CN101575505B - Blue light luminescent material with organic-inorganic hybrid structure, preparation method and application thereof - Google Patents
Blue light luminescent material with organic-inorganic hybrid structure, preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a blue light luminescent material with an organic-inorganic hybrid structure, wherein components of the blue light luminescent material comprise terminal functional polyhedraloligomeric silsesquioxane (POSS) and terminal monofunctional or difunctional luminescent molecules; and the molar ratio of the terminal functional POSS to the terminal monofunctional or difunctionalluminescent molecules is 1: 1-8. A preparation method comprises the steps of: adding the terminal functional POSS and the luminescent molecules according to the molar ratio of 1: 1-8 under the protection of N2, taking CuI as a catalyst, selecting DMF or DMSO as a solvent, controlling the reaction temperature to between 20 and 70 DEG C, reacting for 8 to 24h, filtering the reaction product, using CHCl3, MeOH, H2O, THF and Et2O to wash the reaction product, and performing vacuum drying on the reaction product to obtain the material. The blue light luminescent material is applied in the field ofthe preparation of various displays, optical communication and indoor decoration light sources. The blue light luminescent material can realize the accurate control of the number of organic illuminophores, thereby realizing effectively adjusting luminescent color purity; and preparation technology is simple, has quick reaction speed, and is environment-friendly.
Description
Technical field
The invention belongs to blue light emitting material and preparation thereof and Application Areas, particularly relate to a kind of blue light luminescent material with organic-inorganic hybrid structure and preparation thereof and application.
Background technology
The appearance of organic electroluminescence device (Organic Light-Emitting Device, OLED) has brought once huge impact to technique of display.Compare with other technique of display, OLED has that the visual angle is wide, energy consumption is low, fast response time, ultra-thin and ultra-light, and the easy significant advantage that waits of forming process can prepare full cured film device, more can realize flexible the demonstration, has obtained people's extensive concern and further investigation.
In order to realize full-color demonstration, blue light material is most important in the evolution of OLED.Be to realize one of three primary colours that full color shows because of it not only, and the energy gap of blue light material is wider, has had blue light just can realize ruddiness and green glow by methods such as energy transfers.But in the electroluminescent organic material of having succeeded in developing, blue light material is of less types.Disclose the organic electroluminescence blue-light emitting material of a class aryl ethylene compounds such as US Patent No. P5516577, representation compound is DPVBi, but the fusing point of this compound low (mp:204 ℃) has limited its range of application.Chinese patent CN1597669A has opened oxine aluminium of a kind of blue light-emitting and preparation method thereof.Chinese patent CN1854116A discloses a kind of fluorenes that will gather and has been dispersed in blue light emitting polymer membrane in the polyethylene matrix height-orientedly.Chinese patent CN1451671A discloses hyperbranched conjugated polymer of a kind of blue light-emitting and preparation method thereof.Chinese patent CN1818010A discloses a kind of blue light electroluminescent polymer based on the phenoxazine unit in the polyarylene skeleton.Chinese patent CN1699315A discloses a kind of two fluorenes volution blue light emitting materials.Chinese patent CN1800298A discloses a kind of with the blue-emitting polymer in two indeno spiral shell fluorenes unit introducing polyarylene polymkeric substance skeleton.Chinese patent CN1908113A discloses a kind of five-membered ring distyryl compounds of organic electroluminescence blue light-emitting.Although developed at present compound such as diphenylanthrancene, tetraphenylbutadiene and hexichol alkenyl benzene derivative as the blue light-emitting material, their poor stability, luminous efficiency is not high, and glow color is impure, and the light-emitting device life period that makes is of short duration.
Want to address the above problem, obtain the organic electroluminescence blue-light emitting material of excellent performance, can pass through organic inorganic hybridization, not only can integrate better the advantage of organic materials and inorganic materials, make organic-inorganic hybrid material not only have the processing characteristics of organic materials excellence, good toughness, kept also simultaneously that inorganic materials is heat-resisting, resistance to oxidation and excellent mechanical property, and can effectively reduce the association of organic molecule, reduce organic layer and interelectrode energy barrier, improve the injection efficiency in electronics, hole, thereby improve brightness, efficient and the life-span of OLED device.
