CN112979954A - Light-emitting device packaging material, synthetic method thereof and packaging adhesive - Google Patents
Light-emitting device packaging material, synthetic method thereof and packaging adhesive Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
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Abstract
The invention belongs to the field of packaging materials, and discloses a light-emitting device packaging material, a synthesis method thereof and packaging glue, wherein the light-emitting device packaging material has the following structure: (PhSiO)3/2)a(R1R2SiO2/2)b(R3SiO3/2)c(R4MeSiO3/2)d(R5SiO3/2)e(R6MeSiO3/2)f(Vi‑Me2SiO1/2)g(ii) a Wherein R is1Is one of methyl and phenyl, R2Is one of methyl, phenyl and vinyl, R3Is one of gamma-glycidoxypropyl, beta- (3, 4-epoxycyclohexyl) ethyl and gamma-methacryloxypropyl, R4Is one of gamma-glycidoxypropyl and gamma-methacryloxypropyl, R5Is one of trifluoropropyl, perfluorooctyl and perfluorodecyl, R6Is trifluoropropyl; a. b, c, d, e, f and g are non-negative numbers, a, b, g are not zero, c and d are not zero at the same time, e and f are not zero at the same time, and a + b + c + d + e + f + g is 1. The light-emitting device packaging material provided by the invention has good adhesive strength, optical performance and moisture resistance.
Description
Technical Field
The invention relates to the field of packaging materials, in particular to a light-emitting device packaging material, a synthesis method thereof and packaging glue.
Background
The light emitting device package refers to a package of a light emitting chip. Here, the light emitting device may be an LED (semiconductor light emitting diode) device. The encapsulation of light emitting devices places special requirements on the encapsulation material.
The light emitting device package requires that the package material has good optical properties such as light transmittance and refractive index; but also requires good sealing of the encapsulating material. The good sealing performance can effectively protect the lamp wick and prevent the chip from being exposed in humid air to lose efficacy.
In the prior art, the packaging material for packaging the light-emitting device has the problems of low bonding strength, low refractive index and poor moisture resistance.
Disclosure of Invention
Aiming at the problems of low bonding strength, low refractive index and poor moisture resistance of the packaging material in the prior art, the invention provides a light-emitting device packaging material, a synthesis method thereof and packaging glue, so as to improve the bonding strength, the refractive index and the moisture resistance of the packaging material.
The invention provides a light-emitting device packaging material, which has the following structure:
(PhSiO3/2)a(R1R2SiO2/2)b(R3SiO3/2)c(R4MeSiO3/2)d(R5SiO3/2)e(R6MeSiO3/2)f(Vi-Me2SiO1/2)g；
wherein R is1Is one of methyl and phenyl, R2Is one of methyl, phenyl and vinyl, R3Is gamma-glycidoxypropyl, beta- (3, 4-epoxycyclohexyl)One of ethyl and gamma-methacryloxypropyl, R4Is one of gamma-glycidoxypropyl and gamma-methacryloxypropyl, R5Is one of trifluoropropyl, perfluorooctyl and perfluorodecyl, R6Is trifluoropropyl;
a. b, c, d, e, f and g are non-negative numbers, a, b, g are not zero, c and d are not zero at the same time, e and f are not zero at the same time, and a + b + c + d + e + f + g is 1.
The invention also provides a synthesis method of the light-emitting device packaging material, which comprises the following steps:
taking trialkoxysilane, dialkoxysilane and vinyl end capping agent as raw materials, carrying out a first reaction in a mixed solvent system to obtain a first reaction liquid after the reaction is finished, and processing the first reaction liquid through a first purification procedure to obtain a first product;
carrying out a second reaction on the first product, a silane coupling agent and fluorine-containing siloxane, obtaining a second reaction solution after the reaction is finished, and treating the second reaction solution through a second purification program to obtain a second product;
the silane coupling agent is epoxy hydrocarbon silane and/or (methyl) acryloyl oxysilane, and the second product is phenyl vinyl fluorosilicone resin.
Optionally, the fluorine-containing siloxane is selected from at least one of trifluoropropyltrimethoxysilane, trifluoropropyltriethoxysilane, methyltrifluoropropyldimethoxysilane, perfluorooctyltrimethoxysilane and perfluorodecyltrimethoxysilane;
the mol number of the fluorine-containing siloxane is 2 to 5 percent of the total mol number of the raw materials.
Optionally, the mixed solvent system comprises water and a water-soluble solvent, wherein the water-soluble solvent is selected from at least one of methanol, ethanol and isopropanol;
the mass of the water-soluble solvent is 0.3-0.8 times of the total mass of the raw materials;
the number of moles of water is 1 to 3 times the number of moles of hydrolyzable groups of the raw material.
Optionally, the catalyst of the first reaction is an acid catalyst selected from at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, trifluoromethanesulfonic acid, acetic acid, oxalic acid, p-toluenesulfonic acid, and acid clay; the mass ratio of the acid catalyst to the water is 0.5: 99.5-5: 95;
the catalyst of the second reaction is an alkali catalyst, and the alkali catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium ethoxide and potassium ethoxide; and the mass of the alkali catalyst is 2-8 ppm of the total mass of the reactant and the solvent participating in the second reaction.
