WO2007049722A1 - 樹脂組成物及びそれを用いた光学部材 - Google Patents
樹脂組成物及びそれを用いた光学部材 Download PDFInfo
- Publication number
- WO2007049722A1 WO2007049722A1 PCT/JP2006/321426 JP2006321426W WO2007049722A1 WO 2007049722 A1 WO2007049722 A1 WO 2007049722A1 JP 2006321426 W JP2006321426 W JP 2006321426W WO 2007049722 A1 WO2007049722 A1 WO 2007049722A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- isocyanate
- weight
- liquid
- component
- polyol
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 50
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- 150000003077 polyols Chemical class 0.000 claims abstract description 87
- 239000012948 isocyanate Substances 0.000 claims abstract description 59
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
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- 239000011347 resin Substances 0.000 claims description 51
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 41
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 17
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- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002530 phenolic antioxidant Substances 0.000 claims description 7
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 5
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 claims description 5
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- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
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- 229940035437 1,3-propanediol Drugs 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
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- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
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- C—CHEMISTRY; METALLURGY
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
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- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
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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
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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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
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/156—Heterocyclic compounds having oxygen in the ring having two oxygen atoms in the ring
- C08K5/1575—Six-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Definitions
- the present invention relates to a resin composition excellent in heat resistance, light resistance, and mechanical properties in which the cured product has high optical transparency, and a transparent substrate, lens, adhesive, and light guide using the cured product.
- the present invention relates to an optical member suitable for use in an optical semiconductor device such as a waveguide, a light emitting diode (LED), a phototransistor, a photodiode, and a solid-state imaging device, and a method for manufacturing the same.
- acrylic resin having excellent transparency and light resistance has been widely used for resin for optical members.
- the resin for optical members used in the fields of optical and electronic equipment is required to have a mounting process on an electronic substrate, heat resistance and mechanical properties under high temperature operation, and epoxy resin is often used. It was.
- the use of high-intensity laser light, blue light, and near-ultraviolet light has expanded in the field of optical and electronic devices, and a resin having better transparency, heat resistance, and light resistance than ever has been demanded.
- epoxy resin has high transparency in the visible range, but sufficient transparency cannot be obtained in the ultraviolet to near-ultraviolet range.
- cycloaliphatic epoxy resins such as cycloaliphatic bisphenol A diglycidyl ether and cured products with acid anhydride power are relatively highly transparent in the near-ultraviolet region, but are easily colored by heat and light.
- problems such as.
- Japanese Laid-Open Patent Publication No. 2003-171439 and Japanese Laid-Open Patent Publication No. 2004-75894 disclose methods for reducing impurities that are one of the causes of coloring contained in alicyclic bisphenol A diglycidyl ether.
- further improvement in heat resistance and UV resistance is required.
- silicone resin has the characteristics that it has excellent light resistance and is difficult to be colored by heat or light because of its high transparency to the near ultraviolet region and high Si-O bond energy.
- silicone resin is a dehydration condensation reaction between silanol groups, between silanol groups and hydrolyzable groups. Polymerized by condensation reaction, reaction of methylsilyl group and butylsilyl group with organic peroxide, addition reaction of vinylsilyl group and hydrosilyl group.
- Japanese Laid-Open Patent Publication No. 2004 186168 discloses a silicone resin obtained by an addition reaction between a butylsilyl group and a hydrosilyl group.
- the silicone resin obtained by using these reactions may be inhibited by a small amount of nitrogen compounds, phosphorus compounds, sulfur compounds, etc. in the curing atmosphere. There are also problems such as a large thermal expansion coefficient.
- acrylic resin has excellent transparency, light resistance, and heat-resistant colorability, but it cannot be said that mechanical properties such as breaking strength are sufficient, and further improvement of properties is required. Further, there is a problem that the volume is reduced at the time of curing when the curing shrinkage is relatively large.
- an optical component that is solvent-free and liquid at room temperature, has a small cure shrinkage, is excellent in optical properties such as transparency, light resistance, heat resistance, and mechanical properties such as breaking strength.
- a suitable rosin composition is desired.
- an optical semiconductor element used for an LED or the like may be sealed with a resin by curing a liquid thermosetting resin solution so as to cover it.
- a casting molding method in which a resin solution is cast into a mold and heat-cured is applied.
- this method has a problem that voids are easily mixed in the cured sealing resin, in addition to the problem that the thermosetting resin solution is slowly cured, resulting in poor productivity.
- Liquid transfer molding is a molding method in which liquid resin is injected, pressurized, and heat-cured into a high-temperature mold, and is useful because of short molding time and high productivity. Further, if this molding method is used, a molded product having an arbitrary shape can be obtained. However, in order to encapsulate the optical semiconductor element by applying liquid transfer molding, a transparent resin composition having a curing rate and viscosity suitable for the transfer molding is required.
- the present invention is a resin composition having excellent optical properties such as light resistance and heat-resistant coloration, in which cured cure of the cured product is small, optical transparency is high, and at the same time excellent mechanical properties such as breaking strength. Offer It is intended to serve.
- Another object of the present invention is to provide an optical member excellent in light resistance, heat resistance, and mechanical properties with high optical transparency using the resin composition with high productivity. is there. Means for solving the problem
- the present invention is characterized by the following items (1) to (15).
- the weight average molecular weight of the tri- or higher functional poly force prolatatone polyol is 800 or less, its hydroxyl value is 200 (KOH'mg / g) or more, and its acid value is 2.0 (KOH -mg / g) or less,
- the alicyclic diisocyanate is 4 4 'methylene bis (cyclohexyl isocyanate), isophorone diisocyanate, 1, 3 bis (isocyanatomethyl) cyclohexane, norbornene diisocyanate. Nate (2, 5- (2, 6) bisisocyanatomethyl [2, 2, 1] heptane) or a mixture thereof.
- the resin composition as described.
- the hindered phenolic antioxidant is 3,9bis [2- ⁇ 3- (3-tert-butyl 4-hydroxy-5-methylphenol) propiol ⁇ 1,1, dimethyl ether] 1,2, 4, 8, 10-tetraoxaspiro [5, 5] undecane or benzenepropanoic acid, 3, 5 bis (1,1-dimethylethyl) -4 hydroxy C7-C9 side chain alkyl ester (1) to (4) V, a rosin composition according to any one of the above.
- the liquid A comprises a polyol component containing a trifunctional or higher poly force prolatatone polyol and an isocyanate component containing an alicyclic diisocyanate.
- the liquid B comprises a polyol component containing a tri- or higher functional poly-prolatatone polyol and an isocyanate component containing an alicyclic diisocyanate.
- Isocyanate component P containing isocyanate groups remaining prepolymers obtained by reacting so that the isocyanate groups of the polyol component are excessive with respect to the hydroxyl groups in the polyol component.
- the rosin composition according to (1) to (6) above which is a liquid.
- the P solution and the prepolymer in the P solution are contained in the polyol component.
- the ratio (XZY) of the hydroxyl group equivalent X to the isocyanate group equivalent ⁇ in the isocyanate component is obtained by reacting such that the ratio XZY is 3 to 20 and 0.05 to 0.3, respectively ( 6) or a rosin composition according to (7).
- the gelation time at 165 ° C. is 25 to 120 seconds, (1) to (8
- Both liquids in the two-component type resin composition according to any one of (1) to (12) above have a ratio of hydroxyl group equivalent Z isocyanate group equivalent of 0.7 to 1.3.
- the resin composition of the present invention has high curing shrinkage and high optical transparency of the cured product, excellent heat resistance and light coloring resistance, and at the same time excellent mechanical properties such as breaking strength. Therefore, it is suitable as a resin composition for electronic materials such as a sealing resin for optical semiconductors. Also By applying the resin composition of the present invention having excellent heat resistance, light resistance and mechanical strength to the optical member, the life and reliability of the optical element are improved. In addition, since it can be applied to liquid transfer molding, it is possible to seal the optical semiconductor element with high productivity.
- the resin composition of the present invention is a resin composition comprising a polyol component containing a tri- or higher functional poly-prolatatone polyol and an isocyanate component containing an alicyclic diisocyanate, Two liquids: a polyol component A liquid containing a tri- or higher functional poly-prolataton polyol, and an isocyanate component B liquid containing an alicyclic diisocyanate and a hindered phenolic acid antioxidant.
- it is a type of rosin composition.
- the “two-component type of resin composition” is composed of at least two kinds of compositions, for example, component A and component B, and these can be reacted to obtain a cured product.
- a method of uniformly reacting the two-component rosin composition a method of adjusting the molecular weight of the compound in each component, a method of adding a compatibilizing agent to one or both solutions, and a compound for promoting the reaction
- the method of adjusting the molecular weight and the method of adding the compatibilizing agent are preferred because the simple method of adjusting the molecular weight is preferable.
- a reaction cured product of a bifunctional polyether diol and diisocyanate is a thermoplastic soft cured product, and is inferior in heat resistance and moisture resistance.
- the heat resistance and light resistance to coloration are poor.
- the cured product of the resin composition of the present invention forms a three-dimensional cross-linked structure by the reaction between the hydroxyl group of the poly-strength prolataton polyol and the isocyanate group of the alicyclic diisocyanate. Excellent in heat resistance, moisture resistance, light coloring resistance, and mechanical properties than the reaction-cured product of the group diisocyanate.