POSS is a kind of novel nano structured material that occurred in recent years, and its molecular formula can be expressed as (RSiO
1.5)
n(n generally can be 6,8,10,12 etc.) has cagelike structure, and the definite nano grade inorganic kernel of rigidity, structure that is comprised of with oxygen silicon is the hybrid compounds that shell forms with the organic group R that is connected the covalent linkage connection.Can be by chemical process at the different reactive functional groups of POSS polyhedral surface bonding, it is multi-functional and highly reactive to give the POSS nanoparticle, makes the combination on molecular level of organic constituent and inorganic component.Compare with general polysiloxane, the POSS of cagelike structure has better thermotolerance, lower surface energy; Than other inorganic nano particle modified dose such as nano level clay, silicon-dioxide, titanium dioxide, calcium carbonate etc., it is simply effective that the POSS nanoparticle of cage structure not only has synthesis technique, and surface bonding power is large, monodispersity good, density is low, Heat stability is good and do not contain the advantages such as trace metal impurities.Most critical be, introduce organic group on the Si summit by chemical process, really realized the hydridization of organic-inorganic on the molecule aspect, good dispersity.In addition, though the small molecules luminous organic material is more easily purified, because of the characteristics of high-molecular luminous material, it is difficult to purify, and by the introducing of POSS, can make the macromolecular material of easily purifying.
In sum, POSS is as a kind of nanoparticle of novel texture, just causing that domestic and international researcher pays close attention to greatly.But at present research is confined to the aspects such as the mechanical property of material and thermal characteristics mostly, and relatively less to the research of material function, institute's research field also remains further to be expanded, and Patents is also less.Chinese patent CN1651438A discloses a kind of compound and its organic electroluminescence device of use based on polysilsesquioxane with organometallic complex.Xiao S. etc. (J.Pharm.Sci., 2002,91:2182) prepared MEH-PPV-POSS, PFO-POSS matrix material with the POSS end-blocking, in solution or thin slice, have identical photoluminescence spectra and electroluminescent spectrum.(Macromolecules, 2004,37 (7): 2335) synthesized a kind of star hydridization PFO material, reduced molecular aggregates, obviously improved thermal characteristics and the fluorescence quantum efficiency of material, but reaction scheme and aftertreatment are comparatively complicated such as Lin W..(the Macromol such as Lee, 2004,37 (23): the organic inorganic hybridization that 8523) has prepared take POSS as side group by series reaction such as replacement, etherificate, the additions of silicon hydrogen gathers fluorenes, the photoelectric properties of obtained device improve with the increase of POSS content, and especially electroluminescent photochromic purity obtains larger raising.(the Chem.Mater.2007 such as Jesse D.Froehlich, 19:4991) reported a kind of multi-functional POSS organic inorganic hybridization luminescent material, effectively improved the thermal characteristics of material, but its luminophore is uncontrollable in POSS adding number and hydridization molecular structure, the luminescent material that obtains is the mixture that the luminophore number does not wait, transmission ofenergy between each group is uncontrollable, and luminance purity and emission wavelength are difficult to control as a result.
Therefore, the present invention has carried out further research to function POSS organic-inorganic hybrid blue light luminescent material.
Summary of the invention
Technical problem to be solved by this invention is to propose a kind of blue light luminescent material with organic-inorganic hybrid structure and preparation and application, organic-inorganic hybrid structure blue light material of the present invention can be realized the accurate control of organic light emission group number, thereby realizes the effective adjusting to illuminant colour purity; This preparation technology is simple, and raw material sources are convenient, and speed of response is fast, and cost is low, and is environmentally friendly.
A kind of blue light luminescent material with organic-inorganic hybrid structure of the present invention, its component comprises: terminal function silsesquioxane POSS and terminal simple function or difunctionality light emitting molecule, its mol ratio are 1: 1～8.
Described terminal function POSS is terminal alkynes or terminal azide functionalities POSS, is at silsesquioxane cage structure (Si
8O
12) eight summit Si atoms on be connected with eight terminal function organic group R that carry out click chemistry reaction, its molecular formula is R
8Si
8O
12, structure is as follows:
Wherein,
Be alkyl chain or silica chain.
