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WO2019198755A1 - Composition de résine de silicone - Google Patents

Composition de résine de silicone Download PDF

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Publication number
WO2019198755A1
WO2019198755A1 PCT/JP2019/015615 JP2019015615W WO2019198755A1 WO 2019198755 A1 WO2019198755 A1 WO 2019198755A1 JP 2019015615 W JP2019015615 W JP 2019015615W WO 2019198755 A1 WO2019198755 A1 WO 2019198755A1
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WO
WIPO (PCT)
Prior art keywords
group
formula
hydrocarbon group
silicone resin
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/015615
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English (en)
Japanese (ja)
Inventor
吉仁 武井
大輔 津島
丈章 齋木
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Yokohama Rubber Co Ltd
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Yokohama Rubber Co Ltd
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Filing date
Publication date
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Publication of WO2019198755A1 publication Critical patent/WO2019198755A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to a silicone resin composition.
  • An optical semiconductor device (hereinafter also referred to as an LED) has features such as long life, low power consumption, shock resistance, high-speed response, lightness, thinness, and the like. Development in various fields such as lights, in-vehicle lighting, indoor / outdoor advertising, indoor / outdoor lighting, etc. is making dramatic progress.
  • the LED is manufactured by encapsulating an optical semiconductor element by applying, for example, a silicone resin composition on the optical semiconductor element and curing the composition.
  • the silicone resin composition is used as, for example, a sealing material in addition to the material for sealing the optical semiconductor element.
  • a silicone resin composition for example, in Patent Document 1, (A) 100 parts by weight of an organopolysiloxane represented by the general formula (1) HO (SiR 1 2 O) n H (1) (Wherein R 1 is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and R 1 may be the same or different from each other. N is an integer of 10 or more.
  • an object of this invention is to provide the silicone resin composition excellent in transparency and heat resistance.
  • the present inventors have obtained a desired effect by including a specific amount of an organometallic compound having a predetermined metal with respect to an organopolysiloxane having a silanol group and a condensation catalyst.
  • the present invention was found.
  • the present invention is based on the above knowledge and the like, and specifically, solves the above problems by the following configuration.
  • the organometallic compound is at least one selected from the group consisting of a compound represented by the following formula (2), a compound represented by the formula (3), and a compound represented by the formula (4): [1 ] Or the silicone resin composition as described in [2].
  • M 2 represents the above metal
  • R 2 each independently represents a hydrocarbon group having 1 to 18 carbon atoms
  • m 2 represents the same number as the valence of M 2
  • M 3 represents the above metal
  • R 3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms
  • m3 represents the same number as the valence of M 3 .
  • M 4 represents the above metal, and R 4 represents a hydrocarbon group having 1 to 18 carbon atoms.
  • R 4 represents a hydrocarbon group having 1 to 18 carbon atoms.
  • [5] The silicone resin composition according to [4], wherein the hydrolyzable group is an alkoxysilyl group.
  • the silicone resin composition of the present invention is excellent in transparency and heat resistance.
  • each component can be used alone or in combination of two or more of the substances corresponding to the component.
  • the content of the component means the total content of the two or more types of substances.
  • each component is not particularly limited with respect to its production method. For example, a conventionally well-known thing is mentioned.
  • the silicone resin composition of the present invention (the composition of the present invention) Organopolysiloxane having silanol groups, A condensation catalyst, and An organometallic compound having at least one metal selected from the group consisting of Fe, Mn, Co, Ni, Cu and Ce; A silicone resin composition having a metal content of 0.1 to 200 ppm.
  • the unit “ppm” of the metal content means “mass ppm”.
  • the silicone resin composition generally contains an organopolysiloxane.
  • the organopolysiloxane has a hydrocarbon group bonded to a silicon atom forming the polysiloxane.
  • a high temperature condition for example, about 250 ° C.
  • the hydrocarbon group is oxidized and deteriorated, and the C—H bond in the hydrocarbon group is reduced. It is considered that they dissociate and generate radicals derived from the hydrocarbon group (for example, CH 2 radicals), OH radicals, radicals of silicone resin, and the like.
  • radicals derived from the hydrocarbon group for example, CH 2 radicals
  • OH radicals radicals of silicone resin, and the like.
  • the present inventors estimate that the composition of this invention is excellent in heat resistance. Moreover, in the composition of this invention, when the content of the said organometallic compound is a predetermined range, it is thought that the composition of this invention is excellent in transparency.
  • each component contained in the composition of this invention is explained in full detail.
  • organopolysiloxane contained in the composition of the present invention is a compound having a silanol group, a skeleton of polysiloxane, and a hydrocarbon group bonded to a silicon atom constituting the skeleton.
  • the silanol group possessed by the organopolysiloxane is a group in which a hydroxy group is bonded to a silicon atom. 1 to 3 hydroxy groups can be bonded to the silicon atom. A silanol group is mentioned as a preferred embodiment in which one hydroxy group is bonded to one silicon atom.
  • the group that can be bonded to the silicon atom in the silanol group (excluding the hydroxy group directly bonded to the silicon atom) is not particularly limited. Examples thereof include a hydrocarbon group, a hydrocarbon group —O—, and a hydrogen atom.
  • the hydrocarbon group that can be bonded to the silicon atom in the silanol group is not particularly limited.
  • an aliphatic hydrocarbon group linear, branched or cyclic
  • an aromatic hydrocarbon group or a combination thereof can be used.
  • the hydrocarbon group may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group. Examples of the hydrocarbon group include a methyl group, an ethyl group, and a phenyl group.
  • hydrocarbon group -O- (Hydrocarbon group -O-)
  • the hydrocarbon group in the group represented by the hydrocarbon group —O— that can be bonded to the silicon atom in the silanol group is the same as the hydrocarbon group.
  • the silanol group examples include a silanol group having two hydrocarbon groups such as a dimethylsilanol group.
  • the silanol group may be generated by hydrolysis of a hydrolyzable silyl group.
  • the hydrolyzable silyl group is not particularly limited. Examples thereof include a group in which one group represented by a hydrocarbon group —O— and two hydrocarbon groups are bonded to one silicon atom.
  • the organopolysiloxane skeleton (polysiloxane skeleton) is not particularly limited.
  • the polysiloxane as the skeleton is a polymer having a repeating unit represented by — (Si—O) —.
  • a linear shape, a branched shape, and a network shape can be mentioned.
  • One preferred embodiment of the skeleton is a straight chain. -Linear
  • the skeleton of the organopolysiloxane is linear, the skeleton is preferably a diorganopolysiloxane.
  • the silanol groups are preferably bonded to both ends of the skeleton.
  • the skeleton of the organopolysiloxane is reticulated
  • the skeleton can be a silicone resin.
  • hydrocarbon groups bonded to silicon atoms constituting the skeleton of organopolysiloxane are not particularly limited.
  • the hydrocarbon group similar to the above is mentioned.
  • the organopolysiloxane may be an oligomer.
  • R 5 represents a hydrocarbon group, and R 5 may be the same or different.
  • R 5 is preferably a saturated aliphatic hydrocarbon group, more preferably a methyl group.
  • n is preferably a positive number of 10 or more. n can be a positive number of 1,000 or less. In addition, said n can be made into the value corresponding to the weight average molecular weight of the organopolysiloxane mentioned later.
  • the above-mentioned organopolysiloxane is polydimethylsiloxane- ⁇ , ⁇ -diol (having silanol groups at both ends and two methyl groups bonded to one silicon atom from the viewpoint of being superior in transparency and / or heat resistance.
  • polydialkylsiloxanes having silanol groups at both ends such as linear polysiloxane.
  • the weight average molecular weight of the organopolysiloxane is preferably from 500 to 1,000,000, more preferably from 1,000 to 100,000, from the viewpoint of excellent transparency and / or heat resistance and excellent physical properties of the cured product. More preferably.
  • the weight average molecular weight of the organopolysiloxane is a standard polystyrene equivalent value based on a value measured by gel permeation chromatography (GPC) using chloroform as a solvent.
  • the condensation catalyst contained in the composition of the present invention is not particularly limited as long as it can condense a silanol group.
  • the condensation catalyst can condense silanols.
  • the condensation catalyst is at least one selected from the group consisting of the silanol and a SiH group, a hydrolyzable group, and an R—COO— group (wherein R represents a hydrocarbon group) contained in a silicon compound described later.
  • a group of species can be condensed.
  • the condensation includes a dehydrogenation reaction between a silanol group and a SiH group.
  • one of the preferred embodiments is a compound having zirconium.
  • R 1-1 and R 1-2 each independently represents a hydrocarbon group, and n is 1 to 3. In addition, when n is 2 or 3, several R1-1 may be the same or different. When 4-n is 2 or 3, the plurality of R 1-2 may be the same or different.
  • the hydrocarbon group as R 1-1 or R 1-2 is not particularly limited.
