CN107541075B - Hot-melt organopolysiloxane composition, phosphor sheet, and semiconductor device - Google Patents
Hot-melt organopolysiloxane composition, phosphor sheet, and semiconductor device Download PDFInfo
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- CN107541075B CN107541075B CN201710894231.5A CN201710894231A CN107541075B CN 107541075 B CN107541075 B CN 107541075B CN 201710894231 A CN201710894231 A CN 201710894231A CN 107541075 B CN107541075 B CN 107541075B
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 57
- 239000012943 hotmelt Substances 0.000 title claims abstract description 25
- 239000004065 semiconductor Substances 0.000 title claims abstract description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
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- 238000010438 heat treatment Methods 0.000 abstract description 18
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- HAURRGANAANPSQ-UHFFFAOYSA-N cis-2,4,6-Trimethyl-2,4,6-triphenylcyclotrisiloxane Chemical compound O1[Si](C)(C=2C=CC=CC=2)O[Si](C)(C=2C=CC=CC=2)O[Si]1(C)C1=CC=CC=C1 HAURRGANAANPSQ-UHFFFAOYSA-N 0.000 description 5
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- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZBSKZKPSSKTLNE-UHFFFAOYSA-N 4-methylpent-3-enoxysilane Chemical compound CC(=CCCO[SiH3])C ZBSKZKPSSKTLNE-UHFFFAOYSA-N 0.000 description 3
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- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 3
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- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 3
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- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 1
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- FCCRGBVYSYHQRQ-UHFFFAOYSA-N [ethenyl(dimethyl)silyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)C=C FCCRGBVYSYHQRQ-UHFFFAOYSA-N 0.000 description 1
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- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the technical field of organic silicon, and relates to a hot-melt type organopolysiloxane composition, a phosphor sheet and a semiconductor device, which comprise: (A) comprising R1 3SiO1/2Unit, R2 2SiO2/2Unit and R3SiO3/2A branched molecular structure organopolysiloxane of units; (B1) the organopolysiloxane has a straight-chain molecular structure, and two ends of a molecular chain respectively contain a hydrosilyl end cap; (B2) comprising R4 3SiO1/2Unit and R5SiO3/2A branched molecular structure organopolysiloxane of units, said component (B2) containing at least one silicon-bonded hydrosilyl group and at least one phenyl group; (C) an organopolysiloxane having vinyl groups and epoxy groups, and containing in one molecule on average at least one silicon-bonded vinyl group and at least one epoxy group; (D) a catalyst required for hydrosilylation reaction. The phosphor sheet of the present invention is solid at 25 ℃ and has low surface tackiness, and can be melted by heating and then further cured and molded to have excellent adhesion properties.
Description
Technical Field
The invention belongs to the technical field of organic silicon, and particularly relates to a hot-melt type organopolysiloxane composition, a phosphor sheet and a semiconductor device.
Background
The basic structural unit of the organosilicon polymer is composed of silica chain links, and the side chains are connected with other various organic groups through silicon atoms. Compared with other high molecular materials, the organic silicon polymer has the following outstanding properties: 1. weather resistance, the main chain of the organic silicon product is-Si-O-, has better thermal stability, irradiation resistance and weather resistance than other high polymer materials, and has longer service life under natural environment. 2. The electric insulation performance and the organosilicon products have good electric insulation performance, the dielectric loss, the voltage resistance, the corona resistance, the volume resistivity, the surface resistivity and the like of the organosilicon products are listed as pioneer insulating materials, and the electric performance of the organosilicon products is slightly influenced by temperature and frequency. Therefore, based on the above-mentioned good overall properties, organopolysiloxanes are widely used in the LED photovoltaic industry as one of the silicone products.
In general, an LED lamp with improved various performances can be obtained by dispersing a phosphor in a liquid resin for sealing an LED chip, and encapsulating the LED chip with the phosphor sheet, wherein the phosphor sheet includes the phosphor and the resin.
In recent years, in order to improve LED manufacturing processes, an encapsulating material which is solid or semi-solid at room temperature has been developed, for example, a silicone resin sheet which is semi-cured using a silicone composition containing a vinyl-based silicone resin, a silicone resin containing a hydrosilane, and a catalyst required for a hydrosilylation reaction. The encapsulating material prepared by the composition has certain practicability and improves the performance of the LED lamp, but the encapsulating material also has certain problems, such as surface viscosity at 25 ℃ which is not favorable for storage and transportation, and poor adhesive force between the phosphor sheet and the LED chip after the phosphor sheet is attached and cured with the LED chip.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: aiming at the technical problems that the phosphor sheet in the prior art has surface viscosity at 25 ℃ and has poor adhesive force between the phosphor sheet and an LED chip after being attached and cured with the LED chip, the invention provides a hot-melt type organopolysiloxane composition, a phosphor sheet and a semiconductor device.
In order to solve the above technical problems, embodiments of the present invention provide a hot-melt type organopolysiloxane composition comprising:
(A) comprising R1 3SiO1/2Unit, R2 2SiO2/2Unit and R3SiO3/2Organopolysiloxane of branched molecular structure of units, R1、R2And R3Each independently selected from methyl, vinyl or phenyl, said organopolysiloxane containing an average of at least one silicon-bonded vinyl group and at least one phenyl group, the moles of said phenyl groupsThe fraction is more than 10 percent;
(B1) the organopolysiloxane has a straight-chain molecular structure, two ends of a molecular chain respectively contain a hydrosilyl end cap, and a group bonded with silicon on a molecular main chain is methyl, phenyl or vinyl;
(B2) comprising R4 3SiO1/2Unit and R5SiO3/2Organopolysiloxane of branched molecular structure of units, R4And R5Each independently selected from methyl, vinyl or phenyl, said component (B2) containing at least one silicon-bonded hydrosilyl group and at least one phenyl group;
wherein the weight content proportion relationship of the component (B1) and the component (B2) is w1: w 2-10: 90-50: 50;
(C) an organopolysiloxane having vinyl groups and epoxy groups, and containing in one molecule on average at least one silicon-bonded vinyl group and at least one epoxy group;
(D) a catalyst required for hydrosilylation reaction.
Alternatively, the component (C) has an average unit molecular formula of,
[Me2ViSiO1/2]a1[PhMeSiO2/2]b1[R6MeSiO2/2]c1
wherein Me is methyl, Ph is phenyl, Vi is vinyl and R6Is composed of
And 0.1<a1<0.5，0.3<b1<0.8，0.1<c1<0.5。
Alternatively, the content of the vinyl group in the component (C) is 0.1 to 0.5mol/100g, and the content of the epoxy group is 0.05 to 0.50mol/100 g.
Optionally, the mass of component (C) is 0.5-5.0% of the total mass of the composition.
Alternatively, the content of the silicon-bonded vinyl group in the component (A) is 0.1 to 0.5mol/100 g.
Alternatively, the ratio of the molar mass of the silicon-bonded hydrogen atoms in the component (B1) and the component (B2) to the sum of the vinyl groups in the component (a) is 0.9 to 2.0.
Alternatively, the component (A) has the following average unit molecular formula,
[PhSiO3/2]a2[Me2ViSiO1/2]b2[MeViSiO2/2]c2，
wherein Me is methyl, Ph is phenyl and Vi is vinyl, and 0.3< a2<0.8, 0.1< b2<0.5, 0.1< c2< 0.3.
Alternatively, the component (B1) has the following average unit formula,
[R7MeSiO2/2]a3[Me2HSiO1/2]2，
wherein Me is methyl, R7Is phenyl or cyclohexyl and H is a hydrogen atom, and 0<a3<100。
Alternatively, the component (B2) has the following average unit formula,
[PhSiO3/2]a4[Me2HSiO1/2]b4，
wherein Me is methyl, Ph is phenyl and H is hydrogen, and 0.3< a4<1, 0< b4< 0.6.
Optionally, the composition in a cured state has a tensile strength of 2 to 10Mpa, an elongation at break of 10 to 100%, a refractive index of 1.47 to 1.55, and a hardness of D30 to D70 at a temperature of 25 ℃ and a humidity of 60% RH.
The present invention also provides a phosphor sheet comprising a phosphor and a resin, the phosphor being dispersed in a liquid form of the resin, the resin being a cured product of the hot-melt organopolysiloxane composition.
The invention also provides a semiconductor device comprising a light emitting element and a support for fixing the light emitting element, wherein the phosphor sheet is pasted on the light emitting element.
The embodiment provided by the invention has the beneficial effects that: compared with the prior art, the hot-melt type organopolysiloxane composition, the phosphor sheet prepared by using the composition and the semiconductor device thereof have the advantages that the composition is solid at 25 ℃, has low surface viscosity, can be melted by heating, and is further cured and molded. The phosphor sheet prepared by the heat-melting property of the composition has excellent adhesion after being attached to an LED chip, and has low surface tackiness at 25 ℃ and is convenient to store and transport.
Drawings
Fig. 1 is a schematic view of a phosphor sheet attached to an LED chip according to an embodiment of the present invention.
The reference numerals in the specification are as follows:
1. a cured phosphor sheet containing a hot-melt organopolysiloxane composition; 2. an LED chip; 3. an electrode; 4. a circuit substrate;
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects solved by the present invention more clearly apparent, the present invention is further described in detail below with reference to the accompanying drawings and 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.
In the following description, Vi is a vinyl group, H is a hydrogen atom, Me is a methyl group, Ph is a phenyl group, R6Is an epoxy group, R7Is phenyl or cyclohexyl.