The reaction of described click chemistry for the function POSS of terminal alkynyl with form with light emitting molecule reaction with terminal alkynes with the light emitting molecule reaction of terminal azido-or with the function POSS of terminal azido-
Structure.
Described terminal simple function or difunctionality light emitting molecule are terminal nitrine or terminal alkynes simple function light emitting molecule or terminal nitrine or terminal alkynes difunctionality light emitting molecule.
The structure of described terminal nitrine or terminal alkynes simple function light emitting molecule is as follows:
Wherein, n=0 or 1,
Be alkyl chain;
The structure of described terminal nitrine or terminal alkynes difunctionality light emitting molecule is as follows:
Wherein, m, n=0 or 1.
Described space is alkyl, alkoxyl group, replacement or unsubstituting aromatic yl, aralkyl, aryloxy, heteroaryl, Heterocyclylalkyl or ester group.
Described π-conjugation is fluorene derivatives, carbazoles derivative, anthracene derivative, pyridine derivatives or phenylene ethylene analog derivative etc., and its structure is as follows:
Wherein, R
1And R
2Be hydrogen atom, halogen atom, cyano group, amino, alkyl, alkoxyl group, replacement or unsubstituting aromatic yl, aralkyl, aryloxy, hetero-aromatic ring, cycloalkyl or ester group.
Described organic-inorganic hybrid blue light luminescent material is based on the star small molecular blue light material of silsesquioxane organic inorganic hybridization or based on the network shape polymer blue-ray material of silsesquioxane organic inorganic hybridization.
Its component of star small molecular blue light material of described organic inorganic hybridization comprises terminal function silsesquioxane (POSS), terminal simple function light emitting molecule and terminal simple function end-blocking organic molecule, and its mol ratio is 1: n: 8-n, general molecular formula is: R '
nR "
8-nSi
8O
12, n=1～8 wherein, R ' is organic light emission small molecules chain, R " be end-blocking organic molecule chain;
With n=7, the molecular formula of described star small molecular blue light material based on the silsesquioxane organic inorganic hybridization is for being R '
7R " Si
8O
12, its feature structure is as follows:
Wherein, m=0 or 1,
Be alkyl chain.
Described its component of network shape polymer blue-ray material based on the silsesquioxane organic inorganic hybridization comprises terminal function silsesquioxane (POSS), terminal difunctionality light emitting molecule and terminal difunctionality capping group;
With x=12, y=48, z=9, described network shape polymer blue-ray material molecule formula based on the silsesquioxane organic inorganic hybridization is R " '
12R "
48(Si
8O
12)
9, its feature structure is as follows:
Wherein, m, n=0 or 1,
Be alkyl chain.
Described end-blocking organic molecule, its structure is as follows:
Wherein,
Stable without the optics active organic group for flexibility or rigidity.
Described end-blocking organic molecule, its structure is as follows:
Wherein,
Stable without the optics active organic group for flexibility or rigidity.
The glow peak wavelength of described blue light material based on the silsesquioxane organic inorganic hybridization is between 430nm～480nm, and the temperature range of thermal weight loss 50% is 450 ℃～480 ℃, 130～200 ℃ of fusing points.
The preparation method of a kind of blue light luminescent material with organic-inorganic hybrid structure of the present invention comprises:
(1) at N
2Protection is lower, and with above-mentioned end function POSS and terminal simple function light emitting molecule in molar ratio 1: n feeds intake, and wherein 1＜n≤8 are terminal function POSS and terminal difunctionality light emitting molecule in molar ratio 1: n, and 1＜n≤4 wherein are with CuI
Or with terminal function POSS, terminal simple function light emitting molecule and with the simple function capping group of corresponding function end in molar ratio 1: n: 8-n is disposable to feed intake, 1＜n≤8 wherein, or with terminal function POSS, terminal difunctionality light emitting molecule and with the difunctionality capping group of corresponding function end in molar ratio 1: n: 4-n ~ 8 are disposable to feed intake, wherein 1＜n≤4 are take CuI as catalyzer, the CuI consumption is the 0.5-10% of terminal function POSS molar weight, select DMF or DMSO as solvent, solvent load is as the criterion with the soluble reaction thing, the 1mol reactant needs the 5ml-10ml solvent, 20 ~ 70 ℃ of control temperature of reaction, reaction times 8 ~ 24h gets head product;
(2) with after the above-mentioned head product filtration, use successively CHCl
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours, and get final product.
A kind of blue light luminescent material with organic-inorganic hybrid structure of the present invention can be applicable to the fields such as various indicating meters, signboard, optical communication, upholstery light source.
The present invention is incorporated into each blue light-emitting group in the terminal monomer with alkynyl or nitrine by Heck reaction, Witting reaction, Sonogashira reaction, Wohl-Ziegler reaction etc., to obtain singly to contain sense or dual functional light emitting molecule, and can accurately control the number of organic light emission group by the change of feed ratio, and then luminous intensity, purity of color are effectively regulated.
The silsesquioxane that the present invention adopts contains 8 functional groups, can with 8 blue light emitting molecular function radical reactions, when blue light emitting molecular reaction functional group ratio less than 8 the time, for preventing that the unreacted group is further crosslinked on the silsesquioxane molecule, improve solvability or the stability of material, usually adopt the organic molecule end-blocking (technological process prepares with hybrid material) that contains the flexibility or rigidity chain.
Beneficial effect:
(1) organic-inorganic hybrid structure blue light material of the present invention can be realized the accurate control of organic light emission group number, thereby realizes the effective adjusting to illuminant colour purity;
(2) this organic-inorganic hybrid structure blue light material has Heat stability is good, easily machine-shaping, and good film-forming property, luminous efficiency is high, and glow color is pure, the characteristics such as the light-emitting device life period length that makes;
(3) this preparation technology is simple, and raw material sources are convenient, and speed of response is fast, and cost is low, and is environmentally friendly.
Description of drawings
Fig. 1 is the fluorescence spectrum figure of product in THF solution that embodiment 1 obtains;
Fig. 2 is the current density voltage curve figure of embodiment 1 obtained film;
Fig. 3 is the efficient-voltage pattern of embodiment 1 obtained film;
Fig. 4 is the brightness-voltage pattern of embodiment 1 obtained film;
Fig. 5 is the TGA graphic representation of embodiment 1 obtained product.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used for explanation the present invention and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Embodiment 1
Sodium azide POSS and 2-alkynes-9,9-dibutyl fluorenes hybrid material
With sodium azide POSS (14.58g 10mmol), 2-alkynes-9,9-dibutyl fluorenes (28.56g 80mmol) and CuI (0.19g1mmol) join in the there-necked flask, at N
2Add DMF10ml under the atmosphere, stirring at room 12 hours.Head product is used CHCl after filtering successively
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours.The product molecular formula is: (C
26SiN
3OH
34)
8Si
8O
12, productive rate 95%, glow peak wavelength: 450nm.Its THF solution fluorescence spectrum is seen Figure of description 1, makes current density voltage curve, efficient-voltage, brightness-voltage such as Fig. 2 of film～shown in Figure 4 by its spin coating, and the TGA curve as shown in Figure 5.
Sodium azide POSS and 2-(4-alkynyl vinylbenzene)-9,9-dibutyl fluorenes hybrid material
With sodium azide POSS (14.58g 10mmol), 2-(4-alkynyl vinylbenzene)-9,9-dibutyl fluorenes (32.37g 80mmol) and CuI (0.19g 1mmol) join in the there-necked flask, at N
2Add DMF10ml under the atmosphere, stirring at room 12 hours.
The product molecular formula is: (C
34SiN
3OH
40)
8Si
8O
12, head product is used CHCl after filtering successively
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours.Productive rate 95%, glow peak wavelength: 460nm.
Embodiment 3
Sodium azide POSS and 2-alkynes-9,9-dibutyl fluorenes hydridization, positive hexin end-blocking material
With sodium azide POSS (14.58g 10mmol), 2-alkynes-9,9-dibutyl fluorenes (24.99g 70mmol) and CuI (0.19g1mmol) join in the there-necked flask, at N
2Add DMF10ml under the atmosphere, stirring at room added positive hexin (0.82g 10mmol) again and clicks end-blocking after 12 hours, continued reaction 12 hours.
The product molecular formula is: (C
26SiN
3OH
34)
7(C
9SiN
3OH
18) Si
8O
12, head product is used CHCl after filtering successively
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours.Productive rate 94%, glow peak wavelength: 450nm.
With sodium azide POSS (139.32g 90mmol), 2-(4-alkynyl vinylbenzene)-9,9-dibutyl fluorenes (48.56g 120mmol), positive hexin (39.36g 480mmol) and CuI (1.71g 9mmol) join in the there-necked flask, at N
2Add DMF10ml under the atmosphere, stirring at room 12 hours.Head product is used CHCl after filtering successively
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours.The product molecular formula is: (C
47Si
2N
6O
2H
54)
12(C
9SiN
3OH
18)
48(Si
8O
12)
9Productive rate 92%, glow peak wavelength: 470nm.
Claims (13)
1. blue light luminescent material with organic-inorganic hybrid structure, its component comprises: terminal function silsesquioxane POSS and terminal simple function or difunctionality light emitting molecule, its mol ratio are 1:1～8; Wherein,
Terminal function silsesquioxane POSS is terminal alkynes or terminal azide functionalities silsesquioxane POSS, is at silsesquioxane cage structure Si
8O
12Eight summit Si atoms on be connected with eight terminal function organic group R that carry out click chemistry reaction, its molecular formula is R
8Si
8O
12, structure is as follows:
Wherein,
Be alkyl chain or silica chain;
Terminal simple function or difunctionality light emitting molecule are terminal nitrine or terminal alkynes simple function light emitting molecule or terminal nitrine or terminal alkynes difunctionality light emitting molecule;
The reaction of described click chemistry for the function silsesquioxane POSS of terminal alkynyl with form with light emitting molecule reaction with terminal alkynes with the light emitting molecule reaction of terminal azido-or with the function silsesquioxane POSS of terminal azido-
Structure.
2. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 1, it is characterized in that: the structure of described terminal nitrine or terminal alkynes simple function light emitting molecule is as follows:
Wherein, n=0 or 1,
Be alkyl chain;
The structure of described terminal nitrine or terminal alkynes difunctionality light emitting molecule is as follows:
Wherein, m, n=0 or 1.
3. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 2, it is characterized in that: described space is alkyl, alkoxyl group, replacement or unsubstituting aromatic yl, aralkyl, aryloxy, heteroaryl, Heterocyclylalkyl or ester group.
4. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 2, it is characterized in that: described π-conjugation is fluorene derivatives, carbazole derivative, anthracene derivant, pyridine derivate or phenylene ethylene derivative, and its structure is as follows:
Wherein, R
1And R
2Be hydrogen atom, halogen atom, cyano group, amino, alkyl, alkoxyl group, replacement or unsubstituting aromatic yl, aralkyl, aryloxy, hetero-aromatic ring, cycloalkyl or ester group.
5. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 1 is characterized in that: described organic-inorganic hybrid blue light luminescent material is for based on the star small molecular blue light material of silsesquioxane organic inorganic hybridization or based on the network shape polymer blue-ray material of silsesquioxane organic inorganic hybridization.
6. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 5, it is characterized in that: its component of star small molecular blue light material of described organic inorganic hybridization comprises terminal function silsesquioxane POSS, terminal simple function light emitting molecule and terminal simple function end-blocking organic molecule, its mol ratio is 1:n:8-n, and general molecular formula is: R '
nR "
8-nSi
8O
12, n=1～8 wherein, R ' is the light emitting molecule chain, R " be end-blocking organic molecule chain.
7. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 6 is characterized in that: when n=7, the molecular formula of described star small molecular blue light material based on the silsesquioxane organic inorganic hybridization is R '
7R " Si
8O
12, its feature structure is as follows:
Wherein, m=0 or 1,
Be alkyl chain.
8. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 5, it is characterized in that: described its component of network shape polymer blue-ray material based on the silsesquioxane organic inorganic hybridization comprises terminal function silsesquioxane POSS, terminal difunctionality light emitting molecule and terminal difunctionality capping group;
Described network shape polymer blue-ray material molecule formula based on the silsesquioxane organic inorganic hybridization is R " '
12R "
48(Si
8O
12)
9, its feature structure is as follows:
Wherein, m, n=0 or 1,
Be alkyl chain.
9. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 6 is characterized in that: described end-blocking organic molecule, and its structure is as follows:
Wherein,
Stable without the optics active organic group for flexibility or rigidity.
10. a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 8 is characterized in that: described capping group, and its structure is as follows:
Wherein,
Stable without the optics active organic group for flexibility or rigidity.
11. a kind of hybrid structure blue light emitting material according to claim 1, it is characterized in that: the glow peak wavelength of described blue light material based on the silsesquioxane organic inorganic hybridization is between 430nm～480nm, the temperature range of thermal weight loss 50% is 450 ℃～480 ℃, 130～200 ℃ of fusing points.
12. the preparation method of a kind of blue light luminescent material with organic-inorganic hybrid structure according to claim 1 comprises:
(1) at N
2Protection is lower, with terminal function silsesquioxane POSS and terminal simple function light emitting molecule in molar ratio 1:n feed intake, 1＜n≤8 wherein, or with terminal function silsesquioxane POSS and terminal difunctionality light emitting molecule 1:n in molar ratio, 1＜n≤4 wherein, take CuI as catalyzer, the CuI consumption is the 0.5-10% of terminal function silsesquioxane POSS molar weight, select DMF or DMSO as solvent, solvent load is as the criterion with the soluble reaction thing, the 1mol reactant needs the 5ml-10ml solvent, 20-70 ℃ of control temperature of reaction, reaction times 8-24h, unreacted function silsesquioxane POSS is terminal to click end-blocking by the capping group with the corresponding function end, and wherein the mol ratio of terminal function POSS and simple function end-cap molecule is 1:8-n, 1＜n≤8, the mol ratio of terminal function silsesquioxane POSS and difunctionality end-cap molecule is 1:4-n, and 1＜n≤4 get head product;
Or with terminal function silsesquioxane POSS, terminal simple function light emitting molecule and with the simple function capping group of corresponding function end 1:n:8-n is disposable in molar ratio feeds intake, 1＜n≤8 wherein, or with terminal function silsesquioxane POSS, terminal difunctionality light emitting molecule and with the difunctionality capping group of corresponding function end 1:n:4-n is disposable in molar ratio feeds intake, 1＜n≤4 wherein, take CuI as catalyzer, the CuI consumption is the 0.5-10% of terminal function silsesquioxane POSS molar weight, select DMF or DMSO as solvent, solvent load is as the criterion with the soluble reaction thing, the 1mol reactant needs the 5ml-10ml solvent, 20-70 ℃ of control temperature of reaction, reaction times 8-24h gets head product;
(2) with after the above-mentioned head product filtration, use successively CHCl
3, MeOH, H
2O, THF, Et
2O washing, 40 ℃ of vacuum-drying 12 hours, and get final product.
13. a blue light luminescent material with organic-inorganic hybrid structure as claimed in claim 1 is applied to the preparation of various indicating meters, signboard, optical communication, upholstery light source.
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| KR20150103472A (en) * | 2014-03-03 | 2015-09-11 | 한국과학기술연구원 | Azide-functionalized polysilsesquioxane, preparation method of the same and high-strength film using the same |
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| ES2360436B1 (en) * | 2009-11-20 | 2012-05-08 | Consejo Superior De Investigaciones Cient�?Ficas (Csic) | POLYEDRIC OLIGOMERIC SILSESQUIOXANS CONTAINING AZIDA OR AZOL GROUPS, PROCEDURE OF OBTAINING AND USES |
| CN101880477B (en) * | 2010-06-18 | 2013-11-13 | 东华大学 | POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof |
| CN103172657B (en) * | 2011-12-26 | 2016-03-30 | 北京化工大学 | Containing the functionalized cage modle polyhedral polysilsesquioxane and preparation method thereof of alkynyl |
| JP2014098147A (en) * | 2012-10-18 | 2014-05-29 | Central Glass Co Ltd | Siloxane compound, and curable composition and cured body comprising the same |
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| KR20150103472A (en) * | 2014-03-03 | 2015-09-11 | 한국과학기술연구원 | Azide-functionalized polysilsesquioxane, preparation method of the same and high-strength film using the same |
| KR101627167B1 (en) | 2014-03-03 | 2016-06-03 | 한국과학기술연구원 | Azide-functionalized polysilsesquioxane, preparation method of the same and high-strength film using the same |
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