Indanone quinoxaline derivative as well as preparation method and application thereof

A derivative and quinoxaline technology, applied in the field of indanonequinoxaline derivatives and their preparation, can solve the problem that the efficiency of red light materials does not reach the height of luminescent materials, and achieve easy sublimation purification, good electrochemical stability, The effect of optimizing material properties

Active Publication Date: 2021-10-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the luminous efficiency of blue and green light based on thermally activated delayed fluorescence is close to the commercial level, but the efficiency of red light materials is far from reaching the height of commercial second-generation noble metal complex luminescent materials.

Method used

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  • Indanone quinoxaline derivative as well as preparation method and application thereof
  • Indanone quinoxaline derivative as well as preparation method and application thereof
  • Indanone quinoxaline derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0064] The preparation chemical reaction formula and experimental steps of intermediate M1 are as follows:

[0065]

[0066] 1.43 g of 1H-indene-1,2,3-trione hydrate (8 mmol) and 2.13 g of 4,5-dibromobenzene-1,2-diamine (8 mmol) were dissolved in 80mL of acetic acid, and then heated to 80°C under reflux for 8 hours. After the reaction was cooled to room temperature, the resulting mixture was filtered to remove the solvent, and then the crude product was purified by silica gel column chromatography and dried under vacuum to finally obtain the product intermediate M1 with a yield of 54.8%. Product Molecular Formula: C 15 h 6 Br 2 N 2 O; molecular weight m / z: 389.88. The obtained product was subjected to an elemental analysis test, and the elemental analysis results were: C, 46.19; H, 1.55; Br, 40.97; N, 7.18; O, 4.10, and the elemental analysis results were in line with the theoretical value of the product. The product obtained was identified as M1.

[0067] The prepar...

Embodiment 1

[0075] The chemical reaction formula for preparing compound 1 in this embodiment is as follows, and its specific experimental steps are as follows:

[0076]

[0077] Intermediate M1 (1.14mmol, 445mg) and 4-(carbazol-9yl) phenylboronic acid pinacol ester (2.85mmol, 1052mg) were dissolved in K 2 CO 3 aqueous solution in a 250mL round bottom flask. After another 15 min with argon, the catalyst Pd(PPh 3 ) 4 (0.057 mmol, 66 mg), and then sparged with argon for 10 minutes. The reaction was then heated to 85°C and stirred vigorously for 12 hours. After cooling the reaction system to room temperature, the solvent was removed by vacuum rotary evaporator, and the mixture was extracted 3 times with dichloromethane (DCM). The collected organic phase was further washed three times with deionized water, and finally the organic phase was washed with anhydrous magnesium sulfate (MgSO 4 )dry. The next step was purified by silica gel column chromatography to finally obtain the product...

Embodiment 2

[0079] The chemical reaction formula for preparing compound 2 in this embodiment is as follows, and its specific experimental steps are as follows:

[0080]

[0081] Compared with Example 1, the difference is that 4-(carbazol-9 base) phenylboronic acid pinacol ester is replaced with equivalent triphenylamine-4-boric acid pinacol ester, and other raw materials and steps are the same as Example 1, the product compound 2 was finally obtained with a yield of 76%. Product Molecular Formula: C 51 h 34 N 4 O; molecular weight m / z: 718.27. The obtained product was subjected to an elemental analysis test, and the elemental analysis results were: C, 85.21; H, 4.77; N, 7.79; O, 2.23, and the elemental analysis results were in line with the theoretical value of the product. The product obtained was identified as compound 2.

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Abstract

The invention discloses an indanone quinoxaline derivative as well as a preparation method and application thereof. The indanone quinoxaline derivative disclosed by the invention takes an indanone quinoxaline group as an electron acceptor and an aromatic amine group as an electron donor, and the organic small molecule has the advantages of single structure, simplicity in purification and stable yield; and the organic small molecule derivative has a thermally activated delayed fluorescence property, can form an organic thin film through vacuum evaporation or spin coating, and is applied to organic photoelectric devices including organic light emitting diodes and the like. The indanone quinoxaline derivative has important significance for developing novel organic photoelectric materials with low cost and good performance.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to an indenoquinoxaline derivative and a preparation method and application thereof. Background technique [0002] Organic electroluminescent (OLED) devices have attracted extensive attention due to their applications in solid-state lighting and flexible displays. The light-emitting materials commonly used in OLED can be divided into two types of material systems: organic small molecules and organic polymer light-emitting materials. Compared with polymer light-emitting materials, organic small molecules have simple synthesis and preparation, clear and stable structures, and high material purity, so they can be obtained. Higher device performance and better stability. At present, red, green and blue primary color display devices based on organic small molecule light-emitting materials have been successfully commercialized. However, due to the high cost of material prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/14C07D413/14C07D417/14C07D421/14C07D241/38C09K11/06H01L51/54H01L51/50
CPCC07D403/14C07D241/38C07D401/14C07D413/14C07D417/14C07D421/14C09K11/06C09K2211/1044C09K2211/1029C09K2211/1007C09K2211/1014C09K2211/1033C09K2211/1037C09K2211/104H10K85/631H10K85/6572H10K85/657H10K50/11
Inventor 苏仕健谢文韬刘坤坤李梦珂彭晓媚
Owner SOUTH CHINA UNIV OF TECH
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