  • the hydrocarbon group include an aliphatic hydrocarbon group (straight, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group.
  • the hydrocarbon group represented by R 1-1 preferably has 3 to 8 carbon atoms.
  • R 1-1 is preferably an aliphatic hydrocarbon group, more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, from the viewpoint of being excellent in transparency and / or heat resistance and excellent in curability.
  • the hydrocarbon group represented by R 1-2 preferably has 3 to 16 carbon atoms, more preferably 4 to 16 carbon atoms.
  • R 1-2 preferably has a cyclic structure.
  • the cyclic structure include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof.
  • the cyclic structure may further have, for example, an aliphatic hydrocarbon group.
  • the cyclic structure is more excellent in transparency and / or heat resistance, and is excellent in curability, from the viewpoint of cyclopropane ring, cyclopentane ring, cyclohexane ring, adamantane ring, naphthene ring (naphtholate as —OOCR 1-2 ).
  • a benzene ring more preferably a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, an adamantane ring, and a naphthene ring.
  • R 1-2 may further have a linear or branched hydrocarbon group in addition to the cyclic structure.
  • a linear or branched hydrocarbon group an aliphatic hydrocarbon group is mentioned, for example.
  • the bond between the cyclic structure and the linear or branched hydrocarbon group is not particularly limited. It is not particularly limited to which carbon atom of R 1-2 the ester bond in the above formula (1) is bonded.
  • n is preferably 2 or 3.
  • the compound represented by the above formula (1) is preferably a zirconium alkoxy ester and more preferably a zirconium trialkoxy monoester from the viewpoint that it is excellent in transparency and / or heat resistance and excellent in curability.
  • zirconium trialkoxy monoesters include: Zirconium tributoxy mononaphthate (zirconium tributoxynaphthenate), Zirconium tributoxy monoisobutyrate, Zirconium tributoxy mono-2-ethylhexanoate, Zirconium tributoxy monocyclopropanecarboxylate, Zirconium tributoxy monocyclopentanecarboxylate, Zirconium tributoxy monocyclohexanecarboxylate, Zirconium tributoxy monoadamantane carboxylate.
  • the content of the condensation catalyst is preferably 0.001 to 1 part by mass with respect to 100 parts by mass of the organopolysiloxane, from the viewpoint of better transparency and / or heat resistance and excellent storage stability. More preferably, the content is 0.01 to 0.5 parts by mass.
  • the organometallic compound contained in the composition of the present invention is a compound having at least one metal selected from the group consisting of Fe, Mn, Co, Ni, Cu and Ce and an organic group. In the present invention, it is considered that the organometallic compound can trap radicals generated from the cured product of the composition of the present invention under high temperature conditions.
  • the organometallic compound has at least one metal selected from the group consisting of Fe, Mn, Co, Ni, Cu, and Ce.
  • the metal is excellent in transparency and / or heat resistance, and is compatible with a silicone resin (the silicone resin contains the organopolysiloxane and a polysiloxane as a silicon compound described later. The same applies to the compatibility). From the viewpoint, Cu, Fe, Mn, and Ce are preferable, and Cu is more preferable.
  • the organic group which the said organometallic compound has is not specifically limited.
  • the organic group include a group derived from an organic carboxylic acid or a phosphate ester; and a ligand such as acetylacetonate (acac).
  • organometallic compound examples include organic carboxylates, phosphates, and complexes.
  • the organic metal compound is preferably an organic carboxylate from the viewpoint of being excellent in transparency and / or heat resistance and excellent in compatibility with a silicone resin.
  • the organometallic compound is superior in transparency and / or heat resistance, and is excellent in compatibility with the silicone resin.
  • the compound represented by the following formula (2), the compound represented by the formula (3), and the formula It is preferably at least one selected from the group consisting of compounds represented by (4).
  • M 2 represents the above metal
  • R 2 each independently represents a hydrocarbon group having 1 to 18 carbon atoms
  • m 2 represents the same number as the valence of M 2 .
  • M 3 represents the above metal
  • R 3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms
  • m3 represents the same number as the valence of M 3 .
  • M 4 represents the above metal, and R 4 represents a hydrocarbon group having 1 to 18 carbon atoms.
  • the valence of M 4 is bivalent.
  • M 2 in the formula (2) is the same as described above.
  • M 3 in Formula (3) and M 4 in Formula (4) can be Fe, Mn, Co, Ni, Cu, or Ce.
  • M 3 in Formula (3) and M 4 in Formula (4) represents the metal as described above.
  • "2" in the right shoulder of the M 2 is located for convenience assigned a number to distinguish the M 2 in the formula (2) and M 3 and M 4 in the formula (4) in the formula (3) It does not represent the valence of the metal.
  • M 3 in formula (3) and M 4 in formula (4) is the same as described above.
  • Examples of the hydrocarbon group having 1 to 18 carbon atoms as R 2 in the formula (2) include an aliphatic hydrocarbon group (linear, branched or cyclic), an aromatic hydrocarbon group, or a combination thereof. Is mentioned.
  • the carbon number is preferably from 1 to 18, and more preferably from 7 to 10, from the viewpoints of excellent transparency and / or heat resistance and excellent compatibility with the silicone resin.
  • the hydrocarbon group having 1 to 18 carbon atoms is preferably an aliphatic hydrocarbon group, and more preferably a saturated aliphatic hydrocarbon group, from the viewpoints of excellent transparency and / or heat resistance and excellent curability.
  • Specific examples of the hydrocarbon group having 1 to 18 carbon atoms include a residue obtained by removing a carboxy group from octanoic acid (C7) and a residue obtained by removing a carboxy group from neodecanoic acid (C9).
  • R 3 in formula (3), R 4 in formula (4) is the same as R 2 in formula (2).
  • m3 M2 in Formula (2) represents the same number as the valence of M 2.
  • m2 represents the same number as the valence of M 2
  • M2 represents the same number (2) as the valence (divalent) of M 2
  • m2 is 2.
  • M3 in formula (3) is the same as m2.
  • the compound represented by the said Formula (2) from the viewpoint that the said organometallic compound is excellent by transparency and / or heat resistance is preferable.
  • the compound represented by the formula (2) include a salt of the above metal of 2-ethylhexanoic acid and a salt of the above metal of neodecanoic acid.
  • the compound represented by the above formula (2) is preferably a salt of the above metal of 2-ethylhexanoic acid or neodecanoic acid, from the viewpoint of being excellent in transparency and / or heat resistance, Mn salt of 2-ethylhexanoic acid, Co salt, Cu salt or Ce salt, or neodecanoic acid Cu salt or Ce salt is more preferable, and 2-ethylhexanoic acid Ce salt or Cu salt is more preferable.
  • the content of the metal contained in the organometallic compound is 0.1 to 200 ppm with respect to the composition of the present invention.
  • content of the said metal is mass conversion. In this invention, when content of the said metal is the said range, it is excellent in transparency and heat resistance.
  • the metal content is superior in transparency and / or heat resistance, excellent in heat-resistant yellowing (the property of the resulting cured product does not change to yellow or hardly changes in color under high temperature conditions), and balance between transparency and heat resistance. From the viewpoint of superiority, it is preferably 0.1 to 100 ppm, more preferably 5 to 50 ppm, and even more preferably more than 30 ppm and 50 ppm or less with respect to the composition of the present invention.
  • the composition of the present invention is further selected from the group consisting of a SiH group, a hydrolyzable group, and an R—COO— group (wherein R represents a hydrocarbon group) from the viewpoint of being excellent in transparency and / or heat resistance. It is preferable to contain a silicon compound having at least one selected substituent.
  • the silicon compound has a silicon atom.
  • the silicon compound may have one or more silicon per molecule.
  • the silicon compound does not contain the organopolysiloxane.
  • the silicon compound has at least one substituent selected from the group consisting of a SiH group, a hydrolyzable group, and an R—COO— group (wherein R represents a hydrocarbon group).
  • the substituent is preferably a SiH group or a hydrolyzable group from the viewpoint that it is excellent in transparency and / or heat resistance and excellent in storage stability.
  • the SiH group is a group represented by —Si—H.
  • the group capable of bonding to a silicon atom in —Si—H (a group other than the above H) is not particularly limited.
  • Examples of the group capable of bonding to the silicon atom in —Si—H include a group capable of bonding to the silicon atom in the silanol group.
  • a hydrocarbon group is mentioned as one of preferred embodiments. In addition, it is mentioned as one of the preferable aspects that the said hydrocarbon group does not have an unsaturated bond.
  • the hydrolyzable group is preferably a hydrolyzable silyl group, more preferably an alkoxysilyl group, from the viewpoint that it is excellent in transparency and / or heat resistance and excellent in storage stability.
  • the alkoxysilyl group is a group in which 1 to 3 alkoxy groups are bonded to a silicon atom. In the alkoxysilyl group, 2 to 3 alkoxy groups can be bonded to the silicon atom.
  • the alkoxy group is not particularly limited. For example, a methoxy group, an ethoxy group, and a propoxy group are mentioned.
  • the organic group that can bond to the silicon atom is not particularly limited.
  • an alkyl group such as a methyl group
  • a hydrocarbon group such as an aromatic hydrocarbon group.
  • R-COO- group In the R-COO- group, the above R represents a hydrocarbon group.
  • the hydrocarbon group as R is not particularly limited.
  • the R—COO— group can be bonded to the silicon atom of the silicon compound directly or through an organic group.
  • the organic group is not particularly limited.
  • the above-mentioned SiH group, hydrolyzable silyl group, and R—COO— group bonded to a silicon atom can further have another functional group to constitute a silane coupling agent.
  • another functional group an amino group and a hydroxy group are mentioned, for example.
  • the SiH group, hydrolyzable silyl group, or R—COO— group bonded to a silicon atom and the other functional group can be bonded directly or via an organic group.
  • Silane compound A silicon compound having one silicon per molecule may be hereinafter referred to as a silane compound.
  • the silane compound include tetraalkoxysilanes such as tetramethoxysilane, alkyltrialkoxysilanes such as methyltrimethoxysilane, and silane coupling agents having the above substituents.
  • the said silicon compound is polysiloxane.
  • the polysiloxane include organopolysiloxane.
  • the organopolysiloxane may be linear, branched, or network.
  • the polysiloxane may have one or a plurality of the substituents in one molecule.
  • polysiloxane examples include a hydrolysis condensate of the silane compound (hydrolysis condensation may be partial) and an organopolysiloxane having the substituent.
  • the hydrolysis condensate of the silane compound is preferably an alkyltrialkoxysilane hydrolysis condensate such as methyltrimethoxysilane.
  • Examples of the hydrolysis condensate include hydrolysis condensates of 3 to 10 alkyltrialkoxysilanes.
  • the organopolysiloxane having a substituent is preferably a hydrolyzable silyl group, and more preferably a linear polydialkylsiloxane having a trialkoxysilyl group at both ends.
  • the content of the silicon compound is from 1 to 1,000 parts by mass with respect to 100 parts by mass of the organopolysiloxane from the viewpoint of being excellent in transparency and / or heat resistance and excellent in curability. It is preferably 5 to 500 parts by mass, more preferably 10 to 500 parts by mass.
  • the composition of this invention can contain an additive further as needed in the range which does not impair the objective and effect of this invention other than said component.
  • the additive include a compound containing silicon other than the organopolysiloxane and the silicon compound (for example, a compound having a vinyl group and a silicon atom), a catalyst other than the condensation catalyst (for example, a hydrosilylation catalyst), and packing.
  • the content of the additive is not particularly limited.
  • composition of the present invention is not particularly limited with respect to its production method.
  • it can be produced by mixing the organopolysiloxane, the condensation catalyst, the organometallic compound, and the silicon compound and additives that can be used as necessary.
  • composition of the present invention can be cured, for example, under conditions of 100 to 200 ° C.
  • adherends to which the composition of the present invention can be applied include metals, glass, plastics, rubbers, and semiconductors (for example, optical semiconductor elements).
  • the composition of the present invention can be used, for example, as a semiconductor sealant.
  • the composition of this invention is mentioned as one of the aspects with preferable using for sealing a semiconductor.
  • the semiconductor to which the composition of the present invention can be applied is not particularly limited. For example, a conventionally well-known thing is mentioned.
  • each component of the following Table 1 was used in the composition (part by mass) shown in the same table, and these were mixed with a stirrer to produce a composition.
  • the value described in the column of each organometallic compound is the metal content (unit: ppm) of each organometallic compound relative to the total mass of the silicone resin composition.
  • Sample preparation> Initial sample Each composition manufactured as mentioned above was hardened on 150 degreeC conditions for 5 hours, and the initial sample (thickness 2mm) was obtained. Sample after heat test A heat test was performed by placing each of the initial samples prepared as described above at 250 ° C. for 48 hours to obtain a sample after the heat test.
  • Hardness increase rate (%) [(BA) / A] ⁇ 100 A: Initial hardness B: Hardness after heat test
  • the heat resistance is excellent.
  • Table 1 shows the initial hardness and the hardness after the heat resistance test.
  • the sample after the heat test breaks and the hardness cannot be measured, it is evaluated that the heat resistance is inferior, and this is indicated as “x” in the hardness column after the heat test. Is displayed.