Optionally, the trialkoxysilane is phenyltrimethoxysilane and/or phenyltriethoxysilane, and the mole number of the trialkoxysilane is 60-80% of the total mole number of the raw materials;
the dialkoxysilane is alkyl dialkoxysilane and/or vinyl dialkoxysilane, and the alkyl dialkoxysilane is selected from at least one of methyl phenyl dimethoxy silane, diphenyl dimethoxy silane, methyl phenyl diethoxy silane, diphenyl diethoxy silane, dimethyl dimethoxy silane and dimethyl diethoxy silane; the vinyl dialkoxysilane is vinyl methyl diethoxysilane and/or vinyl methyl dimethoxy silane; the mole number of the dialkoxysilane is 10 to 15 percent of the total mole number of the raw materials;
the vinyl end-capping agent is at least one selected from 1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, 1, 3-divinyl-1, 1,3, 3-tetramethyldisilazane, vinyl dimethyl methoxysilane and vinyl dimethyl ethoxysilane, and the vinyl end-capping agent accounts for 15-20% of the total mole number of the raw materials.
Optionally, the epoxyhydrocarbyl silane is selected from at least one of gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropyltriethoxysilane, gamma-glycidoxypropylmethyldimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane and beta- (3, 4-epoxycyclohexyl) ethyltriethoxysilane;
the (meth) acryloyloxysilane is at least one selected from the group consisting of γ -methacryloyloxypropyltrimethoxysilane, γ -methacryloyloxypropylmethyldimethoxysilane and γ -methacryloyloxypropyltriethoxysilane;
the mole number of the silane coupling agent is 10-15% of the total mole number of the raw materials.
Optionally, the reaction temperature of the first reaction is 50-85 ℃, and the reaction time is 3-6 h;
the reaction temperature of the second reaction is 60-100 ℃, and the reaction time is 3-10 h.
Optionally, the first purging procedure includes:
adding water and a first extracting agent into the first reaction liquid to form a first water layer and a first organic layer, extracting and separating for multiple times to enable the first organic layer to be neutral, obtaining a first extraction liquid after separation, and distilling the first extraction liquid under reduced pressure at 70-90 ℃;
the second decontamination procedure comprises:
and adding water and a second extracting agent into the second reaction liquid to form a second water layer and a second organic layer, extracting and separating for multiple times to enable the second organic layer to be neutral, separating to obtain a second extraction liquid, and distilling the second extraction liquid under reduced pressure at 90-150 ℃.
The invention also provides a packaging adhesive which comprises phenyl hydrogen-containing silicone oil, ethynyl cyclohexanol, a platinum catalyst and the light-emitting device packaging material, wherein the light-emitting device packaging material is phenyl vinyl fluorosilicone resin;
the phenyl vinyl fluorosilicone resin and the phenyl hydrogen-containing silicone oil are prepared according to the following molar weight of vinyl: mixing the silicon-hydrogen bond molar weight of 0.7-1.25 to form base rubber;
the mass of the ethynyl cyclohexanol is 0.3-0.8% of that of the base rubber;
the mass of the platinum catalyst is 0.3-0.8% of that of the base rubber.
The light-emitting device packaging material (namely phenyl vinyl fluorosilicone resin) provided by the invention has good intermiscibility with other packaging materials (such as phenyl hydrogen-containing silicone oil), and the packaging adhesive prepared by mixing the phenyl vinyl fluorosilicone resin and the other packaging materials has good adhesive strength with a light-emitting chip, and also has good optical performance (higher refractive index, colorless and transparent) and moisture resistance. In addition, the synthesis method of the light-emitting device packaging material provided by the invention also has the following advantages: low raw material cost, mild reaction, simple preparation process operation and stable product quality, and is suitable for industrial production.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects solved by the present invention more apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The light-emitting device packaging material provided by the embodiment of the invention has the following structure:
(PhSiO3/2)a(R1R2SiO2/2)b(R3SiO3/2)c(R4MeSiO3/2)d(R5SiO3/2)e(R6MeSiO3/2)f(Vi-Me2SiO1/2)g；
wherein R is1Is one of methyl and phenyl, R2Is one of methyl, phenyl and vinyl, R3Is one of gamma-glycidoxypropyl, beta- (3, 4-epoxycyclohexyl) ethyl and gamma-methacryloxypropyl, R4Is one of gamma-glycidoxypropyl and gamma-methacryloxypropyl, R5Is one of trifluoropropyl, perfluorooctyl and perfluorodecyl, R6Is trifluoropropyl, Me is methyl, Vi is vinyl;
a. b, c, d, e, f and g are non-negative numbers, a, b, g are not zero, c and d are not zero at the same time, e and f are not zero at the same time, and a + b + c + d + e + f + g is 1.
The embodiment of the invention also provides a synthesis method of the light-emitting device packaging material, which comprises the following steps:
taking trialkoxysilane, dialkoxysilane and vinyl end capping agent as raw materials, carrying out a first reaction in a mixed solvent system to obtain a first reaction liquid after the reaction is finished, and processing the first reaction liquid through a first purification procedure to obtain a first product;
carrying out a second reaction on the first product, a silane coupling agent and fluorine-containing siloxane, obtaining a second reaction solution after the reaction is finished, and treating the second reaction solution through a second purification program to obtain a second product;
the silane coupling agent is epoxy hydrocarbon silane and/or (methyl) acryloyl oxysilane, and the second product is phenyl vinyl fluorosilicone resin.
In this embodiment, the trialkoxysilane is phenyltrimethoxysilane and/or phenyltriethoxysilane. The mole number of the trialkoxysilanesis 60-80% of the total mole number of the raw materials. Here, the starting materials include trialkoxysilanes, dialkoxysilanes, and vinyl blocking agents. The total mole number of the raw materials refers to the total mole number of the three substances of trialkoxysilane, dialkoxysilane and vinyl blocking agent.
The dialkoxysilane is at least one of alkyl dialkoxysilane and/or vinyl dialkoxysilane, and the alkyl dialkoxysilane is at least one of methyl phenyl dimethoxysilane, diphenyl dimethoxysilane, methyl phenyl diethoxysilane, diphenyl diethoxysilane, dimethyl dimethoxysilane and dimethyl diethoxysilane; the vinyldialkoxysilane is vinylmethyldiethoxysilane and/or vinylmethyldimethoxysilane. The mole number of the dialkoxy silane is 10 to 15 percent of the total mole number of the raw materials.
The vinyl blocking agent is at least one selected from 1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, 1, 3-divinyl-1, 1,3, 3-tetramethyldisilazane, vinyl dimethyl methoxysilane and vinyl dimethyl ethoxysilane. The vinyl end capping agent accounts for 15 to 20 percent of the total mole number of the raw materials.
A mixed solvent system refers to a solvent system suitable for carrying out the first reaction. Here, the respective starting materials are carried out in a mixed solvent system. Understandably, suitable reaction conditions for the first reaction, such as catalyst, reaction temperature, reaction time, and the like, can be determined based on the nature of the reactants and actual experimental results. After the reaction is completed, the first reaction solution needs to be treated. The first purification process may refer to a water washing operation of the first reaction solution. The catalyst added in the first reaction is an acid catalyst, and after the reaction is finished, the acid catalyst and the redundant water in the first reaction liquid need to be removed by using a first purification procedure. Herein, the first reaction may refer to a cohydrolytic polycondensation reaction occurring between trialkoxysilane, dialkoxysilane, and vinyl blocking agent.
The first reaction solution is treated by a first purification procedure to obtain a first product. The first product was a colorless and transparent solution containing a phenyl vinyl silicone oligomer. The first product may be used as a reactant for the second reaction.
The reactants of the second reaction include the first product, a silane coupling agent, and a fluorosilicone. Here, the second reaction may refer to a polycondensation reaction occurring between the first product, the silane coupling agent, and the fluorine-containing siloxane.
The silane coupling agent is epoxyhydrocarbon silane and/or (methyl) acryloyloxy silane. Wherein the epoxyhydrocarbon silane is selected from at least one of gamma-glycidoxypropyltrimethoxysilane, gamma-glycidoxypropyltriethoxysilane, gamma-glycidoxypropylmethyldimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane and beta- (3, 4-epoxycyclohexyl) ethyltriethoxysilane. The (meth) acryloyloxysilane may be at least one of γ -methacryloyloxypropyltrimethoxysilane, γ -methacryloyloxypropylmethyldimethoxysilane and γ -methacryloyloxypropyltriethoxysilane. The mole number of the silane coupling agent is 10-15% of the total mole number of the raw materials. Preferably, the mole number of the silane coupling agent is 12 to 13 percent of the total mole number of the raw materials.
The fluorine-containing siloxane is at least one selected from trifluoropropyltrimethoxysilane, trifluoropropyltriethoxysilane, methyltrifluoropropyldimethoxysilane, perfluorooctyltrimethoxysilane and perfluorodecyltrimethoxysilane. The mol number of the fluorine-containing siloxane is 2 to 5 percent of the total mol number of the raw materials. Preferably, the mol number of the fluorine-containing siloxane is 3 to 4 percent of the total mol number of the raw materials.
Understandably, suitable reaction conditions for the second reaction, such as catalyst, reaction temperature and reaction time, etc., can be determined based on the nature of the reactants and the actual experimental results. The second purification process may refer to a water washing operation of the second reaction solution. The catalyst added in the second reaction is an alkali catalyst, and the alkali catalyst and the redundant solvent in the second reaction liquid need to be removed by using a second purification procedure after the reaction is finished.
And treating the mixture after the second reaction by a second purification program to obtain a second product. The second product is colorless and transparent phenyl vinyl silicone resin. The generated phenyl vinyl silicone resin can react with phenyl hydrogen-containing silicone oil and other additives to generate packaging adhesive. The packaging adhesive containing the packaging material prepared by the synthesis method provided by the embodiment has good adhesion performance, moisture resistance and refractive index.
Optionally, the fluorine-containing siloxane is at least one selected from trifluoropropyltrimethoxysilane, trifluoropropyltriethoxysilane, methyltrifluoropropyldimethoxysilane, perfluorooctyltrimethoxysilane and perfluorodecyltrimethoxysilane. The mol number of the fluorine-containing siloxane is 2 to 5 percent of the total mol number of the raw materials.
Optionally, the mixed solvent system comprises water and a water-soluble solvent, wherein the water-soluble solvent is selected from at least one of methanol, ethanol and isopropanol;
the mass of the water-soluble solvent is 0.3-0.8 times of the total mass of the raw materials;
the number of moles of water is 1 to 3 times the number of moles of hydrolyzable groups of the raw material.
