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Phenanthroimidazole derivative and its application as electroluminescent material

A technology of phenanthroimidazole and electroluminescent devices, which is applied in the direction of luminescent materials, circuits, electrical components, etc., can solve the problems of low efficiency, unsatisfactory molecular efficiency, light color, poor material stability, etc., and achieve high glass transition temperature and good electronic properties. Good transmission ability and thermal stability

Active Publication Date: 2012-08-01
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008]A Chinese patent application with application publication number CN 101870681A published on April 1, 2010 discloses a bis-phenanthroimidazole-based compound and its electroluminescent device. The phenanthrene imidazole unit is used as an OLED material, but the stability of the material is poor. It can be seen from the electroluminescent efficiency diagram that although a high current efficiency can be obtained at a low current density, the device efficiency rolls off with the current The density increase is very serious
In addition, the Chinese patent application published on September 21, 2011 with the application publication number CN102190627A publicly tested fluorescent materials composed of various phenanthroimidazole units, but the light color of the molecular efficiency involved was not satisfactory, and the color coordinates were in the sky blue light. areas, there is still a long way to go to achieve efficient full-color display and lighting, and the efficiency is low

Method used

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  • Phenanthroimidazole derivative and its application as electroluminescent material
  • Phenanthroimidazole derivative and its application as electroluminescent material
  • Phenanthroimidazole derivative and its application as electroluminescent material

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: the preparation method of ACPI of the present invention, this method comprises following three steps:

[0033] (1) Add 208 mg of dry phenanthrenequinone, 93.1 mg of aniline, 185 mg of p-bromobenzaldehyde, and acetic acid as a solvent in the reaction flask, react at 130°C for 12 hours, add 50 mL of water after cooling, filter the precipitate, wash with water, and dry to obtain the product 2- (4-Bromophenyl)-1-phenylphenanthroimidazole 360 ​​mg, yield 80%.

[0034]Dissolve 360 ​​mg of 2-(4-bromophenyl)-1-phenylphenanthroimidazole in 50 mL of anhydrous THF, inject 1.1 molar ratio of n-butyllithium at -78 ° C, and inject 1.5 molar ratio of n-butyl lithium after reacting for 1 hour. Anhydrous trimethyl borate, reacted for 12 hours, added water to quench the reaction, extracted with dichloromethane, dried, and recrystallized from n-hexane to obtain 242mg of 4-(1-phenyl-2-p-phenylphenanthroimidazolyl)phenylboronic acid , yield 73%.

[0035] 4-(1-phenyl-2-p-phen...

Embodiment 2

[0037] Example 2: 1-NaCPI described in the present invention can be synthesized by the following method.

[0038] (1) Add 208 mg of dry phenanthrenequinone, 93.1 mg of aniline, 185 mg of p-bromobenzaldehyde, and acetic acid as a solvent in the reaction flask, react at 130°C for 12 hours, add 50 mL of water after cooling, filter the precipitate, wash with water, and dry to obtain the product 2- (4-Bromophenyl)-1-phenylphenanthroimidazole 360 ​​mg, yield 80%.

[0039] Dissolve 360 ​​mg of 2-(4-bromophenyl)-1-phenylphenanthroimidazole in 50 mL of anhydrous THF, inject 1.1 molar ratio of n-butyllithium at -78 ° C, and inject 1.5 molar ratio of n-butyl lithium after reacting for 1 hour. Anhydrous trimethyl borate, reacted for 12 hours, added water to quench the reaction, extracted with dichloromethane, dried, and recrystallized from n-hexane to obtain 242mg of 4-(1-phenyl-2-p-phenylphenanthroimidazolyl)phenylboronic acid , yield 73%.

[0040] 4-(1-phenyl-2-p-phenylphenanthroimida...

Embodiment 3

[0041] Example 3: 2-NaCPI described in the present invention can be synthesized by the following method.

[0042] (1) Add 208 mg of dry phenanthrenequinone, 93.1 mg of aniline, 185 mg of p-bromobenzaldehyde, and acetic acid as a solvent in the reaction flask, react at 130°C for 12 hours, add 50 mL of water after cooling, filter the precipitate, wash with water, and dry to obtain the product 2- (4-Bromophenyl)-1-phenylphenanthroimidazole 360 ​​mg, yield 80%.

[0043] Dissolve 360 ​​mg of 2-(4-bromophenyl)-1-phenylphenanthroimidazole in 50 mL of anhydrous THF, inject 1.1 molar ratio of n-butyllithium at -78 ° C, and inject 1.5 molar ratio of n-butyl lithium after reacting for 1 hour. Anhydrous trimethyl borate, reacted for 12 hours, added water to quench the reaction, extracted with dichloromethane, dried, and recrystallized from n-hexane to obtain 242mg of 4-(1-phenyl-2-p-phenylphenanthroimidazolyl)phenylboronic acid , yield 73%.

[0044] 4-(1-phenyl-2-p-phenylphenanthroimida...

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Abstract

The invention relates to design and synthesis of an organic electroluminescent blue-light material with phenanthroimidazole and anthracene as the central unit structure and application of the material in a blue organic light-emitting diode (OLED). The material takes phenanthroimidazole as the core. Groups with different electronic properties are bonded at positions C1 and N2, and the glass transition temperature is raised so as to effectively solve carrier injection and realize high efficiency exciton recombination radically, thus further realizing combination of high efficiency light-emitting and energy level adjustment of the material. In addition, polarity of the compound can be adjusted through pushing / pulling an electron group. Compared with the blue fluorescence of common blue fluorescent main material 2-methyl-9, 10-di(naphth-2-yl)anthracene (M-ADN), the OLED has substantial effects in reduction of operating voltage and efficiency enhancement, so that the material provided in the invention can be widely applied in the field of organic electroluminescence.

Description

Technical field [0001] The present invention is the field of organic optoelectronic materials, which specializes in the application of Philippines and the application of imidazole derivatives and its application as an electro -luminous material. Background technique [0002] Electroluminescence (EL) refers to the phenomenon of compounding and lighting of electron and cavities under the action of electrical fields. It is a luminous process that directly converts electrical energy into optical energy.The device made according to this principle is called the mechanical electrical light emitting device.Compared with tablet launch display (FED), LCD display (LCD), plasma display (PDP) and other tablet display technologies, organic electrical light emitting devices have the following characteristics: the material uses organic matter / polymer, so the selection range is wide, Achieve any color from red light to blue light; the driving voltage is low, the lighting brightness and luminous e...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06H01L51/54
Inventor 王磊庄少卿上官荣刚黄宏穆广园
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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