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A small molecule luminescent material based on triple spiro acridine donor unit and its preparation method and application

A triple-spiro acridine, luminescent material technology, applied in luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve problems such as lack of thermally activated delayed fluorescent materials, etc. Output coupling constant, good reproducibility

Active Publication Date: 2021-07-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ultra-high-efficiency heat-activated delayed fluorescent materials are still rare, especially high-efficiency blue and deep blue materials.

Method used

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  • A small molecule luminescent material based on triple spiro acridine donor unit and its preparation method and application
  • A small molecule luminescent material based on triple spiro acridine donor unit and its preparation method and application
  • A small molecule luminescent material based on triple spiro acridine donor unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of a non-conjugated end group containing a heteroatom sulfur-containing triple spiro acridine donor unit (a) of this embodiment:

[0059] (1) Preparation of intermediate 1-1:

[0060] After adding (2-bromophenyl)(phenyl)sulfane (5.3 g, 20 mmol) into a 250 mL three-necked flask, 150 mL of dry tetrahydrofuran was added. The mixture solution was cooled to -78°C and then degassed for 20 minutes. After that, 8.8 mL of n-butyllithium (2.5 mmol mL -1 ), kept stirring at -78°C for 1 hour, dissolved anthracene-9,10-dione (3.33g, 16mmol) in 50mL of anhydrous tetrahydrofuran, and added dropwise to the above low-temperature solution with a syringe. After the dropwise addition, continue to stir at this temperature for 1 hour, then raise the temperature to room temperature and stir for 4 hours. Then the mixture solution was treated with 5mL methanol and 10mL dilute hydrochloric acid (1mmolmL -1 ) was quenched, and then 100 ml of deionized water was added. And extract...

Embodiment 2

[0076] The preparation of a non-conjugated end group containing fluorene unit triple spiro acridine donor unit (b) of this embodiment:

[0077] (1) Preparation of intermediate 2-1:

[0078] After adding 2-bromo-1,1'-biphenyl (4.7 g, 20 mmol) into a 250 mL three-necked flask, 150 mL of dry tetrahydrofuran was added. The mixture solution was cooled to -78°C and then degassed for 20 minutes. After that, 8.8 mL of n-butyllithium (2.5 mmol mL-1 ), kept stirring at -78°C for 1 hour, dissolved anthracene-9,10-dione (3.33g, 16mmol) in 50mL of anhydrous tetrahydrofuran, and added dropwise to the above low-temperature solution with a syringe. After the dropwise addition, continue to stir at this temperature for 1 hour, then raise the temperature to room temperature and stir for 4 hours. Then the mixture solution was treated with 5mL methanol and 10mL dilute hydrochloric acid (1mmolmL -1 ) was quenched, and then 100 ml of deionized water was added. And extracted three times with dich...

Embodiment 3

[0094] Preparation of a triple-spiro acridine donor unit (c) whose end group contains a non-conjugated sulfone group in this embodiment:

[0095] The reaction equation is as follows:

[0096]

[0097] Intermediate (a) (1.05 g, 2 mmol) was dissolved in 150 ml of glacial acetic acid and purged with nitrogen for 20 minutes. Finally, the mixture solution was heated to 80° C., stirred for 10 minutes, and then 5 ml of hydrogen peroxide was added. The reaction was carried out at this temperature for 8 hours. The reaction was stopped, and the glacial acetic acid solvent was distilled off under reduced pressure. Column chromatography petroleum ether / dichloromethane (2:1) obtained a light yellow solid EI-MS (m / z): calcdfor C 38 h 25 NSO 2 ; Molecular weight: 559.16; found: 559.32, [M + ].

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Abstract

The invention discloses a small molecule luminescent material based on a triple-spiro acridine donor unit, a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. The luminescent material of the present invention contains a triple-spiro acridine donor unit, has a single material structure, a certain amount of material, is easy to purify, has good reproducibility in multiple synthesis, and has very high thermal stability and shape stability. The small molecule luminescent material based on triple spiro acridine donor unit of the present invention is applied to organic photoelectric devices, compared with the small molecule electroluminescent material composed of double spiro acridine donor unit, based on triple spiro acridine The donor material can obtain higher horizontal dipole orientation, higher device efficiency and bluer light color, and obtain higher device efficiency in a wider doping ratio, thus having a wider application prospect , for example, higher efficiency can be obtained in non-doped devices, and can be applied to pure delayed fluorescence white light devices, etc.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a small molecule luminescent material based on a triple spiro acridine donor and its preparation and application. Background technique [0002] In traditional organic small molecule fluorescent materials, since 75% of the triplet excitons are spin-forbidden, radiative luminescence cannot occur, so only 25% of the singlet excitons can emit light, and the luminous efficiency is low. In contrast, organic phosphorescent materials based on metal complexes such as iridium and platinum can achieve 100% internal quantum efficiency through spin-orbit coupling. However, due to the limited resources of iridium, platinum and other metals, the problems of high price, low color purity and short life of blue phosphorescent materials cannot be solved for a long time, which limits the application of organic phosphorescent materials. Therefore, for the long-ter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D495/10C07D401/10C07D411/04C07D409/04C07D221/20C07D491/107C07D471/10H01L51/50H01L51/54
CPCC09K11/06C07D495/10C07D401/10C07D411/04C07D409/04C07D221/20C07D491/107C07D471/10C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/1088C09K2211/1014H10K85/654H10K85/657H10K85/6576H10K85/6572H10K50/00Y02B20/00
Inventor 苏仕健李伟李彬彬
Owner SOUTH CHINA UNIV OF TECH
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