Preparation method and application method of 4-9, 9-diaryl fluorene polymer material containing substituted radical

A polymer material, the technology of diaryl fluorene, which is applied in 9 fields, can solve the problem that the fluorene structural unit is rarely reported, and achieves the effect of mild conditions and simple synthesis steps.

Inactive Publication Date: 2010-01-13
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on 9,9-diarylfluorene structura

Method used

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  • Preparation method and application method of 4-9, 9-diaryl fluorene polymer material containing substituted radical
  • Preparation method and application method of 4-9, 9-diaryl fluorene polymer material containing substituted radical
  • Preparation method and application method of 4-9, 9-diaryl fluorene polymer material containing substituted radical

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, poly(4-octyloxy-9,9-diphenylfluorene)

[0043] Poly(4-(octyloxy)-9, 9-diphenyl-9H-fluorene)

[0044] 6H-3,8-Dibromobenzopyran-6-one

[0045] 3,8-dibromo-6H-benzo[c]chromen-6-one

[0046] Experimental procedure: 2 g (5.92 mmol) of 2,7-dibromofluorenone and 11.83 ml of trifluoroacetic acid were mixed in a two-necked flask. Under the condition of ice-water bath, add Na every 10 minutes 2 CO 4 0.25g, five times in total. Return to room temperature and stir for 48 hours. The reaction was quenched with 40ml of ice water and extracted with dichloromethane (3×30ml). Washed with 10% NaHCO3, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:1) to obtain a white solid (yield 70%).

[0047] 2'-(Hydroxydiphenylmethyl)-4,4'-dibromobiphenyl-2-ol

[0048] 4,4'-dibromo-2'-(hydroxydiphenylmethyl)biphenyl-2-ol

[0049] Experimental procedure: get bromo-benzene (15mmol) and magnesium (0.36g, 1...

Embodiment 2

[0059] Example 2, poly-{[2,7-(9,9-spirobifluorene)]-2,7-[4-(octyloxy)-9,9-diphenyl-9H-fluorene]}

[0060] poly-{[2,7-(9,9'-spirobi[fluorene])]-2,7-[4-(octyloxy)-9,9-diphenyl-9H-fluorene]}

[0061] Experimental procedure: Take 2,7-dibromo-4-octyloxy-9,9-diphenylfluorene (0.302g, 0.5mmol, 1equiv) and 9,9-spirobifluorene-2,7-diboronic acid butyl The base ester (0.242g, 0.5mmol, 1equiv) is mixed and dissolved in the mixed solvent of 20ml toluene and tetrahydrofuran, and the catalyst Pd(PPh 3 ) 4 (1-5mol%). Protect from light and pass through nitrogen, then add K 2 CO 3 (1mL, 2mol / L, 2equiv.), react at 90°C for 48 hours, add water after the reaction, use CHCl 3 Extract, dry and concentrate by rotary evaporation, and put into 100mL of methanol. The collected solid was extracted and purified in methanol for 3 days, and reprecipitated in methanol to obtain 0.278 g of a powdery product. GPC: M n = 17 250; PDI = 2.5.

Embodiment 3

[0062] Example 3, poly-{[2,7-(9,9-diphenyl-9H-fluorene)]-2,7-[4-(octyloxy)-9,9-diphenyl-9H- Fluorene]}poly-{[2,7-(9,9-diphenyl-9H-fluorene)]-2,7-[4-(octyloxy)-9,9-diphenyl-9H-fluorene]}

[0063] Experimental procedure: take 2,7-dibromo-4-octyloxy-9,9-diphenylfluorene (0.302g, 0.5mmol, 1equiv) and 9,9-diphenylfluorene-2,7-diboronic acid Butyl ester (0.242g, 0.5mmol, 1equiv) was mixed and dissolved in a mixed solvent of 20ml toluene and tetrahydrofuran, and the catalyst Pd(PPh 3 ) 4 (1-5mol%). Protect from light and pass through nitrogen, then add K 2 CO 3 (1mL, 2mol / L, 2equiv.), react at 90°C for 48 hours, add water after the reaction, use CHCl 3 Extract, dry and concentrate by rotary evaporation, and put into 100mL of methanol. The collected solid was extracted and purified in methanol for 3 days, and reprecipitated in methanol to obtain 0.271 g of a powdery product. GPC: M n = 19 550; PDI = 1.9.

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Abstract

The invention relates to a preparation method and an application method of a 4-9, 9-diaryl fluorene polymer material containing a substituted radical, belonging to the field of photoelectric material and organic information display science, in particular to a 4-9, 9-diaryl fluorene homopolymerize or copolymerization conjugated polymer containing the substituted radical and a preparation method thereof. The 4-9, 9-diaryl fluorene homopolymerize or copolymerization conjugated polymer containing the substituted radical is applied to organic electronic fields, such as organic light emission display, and the like, and has a structure as above. The polymer material keeps high heat stability, glass transition temperature, and the like and can be anticipated to become a polymer blue-light material with commercialized potential.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a 9,9-diaryl fluorene polymer material containing substituent groups at the 4-position and its preparation method, and relates to the application of these materials in organic electroluminescence, organic light storage, organic field effect tubes, organic solar cells, Applications in organic nonlinear optics, chemical and biological sensing, and organic lasers. 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 display products after ...

Claims

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Application Information

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IPC IPC(8): C08G61/02C09K11/06H01L51/50H01L51/52H01L51/54
Inventor 解令海黄维张龙林宗琼钱妍
Owner NANJING UNIV OF POSTS & TELECOMM
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