- a polyol component containing a tri- or higher functional poly-prolataton polyol and an isocyanate component containing an alicyclic diisocyanate are divided into a hydroxyl group in the polyol component and an isocyanate group in the isocyanate component.
- a solution containing a prepolymer obtained by reacting so that the ratio of the same is not equal, i.e., a polyol component P solution containing a prepolymer having a hydroxyl group remaining or a prepolymer having a isocyanate group remaining make an isocyanate component P solution containing
- the curing shrinkage is smaller and the compatibility is better than when making a cured product from monomers of a polyol component and an isocyanate component, so the time required for mixing and forming a uniform solution can be reduced.
- the curing speed is high, it can be used for fast curing processes such as liquid transfer molding.
- the prepolymer in the liquid P is composed of the hydroxyl equivalent X in the polyol component and the
- the polyol component and the isocyanate component are reacted so that the ratio XZY of the isocyanate group equivalent Y in the isocyanate component is 3 to 20, and the prepolymer in the liquid P is , So that the ratio XZY is 0.05-0.3.
- the polyol component is obtained by reacting the above isocyanate component.
- the ratio XZY is less than 3
- the ratio XZY is greater than 0.3, the molecular weight of the prebolimer will increase, resulting in a problem that the viscosity is high and difficult to handle. If the ratio XZY is less than 0.05, the effect of prebolimerization will be hardly obtained. End up.
- the synthesis of prepolymers can be shortened by adding a catalyst, but it is preferable to carry out the reaction at room temperature or in the absence of a catalyst to avoid coloring.
- the polyol component in the present invention includes bifunctional force prolatatone diol, carbonate diol, polyester diol, polyether diol, aliphatic diol, alicyclic diol, polyfunctional aliphatic polyol.
- various polyols such as acrylic resin polyol may be contained.
- the diol is not particularly limited, but those having a weight average molecular weight of 3,000 or less and an acid value of 2.0 (KOH'mg / g) or less preferably have a weight average molecular weight of 1,000. And an acid value of 2.0 (KOH'mg / g) or less More preferred is the one below.
- the hydroxyl value of the diol is preferably 50 (KOH'mgZg) or more, and the molecular weight distribution is preferably as narrow as possible, such as strength prolataton diol, strength sulfonate diol, polyester diol, polyether diol, aliphatic diol. 1,4 butanediol and 1,3 propanediol are particularly preferred.
- the polyfunctional polyol is preferably trimethylolpropane, propane-1,2,3 triol, or a derivative obtained by adding ethylene oxide or propylene oxide thereto.
- the trifunctional or polyfunctional prolataton polyol used in the present invention has a weight average molecular weight of 800 or less, a hydroxyl value of 200 (KOH'mgZg) or more, and an acid value of 2.0 (KOH ' mg / g) or less is preferred, and in particular liquid polyprolataton triol is preferred.
- a tri- or more functional poly force prolataton diol having a weight average molecular weight of 800 or less a hydroxyl value of 200 ( ⁇ ⁇ mg / g) or more, and an acid value of 2.0 (KOH'mg / g) or less
- a hardened product having a high density, hard and excellent heat resistance can be obtained. Further, those having a narrow molecular weight distribution are preferable.
- the tri- or higher-functional polylatal prolataton polyol is preferably contained in an amount of 50 to L00% by weight of the total polyol, 75 to 75%, and more preferably contained in an amount of L00% by weight.
- the component is preferably the various polyols described above.
- the alicyclic diisocyanate in the present invention preferably has an alicyclic skeleton and the isocyanate group is bonded to the alicyclic skeleton directly or with a methylene group.
- the isocyanate component may include, for example, isocyanurate type n-biuret type or adduct type polyisocyanate using hexamethylene diisocyanate as a raw material. An isocyanurate type polyisocyanate using good hexamethylene diisocyanate is particularly preferred.
- the rosin composition of the present invention may contain a hindered phenolic acid rust inhibitor, which may be contained in any of the above A, B, P liquid and P liquid. . Is it from the viewpoint of solubility?
- the light resistance, heat resistance, and mechanical properties of the cured resin can be remarkably improved by using a combination of a hindered phenolic acid antioxidant and a rhodium acid antioxidant.
- Examples of the hindered phenolic acid rust inhibitor include 3, 9 bis [2— ⁇ 3—
- Examples of the above xio antioxidants include tetrakis (3 laurylthiopropionic acid) pentaerythrityl, distearyl 3, 3, monothiodipropionic acid, dimyristyl-3, 3, monothiodipropionic acid, dilauryl. 3, 3, 1-thiodipropionic acid, and the like, and tetrakis (3-laurylthiopropionic acid) pentaerythrityl is particularly preferable.
- the amount of the antioxidant to be added is preferably 0.05 to 5% by weight, particularly 0.05 to 0.3% by weight, based on the total weight of the resin composition. Is preferred. When the added amount of the antioxidant is less than 0.05% by weight, the effect as an antioxidant is not seen. On the other hand, when the added amount is more than 5% by weight, the solubility and precipitation at the time of curing are not observed. There are problems. [0041] In general, the reactivity between the hydroxyl group and the alicyclic isocyanate group is slower than the reactivity between the hydroxyl group and the aromatic isocyanate. Therefore, the curing time can be shortened by adding a curing catalyst.
- the catalyst examples include, but are not limited to, organometallic catalyst of zirconium nickel, dibutyltin laurate, phenol salt of DBU, octylate, amine, imidazole, etc.
- organometallic catalysts such as aluminum sec-butyrate, ethyl acetate acetate aluminum diisopropylate, dinoleconium tributoxyacetinoreacetonate, zirconium tetraacetylethylacetonate and the like are particularly preferred.
- the amount of the catalyst added is preferably 0 to 1% by weight, particularly 0 to 0.1% by weight, based on the total weight of the resin composition. When the amount of the catalyst added is more than 1% by weight, the curing rate becomes too fast and handling of the resin composition becomes difficult. Moreover, it becomes easy to color, so that there is much addition amount.
- the resin composition of the present invention includes a hindered amine light stabilizer, a phosphorus-based antioxidant, an ultraviolet absorber, an inorganic filler, an organic filler, a coupling agent, A polymerization inhibitor can be added.
- a mold release agent, a plasticizer, an antistatic agent, a flame retardant, and the like may be added. These are preferably liquid from the viewpoint of ensuring the light transmittance of the cured resin, but it is desirable that they have a particle size equal to or smaller than the wavelength used when solid.
- the resin composition of the present invention preferably has a gel time at 165 ° C of 25 to 120 seconds.
- a gel time at 165 ° C of 25 to 120 seconds.
- the viscosity of the resin composition of the present invention is preferably 10 to 8000 mPa's at 25 ° C, and the minimum viscosity at 165 ° C is preferably 3 to 3000 mPa's. If the viscosity at 25 ° C is less than lOmPa's, the resin solution may leak into the gap of the plunger movable part in the pot part of the molding die. Also, the viscosity at 25 ° C exceeds 8000mPa's Then, it becomes difficult to inject the resin solution into the pot portion.
- the resin composition of the present invention has a heat hardness of 2 at Shore D hardness of 2 at 165 ° C for 2 minutes.
- the method for producing the optical member of the present invention using the resin composition of the present invention is not particularly limited.
- the two liquids are stirred by a method such as rotary stirring or ultrasonic dispersion, and it is necessary that the resin composition is uniform.
- it can be stored frozen after mixing with a resin to form a one-component resin solution. In this case, it can be used after thawing at room temperature before casting or potting.
- it before pouring, potting, or pouring the resin mixture into the mold, in order to remove bubbles and carbon dioxide generated by the reaction of isocyanate and moisture in the air mixed during mixing, It is desirable to vacuum degas the cocoa mixture.
- the ratio of the isocyanate group equivalent is 0.7 to 1.3, and it is more preferable to mix so that the ratio is 0.8 to 1.1.
- this ratio deviates from 0.7 to 1.3, the heat resistance, optical properties, and mechanical properties of the cured product tend to deteriorate.
- the heating conditions for curing by the casting method and the potting method are preferably about 1 to 10 hours at 60 to 150 ° C, depending on the type, combination, and amount of additive. It is particularly preferable that the 80 force is about 1 to 10 hours at 150 ° C. In addition, it is desirable to raise the curing temperature stepwise in order to reduce internal stress generated by a rapid curing reaction.
- the resin composition of the present invention is injected into a pot of a molding apparatus, and a plunger is used. The resin composition in the pot is actuated and transferred to the cavity formed by the upper mold and the lower mold, and then the resin composition is heated and cured.
- the mold temperature is preferably about 120 ° C. to 200 ° C., which is a temperature at which the resin composition can move in the mold flow path and can be cured in the cavity in a short time.
- the spray pressure of the resin composition is not particularly limited as long as it is a pressure that does not generate voids if it is not filled in the resin molding in the cavity, but it is preferably 2 MPa or more. If the injection pressure is less than 2 MPa, unfilling is likely to occur.
- a mold release agent can be applied and sprayed on the mold side.
- a vacuuming device can be used to suppress the generation of voids.
- An apparatus capable of evacuation is disclosed in, for example, Japanese Patent Application Laid-Open No. 2004-160882.
- the resin composition of the present invention is a resin composition that is excellent in heat resistance, light resistance, and mechanical properties, in which cured shrinkage of the cured product is small, optical transparency is high, and
- the cured product is suitable as an optical member for use in an optical semiconductor device such as a transparent substrate, a lens, an adhesive, an optical waveguide, a light emitting diode (LED), a phototransistor, a photodiode, and a solid-state imaging device.
