WO2023054559A1 - 硬化性樹脂組成物、コーティング層、及び、フィルム - Google Patents

硬化性樹脂組成物、コーティング層、及び、フィルム Download PDF

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Publication number
WO2023054559A1
WO2023054559A1 PCT/JP2022/036372 JP2022036372W WO2023054559A1 WO 2023054559 A1 WO2023054559 A1 WO 2023054559A1 JP 2022036372 W JP2022036372 W JP 2022036372W WO 2023054559 A1 WO2023054559 A1 WO 2023054559A1
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curable resin
resin composition
weight
examples
cationically polymerizable
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PCT/JP2022/036372
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English (en)
French (fr)
Japanese (ja)
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慎也 内野
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積水化学工業株式会社
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Priority to JP2022563154A priority Critical patent/JPWO2023054559A1/ja
Publication of WO2023054559A1 publication Critical patent/WO2023054559A1/ja

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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
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/057—Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to a curable resin composition.
  • the present invention also relates to coating layers and films formed using the curable resin composition.
  • Optical semiconductor devices such as LEDs consume low power and have a long life, so they are widely used for backlights of liquid crystal display devices, lighting fixtures, and the like.
  • An optical semiconductor element deteriorates when it comes into contact with moisture or gas in the atmosphere, and the light extraction efficiency decreases.
  • a method for protecting and sealing optical semiconductor elements without using a cover glass or the like it has been studied to form a coating layer on the surface of the optical semiconductor element using a hard coating agent (for example, Patent Document 1 etc).
  • Patent Document 1 In order to improve the hardness of the curable resin composition used as a hard coating agent, it is conceivable to add a large amount of an inorganic filler, but there is a problem that the coating properties and transparency are poor.
  • Patent Document 1 a metal oxide is blended in the hard coating agent, but there has been a demand for a curable resin composition that is excellent in hardness and transparency of the cured product.
  • An object of the present invention is to provide a curable resin composition having excellent cured product hardness and transparency. Another object of the present invention is to provide a coating layer and a film formed using the curable resin composition.
  • the present disclosure 1 contains a curable resin, a photopolymerization initiator, and a metal alkoxide, and the curable resin is an organic silane compound having a cationically polymerizable group and an organic silane compound having the cationically polymerizable group.
  • the present disclosure 2 is the curable resin composition of the present disclosure 1, wherein the photopolymerization initiator includes a photocationic polymerization initiator.
  • the present disclosure 3 is the curable resin composition of the present disclosure 1 or 2, further containing an ultraviolet absorber. Disclosure 4 is the curable resin composition of Disclosure 1, 2 or 3 further comprising a leveling agent.
  • the present disclosure 5 is the curable resin composition of the present disclosure 1, 2, 3 or 4 further comprising a thixotropic agent.
  • the present disclosure 6 is a coating layer formed using the curable resin composition of the present disclosure 1, 2, 3, 4 or 5.
  • the present disclosure 7 is a film formed using the curable resin composition of the present disclosure 1, 2, 3, 4 or 5. The present invention will be described in detail below.
  • a curable resin composition having excellent cured product hardness and transparency can be obtained by using a combination of a specific cationic polymerizable compound, a photopolymerization initiator and a metal alkoxide.
  • a specific cationic polymerizable compound e.g., a photopolymerization initiator
  • a metal alkoxide e.g., a specific cationic polymerizable compound
  • a photopolymerization initiator e.g., a metal alkoxide.
  • metal alkoxides can be dissolved in a resin, and are excellent in transparency because they are free from influences such as light scattering caused by inorganic particles.
  • metal atoms can be taken in at the molecular level, it also contributes to the improvement of hardness.
  • the curable resin composition of the present invention contains a curable resin.
  • the curable resin includes an organosilane compound having a cationically polymerizable group (hereinafter also referred to as a "cationically polymerizable organosilane compound”) and a cationically polymerizable compound other than the organosilane compound having the cationically polymerizable group. .
  • the curable resin composition of the present invention has excellent applicability, hardness and transparency of the cured product. become excellent.
  • the cationically polymerizable organic silane compound and the other cationically polymerizable compound have a cationically polymerizable group.
  • Examples of the cationic polymerizable group include an epoxy group, an oxetanyl group, and a vinyl ether group. Among them, an epoxy group and an oxetanyl group are preferable.
  • the cationically polymerizable group of the cationically polymerizable organosilane compound and the cationically polymerizable group of the other cationically polymerizable compound may be the same or different.
  • the cationically polymerizable organosilane compound preferably has one or more hydrolyzable alkoxy groups in its molecule.
  • cationic polymerizable organic silane compound examples include 3-glycidoxypropyltrimethoxysilane, 2-(3,4 epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxyoctyltrimethoxysilane and the like.
  • 3-glycidoxypropyltrimethoxysilane, 2-(3,4 epoxycyclohexyl)ethyltrimethoxysilane, and 3-glycidoxypropyldiethoxysilane are preferable from the viewpoint of improving reactivity and hardness of the cured product. .
  • a preferable lower limit of the content of the cationic polymerizable organic silane compound in 100 parts by weight of the curable resin is 40 parts by weight, and a preferable upper limit thereof is 90 parts by weight.
  • the resulting curable resin composition is excellent in siloxane bond network formation.
  • the content of the cationically polymerizable organic silane compound is 90 parts by weight or less, the resulting curable resin composition is excellent in forming a copolymer of the cationically polymerizable organic silane compound and other cationically polymerizable compounds. becomes.
  • a more preferable lower limit to the content of the cationic polymerizable organic silane compound is 60 parts by weight, and a more preferable upper limit is 80 parts by weight.
  • Examples of the other cationic polymerizable compounds include 3,4-epoxycyclohexylmethyl(3,4-epoxy)cyclohexane carboxylate, 4,4′-bis(1,2-epoxycyclohexane), tetrahydroindene diepoxide, Bis(3,4-epoxycyclohexylmethyl)ether, bis(3,4-epoxycyclohexan-1-ylmethyl)adipate, 1,2-epoxy-4- of 2,2-bis(hydroxymethyl)-1-butanol (2-oxiranyl) cyclohexane adduct, [(3,4-epoxycyclohexane)-1-yl]methyl methacrylate, fluorene type epoxy compound, 1,7-octadiene diepoxide, neopentyl glycol diglycidyl ether, ethylene glycol Diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidy
  • alicyclic epoxy compounds are preferred, and 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxy 4,4′-bis(1,2-epoxycyclohexane), tetrahydroindene diepoxide, bis(3,4-epoxycyclohexylmethyl)ether are more preferred.
  • a preferable lower limit of the content of the other cationic polymerizable compound in 100 parts by weight of the curable resin is 10 parts by weight, and a preferable upper limit thereof is 60 parts by weight.
  • the content of the other cationically polymerizable compound is 10 parts by weight or more, the resulting curable resin composition becomes excellent in curability and hardness of the cured product.
  • the content of the other cationically polymerizable compound is 60 parts by weight or less, the obtained curable resin composition becomes excellent in hardness of the cured product.
  • a more preferable lower limit of the content of the other cationic polymerizable compound is 15 parts by weight, and a more preferable upper limit thereof is 40 parts by weight.
  • a preferable lower limit of the solubility parameter (hereinafter also referred to as “SP value”) of the entire curable resin is 12 (J/cm 3 ) 1/2 , and a preferable upper limit is 30 (J/cm 3 ) 1/2 .
  • SP value the solubility parameter
  • a more preferable lower limit of the SP value of the entire curable resin is 16 (J/cm 3 ) 1/2
  • a more preferable upper limit is 25 (J/cm 3 ) 1/2 .
  • the "solubility parameter” is a value calculated by the Fedors estimation method. Further, the "solubility parameter of the entire curable resin” means the average value of the solubility parameters based on the weight fraction of each curable resin component contained in the curable resin composition.
  • the curable resin composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator preferably contains a photocationic polymerization initiator.
  • the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be an ionic photoacid-generating type or a nonionic photoacid-generating type. may
  • anion portion of the ionic photoacid-generating photocationic polymerization initiator examples include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , (BX 4 ) ⁇ (wherein X is at least two or more fluorine or a phenyl group substituted with a trifluoromethyl group). Further, as the anion portion, PF m (C n F 2n+1 ) 6-m ⁇ (wherein m is an integer of 0 or more and 5 or less, and n is an integer of 1 or more and 6 or less), etc. mentioned.
  • Examples of the ionic photoacid-generating photocationic polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, (2,4-cyclo pentadien-1-yl)((1-methylethyl)benzene)-Fe salts and the like.
