Electroluminescent materials using truxenone as electron acceptor and application of electroluminescent materials

A technology of tri-indanone and luminescent materials, which can be applied in the directions of luminescent materials, electric solid-state devices, circuits, etc., can solve the problems of high cost and limited development.

Active Publication Date: 2019-12-20
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most phosphorescent materials contain noble metals such as Ir and Pt, and their high cost limits their development.

Method used

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  • Electroluminescent materials using truxenone as electron acceptor and application of electroluminescent materials
  • Electroluminescent materials using truxenone as electron acceptor and application of electroluminescent materials
  • Electroluminescent materials using truxenone as electron acceptor and application of electroluminescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Dissolve 5-Br-1-indanone (2.00g, 9.5mmol) in 30ml of chloroform, and slowly add liquid bromine (3.04g, 19.0mmol) dropwise under vigorous stirring, and continue stirring for 1h, then continuously introduce Nitrogen for 1 h, after the reaction, the residual solvent was removed in vacuo, and the solid crude product was recrystallized with a small amount of methanol to obtain the light yellow intermediate 2,2,5-tribromo-1-indanone N (2.91 g, 83%).

[0029] 2,2,5-Tribromo-1-indanone (3.00g, 8.1mmol) was kept in a 25ml round bottom flask at a high temperature of 220°C and continuously stirred until no gas escaped, the mixture was cooled to room temperature and dispersed in 25ml di In methyl chloride, it was filtered after being treated with supernatant for 5 minutes. The crude product was washed twice with 25 ml of dichloromethane, dried and recrystallized with nitrobenzene to obtain light yellow intermediate M (1.51 g, 30%).

[0030]

[0031] Intermediate M (2...

Embodiment 2

[0033]

[0034]Intermediate M (2.00g, 3.2mmol) was added to a three-necked flask, and then 1,3,6,9-tetramethylcarbazole (0.858g, 3.84mmol) and palladium acetate (36.2mg, 0.161mmol) were added , Potassium tert-butoxide (0.723g, 6.44mmol), tri-tert-butylphosphine tetrafluoroborate (140.2mg, 0.483mmol), and then add 30mL of toluene as a solvent, under the protection of nitrogen, heat to 110°C and react for 24h. After the reaction, the reaction solution was poured into saturated sodium chloride solution, extracted with dichloromethane (3 × 20mL) to combine the organic layers, and dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the crude product was separated by column chromatography to obtain Target product (TR2) as yellow solid. Yield 59%, MALDI-TOF-MS: 1048.2994 [M + ].

Embodiment 3

[0036]

[0037] The obtained intermediate M (2.00g, 3.2mmol) was added to a three-necked flask, and then 3,6-di-tert-butylcarbazole (1.073g, 3.84mmol), palladium acetate (36.2mg, 0.161mmol) were added, Potassium tert-butoxide (0.723g, 6.44mmol), tri-tert-butylphosphine tetrafluoroborate (140.2mg, 0.483mmol), and 30mL of toluene were added as a solvent, heated to 110°C under nitrogen protection, and reacted for 24h. After the reaction, the reaction solution was poured into saturated sodium chloride solution, extracted with dichloromethane (3×15mL) and dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the crude product was separated by column chromatography to obtain the target product as a yellow solid (TR3). Yield 64%, MALDI-TOF-MS: 1216.6226 [M + ].

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Abstract

The invention provides electroluminescent materials using truxenone as an electron acceptor and an application of the electroluminescent materials, and belongs to the field of organic electroluminescence. The derivatives use the truxenone as the electron acceptor, and carbazole, 1,3,6,9-tetramethylcarbazole, 3,6-di-tert-butylcarbazole, 3-carbazolylcarbazole, 9,9-dimethylacridine, phenoxazine and phenothiazine as electron donors. A synthetic method of the series of compounds comprises the following steps: performing a coupling reaction by using 5-bromo-1-indenone as a raw material, performing an oxidation reaction, and performing a Buchwald-Hartwig coupling reaction to obtain the truxenone substituted by different electron donor groups. The series of compounds have strong absorption in theultraviolet-visible light regions, a dilute solution of the compounds emits strong fluorescence, the emitting color is orange-red or red, and the compounds can be used as light-emitting materials to be applied to organic light-emitting diodes.

Description

technical field [0001] The invention relates to a preparation method of triindanone derivatives and an electroluminescent application thereof, belonging to the field of organic electroluminescence. Background technique [0002] The development of information technology in the new century is changing with each passing day. Efficient and accurate information collection, fast information processing, high-density information storage, large-capacity information transmission and high-definition information display are the goals people pursue, and information display technology plays an extremely important role. [0003] Currently, relatively mature displays include cathode ray tube (Cathode Ray Tube, CRT), plasma display (Plasma Display Panel, PDP) and liquid crystal display (Liquid Crystal Display, LCD). Although they have irreplaceable excellent performance in a certain period of time, these display devices have defects in varying degrees, making their applications unable to me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D219/02C07D265/38C07D279/22C09K11/06H01L51/50H01L51/54
CPCC07D209/86C07D219/02C07D265/38C07D279/22C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037H10K85/624H10K85/657H10K85/6572H10K50/12Y02P20/55
Inventor 刘迪李欣
Owner DALIAN UNIV OF TECH
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