Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

A technology of unit naphthalene tetracarboxylic acid diimide copolymer and thiadiazole, applied in the field of cyclopentadiene dithiophene-benzobis(benzothiadiazole) copolymer and its preparation and application, It can solve the problems of low conversion efficiency and achieve the effects of simple structure, good electron delocalization performance and excellent charge transport performance

Active Publication Date: 2014-07-23
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the research of polymer solar cells mainly focuses on the blending system of donor and acceptor, using polybenzodithiophene (PTB7) and fullerene derivative PC 71 The energy conversion efficiency of the BM blend system has reached 7.4%, but it is still much lower than the conversion efficiency of inorganic solar cells

Method used

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  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

Examples

Experimental program
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preparation example Construction

[0048] One embodiment contains the preparation method of thiadiazoloquinoxaline unit naphthalene tetracarboxylic acid diimide copolymer, such as figure 1 shown, including the following steps:

[0049] Step S100, providing compound A and compound B.

[0050] A is: B is: Among them, R 1 for C 1 ~C 20 The alkyl group or the following structural unit:

[0051] R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 The alkoxyl group, R 5 , R 6 , R 7 for H or C 1 ~C 20 of alkyl.

[0052] Wherein the preparation of compound A comprises the following steps:

[0053] Step S111, providing compound C and compound D represented by the following structural formula,

[0054] C is: D is: R 1 -NH 2 , where R 1 for C 1 ~C 20 The alkyl group or the following structural unit: R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 of alkoxy.

[0055] It should be noted that C 1 ~C 20 The alkyl group is C 1 ~C 20 branched chain alkyl or C 1 ~C 20 branched c...

Embodiment 1

[0088] This embodiment discloses poly N,N'-di-methyl-1,4,5,8-naphthalene tetracarboxylic acid diimide-6,7-dihexyl-4,9-di(4 -Ethylthiophen-2-yl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (copolymer of naphthalene tetracarboxylic diimide containing thiadiazoloquinoxaline unit P1):

[0089]

[0090] The preparation process of the above-mentioned naphthalene tetracarboxylic acid diimide copolymer P1 containing thiadiazoloquinoxaline units is as follows:

[0091] 1.1. Preparation of N,N'-dimethyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (compound A)

[0092]

[0093] Compound C and compound D are provided, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, and compound D is n-octylamine (C 8 h 17 NH 2 );

[0094] Under nitrogen protection, methylamine (compound D) (1mmol) was added to a solution of propionic acid (15mL) containing 2,6-dibromo-1,4,5,8-naphthalene dianhydride (0.1mmol), and reflux 12 hours. After cooling to room temperature, the rea...

Embodiment 2

[0106] This example discloses poly N,N'-bis-(1-octylnonyl)-1,4,5,8-naphthalene tetracarboxylic acid imide-6,7-bis(1-octylnonyl) with the following structural formula Alkyl)-4,9-di(thiophen-2-yl)[1,2,5]thiadiazolo[3,4-g]quinoxaline (containing thiadiazoloquinoxaline unit naphthalene tetracarboxylic Acid diimide copolymer P2):

[0107]

[0108] The preparation process of the above-mentioned naphthalene tetracarboxylic acid diimide copolymer P2 containing thiadiazoloquinoxaline units is as follows:

[0109] 2.1. Preparation of N,N'-bis-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (compound A)

[0110]

[0111] Provide compound C and compound D, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, compound D is 1-octyl-nonylamine;

[0112] Under nitrogen protection, 1-octyl-nonylamine (compound D) (0.255g) was added to 2,6-dibromo-1,4,5,8-naphthalene dianhydride (compound C) (0.1mmol ) in propionic acid (15 mL) and reflux for 14 hours....

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Abstract

The invention provides a naphthalene tetracarboxylic diimide copolymer containing thiadiazoloquinoxaline units, a preparation method and applications thereof. The naphthalene tetracarboxylic diimide copolymer containing thiadiazoloquinoxaline units has a structural formula represented in the description, wherein n is an integer in a range of 10 to 100, R1 represents a C1-C20 alkyl group or a structural unit represented in the description, R2, R3, and R4 represent H, a C1-C20 alkyl group, or a C1-C20 alkoxyl group, and R5, R6, and R7 represent H or a C1-C20 alkyl group; and is capable of improving the energy conversion efficiency of semiconductor devices.

Description

technical field [0001] The present invention relates to a kind of naphthalene tetracarboxylic diimide copolymer containing thiadiazoloquinoxaline unit, its preparation method and solar energy containing thiadiazoloquinoxaline unit naphthalene tetracarboxylic diimide copolymer Applications in battery devices, organic electroluminescent devices and organic field effect transistors. Background technique [0002] The preparation of low-cost and high-efficiency semiconductor devices using cheap optoelectronic materials has always been a research hotspot and difficulty in the field of semiconductor devices. [0003] 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 optoelectronic materials for a long time. Polymer solar cells have attracted much attention due to the advantage...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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