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WO2019163686A1 - Composé silicium organique liquide, et composition de résine thermodurcissable à laquelle celui-ci est mélangé - Google Patents

Composé silicium organique liquide, et composition de résine thermodurcissable à laquelle celui-ci est mélangé Download PDF

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Publication number
WO2019163686A1
WO2019163686A1 PCT/JP2019/005719 JP2019005719W WO2019163686A1 WO 2019163686 A1 WO2019163686 A1 WO 2019163686A1 JP 2019005719 W JP2019005719 W JP 2019005719W WO 2019163686 A1 WO2019163686 A1 WO 2019163686A1
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Prior art keywords
resin composition
thermosetting resin
group
general formula
hydrocarbon group
Prior art date
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Ceased
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PCT/JP2019/005719
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English (en)
Japanese (ja)
Inventor
健太郎 石川
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JNC Corp
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JNC Corp
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Publication date
Application filed by JNC Corp filed Critical JNC Corp
Priority to CN201980013920.8A priority Critical patent/CN111788254A/zh
Priority to KR1020207023742A priority patent/KR20200123123A/ko
Publication of WO2019163686A1 publication Critical patent/WO2019163686A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • 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
    • H10W74/10—
    • H10W74/40—
    • H10W74/476—

Definitions

  • the present invention relates to a liquid organosilicon compound, a thermosetting composition useful for applications such as an optical material and an electrical insulating material containing the compound, a cured product obtained by thermosetting this, and a semiconductor resin using the same It relates to a sealing material.
  • White LEDs have been used for lighting and other purposes, but heat generation of the LED package has become a problem as the output increases.
  • a silicone resin has been used as a sealing material for white LEDs instead of an epoxy resin.
  • Silicone resins used for LEDs are roughly classified into two types, phenyl silicone resins and methyl silicone resins.
  • phenyl silicone resin has a high refractive index and good light extraction efficiency. Furthermore, since it has a high gas barrier property and good adhesion to the package, it has excellent reliability such as moisture absorption reflow resistance or heat cycle resistance. However, the heat-resistant yellowing is superior to the epoxy resin, and is not sufficient to cope with the large output of the LED.
  • Methyl silicone resin is very excellent in heat-resistant yellowing, but the light extraction efficiency of the LED is not good because of its low refractive index.
  • the methyl silicone resin is mainly composed of dimethyl silicone, the gas barrier property is low, the adhesion with the package is inferior, and there is a problem that the methyl silicone resin is easily peeled off during moisture absorption reflow. When peeling occurs, the luminance of light generated from the LED is lowered, which is not preferable.
  • the commonly used phenyl silicone resin is not only severely deteriorated in luminance due to yellowing but also cracks due to resin deterioration.
  • the dimethyl silicone resin has little luminance deterioration due to yellowing, the deterioration and shrinkage of the resin progresses in the high temperature region, cracks are generated, and the luminance deteriorates.
  • Patent Document 1 discloses a sealing material for LED using a thermosetting resin composition of a thermosetting resin having a SiH group introduced into a cage-type octasilsesquioxane and an organopolysiloxane having an alkenyl group. .
  • Patent Document 2 discloses a thermosetting resin composition using an incomplete cage type silsesquioxane called a so-called double decker type.
  • the silsesquioxane is a structure-controlled compound obtained by hydrolytic condensation of phenyltrimethoxysilane, and the position of the Si-Ph group is not random but the structure is controlled, so that it has a high refractive index but is heat resistant. Excellent light resistance.
  • Patent Document 2 discloses a thermosetting containing a SiH group and a vinyl group obtained by reacting a silanol group part of silsesquioxane having an incomplete cage structure with a SiH group-modified compound and an organopolysiloxane having an alkenyl group.
  • a hardened resin is disclosed, which has a high refractive index and high heat resistance, and also has good adhesion to a polyphthalamide resin base material or silver base material that is the LED package material It is shown.
  • Patent Document 1 only a heat resistance test at 200 ° C. for 168 hours is performed, and in Patent Document 2, only a heat resistance test at 180 ° C. for 1000 hours is performed.
  • Patent Document 2 describes long-term reliability in a high temperature region of 200 to 250 ° C. or higher, which is emitted from a high-power LED.
  • An object of the present invention is to provide a thermosetting composition capable of obtaining a cured product having a high refractive index, transparency and heat resistance, and is contained in the thermosetting composition.
  • An object is to provide a sealing material for a liquid organosilicon compound to be produced, a cured product obtained from a thermosetting composition, a molded body, and a light emitting diode.