The present invention provides a hot-melt organopolysiloxane composition comprising:
(A) comprising R1 3SiO1/2Unit, R2 2SiO2/2Unit and R3SiO3/2Organopolysiloxane of branched molecular structure of units, R1、R2And R3Each independently selected from methyl, vinyl or phenyl, said organopolysiloxane containing an average of at least one silicon-bonded vinyl group and at least one phenyl group, the mole fraction of said phenyl groups being greater than 10%;
(B1) the organopolysiloxane has a straight-chain molecular structure, two ends of a molecular chain respectively contain a hydrosilyl end cap, and a group bonded with silicon on a molecular main chain is methyl, phenyl or vinyl;
(B2) comprising R4 3SiO1/2Unit and R5SiO3/2Organopolysiloxane of branched molecular structure of units, R4And R5Each independently selected from methyl, vinyl or phenyl, said component (B2) containing at least one silicon-bonded hydrosilyl group and at least one phenyl group;
wherein the weight content proportion relationship of the component (B1) and the component (B2) is w1: w 2-10: 90-50: 50;
(C) an organopolysiloxane having a vinyl group and an epoxy group, and containing in one molecule on average at least one silicon-bonded vinyl group and at least one epoxy group;
(D) a catalyst required for hydrosilylation reaction.
Wherein the component (A) is one of the main components of the composition of the present invention, and the vinyl group in this component reacts with the silicon-bonded hydrogen atoms in the component (B1) and the component (B2) to form a crosslinking bond, and is cured. Component (A) is a compound comprising R1 3SiO1/2Unit, R2 2SiO2/2Unit and R3SiO3/2A branched molecular structure organopolysiloxane of units, the organopolysiloxane containing an average of at least one silicon-bonded vinyl group and at least one phenyl group; wherein R is1、R2And R3Each independently selected from methyl, vinyl or phenyl. To further control the refractive index of the cured body obtained from the composition of the present invention, the molar fraction of phenyl groups is greater than 10%.
As a preferred embodiment of the present invention, the (A) has an average unit molecular formula,
[PhSiO3/2]a2[Me2ViSiO1/2]b2[PhViSiO2/2]c2，
wherein Me is methyl, Ph is phenyl and Vi is vinyl, and 0.3< a2<0.8, 0.1< b2<0.5, 0.1< c2< 0.3.
In order to further improve the reactivity of the component (A) with the component (B1) and the component (B2), the content of the silicon-bonded vinyl group in the component (A) is 0.1 to 0.5mol/100 g.
In the present invention, component (A) is solid at 25 ℃ and a cured product of the organopolysiloxane composition comprising component (A) and other components is solid at 25 ℃ and the surface of the cured product of the composition is not tacky, and a phosphor sheet produced from the composition is solid at 25 ℃ and is not tacky on the surface of the phosphor sheet, and the phosphor sheet is more easily and conveniently stored and transported.
The component (B1) is one of the main components of the composition of the present invention, and the silicon-bonded hydrogen atoms in this component react with the vinyl groups in the component (A) to form a crosslinking bond and cure. The molecular structure of the component (B1) is a straight chain molecular structure, two ends of a molecular chain respectively contain one hydrosilyl end cap, groups bonded with silicon on a molecular main chain can be methyl, phenyl or vinyl, the mole fraction of the phenyl in the component (B1) is preferably more than 10%, and the molecular weight of the component (B1) is preferably 1500.
As one of the preferred embodiments of the present invention, the (B1) has the following average unit formula,
[R7MeSiO2/2]a3[Me2HSiO1/2]2，
wherein Me is methyl, R7Is phenyl or cyclohexyl and H is a hydrogen atom, and 0<a3<100。
In order to further improve the reactivity of the component (A1) with the component (B1) and the component (B2), the content of silicon-bonded hydrogen atoms in the component (B1) is 0.2 to 0.6mol/100 g.
The component (B2) is one of the main components of the composition of the present invention, and the silicon-bonded hydrogen atoms in this component react with the vinyl groups in the component (A) to form a crosslinking bond and cure. Component (B2) is a compound comprising R4 3SiO1/2Unit and R5SiO3/2A branched molecular structure organopolysiloxane of units, said component (B2) containing at least one silicon-bonded hydrosilyl group and at least one phenyl group; wherein R is4And R5Each independently selected from methyl, vinyl orA phenyl group. In order to further control the refractive index of the cured body obtained from the composition of the present invention, the molar fraction of the phenyl groups is preferably greater than 10%.
As one of the preferred embodiments of the present invention, the (B1) has the following average unit formula,
[PhSiO3/2]a4[Me2HSiO1/2]b4，
wherein Me is methyl, Ph is phenyl and H is hydrogen, and 0.3< a4<1, 0< b4< 0.6.
In order to further improve the reactivity of the component (A1) with the component (B1) and the component (B2), the content of silicon-bonded hydrogen atoms in the component (B2) is 0.2 to 0.5mol/100 g.
The component (C) is one of the main components of the composition of the present invention, is an organopolysiloxane having vinyl groups and epoxy groups, and contains an average of at least one silicon-bonded vinyl group and at least one epoxy group in one molecule; the component (C) is a reactive organosilicon tackifier containing epoxy groups, and because the reactive organosilicon tackifier has reactive ethylene groups, the composition containing the component (C) is prepared into a phosphor sheet and is packaged into a curing process of a semiconductor device, vinyl in the organosilicon tackifier component (C) participates in the reaction between the compositions, so that the component (C) is finally cured in the semiconductor device, and the problem that the organosilicon tackifier volatilizes or migrates and is lost in high-temperature curing or long-term lighting of the semiconductor device is avoided, so that the bonding force between the cured phosphor sheet and an LED chip is reduced; in other words, the component (C) enables excellent adhesion between the cured phosphor sheet and the LED chip without affecting the adhesion due to high-temperature curing.
As a preferred embodiment of the present invention, said (C) has the following average unit formula,
[Me2ViSiO1/2]a1[PhMeSiO2/2]b1[R6MeSiO2/2]c1
wherein Me is methyl, Ph is phenyl, Vi is vinyl and R6Is composed of
And 0.1<a1<0.5，0.3<b1<0.8，0.1<c1<0.5。
For example, the component (C) may include the following formula as a representative:
[Me2ViSiO1/2]0.2[PhMeSiO2/2]0.5[R6MeSiO2/2]0.3。
in order to further improve the adhesive property of a cured product of the composition containing the component (C) under the high-temperature condition, the content of vinyl in the component (C) is 0.1-0.5mol/100g, and the content of epoxy is 0.05-0.5mol/100 g; the mass of the component (C) accounts for 0.5-5.0% of the total mass of the composition.
In the present invention, component (D) is a catalyst which causes hydrosilylation reaction of alkenyl groups in component (A) with silicon-bonded hydrogen atoms in components (B1) and (B2). In other words, component (D) is a catalyst that promotes curing of the composition. The type of catalyst used in the present invention is not particularly limited, and any catalyst commonly used in the art may be used, for example, a platinum-based catalyst, a rhodium-based catalyst, or a palladium-based catalyst. Specific examples include: platinum black, chloroplatinic acid, alcohol solutions of chloroplatinic acid, platinum-alkenylsiloxane complexes, platinum-olefin complexes, and the like, preferably platinum-alkenylsiloxane complexes, and the present invention employs a platinum catalyst having tetramethylvinyldisiloxane as a ligand. There are no particular restrictions on the amount of component (D) used, and it is sufficient to accelerate the curing reaction of the composition.
The hot-melt type organopolysiloxane composition of the present invention may further comprise component (E) an addition reaction inhibitor for the purpose of extending the pot life of the hot-melt type organopolysiloxane composition of the present invention, the addition reaction inhibitor being a temperature-dependent substance that rapidly loses its inhibitory properties when heated to a certain extent, and causes the composition to undergo a curing reaction. The kind and amount of addition reaction inhibitor of component (E) are not particularly limited, and an inhibitor conventionally used in the art may be used, and may be added as needed, for example, in the present invention, component (E) is ethynylcyclohexanol, and is added in an amount of 0.05% by weight based on the total weight of components (A), (B1) and (B2).
In the present invention, the production methods of the components (a), (B1), (B2), (C), (D) and (E) are not particularly limited, and can be produced by a conventional manner in the art or commercially available.
In the present invention, there is no particular limitation on the content ratio relationship of the component (A) to the components (B1) and (B2), and for example, the weight ratio of the component (A) to the components (B1) and (B2) may be 1:99 to 99:1, preferably 90:10 to 10:90, more preferably 20:80 to 80: 20. As long as sufficient reaction of the alkenyl atoms in component (a) with the silicon-bonded hydrogen atoms in components (B1), (B2) is satisfied, for example, the molar mass ratio of the silicon-bonded hydrogen atoms in components (B1), (B2) to the sum of the alkenyl groups in component (a) is preferably 0.9 to 2.0.
In the present invention, the hot melt type organopolysiloxane composition can be prepared by mixing the essential components (a), (B1), and (B2), then mixing the mixed solution with the components (C) and (D), and adding the component (E) and other additives such as phosphor, pigment, luminous flux aid, heat resistance agent, and the like as necessary.
In the present invention, the hot melt type organopolysiloxane composition is formed into a resin which is solid at 25 ℃ by the interaction of components (a), (B1), (B2), (C), and (D), and in this state, the resin does not have surface tackiness, becomes a resin of melt fluidity at least 100 ℃ or higher with an increase in temperature, and during the re-solidification thereof, the resin exhibits excellent adhesive properties. The phosphor sheet and the semiconductor device produced by utilizing the above characteristics have the properties of the above hot-melt type organopolysiloxane composition in addition to the excellent properties thereof.
In the invention, the mixed composition and a certain amount of phosphor are uniformly mixed and coated on a polyethylene terephthalate (PET) film, and then the mixture is pre-cured to obtain a phosphor sheet, wherein the phosphor can be phosphor YAG-04; the phosphor sheet is then attached to a light emitting element of the semiconductor device, which is fixed by a holder on the semiconductor device, and secondary curing is performed. The curing time and temperature can vary, for example, the PET film coated with the composition and the phosphor YAG-04 can be pre-cured by holding at 50 deg.C-80 deg.C for 10-60min, and then the obtained phosphor sheet is attached to the light emitting element and held at 150 deg.C-200 deg.C for 2-4 hours, and then secondary curing is performed under a pressure of 0.5 MPa. The cured body is formed with tensile strength of 2-10MPa, elongation at break of 10-100%, refractive index of 1.47-1.55 and hardness of D30-D70 at 25 deg.c and humidity of 60% RH. In contrast, cured bodies made from conventional organopolysiloxane compositions have difficulty in forming cured products that retain the above-described good properties in terms of tensile strength, elongation at break, refractive index, and hardness, and have the advantage of excellent adhesion to LED chips.
The present invention will be described in further detail with reference to examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the following description, Vi denotes a vinyl group, Me denotes a methyl group, Ph denotes a phenyl group, H denotes a hydrogen atom, and R denotes a hydrogen atom
Synthesis example 1
1480g of phenyltrimethoxysilane, 325.65g of vinyl single end socket and 198.35g of methyl vinyl dimethoxy silane; putting into a reaction flask, cooling to 20 ℃, dropwise adding 500.0g of dilute alkali solution with pH 8 within 60 minutes, heating to 50 ℃ after dropwise adding, stirring for 1 hour, continuously refluxing and stirring for 1 hour, then adding acid to adjust the pH value to 7, adding a solvent for extraction, separating an acid water layer, washing an organic layer to neutral pH, pouring into a flask, distilling and concentrating under reduced pressure by using a vacuum water pump, and removing the solvent and low-boiling-point substances under reduced pressure to obtain the resin with the following structure:
[PhSiO3/2]0.65[MeViSiO2/2]0.13[Me2ViSiO1/2]0.22 (A-1)
this component is an organopolysiloxane which is solid at 25 ℃, has a phenyl content of 53% and a vinyl molar content of 0.300mol/100 g.
Synthesis example 2
1460g of phenyltrimethoxysilane, 200g of vinyl single end socket and 245g of methylphenyldimethoxysilane; putting into a reaction flask, cooling to 20 ℃, dropwise adding 500.0g of dilute alkali solution with pH 8 within 60 minutes, heating to 50 ℃ after dropwise adding, stirring for 1 hour, continuously refluxing and stirring for 1 hour, then adding acid to adjust the pH value to 7, adding a solvent for extraction, separating an acid water layer, washing an organic layer to neutral pH, pouring into a flask, distilling and concentrating under reduced pressure by using a vacuum water pump, and removing the solvent and low-boiling-point substances under reduced pressure to obtain the resin with the following structure:
[PhSiO3/2]0.72[Me2ViSiO1/2]0.15[MePhSiO2/2]0.13 (A-2)
this component is an organopolysiloxane which is solid at 25 ℃, has a phenyl content of 66% and a vinyl molar content of 0.120mol/100 g.
Synthesis example 3
271.65g of methyl phenyl dimethoxy silane is added into water with pH value of 3 in a dropwise manner for 1h, the temperature is maintained at 20 ℃ in the dropwise adding process, the reaction is carried out for 2h, 100g of tetramethyl disiloxane is added, the temperature is raised to 70 ℃ after the reaction is carried out for 2h, the reaction is carried out for 180 minutes, the temperature is reduced to room temperature, a solvent is added for extraction, an acid water layer is separated, an organic layer is washed to be neutral pH, a vacuum water pump is used for carrying out reduced pressure distillation and concentration, and the solvent and low-boiling-point substances are removed under reduced pressure, so that the following structural resin is obtained:
[PhMeSiO2/2]8[Me2HSiO1/2]2 (B1-1)
this component is an organopolysiloxane having a viscosity of 40 mPas at 25 ℃ and having a molar hydrogen content of 0.49mol/100g and a phenyl content of 33%.
Synthesis example 4
271.65g of methyl phenyl dimethoxy silane is dripped into water with pH value of 3 for 1h, the temperature is maintained at 20 ℃ in the dripping process, the reaction is carried out for 2h, 136g of vinyl double end socket is added, the temperature is raised to 70 ℃ after the reaction is carried out for 2h, the reaction is carried out for 180 minutes, the temperature is reduced to room temperature, a solvent is added for extraction, an acid water layer is separated, an organic layer is washed to be neutral pH value, a vacuum water pump is used for carrying out reduced pressure distillation and concentration, and the solvent and low boiling point substances are removed under reduced pressure, so that the following structural resin is obtained:
[PhMeSiO2/2]8[Me2ViSiO1/2]2 (B1-2)
this component is an organopolysiloxane having a viscosity of 62 mPas at 25 ℃ and having a molar content of vinyl groups of 0.43mol/100g and a content of phenyl groups of 33%.
Synthesis example 5
Dropping 500g of phenyltrimethoxysilane into water with the pH value of 3 for 1h, maintaining the temperature at 20 ℃ in the dropping process, reacting for 2h, adding 40g of tetramethyldisiloxane, reacting for 2h, heating to 70 ℃ for reacting for 180 minutes, cooling to room temperature, adding a solvent for extraction, separating an acid water layer, washing an organic layer to neutral pH, carrying out reduced pressure distillation and concentration by using a vacuum water pump, and removing the solvent and low-boiling-point substances under reduced pressure to obtain the resin with the following structure:
[PhSiO3/2]0.81[Me2HSiO1/2]0.19 (B2-1)
this component is an organopolysiloxane having a viscosity of 1700 mPas at 25 ℃ and having a molar hydrogen content of 0.34mol/100g and a phenyl content of 40%.
