Phosphorescent luminescent materials and preparation method and application thereof

A technology for luminescent materials and organic material layers, applied in the directions of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve the effects of improving luminous efficiency, improving experimental conditions, and simplifying synthesis methods

Inactive Publication Date: 2012-10-03
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the relatively high synthesis price of phosphorescent materials, relatively high synthesis process requirements, relatively high purification requirements, very low lifespan, and the efficiency has not reached the expected height, so it has not yet fully met the market demand.

Method used

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  • Phosphorescent luminescent materials and preparation method and application thereof
  • Phosphorescent luminescent materials and preparation method and application thereof
  • Phosphorescent luminescent materials and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Example 1 Compound A101

[0025] Step 1, the synthesis of bridging ligand:

[0026]

[0027] Under the nitrogen protection system, weigh 22mmol (5.13g) of the ligand and put 10mmol (3.52g) of IrCl3 3H2O into the reaction system, add a mixed solution of 300ml ethylene glycol ether and 100ml pure water, and reflux for 24 hours under the protection of nitrogen , and then cooled to room temperature, there is a precipitate, the precipitate is suction filtered, rinsed with water, dried, and dichloromethane is used as a detergent, and silica gel column chromatography is used to concentrate and precipitate a solid to obtain 4.2 g of the bridged ligand. The yield is in 92%.

[0028] Step 2, the synthesis of metal iridium complex (A101):

[0029]

[0030] Weigh 4 mmol (3.67 g) of the bridging ligand, add 4.5 g of anhydrous sodium carbonate, add 200 ml of ethylene glycol ether to the system, add 16 mmol (1.6 g) of acetylacetone, reflux for 10 hours u...

Embodiment 2

[0032] Synthesis of Example 2 Compound A103

[0033] Step 1, the synthesis of bridging ligand:

[0034]

[0035] Under nitrogen protection system, weigh 22mmol (6.49g) of the ligand, put IrCl3 3H2O 10mmol (3.52g) into the reaction system, add 300ml ethylene glycol ether and 100ml pure water mixed solution, and reflux for 24 hours under nitrogen protection , and then cooled to room temperature, a precipitate precipitated, the precipitate was suction filtered, rinsed with water, and dried. Dichloromethane was used as a detergent, and silica gel column chromatography was used to concentrate and precipitate a solid to obtain 4.69 g of a bridged ligand. Yield at 90%.

[0036] Step 2, the synthesis of metal iridium complex (A103):

[0037]

[0038] Weigh 4mmol (4.17g) of the bridging ligand, add 4.5g of anhydrous sodium carbonate, add 200ml of ethylene glycol ether to the system, add 16mmol (1.6g) of acetylacetone, reflux for 15 hours under nitrogen protection, and...

Embodiment 3

[0040] Example 3 Synthesis of Compound A109

[0041] Step 1, the synthesis of bridging ligand:

[0042]

[0043] Under nitrogen protection system, weigh 22mmol (6.62g) of the ligand, put IrCl3 3H2O 10mmol (3.52g) into the reaction system, add 300ml ethylene glycol ether and 100ml pure water mixed solution, and reflux for 24 hours under nitrogen protection , and then cooled to room temperature, a precipitate precipitated, the precipitate was suction filtered, rinsed with water, and dried. Using dichloromethane as a detergent, silica gel column chromatography was used to concentrate and precipitate a solid to obtain 4.91 g of a bridged ligand. Yield at 93%.

[0044] Step 2, the synthesis of metal iridium complex (A109):

[0045]

[0046] Weigh 4 mmol (4.22 g) of the bridging ligand, add 4.5 g of anhydrous sodium carbonate, add 200 ml of ethylene glycol ether to the system, add 16 mmol (1.6 g) of acetylacetone, reflux for 12 hours under nitrogen protection, and...

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Abstract

The invention discloses phosphorescent luminescent materials and a preparation method and application thereof. The invention is characterized in that the phosphorescent luminescent materials are red light materials containing a metal iridium complex; a structural general formula of the phosphorescent luminescent materials is shown in the specification; and in the structural general formula, R1 and R2 are independently one of alkyl, phenyl, halogen-substituted phenyl, alkyl-substituted phenyl, naphthyl, anthryl, a halogen substituent, methoxy, phenoxy, cyano-substituted carbazolyl, substituted N-phenylcarbazolyl, quinolyl, thiazolyl, thienyl, an aromatic amino group, a group with an azole structure, an aromatic heterocyclic radical, a substituted aromatic heterocyclic radical and a silicon alkyl substituent respectively. The phosphorescent materials have high luminous efficiency; and the high luminous efficiency shows that the compounds can be taken as luminescent materials or main luminescent materials and applied to electroluminescent devices. Through data test and comparison, the materials are organic electroluminescent materials which have excellent performance and a good prospect, and particularly are phosphorescent red light materials which have good performance; and moreover, a method for synthesizing the luminescent materials is simple and low in cost.

Description

technical field [0001] The present invention relates to the field of organic photoelectric materials, in particular to phosphorescent organic electroluminescent materials, electroluminescent materials containing novel organometallic iridium complexes, synthesis methods of this series of compounds, light-emitting devices using such derivatives and corresponding electronic equipment. [0002] Background technique [0003] The development of OLED (organic electroluminescent device) has made great progress worldwide, but with the progress of application development, the requirements for materials are getting higher and higher, especially some organic light-emitting materials that can improve performance. Due to the relatively difficult synthesis technology and difficult purification, the synthesis process of some compounds may also involve relatively toxic raw materials or processing processes, which makes the progress in the industrialization of OLEDs slow. [0004] Orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00H01L51/54
Inventor 王辉马晓宇于占双
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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