Conjugated metal polymer optoelectronic materials with functionalized polar side chain groups and their applications

A technology of metal polymers and polar side chains, applied in photovoltaic power generation, circuits, electrical components, etc., can solve the problems that are rarely reported and the conjugated metal polymers have not attracted attention, and achieve reduced thickness dependence and good electronic performance. Effect of transport/extraction properties, high migration properties

Active Publication Date: 2015-10-28
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 optoelectronic materials with functionalized polar side chain groups and their applications
  • Conjugated metal polymer optoelectronic materials with functionalized polar side chain groups and their applications
  • Conjugated metal polymer optoelectronic materials with functionalized polar side chain groups and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Conjugated metal polymer photoelectric material with functionalized polar side chain group poly[2,7-diethynyl-9,9'-bis(6-N,N-diethylamino-hexyl)fluorene- Preparation of mercury] (referred to as PFE6N-Hg)

[0047] The synthetic route is as follows:

[0048]

[0049] (1) 2,7-diethynyl-9,9'-bis(6-bromo-hexyl)fluorene (monomer 4) is 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 ) Dissolve the raw materials, then add diethylamine (15mL), heat to reflux for 12h under the protection of argon, pour the reaction solution into ice water after cooling, extract with dichloromethane, concentrate and pass the concentrate to the column to obtain The product was 4.38 g, and the yield was 85%.

[00...

Embodiment 2

[0059] Conjugated metal polymer photoelectric material with functionalized polar side chain group poly[2,7-diethynyl-9,9'-bis(3-N,N-diethylamino-propyl) fluorene -Mercury] (referred to 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 1,3-dibromopropane, stir, add 20mL50% sodium hydroxide aqueous solution, 0.5g tetrabutylammonium bromide, The reaction was carried out at 50-60°C for 12 hours under the protection of argon. After cooling, the reaction solution was poured into ice water, extracted with dichloromethane and concentrated, and the concentrate was passed through a column to obtain 18.1 g of 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), 2.16-2.11 (m, 4H), 1.1...

Embodiment 5

[0093] Taking the polymer PFE6N-Hg synthesized in Example 1 as an example, it is shown that this type of polymer has anti-solvent (chlorobenzene) elution performance and can use orthogonal solvents to prepare multilayer organic / polymer solar cell devices.

[0094] Dissolve PFE6N-Hg in 1,4-dioxane, filter it with a 0.45μm organic filter membrane, and spin-coat on a common glass plate to form a film with a thickness of about 20nm. Use the UV tester (HP8453spectrophotometer) produced by HP to measure the absorbance of PFE6N-Hg after film formation, which corresponds to figure 1 Curve 1 in. Then, the PFE6N-Hg film was eluted with chlorobenzene, and the absorbance of the eluted PFE6N-Hg film was tested by UV, corresponding to figure 1 The curve in 2. By observing that the absorbance of PFE6N-Hg film does not decrease after elution with chlorobenzene, it has excellent anti-solvent elution performance.

[0095] figure 1 A graph of the ultraviolet-visible light (UV) absorbance curve of th...

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Abstract

The present invention provides a conjugated metal polymer photoelectric material containing a functionalized-polarity side-chain group and an application thereof. The material has a conjugated main chain and a functionalized-polarity side-chain group, the conjugated main chain comprising the metal atom Hg, and the functionalized-polarity side-chain group comprising a water / alcohol soluble high-polarity group A. Because the conjugated main chain comprises the metal atom, the interaction between the metal and the metal supermolecules exists in the conjugated polymer material, thereby achieving a good carrier transmission characteristic. Because the group A exists, the conjugated polymer material can be processed by using high-polarity solvent such as alcohol, and the work function of a stable metal electrode can be significantly reduced; in this way, electronic extraction and injection of a high-work-function metal electrode can be strengthened, and the conjugated polymer material is applicable to manufacturing a complicated multiply organic / polymer photoelectric device. The conjugated metal polymer containing the functionalized-polarity side-chain group can be used as an electronic extraction / transmission layer in an organic / polymer photoelectric device such as a photovoltaic device or a light-emitting device, thereby improving the device performance.

Description

Technical field [0001] The invention relates to the field of a class of conjugated polymers and polymer optoelectronic materials, in particular to conjugated metal polymer optoelectronic materials containing functionalized polar side chain groups and their applications. Background technique [0002] Organic / polymer solar cell devices (Organic Solar Cells, OSC, [WO 94 / 05045-A], [US 5331183-A], [WO 2002 / 101838-A]) can be used on a large scale due to flexible material design , 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 key is to efficiently transport and extract electrons and holes from the cathode and anode respectively. Therefore, many high-efficiency organic / polymer solar cell devices adopt a multilayer device structure, that is, in addition to the photoactive layer, they also contain one or more hole transport / extraction layers or ele...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G79/00H01L51/46
CPCC08G61/12C08G79/00C08G2261/3142C08G2261/3328C08G2261/334C08G2261/3422Y02E10/549
Inventor 黄飞刘升建张凯曹镛
Owner SOUTH CHINA UNIV OF TECH
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