Synthesis example 6
Dropping 500g of phenyltrimethoxysilane into water with the pH value of 3 for 1h, maintaining the temperature at 20 ℃ in the dropping process, reacting for 2h, adding 270g of tetramethyldisiloxane, reacting for 2h, heating to 70 ℃ for reacting for 180 minutes, cooling to room temperature, adding a solvent for extraction, separating an acid water layer, washing an organic layer to neutral pH, carrying out reduced pressure distillation and concentration by using a vacuum water pump, and removing the solvent and low-boiling-point substances under reduced pressure to obtain the resin with the following structure:
[PhSiO3/2]0.39[Me2HSiO1/2]0.61 (B2-2)
this component is an organopolysiloxane having a viscosity of 60 mPas at 25 ℃ and having a molar hydrogen content of 0.68mol/100g and a phenyl content of 20%.
Synthesis example 7
Adding 230g of trimethyltriphenylcyclotrisiloxane, (3-glycidoxypropyl) methyldimethoxysilane 193g, dimethylvinylethoxysilane 100g and ethyl acetate 50g into a flask, stirring uniformly, dropwise adding octanol solution of chloroplatinic acid (the concentration of platinum is 5 wt%), heating to 80 ℃, reacting for 10 hours, vacuumizing to-0.095 MPa, heating to 170 ℃, and vacuumizing to remove low-boiling-point substances to obtain the resin with the following structure:
[Me2ViSiO1/2]0.23[PhMeSiO2/2]0.51[R6MeSiO2/2]0.26 (C-1)
wherein, R is6Is composed of
The component is an organosilicon polysiloxane with viscosity of 50 mPas at 25 ℃, the content of vinyl is 0.22mol/100g, and the content of epoxy is 0.18mol/100 g.
Synthesis example 8
Adding 300g of trimethyltriphenylcyclotrisiloxane, (3-glycidoxypropyl) methyldimethoxysilane 96g, dimethylvinylethoxysilane 120g and ethyl acetate 50g into a flask, stirring uniformly, dropwise adding octanol solution of chloroplatinic acid (platinum concentration is 5 wt%), heating to 80 ℃, reacting for 10 hours, vacuumizing to-0.095 MPa, heating to 170 ℃, and vacuumizing to remove low-boiling-point substances to obtain the resin with the following structure:
[Me2ViSiO1/2]0.12[PhMeSiO2/2]0.62[R6MeSiO2/2]0.26 (C-2)
wherein, R is6Is composed of
The component is an organosilicon polysiloxane with viscosity of 80 mPas at 25 ℃, the content of vinyl is 0.26mol/100g, and the content of epoxy is 0.09mol/100 g.
Synthesis example 9
Adding 360g of trimethyltriphenylcyclotrisiloxane, (3-glycidoxypropyl) methyldimethoxysilane 25g, dimethylvinylethoxysilane 45g and ethyl acetate 50g into a flask, stirring uniformly, dropwise adding octanol solution of chloroplatinic acid (platinum concentration is 5 wt%), heating to 80 ℃, reacting for 10 hours, vacuumizing to-0.095 MPa, heating to 170 ℃, and vacuumizing to remove low-boiling-point substances to obtain the resin with the following structure:
[Me2ViSiO1/2]0.08[PhMeSiO2/2]0.88[R6MeSiO2/2]0.04 (C-3)
wherein, R is6Is composed of
The component is an organosilicon polysiloxane with viscosity of 80 mPas at 25 ℃, the content of vinyl is 0.06mol/100g, and the content of epoxy is 0.03mol/100 g.
Synthesis example 10
Adding 300g of trimethyl triphenyl cyclotrisiloxane, 180g of dimethyl vinyl ethoxy silane and 50g of ethyl acetate into a flask, stirring uniformly, dropwise adding octanol solution of chloroplatinic acid (the concentration of platinum is 5 wt%), heating to 80 ℃, reacting for 10 hours, vacuumizing to-0.095 MPa, heating to 170 ℃, vacuumizing, and removing low-boiling-point substances to obtain the resin with the following structure:
[Me2ViSiO1/2]0.3[PhMeSiO2/2]0.7 (C-4)
this component was an organopolysiloxane having a viscosity of 72 mPas at 25 ℃ and a vinyl group content of 0.40mol/100 g.
Synthesis example 11
Adding 300g of trimethyltriphenylcyclotrisiloxane, (3-glycidoxypropyl) methyldimethoxysilane 120g and ethyl acetate 50g into a flask, stirring uniformly, dropwise adding an octanol solution of chloroplatinic acid (the concentration of platinum is 5 wt%), heating to 80 ℃, reacting for 10 hours, vacuumizing to-0.095 MPa, heating to 170 ℃, and vacuumizing to remove low-boiling-point substances to obtain the resin with the following structure:
[PhMeSiO2/2]0.80[R6MeSiO2/2]0.20 (C-5)
wherein, R is6Is composed of
The component is an organosilicon polysiloxane with viscosity of 96 mPas at 25 ℃, and the content of epoxy group is 0.14mol/100 g.
Practical examples 1-6 and comparative examples 1-5
Synthesis of resins (A-1) (A-2) (B1-1) (B1-2) (B2-1) (B2-2) (C-1) (C-2) (C-3) (C-4) (C-5) and prepared in examples 1-11
(D) Addition reaction catalyst: octanol solution of chloroplatinic acid (platinum concentration 5 wt%);
(E) inhibitor (B): 2-phenyl-3-butyn-2-ol.
The compositions of the present invention were obtained by mixing the compositions shown in tables 1 and 2 in the combinations shown in tables 2 (each composition is in parts by weight).
The semiconductor device LED lamp shown in FIG. 1 is packaged by adding a certain amount of fluorescent powder into the hot-melt type organopolysiloxane composition, uniformly stirring, centrifugally defoaming, coating on a PET film, heating for precuring to obtain a fluorescent sheet 1, attaching the prepared fluorescent sheet on an LED chip 2 containing an electrode 3 and a circuit substrate 4 by heating and pressurizing, and carrying out secondary curing to obtain the light-emitting semiconductor device LED lamp.
The respective physicochemical properties of the obtained compositions were evaluated by the following methods. The results are reported in tables 1 and 2.
[ hardness ]
After defoaming the obtained composition, 10g was kept at 100 ℃ for 1 hour, and then cured at 160 ℃ for 3 hours, and then hardness values were measured at three points using a Shore D hardness tester at 25 ℃ and 60% RH, and the average value was recorded.
[ tensile Strength and elongation at Break ]
After defoaming the obtained composition, a sheet having a thickness of about 2mm was prepared, cured at 100 ℃ for 1 hour and 160 ℃ for 3 hours, and then processed into a dumbbell shape, and the tensile strength and elongation at break were measured at 25 ℃ and 60% RH using a universal testing machine.
[ refractivity ]
After defoaming the obtained composition, a sheet having a thickness of about 2mm was prepared, cured at 100 ℃ for 1 hour and then at 150 ℃ for 3 hours, and the cured composition was placed on an Abbe refractometer to measure its refractive index.
[ surface tackiness ]
The obtained composition was formed into a phosphor sheet, left at 80 ℃ for 30min, cooled to 25 ℃, and the surface tackiness of the phosphor sheet was measured by hand.
[ cohesiveness ]
The obtained composition was prepared into a phosphor sheet, which was attached to an LED chip, and then placed at 160 ℃ for 3 hours and then placed in an LED device capable of emitting light. The adhesiveness of the cured phosphor sheet to the LED chip was evaluated by a method of dispensing with tweezers at 25 ℃.
TABLE 1
Remarking:
among them, o indicates excellent performance, o indicates good performance, and Δ indicates poor performance.
TABLE 2
Remarking:
among them, o indicates excellent performance, o indicates good performance, and Δ indicates poor performance.
As can be seen from tables 1 and 2:
1. as is clear from comparison of examples 1, 3 and 5, when the vinyl group content and the epoxy group content in component (C) were 0.1 to 0.5mol/100g and 0.05 to 0.5mol/100g, the phosphor sheets obtained in examples 1 and 3 had better surface tackiness and adhesiveness than the phosphor sheet obtained in example 5.
2. As is clear from comparison of examples 1, 2 and 6, when the mass of component (C) is 0.5 to 5.0% of the total mass of the composition, the phosphor sheets obtained by examples 1 to 2 are better in surface tackiness and adhesiveness than the phosphor sheet obtained by example 6.
3. As is clear from comparison of examples 1, 3 and 5 with comparative examples 4 to 5, when component (C) contains both vinyl groups and epoxy groups, the phosphor sheets obtained in examples 1, 3 and 5 have better surface tackiness and adhesiveness than those of the phosphor sheets obtained in comparative examples 4 to 5.
4. As can be seen by comparing example 1 with comparative example 1, the average unit molecular formula of component (A) is [ PhSiO ]3/2]a2[Me2ViSiO1/2]b2[MeViSiO2/2]c2And 0.3<a2<0.8，0.1<b2<0.5，0.1<c2<At 0.3, the phosphor sheet obtained in example 1 had better surface tackiness and adhesiveness than the phosphor sheet obtained in comparative example 1.
5. As can be seen by comparing example 2 with comparative example 2, the average unit molecular formula of component (B1) is [ RMeSiO2/2]a3[Me2HSiO1/2]2And 0 is<a3<At 100 f, the phosphor sheet obtained in example 2 had better surface tackiness and adhesiveness than the phosphor sheet obtained in comparative example 2.
6. As can be seen by comparing example 3 with comparative example 1, component (B2) has an average unit formula of
[PhSiO3/2]a4[Me2HSiO1/2]b4And 0.3<a4<1，0<b4<At 0.6, the phosphor sheet obtained in example 3 had better surface tackiness and adhesiveness than the phosphor sheet obtained in comparative example 3.
7. It is understood from comparison of examples 1 to 6 and comparative examples 1 to 5 that a phosphor sheet after precured without tackiness can be obtained by the present invention, the hardness after heat curing is high, and the comprehensive data of tensile strength and elongation at break is excellent, and by using the phosphor-containing sheet, a phosphor sheet with high adhesion force as attached on an LED chip is provided.
