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Bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer and preparation method thereof

A technology of bisthiophenepyrrolopyrrole and thiophenepyrrolopyrrole is applied in the field of design and synthesis of polymer optoelectronic functional materials, which can solve the problem that four thiophene units have not been reported, and achieve the effects of improving charge transport performance and improving solar light absorption efficiency.

Inactive Publication Date: 2016-06-01
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polymers based on tetrathiophene units, benzothiadiaz

Method used

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  • Bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer and preparation method thereof
  • Bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer and preparation method thereof
  • Bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 polymer P1

[0029]

[0030] Under nitrogen atmosphere, add monomer compound 1 (313.01mg, 0.5mmol) into a 10mL microwave reaction flask (R1=H, R2=H, R4=CH 3 ), monomer compound 2 (509.61mg, 0.5mmol) (X=Br, R3=CH2CH(C8H17)(C10H21)), Pd(PPh 3 ) 4 (5.78mg, 0.005mmol) and o-xylene 4ml, heat up reaction in microwave reactor: 90°C, 10min; 100°C, 10min; 170°C, 40min; a dark blue sticky substance was obtained. The reaction solution was methanol-precipitated, and the solid obtained was extracted with methanol, acetone, n-hexane, chloroform, and chlorobenzene Soxhlet respectively, and the chloroform and chlorobenzene extracts were collected, respectively precipitated by methanol again, and vacuum-dried to obtain 0.41 g of a blue solid product (chloroform extract ), 70mg (chlorobenzene extract). Overall yield: 83%. MolecularWeight (GPC, eluent = chlorobenzene, detector = RI): M n , 2500 (chloroformfraction) FT-IR (NaCl): 3071, 2928, 2847, 1663...

Embodiment 2

[0031] The synthesis of embodiment 2 polymer P2

[0032] Under nitrogen atmosphere, add monomer compound 1 (313.01mg, 0.5mmol) into a 10mL microwave reaction flask (R1=H, R2=F, R4=CH 3 ), monomer compound 2 (509.61mg, 0.5mmol) (X=Br, R3=CH2CH(C8H17)(C10H21)), Pd(PPh 3 ) 4 (5.78mg, 0.005mmol) and o-xylene 4ml, reacted in a microwave reactor, 80°C, 10min; 120°C, 10min; 200°C, 30min; Chloroform and chlorobenzene Soxhlet extraction, chloroform and chlorobenzene extracts were collected, precipitated with methanol again, and vacuum dried to obtain a blue solid 0.21 g (chloroform extract), 30 mg (chlorobenzene extract). Overall yield: 40%. MolecularWeight (GPC, eluent = chlorobenzene, detector = RI): M n,3050(chloroformfraction)FT-IR(NaCl):3066,2928,2847,1663,1547,1427,1254,1226,1024,852,788,731.

Embodiment 3

[0033] The synthesis of embodiment 3 polymer P3

[0034] Under nitrogen atmosphere, add monomer compound 1 (313.01mg, 0.5mmol) into a 10mL microwave reaction flask (R1=C 6 h 13 , R2=F, R4=CH 3 ), monomer compound 2 (509.61mg, 0.5mmol) (X=Br, R3=CH2CH(C8H17)(C10H21)), Pd(PPh 3 ) 4 (5.78mg, 0.005mmol) and 4ml o-xylene were reacted in a microwave reactor, 100°C, 5min; 110°C, 5min; 130°C, 60min; a blue sticky substance was obtained. The reaction solution was precipitated by methanol, and the obtained solid was extracted with methanol, acetone, n-hexane, chloroform, and chlorobenzene Soxhlet respectively, and the chloroform and chlorobenzene extracts were collected, precipitated by methanol again, and vacuum-dried to obtain 0.29 g of a blue solid product (chloroform extract) , 80mg (chlorobenzene extract). Overall yield: 54%. MolecularWeight (GPC, eluent = chlorobenzene, detector = RI): M n ,5961(chloroformfraction)FT-IR(NaCl):3070,2922,2852,1660,1550,1425,1323,1230,1074,855...

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Abstract

The invention relates to a bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer and a preparation method thereof and belongs to the field of design and synthesis of polymer photoelectric functional materials. The bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer has the structural unit as shown in the description, wherein R1 is the alkyl group of hydrogen atom and C6-C20; R2 is the alkyl group or the alkoxy group of hydrogen atom, fluorine atom and C6-C20; R3 is the alkyl group of C6-C20; n is 2 to 60. The bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer takes commercial bithiophene benzothiadiazole bitin monomers and bithiophene pyrrolopyrrole dibromo monomers as the reaction raw materials, and is quickly and efficiently prepared by a microwave-assisted Stille condensation polymerization method. The invention provides the novel conjugated polymer material based on thiophene, pyrrolopyrrole and benzothiadiazole, and the novel conjugated polymer material combines the advantages of thiophene, pyrrolopyrrole and benzothiadiazole. The bithiophene benzothiadiazole-bithiophene pyrrolopyrrole conjugated polymer is expected to be applied to active materials in organic thin-film transistors and organic photovoltaic devices.

Description

technical field [0001] The invention belongs to the technical field of design and synthesis of polymer optoelectronic functional materials, and in particular relates to a bisthiophene benzothiadiazole-bis thiophene pyrrolopyrrole conjugated polymer and a preparation method thereof. Background technique [0002] Since the discovery of conductive polymers in the 1970s, the design, synthesis and application research of new conductive polymers has attracted extensive attention from the industrial and scientific circles all over the world. Although compared with traditional inorganic materials, this type of material has unparalleled advantages such as light weight, low cost, good flexibility, and can be processed by cheap solution processing, and can be prepared into flexible and foldable devices. Optoelectronic devices such as organic light-emitting diodes, organic field effect transistors, organic solar cells, etc., which are active materials, have shown attractive application ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46
CPCC08G61/124C08G61/126C08G2261/3223C08G2261/18C08G2261/51C08G2261/414C08G2261/3246C08G2261/12H10K85/113Y02E10/549
Inventor 杜俊平陈凤华方少明田俊峰李皓李臻张亚芳李闯
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY