CN103194170A - Modified organosilicone packaging adhesive with high refraction index and preparation method of modified SiH-containing polysiloxane - Google Patents
Modified organosilicone packaging adhesive with high refraction index and preparation method of modified SiH-containing polysiloxane Download PDFInfo
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- CN103194170A CN103194170A CN2013101136945A CN201310113694A CN103194170A CN 103194170 A CN103194170 A CN 103194170A CN 2013101136945 A CN2013101136945 A CN 2013101136945A CN 201310113694 A CN201310113694 A CN 201310113694A CN 103194170 A CN103194170 A CN 103194170A
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Abstract
The invention relates to a modified organosilicone packaging adhesive with a high refraction index and a preparation method of modified SiH-containing polysiloxane. The modified polysiloxane is a mixture of a component A and a component B which are in a mass proportion of 1: (0.9-1), wherein the component A comprises vinyl-containing polysiloxane, bi-functional or multi-functional acrylic monomers or vinyl benzene monomers and a hydrosilylation catalyst according to the mass ratio of (0.65-0.95): (0.05-0.35): (2-100)*10<-6>; and the component B comprises the modified SiH-containing polysiloxane, an adhesion promoter, an ultraviolet absorber and an antioxidant according to the mass ratio of (0.94-0.997): (0.002-0.04): (0.0002-0.01): (0.0002-0.01). The modified organosilicone packaging adhesive has the characteristics of high refraction index, strong binding power, difficulty in cracking and the like.
Description
Technical field
The present invention relates to a kind of LED packaging plastic, particularly the preparation method of the polysiloxane of the hydrosilyl group-containing of a kind of modified organic silicon packaging plastic with high refractive index and modification.
Background technology
At lighting field, the mankind have experienced incandescent light, luminescent lamp energy illumination course, and the LED luminous product of based semiconductor technology is just attracting common people's sight with the huge advantage of its energy-conserving and environment-protective.LED be called as the 4th generation lighting source or green light source, have energy-saving and environmental protection, characteristics such as the life-span is long and volume is little, can be widely used in fields such as various indications, demonstration, decoration, backlight, general lighting and urban landscape.
In the process of making the power-type LED device, except chip, fluorescent material and heat dissipation technology, the encapsulation technology of LED exists significant effects to LED device preparing process and performance.Organosilicon material has advantages such as cold-resistant thermal shocking, UV resistant radiation, water white transparency, is the desirable packaged material of power-type LED.
Can be divided into two kinds of condensed type and add-on types to organosilicon encapsulating material from the mechanism of crosslinking angle.
The condensed type organic silicon packaged material is to realize crosslinking reaction by intermolecular generation condensation reaction, often has micromolecular compounds such as water, methyl alcohol, ethanol to emit in the solidification process, is easy to generate bubble and hole, does not often reach high-level encapsulation performance requirement.
The add-on type organosilicon encapsulating material is mainly realized by addition reaction of silicon with hydrogen at present, is catalyzer with the platinic compound, and no small molecules produces in solidification process, has the advantages that shrinking percentage is little, Technological adaptability good and production efficiency is high.On LED packaged material market, the development of silicon hydrogen add-on type organosilicon encapsulating material is very fast, and part has replaced existing condensed type organic silicon packaged material.
But the refractive index of the common resulting packaged material of silicon hydrogen addition is lower, and the packaged material of low-refraction is unfavorable for improving the cirtical angle of total reflection in the LED encapsulation, gets optical efficiency thereby influenced.Therefore, the research of the organosilicon type packaged material of the packaged material of high refractive index, particularly high refractive index is the focus and emphasis problem in the packaged material research.
Yet domestic research in this respect at present lags far behind the U.S. and Japan.The packaged material of the excellent property on the domestic market is substantially by the monopolization of major companies such as DOW CORNING, Japanese SHIN-ETSU HANTOTAI and Toshiba, and price is very expensive, and this development to China LED industry is totally unfavorable.Therefore, research and development have the high-performance of independent intellectual property right, the organosilicon encapsulating material of high refractive index is the important behave of guaranteeing industry healthy development.
Chinese patent literature CN102676107A discloses a kind of organic-silicon-modified cycloaliphatic epoxy resin high-power LED encapsulation glue on 06 01st, 2012, its preparation method is cured as solidifying agent with acid anhydrides then for utilizing 20%～30% silicone resin intermediate partially modified cycloaliphatic epoxy resin earlier.
Summary of the invention
Purpose of the present invention aim to provide a kind of transparent, cohesive force is strong, specific refractory power is high has modified organic silicon packaging plastic of high refractive index and preparation method thereof, to overcome weak point of the prior art.
By a kind of modified organic silicon packaging plastic with high refractive index of this purpose design, it is characterized in that described packaging plastic is mixed by mass ratio 1:0.9～1 by A component and B component to form;
Wherein, the A component comprises the acrylic ester monomer of the polysiloxane, two functionality or the polyfunctionality that contain vinyl or vinyl benzene class monomer, catalyst for addition reaction of hydrogen and silicon, wherein, the mass ratio of each material is respectively (0.65～0.95): (0.05～0.35): (2～100) * 10
-6
The B component comprises polysiloxane, adhesion promoter, ultraviolet absorbers and the antioxidant of the hydrosilyl group-containing of modification, wherein, the mass ratio of each material is respectively (0.94～0.997): (0.002～0.04): (0.0002～0.01): (0.0002～0.01).
The quality of the vinyl in the described polysiloxane that contains vinyl account for the polysiloxane that contains vinyl quality 1～10%.
Contain plural vinyl in the molecular structure of the described polysiloxane that contains vinyl, the mumber average molar mass that contains the polysiloxane of vinyl is 1000～20000g/mol.
Contain at least two vinyl-functional in the molecular structure of the acrylic ester monomer of described two functionality or polyfunctionality.
Contain in cycloaliphatic ring, phenyl ring, tristane dimethanol diacrylate and the ethoxyquin bisphenol a dimethacrylate more than one in the molecular structure of the acrylic ester monomer of described two functionality or polyfunctionality.
Specific refractory power 〉=1.50 of the molecule of the acrylic ester monomer of described two functionality or polyfunctionality.
Described vinyl benzene class monomer is Vinylstyrene.
The acrylic ester monomer of described two functionality or polyfunctionality or vinyl benzene class monomer, 5%～35% of the quality that its quality altogether is the A component.
Described catalyst for addition reaction of hydrogen and silicon is the vinyl siloxane complex of pure modification Platinic chloride or platinum.
The adding quality of described catalyst for addition reaction of hydrogen and silicon is (1～50) * 10 of the quality summation of A component and B component
-6
The quality of the silicon hydrogen in the polysiloxane of the hydrosilyl group-containing of described modification be modification hydrosilyl group-containing polysiloxane quality 0.1～1%.
Described adhesion promoter is silane coupling agent, the interpolation quality of this adhesion promoter be A component and B component total mass 0.1%～2%.
Described adhesion promoter is more than one in ethyl trimethoxy silane, isooctyltrimethoxysi,ane and the vinyltrimethoxy silane.
Described ultraviolet absorbers is the ultraviolet absorbers of maximum absorption wavelength more than 360nm, the interpolation quality of this ultraviolet absorbers be A component and B component total mass 0.01%～0.5%.
Described antioxidant is 2,6-di-t-butyl Pyrogentisinic Acid, four [β-(3, three grades of butyl of 5--4-hydroxy phenyl) propionic acid] pentaerythritol ester, two (3, the 5-tert-butyl-hydroxy phenyl) more than one in thioether and the two 12 carbon alcohol esters, the quality consumption of antioxidant be A component and B component total mass 0.01%～0.5%.
