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Carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material, preparation method thereof and application of carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material in OLED

An organic semiconductor, near-ultraviolet light technology, applied in the fields of semiconductor/solid-state device manufacturing, luminescent materials, semiconductor devices, etc., can solve the problems to be developed, and achieve simple storage, high utilization rate of electrically excited excitons, and easy availability of raw materials. Effect

Pending Publication Date: 2022-03-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, near-UV / UV materials with a "hot excitonic" electroluminescence mechanism remain to be developed

Method used

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  • Carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material, preparation method thereof and application of carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material in OLED
  • Carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material, preparation method thereof and application of carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material in OLED
  • Carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material, preparation method thereof and application of carbazole-containing near ultraviolet light/ultraviolet light organic semiconductor material in OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Example 1: Carbazol-containing near-ultraviolet light / ultraviolet light organic semiconductor material 4-(2,7-bis(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)- The preparation of 3-methylbenzonitrile, the corresponding abbreviation of this substance is p-Cz-CNCz.

[0041]

[0042] The synthetic route is as follows:

[0043]

[0044] (1) Weigh 3-methyl-4-fluorobenzonitrile (5.06g, 37.5mmol), 2,7-dibromocarbazole (8.125g, 25mmol) and potassium carbonate (8.64g, 62.5mmol) into 250mL bis In a round-bottomed flask, after vacuuming, pass N 2 for protection. Afterwards, 60 mL of ultra-dry DMF was injected into the reaction flask, and the reaction was refluxed at 150° C. for 8 hours. After the reaction was completed, the mixture cooled to room temperature was poured into 200 mL of water, and the crude product was obtained by precipitation and filtration. Then it was separated and purified by silica gel column chromatography using PE / DCM as eluent to obtain a white int...

Embodiment 2

[0047] Example 2: Carbazole-containing near-ultraviolet / ultraviolet light organic semiconductor material 4-(9,9”-diphenyl-9H,9’H,9”H-[3,2’:7’,3”-tercarbazol ]-9'-yl)-3-methylbenzonitrile, the corresponding abbreviation of this substance is 3,6Cz-CNCz.

[0048]

[0049] The synthetic route is as follows:

[0050]

[0051] (1) Weigh 3-methyl-4-fluorobenzonitrile (4.05g, 30mmol), 2,7-dibromocarbazole (8.125g, 25mmol) and potassium carbonate (10.37g, 75mmol) into a 250mL double-mouthed circle In the bottom flask, after evacuating, pass N 2 for protection. Afterwards, 60 mL of ultra-dry DMF was injected into the reaction flask, and the reaction was refluxed at 140° C. for 10 hours. After the reaction was completed, the mixture cooled to room temperature was poured into 200 mL of water, and the crude product was obtained by precipitation and filtration. Then it was separated and purified by silica gel column chromatography using PE / DCM as eluent to obtain the white interme...

Embodiment 3

[0054] Embodiment 3: Preparation of carbazole-containing near-ultraviolet light / ultraviolet light organic semiconductor material 4-(2,7-di(naphthalen-2-yl)-9H-carbaz ol-9-yl)benzonitrile, which corresponds to Abbreviated as 2Na-CNCz.

[0055]

[0056] The synthetic route is as follows:

[0057]

[0058] (1) Weigh p-fluorobenzonitrile (3.63g, 30mmol), 2,7-dibromocarbazole (8.125g, 25mmol) and potassium carbonate (10.37g, 75mmol) into a 250mL double-necked round bottom flask, and vacuumize Back pass N 2 for protection. Afterwards, 60 mL of ultra-dry DMF was injected into the reaction flask, and the reaction was refluxed at 140° C. for 10 hours. After the reaction was completed, the mixture cooled to room temperature was poured into 200 mL of water, and the crude product was obtained by precipitation and filtration. Then it was separated and purified by silica gel column chromatography using PE / DCM as eluent to obtain a white intermediate 2Br-CNCz with a yield of 88%. ...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a near ultraviolet light / ultraviolet light organic semiconductor material containing carbazole, a preparation method of the near ultraviolet light / ultraviolet light organic semiconductor material and application of the near ultraviolet light / ultraviolet light organic semiconductor material in an OLED. Different modification groups are connected to a carbazole element to regulate and control the excited state property of a carbazole derivative, so that the organic semiconductor material has near ultraviolet light or ultraviolet light emission in a solid state and has remarkable heat exciton luminescence performance. The organic semiconductor material prepared by the invention can be used as a luminescent layer, and has the characteristics of high-efficiency solid-state luminescence and high electrical excitation utilization rate, so that a near ultraviolet light / ultraviolet light organic electroluminescent device which is excellent in electroluminescent performance, simple in structure and low in cost is obtained. The preparation method is simple, the raw materials are easy to obtain, the yield is high, the product structure is stable, and the preparation method has a wide application prospect in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of near-ultraviolet / ultraviolet organic semiconductor materials containing carbazole, a preparation method thereof, and an application in OLEDs. Background technique [0002] Organic Light Emitting Diode (OLED) is a type of device based on organic semiconductor materials that converts electrical energy into light energy. OLED has many advantages such as light and thin, low energy consumption, high contrast, self-illumination, flexible bending, etc., and is regarded as the most promising new generation display and lighting technology in the market. The comprehensive performance of OLED is directly related to the organic electroluminescent material used in its core functional layer, so the design and development of new and excellent organic electroluminescent materials has become a research hotspot in the field of OLED. [0003] In the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54
CPCC07D209/86C09K11/06C09K2211/1029C09K2211/1007C09K2211/1011H10K85/626H10K85/6572
Inventor 唐本忠王志明张翰黎刚刚郭学成
Owner SOUTH CHINA UNIV OF TECH
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