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A fluorene-based phosphorescent host compound and its organic electroluminescent device

A phosphorescent host and compound technology, used in the manufacture of electrical solid devices, semiconductor devices, semiconductor/solid-state devices, etc., can solve the problems of charge imbalance in the light-emitting layer, reduce device efficiency, and difficulty in electron flow, and achieve high luminous purity and good quality. The effect of thermal stability and high luminous efficiency

Active Publication Date: 2018-04-24
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the characteristics of CBP that holes are easy to transport and electrons are difficult to flow, the charge in the light-emitting layer is unbalanced, which reduces the efficiency of the device.

Method used

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  • A fluorene-based phosphorescent host compound and its organic electroluminescent device
  • A fluorene-based phosphorescent host compound and its organic electroluminescent device
  • A fluorene-based phosphorescent host compound and its organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of compound 1

[0048]

[0049] Synthesis of Intermediate 1-1

[0050] In a 250mL three-necked flask, add 9-phenyl-9-(4-bromophenyl)-fluorene (15g, 38mmol), biboronic acid pinacol ester (11.6g, 45mmol), potassium acetate (6g, 76mmol) ), dichlorobistriphenylphosphine palladium (200mg), dioxane (150mL), reflux for 6h under nitrogen protection, remove the solvent after cooling, add water, extract with dichloromethane, dry, filter, concentrate, and use Recrystallization from ethanol and dichloromethane gave 13 g of the product with a yield of 78%.

[0051] Synthesis of compound 1

[0052] Add intermediate 1-1 (2.0g, 4.5mmol), p-bromoiodobenzene (0.56g, 2mmol), tetrakistriphenylphosphine palladium (50mg), potassium carbonate (1.2g, 9mmol), tetrahydrofuran ( 20ml), water (10ml), under the protection of nitrogen, heated to reflux for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatograph...

Embodiment 2

[0054] Synthesis of compound 6

[0055]

[0056] The synthesis method is the same as that of compound 1, except that m-bromoiodobenzene is used instead of p-bromoiodobenzene, and the yield is 82%.

Embodiment 3

[0058] Synthesis of compound 7

[0059]

[0060] Synthesis of Intermediate 7-1

[0061] Add intermediate 1-1 (10.0g, 22.5mmol), p-bromoiodobenzene (6.3g, 22.5mmol), tetrakistriphenylphosphine palladium (150mg), potassium carbonate (6.2g, 45mmol), tetrahydrofuran in a three-necked flask (200ml), water (100ml), under nitrogen protection, heated to reflux for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, the crude product was purified by column chromatography to obtain 7.86g, yield 75%.

[0062] Synthesis of Intermediate 7-2

[0063] The synthesis method was the same as that of intermediate 1-1, except that intermediate 7-1 was used instead of compound 9-phenyl-9-(4-bromophenyl)-fluorene, and the yield was 85%.

[0064] Synthesis of compound 7

[0065] Add intermediate 7-2 (1.0g, 1.9mmol), 2-bromo-9,9-diphenylfluorene (0.8g, 2mmol), tetrakistriphenylphosphine palladium (50mg), potassium carbonate ( 0.56g, 4mmol), tetrahydrofuran (20ml), water (10ml...

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Abstract

The invention provides a compound based on fluorene, which has better thermal stability, high luminous efficiency, and high luminous purity, and can be used to make organic electroluminescent devices, applied to organic solar cells, organic thin film transistors or organic light sensory field. The present invention also provides an organic electroluminescence device, which comprises an anode, a cathode and an organic layer, the organic layer comprising a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer At least one layer of the organic layer contains a compound of formula I.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a fluorene-based phosphorescent host compound and an organic electroluminescent device, belonging to the technical field of display of organic electroluminescent devices. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/52H01L51/54C09K11/06
CPCC09K11/06H10K85/649H10K50/80Y02E10/549Y02P70/50
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD