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A kind of fluorine-containing phenanthroimidazole derivative and its synthesis method and application

A carbazole and compound technology, which is applied in the field of organic electroluminescent materials and light-emitting devices, can solve the problems such as the inability to meet the requirements of blue-light electrophosphorescent devices

Active Publication Date: 2017-05-10
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the high triplet energy level of blue light guests such as FIrPic, the above host materials cannot meet the needs of blue light-induced phosphorescent devices.
[0006] In summary, there is still a lack of a method with good charge transport performance and high triplet energy level (E T ), suitable for the preparation of various color devices, especially the host material of blue light-emitting devices

Method used

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  • A kind of fluorine-containing phenanthroimidazole derivative and its synthesis method and application
  • A kind of fluorine-containing phenanthroimidazole derivative and its synthesis method and application
  • A kind of fluorine-containing phenanthroimidazole derivative and its synthesis method and application

Examples

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Embodiment 1

[0182] Example 1: 2-(4,4"-bis(azolyl)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthrene Synthesis of Imidazole (DCzBPI)

[0183] In this example, 2-(4,4"-bis(azolyl)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthrene The structural formula of imidazole is:

[0184]

[0185] Preparation of the above-mentioned 2-(4,4"-bis(azolyl)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthroimidazole The method includes the following steps:

[0186] Step 1: Synthesis of intermediate 1: 2-(3,5-dibromophenyl)-1-(4-(trifluoromethylphenyl)phenanthroimidazole (Br 2 BPI):

[0187] In a 500mL three-necked flask equipped with a stirring, thermometer, and gas-introducing device, argon gas was introduced for 10 minutes, and 100 parts of p-trifluoromethylaniline, 20 parts of phenanthrenequinone, and 20 parts of 3,5-dibromobenzaldehyde were sequentially added Dissolve 85 parts of ammonium acetate in 200 parts of acetic acid, raise the temperature to 125 ° C...

Embodiment 2

[0194] Example 2: 2-(4,4"-bis(diphenylamine)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthrene Preparation of imidazole (DTPABPI)

[0195] In this example, 2-(4,4"-bis(diphenylamine)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthrene The structural formula of imidazole is:

[0196]

[0197] Preparation of the above-mentioned 2-(4,4"-bis(diphenylamine)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthroimidazole The method includes the following steps:

[0198] Step 1: The target compound 2-(4,4"-bis(diphenylamine)-(1,1':3',1"-terphenyl)-1-(4-(trifluoromethylphenyl)phenanthrene Preparation of imidazole (DTPABPI)

[0199] In a three-necked flask equipped with a magnetic stirrer, 1 part of intermediate 1 synthesized in step 1 in Example 1: 2-(3,5-dibromophenyl)-1-(4-(trifluoromethylbenzene Base) phenanthroimidazole, 2.5 parts of 4-triphenylamine borate, 4 parts of 20% tetraethylammonium hydroxide and 0.1 part of tetraphenylphosphopalla...

Embodiment 3

[0202] Example 3: Preparation of DCzBPI organic phosphorescent doped electroluminescent device

[0203] The above-mentioned phenanthroimidazole derivative bipolar host material DCzBPI can be applied to organic phosphorescent doped electroluminescent devices. The electroluminescent device is a layered doped structure, such as figure 1 As shown, the sequence from substrate to cathode is substrate 1, transparent conductive film 2, hole injection layer 3, hole transport layer 4, light emitting layer 5, electron transport layer 6, electron injection layer 7 and cathode 8. Among them, the substrate 1 is made of glass or transparent plastic; the transparent conductive film 2 is made of indium tin oxide (ITO) with an area resistance of 20Ω / sq as the anode; after the substrate is cleaned, it is glow-discharged (plasma) in a high-purity oxygen atmosphere Treat for 10min, under high vacuum (3~2×10 -4 Pa), on the transparent conductive film 2, vapor-deposit a layer of 20nm thick 4,4',4'...

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Abstract

The present invention provides a fluorine-containing phenanthroimidazole derivative, its preparation method and application, specifically, the present invention provides a compound with the structure of formula I: wherein, the definition of R is as described in the description. The compound of the present invention can be used to prepare light-emitting materials, or to prepare electroluminescent devices. It has the characteristics of good stability, high performance and high efficiency, and is especially suitable for preparing electroluminescent devices with four colors of red, green, blue and yellow. Luminescent devices.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials and light-emitting devices, and specifically relates to phenanthroimidazole derivatives and preparation methods thereof, and organic electroluminescent devices of the series of materials. Background technique [0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, and high resolution, and have become a research hotspot in the fields of materials, information, and physics. According to different luminescent principles, organic electroluminescent materials are divided into two categories: fluorescent materials and phosphorescent materials. Compared with fluorescent materials, phosphorescent materials can utilize triplet and singlet excitons, and the internal quantum efficiency can theoretically reach 100%. Therefore, the use of phosphorescent materials is an important means to obtain high-efficiency or...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D235/02C09K11/06H01L51/54
CPCC09K11/06C07D235/02C07D403/14C09K2211/1007C09K2211/1044H10K85/6572H10K50/11
Inventor 葛子义张兴业欧阳新华
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI