WO2014200110A1 - Composition de silicium réactive, thermoplastique réactif, produit durci et dispositif semi-conducteur photoélectrique - Google Patents

Composition de silicium réactive, thermoplastique réactif, produit durci et dispositif semi-conducteur photoélectrique Download PDF

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WO2014200110A1
WO2014200110A1 PCT/JP2014/065831 JP2014065831W WO2014200110A1 WO 2014200110 A1 WO2014200110 A1 WO 2014200110A1 JP 2014065831 W JP2014065831 W JP 2014065831W WO 2014200110 A1 WO2014200110 A1 WO 2014200110A1
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亮介 山▲崎▼
吉武　誠
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東レ・ダウコーニング株式会社
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    • H01L33/58—Optical field-shaping elements
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Definitions

  • the present invention relates to a reactive silicone composition, a reactive thermoplastic, a cured product, and an optical semiconductor device.
  • a curable silicone composition that cures by hydrosilylation reaction is used as a protective agent or coating agent for optical semiconductor elements in optical semiconductor devices such as photocouplers, light-emitting diodes, and solid-state imaging elements; Has been.
  • a composition used as a light reflecting material for example, either a vinyl group or an allyl group and a thermosetting addition reactivity having a structure in which a hydrogen atom is directly bonded to a silicon atom
  • the visible light average reflectance of 80% or more addition-curable silicone resin composition (see Patent Document 2).
  • These compositions have problems such as low mold filling, easy formation of voids and burrs, and poor mold releasability in transfer molding, injection molding, or compression molding. There is also a problem that the speed is slow and the workability of the molding operation is poor.
  • cured products obtained by curing these compositions have the advantage of less discoloration due to heat and light, but have problems such as high linear expansion coefficient and low mechanical strength at high temperatures, There is a problem that the reflectivity is insufficient and the mechanical strength is greatly reduced by heat and light.
  • the present invention relates to a reactive silicone composition capable of forming a reactive thermoplastic, a reactive thermoplastic that once fluidizes when heated, and then gives a cured product, a decrease in mechanical strength and discoloration due to heat and light.
  • An object of the present invention is to provide a cured product having high light reflectivity and excellent mold releasability, and an optical semiconductor device having high light emission efficiency, low heat deterioration and light deterioration of the light reflecting material, and excellent reliability. .
  • the reactive silicone composition of the present invention comprises: (A) Average unit formula: (R 1 3 SiO 1/2 ) a (R 1 2 SiO 2/2 ) b (R 1 SiO 3/2 ) c (SiO 4/2 ) d (R 2 O 1/2 ) e (Wherein R 1 is the same or different and is a phenyl group, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms, provided that 30 to 80 mol% of all R 1 s ) Is a phenyl group, 10 to 20 mol% of all R 1 is an alkenyl group, R 2 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a, b, c, d, and e are 0 ⁇ a ⁇ 0.30, 0 ⁇ b ⁇ 0.70, 0.3 ⁇ c ⁇ 0.9, 0 ⁇ d ⁇ 0.20, 0 ⁇ e
  • the reactive thermoplastic of the present invention is characterized in that the hydrosilylation reaction of the above reactive silicone composition is allowed to proceed until a conversion of 70 to 95% is achieved.
  • the cured product of the present invention is obtained by heating the above-mentioned reactive thermoplastic to 100 ° C. or higher, and is characterized by having a solid or a viscosity of 1,000,000 Pa ⁇ s or higher at 300 ° C. Or the above-mentioned reactive silicone composition is cured.
  • the optical semiconductor device of the present invention is characterized in that a light reflecting material is formed from the above cured product.
  • the reactive silicone composition of the present invention is characterized in that it can form a reactive thermoplastic.
  • the reactive thermoplastic of the present invention is characterized by being fluidized once heated and then giving a cured product.
  • the cured product of the present invention is characterized in that the mechanical strength is not lowered or discolored by heat or light, the light reflectance is high, and the mold releasability is excellent.
  • the optical semiconductor device of the present invention is characterized by high luminous efficiency, low thermal degradation and light degradation of the light reflecting material, and excellent reliability.
  • FIG. 1 is a cross-sectional view of an LED which is an example of an optical semiconductor device of the present invention.
  • (A) component is the main component of this composition, average unit formula: (R 1 3 SiO 1/2 ) a (R 1 2 SiO 2/2 ) b (R 1 SiO 3/2 ) c (SiO 4/2 ) d (R 2 O 1/2 ) e It is organopolysiloxane represented by these.
  • R 1 Are the same or different, a phenyl group, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms.
  • R 1 examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group.
  • R 1 Examples of the alkenyl group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group.