- an optical semiconductor device such as a transparent substrate, a lens, an adhesive, an optical waveguide, a light emitting diode (LED), a phototransistor, a photodiode, and a solid-state imaging device.
- the resin composition of the present invention it is possible to efficiently seal an optical semiconductor element by liquid transfer molding, and it is possible to manufacture an optical semiconductor device such as an LED with high productivity. Become.
- 1,3-bis (isocyanatomethyl) cyclohexane (B1: Taketake 600 by Itakeda Chemical Co., Ltd.) 46. In 7 parts by weight, 3, 9 bis [2— ⁇ 3— (3-6-butyl-4-hydroxy-5-methylphenol) propio- as a hindered phenolic antioxidant 1, 1-dimethylethyl] 2, 4, 8, 10-tetraoxaspiro [5,5] undecane (C1: Sumitomo Chemical Sumitizer GA-80) 0.15 parts by weight, io-acid Tetrakis (3-lauryl thiopropionic acid) pentaerythrityl (D: Sumitizer made by Sumitomo Chemical Co., Ltd. TP-D) 0.15 parts by weight were mixed and dissolved to make a uniform isocyanate component B solution .
- the resin solution obtained above was poured into a mold in which a 3 mm thick and 1 mm thick silicone spacer was sandwiched between glass plates to produce a cured product.
- this resin solution is applied to the cavity part of the polyphthalamide mold for surface mount LEDs with an open dimension of 3.2 mm X 2.6 mm X height of 1.8 mm and a cavity inner diameter of ⁇ 2.4 mm. It was cast and cured to produce a surface mount LED package.
- the resin solution was poured into a resin mold for a bullet type LED having an outer dimension of 5 ⁇ and a height of 7.5 mm and cured to produce a bullet type LED knocker. The curing conditions for both LED packages were 2 hours at 60 ° C and 4 hours at 80 ° C.
- polyol component As a polyol component, 5.0 parts by weight of the above (A4) was added to 46.5 parts by weight of the above (Al) to obtain a uniform polyol component A liquid.
- norbornene diisocyanate (2, 5- (2, 6) bisisocyanatomethyl [2, 2, 1] heptane) B2: Cosmonate NBDI manufactured by Mitsui Takeda Chemical Co., Ltd. 48.2 wt.
- B2 Cosmonate NBDI manufactured by Mitsui Takeda Chemical Co., Ltd.
- 0.15 parts by weight of the above (C1) as a hindered phenolic acid antioxidant and 15 parts by weight of the above (D) O. as a silver acid antioxidant were mixed and dissolved to obtain a uniform isocyanate.
- Component B was used.
- polyol component 45.4 parts by weight of the above (Al), a polycarbonate diol having a molecular weight of 500 and a hydroxyl value of 230 (KOH ⁇ mg / g) (A5: Placel C manufactured by Daicel Chemical Industries, Ltd.) Methylolpropane (A6: manufactured by Perstorp): 1. Add 9 parts by weight and heat and stir at 60 ° C. to obtain a uniform polyol component A solution.
- isocyanate component 4-4, methylenebis (cyclohexyl isocyanate (B3: Desmodur W manufactured by Sumitomo Bayer Urethane Co., Ltd.) 28.3 parts by weight isocyanurate type polyisocyanate (B4: Asahi Kasei Chemicals Co., Ltd. deuranate THA- 100) 29.
- B3 Desmodur W manufactured by Sumitomo Bayer Urethane Co., Ltd.
- isocyanurate type polyisocyanate B4: Asahi Kasei Chemicals Co., Ltd. deuranate THA- 100
- Polyol prolatatone triol having a molecular weight of 550 and a hydroxyl value of 300 (KOH'mgZg) as the polyol component (A2: Placelel 305 manufactured by Daicel Engineering Co., Ltd.)
- Example 4 In the polyol component A liquid of Example 4, 0.1 part by weight of aluminum sec-butyrate (E: ASBD manufactured by Kawaken Fine Chemical Co., Ltd.) was added as a curing accelerator to obtain a uniform polyol component A liquid.
- E aluminum sec-butyrate
- polyol component (A1) 51.7 parts by weight and as the isocyanate component (B 1) Add 5.2 parts by weight (hydroxyl equivalent Z isocyanate group equivalent ratio 9.3) and stir for 96 hours at room temperature in a nitrogen atmosphere to obtain a polyol component P
- a liquid was prepared.
- Example 6 In the same manner as in Example 6, a surface-mounted LED package having a thickness of 1 mm and a thickness of 1 mm was prepared using the AZ isocyanate group equivalent ratio of 1.0).
