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Preparation method and application of derivative by taking dibenzofuran as skeleton core

A derivative and diphenyl technology, applied in the field of derivative compounds, can solve problems such as the inability to produce high-performance light-emitting devices, and achieve the effects of increasing driving life, improving efficiency and life, and high luminous efficiency

Active Publication Date: 2015-05-27
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For OLED devices, although breakthroughs have been made in the individual indicators of individual colors (pure efficiency, or lifespan), it is impossible to produce high-performance light-emitting devices with excellent overall performance.

Method used

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  • Preparation method and application of derivative by taking dibenzofuran as skeleton core
  • Preparation method and application of derivative by taking dibenzofuran as skeleton core
  • Preparation method and application of derivative by taking dibenzofuran as skeleton core

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the synthesis of compound 001

[0032] Concrete synthetic route is as follows:

[0033]

[0034] Weigh 36.00g of 1,6-dibromopyrene, 104.21g of 14H-dibenzofurocarbazole, 13.46g of potassium tert-butoxide, 0.41g of palladium(II) acetate, 0.45g of tri-tert-butylphosphine, and use 250ml of toluene Dissolve and react at 80°C for 10 hours under nitrogen protection. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, and the obtained solid was recrystallized from toluene and dried to obtain 74.11 g of light gray solid compound 1,6-bis(14H-dibenzofurocarbazole)pyrene , the yield is more than 83%, and the HPLC purity is greater than 98%. Mass spectrum: calculated value 892.95; found value 892.93. Elemental analysis: calculated value C: 86.08%; H: 3.61%; N: 3.14%; O: 7.17%; tested value C: 86.10%; H: 3.60%; N: 3.13%; O: 7.17%.

[0035]

Embodiment 2

[0036] Embodiment 2: the synthesis of compound 002

[0037] Concrete synthetic route is as follows:

[0038]

[0039] Weigh 35.20g of 2,7-dibromo-9,9-dimethylfluorene, 107.68g of 14H-dibenzofurocarbazole, 14.36g of potassium tert-butoxide, 0.48g of palladium(II) acetate, tri-tert-butyl 0.54 g of base phosphorus was dissolved in 250 ml of toluene, and reacted at 82° C. for 11 hours. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, the obtained solid was recrystallized from toluene, and dried to obtain 75.22 g of light gray solid compound 14,14'-(9,9-dimethylfluorenediyl)bis (14H-dibenzofurocarbazolyl), the yield is over 85%, and the HPLC purity is over 98%. Mass Spectrum: Calculated 884.97; Found 884.95. Elemental analysis: calculated value C: 85.50%; H: 4.10%; N: 3.17%; O: 7.23%; tested value C: 85.52%; H: 4.11%; N: 3.16%; O: 7.21%.

Embodiment 3

[0040] Embodiment 3: the synthesis of compound 003

[0041] Concrete synthetic route is as follows:

[0042]

[0043]Weigh 33.60g of 9,10-dibromoanthracene, 111.15g of 14H-dibenzofurocarbazole, 15.26g of potassium tert-butoxide, 0.56g of palladium (II) acetate, 0.63g of tri-tert-butylphosphine, and use 250ml of toluene Dissolve and react at 84°C for 12 hours. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, the obtained solid was recrystallized from toluene, and dried to obtain 72.99 g of light gray solid compound 9,10-bis(14H-dibenzofurocarbazolyl)anthracene , the yield is more than 84%, and the HPLC purity is greater than 98%. Mass Spectrum: Calculated 868.93; Found 868.92. Elemental analysis: calculated value C: 85.70%; H: 3.71%; N: 3.22%; O: 7.37%; tested value C: 85.72%; H: 3.72%; N: 3.21%; O: 7.35%.

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Abstract

The invention discloses a derivative compound by taking the dibenzofuran as a skeleton core and an application of the derivative compound in OLED. The derivative is a derivative compound by taking the dibenzofuran carbazole as a skeleton core; the outside of the dibenzofuran carbazole is connected with a functional group through a C-C bond or C-N bond. After the derivative compound taking the dibenzofuran carbazole as a skeleton core is used on OLED, the efficiency and the service life can be increased and the driving life can be greatly improved.

Description

technical field [0001] The invention discloses a derivative compound with dibenzofurocarbazole as the core skeleton, and the application of the derivative compound with dibenzofurocarbazole as the core skeleton in OLEDs. Background technique [0002] As a self-illuminating electronic component, organic electroluminescent OLEDs (Organic Light Emission Diodes) show that the light-emitting principle of lighting components is a new type of photoelectric information that converts electrical energy directly into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. A type of technology. Its luminous color can be red, green, blue alone or combined into white. The biggest feature of OLED light-emitting display technology is that it is ultra-thin, light-weight, and surface-emitting. It can be used to manufacture monochrome or full-color displays. As a new light source technology, it can also be used to manufacture lighting ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D491/153C09K11/06H01L51/54
Inventor 马晓宇王辉李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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