A kind of preparation method of polysiloxane of hydrosilyl group-containing of modification is characterized in that comprising following content:
At first polysiloxane and the catalyst for addition reaction of hydrogen and silicon with hydrosilyl group-containing is mixed in the there-necked flask, feeds nitrogen, in 40～50 ℃ of heated and stirred 10～30min,
Add quantitative single functionality vinyl monomer then in dropping funnel, the polysiloxane of this single functionality vinyl monomer and hydrosilyl group-containing all dewaters through the 4A of overactivation molecular sieve before adding;
Next, the temperature of there-necked flask is risen to 60～70 ℃, open the cock of dropping funnel, the control rate of addition slowly drips the single functionality vinyl monomer then, and whole dropping process control is finished in 30min～120min; Drip and finish follow-up continuation of insurance temperature reaction 1～3h, obtain the polysiloxane of the hydrosilyl group-containing of modification at last.
The quality of the silicon hydrogen base in the polysiloxane of described hydrosilyl group-containing account for hydrosilyl group-containing polysiloxane quality 0.15%～1.5%;
Described catalyst for addition reaction of hydrogen and silicon is the vinyl siloxane complex of pure modification Platinic chloride or platinum, and the consumption of catalyst for addition reaction of hydrogen and silicon is the polysiloxane of hydrosilyl group-containing and (1～50) * 10 of single functionality vinyl monomer total mass
-6
Described single functionality vinyl monomer is more than one in vinylbenzene, vinyl acetate, acrylic monomer and the vinyl ethers monomer,
The mol ratio that the consumption of single functionality vinyl monomer is pressed vinyl and silicon hydrogen base is (0.05～0.35): 1 adds.
Described acrylic monomer is methyl methacrylate, butyl methacrylate or Isooctyl methacrylate; Described vinyl ethers monomer is methoxy ethylene, ethyl vinyl ether or vinyl-n-butyl ether.
After the present invention adopts above-mentioned technical scheme, have following characteristics:
1) outward appearance is colourless transparent liquid, and A component and B component mix the back does not have segregation, no particle or gel-free;
2) A component and the mixed condition of cure of B component are: the mass ratio of A component and B component is 1:(0.9～1), 60 ℃ solidify 0.5～1.5h, and 80 ℃ solidify 1～2h again;
3) cured glue shore hardness 〉=45;
4) A component and the mixed refractive index of B component 〉=1.50;
5) LED luminous efficiency lm/W 〉=110,5000 hours light decay≤5%, 1000 hour 0 light decays of stability;
6) shrinking percentage≤0.5%;
7) thermal shock-40 ℃ (30min)～120 ℃ No. 300～400 no changes of (30min) circulation;
8) Reflow Soldering: (nothing comes off and the flavescence phenomenon for about 270 ℃ of peak temperature, about 10～30s of time length to cross twice Reflow Soldering.
The product that the present invention obtains compare with traditional organic silicon packaging glue have specific refractory power height, cohesive force by force, characteristics such as not easy to crack, many deficiencies such as it is strong to overcome traditional organic silicon packaging glue cohesive force, and ablation and specific refractory power be relatively low easily.
Embodiment
Be further described below in conjunction with the present invention of embodiment.
First embodiment
1) polysiloxane of the hydrosilyl group-containing of preparation modification:
Add the polysiloxane of 50g hydrosilyl group-containing and 0.1g mass concentration and be 2% Platinic chloride octanol solution in there-necked flask, feed nitrogen, rising temperature to 50 ℃ stirs 20min.Be warming up to 65 ℃, slowly drip 7.9g vinylbenzene then.Dropwise in about 1h.Continue insulation reaction 1h.
Wherein, the quality of the silicon hydrogen base in the polysiloxane of hydrosilyl group-containing account for hydrosilyl group-containing polysiloxane quality 0.75%; The Platinic chloride octanol solution is pure modification Platinic chloride, is that with octanol Platinic chloride to be diluted to mass concentration be 2%.
