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1,8-carbazoles polymer photovoltaic material, preparation and use method thereof

A technology of optoelectronic materials and polymers, applied in the fields of luminescent materials, chemical instruments and methods, photovoltaic power generation, etc., can solve the problem of no patent reports on polymer materials

Active Publication Date: 2011-08-03
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 is no patent report on the polymer material formed by the structural unit formed by the 1 and 8 positions of carbazole

Method used

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  • 1,8-carbazoles polymer photovoltaic material, preparation and use method thereof
  • 1,8-carbazoles polymer photovoltaic material, preparation and use method thereof
  • 1,8-carbazoles polymer photovoltaic material, preparation and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1, preparation of poly(1,8-carbazole) homopolymer material:

[0056] 9-Ethyl-carbazole

[0057] Mix 5g carbazole, 3g KOH, and 30ml DMSO in a three-necked flask, add 4ml of bromoethane dropwise at 85°C, stir for 3 hours, add 100ml of water after cooling, and leave to stand for a light yellow solid to precipitate, filter, After drying and recrystallization from absolute ethanol, the product was obtained as white needle crystals (yield 90%).

[0058] GC-MS (EI-m / z): 195 (M + ).

[0059] 3,6-di-tert-butyl-9-ethyl-carbazole

[0060] Take 9-ethyl-carbazole (20mmol), 100mlCH 2 NO 3 Mix it with zinc chloride (8.1g, 60mmol) in a three-necked flask, and add tert-butyl chloride (6.5ml, 60mmol) dropwise to the reaction flask under nitrogen gas. After reacting at room temperature for 5 hours, add 200ml of water The reaction was quenched, extracted with dichloromethane, dried, and rotary evaporated to obtain a white product (yield 94%).

[0061] GC-MS (EI-m / z): 307 ...

Embodiment 2、1

[0070] Embodiment 2, 1,8-carbazole and 1,4-benzene unit copolymer material preparation:

[0071] 1,4-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolanyl)-benzene

[0072] First, take 1,4-dibromo-benzene (1.0 equiv.) and put it into a 250ml two-necked flask. The flask has been heated, dried and airtight, and then evacuated three times with nitrogen. Oxygen device for processing use. Then, the reaction apparatus was placed in a -78°C low temperature bath generated by dry ice and acetone, and freshly distilled tetrahydrofuran (20 ml) was taken anhydrous and oxygen free. Then n-butyllithium (3.0 equiv.) was slowly added to the two-necked flask, and reacted at a low temperature of -78°C for about 1 hour. Finally, 2-isopropoxy-4,4,5,5- Tetramethyl-1,3,2-dioxaborane (3.0 equiv.) was quickly injected into the reactor, and the reaction was slowly returned to room temperature, and the reaction was carried out overnight. After the reaction was completed, the reaction was quenched with ice w...

Embodiment 3、1

[0076] Example 3, 1,8-carbazole and 9,9-dioctylfluorene unit random copolymer material preparation:

[0077] 2,2'-(9,9-di-n-octanefluorene-2,7-diyl)-bis([1,3,2]dioxaborinane)

[0078] Magnesium turnings (2.1 quiv.) and a little crystalline iodine were added to a 250 ml four-neck flask equipped with a reflux condenser and dropping funnel, which had been heat-dried and purged with nitrogen by evacuation. First, 1 ml of a solution of 2,7-dibromo-9,9-n-octanefluorene (1 equiv.) dissolved in tetrahydrofuran (10 ml) was added dropwise as quickly as possible, and the mixture was heated at the dropping site. After the reaction started, the remaining solution was slowly added dropwise, and the rate of addition was based on the automatic boiling of the reaction mixture. Tetrahydrofuran (ca. 1.101) was then added and the mixture was refluxed for 2h. The resulting clear Grignard solution was then cooled to room temperature and slowly added dropwise to an excess of freshly distilled trii...

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Abstract

The present invention discloses a 1, 8-carbazole type polymer photovoltaic material and preparation and application methods thereof, relating to a type of polymer materials which comprise special carbazole units, and also relates to the application of the materials in the fields such as organic electrofluorescence, organic field effect transistors, organic solar cells, nonlinear optics, bio-sensing, organic optical storage and organic laser, and the like. The type of materials can be applied to the organic electronic fields such as organic flat panel display, organic photovoltaic cells, organic optical storage, organic field effect transistors and organic laser, and the like. The type of polymer materials has 1, 8-carbazole unit skeletons. The polymer materials have the advantages that: (1) 1,8-carbazole monomers are easy for synthesis and obtaining, and a series of homopolymers and copolymers are prepared; (2) non-linear skeleton structures and non-planar conformations are provided; and (3) high hot stability and glass transition temperature and the like are provided. Electrofluorescence devices which are prepared by the materials obtain satisfactory results in the aspects of brightness and luminous efficiency, and the like, so the types of materials can become photovoltaic materials with low cost and commercial potential.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a class of polymer materials containing special carbazole units, and relates to the application of such materials in organic electroluminescence, organic field effect tubes, organic solar cells, nonlinear optics, biosensing, organic optical storage and organic lasers, etc. field applications. 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.; Burn, 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 display products after liquid crystal display. At the same time, other organic electronics and opto...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06H01B1/12H01L51/00H01L51/50H01L51/54H01L51/30H01L51/46
CPCY02E10/549
Inventor 黄维刘冉冉解令海石乃恩
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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