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Aromatic amine derivatives containing benzophenone group and its preparation method and application

An aromatic amine and benzophenone technology, which is applied in the field of aromatic amine derivatives and their preparation, can solve the problems of low external quantum efficiency of devices, low luminous intensity of phosphorescent OLEDs, and efficiency roll-off, etc., and achieves good hole efficiency. The effect of transmission capability, improving the external quantum efficiency of the device, and low cost

Active Publication Date: 2022-04-19
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the disadvantages of low luminous intensity of existing phosphorescent OLEDs, low external quantum efficiency (EQE) and serious efficiency roll-off, and provide an aromatic amine containing benzophenone group Derivatives, with a unique triphenylamine group, can be used as an organic light-emitting material with good hole transport ability. Triphenylamine has a large steric hindrance effect in the molecule, which makes the whole molecule in a distorted state and reduces the π-π stacking band. Fluorescence quenching, with unique twisted intermolecular charge transfer (TICT) and aggregation-induced emission (AIE) effects, high luminous intensity, good ability to transport holes, when used as OLED, it is used as the host material, and then doped As the guest material, the heterophosphorescent material can reduce the concentration quenching of the phosphorescent material, improve the external quantum efficiency of the device, and reduce the efficiency roll-off

Method used

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  • Aromatic amine derivatives containing benzophenone group and its preparation method and application
  • Aromatic amine derivatives containing benzophenone group and its preparation method and application
  • Aromatic amine derivatives containing benzophenone group and its preparation method and application

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Embodiment 1

[0058] An aromatic amine derivative containing a benzophenone group has a molecular structure as shown in formula (I), named pBZ-DPA:

[0059]

[0060] The preparation method of the above-mentioned aromatic amine derivatives containing benzophenone group comprises the following steps:

[0061] S1. Preparation of (4-bromophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone:

[0062] Weigh (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one 2.87g, 2-aminopyridine 0.94g, iodine 2.53g, 0.154g and 20mL chloroform in In a two-necked flask, a Michael ring closure reaction was carried out at a temperature of 75°C to obtain (4-bromophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone after treatment;

[0063] Its reaction equation is:

[0064]

[0065] S2. the preparation of formula (I) compound:

[0066] Weigh (4-bromophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone 188mg, diphenylamine 101mg, sodium tert-butoxide 72mg, tri-tert-butylphosphine 30mg, [1,3-bis(2,6-diisopropylphe...

Embodiment 2

[0070] An aromatic amine derivative containing a benzophenone group has a molecular structure as shown in formula (II), named pBZ-TPA:

[0071]

[0072] The preparation method of the above-mentioned aromatic amine derivatives containing benzophenone group comprises the following steps:

[0073] S1. The preparation of (4-bromophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone is the same as in Example 1;

[0074] S2. the preparation of formula (Ⅱ) compound:

[0075] Weigh (4-bromophenyl)(3-phenylimidazo[1,2-a]pyridin-2-yl)methanone 188mg, 4-triphenylamine borate 235mg, 2mol / L sodium carbonate aqueous solution 3ml, four (Triphenylphosphine)palladium 40mg and 5mL of toluene were placed in a reaction tube, heated, stirred and refluxed for 12 hours under the protection of nitrogen at 120°C. After the reaction, the crude product was cooled, distilled, extracted, dried, concentrated, and separated; collected by cooling A yellow turbid liquid was obtained, the turbid liquid was...

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Abstract

The invention discloses an aromatic amine derivative containing a benzophenone group and its preparation method and application. The aromatic amine derivative containing a benzophenone group provided by the invention has a unique triphenylamine group and benzene The ketone group has TICT and AIE effects, high luminous intensity, and good hole transport ability, and can be used as a new type of soluble luminescent molecule with good performance, low cost, and highly distorted spatial structure. The aromatic amine derivatives can be widely used in the fields of color display and solid-state lighting for the preparation of light-emitting materials, light-emitting devices or smart materials. When used as OLEDs, the aromatic amine derivatives containing benzophenone groups are used as the main material , using the phosphorescent material as the guest material can reduce the concentration quenching of the phosphorescent material, improve the external quantum efficiency of the device, and reduce the efficiency roll-off.

Description

technical field [0001] The present invention relates to the technical field of organic luminescent materials, and more specifically, relates to an aromatic amine derivative containing benzophenone group and its preparation method and application. Background technique [0002] Organic electroluminescent device (OLED) is a new type of display technology with the characteristics of high brightness, low power consumption, fast response, high definition, good flexibility, and high luminous efficiency. It is widely used in smartphones, tablet computers, smart wearables, etc. Equipment and other high-tech fields. [0003] Most of the current commercial OLED materials are phosphorescent materials, because the phosphorescent emission of phosphorescent materials utilizes singlet and triplet excitons to achieve an internal quantum efficiency close to 100%. like etc. (Shen Z, Burrows P, SR, et al.Three-Color, Tunable, Organic Light-Emitting Devices.[J].Science, 1997,276(5321):2009-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06H01L51/50H01L51/54
CPCC07D471/04C09K11/06C09K2211/1014C09K2211/1044H10K85/631H10K85/6572H10K50/11
Inventor 霍延平周路陈文铖邱志鹏籍少敏杨庆旦
Owner GUANGDONG UNIV OF TECH
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