Thieno (3,4-b) pyrazine contained fluorene copolymer, preparation method and application thereof

A 4-b, copolymer technology, applied in the direction of electrical components, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problems of rare and limited material development, and achieve improved stability, wide spectral response range, and reaction conditions mild effect

Inactive Publication Date: 2011-10-05
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the current research on such materials is mostly the copolymerization of two monomers, but the copolymerization of three or more monomers is rare, which greatly limits the development of such materials.

Method used

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  • Thieno (3,4-b) pyrazine contained fluorene copolymer, preparation method and application thereof
  • Thieno (3,4-b) pyrazine contained fluorene copolymer, preparation method and application thereof
  • Thieno (3,4-b) pyrazine contained fluorene copolymer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] A fluorene copolymer of the following molecular structural formula:

[0058]

[0059] The preparation steps of above-mentioned fluorene copolymer are as follows:

[0060] (1) Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dihexylfluorene:

[0061]

[0062] Add 13.00mL (2.00M) of n-butyllithium solution to a reaction flask containing 4.92g of 2,7-dibromo-9,9-dihexylfluorene and 100.00mL of tetrahydrofuran at -78°C under nitrogen. After stirring for 2.5 hours, slowly add 5.50 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane dropwise, return to room temperature, and continue stirring for 26 hours . After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, washed with petroleum ether, and precipitated with methanol to obtain white needle crystals. MALDI-TOF-MS (m / z): 586.5 (M + ).

[0063] (2) Preparation of 2,5-dibromothieno[3,2-b]t...

Embodiment 2

[0073] This embodiment discloses a fluorene copolymer with the following structure:

[0074]

[0075] The preparation steps of above-mentioned fluorene copolymer are as follows:

[0076] (1) Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dioctylfluorene:

[0077]

[0078] At -78°C under nitrogen, add 22.00mL (2.00M) of n-butyllithium solution to two ports containing 11.00g of 2,7-dibromo-9,9-dioctylfluorene and 80.00mL of tetrahydrofuran with a syringe In the flask, after stirring for 2 hours, slowly add 10.00mL 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane dropwise, return to room temperature, continue Stir for 29 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, washed with petroleum ether, and precipitated with methanol to obtain white needle crystals. MALDI-TOF-MS (m / z): 642.6 (M + ).

[0079] (2) Preparation of 2,5-dibr...

Embodiment 3

[0089] This embodiment discloses a fluorene copolymer with the following structure:

[0090]

[0091] The preparation steps of above-mentioned fluorene copolymer are as follows:

[0092] (1) Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dihexylfluorene:

[0093]

[0094] Add 13.00mL (2.00M) of n-butyllithium solution to a reaction flask containing 4.92g of 2,7-dibromo-9,9-dihexylfluorene and 100.00mL of tetrahydrofuran at -58°C under nitrogen. After stirring for 2.5 hours, slowly add 5.50 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane dropwise, return to room temperature, and continue stirring for 21.5 hours . After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, washed with petroleum ether, and precipitated with methanol to obtain white needle crystals. MALDI-TOF-MS (m / z): 586.5 (M + ).

[0095] (2) Preparation of 2,5-dibromothi...

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Abstract

The invention discloses a thieno (3,4-b) pyrazine contained fluorene copolymer with a general molecular formula as shown in (I), as well as its preparation method and application. In the formula, R1, R2, R3 and R4 stand for alkyls selected from H or / and C1-C25, x and y both not equal to 0 meet the relation x+y=1, and n is any positive integer from 1-500, and Ar1 stands for a thiophene containing group. According to the method, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) fluorene monomers, bromothiophene monomers and 2,5-dibromothieno (3,4-b) pyrazine monomers are subjected to a polymerization reaction according to a stoichiometric ratio in an alkaline environment and a weak polar or / and a polar aprotic organic solvent, thus obtaining the copolymer. The copolymer of the invention has good stability and dissolvability, strong absorbance of light, wide light-absorbing range, thus improving the utilization rate of sunlight. With simple preparation, high yield, easy operation and control, the method of the invention is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a fluorene copolymer containing thieno[3,4-b]pyrazine units, a preparation method and application thereof. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion efficiency can be improved to be close to that of commercial sili...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/30H01L51/46H01L51/54C08G61/12
CPCY02E10/50Y02E10/549
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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