  • the phenyl group content is R 1 In the range of 30 to 80 mol%, preferably all R 1 In the range of 60 to 75 mol%.
  • the phenyl group content is at least the lower limit of the above range, the resulting reactive thermoplastic has good room temperature hardness and high temperature flow characteristics, and the resulting cured product has mechanical strength.
  • the hardness at high temperature of the obtained cured product is good when it is not more than the upper limit of the above range.
  • the alkenyl group content is in the range of 10 to 20 mol%. This is because when the content of the alkenyl group is not less than the lower limit of the above range, the resulting cured product has good hardness at room temperature. This is because the mechanical strength is good.
  • R 2 Is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 2 examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • a is a general formula: R 1 3 SiO 1/2 Is a number satisfying 0 ⁇ a ⁇ 0.30, preferably 0 ⁇ a ⁇ 0.25. This is because the hardness at room temperature of the obtained cured product is good when a is not more than the upper limit of the above range.
  • b is a general formula: R 1 2 SiO 2/2 Is a number satisfying 0 ⁇ b ⁇ 0.70, and when forming a reactive thermoplastic, satisfies 0.10 ⁇ b ⁇ 0.70. It is preferably a number, and more preferably a number satisfying 0.15 ⁇ b ⁇ 0.60. This is obtained when b is equal to or higher than the lower limit of the above range, and the resulting thermoplastic thermoplastic resin has good room temperature hardness and high temperature flow characteristics, while being equal to or lower than the upper limit of the above range. This is because the hardness of the cured product at room temperature is good.
  • C is a general formula: R 1 SiO 3/2 And a number satisfying 0.3 ⁇ c ⁇ 0.9, preferably a number satisfying 0.35 ⁇ c ⁇ 0.85, more preferably , 0.40 ⁇ c ⁇ 0.80.
  • D is a general formula: SiO 4/2 And is a number satisfying 0 ⁇ d ⁇ 0.20, preferably 0 ⁇ b ⁇ 0.10. This is because the mechanical strength of the obtained cured product is good when d is not more than the upper limit of the above range.
  • E is a general formula: R 2 O 1/2 Is a number satisfying 0 ⁇ e ⁇ 0.10.
  • the component (A) usually has a molecular weight distribution and is a mixture of a plurality of organopolysiloxanes.
  • the component (A) may be a mixture of separately prepared organopolysiloxanes, but each organopolysiloxane is 0 ⁇ a ⁇ 0.30, 0 ⁇ b ⁇ 0. 70, 0.3 ⁇ c ⁇ 0.9, 0 ⁇ d ⁇ 0.20, and 0 ⁇ e ⁇ 0.10.
  • Component (B) is an optional component for adjusting the viscosity of the composition and adjusting the hardness and mechanical strength of the resulting cured product.
  • R 3 3 SiO (R 3 2 SiO) m SiR 3 3 It is organopolysiloxane represented by these. Where R 3 Are the same or different, a phenyl group, an alkyl group having 1 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms.
  • R 3 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group.
  • R 3 Examples of the alkenyl group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group. In the formula, all R 3 Of these, the phenyl group content is in the range of 30 to 70 mol%, and preferably in the range of 40 to 60 mol%.
  • R 3 At least one of is an alkenyl group. This is because this component is taken into the curing reaction when it has an alkenyl group.
  • m is an integer in the range of 10 to 100, preferably an integer in the range of 10 to 50. When m is not less than the lower limit of the above range, the resulting cured product has good mechanical strength, and when it is not more than the upper limit of the above range, the resulting composition has good handling workability. Because.
  • the content of the component (B) is an amount in the range of 0 to 40 parts by mass, preferably in the range of 0 to 20 parts by mass with respect to 100 parts by mass of the component (A). Is the amount. This is because the hardness of the obtained cured product is good when the content of the component (B) is not more than the upper limit of the above range.
  • Component (C) is a crosslinking agent of the present composition, and has at least two silicon atom-bonded hydrogen atoms in one molecule, and 20 to 70 mol% of all silicon atom-bonded organic groups are phenyl groups. Polysiloxane.
  • the number of silicon-bonded hydrogen atoms in the component is at least two in one molecule, because this is sufficient for crosslinking and the resulting cured product has good hardness.
  • an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group
  • Aryl groups such as phenyl group, tolyl group and xylyl group; monovalent hydrocarbon groups having no aliphatic unsaturated bond such as aralkyl groups such as benzyl group and phenethyl group, and the like, preferably phenyl group, or An alkyl group having 1 to 6 carbon atoms.
  • the component (C) 20 to 70 mol% of the silicon atom-bonded all organic groups are phenyl groups. If the phenyl group content is not less than the lower limit of the above range, the resulting cured product has good mechanical strength at high temperatures, and if it is not more than the upper limit of the above range, This is because the mechanical strength is good.
  • Such component (C) has the general formula: (HR 4 2 SiO) 2 SiR 4 2 Organotrisiloxane represented by the general formula: R 5 3 SiO (R 5 2 SiO) n SiR 5 3 A linear organopolysiloxane represented by the formula: (R 5 SiO 3/2 ) p (R 5 2 SiO 2/2 ) q (R 5 3 SiO 1/2 ) r (SiO 4/2 ) s (R 6 O 1/2 ) t The branched-chain organopolysiloxane represented by these is illustrated. Where R 4 Are the same or different phenyl groups or alkyl groups having 1 to 6 carbon atoms.
  • R 4 examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group. All R 4 Of these, the phenyl group content is in the range of 30 to 70 mol%. Also, in the formula, R 5 Are the same or different hydrogen atoms, phenyl groups, or alkyl groups having 1 to 6 carbon atoms, wherein at least two R 5 Is a hydrogen atom.
  • R 5 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group. All R except for hydrogen atoms 5 Of these, the phenyl group content is in the range of 30 to 70 mol%. Also, in the formula, R 6 Is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 6 Examples of the alkyl group include a methyl group, an ethyl group, a butyl group, a pentyl group, and a hexyl group.
  • n is an integer in the range of 5 to 1,000.
  • p is a positive number
  • q is 0 or a positive number
  • r is 0 or a positive number
  • t is 0 or a positive number
  • q / p is a number in the range of 0 to 10
  • r / p is a number in the range of 0 to 5
  • s / (P + q + r + s) is a number in the range of 0 to 0.3
  • t / (p + q + r + s) is a number in the range of 0 to 0.4.
  • component (C) In such a component (C), all of them have the general formula: (HR 4 2 SiO) 2 SiR 4 2
  • at least 50% by mass of the component (C) is the above organotrisiloxane. Is preferred.
  • other organosiloxanes may be added at appropriate times to adjust the hardness of the resulting cured product.
  • the content of component (C) is such that the silicon-bonded hydrogen atoms in this component are 0.5 to 2 with respect to a total of 1 mol of alkenyl groups in components (A) and (B).
  • the amount is in the range of moles, preferably the amount in the range of 0.5 to 1.5 moles.
  • the component (D) is a hydrosilylation catalyst for promoting the hydrosilylation reaction between the alkenyl group in the components (A) and (B) and the silicon atom-bonded hydrogen atom in the component (C).
  • Examples of component (D) include platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts, and platinum-based catalysts are preferred because they can significantly accelerate the curing of the composition.
  • platinum-based catalyst examples include platinum fine powder, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a platinum-alkenylsiloxane complex, a platinum-olefin complex, and a platinum-carbonyl complex, and in particular, a platinum-alkenylsiloxane complex. It is preferable.
  • alkenylsiloxane examples include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, Examples thereof include alkenyl siloxanes in which part of the methyl groups of these alkenyl siloxanes are substituted with ethyl groups, phenyl groups, and the like, and alkenyl siloxanes in which the vinyl groups of these alkenyl siloxanes are substituted with allyl groups, hexenyl groups, and the like.
  • 1,3-divinyl-1,1,3,3-toteramethyldisiloxane is preferred because the stability of this platinum-alkenylsiloxane complex is good. Further, since the stability of this platinum-alkenylsiloxane complex can be improved, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-diallyl-1,1 can be added to this complex.
  • component (D) is sufficient to promote the hydrosilylation reaction between the alkenyl group in component (A) and component (B) and the silicon-bonded hydrogen atom in component (C).
  • Component (E) is a white pigment for coloring the present composition and its cured product white and increasing the light reflectance.
  • the component (E) examples include metal oxides such as titanium oxide, alumina, zinc oxide, zircon oxide, and magnesium oxide; other examples include barium sulfate and zinc sulfide, and titanium oxide or zinc oxide is particularly preferable.
  • the average particle size and shape of the component (E) are not limited, but the average particle size is preferably in the range of 0.05 to 10.0 ⁇ m, and particularly in the range of 0.1 to 5.0 ⁇ m. Is preferred.
  • the white pigment in order to improve the compatibility and dispersibility with the resin and the inorganic filler, those which have been surface-treated with a silane coupling agent, silica, alumina or the like can be used.
  • the content of the component (E) is 50 parts by mass or more, preferably 60 parts by mass or more with respect to 100 parts by mass in total of the components (A) to (D). This is because the light reflectance of the obtained cured product is good when the content of the component (E) is not less than the above lower limit.
  • Component (F) is spherical silica, non-spherical silica or glass fiber for improving the workability reduction due to the increase in viscosity of the composition, reducing the linear expansion coefficient of the cured product, and improving the dimensional stability. is there.
