Compound, application thereof and organic electroluminescent device

Abstract

The invention provides a compound, application thereof and an organic electroluminescent device. The compound has a structure shown as a formula (I). The compound is used as an electron transport material in an organic electroluminescent device; the organic electroluminescent device includes a first electrode, a second electrode, and an organic layer interposed between the first electrode and thesecond electrode, wherein the organic layer containing the compound. The compound provided by the invention has relatively high electron injection capability and electron migration capability, and when the compound is used for an organic electroluminescent device, the device can have relatively high light-emitting efficiency and relatively low working voltage.

Description

technical field

[0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound and its application, and an organic electroluminescence device. Background technique

[0002] At present, with the continuous advancement of organic light-emitting diode (OLED) technology in the two fields of display and lighting, people pay more attention to the research of its core materials. As core materials, common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and luminescent host materials and luminescent objects (dye).

[0003] Various types of electron transport materials with strong transport capacity and high stability have been reported in previous articles and patents. Generally speaking, electron-transporting materials are compounds with electron-deficient nitrogen-containing hete...

Examples

Synthetic example 1

[0126] Synthesis of compound C9:

[0127]

[0128] (1) Preparation of compound 1-1

[0129] At room temperature, under a nitrogen atmosphere, add 2-bromo-1-(3,5 -dichlorophenyl)ethanone (10.77g, 40.49mmol). After the addition, heat to reflux and stir for 5 hours. TLC detected that the reaction was complete, extracted with ethyl acetate, and washed the organic phase with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, spin-dried under reduced pressure, and obtained compound 1-1 (13.44 g, yield 80%) by column chromatography .

[0130] (2) Preparation of compound 1-2

[0131] 1-1 (13.44g, 32.39mmol), 3-cyanophenylboronic acid (4.76g, 32.39mmol), potassium carbonate (13.41g, 97.17mmol), tetrakistriphenylphosphopalladium (0.81g, 0.65 mmol), 150 mL of solvent toluene, 30 mL of ethanol, and 30 mL of water were added, and the reaction was refluxed overnight at 80° C. under nitrogen replacement three times under protection. A solid precipitate...

Synthetic example 2

[0137] Synthesis of compound C28

[0138]

[0139] (1) Preparation of compound 2-1

[0140] Add 2-amino-4-chloro-6-phenyl-1,3,5-triazine (10.0g, 48.54mmol), 9,9-dimethylfluorene-3-boronic acid (11.55g, 48.54 mmol), potassium carbonate (20.09g, 145.63mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.71g, 0.97mmol), add solvent toluene 100mL, ethanol 20ml , 20 mL of water, and reflux at 80° C. overnight under nitrogen replacement three times and protection. A solid precipitated out during the reaction. It was detected by TLC that the reaction of the raw materials was complete, the reaction was stopped and cooled to room temperature, the precipitated solid was filtered, rinsed with water and ethanol respectively, and dried. The target compound 2-1 (10.60 g, yield 60%) was obtained.

[0141] (2) Preparation of compound 2-2

[0142] 2-Bromo-1-(3-bromophenyl)ethanone (8.04g, 29.12mmol) was added to 2-1 (10.60g, 29.12mmol) in DMF solution (20ml) under nitro...

Synthetic example 3

[0148] Synthesis of compound C46:

[0149]

[0150] (1) Preparation of compound 3-1

[0151] At room temperature, add 2-bromo-1-( 3,5-Dichlorophenyl)ethanone (11.13 g, 40.32 mmol). After the addition, heat to reflux and stir for 5 hours. TLC detected that the reaction was complete, extracted with ethyl acetate, and washed the organic phase with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, spin-dried under reduced pressure, and obtained compound 3-1 (13.74 g, yield 80%) by column chromatography .