  • the present inventor has intensively studied to solve the above problems. As a result, it succeeded in the synthesis of a liquid organosilicon compound containing a double-decker silicon compound structure and not requiring a solvent because it is not solid, and further comprising a thermosetting composition containing the compound and a curing agent. The cured product was found to be excellent in transparency, heat resistance and the like, and the present invention was completed.
  • a liquid organosilicon compound represented by the following general formula (1) represented by the following general formula (1).
  • R 1 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • R 2 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • Each n is independently an integer of 1 to 50.
  • each R 3 independently represents an unsaturated hydrocarbon group having one double bond having 2 to 5 carbon atoms.
  • each R 21 is independently an unsaturated hydrocarbon group having one double bond having 2 to 5 carbon atoms.
  • R 22 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • n is an integer of 0 to 50.
  • a resin sealing material for a semiconductor comprising the thermosetting resin composition according to any one of [3] to [6].
  • the cured product of the thermosetting resin composition of the present invention is excellent in, for example, high refractive index, transparency, heat resistance, heat yellowing resistance and the like. Therefore, the molded body containing the cured product can be suitably used for applications such as a semiconductor sealing material, an optical semiconductor sealing material, an optical semiconductor die-bonding material, an insulating film, a sealing agent, and an optical lens.
  • transparent materials, optical materials, optical films, optical sheets, adhesives, electronic materials, insulating materials, interlayer insulating films, paints, inks, coating materials, molding materials, potting materials, liquid crystal sealants, display device sealants, Solar cell sealing material, resist material, color filter, electronic paper material, hologram material, solar cell material, fuel cell material, display material, recording material, waterproof material, moisture proof material, battery solid electrolyte, gas separation can be used for membranes. Moreover, it can use for the additive etc. to other resin.
  • liquid organosilicon compound of the present invention is represented by the following general formula (1).
  • R 1 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • R 2 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • Each n is independently an integer of 1 to 50.
  • each R 3 independently represents an unsaturated hydrocarbon group having one double bond having 2 to 5 carbon atoms.
  • Preferred hydrocarbon groups as R 1 are each independently a group selected from an alkyl group having 1 to 4 carbon atoms, and alicyclic groups are each independently a group selected from a cyclopentyl group and a cyclohexyl group.
  • the group hydrocarbon group is a group independently selected from a phenyl group and a naphthyl group. When R 1 is a phenyl group, the heat resistance is excellent, and when it is a methyl group, the fluidity is excellent.
  • Preferred hydrocarbon groups as R 2 are each independently a group selected from alkyl groups having 1 to 4 carbon atoms, and alicyclic groups are each independently a group selected from a cyclopentyl group and a cyclohexyl group.
  • the group hydrocarbon group is a phenyl group.
  • R 2 is a methyl group, the heat resistance is excellent, and when R 2 is a phenyl group, the gas barrier property is excellent.
  • Each n is independently an integer of 1 to 50.
  • Preferred n is 1 to 30, and more preferred n is 3 to 23. If it is this range, compatibility with another polymeric silicon compound is enough, and hardened
  • Specific examples of the unsaturated hydrocarbon group preferable as R 3 include a vinyl group.
  • liquid organosilicon compound represented by the general formula (1) of the present invention is an equilibration reaction between a compound represented by the following general formula (2-1) and a compound represented by the following general formula (2-2). It is manufactured from the process to make.
  • each R 21 is independently an unsaturated hydrocarbon group having one double bond having 2 to 5 carbon atoms.
  • Specific examples of the unsaturated hydrocarbon group preferable as R 21 include a vinyl group.
  • R 22 is a group independently selected from a hydrocarbon group having 1 to 8 carbon atoms, an alicyclic group, or an aromatic hydrocarbon group.
  • Preferred hydrocarbon groups for R 22 are each independently a group selected from alkyl groups having 1 to 4 carbon atoms, and the alicyclic groups are each independently a group selected from a cyclopentyl group and a cyclohexyl group.
  • the group hydrocarbon group is a phenyl group.
  • n is an integer of 0 to 50. Preferred n is 1 to 35, and more preferred n is 5 to 25. Within this range, the reactivity is sufficient and the reaction solution does not become a gel.
  • the compound represented by the general formula (1) can be obtained by an equilibration reaction between the compound represented by the general formula (2-1) and the compound represented by the general formula (2-2).
