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Organic electronic material containing hindered amine group and spiro structure unit and its synthesis process

A technology of organic electronic materials and structural units, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of lack of literature and patent reports

Inactive Publication Date: 2005-09-28
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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  • Organic electronic material containing hindered amine group and spiro structure unit and its synthesis process
  • Organic electronic material containing hindered amine group and spiro structure unit and its synthesis process
  • Organic electronic material containing hindered amine group and spiro structure unit and its synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Embodiment 1, Suzuki coupling reaction prepares hindered amine-containing monomer and its oligomer: two (2,2,6,6-tetramethylpiperidin-4-yl) 6,6'-[2,5 -Bis(-9,9'-spirobifluoren-2-yl)-1,4-benzenedi(oxo)]dihexanoate

[0131] 2,2,6,6-Tetramethylpiperidin-4-yl 6-bromohexanoate

[0132] 2,2,6,6-tetramethylpiperidin-4-yl 6-bromohexanoate

[0133]

[0134] 2,2,6,6-Tetramethylpiperidine (8g, 2equiv.) was dissolved in a 250ml two-neck reaction flask and 60ml of tetrahydrofuran was added for dissolution, molecular sieve catalyst (4g) was added, and triethylamine (15ml) was added Mix well; add 6-bromohexanoyl chloride (1 equiv.) slowly under ice-water cooling, react for half an hour, then add to 70°C and react at this temperature for 12 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). GC-M...

Embodiment 2

[0147] Embodiment 2, Suzuki coupling reaction prepares hindered amine-containing monomer and its oligomer: two (1,2,2,6,6-pentamethylpiperidin-4-yl) 6,6'-[2 , 5-bis(-9,9'-spirobifluoren-2-yl)-1,4-benzenedi(oxyl)]dihexanoate

[0148] 2,2,6,6-Pentamethylpiperidin-4-yl 6-bromohexanoate

[0149] 1,2,2,6,6-pentamethylpiperidin-4-yl 6-bromohexanoate

[0150]

[0151] 1,2,2,6,6-Pentamethylpiperidine (8g, 2equiv.) (n-BuLi, 66.72mL, 106.75mmol, 1.6mol / LinHexane, 1equiv.) was dissolved in a 250ml two-neck reaction Add 60ml of tetrahydrofuran to the bottle to dissolve, add molecular sieve catalyst (4g), and add triethylamine (15ml) to mix thoroughly; under the condition of ice water cooling, slowly add 6-bromohexanoyl chloride (1equiv.), react for half an hour, and then Added to 70°C and reacted at this temperature for 12 hours. After the reaction, the molecular sieves were filtered out, washed with water, extracted with dichloromethane, dried and rotary evaporated, and purified by...

Embodiment 3

[0161] Example 3, Suzuki coupling reaction to prepare alternate copolymers containing hindered amines: poly{(9,9'-spirobifluorene-2,7-diyl)-alternate-copolymerization-{two (2,2,6, 6-tetramethylpiperidin-4-yl)6,6′-[2,5-benzenedi(oxyl)]dihexanoate-1,4-diyl}}

[0162] 2,7-(9,9'-spirobifluoren-2-yl)-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborane)

[0163] 2,2'-(9,9'-spirobi[9H-fluorene]-2,7-diyl)bis[4,4,5,5-tetramethyl-1,3,2-Dioxaborolane]

[0164]

[0165] First, take 2,7-dibromo-9,9-spirobifluorene (1.0 equiv.) and put it into a 250ml two-necked flask. The flask has been heated, dried and airtight, and then vacuumed three times with nitrogen. High-purity nitrogen is used It is used after strict anhydrous and anaerobic treatment before use. 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) was taken anhydrous and oxygen free. Then n-butyllithium (3.0equiv.) was slowly added t...

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Abstract

The present invention belongs to the field of photoelectronic material science and technology, and is especially one kind of materials containing hindered amine structure unit and its preparation process and application in organic electronics field. Each of these materials includes two parts of organic conjugated skeleton chain and hindered amine group, where, the organic conjugated skeleton molecular structure consists of conjugated oligomer with alkyl radical and polymer. These materials may be used as the stabilizer for organic material with high oxygen, heat, light and ultraviolet stability, especially the stabilizer for organic electronic material and photoelectronic material. These materials may be used also as carrier transmitting material, light emitting material, conducting material, etc. widely.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a kind of oligomer and polymer material containing hindered amine groups and its preparation method, and relates to the application of these luminescent materials in organic electroluminescence, organic field effect tube, organic solar cell, organic nonlinear optics, biosensing and organic laser 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.; 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 (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, other organic ele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/44C07D317/12C07D401/12C09K11/06H05B33/14
Inventor 黄维解令海司三民彭波
Owner FUDAN UNIV
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