Because the consumption of catalyst for addition reaction of hydrogen and silicon is very low, when reality is used, because consumption is very little, can't weighing, so must dilute.In the present embodiment, be that with octanol the vinyl siloxane complex of pure modification Platinic chloride or platinum to be diluted to mass concentration be 2% to use.
Therefore the amount of the catalyzer of actual usefulness is: the ratio that 0.1g * 2%=0.002g, this catalyzer account for total mass is: 0.002/(50+0.1+7.9)=3.44 * 10
-5, be in (1～50) * 10
-6In the scope.
Combined with coordinate bond and the complicated molecule or the ion that form by central ion (or atom) and several ligand molecular (or ion), be commonly referred to list of coordination units.Every compound that contains list of coordination units all is called coordination compound, is called for short title complex, also is complex compound.
2) preparation of A component: the mass percent that will account for A component total mass is 90% the polysiloxane that contains vinyl (mass content of vinyl is 8%), the mass percent that accounts for A component total mass is 9.9% Vinylstyrene, and the mass percent that accounts for A component total mass is that weighing is good and mix in proportion for 0.1% Platinic chloride octanol solution (mass concentration is 2%);
3) preparation of B component: the mass percent that will account for B component total mass is the polysiloxane of the hydrosilyl group-containing of 97.8% modification, the mass percent that accounts for B component total mass be 0.5% 2,6-di-t-butyl Pyrogentisinic Acid, the mass percent that accounts for B component total mass is 0.2% ultraviolet absorbers, and the mass percent that accounts for B component total mass is that weighing is good and mix in proportion for 1.5% isooctyltrimethoxysi,ane;
Suppose B component total mass=100g, by 3) preparation of B component, have:
The polysiloxane of the hydrosilyl group-containing of modification=100 * 97.8%=97.8g,
Isooctyltrimethoxysi,ane=100 * 1.5%=1.5g,
Ultraviolet absorbers=100 * 0.2%=0.2g,
2,6-di-t-butyl Pyrogentisinic Acid=100 * 0.5%=0.5g,
Wherein, isooctyltrimethoxysi,ane belongs to adhesion promoter, and 2,6-di-t-butyl Pyrogentisinic Acid belongs to antioxidant.
4) A component and B component are pressed the curing of mass ratio 1:0.9 mixed construction.
5) test data after the curing is as shown in the table:
| Performance | After the modification | Unmodified |
| A component and the mixed refractive index of B component | 1.54 | 1.46 |
| Thermal shock cycle index no change | >600 | 320 |
| Reflow Soldering comes off preceding time length/second | >60 | 25 |
| 5000 hours light decays | 1.5% | 8% |
Wherein, a hurdle is the performance of this product after the modification, and a unmodified hurdle is the performance of common organic silicon packaging glue.
Second embodiment
1) polysiloxane of the hydrosilyl group-containing of preparation modification:
Add the polysiloxane of 50g hydrosilyl group-containing and 0.1g mass concentration and be 2% Platinic chloride octanol solution in there-necked flask, feed nitrogen, rising temperature to 50 ℃ stirs 20min.Be warming up to 65 ℃, slowly drip the 7.9g methyl methacrylate then.Dropwise in about 1h.Continue insulation reaction 1h.
Wherein, the quality of the silicon hydrogen base in the polysiloxane of hydrosilyl group-containing account for hydrosilyl group-containing polysiloxane quality 0.75%; The Platinic chloride octanol solution is pure modification Platinic chloride, is that with octanol Platinic chloride to be diluted to mass concentration be 2%.
2) preparation of A component: the mass percent that will account for A component total mass is 85% the polysiloxane that contains vinyl (mass content of vinyl is 8%), the mass percent that accounts for A component total mass is 14.9% tristane dimethanol diacrylate, and the mass percent that accounts for A component total mass is that weighing is good and mix in proportion for 0.1% Platinic chloride octanol solution (mass concentration is 2%);
3) preparation of B component: the mass percent mass percent that will account for B component total mass is the polysiloxane of the hydrosilyl group-containing of 97.8% modification, account for B component total mass mass percent 0.5% 2,6-di-t-butyl Pyrogentisinic Acid, account for the ultraviolet absorbers of the mass percent 0.2% of B component total mass, and weighing is good and mix in proportion to account for the isooctyltrimethoxysi,ane of mass percent 1.5% of B component total mass;
4) A component and B component are pressed the curing of mass ratio 1:0.9 mixed construction.
5) test data after the curing is with first embodiment.
All the other are not stated part and see first embodiment, repeat no more.
Claims (18)
1. modified organic silicon packaging plastic with high refractive index is characterized in that described packaging plastic is mixed by mass ratio 1:0.9～1 by A component and B component to form;
Wherein, the A component comprises the acrylic ester monomer of the polysiloxane, two functionality or the polyfunctionality that contain vinyl or vinyl benzene class monomer, catalyst for addition reaction of hydrogen and silicon, wherein, the mass ratio of each material is respectively (0.65～0.95): (0.05～0.35): (2～100) * 10
-6
The B component comprises polysiloxane, adhesion promoter, ultraviolet absorbers and the antioxidant of the hydrosilyl group-containing of modification, wherein, the mass ratio of each material is respectively (0.94～0.997): (0.002～0.04): (0.0002～0.01): (0.0002～0.01).
2. the modified organic silicon packaging plastic with high refractive index according to claim 1, the quality that it is characterized in that the vinyl in the described polysiloxane that contains vinyl account for the polysiloxane that contains vinyl quality 1～10%.
3. the modified organic silicon packaging plastic with high refractive index according to claim 2, it is characterized in that containing plural vinyl in the molecular structure of the described polysiloxane that contains vinyl, the mumber average molar mass that contains the polysiloxane of vinyl is 1000～20000g/mol.
4. the modified organic silicon packaging plastic with high refractive index according to claim 1 is characterized in that containing at least two vinyl-functional in the molecular structure of acrylic ester monomer of described two functionality or polyfunctionality.
5. the modified organic silicon packaging plastic with high refractive index according to claim 4 is characterized in that containing in the molecular structure of acrylic ester monomer of described two functionality or polyfunctionality in cycloaliphatic ring, phenyl ring, tristane dimethanol diacrylate and the ethoxyquin bisphenol a dimethacrylate more than one.
6. the modified organic silicon packaging plastic with high refractive index according to claim 5 is characterized in that specific refractory power 〉=1.50 of molecule of the acrylic ester monomer of described two functionality or polyfunctionality.
7. the modified organic silicon packaging plastic with high refractive index according to claim 1 is characterized in that described vinyl benzene class monomer is Vinylstyrene.
8. the modified organic silicon packaging plastic with high refractive index according to claim 1 is characterized in that acrylic ester monomer or the vinyl benzene class monomer of described two functionality or polyfunctionality, 5%～35% of the quality that its quality altogether is the A component.
9. the modified organic silicon packaging plastic with high refractive index according to claim 1 is characterized in that described catalyst for addition reaction of hydrogen and silicon is the vinyl siloxane complex of pure modification Platinic chloride or platinum.
10. the modified organic silicon packaging plastic with high refractive index according to claim 1, the adding quality that it is characterized in that described catalyst for addition reaction of hydrogen and silicon is (1～50) * 10 of the quality summation of A component and B component
-6
11. the modified organic silicon packaging plastic with high refractive index according to claim 1, the quality that it is characterized in that the silicon hydrogen in the polysiloxane of hydrosilyl group-containing of described modification be modification hydrosilyl group-containing polysiloxane quality 0.1～1%.
12. the modified organic silicon packaging plastic with high refractive index according to claim 1 is characterized in that described adhesion promoter is silane coupling agent, the interpolation quality of this adhesion promoter be A component and B component total mass 0.1%～2%.
13. the modified organic silicon packaging plastic with high refractive index according to claim 12 is characterized in that described adhesion promoter is more than one in ethyl trimethoxy silane, isooctyltrimethoxysi,ane and the vinyltrimethoxy silane.
14. the modified organic silicon packaging plastic with high refractive index according to claim 1, it is characterized in that described ultraviolet absorbers is the ultraviolet absorbers of maximum absorption wavelength more than 360nm, the interpolation quality of this ultraviolet absorbers be A component and B component total mass 0.01%～0.5%.
15. the modified organic silicon packaging plastic with high refractive index according to claim 1, it is characterized in that described antioxidant is 2,6-di-t-butyl Pyrogentisinic Acid, four [β-(3, three grades of butyl of 5--4-hydroxy phenyl) propionic acid] pentaerythritol ester, two (3, the 5-tert-butyl-hydroxy phenyl) more than one in thioether and the two 12 carbon alcohol esters, the quality consumption of antioxidant be A component and B component total mass 0.01%～0.5%.
16. the preparation method of the polysiloxane of the hydrosilyl group-containing of the modification described in claim 1 is characterized in that comprising following content:
At first polysiloxane and the catalyst for addition reaction of hydrogen and silicon with hydrosilyl group-containing is mixed in the there-necked flask, feeds nitrogen, in 40～50 ℃ of heated and stirred 10～30min,
Add quantitative single functionality vinyl monomer then in dropping funnel, the polysiloxane of this single functionality vinyl monomer and hydrosilyl group-containing all dewaters through the 4A of overactivation molecular sieve before adding;
Next, the temperature of there-necked flask is risen to 60～70 ℃, open the cock of dropping funnel, the control rate of addition slowly drips the single functionality vinyl monomer then, and whole dropping process control is finished in 30min～120min; Drip and finish follow-up continuation of insurance temperature reaction 1～3h, obtain the polysiloxane of the hydrosilyl group-containing of modification at last.
17. the preparation method of the polysiloxane of the hydrosilyl group-containing of modification according to claim 16 is characterized in that:
The quality of the silicon hydrogen base in the polysiloxane of described hydrosilyl group-containing account for hydrosilyl group-containing polysiloxane quality 0.15%～1.5%;
Described catalyst for addition reaction of hydrogen and silicon is the vinyl siloxane complex of pure modification Platinic chloride or platinum, and the consumption of catalyst for addition reaction of hydrogen and silicon is the polysiloxane of hydrosilyl group-containing and (1～50) * 10 of single functionality vinyl monomer total mass
-6
Described single functionality vinyl monomer is more than one in vinylbenzene, vinyl acetate, acrylic monomer and the vinyl ethers monomer,
The mol ratio that the consumption of single functionality vinyl monomer is pressed vinyl and silicon hydrogen base is (0.05～0.35): 1 adds.
18. the preparation method of the polysiloxane of the hydrosilyl group-containing of modification according to claim 17 is characterized in that described acrylic monomer is methyl methacrylate, butyl methacrylate or Isooctyl methacrylate;
Described vinyl ethers monomer is methoxy ethylene, ethyl vinyl ether or vinyl-n-butyl ether.
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| CN105400488A (en) * | 2015-11-28 | 2016-03-16 | 烟台德邦先进硅材料有限公司 | Low-thermal-resistance and vulcanization-resistant COB (chip on board) integrated packaging adhesive |
| CN105705599A (en) * | 2013-09-18 | 2016-06-22 | 道康宁公司 | Compositions of resin-linear organosiloxane block copolymers |
| CN115232475A (en) * | 2022-06-30 | 2022-10-25 | 江苏涌新材料科技有限公司 | Refractive index adjustable organic spherical micro-nano particle and preparation method thereof |
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| CN115232475A (en) * | 2022-06-30 | 2022-10-25 | 江苏涌新材料科技有限公司 | Refractive index adjustable organic spherical micro-nano particle and preparation method thereof |
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Application publication date: 20130710 |