  • the reaction solvent may be any solvent as long as it does not condense with the compound. Examples of such solvents include hydrocarbon solvents such as hexane and heptane, aromatic hydrocarbon solvents such as benzene, toluene and xylene, diethyl ether, tetrahydrofuran (THF), dioxane and cyclopentyl methyl ether.
  • Examples include ether solvents, halogenated hydrocarbon solvents such as methylene chloride and chloroform, ester solvents such as ethyl acetate, and lactam solvents such as N-methyl-2-pyrrolidone (NMP).
  • the solvent may be a single solvent or two or more solvents. Of these, toluene is more preferred.
  • the reaction temperature is usually 40 to 150 ° C, preferably 110 to 120 ° C.
  • a strong acid or a strong base is usually used. In the method for producing a liquid organosilicon compound in the present invention, a strong acid is preferable as the catalyst in consideration of the stability of the reaction of silsesquioxane.
  • Such a catalyst examples include hydrochloric acid, sulfuric acid, fluorosulfuric acid, trifluoromethanesulfonic acid, activated clay, and sulfonic acid ion exchange resin. Of these, sulfonic acid ion exchange resins are more preferred.
  • thermosetting resin composition of the present invention > 3-1. 1st component
  • the thermosetting resin composition of this invention contains the liquid organosilicon compound represented by General formula (1) as a 1st component.
  • the liquid organosilicon compound represented by the general formula (1) has heat resistance, and improves the heat resistance of the thermosetting resin composition.
  • the content of the liquid organosilicon compound represented by the general formula (1) is preferably 1 to 99% by mass, more preferably 20 to 80% by mass with respect to the total amount of the thermosetting resin composition. If it is this range, compatibility with another component will be enough and the cloudiness of hardened
  • thermosetting resin composition of this invention contains the liquid organosilicon compound represented by following Structural formula (4) as a 2nd component.
  • the content of the liquid organosilicon compound represented by the structural formula (4) is preferably 1 to 99% by mass and more preferably 20 to 80% by mass with respect to the total amount of the thermosetting resin composition. If it is this range, the reactivity of a thermosetting resin composition is enough, and it can suppress that hardened
  • thermosetting resin composition of this invention contains a curing catalyst as other components as needed.
  • the curing catalyst is not particularly limited as long as it is a transition metal catalyst usually used as a reaction catalyst, but a platinum catalyst is preferably used.
  • a platinum catalyst is preferably used as an example of the platinum catalyst.
  • a normal hydrosilylation catalyst can be selected.
  • preferred hydrosilylation catalysts are Karstedt catalyst, Speyer catalyst, hexachloroplatinic acid and the like, which are generally well-known platinum catalysts.
  • the use amount of the curing catalyst is preferably 0.1 mass ppm to 10 mass ppm in terms of mass ratio of the transition metal contained in the catalyst to the thermosetting resin composition. If the addition ratio is in the above range, curing failure is unlikely to occur, the pot life after preparation of the thermosetting resin composition is too short, and there is no risk of inconvenience that it cannot be used, and coloring of the cured product does not occur. . A more preferable addition ratio is 0.5 mass ppm to 4 mass ppm.
  • thermosetting resin composition of this invention contains a metal oxide as another component as needed. When the metal oxide is contained, the light scattering property is improved.
  • Preferred metal oxides include silicon oxide, titanium oxide, zinc oxide and the like.
  • the content of the metal oxide is preferably 1 to 90% by mass and more preferably 5 to 85% by mass with respect to the total amount of the thermosetting resin composition. Within this range, the thermosetting resin composition has sufficient light diffusibility and light reflectivity for use as a light diffusing material or light reflecting material, and moldability is not lost.
  • a metal oxide may use only 1 type or may use 2 or more types together.
  • thermosetting resin composition of the present invention contains a phosphor as another component, if necessary.
  • a phosphor as another component, if necessary.
  • Preferred phosphors include, for example, yttrium aluminum garnet, silicon aluminum oxynitride, silicon aluminum oxynitride, ruthenium aluminum garnet, and the like.
  • the content of the phosphor is preferably 1 to 90% by mass and more preferably 5 to 85% by mass with respect to the total amount of the thermosetting resin composition. If it is this range, the wavelength conversion property of a thermosetting resin composition is enough, and a moldability is not lost. Only 1 type of fluorescent substance may be used or 2 or more types may be used together.
  • thermosetting resin composition of the present invention was identified by the following analysis method. ⁇ Measurement of number average molecular weight and weight average molecular weight> The number average molecular weight and the weight average molecular weight of the polymer synthesized in the present invention were measured as follows. Using a high-performance liquid chromatograph system CO-2065plus manufactured by JASCO Corporation, 20 ⁇ L of a THF solution with a sample concentration of 1 wt% is used as an analysis sample. Temperature: 40 ° C., detector: RI, eluent: THF, and eluent flow rate: 1.0 mL / min, measured by GPC method and determined by polystyrene conversion.