- polyol component As a polyol component, add (A5) 4.0 parts by weight and (A 6) 1.6 parts by weight above (A1) to 40.9 parts by weight, dissolve them at 60 ° C, and then dissolve the isocyanate component. (B1) 4.8 parts by weight as described above (hydroxyl equivalent Z isocyanate group equivalent ratio 9.0) and stirred for 96 hours at room temperature in a nitrogen atmosphere to obtain a polyol component P solution containing a prepolymer having hydroxyl groups remaining.
- a polyol component 0.5 parts by weight of the above (A5) and 0.2 parts by weight of the above (A6) are added to 4.5 parts by weight of the above (A1) and dissolved at 60 ° C by heating. Then, 43.3 parts by weight of the above (Bl) as isocyanate component, 0.1 part by weight of the above (C1) as hindered phenolic acid antioxidant, and (D) O. 1 part by weight was added (hydroxyl equivalent: Z isocyanate group equivalent ratio: 0.11), and the mixture was stirred at room temperature for 96 hours under a nitrogen atmosphere to prepare an isocyanate component P solution containing a prepolymer having an isocyanate group remaining.
- Example 6 In the same manner as in Example 6, a surface-mount type LED package, a cured product having a thickness of 3 mm and a thickness of 1 mm was prepared using the product having the ratio of the equivalent of the carbonate group 1.0).
- polyol component (A1) 31.1 parts by weight, (A5) 6.2 parts by weight, as the isocyanate component (B3) 2.9 parts by weight, (B4) 2.8 parts by weight, coupling (F) l.0 part by weight as an agent (hydroxyl equivalent Z isocyanate group equivalent ratio 9.0), nitrogen
- the mixture was stirred at room temperature for 96 hours in an atmosphere to prepare a polyol component P solution containing a prepolymer having a hydroxyl group remaining.
- a surface mount LED package having a thickness of 1 mm and a thickness of 1 mm was prepared in the same manner as in Example 6 by using A B Z isocyanate group equivalent ratio 1.0).
- the polyol component 3.8 parts by weight of the above (A1) and 0.4 parts by weight of the above (A6) are added, and heated and stirred at 60 ° C to obtain a uniform solution, and then the isocyanate component.
- (B1) 16.0 parts by weight, (B3) 27.0 parts by weight, (B5) 7.9 parts by weight, hindered phenolic antioxidant benzenepropanoic acid, 3, 5-bis (1 , 1-dimethylethyl) -4-hydroxy C7—C9 side chain alkyl ester (C2: IRGANOX1135 manufactured by Ciba Specialty Chemicals Co., Ltd.) 0.1 part by weight (hydroxyl equivalent Z isocyanate group equivalent ratio 0.11), Under nitrogen atmosphere, the mixture was stirred at room temperature for 96 hours to prepare an isocyanate component P solution containing a prepolymer in which isocyanate groups remained.
- Example 6 In the same manner as in Example 6, the surface mount type LED package was used. A cured product of 3 mm thickness and 1 mm thickness was prepared.
- polyol component As a polyol component, 5.0 parts by weight of the above (A4) was added to 48.1 parts by weight of the above (Al) to obtain a uniform polyol component A liquid.
- 1,3-bis (isocyanatomethyl) benzene (B6: Takenate 500 manufactured by Mitsui Takeda Chemical Co., Ltd.) as an isocyanate component 33. 2 parts by weight, the above-mentioned (C1) as a hindered phenolic antioxidant 0.1 part by weight of the above-mentioned (D) 0.1 part by weight as an anti-oxidation agent was mixed and dissolved to obtain a uniform isocyanate component B solution.
- Tables 1 to 3 show the composition of liquid A (liquid P) and liquid B (liquid P) in each example and comparative example.
- A1 is a polyprolacton triol with a molecular weight of 300 and a hydroxyl value of 540 (KOH'mgZg)
- A2 has a molecular weight of 550 and a hydroxyl value of 300 (KOH'mgZg) )
- Poly force prolataton triol A3 has a molecular weight of 850 and a hydroxy value of 190 (KOH'mgZg)
- A4 has a molecular weight of 530 and a hydroxyl value of 530 (KOH'mgZg)
- A5 is a polycarbonate diol with a molecular weight of 500 and a hydroxyl value of 230 ( ⁇ mg / g)
- A6 is trimethylolpropane
- A7 has a molecular weight of 2000 and a hydroxyl value of 116 ( ⁇ mg / g g) hydroxyl group-
- the cured resin obtained in each Example and Comparative Example was measured for the flexural modulus, flexural strength, light transmittance, and yellowing degree by the methods shown below.
- the gel solutions and cured resins of Examples 6 to 10 and Comparative Examples 3 to 4 have a gelation time at 165 ° C, a viscosity at 25 ° C, and after molding.
- the Shore hardness was measured by the method shown below.
- a temperature cycle test was conducted by the following method on the bullet-type LED package, surface-mount LED package and surface-mount LED package integrally molded with the lead frame produced in each example and comparative example.
- the liquid transfer moldability was also evaluated for the surface-mount LED package fabricated by liquid transfer molding. The results are shown in Tables 4, 5 and 6.
- a 3 x 20 x 50 mm test piece was cut out and a 3-point bending test device (Instron model 5548) was used to perform a bending test with three-point support in accordance with JIS-K-6911 !, the following formula (1) And the flexural modulus and flexural strength were calculated from (2).
- the distance between the fulcrums was 24 mm, the crosshead moving speed was 0.5 mmZ, and the measurement temperature was room temperature (25 ° C).
- a spectrophotometer (Hitachi spectrophotometer V-3310), it was measured with a 1 mm thick test piece. The transmittance was measured after curing (initial stage) and after standing at high temperature for 72 hours at 150 ° C as an evaluation of heat discoloration. The yellowing degree (YI) indicating yellowishness was determined from the following equation (3) by using the measured transmission spectrum to determine the tristimulus value XYZ in the case of standard light C.
- the test condition was “ ⁇ 40 ° C for 0.5 hour, 85 ° C for 0.5 hour” as one cycle, and this was performed for 500 cycles. After the test, the separation of the resin and the case material, chips, etc., and cracks of the resin were observed using a microscope. The number of samples was 16, and if even one piece was peeled off or cracked, it was judged as defective (X), and if there was no such defect, it was marked ( ⁇ ).
- the appearance of the molded product was not filled, voids, and burrs on the lead frame were evaluated with a microscope. The number of samples is 16, and even if one sample is unfilled, voids, grease burrs, excessive deformation when removed from the mold, it is judged as defective (X). It was.
- Example 1 Example 2
- Example 3 Example 4
- Flexural modulus MPa 1800 1890 1350 1410 14 Bending strength @ Room temperature MPa>80>88>61>64> 1
- Comparative Example 1 a transparent cured product was not obtained. In Comparative Example 2, a transparent cured product was obtained, but there was a problem that the transmittance was remarkably lowered after being left at high temperature.
- the cured resins of Examples 1 to 4 were hard with an elastic modulus of lOOOMPa or higher, and exhibited a low decrease in transmittance even after standing at high temperatures with high bending strength.
- the LED packages manufactured in Examples 1 to 4 showed excellent temperature cycle characteristics with no peeling or cracking observed in the temperature cycle test, regardless of whether they were bullet-type LEDs or surface-mounted LEDs.
- the cured resin of Example 5 has a low elastic modulus of 14 MPa, which is a low elastic modulus.
- the transmittance decreased after leaving at high temperature. Fewer surface mount LED packages and excellent temperature cycling.
- the resin solutions of Examples 6 to 10 have a gelation time of 30 to 120 seconds and a viscosity of 000 mPa • s or less, and can be liquid transfer molded.
- the cured product has an elastic modulus.
- the bending strength and the transmittance were excellent, and the Shore D hardness was 20 or more, and there were no defects such as voids if not filled.
- the surface-mount type LED package produced in Example 6 to L0 showed excellent temperature cycle characteristics.
- the resin solution of Comparative Example 3 and its cured product had a transfer time with a short gelation time of 23 seconds. Many unfilled cases occurred in one molding.
- the resin solution of Comparative Example 4 and its cured product had a long gelling time and a low Shore hardness, and were not sufficiently cured during liquid transfer molding, making it difficult to take out the mold force. .
