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Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof

A triarylamine, electroluminescence technology, used in luminescent materials, chemical instruments and methods, circuits, etc.

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, there are many problems in the matching of quantum efficiency, lifetime, brightness and new materials of this kind of materials, which restricts the development of OLED industrialization and cannot meet the needs of industrialization for materials.
However, the development cost of existing new materials is relatively high, the synthesis process is relatively complicated, and the requirements for synthesis process and purification process are relatively high, which makes the cost of materials high, resulting in high OLED costs. Many technical parameters have not met the development needs of industrialization. How to develop new high-efficiency materials is the task of OLED workers.

Method used

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  • Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof
  • Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof
  • Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of Example 1 Compound M101

[0030] The synthesis of step 1, diarylamine compound:

[0031]

[0032] Under nitrogen protection system, weigh 100mmol (20.9g) of ligand fluorenyl aromatic amine a and 110mmol (17.16g) of aryl halide b into the reaction system, add KOH solid 400mmol (22.4g), add dry dehydrated Toluene 500ml, under nitrogen protection, catalyst CuI 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g), under nitrogen protection, reflux reaction for 5 hours, cooling after reaction, suction filtration, concentration, dichloromethane as solvent, Perform column chromatography on silica gel and concentrate to obtain 26.22 g of an off-white diamine product with a yield of more than 92% and an HPLC purity of more than 98%. It can be used directly for the next reaction.

[0033] Step 2, the synthesis of triarylamine compound (M101):

[0034]

[0035] Weigh 50mmol (14.25g) of diarylamine compound, 55mmol (17.66g) of carbazolyl halide, 75mmol (8.4g) of p...

Embodiment 2

[0037] Synthesis of Example 2 Compound M106

[0038] The synthesis of step 1, diarylamine compound:

[0039]

[0040] Under nitrogen protection system, weigh 100mmol (25.9g) of ligand fluorenyl aromatic amine a and 110mmol (28.60g) of aryl halide b into the reaction system, add KOH solid 400mmol (22.4g), add dry dehydrated Toluene 500ml, under nitrogen protection, catalyst CuI 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g), under nitrogen protection, reflux reaction for 10 hours, cooling after reaction, suction filtration, concentration, dichloromethane as solvent, Perform column chromatography on silica gel and concentrate to obtain 39.51 g of off-white diamine product with a yield of 90% and a purity of more than 98% by HPLC. It can be used directly for the next reaction.

[0041] Step 2, the synthesis of triarylamine compound (M106):

[0042]

[0043] Weigh 50mmol (21.95g) of diarylamine compound, 55mmol (17.66g) of carbazolyl halide, 75mmol (8.4g) of potassium t...

Embodiment 3

[0046] Example 3 Synthesis of compound M109

[0047] The synthesis of step 1, diarylamine compound:

[0048]

[0049] Under nitrogen protection system, weigh 100mmol (28.5g) of ligand fluorenyl aromatic amine a and 110mmol (25.52g) of aryl halide b into the reaction system, add KOH solid 400mmol (22.4g), add dry dehydrated Toluene 500ml, under nitrogen protection, catalyst CuI 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g), under nitrogen protection, reflux reaction for 8 hours, cooling after reaction, suction filtration, concentration, dichloromethane as solvent, Perform column chromatography on silica gel and concentrate to obtain 20.11 g of off-white diamine product with a yield of 92% and an HPLC purity greater than 98%. It can be used directly for the next reaction.

[0050] Step 2, the synthesis of triarylamine compound (M109):

[0051]

[0052] Weigh 50mmol (21.85g) of diarylamine compound, 55mmol (21.84g) of carbazolyl halide, 75mmol (8.4g) of potassium tert...

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Abstract

The invention discloses an organic electroluminescent material containing a tertiary aromatic amine structure. The organic electroluminescent material containing the tertiary aromatic amine structure is characterized in that: the structural formula is shown in the specifications; and in the structural formula, n1, n2 and n3 independently represent that the quantity of benzene ring is 0 or 1 respectively; a radical A represents a substituted carbazole radical; a radical B represents a structural radical containing substituted fluorenyl; and a structure C is a structure radical containing phenyl and substituted phenyl. The organic electroluminescent material is a fluorescent material which has high luminous efficiency; a result of the luminous efficiency in a solution can further indicate that the organic electroluminescent material which has high luminous efficiency and of which the brightness and performance can meet the industrial development can be applied to electroluminescent devices by serving as a luminous material or a luminous main body material or a transmission material. A synthesizing process has the advantages of reaction in two simple steps, easiness and convenience for operating, easiness for purifying, great increase in the industrial synthesizing yield, great reduction in cost, wide application, applicability to a plurality of materials for devices, and wide prospect. Meanwhile, a substituted radical is adjusted, so that the performance of the material further meets requirement of industrialization.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an organic electroluminescent material containing a triarylamine structure. Background technique [0002] 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. Makes the slow progress in the industrialization of OLED. [0003] Organic electroluminescent technology is the latest generation of flat-panel display technology, which can be used for flat-panel displays and lighting sources. At present, commercial flat-panel displays have been put into the market...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88C09K11/06H01L51/54
Inventor 马晓宇王辉赵云霄
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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