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Organic electroluminescent material of large-pi conjugated system and preparation method and application thereof

A technology of electroluminescent materials and conjugated systems, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve the effects of improved efficiency, simple synthesis, and good film-forming performance

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, existing materials still have application problems, such as lifespan, brightness, and efficiency. How to develop materials with excellent performance is the top priority.

Method used

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  • Organic electroluminescent material of large-pi conjugated system and preparation method and application thereof
  • Organic electroluminescent material of large-pi conjugated system and preparation method and application thereof
  • Organic electroluminescent material of large-pi conjugated system and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Synthesis of Type A Compound

[0020] Synthesis of compound A101

[0021]

[0022] Under a nitrogen protection system, weigh 100mmol (15.6g) of aryl halide bromobenzene and 110mmol (50g) of arylboronic acid into the reaction system, add 440mmol (46.64g) of anhydrous Na2CO3 solid, and add 220ml of water to the system. Added 440ml of toluene, under the protection of nitrogen, the catalyst Pd(PPh3) 4 5mmol (5.77g), react at a constant temperature of 90℃ under the protection of nitrogen for 8-12 hours, after the reaction is cooled, filtered with suction, washed, extracted, concentrated, dichloromethane As a solvent, silica gel was used for column chromatography and concentrated to obtain 43.85 g of an off-white final product with a yield of over 85% and an HPLC purity of over 98%.

[0023] Mass spectrum: calculated value is 487.17; tested value is 487.15. Elemental analysis: calculated value C: 88.68%; H: 4.55%; F: 3.70%; N: 2.87%; test value: C: 88.66%; H: 4.52%; F: 3...

Embodiment 2

[0040] Example 2 Synthesis of Type B Compound

[0041] Synthesis of B101

[0042]

[0043] Under a nitrogen protection system, weigh 100mmol (15.6g) of aryl halide bromobenzene and 110mmol (52g) of arylboronic acid into the reaction system, add 440mmol (46.64g) of anhydrous Na2CO3 solid, and add 220ml of water to the system. Added 440ml of toluene, under the protection of nitrogen, the catalyst Pd(PPh3) 4 5mmol (5.77g), react at a constant temperature of 90℃ under the protection of nitrogen for 8-12 hours, after the reaction is cooled, filtered with suction, washed, extracted, concentrated, dichloromethane As a solvent, silica gel was used for column chromatography and concentrated to obtain 43.69 g of an off-white final product with a yield of over 85% and an HPLC purity of over 98%.

[0044] Mass spectrum: calculated value is 505.16; tested value is 505.15. Elemental analysis: calculated value C: 85.53%; H: 4.19%; F: 7.52%; N: 2.77%; test value: C: 85.50%; H: 4.17%; F: 7.50%; N: ...

Embodiment 3

[0061] Example 3 Synthesis of Type C Compound

[0062] Synthesis of compound C101

[0063]

[0064] Under a nitrogen protection system, weigh 100mmol (15.6g) of aryl halide bromobenzene and 110mmol (50g) of arylboronic acid into the reaction system, add 440mmol (46.64g) of anhydrous Na2CO3 solid, and add 220ml of water to the system. Added 440ml of toluene, under the protection of nitrogen, the catalyst Pd(PPh3) 4 5mmol (5.77g), react at a constant temperature of 90℃ under the protection of nitrogen for 8-12 hours, after the reaction is cooled, filtered with suction, washed, extracted, concentrated, dichloromethane As a solvent, silica gel was used for column chromatography and concentrated to obtain 42.86 g of the off-white final product, the yield was over 85%, and the HPLC purity was over 98%.

[0065] Mass spectrum: calculated value is 487.17; tested value is 487.15. Elemental analysis: calculated value C: 88.68%; H: 4.55%; F: 3.90%; N: 2.87%; test value: C: 88.66%; H: 4.52%; F...

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Abstract

The invention relates to an organic electroluminescent material of a large-pi conjugated system. A structural general formula is shown in the specification, wherein A represents aromatic groups. By the organic electroluminescent material, phenanthro-carbazole series derivatives are synthesized; the series derivatives are large in conjugated system and high in film-forming performance, can form a large large-pi conjugated system, and can be used as organic electroluminescent devices (OLED) easily; and particularly, by substituting the introduction of an F atom, electron transition can be regulated, the emission range of different materials emitting blue light from light blue to dark blue can be formed, the demand on light-emitting materials and particularly the required light blue light emitting materials is met. Simultaneously, the organic electroluminescent material is easy to synthesize and purify and low in cost, and can meet the demand of industrial development. The efficiency of the material can be regulated, the efficiency can be improved obviously, the film-forming performance is improved obviously, and the service life of the material is prolonged obviously; and the material is easy and convenient to synthesize and wide in application range, can be used in multiple materials of the devices, and has a bright prospect.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and relates to an organic electroluminescent material containing a large π-conjugated system of carbazole derivatives. 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 processes, which makes the progress in the industrialization of OLEDs slow. [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 fla...

Claims

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Application Information

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IPC IPC(8): C07D209/80C09K11/06H01L51/30H01L51/46H01L51/54
CPCY02E10/549
Inventor 马晓宇王辉崔超
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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