[0152] (2) Preparation of Compound C46

[0153] Add 3-1 (13.74g, 32.26mmol), 2-(3-boronate phenyl)-4,6-diphenyl-1,3,5-triazine (14.03g, 32.26mmol ), potassium carbonate (13.35g, 96.77mmol), tetrakistriphenylphosphopalladium (0.81g, 0.65mmol), add 150mL of solvent toluene, 30ml of ethanol, 30mL of water, replace with nitrogen three times and react at 80°C under protection and reflux overnight. A solid precipitated out during the reaction. ...

technical field

[0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound and its application, and an organic electroluminescence device. Background technique

[0002] At present, with the continuous advancement of organic light-emitting diode (OLED) technology in the two fields of display and lighting, people pay more attention to the research of its core materials. As core materials, common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and luminescent host materials and luminescent objects (dye).

[0003] Various types of electron transport materials with strong transport capacity and high stability have been reported in previous articles and patents. Generally speaking, electron-transporting materials are compounds with electron-deficient nitrogen-containing hete...

Examples

Synthetic example 1

[0126] Synthesis of compound C9:

[0127]

[0128] (1) Preparation of compound 1-1

[0129] At room temperature, under a nitrogen atmosphere, add 2-bromo-1-(3,5 -dichlorophenyl)ethanone (10.77g, 40.49mmol). After the addition, heat to reflux and stir for 5 hours. TLC detected that the reaction was complete, extracted with ethyl acetate, and washed the organic phase with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, spin-dried under reduced pressure, and obtained compound 1-1 (13.44 g, yield 80%) by column chromatography .

[0130] (2) Preparation of compound 1-2

[0131] 1-1 (13.44g, 32.39mmol), 3-cyanophenylboronic acid (4.76g, 32.39mmol), potassium carbonate (13.41g, 97.17mmol), tetrakistriphenylphosphopalladium (0.81g, 0.65 mmol), 150 mL of solvent toluene, 30 mL of ethanol, and 30 mL of water were added, and the reaction was refluxed overnight at 80° C. under nitrogen replacement three times under protection. A solid precipitate...

Synthetic example 2

[0137] Synthesis of compound C28

[0138]

[0139] (1) Preparation of compound 2-1

[0140] Add 2-amino-4-chloro-6-phenyl-1,3,5-triazine (10.0g, 48.54mmol), 9,9-dimethylfluorene-3-boronic acid (11.55g, 48.54 mmol), potassium carbonate (20.09g, 145.63mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.71g, 0.97mmol), add solvent toluene 100mL, ethanol 20ml , 20 mL of water, and reflux at 80° C. overnight under nitrogen replacement three times and protection. A solid precipitated out during the reaction. It was detected by TLC that the reaction of the raw materials was complete, the reaction was stopped and cooled to room temperature, the precipitated solid was filtered, rinsed with water and ethanol respectively, and dried. The target compound 2-1 (10.60 g, yield 60%) was obtained.

[0141] (2) Preparation of compound 2-2

[0142] 2-Bromo-1-(3-bromophenyl)ethanone (8.04g, 29.12mmol) was added to 2-1 (10.60g, 29.12mmol) in DMF solution (20ml) under nitro...

Synthetic example 3

[0148] Synthesis of compound C46:

[0149]

[0150] (1) Preparation of compound 3-1

[0151] At room temperature, add 2-bromo-1-( 3,5-Dichlorophenyl)ethanone (11.13 g, 40.32 mmol). After the addition, heat to reflux and stir for 5 hours. TLC detected that the reaction was complete, extracted with ethyl acetate, and washed the organic phase with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, spin-dried under reduced pressure, and obtained compound 3-1 (13.74 g, yield 80%) by column chromatography .

[0152] (2) Preparation of Compound C46

[0153] Add 3-1 (13.74g, 32.26mmol), 2-(3-boronate phenyl)-4,6-diphenyl-1,3,5-triazine (14.03g, 32.26mmol ), potassium carbonate (13.35g, 96.77mmol), tetrakistriphenylphosphopalladium (0.81g, 0.65mmol), add 150mL of solvent toluene, 30ml of ethanol, 30mL of water, replace with nitrogen three times and react at 80°C under protection and reflux overnight. A solid precipitated out during the reaction. ...

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