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 hot-melt organopolysiloxane composition characterized by comprising:
component (A) has the following average unit formula,
[PhSiO3/2]a2[Me2ViSiO1/2]b2[MeViSiO2/2]c2，
wherein Me is methyl, Ph is phenyl and Vi is vinyl, 0.3< a2<0.8, 0.1< b2<0.5, 0.1< c2<0.3, the molar fraction of phenyl groups is more than 10%;
(B1) the organopolysiloxane has a straight-chain molecular structure, two ends of a molecular chain respectively contain a hydrosilyl end cap, and a group bonded with silicon on a molecular main chain is methyl, phenyl or vinyl;
(B2) comprising R4 3SiO1/2Unit and R5SiO3/2A branched molecular structure of units of organopolysiloxane, wherein R4And R5Each independently selected from methyl, vinyl or phenyl, said component (B2) containing at least one silicon-bonded hydrosilyl group and at least one phenyl group;
wherein the weight content proportion relationship of the component (B1) and the component (B2) is w1: w 2-10: 90-50: 50;
(C) an organopolysiloxane having vinyl groups and epoxy groups, and containing in one molecule on average at least one silicon-bonded vinyl group and at least one epoxy group;
said component (C) having the following average unit molecular formula,
[Me2ViSiO1/2]a1[PhMeSiO2/2]b1[R6MeSiO2/2]c1
wherein Me is methyl, Ph is phenyl, Vi is vinyl and R6Is composed of
And 0.1<a1<0.5，0.3<b1<0.8，0.1<c1<0.5；
(D) A catalyst required for hydrosilylation reaction.
2. A hot-melt type organopolysiloxane composition according to claim 1, wherein the content of vinyl groups in component (C) is 0.1 to 0.5mol/100g, and the content of epoxy groups is 0.05 to 0.50mol/100 g.
3. A hot-melt organopolysiloxane composition according to claim 1, characterized in that the mass of the component (C) accounts for 0.5% to 5% of the total mass of the composition.
4. The hot-melt organopolysiloxane composition according to claim 1, wherein the content of silicon-bonded vinyl groups in component (a) is 0.1 to 0.5mol/100 g.
5. A hot-melt organopolysiloxane composition according to claim 1, characterized in that the ratio of the molar mass of the silicon-bonded hydrogen atoms in the component (B1) and the component (B2) to the sum of the vinyl groups in the component (a) is 0.9 to 2.0.
6. A hot-melt organopolysiloxane composition according to claim 1, wherein component (B1) has the following average unit formula,
[R7MeSiO2/2]a3[Me2HSiO1/2]2，
wherein Me is methyl, R7Is phenyl or cyclohexyl and H is a hydrogen atom, and 0<a3<100。
7. A hot-melt organopolysiloxane composition according to claim 1, wherein component (B2) has the following average unit formula,
[PhSiO3/2]a4[Me2HSiO1/2]b4，
wherein Me is methyl, Ph is phenyl and H is hydrogen, and 0.3< a4<1, 0< b4< 0.6.
8. A hot-melt organopolysiloxane composition according to claim 1, wherein the composition in the cured state has a tensile strength of 2 to 10MPa, an elongation at break of 10% to 100%, a refractive index of 1.47 to 1.55, and a hardness of D30 to D70 at a temperature of 25 ℃ and a humidity of 60% RH.
9. A phosphor sheet comprising a phosphor and a resin, wherein the phosphor is dispersed in a liquid form of the resin, and wherein the resin is a cured product of the hot-melt organopolysiloxane composition according to any one of claims 1 to 8.
10. A semiconductor device made of the phosphor sheet according to claim 9, characterized in that the semiconductor device comprises a light emitting element on which the phosphor sheet is pasted and a holder which fixes the light emitting element.
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| CN101443400A (en) * | 2006-05-11 | 2009-05-27 | 陶氏康宁东丽株式会社 | Adhesion-promoting agent, curable organopolysiloxane composition, and semiconductor device |
| CN101814571A (en) * | 2009-02-24 | 2010-08-25 | 信越化学工业株式会社 | Optical semiconductor device encapsulated with silicone resin |
| CN104870585A (en) * | 2012-12-21 | 2015-08-26 | 道康宁公司 | Hot-melt type curable silicone composition for compression molding or laminating |
| CN105985649A (en) * | 2015-01-30 | 2016-10-05 | 广州慧谷化学有限公司 | Curable block organopolysiloxane composition and semiconductor device |
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| CN101443400A (en) * | 2006-05-11 | 2009-05-27 | 陶氏康宁东丽株式会社 | Adhesion-promoting agent, curable organopolysiloxane composition, and semiconductor device |
| CN101814571A (en) * | 2009-02-24 | 2010-08-25 | 信越化学工业株式会社 | Optical semiconductor device encapsulated with silicone resin |
| CN104870585A (en) * | 2012-12-21 | 2015-08-26 | 道康宁公司 | Hot-melt type curable silicone composition for compression molding or laminating |
| CN105985649A (en) * | 2015-01-30 | 2016-10-05 | 广州慧谷化学有限公司 | Curable block organopolysiloxane composition and semiconductor device |
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