Optionally, the catalyst of the first reaction is an acid catalyst, and the acid catalyst comprises at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, trifluoromethanesulfonic acid, acetic acid, oxalic acid, p-toluenesulfonic acid and acid clay; the mass ratio of the acid catalyst to the water is 0.5: 99.5-5: 95;
the catalyst of the second reaction is an alkali catalyst, and the alkali catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium ethoxide and potassium ethoxide; the mass of the alkali catalyst is 2-8 ppm of the total mass of the reactant and the solvent participating in the second reaction.
Optionally, the trialkoxysilane is phenyltrimethoxysilane and/or phenyltriethoxysilane, and the mole number of the trialkoxysilane is 60-80% of the total mole number of the raw materials;
the dialkoxysilane is at least one of alkyl dialkoxysilane and/or vinyl dialkoxysilane, and the alkyl dialkoxysilane is at least one of methyl phenyl dimethoxysilane, diphenyl dimethoxysilane, methyl phenyl diethoxysilane, diphenyl diethoxysilane, dimethyl dimethoxysilane and dimethyl diethoxysilane; the vinyldialkoxysilane is vinylmethyldiethoxysilane and/or vinylmethyldimethoxysilane. The mole number of the dialkoxy silane is 10 to 15 percent of the total mole number of the raw materials;
the vinyl blocking agent is at least one selected from 1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, 1, 3-divinyl-1, 1,3, 3-tetramethyldisilazane, vinyl dimethyl methoxysilane and vinyl dimethyl ethoxysilane. The vinyl end capping agent accounts for 15 to 20 percent of the total mole number of the raw materials.
Optionally, the silane coupling agent comprises an epoxyhydrocarbyl silane and/or a (meth) acryloxy silane;
the epoxy hydrocarbon silane is at least one of gamma-glycidyl ether oxygen propyl trimethoxy silane, gamma-glycidyl ether oxygen propyl triethoxy silane, gamma-glycidyl ether oxygen propyl methyl dimethoxy silane, beta- (3, 4-epoxy cyclohexyl) ethyl trimethoxy silane and beta- (3, 4-epoxy cyclohexyl) ethyl triethoxy silane;
(meth) acryloxysilane selected from at least one of gamma-methacryloxypropyltrimethoxysilane, gamma-methacryloxypropylmethyldimethoxysilane and gamma-methacryloxypropyltriethoxysilane;
the mole number of the silane coupling agent is 10-15% of the total mole number of the raw materials.
Optionally, the reaction temperature of the first reaction is 50-85 ℃, and the reaction time is 3-6 h;
the reaction temperature of the second reaction is 60-100 ℃, and the reaction time is 3-10 h.
In this embodiment, the reaction temperature of the first reaction may be 50 to 85 ℃, and preferably 70 ℃. The reaction time is 3-6 h, preferably 5 h.
The reaction temperature of the second reaction may be 60 to 100 ℃, and preferably 80 ℃. The reaction time is 3-10 h, preferably 8 h.
Optionally, the first purging procedure comprises:
adding water and a first extracting agent into the first reaction liquid to form a first water layer and a first organic layer, extracting and separating for multiple times to enable the first organic layer to be neutral, obtaining a first extraction liquid after separation, and distilling the first extraction liquid under reduced pressure at 70-90 ℃;
the second decontamination procedure includes:
and adding water and a second extracting agent into the second reaction liquid to form a second water layer and a second organic layer, extracting and separating for multiple times to enable the second organic layer to be neutral, separating to obtain a second extraction liquid, and distilling the second extraction liquid under reduced pressure at 90-150 ℃.
In this embodiment, the organic extractant may be at least one of ethyl acetate, methyl acetate, ethyl propionate, toluene, and xylene.
In the first purification procedure, the main operations include water washing of the first reaction solution and a solvent removal operation (i.e., distillation under reduced pressure) after the water washing. The purpose of the first purification procedure is to obtain a neutral, less solvent containing first product. The first product was a colorless and transparent solution of phenyl vinyl silicone oligomer.
In the second purification procedure, the main operations include water washing of the second reaction solution and a solvent removal operation (i.e., distillation under reduced pressure) after the water washing. The purpose of the second purification procedure is to obtain a second product that is neutral, with most of the solvent removed. The second product is colorless transparent phenyl vinyl fluorosilicone resin.
The embodiment of the invention also provides packaging adhesive, which comprises phenyl hydrogen-containing silicone oil, ethynyl cyclohexanol, a platinum catalyst and the light-emitting device packaging material provided by the embodiment, wherein the light-emitting device packaging material is phenyl vinyl fluorosilicone resin;
mixing phenyl hydrogen-containing silicone oil and phenyl vinyl fluorosilicone resin according to the proportion of 0.7-1.25 of vinyl molar weight/silicon hydrogen bond molar weight to form base adhesive;
the mass of the ethynyl cyclohexanol is 0.3-0.8% of that of the base rubber;
the mass of the platinum catalyst is 0.3-0.8% of that of the base rubber.
In this embodiment, the addition amounts of the phenyl vinyl fluorosilicone resin and the phenyl hydrogen silicone oil are as follows: the molar weight of the vinyl group/the molar weight of the silicon-hydrogen bond is 0.7 to 1.25. Preferably, the ratio is 1. The mass of the ethynyl cyclohexanol is 0.3-0.8% of that of the base rubber. Preferably, the mass of ethynylcyclohexanol is 0.5% of the mass of the base gum. The mass of the catalyst is 0.3-0.8% of that of the base rubber. Preferably, the mass of the platinum catalyst is 0.5% of the mass of the base rubber. Preferably, the platinum catalyst is platinum.
Example 1
350g of phenyltrimethoxysilane, 150g of methylphenyldimethoxysilane, 80g of tetramethyldivinyldisiloxane monomer and 100g of ethanol were sequentially added to a 2L four-neck flask equipped with a thermometer, mechanical stirring, a reflux condenser and a constant pressure dropping funnel, and stirred in a 35 ℃ oil bath for 10 minutes. Then a mixture of 17.6g of concentrated sulfuric acid and 208g of deionized water was dropped into the four-necked flask over 20 minutes. The temperature of the liquid in the four-mouth flask is controlled not to exceed 65 ℃ in the dropping process. And after the dropwise addition is finished, controlling the temperature of the system within 70-72 ℃ and reacting for 5 hours. 400g of xylene was added as an extractant, the acid catalyst was removed by washing with pure water, the organic layer was separated, and the organic layer was repeatedly washed with water to neutrality. And (3) carrying out reduced pressure distillation at 70-90 ℃ to remove water, thus obtaining a colorless and transparent phenyl vinyl silicone resin oligomer solution.
58g of gamma-glycidoxypropyltrimethoxysilane, 20g of trifluoropropyltrimethoxysilane and 0.24g of KOH were added to the phenyl vinyl silicone oligomer solution, and the mixture was stirred in an oil bath at 80 ℃ for 8 hours. And after the reaction is finished, adding dimethylbenzene and water, stirring and mixing, standing and separating an organic layer, repeatedly washing the organic layer to be neutral, and then carrying out reduced pressure distillation at 90-150 ℃ to remove the solvent and low molecular substances, thereby obtaining the colorless and transparent phenyl vinyl fluorosilicone resin with adhesiveness.
Example 2
350g of phenyltrimethoxysilane, 100g of diphenyldimethoxysilane, 70g of tetramethyldivinyldisiloxane monomer and 100g of ethanol were sequentially added to a 2L four-neck flask equipped with a thermometer, mechanical stirring, a reflux condenser and a constant pressure dropping funnel, and stirred in a 35 ℃ oil bath for 10 minutes. Then, a mixed solution of 16.2g of concentrated sulfuric acid and 200g of deionized water is dripped into the four-neck flask within 20 minutes, and the temperature of the liquid in the four-neck flask is controlled not to exceed 65 ℃ in the dripping process. And after the dropwise addition is finished, controlling the temperature of the system within 70-72 ℃ and reacting for 5 hours. 400g of xylene was added as an extractant, the acid-removing catalyst was washed off with pure water, the organic layer was separated, and the organic layer was repeatedly washed with water to neutrality. And (3) carrying out reduced pressure distillation at 70-90 ℃ to remove water, thus obtaining a colorless and transparent phenyl vinyl silicone resin oligomer solution.
60g of gamma-glycidoxypropylmethyldimethoxysilane, 20g of trifluoropropyltriethoxysilane and 0.24g of KOH are added to the phenyl vinyl silicone resin oligomer solution, and the mixture is stirred and reacted for 8 hours in an oil bath kettle at 80 ℃. After the reaction is finished, adding dimethylbenzene and water, stirring and mixing, standing and separating an organic layer, and repeatedly washing the organic layer to be neutral. And then carrying out reduced pressure distillation at the temperature of 90-150 ℃, and removing the solvent and low molecular substances to obtain the colorless and transparent phenyl vinyl fluorosilicone resin with adhesive property.
Example 3
350g of phenyltrimethoxysilane, 100g of methylphenyldimethoxysilane, 50g of vinylmethyldiethoxysilane, 50g of tetramethyldivinyldisiloxane monomer and 100g of ethanol were placed in a 2L four-necked flask equipped with a thermometer, mechanical stirring, reflux condenser and constant pressure dropping funnel in this order, and stirred in a 35 ℃ oil bath for 10 minutes. Then, a mixed solution of 17.6g of concentrated sulfuric acid and 210g of deionized water is dripped into the four-neck flask within 20 minutes, and the temperature of the liquid in the four-neck flask is controlled not to exceed 65 ℃ in the dripping process. And after the dropwise addition is finished, controlling the temperature of the system within 70-72 ℃ and reacting for 5 hours. 400g of xylene was added as an extractant, the acid-removing catalyst was washed off with pure water, the organic layer was separated, and the organic layer was repeatedly washed with water to neutrality. And (3) carrying out reduced pressure distillation at 70-90 ℃ to remove water, thus obtaining a colorless and transparent phenyl vinyl silicone resin oligomer solution.
To the phenyl vinyl silicone resin oligomer solution were added 50g of gamma-methacryloxypropyl trimethoxysilane, 20g of methyltrifluoropropyldimethoxysilane and 0.24g of KOH, and the reaction was continued for 8 hours with stirring in an oil bath at 80 ℃. And after the reaction is finished, adding dimethylbenzene and water, stirring and mixing, standing and separating an organic layer, repeatedly washing the organic layer to be neutral, and then carrying out reduced pressure distillation at 90-150 ℃ to remove the solvent and low molecular substances, thereby obtaining the colorless and transparent phenyl vinyl fluorosilicone resin with adhesiveness.
Example 4
350g of phenyltrimethoxysilane, 120g of dimethyldimethoxysilane, 60g of tetramethyldivinyldisiloxane monomer and 100g of ethanol were sequentially added to a 2L four-neck flask equipped with a thermometer, mechanical stirring, a reflux condenser and a constant pressure dropping funnel, and stirred in a 35 ℃ oil bath for 10 minutes. Then, a mixed solution of 16.8g of concentrated sulfuric acid and 200g of deionized water is dripped into the four-neck flask within 20 minutes, and the temperature of the liquid in the four-neck flask is controlled not to exceed 65 ℃ in the dripping process. And after the dropwise addition is finished, controlling the temperature of the system within 70-72 ℃ and reacting for 5 hours. 400g of xylene was added as an extractant, the acid-removing catalyst was washed off with pure water, the organic layer was separated, and the organic layer was repeatedly washed with water to neutrality. And (3) carrying out reduced pressure distillation at 70-90 ℃ to remove water, thus obtaining a colorless and transparent phenyl vinyl silicone resin oligomer solution.
60g of gamma-methacryloxypropylmethyldimethoxysilane, 20g of perfluorooctyltrimethoxysilane and 0.24g of KOH were added to the phenyl vinyl silicone oligomer solution, and the reaction was continued for 8 hours with stirring in an oil bath at 80 ℃. After the reaction is finished, adding dimethylbenzene and water, stirring and mixing, standing and separating an organic layer, and repeatedly washing the organic layer to be neutral. And then carrying out reduced pressure distillation at the temperature of 90-150 ℃, and removing the solvent and low molecular substances to obtain the colorless and transparent phenyl vinyl fluorosilicone resin with adhesive property.
Example 5
350g of phenyltrimethoxysilane, 80g of diphenyldimethoxysilane, 50g of dimethyldimethoxysilane, 50g of vinylmethyldiethoxysilane, 50g of tetramethyldivinyldisiloxane monomer and 100g of ethanol were placed in a 2L four-necked flask equipped with a thermometer, mechanical stirring, reflux condenser and constant pressure dropping funnel in this order, and stirred in a 35 ℃ oil bath for 10 minutes. Then, a mixed solution of 17.6g of concentrated sulfuric acid and 208g of deionized water is dripped into the four-neck flask within 20 minutes, and the temperature of the liquid in the four-neck flask is controlled not to exceed 65 ℃ in the dripping process. And after the dropwise addition is finished, controlling the temperature of the system within 70-72 ℃ and reacting for 5 hours. 400g of xylene was added as an extractant, the acid-removing catalyst was washed off with pure water, the organic layer was separated, and the organic layer was repeatedly washed with water to neutrality. And (3) carrying out reduced pressure distillation at 70-90 ℃ to remove water, thus obtaining a colorless and transparent phenyl vinyl silicone resin oligomer solution.
60g of beta- (3, 4-epoxycyclohexyl) ethyltriethoxysilane, 20g of perfluorodecyltrimethoxysilane and 0.24g of KOH were added to the phenyl vinyl silicone oligomer solution, and the reaction was continued for 8 hours with stirring in an oil bath at 80 ℃. After the reaction is finished, adding dimethylbenzene and water, stirring and mixing, standing and separating an organic layer, and repeatedly washing the organic layer to be neutral. And then carrying out reduced pressure distillation at the temperature of 90-150 ℃, and removing the solvent and low molecular substances to obtain the colorless and transparent phenyl vinyl fluorosilicone resin with adhesive property.
Five different base adhesives were prepared from phenyl hydrogen silicone oil UC232 (produced by calix union chemical limited) and the phenyl vinyl fluorosilicone resins of examples 1 to 5 in a ratio of vinyl molar weight/silicon hydrogen bond molar weight of 1.05. Then, 0.5% of ethynylcyclohexanol (produced by alatin reagent company) and 0.5% of catalyst are added into each base adhesive respectively to obtain the packaging adhesives 1-5 (the serial numbers of the packaging adhesives correspond to those of the embodiments one by one).
Comparative example 1
Vinyl phenyl silicone resin RH-SP605-3 (Zhejiang Runzhe chemical new material Co., Ltd.) and phenyl hydrogen-containing silicone oil UC232 (Jiaxing Co., Ltd.) are mixed according to the proportion of vinyl molar weight/silicon hydrogen bond molar weight being 1.05 to obtain base glue, and 0.5% of ethynylcyclohexanol (produced by Aladdin reagent Co., Ltd.) in the mass of base glue and 0.5% of catalyst in the mass of base glue are respectively added into various base glues to obtain the packaging glue 6.
And respectively detecting the bonding strength, the light transmittance, the refractive index and the moisture resistance of the packaging adhesive 1-6, wherein the specific detection method is as follows.
Method for testing adhesive strength: the gap between two PPA boards (PPA, Polyphthalamide) (or PPA silver brackets, aluminum sheets, copper sheets or stainless steel) (width: 25 mm; length: 50 mm; thickness: 1mm) was filled with the above-mentioned potting adhesive according to the test method of GB/T13936-1992. And baking the sample in a hot air circulating oven at 150 ℃ for 3 hours for solidification, and cooling the solidified sample to room temperature to obtain a first test sample. And (3) in a tensile testing machine, testing the stress condition of the sample by stretching in the horizontal direction, and representing the bonding strength of the packaging adhesive according to the stress condition of the first test sample.
And (3) testing light transmittance: the space between two glass plates (width: 25mm, length: 25mm, thickness: 2mm) was filled with the above-mentioned encapsulating adhesive (thickness of the encapsulating adhesive was 2mm), and the resultant was baked in a hot air circulating oven at 150 ℃ for 3 hours to be cured, and then taken out and cooled to obtain a second test sample. The light transmittance of the second test specimen was measured at 25 ℃ by means of a spectrophotometer (measuring range of 400nm to 700nm, optical path: 0.1 cm). Measuring the transmittance T of the glass1And then measuring the light transmittance T of the second test specimen2. Then calculating the light transmittance T of the packaging adhesive according to the light transmittance obtained by the two measurements, wherein the calculation formula is
The refractive index test method comprises the following steps: according to the SH/T0724 testing method, a proper amount of the packaging adhesive is taken, a plurality of drops of the sample are dripped on the capillary surface of the auxiliary prism of the Abbe refractometer, the auxiliary prism is closed, and the lock knob is screwed. The mirrors are adjusted so that incident light enters the prism assembly while viewing from the measuring telescope to maximize the field of view. And adjusting the ocular lens to make the field of view quasi-silk clearest. The handle is turned to increase the scale value gradually until the color light band or black-white critical line appears in the visual field. The dispersion eliminating handle is rotated to make a clear bright and dark critical line appear in the field of view. Refractive index readings were recorded.
The moisture resistance test method comprises the following steps: dispensing 1-6 of packaging glue on the LED5050 support respectively, wherein the glue amount is flush with that of the PPA support, curing for 3h at 150 ℃, and cooling to room temperature to obtain the LED5050 device. And (3) putting 56 LED5050 devices in red ink, boiling for 4h, taking out, respectively putting on a heating plate (T is 250 +/-5 ℃) and baking for 1min, observing the peeling between the colloid and the bracket, and the number of cracked materials and counting the abnormal rate, wherein if no abnormal or low abnormal rate indicates that the material has excellent moisture resistance.
The data of the bonding strength, the light transmittance, the refractive index and the moisture resistance of the packaging adhesive 1-6 are shown in tables 1 and 2.
TABLE 1 adhesion Strength (in MPa), refractive index and light transmittance data for encapsulation pastes 1-6
As can be seen from Table 1, the adhesive strength of the encapsulant prepared in examples 1-5 is significantly higher than that of comparative example 6, and the encapsulant has good refractive index and light transmittance.
Table 2 moisture resistance test data for products made with encapsulation pastes 1-6
| Peel/PCS | cracking/PCS | Abnormal rate/%) | Conclusion on moisture resistance | |
| Example 1 | 1 | 0 | 1.8 | Superior food |
| Example 2 | 0 | 0 | 0 | Optimization of |
| Example 3 | 2 | 1 | 3.6 | Superior food |
| Example 4 | 1 | 1 | 1.8 | Superior food |
| Example 5 | 2 | 1 | 3.6 | Superior food |
| Comparative example | 20 | 22 | 40 | Difference (D) |
Remarking: the number of LED5050 devices used in the experiments of examples and comparative examples was 56PCS (pieces).
As can be seen from the data in Table 2, the moisture resistance of the products prepared by the packaging adhesives 1-5 is much higher than that of the packaging adhesive 6. Therefore, the phenyl vinyl fluorosilicone resin prepared in examples 1 to 5 has good moisture resistance.
Therefore, the light-emitting device packaging material (i.e., phenyl vinyl fluorosilicone resin) provided by the embodiment of the invention has good compatibility with other packaging materials (such as phenyl hydrogen-containing silicone oil), can be used for manufacturing packaging glue of a light-emitting device, improves the bonding strength of the packaging glue and a light-emitting chip, and the packaging glue has good optical performance (higher refractive index, colorless and transparent), and a product obtained after the packaging glue is cured has good light transmittance and moisture resistance. Meanwhile, the synthesis method of the light-emitting device packaging material provided by the embodiment also has the following advantages: low preparation complexity, simple and convenient operation, low raw material cost, mild reaction conditions, strong operability, stable product quality and easy industrial production.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A light emitting device encapsulation material having the structure:
(PhSiO3/2)a(R1R2SiO2/2)b(R3SiO3/2)c(R4MeSiO3/2)d(R5SiO3/2)e(R6MeSiO3/2)f(Vi-Me2SiO1/2)g；
wherein R is1Is one of methyl and phenyl, R2Is one of methyl, phenyl and vinyl, R3Is one of gamma-glycidoxypropyl, beta- (3, 4-epoxycyclohexyl) ethyl and gamma-methacryloxypropyl, R4Is one of gamma-glycidoxypropyl and gamma-methacryloxypropyl, R5Is one of trifluoropropyl, perfluorooctyl and perfluorodecyl, R6Is trifluoropropyl;
a. b, c, d, e, f and g are non-negative numbers, a, b, g are not zero, c and d are not zero at the same time, e and f are not zero at the same time, and a + b + c + d + e + f + g is 1.
