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Conjugated polymer photoelectric material containing quinoxaline imide condensed ring and application thereof

A quinoxaline imide condensed ring and conjugated polymer technology, which is applied in the field of conjugated polymer photoelectric materials, can solve the problems of limited application range and low polymer energy level, and achieve strong electron-deficiency and effective absorption and the effect of using

Active Publication Date: 2018-12-11
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

When the quinoxaline and imide units are separately used as copolymerization units to construct conjugated polymers, the lowest unoccupied molecular orbital (LUMO) energy level and the highest occupied molecular orbital (HOMO) energy level of the polymer are not low enough, which limits Its application range, such as not being used as an N-type semiconductor material or a polymer acceptor in optoelectronic devices such as field effect crystals and organic solar cells

Method used

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  • Conjugated polymer photoelectric material containing quinoxaline imide condensed ring and application thereof
  • Conjugated polymer photoelectric material containing quinoxaline imide condensed ring and application thereof
  • Conjugated polymer photoelectric material containing quinoxaline imide condensed ring and application thereof

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Experimental program
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Effect test

Embodiment 1

[0045] Preparation of Polymer Optoelectronic Material Poly[5,8-2-Alkylquinoxalinoimide-2,5-thiophene] (abbreviated as P1)

[0046] The synthetic route is as follows:

[0047]

[0048] (1) Synthesis of 3,6-dibromo-1,2-o-phenylenediamine:

[0049] Dissolve 5.88g of 4,7-dibromo-2,1,3-benzothiadiazole 4 in 200mL of ethanol, cool with ice water, and add 14.0g of sodium borohydride in batches. After reacting for 6h, pour into ice brine and filter with suction. After drying, 2.44 g of yellow flaky solid 3,6-dibromo-1,2-o-phenylenediamine 5 was obtained, with a yield of 46%.

[0050] (2) Synthesis of 5,8-dibromo-2-alkylquinoxaline imide (the alkyl group is 2-butyloctyl):

[0051] Dissolve 2.65g of 3,6-dibromo-1,2-o-phenylenediamine in 50mL of acetic acid, add 0.72g of sodium acetate and 3.8g of alkylpyrrole-2,3,4,5-tetraketone (3), Heated to reflux for 24h. The reaction solution was poured into ice-salt water, dichloromethane was added under stirring for extraction, the organi...

Embodiment 2

[0057] Preparation of Polymer Optoelectronic Material Poly[5,8-2-Alkylquinoxalinoimide-2,5-3,4-Difluorothiophene] (abbreviated as P2)

[0058] Synthesis of poly[5,8-2-alkylquinoxaline imide-2,5-3,4-difluorothiophene] (referred to as P2):

[0059] Under an argon atmosphere, 616mg of 5,8-dibromo-2-alkylquinoxalimide, 447mg of 2,5-bis(trimethyltinyl)-3,4-difluorothiophene, 4.5mg Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) and 9.0 mg of tris(o-methylphenyl)phosphorus (P(o-Tol)3) were dissolved in a mixed solvent of 10 mL of toluene and 5 mL of tetrahydrofuran. Under the protection of argon, the reaction was refluxed for 20 h. After cooling to room temperature, the reaction liquid was dropped into 300 mL of methanol for precipitation, and a blood-red solid was obtained by filtration. After extracting with acetone, methanol, n-hexane, and dichloromethane in a Soxhlet extractor for 24 hours, the polymer was finally washed with chloroform, cooled and filtered through a 0.45 μm ...

Embodiment 3

[0062] Example 1 and Example 2 synthesized polymers P1, P2 illustrate that such polymers can be used as N-type or polymer acceptors in polymer solar cell devices (ITO cathode / cathode interface layer / active layer / Yang machine interface layer / anode):

[0063] Pre-cut the ITO conductive glass with a square resistance of 20 ohms / cm2 into 15mm×15mm square pieces. Use acetone, special detergent for micron-sized semiconductors, deionized water, and isopropanol to clean ultrasonically in sequence, blow nitrogen whistle, and place in a constant temperature oven for later use. Spin-coat a layer of PFN-Br with a thickness of 5nm on the ITO, then spin-coat the active layer materials PTB7-Th / P1, PTB7-Th / P2 with a thickness of about 100nm, and finally evaporate MoO 3 and Al electrodes. All preparations were carried out in a glove box under a nitrogen atmosphere. The current-voltage curves of the fabricated flip-chip devices are as follows: Figure 6 The relevant data are listed in Ta...

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Abstract

The invention discloses a conjugated polymer photoelectric material containing a quinoxaline imide condensed ring and an application thereof. The material has conjugated main chain and side chain groups, wherein the conjugated main chain contains a quinoxaline imide condensed ring structure and other copolymerized units and the side chain groups comprise alkyl chains R which enhance polymer solubility. As the polymer has the conjugated main chain structure, electron clouds can be delocalized on the polymer main chain, so that the polymer shows a semiconductor characteristic and has a rich photoelectric property; meanwhile, the polymer can be dissolved in an organic solvent as a result of the hydrotropic group R on the polymer side chain, so that the polymer is suitable for preparing a photoelectric apparatus by way of printing, reel-to-reel or ink-jet printing solution processing method. The conjugated polymer containing the quinoxaline imide condensed ring can be used as a carrier transmission layer, an N-type material, a light emitting layer or a photovoltaic active layer to be applied to photovoltaic, light-emitting or field effect transistor photoelectric apparatuses.

Description

technical field [0001] The invention relates to the field of a class of conjugated polymers and macromolecular optoelectronic materials, in particular to conjugated polymer optoelectronic materials containing quinoxaline imide condensed rings and applications thereof. Background technique [0002] The development of organic / polymer optoelectronic materials provides a new way for the preparation of low-cost, large-area optoelectronic devices. In the late 1970s, Alan J. Heeger et al. (2000 Nobel Laureate in Chemistry) invented conductive polymers, which completely overturned the traditional concept of organic materials based on carbon atoms as insulators, and opened up the organic / polymer In the emerging scientific field of semiconductor electronics, the optical, electrical, and magnetic properties of organic materials have gradually been recognized by humans, and various optoelectronic devices based on them have also attracted people's attention. Organic / polymer semiconducto...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/12C08G61/122C08G61/126C08G2261/411C08G2261/414C08G2261/91C08G2261/124C08G2261/18C08G2261/3223C08G2261/3241H10K85/111Y02E10/549
Inventor 刘升建陈家乐曹智雄蔡跃鹏
Owner SOUTH CHINA NORMAL UNIVERSITY
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