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Organic semiconductor material containing carbazole unit and synthesis

A technology of organic semiconductors and carbazole units, which is applied in the field of organic semiconductor materials containing carbazole units and its preparation, can solve the problems of limiting the application range of carbazole materials, achieve good evaporation performance, large modification space, and flexible routes Effect

Active Publication Date: 2008-03-12
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still no literature and patent reports on photoelectric functional materials modified with 1,8-carbazole as the core, which greatly limits the application range of carbazole materials in organic photoelectric materials.

Method used

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  • Organic semiconductor material containing carbazole unit and synthesis
  • Organic semiconductor material containing carbazole unit and synthesis
  • Organic semiconductor material containing carbazole unit and synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, compound material containing carbazole and pyrene:

[0045] 9-Ethyl-carbazole

[0046] 9-ethyl-9H-carbazole

[0047] Mix 5g carbazole, 3g KOH, and 30ml DMSO in a three-necked flask, add 4ml bromoethane dropwise under the condition of 85 degrees, stir for 3 hours, add 100ml water after cooling and mix, and leave a light yellow solid to precipitate, filter, After drying and recrystallization from absolute ethanol, the product was obtained as white needle crystals (yield 90%).

[0048] GC-MS (EI-m / z): 195 (M + ).

[0049] 3,6-di-tert-butyl-9-ethyl-carbazole

[0050] 3,6-di-tert-butyl-9-ethyl-9H-carbazole

[0051] Take 9-ethyl-carbazole (20mmol), 100mlCH 2 NO 3 , and zinc chloride (8.1g, 60mmol) were mixed in a three-neck flask, under nitrogen conditions, tert-butyl chloride (6.5ml, 60mmol) was added dropwise in the reaction flask, and after 5 hours of normal temperature reaction, 200ml The reaction was quenched with water, extracted with dichlorometha...

Embodiment 2

[0068] Embodiment 2, compound material containing carbazole and anthracene:

[0069] 10-bromoanthracene

[0070] 10-bromoanthracene

[0071] Anthracene (12.5mmol) was dissolved in DMF (17.42mL), and NBS (2.046g, 11.5mmol) was dissolved in DMF (21.78mL), and the mixture was added dropwise under ice water. After the addition, it was stirred at room temperature for 24 hours. Diluted with water, extracted with ether, dried and rotary evaporated, and purified with petroleum ether silica gel column to obtain a white solid (yield 88%).

[0072] GC-MS (EI-m / z): 280 (M + ).

[0073] 10-Anthraceneboronic acid

[0074] anthracen-10-yl-10-boronic acid

[0075]First, take 10-bromoanthracene (2.53mmol) and put it into a 250mL two-necked flask. The flask has been heat-dried and airtight, and then evacuated three times with nitrogen. Then, the reaction apparatus was put into a low temperature bath of -78°C generated by dry ice and acetone, and freshly distilled tetrahydrofuran (20 mL) w...

Embodiment 3

[0080] Embodiment 3, compound material containing carbazole and benzanthracene:

[0081] 10-Bromo-9-phenylanthracene

[0082] 10-bromo-9-phenylanthracene

[0083] Dissolve 9-phenylanthracene (1.5g, 5.9mmol) in acetic acid (80mL), heat to 65°C under nitrogen atmosphere, and add bromine (1.04g, 6.5mmol) dissolved in acetic acid (20mL) dropwise into the reaction flask. After the dropwise addition, the reaction was allowed to return to room temperature, crystals were precipitated, and filtered to obtain a yellow solid (92% yield).

[0084] GC-MS (EI-m / z): 280 (M + ), mp154°C.

[0085] 9-Phenylanthracene-10-yl-10-boronic acid

[0086] 9-phenylanthracen-10-yl-10-boronic acid

[0087] First, take 10-bromo-9-phenylanthracene (2.53mmol) and put it into a 250ml two-necked flask. The flask has been heated, dried and airtight, and then vacuumed three times with nitrogen. Oxygen device for processing use. Then, the reaction apparatus was put into a low temperature bath of -78°C gen...

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Abstract

The present invention provides an organic semiconductor material with a carbazole unit, a method of synthesizing an organic semiconductor material with a carbazole unit and the preparation method; the material in the category is applied in the field of the organic flat panel display, organic photovoltaic cell, organic optical storage, organic field effect tube, chemical and biological sensing and organic laser and other organic electronic fields. The material is a compound material with a substituted base introduced into the first and eighth levels of the carbazole unit, and has the structure as show in (A). The material has the advantages: (1) the synthesis is convenient and easily accessible and can be flexibly modified; (2) the material can effectively realize the modulation of the photoelectric nature of the material; and (3) the material has the high thermal stability and glass transition temperature, etc. Thus, the material can be expected to be a photoelectric functional material with the commercial potential.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to an organic semiconductor material containing a carbazole unit and a preparation method thereof, and relates to the application of these light-emitting materials in organic electroluminescence, organic field effect tubes, organic solar cells, organic light storage, organic nonlinear optics, chemical and biological transmission Sensitivity and organic lasers and other fields of application. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A. Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Bum, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (PolymericLight-emitting Diodes), organic flat panel display has become another generation of market-oriented dis...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D413/14C07D417/14C07D405/14C09K11/06H01L51/50H01L51/54H01L51/30H01L51/46H01L51/00
CPCY02E10/50Y02E10/549
Inventor 黄维解令海
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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