Naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer, its preparation method and applications

A technology of naphthalene tetracarboxylic acid diimide and quinoxaline copolymer, which is applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, luminescent materials, etc., can solve the problem of reducing the photoelectric conversion efficiency of organic solar cells and cannot effectively Utilize the problems of sunlight and insufficient emission spectrum matching to achieve the effects of increasing mobility, improving solution processability, and good solubility

Inactive Publication Date: 2012-02-01
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, because naphthalimide and its derivatives contain large planar conjugated systems and good molecular coplanarity, the interaction of large π bonds between molecules is very strong, and they have large lattice energy, so their solubility is relatively low. Poor, poor film-forming processability, resulting in the preparation of the device is prone to phase separation, affecting the efficiency of exciton diffusion, resulting in energy loss
In addition, since the absorption spectrum of naphthalimide and its derivatives is mainly concentrated in the visible region, the absorption range is not wide enough, and the matching degree with the emission spectrum of sunlight is not high enough, so sunlight cannot be effectively used, and organic solar energy will also be reduced. Photoelectric conversion efficiency of the battery

Method used

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  • Naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer, its preparation method and applications
  • Naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer, its preparation method and applications
  • Naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer, its preparation method and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]Poly N,N'-bis-(2-octyldecyl)-1,4,5,8-naphthalene diimide-(2-methyl-3-methoxy)dithieno[3,2 -f: Synthesis of 2',3'-h]quinoxaline (n=30):

[0035]

[0036] Under the protection of nitrogen, to the compound N,N'-bis-(2-octyldecyl)-2,6-dibromo-1,4,5,8-naphthalene diimide 0.5mmol, 6,9 - A solution of 0.5 mmol of bistributyltin-(2-methyl-3-methoxy)dithieno[3,2-f:2',3'-h]quinoxaline in DMF (18 mL). Bubble 0.5h to remove residual oxygen. Then join Pd 2 (dba) 3 (0.0.14g, 0.015mol) and P(o-Tol) 3 (0.0083g, 0.027mmol) and bubbling for 0.5h to remove residual oxygen, then heated to 80°C for 48 hours. The mixture was added dropwise to methanol for settling. Suction filtration, washing with methanol, and drying. It was then dissolved in toluene, added to an aqueous solution of sodium diethyldithiocarbamate, and the mixture was heated to 90°C and stirred overnight. The organic phase was subjected to column chromatography on alumina, eluting with chlorobenzene. The organic so...

Embodiment 2

[0038] Poly N,N'-bis-(2-hexyloctyl)-1,4,5,8-naphthalene diimide-(2-hexyl-3-decyl)dithieno[3,2-f: Synthesis of 2',3'-h]quinoxaline (n=16):

[0039]

[0040] Under the protection of nitrogen, to the compound N, N'-bis-(2-hexyloctyl)-2,6-dibromo-1,4,5,8-naphthalene diimide 0.5mmol, 6,9- A solution of 0.5 mmol of bistributyltin-(2-hexyl-3-decyl)dithieno[3,2-f:2',3'-h]quinoxaline in dioxane (15 mL). Bubble 0.5h to remove residual oxygen. Then add Pd(PPh 3 ) 2 Cl 2 10mg, bubbled for 0.5h to remove residual oxygen, and then heated to 120°C for 24 hours. The mixture was added dropwise to methanol for settling. Suction filtration, washing with methanol, and drying. It was then dissolved in toluene, added to an aqueous solution of sodium diethyldithiocarbamate, and the mixture was heated to 90°C and stirred overnight. The organic phase was subjected to column chromatography on alumina, eluting with chlorobenzene. The organic solvent was removed under reduced pressure and met...

Embodiment 3

[0042] Poly N,N'-bis-(2-methyltetradecyl)-1,4,5,8-naphthalene diimide-(2,3-di-eicosyl)dithieno[3 , 2-f: Synthesis of 2',3'-h]quinoxaline (n=25):

[0043]

[0044] Under the protection of nitrogen, to the compound N,N'-bis-(2-methyltetradecyl)-2,6-dibromo-1,4,5,8-naphthalene diimide 0.5mmol, 6 , 9-bistributyltin-(2,3-di-eicosyl)dithieno[3,2-f:2',3'-h]quinoxaline 0.5mmol solution in toluene / THF (30mL) . Bubble 0.5h to remove residual oxygen. Then add Pd(PPh 3 ) 4 8mg, bubbled for 0.5h to remove residual oxygen, and then heated to 50°C for 72 hours. The mixture was added dropwise to methanol for settling. Suction filtration, washing with methanol, and drying. Then it was dissolved in toluene, added to the aqueous solution of sodium diethyldithiocarbamate, and then the mixture was heated to 80C and stirred overnight. The organic phase was subjected to column chromatography on alumina, eluting with chlorobenzene. The organic solvent was removed under reduced pressure an...

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Abstract

The invention, belonging to the field of photoelectron material, discloses a naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer of formula (I), wherein, n represents an integer between 1 and 100, R1 and R2 represent hydrogen, C1 to C20 alkyl, C1 to C20 alkyloxy benzene, and R3 and R4 represent C1 to C20 alkyl or alkyloxy. The invention also provides a preparation method and applications of the naphthalene tetracarboxylic acid diimide-dithiophene quinoxaline copolymer. According to the invention, by forming an electron donor-acceptor structure, the band gap of the polymer is adjusted, and the absorption band edge is pushed to the infrared and near infrared region; and the modified naphthalene tetracarboxylic acid diimide has good dissolvability, strong absorbance, and wide absorption region that extends to the near infrared region, improves the utilization rate of sunlight, and has excellent charge transport performance.

Description

technical field [0001] The invention relates to a conjugated polymer, more specifically to a naphthalene tetracarboxylic acid diimide-dithienoquinoxaline copolymer. [0002] The invention also relates to the preparation method and application of the diimide-dithienoquinoxaline copolymer containing naphthalene tetracarboxylic acid. Background technique [0003] 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 p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰王烨文吕婷马文波
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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