  • aromatic sulfonium salts include bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluorophosphate, bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluoroantimonate, bis(4-( diphenylsulfonio)phenyl)sulfide bistetrafluoroborate, bis(4-(diphenylsulfonio)phenyl)sulfidetetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate, diphenyl-4-( phenylthio)phenylsulfonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, diphenyl
  • triarylsulfonium tetrakis(pentafluorophenyl)borate such as triphenylsulfonium tetrakis(pentafluorophenyl)borate is preferable.
  • aromatic iodonium salts include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis (dodecylphenyl)iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexa fluorophosphate, 4-methylphenyl-4-(1-methylethyl)
  • aromatic diazonium salts examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis(pentafluorophenyl)borate.
  • aromatic ammonium salts examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl -2-cyanopyridinium tetrakis(pentafluorophenyl)borate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluorophosphate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluoroantimonate, 1-(naphthylmethyl) -2-cyanopyridinium tetrafluoroborate, 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate and the like.
  • Examples of the (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe salt include (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene )-Fe(II) hexafluorophosphate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) hexafluoroantimonate, (2,4-cyclopentadiene-1 -yl)((1-methylethyl)benzene)-Fe(II) tetrafluoroborate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) tetrakis(penta fluorophenyl)borate and the like.
  • nonionic photoacid-generating photocationic polymerization initiator examples include nitrobenzyl esters, sulfonic acid derivatives, phosphoric acid esters, phenolsulfonic acid esters, diazonaphthoquinone, and N-hydroxyimide sulfonates.
  • Examples of commercially available photocationic polymerization initiators include, for example, a photocationic polymerization initiator manufactured by Midori Chemical Co., Ltd., a photocationic polymerization initiator manufactured by Union Carbide, a photocationic polymerization initiator manufactured by ADEKA, Photocationic polymerization initiators manufactured by 3M, photocationic polymerization initiators manufactured by BASF, photocationic polymerization initiators manufactured by Solvay, and photocationic polymerization initiators manufactured by San-Apro. Examples of the photocationic polymerization initiator manufactured by Midori Chemical Co., Ltd. include DTS-200 and the like. Examples of photo cationic polymerization initiators manufactured by Union Carbide include UVI6990 and UVI6974.
  • Examples of photo cationic polymerization initiators manufactured by ADEKA include SP-150 and SP-170. Examples of photo cationic polymerization initiators manufactured by 3M include FC-508 and FC-512. Examples of photo cationic polymerization initiators manufactured by BASF include IRGACURE261 and IRGACURE290. Examples of photo cationic polymerization initiators manufactured by Solvay include PI2074. Examples of photo cationic polymerization initiators manufactured by San-Apro include CPI-100P, CPI-200K, CPI-210S and the like.
  • the preferable lower limit of the content of the photopolymerization initiator is 0.5 parts by weight, and the preferable upper limit thereof is 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the resulting curable resin composition is more excellent in curability and storage stability.
  • a more preferable lower limit to the content of the photopolymerization initiator is 3 parts by weight, and a more preferable upper limit is 7 parts by weight.
  • the curable resin composition of the present invention contains metal alkoxide.
  • the curable resin composition of the present invention has excellent applicability, hardness of the cured product, and transparency. It will be excellent for
  • the term "alkoxide” includes chelates and acylates. That is, the above “alkoxide” means at least one selected from the group consisting of alkoxides, chelates and acylates.
  • the metal alkoxide preferably has an SP value of 10 (J/cm 3 ) 1/2 or more and 30 (J/cm 3 ) 1/2 or less.
  • the SP value of the metal alkoxide is within this range, the compatibility with the curable resin described above is excellent, and the resulting curable resin composition has excellent transparency.
  • a more preferable lower limit of the SP value of the metal alkoxide is 15 (J/cm 3 ) 1/2 , and a more preferable upper limit is 25 (J/cm 3 ) 1/2 .
  • metal alkoxide examples include zirconium alkoxide, titanium alkoxide, lanthanoid alkoxides and the like. Among these, zirconium alkoxide is preferable because the resulting curable resin composition is more excellent in coatability and transparency.
  • metal alkoxide examples include zirconium tetraacetylacetonate (chelate), titanium tetraacetylacetonate (chelate), normal propyl zirconate (alkoxide), normal butyl zirconate (alkoxide), and zirconium monoacetylacetonate. (chelate), zirconium ethylacetoacetate (chelate), zirconium stearate (acylate), and the like.
