Indolocarbazole-based organic light-emitting material and preparation method and application thereof

A technology of indolocarbazole and luminescent materials, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low quantum efficiency, and achieve the effect of simple synthesis method, stable material structure and high yield

Inactive Publication Date: 2021-06-15
UNIV OF ELECTRONICS SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims at the problem of low quantum efficiency in organic electroluminescent devices existing in the above-mentioned prior art, and proposes an organic luminescent material based on indolocarbazole and its preparation method and application, based on indolo[3, 2-B]Carbazole as electron-donating core for the synthesis of various organic light-emitting materials

Method used

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  • Indolocarbazole-based organic light-emitting material and preparation method and application thereof
  • Indolocarbazole-based organic light-emitting material and preparation method and application thereof
  • Indolocarbazole-based organic light-emitting material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] This embodiment proposes an organic light-emitting material (p-TRZ-ICz) based on indolocarbazole, which has the structure shown below:

[0041]

[0042] The synthetic route of the organic luminescent material (p-TRZ-ICz) based on indolocarbazole is as follows:

[0043]

[0044] Specifically include the following steps:

[0045] Indolo[3,2-B]carbazole (0.256g, 1mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (0.814g, 2.1mmol), sodium tert-butoxide (0.288g, 3mmol) and palladium acetate (0.022g, 0.1mmol) were added to the reaction flask, pumped and ventilated three times, and tri-tert-butylphosphine (0.061g, 0.3 mmol), finally add 20mL toluene, heat up to 110°C, and react at this temperature for 12 hours. After the reaction was completed, the reaction solid was obtained by suction filtration, recrystallized using dichloromethane and methanol, and the final product p-TRZ-ICz was obtained by suction filtration, with a final yield of 93%.

[0046] This embodimen...

Embodiment 2

[0049] This embodiment proposes an organic light-emitting material (m-TRZ-ICz) based on indolocarbazole, which has the structure shown below:

[0050]

[0051] The synthetic route of the organic luminescent material (p-TRZ-ICz) based on indolocarbazole is as follows:

[0052]

[0053] Specifically include the following steps:

[0054] Indolo[3,2-B]carbazole (0.256g, 1mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (0.814g, 2.1mmol), sodium tert-butoxide (0.288g, 3mmol) and palladium acetate (0.022g, 0.1mmol) were added to the reaction flask, pumped and ventilated three times, and tri-tert-butylphosphine (0.061g, 0.3 mmol), finally add 20mL toluene, heat up to 110°C, and react at this temperature for 12 hours. After the reaction was completed, the reaction solid was obtained by suction filtration, recrystallized using dichloromethane and methanol, and the final product m-TRZ-ICz was obtained by suction filtration, with a final yield of 95%.

[0055] This embodimen...

Embodiment 3

[0058] This example proposes an organic light-emitting material (p-TXO-ICz) based on indolocarbazole, which has the structure shown below:

[0059]

[0060] The synthetic route of the organic luminescent material (p-TXO-ICz) based on indolocarbazole is as follows:

[0061]

[0062] Specifically include the following steps:

[0063] Indolo[3,2-B]carbazole (0.256g, 1mmol), 2-bromo-10-thiaxanthone (0.609g, 2.1mmol), sodium tert-butoxide (0.288g, 3mmol) and palladium acetate (0.022g, 0.1mmol) were added to the reaction flask, pumped and ventilated three times, tri-tert-butylphosphine (0.061g, 0.3mmol) was added under the protection of nitrogen, and finally 20mL of toluene was added, and the temperature was raised to 110°C. The reaction was carried out at this temperature for 12 hours. After the reaction was completed, the reaction solid was obtained by suction filtration, recrystallized using dichloromethane and methanol, and the final product p-TXO-ICz was obtained by suc...

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Abstract

The invention provides an indolocarbazole-based organic light-emitting material and a preparation method and application thereof, and belongs to the technical field of organic photoelectric materials. Indolo[3,2-b]carbazole is used as an electron donating core, two N atoms of the indolo[3,2-b]carbazole are respectively connected with the same acceptor groups, and the organic light-emitting material which has the characteristics that molecular structures among a plurality of donor groups and acceptor groups are distorted and has the thermal activation delayed fluorescence characteristic is synthesized. The preparation method comprises the following steps: adding indolo[3,2-b]carbazole, a halogenated acceptor compound, an organic alkali, a palladium catalyst and a phosphine ligand into toluene according to a certain molar ratio under the protection of nitrogen, conducting heating to 110-120 DEG C, conducting reacting for 10-14 hours, and carrying out suction filtration and recrystallization. The organic electroluminescent device using the organic luminescent material has theoretically 100% IQE and relatively high EQE, realizes efficient emission of blue light, green light and red light, and has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an indolocarbazole-based organic light-emitting material and its preparation method and application. Background technique [0002] Organic electroluminescent devices are a type of devices based on organic light-emitting materials that convert electrical energy into light energy. The cathode and anode are injected into the organic layer, and then meet in the light-emitting layer through the carrier transport layer, recombine to form excitons, and the excitons are in an excited state after being absorbed by organic molecules, and then emit light through radiative transitions. [0003] The organic light-emitting materials of organic electroluminescent devices can be divided into three generations at present, namely, the first-generation fluorescent materials, the second-generation phosphorescent materials and the third-generation thermally activat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/54
CPCC07D487/04C09K11/06C09K2211/1044C09K2211/1092C09K2211/1059H10K85/654H10K85/6576H10K85/6572
Inventor 郑才俊邢锦涛薛峥
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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