  • ⁇ NMR (nuclear magnetic resonance spectrum)> A 400 MHZ NMR produced by JEOL Ltd. was used, and the measurement sample was dissolved in heavy acetone (Wako Pure Chemical Industries, Ltd.) and measured. The average silicone chain length introduced was determined from the integral ratio of 1 H-NMR.
  • Divinyl polysiloxane 1 polydimethylsiloxane having a number average molecular weight of 700 having vinyl groups at both ends corresponding to the formula (2-2)]: manufactured by JNC Corporation
  • Divinyl polysiloxane 2 (corresponding to formula (2-2), polydimethylsiloxane having a vinyl group at both ends and a number average molecular weight of 2100): manufactured by JNC Corporation
  • MVS-H curing retarder, substance name, 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane
  • JNC Corporation platinum catalyst: Pt-VTSC-3.
  • 0X (1,3-divinyl-1,1,3,3 tetramethyldisiloxane platinum (0) complex xylene solution, platinum content: 3.0 wt%) manufactured by Umicore Japan Ltd.
  • the solvent used in the reaction is not particularly limited as long as it does not inhibit the progress of the reaction.
  • Aromatic hydrocarbon solvents such as benzene, toluene, xylene, ether solvents such as tetrahydrofuran (THF), cyclomethylpentyl ether, dioxane, hydrocarbon solvents such as hexane and heptane, alcohols such as methanol, ethanol, and isopropanol It is a solvent.
  • Aromatic hydrocarbon solvents such as benzene, toluene, xylene, ether solvents such as tetrahydrofuran (THF), cyclomethylpentyl ether, dioxane, hydrocarbon solvents such as hexane and heptane, alcohols such as methanol, ethanol, and isopropanol It is a solvent.
  • THF tetrahydrofuran
  • cyclomethylpentyl ether di
  • thermosetting resin composition ⁇ Preparation of thermosetting resin composition>
  • the compound or divinylpolysiloxane 1 synthesized in the above example and the organopolysiloxane represented by the following structural formula (4) were placed in a screw tube bottle.
  • the screw tube bottle was set in a rotating / revolving mixer ["Awatori Nertaro (registered trademark) ARE-250" manufactured by Sinky Co., Ltd.] and mixed and defoamed.
  • thermosetting resin composition a thermosetting resin composition
  • concentration of the curing retarder 10 ppm by mass and the concentration of the platinum catalyst is 1 ppm by mass
  • a to d and comparative cured products a to b were obtained.
  • Table 1 shows the blending amount (parts by mass) of each thermosetting resin composition.
  • thermosetting resin composition is sandwiched between 2 sheets of glass with Naflon SP packing (4 mm diameter) manufactured by Nichias Co., Ltd., and the thermosetting resin composition is poured into this, and the thermosetting resin composition is poured at 80 ° C. for 1 hour, and then 150 Curing was carried out by heating in order at 4 ° C. for 4 hours, and the glass was peeled off to obtain cured products a to d and comparative cured products a to b having a smooth surface of 30 mm ⁇ 35 mm ⁇ 4 mm thickness.
  • the sample was divided into two and 30 mm ⁇ 20 mm ⁇ 4 mm was used as a transmittance measurement sample. 30 mm ⁇ 10 mm ⁇ 4 mm was used as a sample for refractive index measurement.
  • ⁇ Transmittance measurement> The light transmittance at a wavelength of 450 nm was measured at one place in the center of the cured product using an ultraviolet-visible spectrophotometer V-650 manufactured by JASCO Corporation.
  • a test piece (30 mm ⁇ 10 mm ⁇ 4 mm) was prepared according to JIS K7142 (2014). Using this test piece, the refractive index of one part of the test piece was measured using an Abbe refractometer (NAR-2T manufactured by Atago Co., Ltd.) using a D line (586 nm) of a sodium lamp. As the intermediate solution, 1-bromonaphthalene (manufactured by Wako Pure Chemical Industries, Ltd.) was used.
  • the heat resistance test was carried out and evaluated by the following method that was stricter than in the past (for example, in prior art document 1, heating at 200 ° C. for 168 hours).
  • the above-mentioned cured product having a thickness of 4 mm was placed in an oven (clean oven: DE410 manufactured by Yamato Scientific Co., Ltd.) at 250 ° C. and heat-treated for 1000 hours.
  • the light transmittance of the cured product after the test was measured with a UV-visible spectrophotometer, and from the transmittance at a wavelength of 450 nm, the retention at this wavelength (%) (the transmittance after heat treatment at 250 ° C. for 1000 hours) / Initial transmittance ⁇ 100) was calculated, and then heat-resistant transparency (retention rate of each cured product / retention rate of comparative cured product a) was calculated and evaluated.
  • the “initial transmittance” is the transmittance before the heat treatment.
  • the thickness of the center of the cured product after the test was measured with a digital thickness gauge, and the dimensional retention (%) (thickness after heat treatment at 250 ° C. for 1000 hours / initial thickness ⁇ 100) was calculated. Thereafter, heat-resistant dimensional stability (size retention of each cured product / size retention of comparative cured product a) was calculated and evaluated.
  • the “initial thickness” is the thickness before the heat treatment.
  • the organosilicon compound of the present invention and the thermosetting resin composition containing the same can be used for sealing materials for optical semiconductors such as LEDs, insulating films, sealing agents, adhesives, optical lenses, and the like.

