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Application of annular alkyl chain substituted semiconductor polymer in organic solar cell

A technology of alkyl chains and semiconductors, applied in the field of donor-acceptor narrow-bandgap semiconducting polymers, which can solve the problems of great influence on stacking characteristics, disordered arrangement, low symmetry, etc.

Inactive Publication Date: 2017-01-04
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
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Problems solved by technology

[0003] The influence of the conjugated main chain on the band gap and energy level of the polymer is very important. Therefore, it is effective and widely used to screen different conjugated units, construct new polymer systems, and adjust the intra-chain / inter-chain charge transfer characteristics. However, at the same time, many studies have also proved that different alkyl side chains have a great influence on the stacking characteristics and carrier mobility of polymers, and it has gradually developed into a mainstream regulation of polymer materials. method of performance
At present, the research on flexible alkyl side chains mostly focuses on n-alkyl chains and iso-alkyl chains. We found that when these alkyl chains are substituted on organic semiconductors, the crystal structure shows that many chains are not linear." "Zigzag" arrangement, its arrangement tends to be messy and has low symmetry, and it will also induce a decrease in the symmetry of the crystal structure of the substituted conjugated unit. orderly accumulation and arrangement of

Method used

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  • Application of annular alkyl chain substituted semiconductor polymer in organic solar cell
  • Application of annular alkyl chain substituted semiconductor polymer in organic solar cell
  • Application of annular alkyl chain substituted semiconductor polymer in organic solar cell

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Example 1: Based on cyclopentyl substitution of 4,7-dithiophene benzo[ c ][1,2,5]Thiadiazole (DTBT) and BDT Alternating Copolymer Preparation, the detailed route is attached Figure 4 .

[0033] (1) 3-cyclopentylthiophene (TH- c 5) Synthesis of:

[0034]Add 1.2 g (50 mmol) magnesium and 1 grain of iodine into a 100 mL three-necked flask, add 30 mL anhydrous ether through a syringe under argon protection, slowly add 7.45 g (50 mmol) bromocyclopentane dropwise, and react to After the magnesium disappeared, the reaction bottle was placed in an ice bath, and 30 mg Ni(dppp)Cl was added 2 , and dropwise added 6.52 g (40 mmol) tribromothiophene. After reflux overnight, the brown solution was poured into ice water and neutralized with dilute hydrochloric acid. The aqueous phase was extracted three times with ether, and the organic phases were combined and dried over anhydrous sodium sulfate. Diethyl ether was distilled off under reduced pressure, and 3.96 g of colorless li...

Embodiment 2

[0041] Embodiment 2: Based on the preparation of cycloheptyl-substituted DTBT and BDT alternating copolymers, the detailed route is shown in the appendix Figure 5 .

[0042] (1) 3-cycloheptylthiophene (TH- c 7) Synthesis of:

[0043] Reference TH- c The synthesis method of 5, add 1.2 g (50 mmol) magnesium and 1 grain of iodine into a 100 mL three-necked bottle, add 30 mL anhydrous ether through a syringe under the protection of argon, slowly add 8.85 g (50 mmol) bromocyclic Heptane, react until the magnesium disappears, place the reaction bottle in an ice bath, add 30 mg Pd(dppf)Cl 2 , and dropwise added 6.52 g (40 mmol) tribromothiophene. After reflux overnight, the brown solution was poured into ice water and neutralized with dilute hydrochloric acid. The aqueous phase was extracted three times with ether, and the organic phases were combined and dried over anhydrous sodium sulfate. Diethyl ether was distilled off under reduced pressure, and 4.76 g of colorless liquid ...

Embodiment 3

[0050] Embodiment 3: Based on the preparation of n-pentyl substituted DTBT and BDT alternating copolymers, the detailed route is attached Figure 6 .

[0051] (1) 3-n-pentylthiophene (TH- n 5) Synthesis of:

[0052] Reference TH- c The synthesis method of 5, add 1.2 g (50 mmol) magnesium and 1 iodine to a 100 mL three-necked bottle, add 30 mL anhydrous ether through a syringe under the protection of argon, and slowly add 7.55 g (50 mmol) bromo-n- Pentane, react until the magnesium disappears, place the reaction bottle in an ice bath, add 30 mg Ni(dppp)Cl 2 , and dropwise added 6.52 g (40 mmol) tribromothiophene. After reflux overnight, the brown solution was poured into ice water and neutralized with dilute hydrochloric acid. The aqueous phase was extracted three times with ether, and the organic phases were combined and dried over anhydrous sodium sulfate. Diethyl ether was distilled off under reduced pressure, and 4.63 g of colorless liquid was obtained by distillation ...

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Abstract

The invention relates to a donor-receptor type narrow-band semiconductor polymer containing annular alkyl chains. The polymer comprises different donor and receptor structural units. The polymer aims at utilizing the advantages of high rigidity, good symmetry and preferential conformation of cycloparaffin relative to branched paraffin for regulating and controlling the self-assembly character of the film forming process of the polymer and improving the ordering performance of the polymer in a mixed film. The annular alkyl chains can properly twist polymer main chains, even so, the band gap of the polymer is almost not influenced, wide absorption is still achieved, and the polymer is crucially important to improving the open-circuit voltage of the polymer solar cell and reducing energy loss. Based on researches, it is found that the annular alkyl chains can comprehensively improve the open-circuit voltage, short-circuit current density and fill factor of the polymer solar cell, finally, the power conversion efficiency of the polymer solar cell is remarkably improved, and the polymer is a semiconductor polymer modified and substituted group with wide prospects.

Description

technical field [0001] The invention belongs to the technical field of organic / polymer solar cells, and in particular relates to the application of a class of donor-acceptor type narrow-bandgap semiconducting polymers containing cyclic alkyl chains in the field of organic solar cells. Background technique [0002] Polymer semiconductor materials and optoelectronic devices are favored by scientific research institutes and companies due to the advantages of easy-to-obtain materials, simple preparation process, spin-coating film formation, low cost, and large-area preparation, and have good commercialization prospects. The composition of the active layer in polymer-based solar cells is generally a mixture of one polymer and another fullerene derivative. Therefore, how to adjust the blending characteristics between the two and improve the active layer in the polymer phase Ordering is crucial to the performance of organic solar cells. Based on the optimization of the structure o...

Claims

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/149C08G2261/3246C08G2261/514C08G2261/91
Inventor 阳仁强韩亮亮文树光陈为超姜焕祥
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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