2. A method for synthesizing a light emitting device packaging material, comprising:
taking trialkoxysilane, dialkoxysilane and vinyl end capping agent as raw materials, carrying out a first reaction in a mixed solvent system to obtain a first reaction liquid after the reaction is finished, and processing the first reaction liquid through a first purification procedure to obtain a first product;
carrying out a second reaction on the first product, a silane coupling agent and fluorine-containing siloxane, obtaining a second reaction solution after the reaction is finished, and treating the second reaction solution through a second purification program to obtain a second product;
the silane coupling agent is epoxy hydrocarbon silane and/or (methyl) acryloyl oxysilane, and the second product is phenyl vinyl fluorosilicone resin.
3. The method for synthesizing a light-emitting device encapsulating material according to claim 2, wherein the fluorine-containing siloxane is at least one selected from the group consisting of trifluoropropyltrimethoxysilane, trifluoropropyltriethoxysilane, methyltrifluoropropyldimethoxysilane, perfluorooctyltrimethoxysilane, and perfluorodecyltrimethoxysilane;
the mol number of the fluorine-containing siloxane is 2 to 5 percent of the total mol number of the raw materials.
4. The method for synthesizing a light emitting device encapsulating material according to claim 2, wherein the mixed solvent system comprises water and a water-soluble solvent selected from at least one of methanol, ethanol, and isopropanol;
the mass of the water-soluble solvent is 0.3-0.8 times of the total mass of the raw materials;
the number of moles of water is 1 to 3 times the number of moles of hydrolyzable groups of the raw material.
5. The method for synthesizing a light-emitting device encapsulating material according to claim 4, wherein the catalyst for the first reaction is an acid catalyst selected from at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, trifluoromethanesulfonic acid, acetic acid, oxalic acid, p-toluenesulfonic acid, and acid clay; the mass ratio of the acid catalyst to the water is 0.5: 99.5-5: 95;
the catalyst of the second reaction is an alkali catalyst, and the alkali catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium ethoxide and potassium ethoxide; and the mass of the alkali catalyst is 2-8 ppm of the total mass of the reactant and the solvent participating in the second reaction.
6. The method for synthesizing a light emitting device packaging material according to claim 2, wherein the trialkoxysilane is phenyltrimethoxysilane and/or phenyltriethoxysilane, and the molar number of the trialkoxysilane is 60-80% of the total molar number of the raw materials;
the dialkoxysilane is alkyl dialkoxysilane and/or vinyl dialkoxysilane, and the alkyl dialkoxysilane is selected from at least one of methyl phenyl dimethoxy silane, diphenyl dimethoxy silane, methyl phenyl diethoxy silane, diphenyl diethoxy silane, dimethyl dimethoxy silane and dimethyl diethoxy silane; the vinyl dialkoxysilane is vinyl methyl diethoxysilane and/or vinyl methyl dimethoxy silane; the mole number of the dialkoxysilane is 10 to 15 percent of the total mole number of the raw materials;
the vinyl end-capping agent is at least one selected from 1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, 1, 3-divinyl-1, 1,3, 3-tetramethyldisilazane, vinyl dimethyl methoxysilane and vinyl dimethyl ethoxysilane, and the vinyl end-capping agent accounts for 15-20% of the total mole number of the raw materials.
7. The method for synthesizing a light emitting device encapsulating material according to claim 2, wherein the epoxyalkyl silane is at least one member selected from the group consisting of γ -glycidoxypropyltrimethoxysilane, γ -glycidoxypropyltriethoxysilane, γ -glycidoxypropylmethyldimethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane and β - (3, 4-epoxycyclohexyl) ethyltriethoxysilane;
the (meth) acryloyloxysilane is at least one selected from the group consisting of γ -methacryloyloxypropyltrimethoxysilane, γ -methacryloyloxypropylmethyldimethoxysilane and γ -methacryloyloxypropyltriethoxysilane;
the mole number of the silane coupling agent is 10-15% of the total mole number of the raw materials.
8. The method for synthesizing the light emitting device packaging material according to claim 2, wherein the reaction temperature of the first reaction is 50 to 85 ℃, and the reaction time is 3 to 6 hours;
the reaction temperature of the second reaction is 60-100 ℃, and the reaction time is 3-10 h.
9. The method of synthesizing a light emitting device encapsulant as set forth in claim 2 wherein the first purging procedure includes:
adding water and a first extracting agent into the first reaction liquid to form a first water layer and a first organic layer, extracting and separating for multiple times to enable the first organic layer to be neutral, obtaining a first extraction liquid after separation, and distilling the first extraction liquid under reduced pressure at 70-90 ℃;
the second decontamination procedure comprises:
and adding water and a second extracting agent into the second reaction liquid to form a second water layer and a second organic layer, extracting and separating for multiple times to enable the second organic layer to be neutral, separating to obtain a second extraction liquid, and distilling the second extraction liquid under reduced pressure at 90-150 ℃.
10. An encapsulating adhesive comprising phenyl-containing hydrogen-containing silicone oil, ethynyl cyclohexanol, a platinum catalyst, and the light-emitting device encapsulating material according to claim 1, wherein the light-emitting device encapsulating material is phenyl vinyl fluorosilicone resin;
the phenyl vinyl fluorosilicone resin and the phenyl hydrogen-containing silicone oil are prepared according to the following molar weight of vinyl: mixing the silicon-hydrogen bond molar weight of 0.7-1.25 to form base rubber;
the mass of the ethynyl cyclohexanol is 0.3-0.8% of that of the base rubber;
the mass of the platinum catalyst is 0.3-0.8% of that of the base rubber.
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