  • Examples of the spherical silica as the component (F) include dry silica, wet silica, fused silica, and deflagration silica, but fused silica is preferable because the filling property of the present composition is good.
  • Examples of the non-spherical silica of component (F) include quartz powder and glass beads, and quartz powder is preferable.
  • As a glass fiber of a component a chopped glass fiber and a milled glass fiber are illustrated, Preferably it is a milled glass fiber.
  • the particle diameter of the spherical silica as the component (F) is not limited, but the average particle diameter is preferably in the range of 0.1 to 50 ⁇ m, particularly preferably in the range of 0.5 to 20 ⁇ m.
  • the average particle size of the non-spherical silica of the component (F) is not limited, but is preferably in the range of 0.1 to 20 ⁇ m, and particularly preferably in the range of 0.5 to 10 ⁇ m.
  • the shape of the component (F) glass fiber is not limited, but the fiber diameter is preferably in the range of 1 to 50 ⁇ m, particularly preferably in the range of 5 to 20 ⁇ m, and the fiber length is 5 It is preferably in the range of ⁇ 500 ⁇ m, particularly preferably in the range of 10 to 300 ⁇ m.
  • the content of the component (F) is 100 parts by mass or more, preferably 120 parts by mass or more with respect to 100 parts by mass in total of the components (A) to (D). It is because the linear expansion coefficient of the obtained cured product is low and the dimensional stability is good when the content of the component (F) is not less than the above lower limit.
  • the total content of the component (E) and the component (F) is 400 parts by mass or less, preferably 350 parts by mass with respect to a total of 100 parts by mass of the components (A) to (D). Or less. This is because the viscosity of the resulting composition is good when the total content of the component (E) and the component (F) is not more than the above upper limit.
  • Component (G) is a component for increasing the releasability of a cured product from a mold when an optical semiconductor device is produced by transfer molding, injection molding, or compression molding using the present composition.
  • component (G) examples include oleic acid, linoleic acid, linolenic acid, zinc oleate, aluminum oleate, and calcium oleate.
  • Oleic acid and its metal salt are preferred from the viewpoint of little deterioration over time due to oxidation.
  • the content of the component (G) is in the range of 0.01 to 8 parts by mass, particularly 0.05 to 5 parts by mass with respect to 100 parts by mass in total of the components (A) to (D). It is preferable to be within the range.
  • This composition contains (H) an average unit formula as an adhesion promoter for enhancing adhesion to a substrate that is in contact with the curing process: (R 7 3 SiO 1/2 ) f (R 7 2 SiO 2/2 ) g (R 7 SiO 3/2 ) h (SiO 4/2 ) i (R 8 O 1/2 ) j It is preferable to contain the organopolysiloxane represented by these.
  • R 7 Are the same or different, a phenyl group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an organic group containing an epoxy group.
  • R 7 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a heptyl group, a cyclopentyl group, and a cycloheptyl group.
  • R 7 Examples of the alkenyl group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group.
  • R 7 As the epoxy group-containing organic group, 3-glycidoxypropyl group, 4-glycidoxybutyl group, 2- (3,4-epoxycyclohexyl) ethyl group, 3- (3,4-epoxycyclohexyl) propyl group Is exemplified.
  • the phenyl group content is in the range of 15 to 60 mol%, and preferably in the range of 20 to 50 mol%.
  • the phenyl group content is at least the lower limit of the above range, the resulting cured product has good adhesiveness and reflectivity, and when it is below the upper limit of the above range, the resulting cured product is bonded. This is because the properties and heat resistance are good.
  • the alkenyl group content is in the range of 3 to 30 mol%, preferably in the range of 5 to 20 mol%. This is because when the content of the alkenyl group is within the above range, the obtained cured product has good adhesiveness.
  • the content of the epoxy group-containing organic group is in the range of 5 to 30 mol%, preferably in the range of 10 to 20 mol%.
  • the content of the epoxy group-containing organic group is at least the lower limit of the above range, the resulting cured product has good adhesiveness.
  • the content is below the upper limit of the above range, good heat resistance is obtained. Because it is.
  • R 8 Is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • R 8 Examples of the alkyl group include a methyl group, an ethyl group, a butyl group, a pentyl group, and a hexyl group.
  • f is a general formula: R 7 3 SiO 1/2 Is a number satisfying 0 ⁇ f ⁇ 0.5, preferably 0 ⁇ f ⁇ 0.4. This is because the adhesiveness of the obtained hardened
  • g represents a general formula: R 7 2 SiO 2/2 Is a number satisfying 0 ⁇ g ⁇ 0.9, preferably 0 ⁇ g ⁇ 0.8. This is because the adhesiveness of the obtained cured product is good when g is not more than the upper limit of the above range.
  • H is a general formula: R 7 SiO 3/2 Is a number satisfying 0 ⁇ h ⁇ 0.7, preferably 0 ⁇ h ⁇ 0.6. This is because the adhesiveness of the hardened
  • I is a general formula: SiO 4/2 Is a number satisfying 0 ⁇ i ⁇ 0.3, preferably 0 ⁇ i ⁇ 0.2.
  • J is a general formula: R 8 O 1/2 Is a number satisfying 0 ⁇ j ⁇ 0.02. This is because the pot life and storage stability of the composition are good when j is not more than the upper limit of the above range.
  • the sum of f, g, h, and i is 1.
  • the content of the component (H) is an amount that is in the range of 0.5 to 10.0 parts by mass with respect to 100 parts by mass in total of the components (A) to (D). In particular, the amount is preferably in the range of 1.0 to 8.0 parts by mass.
  • the present composition has the purpose of extending the pot life at room temperature without impairing the curability of the composition, and the purpose of increasing the adhesiveness of the sealing material for optical semiconductor devices to the cured product of the composition (I)
  • Organopoly having two or more silicon atom-bonded hydrogen atoms in one molecule and having a phenyl group content of less than 20 mol% with respect to all silicon atom-bonded organic groups. It is preferable to contain siloxane.
  • the number of silicon atom-bonded hydrogen atoms in component (I) is 2 or more in one molecule, because this is sufficient for crosslinking and the resulting cured product has good hardness.
  • the silicon atom-bonded organic group in the component (I) alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc.
  • Aryl groups such as phenyl group, tolyl group and xylyl group; monovalent hydrocarbon groups having no aliphatic unsaturated bond such as aralkyl groups such as benzyl group and phenethyl group, and the like, preferably phenyl group, or An alkyl group having 1 to 6 carbon atoms.
  • the content of the phenyl group with respect to the silicon atom-bonded total organic group in the component (I) is less than 20 mol%, preferably 10 mol% or less.
  • it is preferable that 90 mol% or more of the silicon atom bond total organic group in (I) component is a methyl group.
  • the resulting cured product has good adhesion to various substrates, and the cured product This is because the adhesiveness of the sealing material for the optical semiconductor device is good.
  • (MeHSiO) k (In the formula, Me represents a methyl group, and k is an integer of 4 to 8)
  • Organopolysiloxane represented by the general formula: Me 3 SiO (MeHSiO) x SiMe 3 Me 3 SiO (MeHSiO) y (Me 2 SiO) z SiMe 3 (In the formula, Me represents a methyl group, x is an integer of 5 or more, y and z are each an integer of 5 or more, and y is the same as or more than z)
  • the organopolysiloxane represented by these is illustrated.
  • the content of component (I) is such that the silicon-bonded hydrogen atoms in this component are 0.001 to 0 with respect to 1 mol of the total of alkenyl groups in components (A) and (B).
  • the amount is in the range of 20 moles, preferably in the range of 0.002 to 0.10 moles. This is because when the content of component (I) is within the above range, the pot life at room temperature of the composition is extended, and the adhesiveness of the sealing material for optical semiconductor devices to the obtained cured product becomes good. Furthermore, this is because the flowability of the reactive thermoplastic obtained by hydrosilylation reaction of the composition at a high temperature is improved.
  • This composition is composed of at least the components (A) to (G), but as other optional components, 1-ethynyl-1-cyclohexanol, 2-methyl-3-butyn-2-ol, 3, 5 Alkyne alcohols such as dimethyl-1-hexyn-3-ol and 2-phenyl-3-butyn-2-ol; 3-methyl-3-penten-1-yne, 3,5-dimethyl-3-hexene-1
  • An enyne compound such as yne; 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7 -Reaction inhibitors such as tetrahexenylcyclotetrasiloxane and benzotriazole may be contained.
  • the content of the reaction inhibitor is not limited, but is preferably in the range of 1 to 5,000 ppm by mass with respect to the present composition.
  • the composition may contain an adhesion promoter other than the component (H).
  • adhesion promoters include trialkoxysiloxy groups (for example, trimethoxysiloxy group, triethoxysiloxy group) or trialkoxysilylalkyl groups (for example, trimethoxysilylethyl group, triethoxysilylethyl group), hydrosilyl
  • the composition is improved by improving the handling workability of the composition and adjusting the hardness of the resulting cured product.
  • An organopolysiloxane having 10 or less silicon atoms in which 30 to 60 mol% of all organic groups are alkenyl groups having 2 to 6 carbon atoms may be contained.
  • Examples of the alkenyl group in the organopolysiloxane include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group.
  • the silicon atom-bonded organic group other than the alkenyl group in the organopolysiloxane is not particularly limited, but examples thereof include a methyl group and a phenyl group, and a methyl group is preferable. Further, 30 to 60 mol% of all silicon atom-bonded organic groups are alkenyl groups having 2 to 6 carbon atoms. When the content of the alkenyl group is not less than the lower limit of the above range, the resulting cured product has good hardness. On the other hand, when the content of the alkenyl group is not more than the upper limit of the above range, the resulting cured product has a mechanical strength. It is because it is good.
  • organopolysiloxanes include 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, tetrakis (dimethylvinylsiloxy) silane, methyltris (dimethylvinylsiloxy) silane, And phenyltris (dimethylvinylsiloxy) silane.
  • the content of the organopolysiloxane is preferably an amount within the range of 0 to 50 parts by mass with respect to 100 parts by mass of the component (A).
  • the present composition is a liquid reactive silicone composition.
  • the amount be in the range of 5 to 40 parts by mass.
  • the content of the organopolysiloxane is at least the lower limit of the above range, the viscosity of the composition is good.
  • the content is below the upper limit of the above range, the resulting cured product has good mechanical strength.
  • the present composition includes, as optional components, spherical silica, non-spherical silica, inorganic fillers other than glass fibers, fine organic resin powders such as polymethacrylate resins and silicone resins, as long as the object of the present invention is not impaired.
  • a corrosion inhibitor such as benzotriazole or carboxybenzotriazole, a heat-resistant agent, a flame retardant, and a solvent is not particularly limited, but when obtaining a reactive thermoplastic, it is preferably 10,000 Pa ⁇ s or less, particularly preferably in the range of 10 to 5,000 Pa ⁇ s. Is within.
  • the viscosity is equal to or higher than the lower limit of the above range, it is easy to form a reactive thermoplastic having a desired shape.
  • the viscosity is equal to or lower than the upper limit of the above range, the resulting composition is handled. This is because the property is good.
  • the viscosity at 25 ° C. is preferably in the range of 5 to 200 Pa ⁇ s, more preferably in the range of 5 to 120 Pa ⁇ s. And particularly preferably within the range of 10 to 80 Pa ⁇ s. This is because, when the viscosity is at least the lower limit of the above range, the occurrence of burrs is suppressed during molding, and when the viscosity is below the upper limit of the above range, the workability of the resulting composition is good.
  • the reactive thermoplastic of the present invention will be described in detail.
  • the reactive thermoplastic of the present invention is obtained by reacting until the conversion rate of the hydrosilylation reaction of the reactive silicone cured product becomes 70% to 95%.
  • the conversion rate of hydrosilylation is the percentage of the total functional group that undergoes hydrosilylation reaction, in which the reaction actually takes place, and its confirmation method is not particularly limited. For example, differential scanning calorimetry Using a meter (DSC), the reaction calorific value of the reactive silicone composition and the obtained reactive thermoplastic can be measured, and the conversion rate can be easily calculated from the difference.
  • the reaction proceeds at room temperature or by heating, but heating is preferable in order to obtain a reactive thermoplastic efficiently.
  • the heating temperature is preferably in the range of 50 to 150 ° C, and more preferably in the range of 80 to 130 ° C.
  • the reactive thermoplastic of the present invention is preferably a solid at 25 ° C.
  • the reactive thermoplastic of the present invention preferably has a type D durometer hardness of 30 or more at 25 ° C. as defined in JIS K 7215-1986 “Plastic Durometer Hardness Test Method”.
  • a reactive thermoplastic of the present invention fluidizes once when heated to 100 ° C. or higher, and then undergoes a hydrosilylation reaction to give a cured product.
  • the cured product of the present invention will be described in detail.
  • the cured product of the present invention is obtained by heating the reactive thermoplastic and performing the remaining hydrosilylation reaction, or the liquid reactive silicone composition without passing through the reactive plastic. Is obtained by heating and hydrosilylation reaction, and at 300 ° C., the solid or viscosity is 1,000,000 Pa ⁇ s or more.
  • the hardness of the cured product is not particularly limited, but the type D durometer hardness specified in JIS K 7215-1986 “Plastic Durometer Hardness Test Method” is preferably 60 or more, and more preferably 65 or more. It is preferable that it is 70 or more especially. This is because when the hardness is equal to or higher than the above lower limit, the dimensional stability of the cured product is improved, and the cured product is hardly deformed.
  • cured material is although it does not specifically limit,
  • regulated to JISK7375: 2008 "Plastics-Determination of total light transmittance and total light reflectance” is 75% or more. In particular, it is preferably 80% or more.
  • the linear expansion coefficient of the cured product is not particularly limited, but the linear expansion coefficient measured by the method specified in JIS K 7197-1991 “Test method for linear expansion coefficient by thermomechanical analysis of plastics” is 25 to 200 ° C.
  • the average value in the temperature range is preferably 200 ppm / ° C. or less, and particularly preferably 150 ppm / ° C. or less.
  • the cured product of the present invention is preferably formed by curing the reactive thermoplastic or the reactive silicone composition in a metal mold heated to 100 ° C. or higher.
  • Examples of the curing method for forming the main cured product as the reflecting material of the optical semiconductor device include compression molding, transfer molding, and injection molding.
  • the optical semiconductor device of the present invention will be described in detail.
  • the optical semiconductor device of the present invention is characterized in that the light reflecting material is formed of the cured product.
  • a light emitting diode (LED) is exemplified.
  • the light reflecting material also functions as a frame material (packaging material) of the optical semiconductor device.
  • FIG. 1 shows a cross-sectional view of a surface-mounted LED that is an example of the semiconductor device.
  • an optical semiconductor element 1 is die-bonded on a lead frame 2 by a die bonding material, and the optical semiconductor element 1 and the lead frames 2 and 3 are wire-bonded by bonding wires 4 and 4 ′.
  • a light reflecting material 5 made of the above-described cured product is provided around the optical semiconductor element 1 except for the upper portion thereof, and the optical semiconductor element 1 inside the light reflecting material 5 is sealed with a sealing material 6.
  • the light reflecting material 5 integrated with the lead frames 2 and 3 is formed by transfer molding or compression molding of the reactive thermoplastic of the present invention.
  • Me, Ph, Vi, and Ep represent a methyl group, a phenyl group, a vinyl group, and a 3-glycidoxypropyl group, respectively.
  • the hardness of the reactive thermoplastic and the cured product was measured with a type D durometer specified in JIS K 7215-1986 “Plastic Durometer Hardness Test Method”. Further, the bending strength of the cured product was measured by the method specified in JIS K 6911-1995 “General Test Method for Thermosetting Plastics”.
  • the total light reflectance of the cured product was measured by a method specified in JIS K 7375: 2008 “Plastics—How to obtain total light transmittance and total light reflectance”.
  • the linear expansion coefficient of the cured product is measured by measuring the average linear expansion coefficient in the range of 25 to 200 ° C. according to the method specified in JIS K 7197-1991 “Test method for linear expansion coefficient by thermomechanical analysis of plastics”. did.
  • the mold releasability of this composition is 10 times integral molding with a lead frame using a transfer molding machine at a molding temperature of 120 ° C. and a molding time of 5 minutes. Evaluation was made by confirming the number of molding defects such as peeling from the lead frame.
  • a curable silicone composition, s was prepared. When this composition is heated at 120 ° C. for 10 minutes, it is a solid whose viscosity cannot be measured at 25 ° C., has a type D durometer hardness of 62, and has a viscosity of 4,700 Pa ⁇ s at 100 ° C. I found out that The conversion rate of the hydrosilylation reaction was 79%. When the obtained thermoplastic was heated to 150 ° C., the fluidity was lost after fluidization. The cured product obtained by heating at 150 ° C.
  • the linear expansion coefficient of the cured product was 7% and 108 ppm / ° C. Moreover, in order to manufacture the optical semiconductor device shown in FIG. 1, when the thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, no molding failure was confirmed in the obtained molded product. Good moldings without burrs and voids were obtained.
  • the optical semiconductor device shown in FIG. 1 has a Type D durometer hardness of 86 at 25 ° C., a bending strength of 19 MPa, and a total light reflectance of 94.degree.
  • the linear expansion coefficient of the cured product was 5% and 113 ppm / ° C.
  • the thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, no molding failure was confirmed in the obtained molded product. Good moldings without burrs and voids were obtained.
  • a reactive silicone composition, s was prepared. When this composition is heated at 120 ° C. for 10 minutes, it is a solid whose viscosity cannot be measured at 25 ° C., has a type D durometer hardness of 76, and has a viscosity of 4,600 Pa ⁇ s at 100 ° C. I found out that The conversion rate of the hydrosilylation reaction was 79%. When the obtained thermoplastic was heated to 150 ° C., the fluidity was lost after fluidization. The cured product obtained by heating at 150 ° C. for 1 hour has no fluidity at 300 ° C.
  • the optical semiconductor device shown in FIG. 1 has a type D durometer hardness of 85 at 25 ° C., a bending strength of 20 MPa, and a total light reflectance of 94.
  • the linear expansion coefficient of the cured product was 101 ppm / ° C.
  • the thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, no molding failure was confirmed in the obtained molded product. Good moldings without burrs and voids were obtained.
