-2)

[0168] The synthetic route of intermediate 1-2 is shown below:

[0169]

[0170] Under the protection of nitrogen, 2-bromotriphenylamine (2.9 g, 8.9 mmol) and 150 mL of anhydrous tetrahydrofuran were added into a dry and clean 250 mL three-necked flask, and stirred and dissolved at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was complete. Then 3-(4-bromophenyl)-5H-indolo[1,2-c]pyridazin-5-one (2.7g, 8.1mmol) was added in one go, and the cooling bath was removed after the addition, and the reaction was spontaneous Warm to room temperature and continue stirring overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0171] The above white solid was transferred to a ...

Embodiment 3

[0180] Embodiment 3: the synthesis of compound 337

[0181] (Synthesis of Intermediates 1-4)

[0182] The synthetic routes of intermediates 1-4 are shown below:

[0183]

[0184] Under the protection of nitrogen, 1-bromo-8-phenylnaphthalene (2.5 g, 8.9 mmol) and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-necked flask, and stirred to dissolve at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was completed. Then 3-(4-bromophenyl)-5H-indolo[1,2-c]pyridazin-5-one (2.7g, 8.1mmol) was added in one go, and the cooling bath was removed after the addition, and the reaction was spontaneous Warm to room temperature and continue stirring overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0185] The above white solid was transferr...

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Abstract

The invention relates to the technical field of organic photoelectric materials, specifically to a 3,4-diazaspirofluorene derivative and a synthetic method thereof, and an electronic device containingthe 3,4-diazaspirofluorene derivative. The 3,4-diazaspirofluorene derivative is as represented by a general formula (1) which is described in the specification. In the general formula (1), L1 to L3 each independently represent one or more selected from a group consisting of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, and an aromatic heterocyclic group having 5 to 18 carbon atoms. According to the 3,4-diazaspirofluorene derivative disclosed by the invention, a 3,4-diazaspirofluorenone rigid structure is introduced, so the obtained 3, 4-diazaspirofluorene 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 solarcell. Furthermore, the 3,4-diazaspirofluorene 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, ahole blocking layer or an electron transport layer, and can reduce driving voltage, improve efficiency, brightness, prolong service life and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to 3,4-diazaspirofluorene derivatives, a synthesis method thereof and electronic devices containing 3,4-diazaspirofluorene 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 inject...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D237/26C07D401/10C07D413/10C07D417/10C07D491/048C07D495/04C07D487/04C07F9/6509C07F5/02C07F7/10C07D471/04C07D403/04C07D401/04C07D413/04C07D417/04C07D401/14C07D471/10C07D519/00C07F9/6561C07D498/20C07D471/20C07D513/20C07F9/6584C07D491/107C07D495/10C09K11/06H01L51/50H01L51/54
CPCC07D403/10C07D237/26C07D401/10C07D413/10C07D417/10C07D491/048C07D495/04C07D487/04C07F9/650947C07F5/027C07F7/0812C07D471/04C07D403/04C07D401/04C07D413/04C07D417/04C07D401/14C07D471/10C07D519/00C07F9/65615C07F7/0816C07D498/20C07D471/20C07D513/20C07F9/6584C07D491/107C07D495/10C09K11/06C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1088C09K2211/1029C09K2211/1092C09K2211/104H10K85/622H10K85/636H10K85/633H10K85/631H10K85/657H10K85/6572H10K50/18H10K50/15H10K50/16H10K50/17H10K50/11
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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