Green phosphorescent host material with excellent performance and organic electroluminescent device

Abstract

The invention discloses a green phosphorescent host material with excellent performance and an organic electroluminescent device. The structural formula of the material is shown in the specification.Compared with a contrast example, the organic electroluminescent device prepared from the green phosphorescent host material with excellent performance has the advantages that: the voltage is greatlyreduced, and the luminous efficiency is remarkably improved. Therefore, the compound provided by the invention can greatly reduce the driving voltage of the device, greatly reduces the consumption ofelectric energy, and remarkably improves the luminous efficiency. In addition, by reducing the driving voltage, the service life of the organic electroluminescent device is remarkably prolonged.

Description

technical field

[0001] The invention relates to the field of organic electroluminescence materials, and specifically relates to a green phosphorescence host material with excellent performance and an organic electroluminescence device. Background technique

[0002] Organic electroluminescence is a phenomenon that electric energy excites organic materials to emit light. The light-emitting layer composed of light-emitting materials is the most critical part of light-emitting devices, so light-emitting materials are crucial to organic electroluminescence. Usually, the luminescent material needs to meet the following requirements: good semiconductor characteristics, capable of conducting electrons or holes; the fluorescence spectrum is in the visible region of 280-780nm, and the fluorescence quantum yield is high; the chemical properties are stable, and it is difficult to have side reactions with other materials; film-forming properties Good, easy to form dense amorphous film an...

Examples

Embodiment 1

[0047]

[0048] The preparation method of the green phosphorescent host material (1) with excellent performance is as follows:

[0049] (1)

[0050]

[0051] Compound 1-a (2-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523g / mol, 9.56mmol), compound 1-b ((4,6-diphenyl-1,3,5-triazin-2-yl) boronic acid) (1eq, 2.65g, 277g / mol, 9.56mmol) and sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) was added in ethylene glycol diamine ether (100g, 20 times the quality of compound 1-a) and water (100g, 20 times the quality of compound 1-a), After stirring and mixing, tri(o-tolyl)phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium(II) acetate (0.5%eq, 0.011g, 224.51g / mol, 0.048 mmol), after heating up to reflux for 15 hours, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 1-c (2-(4,6-diphenyl-1,3,5-triazin -2-yl)-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazo...

Embodiment 2

[0056]

[0057] The preparation method of the green phosphorescent host material (2) with excellent performance is as follows:

[0058] (1)

[0059]

[0060] Compound 2-a (2-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523.06 g / mol, 9.56mmol), compound 2-b ((4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)boronic acid) (1eq, 3.38g, 353.13g / mol, 9.56mmol) and sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) were added to ethylene glycol diamine ether (100g, 20 times the mass of compound 2-a ) and water (100g, 20 times the mass of compound 2-a), stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium acetate (II) (0.5%eq, 0.011g, 224.51g / mol, 0.048mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 2-c after column chromatography (2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triaz...

Embodiment 3

[0065]

[0066] The preparation method of the green phosphorescent host material (11) with excellent performance is as follows:

[0067] (1)

[0068]

[0069] Compound 3-a (3-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523.06 g / mol, 9.56mmol), compound 3-b ((4,6-diphenyl-1,3,5-triazin-2-yl)boronic acid) (1eq, 2.65g, 277.10g / mol, 9.56mmol) and Sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) was added to ethylene glycol diamine ether (100g, 20 times the mass of compound 3-a) and water (100g, 20 times the mass of compound 3-a) , stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium (II) acetate (0.5%eq, 0.011g, 224.51g / mol , 0.048mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 3-c (3-(4,6-diphenyl-1,3,5 -triazin-2-yl)-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazo...

technical field

[0001] The invention relates to the field of organic electroluminescence materials, and specifically relates to a green phosphorescence host material with excellent performance and an organic electroluminescence device. Background technique

[0002] Organic electroluminescence is a phenomenon that electric energy excites organic materials to emit light. The light-emitting layer composed of light-emitting materials is the most critical part of light-emitting devices, so light-emitting materials are crucial to organic electroluminescence. Usually, the luminescent material needs to meet the following requirements: good semiconductor characteristics, capable of conducting electrons or holes; the fluorescence spectrum is in the visible region of 280-780nm, and the fluorescence quantum yield is high; the chemical properties are stable, and it is difficult to have side reactions with other materials; film-forming properties Good, easy to form dense amorphous film an...

Examples

Embodiment 1

[0047]

[0048] The preparation method of the green phosphorescent host material (1) with excellent performance is as follows:

[0049] (1)

[0050]

[0051] Compound 1-a (2-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523g / mol, 9.56mmol), compound 1-b ((4,6-diphenyl-1,3,5-triazin-2-yl) boronic acid) (1eq, 2.65g, 277g / mol, 9.56mmol) and sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) was added in ethylene glycol diamine ether (100g, 20 times the quality of compound 1-a) and water (100g, 20 times the quality of compound 1-a), After stirring and mixing, tri(o-tolyl)phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium(II) acetate (0.5%eq, 0.011g, 224.51g / mol, 0.048 mmol), after heating up to reflux for 15 hours, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 1-c (2-(4,6-diphenyl-1,3,5-triazin -2-yl)-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazo...

Embodiment 2

[0056]

[0057] The preparation method of the green phosphorescent host material (2) with excellent performance is as follows:

[0058] (1)

[0059]

[0060] Compound 2-a (2-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523.06 g / mol, 9.56mmol), compound 2-b ((4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)boronic acid) (1eq, 3.38g, 353.13g / mol, 9.56mmol) and sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) were added to ethylene glycol diamine ether (100g, 20 times the mass of compound 2-a ) and water (100g, 20 times the mass of compound 2-a), stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium acetate (II) (0.5%eq, 0.011g, 224.51g / mol, 0.048mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 2-c after column chromatography (2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triaz...

Embodiment 3

[0065]

[0066] The preparation method of the green phosphorescent host material (11) with excellent performance is as follows:

[0067] (1)

[0068]

[0069] Compound 3-a (3-bromo-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazole]) (5g, 523.06 g / mol, 9.56mmol), compound 3-b ((4,6-diphenyl-1,3,5-triazin-2-yl)boronic acid) (1eq, 2.65g, 277.10g / mol, 9.56mmol) and Sodium carbonate (2eq, 2.03g, 105.99g / mol, 19.12mmol) was added to ethylene glycol diamine ether (100g, 20 times the mass of compound 3-a) and water (100g, 20 times the mass of compound 3-a) , stir and mix and then add three (o-tolyl) phosphine (3%eq, 0.087g, 304.37g / mol, 0.29mmol) and palladium (II) acetate (0.5%eq, 0.011g, 224.51g / mol , 0.048mmol), after heating up to reflux for 15h, the organic phase was separated, washed with water, concentrated under reduced pressure, and then obtained compound 3-c (3-(4,6-diphenyl-1,3,5 -triazin-2-yl)-5'H-spiro[fluorene-9,9'-indeno[1',2':4,5]furo[2,3-c]carbazo...

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