Red light phosphorescent host material, preparation method and organic electroluminescent device thereof

A phosphorescent main body and red light technology, which is applied in the direction of luminescent materials, electric solid devices, semiconductor devices, etc., can solve the problems that are not conducive to carrier injection and transport balance, low glass transition temperature, lack of main materials, etc., and achieve effective Conducive to the balance of carrier transport, good thermal stability, and easy access to raw materials

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, efficient red phosphorescent devices are rare, mainly due to the lack of suitable host materials.
[0003] At present, the host material widely used in red phosphorescent devices is CBP, but it requires high driving voltage and glass transition temperature (T g ) Low (T g =62℃), easy to crystallize
In addition, CBP is a p-type material, and the hole mobility is much higher than the electron mobility, which is not conducive to the balance of carrier injection and transport.

Method used

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  • Red light phosphorescent host material, preparation method and organic electroluminescent device thereof
  • Red light phosphorescent host material, preparation method and organic electroluminescent device thereof
  • Red light phosphorescent host material, preparation method and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The red phosphorescence host material of this example, namely 2',7'-bis(pyridin-3-yl)spiro[benzo[c]fluorene-7,9'-fluorene], the preparation steps are as follows:

[0042]

[0043] Under argon protection, 2',7'-dibromospiro[benzo[c]fluorene-7,9'-fluorene] (105mg, 0.2mmol), pyridine-3-boronic acid (49mg, 0.4mmol) were added to the In the flask with 10ml of toluene solvent, after fully dissolving, potassium carbonate (2mL, 2mol / L) solution is added in the flask, vacuumized to remove oxygen and filled with argon, then add bistriphenylphosphine palladium dichloride (5.6 mg, 0.008mmol); the flask was heated to 100°C for Suzuki coupling reaction for 24h. Stop the reaction and cool to room temperature, extract the reaction solution several times with dichloromethane, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate and then spin dry to obtain the crude product, which is then used with petroleum ether with a volume ratio of 10:1 Using e...

Embodiment 2

[0047] The red phosphorescence host material of this example, namely 2',7'-bis(pyridin-3-yl)spiro[benzo[c]fluorene-7,9'-fluorene], the preparation steps are as follows:

[0048]

[0049]Under the protection of mixed gas of nitrogen and argon, 2',7'-dibromospiro[benzo[c]fluorene-7,9'-fluorene] (157mg, 0.3mmol), pyridine-3-boronic acid (81mg, 0.66 mmol) and 15mL tetrahydrofuran into a 50mL two-neck bottle, fully dissolved, and then a mixed gas of nitrogen and argon was introduced to exhaust the air for about 20 minutes, then tetrakistriphenylphosphine palladium (4mg, 0.003mmol) was added to it, fully dissolved Then add sodium bicarbonate (3mL, 2mol / L) solution. Then, the mixed gas of nitrogen and argon was exhausted for about 10 minutes, and the two-neck flask was added to 70°C for Suzuki coupling reaction for 48 hours. Stop the reaction and cool to room temperature, extract the reaction solution several times with dichloromethane, combine the organic phases, and dry the org...

Embodiment 3

[0051] The red phosphorescence host material of this example, namely 2',7'-bis(pyridin-3-yl)spiro[benzo[c]fluorene-7,9'-fluorene], the preparation steps are as follows:

[0052]

[0053] Under nitrogen protection, 2',7'-dibromospiro[benzo[c]fluorene-7,9'-fluorene] (157mg, 0.3mmol), pyridine-3-boronic acid (89mg, 0.72mmol), palladium acetate (3.5mg, 0.015mmol) and tri(o-methoxyphenyl)phosphine (21mg, 0.06mmol) were added into a flask filled with 12mL of N,N-dimethylformamide, and potassium carbonate ( 3mL, 2mol / L) solution, and then blow nitrogen into the flask to exhaust the air for about 30min; heat the flask to 130°C for Suzuki coupling reaction for 12h. Stop the reaction and cool to room temperature, extract the reaction solution several times with dichloromethane, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate and then spin dry to obtain the crude product, which is then used with petroleum ether with a volume ratio of 10:1 Using...

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Abstract

Belonging to the field of organic semiconductor materials, the invention discloses a red light phosphorescent host material, a preparation method and an organic electroluminescent device thereof. The host material has a structural formula shown as the specification. The red light phosphorescent host material provided by the invention has electron transport performance, strengthened electron transport capacity, is conducive to carrier transport balance, has a high triplet state energy level, and can effectively prevent back transmission of energy to the host material in a luminescence process, thus greatly improving the luminescence efficiency.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a red phosphorescence host material and a preparation method thereof. The invention also relates to an organic electroluminescent device, the material of the light-emitting layer contains a red phosphorescence host material. Background technique [0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, rich colors through fine-tuning of chemical structure, easy realization of high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Future efficient commercial OLEDs will likely contain organometallic phosphors because they can trap both singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. However, due to the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/06C07D213/127H01L51/54
CPCC09K11/06C07D213/06C07D213/127C09K2211/1029C09K2211/1018H10K85/654
Inventor 周明杰张振华王平张娟娟
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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