  • the linear expansion coefficient of the cured product was 5% and 69 ppm / ° C. Moreover, in order to manufacture the optical semiconductor device shown in FIG. 1, when the thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, no molding failure was confirmed in the obtained molded product. Good moldings without burrs and voids were obtained.
  • the cured product obtained by heating at 150 ° C. for 1 hour is a solid whose viscosity cannot be measured at 300 ° C., has a type D durometer hardness of 85 at 25 ° C., a bending strength of 17 MPa, and a total light reflectance.
  • a curable silicone composition that is s was prepared. When this composition is heated at 120 ° C. for 10 minutes, it is a solid whose viscosity cannot be measured at 25 ° C., its type D durometer hardness is 63, and its viscosity at 100 ° C. is 4,900 Pa ⁇ s. I found out that The conversion rate of the hydrosilylation reaction was 76%. When the obtained thermoplastic was heated to 150 ° C., the fluidity was lost after fluidization. The cured product obtained by heating at 150 ° C.
  • the linear expansion coefficient of the cured product was 5% and 104 ppm / ° C.
  • thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, it was confirmed that molding failure occurred in the molded product twice out of 10 times. It was done.
  • thermoplastic When this composition is heated at 120 ° C. for 10 minutes, it is a solid whose viscosity cannot be measured at 25 ° C., has a type D durometer hardness of 71, and has a viscosity of 16,000 Pa ⁇ s at 100 ° C. I found out that The conversion rate of the hydrosilylation reaction was 87%.
  • thermoplastic When the obtained thermoplastic was heated at 150 ° C., the fluidity was lost after fluidization.
  • the cured product obtained by heating at 150 ° C. for 1 hour has no fluidity at 300 ° C. or less, has a Type D durometer hardness of 87 at 25 ° C., a bending strength of 20 MPa, and a total light reflectance of 94.
  • the linear expansion coefficient of the cured product was 117 ppm / ° C. Further, in order to manufacture the optical semiconductor device shown in FIG. 1, when the thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, it was confirmed that there was a molding defect in the molded product 6 times out of 10 times. It was done.
  • thermoplastic was heated to 150 ° C., the fluidity was lost after fluidization.
  • the cured product obtained by heating at 150 ° C. for 1 hour has no fluidity at 300 ° C. or less, has a Type D durometer hardness of 86 at 25 ° C., a bending strength of 20 MPa, and a total light reflectance of 94.
  • the linear expansion coefficient of the cured product was 4 ppm and 98 ppm / ° C.
  • thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, it was confirmed that molding failure occurred in the molded product 5 times out of 10 times. It was done.
  • the linear expansion coefficient of the cured product was 4 ppm and 73 ppm / ° C.
  • thermoplastic body was integrally molded with the lead frame 10 times using a transfer molding machine, it was confirmed that molding failure occurred in the molded product 5 times out of 10 times. It was done.
  • the reactive silicone composition of the present invention can provide a reactive thermoplastic, which is suitable for molding a cured product in a heated mold, and the resulting cured product is In addition, it is suitable as a material for forming a white frame material of a light-emitting diode because it has little decrease in mechanical strength and discoloration due to light and light, has high light reflectance, and excellent mold releasability.

Abstract

La présente invention concerne : une composition de silicium réactive comprenant au moins (A) un organo polysiloxane comprenant un groupe alcényle, (B) un organo polysiloxane comprenant un groupe alcényle, (C) un organo polysiloxane comprenant un atome d'hydrogène lié à un silicium, (D) un catalyseur de réaction d'hydrosilylation, (E) un pigment blanc, (F) de la silice sphérique, de la silice non sphérique, ou de la fibre de verre, et (G) un acide carboxylique ou un sel métallique associé comprenant dix atomes de carbone ou plus et au moins une double-liaison carbone-carbone par molécule ; un thermoplastique réactif associé, un produit durci associé et un dispositif semi-conducteur photoélectrique comprenant le produit durci. La présente invention concerne : une composition de silicium réactive pouvant former un thermoplastique réactif ; un thermoplastique réactif qui se fluidise temporairement une fois chauffé, puis fournit un produit durci ; un produit durci qui présente une faible diminution de la résistance mécanique et une moindre décoloration due à la chaleur et à la lumière, une réflectivité optique élevée, et une excellente capacité d'anti-adhérence au moule ; et un dispositif semi-conducteur photoélectrique qui présente une efficacité lumineuse élevée, une moindre dégradation thermique et une moindre photodégradation d'un matériau réfléchissant la lumière, et une excellente fiabilité.
PCT/JP2014/065831 2013-06-14 2014-06-10 Composition de silicium réactive, thermoplastique réactif, produit durci et dispositif semi-conducteur photoélectrique WO2014200110A1 (fr)

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