  • zirconium tetraacetylacetonate, titanium tetraacetylacetonate, normal propyl zirconate, and normal butyl zirconate are preferable because of their high reactivity and formation of a dense network structure, and zirconium tetraacetylacetonate and titanium tetraacetyl Acetonate is more preferred.
  • a preferable lower limit is 1 part by weight and a preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the metal alkoxide is 1 part by weight or more, the obtained curable resin composition becomes excellent in hardness of the cured product.
  • the content of the metal alkoxide is 10 parts by weight or less, the resulting curable resin composition is more excellent in coatability and transparency.
  • a more preferable lower limit to the content of the metal alkoxide is 3 parts by weight, and a more preferable upper limit is 7 parts by weight.
  • the curable resin composition of the present invention preferably further contains an ultraviolet absorber.
  • Examples of the ultraviolet absorber include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, bisanilide 2-ethoxy-2'-ethyloxalate, and dimethyl-1-(2-hydroxyethyl) succinate.
  • -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-4'-n- octoxyphenyl)benzotriazole, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, phenyl salicylate, pt-butylphenyl salicylate, 2-ethylhexyl 2-cyano-3,3- diphenyl acrylate, 2-ethoxy-2'-ethyl oxalic acid bisanilide, dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpipe
  • the content of the ultraviolet absorber has a preferable lower limit of 0.001 parts by weight and a preferable upper limit of 5 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the ultraviolet absorber is within this range, the resulting curable resin composition is more excellent in light resistance.
  • a more preferable lower limit to the content of the ultraviolet absorber is 0.1 part by weight, and a more preferable upper limit is 1 part by weight.
  • the curable resin composition of the present invention preferably further contains a leveling agent.
  • leveling agent examples include silicone leveling agents, fluorine leveling agents, and acrylic leveling agents.
  • the content of the leveling agent has a preferable lower limit of 0.01 parts by weight and a preferable upper limit of 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the leveling agent is within this range, the resulting curable resin composition is more excellent in coatability and flatness of the coating film.
  • a more preferable lower limit to the content of the leveling agent is 0.03 parts by weight, and a more preferable upper limit is 1 part by weight.
  • the curable resin composition of the present invention preferably further contains a thixotropic agent.
  • thixotropic agent examples include polysiloxane, polyacryl, polyamide, polyvinyl alcohol, polyetherester, alkyl-modified cellulose, peptide, polypeptide, silica and the like.
  • the preferable lower limit of the content of the thixotropic agent is 0.1 parts by weight, and the preferable upper limit thereof is 5 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the thixotropy-imparting agent is within this range, the resulting curable resin composition is more excellent in coatability.
  • a more preferable lower limit to the content of the thixotropic agent is 1 part by weight, and a more preferable upper limit is 3 parts by weight.
  • the curable resin composition of the present invention preferably contains no solvent. By not containing the solvent, the resulting curable resin composition is excellent in low outgassing properties and does not require a solvent removal step.
  • the curable resin composition of the present invention may contain various known additives such as dyes, curing retarders, reinforcing agents, viscosity modifiers and antioxidants, if necessary.
  • the curable resin composition of the present invention preferably has a lower limit of 5 mPa ⁇ s and a preferred upper limit of viscosity measured at 25° C. using an E-type viscometer of 5000 mPa ⁇ s. When the viscosity is within this range, the resulting curable resin composition will have excellent coatability.
  • a more preferable lower limit of the viscosity is 10 mPa ⁇ s, and a more preferable upper limit is 100 mPa ⁇ s.
  • the above viscosity can be measured, for example, by using VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) as an E-type viscometer. 1 rotor can be used and measured at a rotational speed of 10 rpm or 100 rpm.
  • the curable resin composition of the present invention can be used for hard coating agents, sealing agents for displays, microlenses and the like. Among others, it is preferably used to protect and seal the optical semiconductor element or the like by forming a coating layer on the optical semiconductor element or the like, or by covering the optical semiconductor element or the like in a film form.
  • a coating layer formed using the curable resin composition of the present invention is also one aspect of the present invention.
  • a film formed using the curable resin composition of the present invention is also one aspect of the present invention.
  • the coating layer of the present invention can be formed by applying the curable resin composition of the present invention onto an object to be coated such as an optical semiconductor element and then curing the composition.
  • the film of the present invention can be formed by applying the curable resin composition of the present invention to a release film or the like and then curing the composition.
  • Examples of methods for applying the curable resin composition of the present invention include a spin coating method, a bar coating method, an inkjet method, and the like.
  • the curable resin composition of the present invention can be easily cured by light irradiation.
  • Examples of the method of curing the curable resin composition of the present invention by light irradiation include a method of irradiating light with a wavelength of 300 nm or more and 400 nm or less and an integrated light amount of 300 mJ/cm 2 or more and 3000 mJ/cm 2 or less. .
  • Examples of light sources for irradiating the curable resin composition of the present invention with light include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, excimer lasers, chemical lamps, black light lamps, microwave-excited mercury lamps, Examples include metal halide lamps, sodium lamps, halogen lamps, xenon lamps, LED lamps, fluorescent lamps, sunlight, and electron beam irradiation devices. These light sources may be used alone, or two or more of them may be used in combination. These light sources are appropriately selected according to the absorption wavelength of the photopolymerization initiator.
  • Examples of means for irradiating the curable resin composition of the present invention with light include simultaneous irradiation with various light sources, sequential irradiation with a time lag, and combined irradiation of simultaneous and sequential irradiation. means may be used.
  • the curable resin composition of the present invention may be cured by heating after the light irradiation.
  • the curable resin composition which is excellent in the hardness and transparency of hardened
  • Examples 1 to 9 and Comparative Examples 1 to 3 The curable resin compositions of Examples 1 to 9 and Comparative Examples 1 to 3 were prepared by stirring and mixing each material using a stirring mixer according to the compounding ratio shown in Table 1.
  • a stirring mixer Awatori Mixer ARE-310 (manufactured by Thinky Corporation) was used.
  • test piece was obtained in the same manner except that the thickness of the curable resin composition was applied to 30 ⁇ m by providing a gap on the glass substrate using a 30 ⁇ m thick Kapton tape. .
  • the obtained test piece was measured for pencil hardness according to JIS K 5600-5-4.
  • the obtained test piece was measured for light haze value (cloudiness) at a wavelength of 550 nm using a spectrometer ("COH-7700" manufactured by Nippon Denshoku Industries Co., Ltd.). Transparency was evaluated as " ⁇ ” when the haze value was 30% or less, and "x" when it exceeded 30%.
  • the curable resin composition which is excellent in the hardness and transparency of hardened

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Silicon Polymers (AREA)
PCT/JP2022/036372 2021-09-30 2022-09-29 硬化性樹脂組成物、コーティング層、及び、フィルム WO2023054559A1 (ja)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11260148A (ja) * 1998-03-13 1999-09-24 Hitachi Ltd 薄膜誘電体とそれを用いた多層配線板とその製造方法
JP2001232730A (ja) * 1999-12-17 2001-08-28 Toray Ind Inc ハードコートフィルム
JP2016060761A (ja) * 2014-09-16 2016-04-25 デクセリアルズ株式会社 異方性導電接着剤、及び接続構造体の製造方法
JP2017134902A (ja) * 2016-01-25 2017-08-03 日立化成株式会社 被覆導電性粒子、回路接続材料及び接続構造体
KR101965682B1 (ko) * 2018-06-12 2019-04-03 (주)켐텍인터내셔날 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치
CN110437739A (zh) * 2019-07-15 2019-11-12 淮阴工学院 环氧复合涂料及其制备方法
WO2020067046A1 (ja) * 2018-09-26 2020-04-02 デンカ株式会社 有機エレクトロルミネッセンス表示素子用封止剤

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11260148A (ja) * 1998-03-13 1999-09-24 Hitachi Ltd 薄膜誘電体とそれを用いた多層配線板とその製造方法
JP2001232730A (ja) * 1999-12-17 2001-08-28 Toray Ind Inc ハードコートフィルム
JP2016060761A (ja) * 2014-09-16 2016-04-25 デクセリアルズ株式会社 異方性導電接着剤、及び接続構造体の製造方法
JP2017134902A (ja) * 2016-01-25 2017-08-03 日立化成株式会社 被覆導電性粒子、回路接続材料及び接続構造体
KR101965682B1 (ko) * 2018-06-12 2019-04-03 (주)켐텍인터내셔날 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치
WO2020067046A1 (ja) * 2018-09-26 2020-04-02 デンカ株式会社 有機エレクトロルミネッセンス表示素子用封止剤
CN110437739A (zh) * 2019-07-15 2019-11-12 淮阴工学院 环氧复合涂料及其制备方法

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