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Hindered amine end capped conjugated molecular material, and its preparing method and use

A technology of conjugated molecules and hindered amines, which is applied in the field of hindered amine-terminated oligomers and polymer materials and their preparation, and can solve the problems of lack of literature and patent reports

Inactive Publication Date: 2006-03-08
FUDAN UNIV
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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 the strategy and research of introducing hindered amine structural units into organic electronic materials.

Method used

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  • Hindered amine end capped conjugated molecular material, and its preparing method and use
  • Hindered amine end capped conjugated molecular material, and its preparing method and use
  • Hindered amine end capped conjugated molecular material, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1, Suzuki coupling reaction to prepare hindered amine-terminated poly(9,9-dioctylfluorene)

[0077] 2,2,6,6-Tetramethylpiperidin-4-yl 4-bromobenzyl ester

[0078] 2,2,6,6-tetramethylpiperidin-4-yl4-bromobenzoate

[0079] Dissolve 2,2,6,6-tetramethylpiperidine (8g, 2equiv.) in a 250ml two-necked reaction flask by adding 60ml tetrahydrofuran to dissolve, add molecular sieve catalyst (4g), and add triethylamine (15ml) Mix well; add 4-bromobenzoyl chloride (lequiv.) slowly under ice water cooling, react for half an hour, then add to 70°C and react at this temperature for 5 hours. After the reaction, the molecular sieves were filtered off, washed with water, extracted with dichloromethane, dried and rotary evaporated, and purified with ethyl acetate silica gel column to obtain a colorless liquid (51% yield).

[0080] GC-MS (EI-m / z): 339 (M + ). 1 H NMR (400MHz, CDCl 3 , ppm): δ7.882-7.861 (d, J=8.4Hz, 2H), 7.57-7.548 (d, J=7.6Hz, 2H), 5.457-5.379 (s, 1H), 2.054-...

Embodiment 2

[0091] Example 2, Suzuki coupling reaction to prepare hindered amine-terminated poly(9,9-dioctylfluorene)

[0092] 4-(4-Bromophenylene ether) 2,2,6,6-tetramethylpiperidine

[0093] 4-(4-bromophenoxy)-2,2,6,6-tetramethylpiperidine

[0094]Get 1,4-dibromobenzene (10mmol) and mix 30ml toluene, and mix it with 2,2,6,6-tetramethylpiperidin-4-ol (10mmol) and 20ml toluene; Potassium hydroxide 0.79 g (14mmol) and 18-crown ether-6 (0.6mmol, 5mol%), mixed and stirred and heated for 2 hours at 80°C, after the reaction was completed, cooled to room temperature, filtered off the solid, and rotary evaporated toluene under reduced pressure to obtain the crude product . Purify by silica gel column, eluent n-hexane / acetone (2:8), yield: 70%.

[0095] GC-MS (EI-m / z): 311 (M + ). 1 H NMR (400MHz, CDCl 3 , ppm): δ7.661-7.640 (d, J=8.4Hz, 2H), 7.52-7.543 (d, J=7.6Hz, 2H), 5.121-5.071 (s, 1H), 2.054-2.012 (dd, 2H ), 1.315-1.179(d, 14H).

[0096] Hindered amine-terminated poly(9,9-dioctylflu...

Embodiment 3

[0100] Example 3, Yamamoto coupling reaction to prepare hindered amine-terminated poly(9,9-dioctylfluorene)

[0101] Hindered amine-terminated poly(9,9-dioctylfluorene)

[0102] poly(9,9-dioctylfluorene)

[0103] Under nitrogen protection, 2,7-dibromo-9,9-n-octane fluorene (lequiv.) and 4-(4-bromophenyl ether group) 2,2,6,6-tetramethylpiperidine ( 0.1 equiv.) was dissolved in 30 ml of tetrahydrofuran solution and heated to 60°C. Under the protection of high-purity nitrogen, it was quickly added to a round bottom flask containing 820 mg of Ni(COD), 470 mg of bipyridine and 0.4 ml of 1,5-cyclooctadiene (COD). The polymerization takes place immediately at reflux for 3 days, then, cooling, suction filtration and washing with THF, dilute hydrochloric acid and water. Finally, a Soxhlet tube extraction device was used to extract a soluble polymer with 200 ml of acetone, and then a light yellow high polymer was obtained through re-precipitation. (75% yield).

[0104] GPC: M n =8...

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Abstract

This invention relates to a conjugated molecular material using retardant amine structural unit as blocking agent and preparing method thereof. Said material comprises the two parts of organic conjugated frameworm chain and blocking structure retardant amine. The material can be used as organic material or stabilizer with high stability to oxygen, heat and ultraviolet light, or carrier transmission material, luminescent material and conductive material which can be used to the organic electronic fields such as organic EL device, photovoltaic cell, organic filed effect tube, fluorescent sensor and laser etc..

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a hindered amine-terminated oligomer and polymer material and a preparation method thereof, and relates to the application of these luminescent materials in organic electroluminescence, organic field effect tubes, organic solar cells, organic nonlinear optics, biosensing and organic Applications in laser and other fields. 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 (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, oth...

Claims

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Application Information

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IPC IPC(8): C08F8/00C09K11/06C09K9/00H05B33/14
Inventor 黄维解令海彭波司三民
Owner FUDAN UNIV
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