CN101723966A - Composite o-hydroxyl benzylidene amino-zinc coordination compound material - Google Patents
Composite o-hydroxyl benzylidene amino-zinc coordination compound material Download PDFInfo
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- CN101723966A CN101723966A CN200910051662A CN200910051662A CN101723966A CN 101723966 A CN101723966 A CN 101723966A CN 200910051662 A CN200910051662 A CN 200910051662A CN 200910051662 A CN200910051662 A CN 200910051662A CN 101723966 A CN101723966 A CN 101723966A
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- complex material
- zinc
- composite
- zinc complex
- coordination compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 239000002131 composite material Substances 0.000 title claims description 5
- 239000000463 material Substances 0.000 title description 19
- RMTHRMLHFTYKHF-UHFFFAOYSA-N OC1=C(C=[Zn]N)C=CC=C1 Chemical compound OC1=C(C=[Zn]N)C=CC=C1 RMTHRMLHFTYKHF-UHFFFAOYSA-N 0.000 title description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 3
- 150000003751 zinc Chemical class 0.000 claims abstract description 3
- 239000011365 complex material Substances 0.000 claims abstract 6
- WERKLKZWSJALMN-UHFFFAOYSA-N [Zn].OC1=CC=CC=C1C=N Chemical compound [Zn].OC1=CC=CC=C1C=N WERKLKZWSJALMN-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- -1 o-hydroxybenzylidene Chemical group 0.000 claims description 5
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims 1
- 239000011368 organic material Substances 0.000 abstract description 4
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 3
- 239000011147 inorganic material Substances 0.000 abstract description 3
- 239000008367 deionised water Substances 0.000 abstract description 2
- 229910021641 deionized water Inorganic materials 0.000 abstract description 2
- 239000003292 glue Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000007641 inkjet printing Methods 0.000 abstract 1
- 238000009987 spinning Methods 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 4
- 238000004847 absorption spectroscopy Methods 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 229910003471 inorganic composite material Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical class O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明涉及复合邻羟基苯亚甲基胺-锌配合物材料，具体涉及一种硅氧烷改性的邻羟基苯亚甲基胺-锌配合物材料及其制备方法和在发光领域的应用。本发明将水杨醛与含胺基的硅烷偶联剂以摩尔量1∶1的比例反应，反应结束后加入去离子水水解。按配位比所需加入锌盐，搅拌。所得溶液可通过甩胶，提拉以及喷墨打印等方式制得发光薄膜。本发明制备工艺简单，成本低，所得薄膜兼具有机无机材料优点，有望用于OLED的发光层。The invention relates to a compound o-hydroxybenzylideneamine-zinc complex material, in particular to a siloxane-modified o-hydroxybenzylideneamine-zinc complex material, a preparation method thereof and an application in the field of light emission. In the present invention, the salicylaldehyde is reacted with the amino group-containing silane coupling agent at a molar ratio of 1:1, and deionized water is added for hydrolysis after the reaction is completed. Add zinc salt according to the coordination ratio and stir. The resulting solution can be used to prepare a luminescent film by means of glue spinning, pulling and inkjet printing. The preparation process of the invention is simple, the cost is low, and the obtained film has both the advantages of organic and inorganic materials, and is expected to be used for the light-emitting layer of OLED.
Description
Technical field
The present invention relates to composite o-hydroxyl benzylidene amino-zinc coordination compound material and its production and application, be specifically related to a kind of silicone-modified o-hydroxyl benzylidene amino-zinc coordination compound material and preparation method thereof and the application on luminescent device.
Background technology
Organic electroluminescence device (OLED), because with respect to traditional technique of display, distinguishing feature such as have that active illuminating, light weight, device are thin, good contrast, the restriction of no visible angle, energy consumption are low is considered to the third generation indicating meter after cathode-ray tube display (CRT) and liquid-crystal display (LCD).Wherein, blue light material is a key factor of full color OLED development.Blue light can change the light of other colors by the light switch technology on the one hand, and then realizes that directly full color is luminous.Blue light material itself lags behind the development of green glow, red light material on the other hand, becomes the bottleneck of restriction full color OLED.
Blue light material mainly is divided into small molecules and two aspects of polymer at present.Small molecules needs vacuum evaporation when fabricate devices, energy consumption height, device size are subjected to the evaporated device limitation of size, and crystallization easily, influences the work-ing life of device.Macromolecular material is the common more complicated of technology when synthetic.And no matter small molecules still is the defective that macromolecular material all has organic materials itself, low such as physical strength, poor heat stability is subject to moisture effects etc.By the organic/inorganic composite material of sol-gel technique preparation,, become the popular direction of material development because of often having both the advantageous property of organic and inorganic material.While also provides new direction for the development of OLED luminescent material.
Summary of the invention
The purpose of this invention is to provide the compound blue emitting material of a kind of organic-inorganic, to solve the above-mentioned problems in the prior art.
Another object of the present invention provides a kind of preparation method of above-mentioned materials.
Silicone-modified o-hydroxyl benzylidene amino-zinc coordination compound material provided by the present invention is to prepare by operational path shown in Figure 1, now is presented below:
(1) salicylic aldehyde (5-hydroxy benzaldehyde) and amino containing silane coupling agent are joined in the solvent reflux with 1: 1 ratio of molar weight.
(2) in reaction solution, add an amount of tetraethoxy (comprise and not adding) and suitable quantity of water, stir.
(3) in reaction solution, add an amount of zinc salt, stir.
(4) room temperature is static.
The o-hydroxyl benzylidene amino-zinc coordination compound material of prepared organic inorganic compounding of the present invention has following characteristics:
(1) has organic materials, inorganic materials advantage concurrently.
(2) emission blue light.
(3) can be by whirl coating, lift and inkjet technology prepares luminescent device.
(4) under organic light emission component high density fluorescent quenching not taking place, has overcome because of preventing that the fluorescence concentration quenching from improving the shortcoming that electroconductibility that inorganic component brings descends.
Description of drawings
The operational path of Fig. 1 silicone-modified o-hydroxyl benzylidene amino-zinc coordination compound material provided by the invention.
A component peaks only appears in the gas-chromatography that is extracted reaction solution among Fig. 2 embodiment 1 in spectrogram, illustrate only to have a kind of component in the solution.
The mass spectrum of the unique component of extract reaction solution after gas-chromatography among Fig. 3 embodiment 1, it is that 325 places have a molecular ion peak at nucleo plasmic relation, coincide with the molecular ion peak of the silicone-modified o-hydroxyl benzylidene amino that provides among the embodiment 1, proved that the unique component in extracting reaction solution among the embodiment 1 is a silicone-modified o-hydroxyl benzylidene amino provided by the invention.
The ethanolic soln and the film of the silicone-modified o-hydroxyl benzylidene amino-zinc coordination compound material that provides among Fig. 4 embodiment 2, and the ultraviolet-visible absorption spectroscopy of the silicone-modified o-hydroxyl benzylidene amino ethanolic soln that provides among the embodiment 1.From the contrast of three absorption curves, can prove thoroughly carrying out of coordination reaction.
The liquid state of the silicone-modified o-hydroxyl benzylidene amino-zinc coordination compound material that provides among Fig. 5 embodiment 2 and the luminescent spectrum of film.Can find that film can send the blue light of 462nm under uviolizing.
Embodiment
Further specify the present invention below by embodiment.
Embodiment 1
1.22 gram (0.01 mole) salicylic aldehydes (5-hydroxy benzaldehyde) and 2.22 gram (0.01 mole) 3-amine propyl group-triethoxyl silanes are joined in 200 milliliters of dehydrated alcohols magnetic agitation and reflux 48 hours.The reaction solution that takes a morsel gas chromatograph-mass spectrometer analysis, and measure its purple visible absorption spectra.Obtain Fig. 2, Fig. 3 and result shown in Figure 4.
Repeat embodiment 1, then reaction solution is cooled to room temperature, in reaction solution, add 0.3 ml deionized water, magnetic agitation 24 hours.In reaction solution, add 1.10 gram Zinc diacetate dihydrates, magnetic agitation 24 hours.Test its ultraviolet-visible absorption spectroscopy and fluorescence Spectra.And the mode of solution by spin-coating be coated onto in the clean sheet glass.Test its ultraviolet-visible absorption spectroscopy and fluorescence spectrum.Obtain Fig. 4 and result shown in Figure 5.
Claims (5)
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| Application Number | Priority Date | Filing Date | Title |
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| CN200910051662A CN101723966A (en) | 2009-05-21 | 2009-05-21 | Composite o-hydroxyl benzylidene amino-zinc coordination compound material |
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| CN200910051662A CN101723966A (en) | 2009-05-21 | 2009-05-21 | Composite o-hydroxyl benzylidene amino-zinc coordination compound material |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102157697A (en) * | 2011-01-27 | 2011-08-17 | 中国科学院上海硅酸盐研究所 | Electroluminescent device using organically-inorganically hybridized material as luminescent layer and manufacturing method thereof |
| WO2016120153A1 (en) * | 2015-01-26 | 2016-08-04 | Henkel Ag & Co. Kgaa | Organic zinc complexes as catalysts for condensation reactions |
-
2009
- 2009-05-21 CN CN200910051662A patent/CN101723966A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102157697A (en) * | 2011-01-27 | 2011-08-17 | 中国科学院上海硅酸盐研究所 | Electroluminescent device using organically-inorganically hybridized material as luminescent layer and manufacturing method thereof |
| WO2016120153A1 (en) * | 2015-01-26 | 2016-08-04 | Henkel Ag & Co. Kgaa | Organic zinc complexes as catalysts for condensation reactions |
| US10138329B2 (en) | 2015-01-26 | 2018-11-27 | Henkel Ag & Co. Kgaa | Organic zinc complexes as catalysts for condensation reactions |
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Open date: 20100609 |