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Thiphenanthridinone derivative, synthetic method thereof and electronic device containing thiaphenanthridinone derivative

A technology of thiaphenanthridone and heterophenanthridone is applied in the fields of electronic devices, thiaphenanthridone derivatives and synthesis thereof, and achieves the effects of easy availability of raw materials, enhanced durability and wide industrialization prospects

Inactive Publication Date: 2020-01-17
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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  • Thiphenanthridinone derivative, synthetic method thereof and electronic device containing thiaphenanthridinone derivative
  • Thiphenanthridinone derivative, synthetic method thereof and electronic device containing thiaphenanthridinone derivative
  • Thiphenanthridinone derivative, synthetic method thereof and electronic device containing thiaphenanthridinone derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] Embodiment 1: the synthesis of compound 71

[0132] (Synthesis of Intermediate 1)

[0133] The synthetic route of intermediate 1 is as follows:

[0134]

[0135] Under nitrogen atmosphere, add 100mL dichloromethane, methylamine (25mmol, 775mg) and triethylamine (21mmol, 2.94mL) successively to a dry and clean 250mL single-necked bottle, and cool the system to 0°C, dropwise Add [1,1'-biphenyl]-2-sulfonyl chloride (20mmol, 5.06g), continue to stir under ice bath for 15min after the dropwise addition, remove the ice bath, and continue to stir overnight at room temperature, to be reacted After completion, a small amount of water was added to quench the reaction, the organic phase was washed three times with water, and the solvent was evaporated to obtain a crude product, which was further purified by column chromatography (350 mesh silica gel, and the eluent was petroleum ether:dichloromethane=2:1 , V / V) to obtain 4.5 g of white crystalline solid with a yiel...

Embodiment 2

[0144] Embodiment 2: the synthesis of compound 72

[0145] (Synthesis of compound 72)

[0146] The synthetic route of compound 72 is as follows:

[0147]

[0148] Under nitrogen, add intermediate 2 (10mmol, 3.24g), anhydrous potassium carbonate (20mmol, 2.76g), 4-(bis(4-tert-butylphenyl)amino) Phenylboronic acid (12mmol, 4.81g), tetrakis(triphenylphosphine palladium) (0.2mmol, 230mg) and 100mL mixed solvent (toluene:water:ethanol=5:1:1, V / V), the system was heated to reflux and React overnight under reflux. After the reaction is completed, stop heating, and the reaction system is cooled to room temperature by itself. Pour the reaction liquid into about 200 mL of water, extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, and concentrate under reduced pressure. , and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether:dichloromethane=3:1, V / V) to obtain 5.1 g of white solid with a yield of 85%. M...

Embodiment 3

[0149] Embodiment 3: the synthesis of compound 172

[0150] (Synthesis of Intermediate 3)

[0151] The synthetic route of intermediate 3 is as follows:

[0152]

[0153] Add intermediate 1 (20mmol, 4.94g), dibromohydantoin (60mmol, 17.2g) and 150mL water successively to a clean 250mL single-necked bottle, and the system is gradually warmed up to 100°C, and reacted overnight at this temperature, and then After the reaction, the heating was stopped, extracted three times with dichloromethane, and the organic phase was dried and concentrated to obtain the corresponding crude product, which was further purified by column chromatography (350 mesh silica gel, eluent was petroleum ether:ethyl acetate=8:1 , V / V) to obtain 6.4 g of white solid, yield 80%. MS(EI): m / z: 403.02[M + ]. Anal.calcd for C 13 h 9 Br 2 NO 2 S (%): C 38.74, H 2.25, N 3.47; found: C 38.70, H 2.28, N 2.43.

[0154] (Synthesis of compound 172)

[0155] The synthetic route of compoun...

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Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a thiaphenanthridinone derivative, a synthetic method thereof and an electronic device containing thethiaphenanthridinone derivative. The thiaphenanthridinone derivative is represented by a general formula (1), wherein L1 and L2 each independently represent a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms. The thiaphenanthridinone derivative is excellent in film forming property and thermal stability by introducing a ring-shaped rigid structure, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells; and in addition, the thiaphenanthridinone 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 anelectron transport layer, and has the advantages of being capable of reducing driving voltage, improving efficiency, brightness, prolonging service life and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to thiaphenanthridone derivatives and their synthesis methods and electronic devices containing thiaphenanthridone 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 laye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/02C07F7/30C07D417/12C07F7/08C07D417/04C07F7/22C07D417/14C07D495/04C07D491/048C07D487/04C07D487/14C07D491/107C07D495/10C07D417/10C07D471/06C07D471/10C07D498/10C07D513/10C09K11/06H01L51/50H01L51/54
CPCC07D279/02C07F7/0812C07F7/30C07D417/12C07F7/0816C07D417/04C07F7/2208C07D417/14C07D495/04C07D491/048C07D487/04C07D487/14C07D491/107C07D495/10C07D417/10C07D471/06C07D471/10C07D498/10C07D513/10C09K11/06C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1096H10K85/624H10K85/622H10K85/615H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K85/40H10K50/11H10K50/18H10K50/16H10K50/15H10K50/17Y02E10/549
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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