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Abstract

L'invention a pour objet de fournir une composition thermodurcissable qui présente un indice de réfraction élevé, et qui permet d'obtenir un objet durci de transparence et de résistance à la chaleur satisfaisantes. Plus précisément, l'invention concerne un composé silicium organique liquide ainsi que son procédé de fabrication, et une composition de résine thermodurcissable comprenant ledit composé silicium organique liquide.
PCT/JP2019/005719 2018-02-20 2019-02-15 Composé silicium organique liquide, et composition de résine thermodurcissable à laquelle celui-ci est mélangé Ceased WO2019163686A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201980013920.8A CN111788254A (zh) 2018-02-20 2019-02-15 液状有机硅化合物及掺合所述化合物的热硬化性树脂组合物
KR1020207023742A KR20200123123A (ko) 2018-02-20 2019-02-15 액상 유기 규소 화합물 및 그것을 배합한 열 경화성 수지 조성물

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JP2018027674A JP2019143026A (ja) 2018-02-20 2018-02-20 液状有機ケイ素化合物、およびそれを配合した熱硬化性樹脂組成物
JP2018-027674 2018-02-20

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JP2019143026A (ja) * 2018-02-20 2019-08-29 Jnc株式会社 液状有機ケイ素化合物、およびそれを配合した熱硬化性樹脂組成物
WO2020116198A1 (fr) * 2018-12-04 2020-06-11 Jnc株式会社 Composé d'organosilicium, procédé de production d'un composé d'organosilicium, composition de résine thermodurcissable, corps moulé et dispositif optique semiconducteur
US20230295427A1 (en) * 2020-08-06 2023-09-21 Jnc Corporation Siloxane polymer, siloxane polymer composition, and molded article

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WO2022215759A2 (fr) * 2021-08-11 2022-10-13 Jnc株式会社 Composition de polymère de siloxane, produit durci, composant électronique, composant optique et élément composite

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