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Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof

A metal polymer, polar side chain technology, used in photovoltaic power generation, circuits, electrical components, etc., can solve the problems of few reports, conjugated metal polymers have not attracted attention, etc., to achieve reduced thickness dependence, good electronic Transmission/extraction performance, multi-selective effects

Active Publication Date: 2013-10-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, conjugated metallopolymers containing functionalized polar side chain groups have not attracted much attention, and few reports have been reported.

Method used

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  • Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof
  • Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof
  • Conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Conjugated metal polymer optoelectronic materials with functionalized polar side chain groups poly[2,7-diethynyl-9,9'-bis(6-N,N-diethylamino-hexyl)fluorene- Mercury] (abbreviated as PFE6N-Hg) preparation

[0047] The synthetic route is as follows:

[0048]

[0049] (1) 2,7-diethynyl-9,9'-bis(6-bromo-hexyl)fluorene (monomer 4) was prepared according to the method disclosed in the literature [J.Phys.Chem.B2008,112,9295] .

[0050] (2) Synthesis of 2,7-diethynyl-9,9’-bis(6-N,N-diethylamino-hexyl)fluorene (monomer FE6N)

[0051] Add the raw material 2,7-diethynyl-9,9'-bis(6-bromo-hexyl)fluorene (4.74g, 9.0mmol) into the reaction flask, add 300mL N,N-dimethylformamide (DMF ) to dissolve the raw material, then add diethylamine (15mL), heat and reflux for 12h under argon protection, pour the reaction solution into ice water after cooling, extract and concentrate with dichloromethane, and pass the concentrate through the column to obtain Product 4.38g, yield 85%.

[005...

Embodiment 2

[0059] Conjugated metallopolymer optoelectronic material poly[2,7-diethynyl-9,9'-bis(3-N,N-diethylamino-propyl)fluorene with functionalized polar side chain groups - Mercury] (abbreviated as PFE3N-Hg) preparation

[0060] The synthetic route is as follows:

[0061]

[0062] (1) 2,7-dibromo-9,9'-bis(3-bromo-propyl)fluorene (monomer 5)

[0063] Add the raw material 2,7-dibromofluorene (13.0g, 40mmol) into the reaction flask, add 150mL of 1,3-dibromopropane, stir, add 20mL of 50% sodium hydroxide aqueous solution, 0.5g of tetrabutylammonium bromide, Under the protection of argon, the reaction was carried out at 50-60°C for 12 hours. After cooling, the reaction liquid was poured into ice water, extracted with dichloromethane, concentrated, and the concentrate was passed through a column to obtain 18.1 g of the product with a yield of 80%.

[0064] The NMR data of the product are as follows:

[0065] 1 H NMR (300MHz, CDCl 3 ,δ,ppm)7.55-7.49(m,6H),3.15-3.11(t,4H,J=6.54Hz),2....

Embodiment 5

[0093] The polymer PFE6N-Hg synthesized in Example 1 is taken as an example to illustrate that this polymer has the property of resisting solvent (chlorobenzene) elution, and can use orthogonal solvents to prepare multilayer organic / polymer solar cell devices.

[0094]Dissolve PFE6N-Hg in 1,4-dioxane, filter through a 0.45μm organic filter, and spin-coat on a common glass slide to form a film with a thickness of about 20nm. The absorbance of PFE6N-Hg after film formation was measured with a UV tester (HP8453spectrophotometer) produced by Hewlett-Packard Company, corresponding to figure 1 Curve 1 in . PFE6N-Hg is eluted with chlorobenzene afterwards PFE6N-Hg film, the absorbance of the PFE6N-Hg film after UV test elution, corresponds to figure 1 Curve 2 in . By observing that the absorbance of the PFE6N-Hg film does not decrease substantially after elution with chlorobenzene, it has excellent anti-solvent elution performance.

[0095] figure 1 The ultraviolet-visible light ...

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Abstract

The invention provides a conjugated metal polymer photoelectric material with functionalized polarity side-chain radicals and an application thereof. The material has conjugated main chains and functionalized polarity side-chain radicals, wherein the conjugated main chains contain Hg metal atoms; the functionalized polarity side-chain radicals comprise a high-polarity radical A with water-alcohol solubility. Due to the existence of the metal atoms in the conjugated main chains, the conjugated polymer material has the mutual metal-metal supermolecule function, and has a good current-carrier transferring characteristic; due to the existence of the radical A, the conjugated polymer material can be prepared by using a high-polarity solvent such as alcohol, can remarkably decrease the work function of a stable metal electrode, has good functions of suction filtration, injection and the like on enhanced high work function metal electrode electrons, and is applicable to manufacturing of complex multi-layer organic / polymer photoelectric devices. The conjugated metal polymer with the functionalized polarity side-chain radicals can be used as an electronic suction filtration / transferring layer to be applied to photovoltaic, light-emitting organic / polymer photoelectric devices to improve the properties of the devices.

Description

technical field [0001] The invention relates to the field of a class of conjugated polymers and macromolecule photoelectric materials, in particular to conjugated metal polymer photoelectric materials containing functionalized polar side chain groups and applications thereof. Background technique [0002] Organic / polymer solar cell devices (Organic Solar Cells, OSC, [WO 94 / 05045-A], [US 5331183-A], [WO 2002 / 101838-A]) can use large-scale , low-cost solution processing technology to prepare devices and has a wide range of application prospects. [0003] In order to realize high-efficiency organic / polymer solar cell devices, the efficient transport and extraction of electrons and holes from the cathode and anode, respectively, is the key. Therefore, many high-efficiency organic / polymer solar cell devices adopt a multilayer device structure, that is, in addition to the photoactive layer, it also contains one or more hole transport / extraction layers or electron transport / extrac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G79/00H01L51/46
CPCY02E10/549C08G61/12C08G2261/3142C08G2261/3328C08G2261/334C08G2261/3422
Inventor 黄飞刘升建张凯曹镛
Owner SOUTH CHINA UNIV OF TECH
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