  • the sample after the heat test is destroyed, it is considered that the sample contains at least a large amount of radicals derived from the organopolysiloxane having a silanol group.
  • the hardness can be measured, and the lower the increase rate of the hardness, the better the heat resistance.
  • the transmittance (%) at a wavelength of 450 nm was measured using an ultraviolet / visible absorption spectrum measuring apparatus (manufactured by Shimadzu Corporation) according to JIS K0115: 2004. It was measured. The higher the transmittance, the better the transmittance of light having the specific wavelength (the emission color is blue).
  • KC-89S Product name KC-89S manufactured by Shin-Etsu Chemical Co., Ltd. Condensate of 3 to 5 methyltrimethoxysilane. Methoxy group 45% by mass. Viscosity 5mPa ⁇ s TMS-ss70: 10 parts by mass of tetramethoxysilane and 100 parts by mass of acetic acid with respect to 100 parts by mass of polydimethylsiloxane having a silanol group at both ends (weight average molecular weight 28,000, trade name ss70, manufactured by Shin-Etsu Chemical Co., Ltd.) 0.1 part by mass was added, and these were reacted under conditions of 100 ° C.
  • TMS-ss70 The weight average molecular weight of TMS-ss70 was 35,000.
  • the main structure of TMS-ss70 is shown by the following formula. N in the formula can be a value corresponding to the weight average molecular weight.
  • Tributoxynaphthenic acid Zr Tributoxynaphthenic acid Zr was produced as follows. Zirconium tetrabutoxide (manufactured by Kanto Chemical Co., Ltd., 0.026 mol) and naphthenic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) Hydrocarbon group having a carboxy group and a cyclic structure (cyclopentane ring) (the average number of carbon atoms of the hydrocarbon group is 15) ), And a neutralization value of 220 mg.) 6.6 g (0.026 mol) was stirred and reacted at room temperature for about 2 hours in a nitrogen atmosphere to obtain a target compound.
  • the neutralization value of naphthenic acid is the amount of KOH required to neutralize 1 g of naphthenic acid.
  • the obtained compound was analyzed using a Fourier transform infrared spectrophotometer (FT-IR), and it was confirmed that the compound was tributoxynaphthenic acid Zr.
  • FT-IR Fourier transform infrared spectrophotometer
  • the average number of carbons derived from naphthenic acid in the tributoxynaphthenic acid Zr is 15.
  • Neodecanoic acid Cu manufactured by Nippon Chemical Industry Co., Ltd.
  • Cu (OC ( O) C 10 H 19 ) 2 -2-ethylhexanoic acid
  • Cu manufactured by Nippon Chemical Industry Co., Ltd.
  • Cu [OC ( O) CH (C 2 H 5) C 4 H 9] 2
  • Ni compound Ni complex, Ni (acac) 3 manufactured by Gelest Co.
  • Cu compound Cu complex, Cu (acac) 3 manufactured by Gelest
  • Comparative Example 1 not containing a predetermined organometallic compound had poor heat resistance.
  • Comparative Examples 2, 4 to 8 in which the content of the predetermined organometallic compound was less than the predetermined range, the heat resistance was poor.
  • Comparative Example 3 in which the content of the predetermined organometallic compound is larger than the predetermined range has poor transparency.
  • composition of the present invention was excellent in transparency and heat resistance.

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  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

La présente invention concerne une composition de résine de silicone présentant d'excellentes qualités de transparence et de résistance à la chaleur. Cette composition de résine de silicone contient : un organopolysiloxane ayant un groupe silanol, un catalyseur de condensation, et un composé organométallique ayant au moins un métal choisi dans le groupe constitué par Fe, Mn, Co, Ni, Cu et Ce. La teneur en métal est comprise entre 0,1 et 200 ppm.
PCT/JP2019/015615 2018-04-13 2019-04-10 Composition de résine de silicone Ceased WO2019198755A1 (fr)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012066998A1 (fr) * 2010-11-18 2012-05-24 横浜ゴム株式会社 Composition de résine de silicone de type thermodurcissable, structure contenant une résine de silicone, corps d'étanchéité pour élément semi-conducteur optique, et catalyseur de condensation de silanol

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012066998A1 (fr) * 2010-11-18 2012-05-24 横浜ゴム株式会社 Composition de résine de silicone de type thermodurcissable, structure contenant une résine de silicone, corps d'étanchéité pour élément semi-conducteur optique, et catalyseur de condensation de silanol

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