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Quinoxaline unit-containing fluorene copolymer, and preparation method and application thereof

A kind of copolymer and unit fluorene technology, which is applied in the field of fluorene-based copolymer containing quinoxaline unit and its preparation, can solve the mismatch between the spectral response of the device and the solar radiation spectrum, the low collection efficiency of the carrier electrode, and the lack of the red light region. Effective utilization and other issues, to achieve the effect of simple preparation route, high yield, easy operation and control

Inactive Publication Date: 2014-05-28
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the energy conversion efficiency of polymer solar cells has reached 6.5%, but it is still much lower than that of inorganic solar cells. The main constraints that limit the improvement of performance are: the relatively low carrier mobility of organic semiconductor devices, The spectral response of the device does not match the solar radiation spectrum, the red light region with high photon flux is not effectively utilized, and the electrode collection efficiency of carriers is low, etc.

Method used

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  • Quinoxaline unit-containing fluorene copolymer, and preparation method and application thereof
  • Quinoxaline unit-containing fluorene copolymer, and preparation method and application thereof
  • Quinoxaline unit-containing fluorene copolymer, and preparation method and application thereof

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preparation example Construction

[0035] And, the embodiment of the present invention also provides the preparation method of the fluorene copolymer containing quinoxaline unit, comprising the following steps:

[0036] 1) Provide compounds A, B, and C represented by the following structural formula respectively,

[0037]

[0038] Among them, R 1 , R 2 Choose from H or C 1 ~C 20 the alkyl group; R 3 , R 4 from C 1 ~C 20 Alkyl, alkoxy, phenyl or phenoxy; Ar 1 It is a group containing a thiophene unit;

[0039]2) Under the conditions of anaerobic, alkaline environment and the presence of catalyst and organic solvent, compound A, B and C are subjected to Suzuki coupling reaction to obtain the quinoxaline unit-containing fluorene represented by general formula (I) class copolymer,

[0040]

[0041] In the formula, x+y=1, and x≠0, y≠0; n=any integer from 1 to 200,

[0042] The chemical reaction formula of this Suzuki coupling reaction is as follows:

[0043]

[0044] In the above-mentioned step ...

Embodiment 1

[0062] The copolymer of present embodiment 1 is the fluorene-based copolymer I containing quinoxaline unit represented by the following molecular structural formula 1 , its structural formula is as follows:

[0063]

[0064] Its preparation steps are as follows:

[0065] (1) Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dimethylfluorene, whose structural formula is as follows :

[0066]

[0067] The specific process of preparation is: at -100°C, under the condition of anhydrous and nitrogen protection, add 20.00mL of n-butyllithium oil solution with a concentration of 1.00M to 3.52g of 2,7-dibromo-9,9 - In a reaction flask of dimethylfluorene and 100mL tetrahydrofuran, after stirring for 2 hours, slowly add 4.17mL 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-di Oxaborane, returned to room temperature, continued to stir for 24 hours, after the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous ...

Embodiment 2

[0078] The copolymer of present embodiment 2 is the fluorene-based copolymer I containing quinoxaline unit represented by the following molecular structural formula 2 The preparation, its structural formula is as follows:

[0079]

[0080] Its preparation steps are as follows:

[0081] (1) Preparation of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dimethylfluorene, whose structural formula is as follows , see Example 1 for the preparation steps.

[0082]

[0083] (2) The preparation of 3,6-dimethylthieno[3,2-b]thiophene, its structural formula is as follows:

[0084]

[0085] The specific process of preparation is: 12.00g 3,6-dibromo-thieno[3,2-b]thiophene and 132mg (1,1'-bis(diphenylphosphino)ferrocene)palladium chloride ( Ⅱ) Add it to a 100mL tubular glass bottle equipped with a stirring rod, seal it, blow it with nitrogen, add 30mL tetrahydrofuran and 50mL methyl zinc bromide (dissolve methyl zinc bromide in tetrahydrofuran solution, its concentration is...

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Abstract

The invention discloses a quinoxaline unit-containing fluorene copolymer with a molecular structural general formula shown as (I), and a preparation method and application thereof. In the formula, x plus y is equal to 1, x is not equal to 0 and y is not equal to 0; n is any integer of 1 to 200; R1 and R2 are H or C1 to C20 alkyl; R3 and R4 are C1 to C20 alkyl, alkoxy, phenyl or phenoxyl; and Ar1 is a thiophene unit-containing group. The quinoxaline unit-containing fluorene copolymer has high stability and solubility, high absorbance and wide light-absorbing range and improves photoelectric conversion efficiency. The preparation method is simple, high in yield, easy in operation and control and suitable for industrialized 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 quinoxaline units and its preparation method and application. 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 silicon solar cel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/00H01S5/36
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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