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Conjugated polymer or oligomer having narrow band gap characteristic and side chain stereoregularity, and its preparation method

A technology of oligomers and polymers, which is applied in the field of organic conjugated polymers and oligomer materials and their preparation, can solve the problems of great differences, poor performance, and no consideration of side chain stereoregularity, etc., to achieve The effect of broad application prospects

Inactive Publication Date: 2013-01-02
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Five years ago, the more excellent systems were stereoregular poly-3-hexylthiophene (rr-P3HT) and PC 61 BM(C 60 Derivatives of the bulk heterojunction) composed of bulk heterojunction, after careful condensed state control, the photoelectric conversion efficiency of this system reaches ~5%, but compared with inorganic solar cells, it is still far behind
However, most of the narrow-bandgap conjugated polymers developed so far do not consider the stereoregularity of the side chains, resulting in poor performance

Method used

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  • Conjugated polymer or oligomer having narrow band gap characteristic and side chain stereoregularity, and its preparation method
  • Conjugated polymer or oligomer having narrow band gap characteristic and side chain stereoregularity, and its preparation method
  • Conjugated polymer or oligomer having narrow band gap characteristic and side chain stereoregularity, and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of monopolymer, namely 4-(4-alkyl-thiophen-2-yl)-[2,1,3]benzothiadiazole

[0033]

[0034] Step 1) In 40 mL of hydrobromic acid (HBr, 40%), add 4.29 g of [2,1,3]-benzothiadiazole. After heating to reflux, slowly add 1 equivalent (eq.) of liquid bromine (Br 2 , 2 mL), the reaction was continued for 3 hours under reflux conditions. After the temperature dropped to room temperature, sodium hydroxide (NaOH) aqueous solution was added to adjust the reaction mixture to neutrality, filtered, and the obtained solid was recrystallized by steam distillation and ethanol to obtain 1.94 g of 4-bromo-[2,1,3] - Benzothiadiazole, yield 29%. Step 2) Slowly drop 82.5 mL of n-butyllithium n-hexane solution (1.6 M) into a solution of diisopropylammonia (17.8 mL) in tetrahydrofuran (THF) under argon protection at -5°C, and stir for 0.5 h. Lithium diisopropylamide reagent (LDA) was prepared. Then, at -78°C, this reagent was slowly added dropwise into a THF solut...

Embodiment 2

[0036] Example 2: Preparation of the growth unit compound, namely 4-(4-alkyl-thiophen-2-yl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborin Pentane-2-yl)-[2,1,3]-benzothiadiazole

[0037]

[0038] Step 1) In 100 mL of hydrobromic acid (40%), add 14.9 g of [2,1,3]-benzothiadiazole. After heating to reflux, 3 equivalents of liquid bromine (16.8 mL) was slowly added dropwise, and the reaction was continued for 6 hours under reflux. After the temperature dropped to room temperature, NaOH aqueous solution was added, the reaction mixture was adjusted to neutrality, and the obtained yellow solid was recrystallized by THF to obtain 27.9 g of 4,7-dibromo-[2,1,3]-benzothiadiene azole with a yield of 82%.

[0039] Step 2) In 10 mL of THF, add 1 g (4-alkyl-thiophen-2-yl) sodium borate, 4.50 g 4,7-dibromo-[2,1,3]-benzothiadiazole, 2 mL Na 2 CO 3 aqueous solution (2M) and 0.14g Pd(PPh 3 ) 4 , After freezing and degassing, heat to 80°C for 12h. Then extracted with dichloromethane, separat...

Embodiment 3

[0041] Example 3: Preparation of dimers

[0042]

[0043] 0.62 g of N-bromosuccinimide (NBS) was gradually added to a THF solution of the monomer (1.06 g) under an ice-water bath. The reaction was carried out at room temperature for 12 hours, spin-dried and separated by column chromatography to obtain 118 g of brominated monomer with a yield of 88%.

[0044] In 10 mL of THF, add 1.02 g brominated monomer, 1.22 g 4-(4-alkyl-thiophen-2-yl)-7-(4,4,5,5-tetramethyl-1,3 , 2-dioxaborolan-2-yl)-[2,1,3]-benzothiadiazole, 4.1mLNa 2 CO 3 aqueous solution (2M) and 0.16g Pd(PPh 3 ) 4 , After freezing and degassing, heat to 80°C for 12h. Afterwards, it was extracted with dichloromethane and separated by column chromatography to obtain 1.24 g of dimer with a yield of 76%.

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Abstract

The present invention provides a conjugated polymer or oligomer having narrow band gap characteristic and side chain stereoregularity, and its preparation method. The conjugated oligomer or polymer has the following structure: R is a saturated alkyl long-chain substituent, m is an integer of 1 to 6, and n is an integer of 1 to 16 or an uncertain integer greater than 4. If n is an integer of 1 to 16, it is referred to the oligomer. If n is an uncertain integer greater than 4, with number average molecular weight of 1000 to 500000, it is referred to the polymer. The conjugated polymer and oligomer have the structural characteristic of the repeating unit containing the alternate benzthiadiazole electron acceptor group and the oligothiophene electron donor group, and have the typical electron donor-electron acceptor alternate structure, to bring the narrow band gap characteristic to the polymer and the oligomer; and alkyl substituents on the thiophene ring have unified direction to endow the polymer and the oligomer with side chain stereoregularity. The polymer and oligomer of special structure have excellent spectral properties, and are expected to have potentially wide range of applications in organic photovoltaic devices.

Description

Technical field: [0001] The invention belongs to the field of organic photoelectric materials, and relates to an organic conjugated polymer and oligomer material with both stereoregularity and narrow band gap characteristics and a preparation method thereof. Background technique: [0002] With the increasing energy, environment and climate problems, the development and utilization of solar energy resources are getting more and more attention. As a kind of solar power generation technology, organic solar cells are expected to greatly reduce the cost due to the use of organic photoelectric materials that are light in weight, flexible in nature, cheap in price, designable in synthesis, and capable of solution processing (such as printing, inkjet, printing, etc.) in the active layer. The cost of solar power generation, but also easy to realize large-area and flexible devices, has aroused great interest of scientists. [0003] The active layer materials of organic solar cells ge...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D417/14C08G61/12H01L51/46
CPCY02E10/549
Inventor 李维实叶怀英梅崇余
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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