Spiral donor organic light-emitting small molecule material containing alkyl sulfur atom and its preparation method and application

A technology of alkyl sulfide and small molecules, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of complex preparation process and single light color, and achieve good bipolar transmission characteristics and high fluorescence quantum production rate, the effect of high horizontal orientation

Active Publication Date: 2020-12-22
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to overcome the shortcomings of existing organic luminescent materials containing a spiro structure, which have a single light color, basically green light, and the preparation process is complicated, the purpose of the present invention is to provide a spiro donor organic luminescent light containing an alkyl sulfur atom. Molecular materials, external quantum efficiency, and luminescent colors cover a wide range from blue light to sky blue light to green light, and can be applied to evaporation-type devices

Method used

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  • Spiral donor organic light-emitting small molecule material containing alkyl sulfur atom and its preparation method and application
  • Spiral donor organic light-emitting small molecule material containing alkyl sulfur atom and its preparation method and application
  • Spiral donor organic light-emitting small molecule material containing alkyl sulfur atom and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] This embodiment prepares intermediates 1 to 10 and compound P1:

[0052] The preparation steps of intermediate 1 (2-iodine 10H-spiro[acridine-9,9'-thioxanthene]) are as follows:

[0053]

[0054] Under a nitrogen atmosphere, 1.0 g (2.8 mmol) of spiro[acridine-9,9'-thioxanthene] and 0.63 g (2.8 mmol) of N-iodosuccinimide (NIS) were successively added to a 250 ml three-necked flask. , dichloromethane (DCM) 80 mL. Heated to 50°C and stirred for 24 hours in the dark. After the reaction, the solvent in the reaction system was suspended to dryness, extracted three times with dichloromethane and water, and the organic phase was taken. Dichloromethane was distilled off under reduced pressure, and purified by a silica gel column to obtain 0.95 g of the intermediate of structural formula 1, with a yield of 90%, C25H16INS, M / Z=489.37. m / z: 489.00 (100.0%), 490.01 (27.0%), 491.00 (4.5%), 491.01 (2.7%), 492.00 (1.2%); elemental analysis: C, 61.36; H, 3.30; I, 25.93; N , 2.86;...

Embodiment 2

[0087] Compound P2 (10-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-10H-spiro[acridine-9,9'- thioxanthene]), its structural formula and synthetic route are as follows:

[0088]

[0089] The specific implementation steps are:

[0090] Under a nitrogen atmosphere, 1.0 g (2.8 mmol) of 10H-spiro[acridine-9,9'-thioxanthene], 2-(3-bromophenyl)-4,6-diphenyl 1.1 g (2.8 mmol) of 1,3,5-triazine, 0.90 g sodium tert-butyl alkoxide, 59.8 mg palladium acetate and tri-tert-butylphosphine were added, heated to 110°C, and stirred for 24 hours in the dark. After the reaction, the solvent in the reaction system was suspended to dryness, extracted three times with dichloromethane and water, and the organic phase was taken. Dichloromethane was distilled off under reduced pressure, and purified by a silica gel column to obtain 1.45 g of the product of structural formula P2, with a yield of 80%. Molecular formula: C46H30N4S; M / Z=670.83 Theoretical value: m / z: 670.22 (100.0%), 671.22 (49.8%), 67...

Embodiment 3

[0092] This example prepares compound P3 (2-(9H-carbazol-9-yl)-10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl) -10H-spiro[acridine 9,9'-thia]), its structural formula and synthetic route are as follows:

[0093]

[0094] The specific implementation steps are:

[0095] Under a nitrogen atmosphere, 1.0 g (2.4 mmol) of the intermediate 3,2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 1.1 g was successively added to a 250 ml three-necked flask (2.8mmol), 0.90g of sodium tert-butyl alkoxide, and then add 59.8mg of palladium acetate and tri-tert-butylphosphine, heat to 110°C, and stir for 24 hours in the dark. After the reaction, the solvent in the reaction system was suspended to dryness, extracted three times with dichloromethane and water, and the organic phase was taken. Dichloromethane was distilled off under reduced pressure, and purified by a silica gel column to obtain 1.20 g of the product of structural formula P3, with a yield of 76%. Molecular formula: C58H37N5S; M / Z=...

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Abstract

The invention discloses a spiro donor organic luminescent small molecule material containing an alkyl sulfur atom. The spiro structure donor containing an alkyl sulfur atom and a triazine unit are used as the skeleton unit of the acceptor molecule. Other aromatic amine compounds are connected to the donor. The invention also discloses the preparation method and application of the organic luminescent small molecule material. The luminescent material of the present invention can realize intramolecular charge transfer, and its bipolar transport characteristics reduce the problem of carrier imbalance in unipolar luminescent materials, thereby simplifying the device structure and improving device performance. The molecular weight of the material is determined, the structure is single, and it has a high decomposition temperature and a low sublimation temperature, so it can be applied to organic light-emitting diodes; the light-emitting material of the present invention can not only As a high-efficiency blue light-emitting material in evaporation devices, it can also be used as a high-efficiency light-emitting material in non-doped solution processing devices.

Description

technical field [0001] The invention relates to the material technical field of organic electroluminescence device technology, in particular to a screw type donor organic light-emitting small molecule material containing an alkyl sulfur atom and a preparation method and application thereof. Background technique [0002] Organic electroluminescent devices have been applied in the field of light-emitting displays. Compared with polymer luminescent materials, small molecule luminescent materials have the advantages of simple preparation process, definite molecular weight, and single structure, so they have more potential to be promoted to wider commercial applications. At present, the technology of preparing organic electroluminescent devices with multilayer structure by vacuum evaporation or solution processing using small molecule materials is constantly developing and improving, and significant progress has been made. [0003] Conventional organic light-emitting materials w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D495/10C09K2211/1092C09K2211/1059C09K2211/1007C09K2211/1029H10K85/657H10K85/6572H10K50/11
Inventor 苏仕健徐志达何燕梅李彬彬
Owner SOUTH CHINA UNIV OF TECH
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