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- Polymers & Plastics (AREA)
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- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Led Device Packages (AREA)
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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EP06822395A EP1950235A4 (en) | 2005-10-27 | 2006-10-26 | RESIN COMPOSITION AND OPTICAL ELEMENT SHOWN THEREOF |
US12/091,528 US20090292049A1 (en) | 2005-10-27 | 2006-10-26 | Resin composition and optical member formed from the same |
JP2007542667A JP5277632B2 (ja) | 2005-10-27 | 2006-10-26 | 樹脂組成物及びそれを用いた光学部材 |
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JP2005312690 | 2005-10-27 | ||
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JP2006117777 | 2006-04-21 | ||
JP2006-264586 | 2006-09-28 | ||
JP2006264586 | 2006-09-28 |
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PCT/JP2006/321426 WO2007049722A1 (ja) | 2005-10-27 | 2006-10-26 | 樹脂組成物及びそれを用いた光学部材 |
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US (1) | US20090292049A1 (ja) |
EP (1) | EP1950235A4 (ja) |
JP (1) | JP5277632B2 (ja) |
KR (1) | KR20080074111A (ja) |
TW (1) | TWI401267B (ja) |
WO (1) | WO2007049722A1 (ja) |
Cited By (8)
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WO2008133271A1 (ja) * | 2007-04-24 | 2008-11-06 | Hitachi Chemical Company, Ltd. | 硬化性樹脂組成物、ledパッケージ及びその製造方法、並びに、光半導体 |
JP2009021394A (ja) * | 2007-07-12 | 2009-01-29 | Nitto Denko Corp | 光半導体素子収納用実装パッケージ用樹脂組成物およびそれを用いて得られる光半導体発光装置 |
JP2009114426A (ja) * | 2007-10-15 | 2009-05-28 | Hitachi Chem Co Ltd | 硬化性樹脂組成物、及びそれを用いたledパッケージとその製造方法 |
EP2083029A1 (en) * | 2006-11-17 | 2009-07-29 | Mitsui Chemicals, Inc. | Optical polyurethane resin composition and optical polyurethane resin |
JP2010100793A (ja) * | 2008-09-29 | 2010-05-06 | Hitachi Chem Co Ltd | 硬化性樹脂組成物、ledパッケージ、及びその製造方法 |
JP2010116534A (ja) * | 2008-10-16 | 2010-05-27 | Hitachi Chem Co Ltd | ウレタン樹脂組成物及び光半導体装置 |
JP2011012141A (ja) * | 2009-06-30 | 2011-01-20 | Mitsui Chemicals Inc | 光学用ポリウレタン樹脂組成物、光学用ポリウレタン樹脂およびその製造方法 |
JP2016008271A (ja) * | 2014-06-25 | 2016-01-18 | Dic株式会社 | 光学用ポリウレタン組成物、薄膜成形体、光学フィルム、及び薄膜成形体の製造方法 |
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KR101525523B1 (ko) | 2008-12-22 | 2015-06-03 | 삼성전자 주식회사 | 반도체 나노 결정 복합체 |
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JP6349073B2 (ja) * | 2013-11-12 | 2018-06-27 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 封止材組成物およびそれを硬化させてなる太陽電池モジュール封止材ならびにそれを用いてなる太陽電池モジュールの製造方法 |
JP6774826B2 (ja) * | 2015-09-11 | 2020-10-28 | 東洋合成工業株式会社 | 部品の製造方法 |
FR3072964B1 (fr) * | 2017-10-26 | 2020-10-23 | Soc Nouvelle Juxta | Resine transparente pour recouvrir un substrat, procede de fabrication d'une telle resine et article obtenu |
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- 2006-10-26 US US12/091,528 patent/US20090292049A1/en not_active Abandoned
- 2006-10-26 KR KR1020087010308A patent/KR20080074111A/ko not_active Application Discontinuation
- 2006-10-26 WO PCT/JP2006/321426 patent/WO2007049722A1/ja active Application Filing
- 2006-10-26 JP JP2007542667A patent/JP5277632B2/ja not_active Expired - Fee Related
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EP2083029A1 (en) * | 2006-11-17 | 2009-07-29 | Mitsui Chemicals, Inc. | Optical polyurethane resin composition and optical polyurethane resin |
EP2083029A4 (en) * | 2006-11-17 | 2013-04-10 | Mitsui Chemicals Inc | COMPOSITION FOR OPTICAL POLYURETHANE RESIN AND OPTICAL POLYURETHANE RESIN |
WO2008133271A1 (ja) * | 2007-04-24 | 2008-11-06 | Hitachi Chemical Company, Ltd. | 硬化性樹脂組成物、ledパッケージ及びその製造方法、並びに、光半導体 |
JP2009021394A (ja) * | 2007-07-12 | 2009-01-29 | Nitto Denko Corp | 光半導体素子収納用実装パッケージ用樹脂組成物およびそれを用いて得られる光半導体発光装置 |
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JP2010100793A (ja) * | 2008-09-29 | 2010-05-06 | Hitachi Chem Co Ltd | 硬化性樹脂組成物、ledパッケージ、及びその製造方法 |
JP2010116534A (ja) * | 2008-10-16 | 2010-05-27 | Hitachi Chem Co Ltd | ウレタン樹脂組成物及び光半導体装置 |
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JP2016008271A (ja) * | 2014-06-25 | 2016-01-18 | Dic株式会社 | 光学用ポリウレタン組成物、薄膜成形体、光学フィルム、及び薄膜成形体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20080074111A (ko) | 2008-08-12 |
US20090292049A1 (en) | 2009-11-26 |
TW200726783A (en) | 2007-07-16 |
EP1950235A1 (en) | 2008-07-30 |
EP1950235A4 (en) | 2012-12-26 |
TWI401267B (zh) | 2013-07-11 |
JPWO2007049722A1 (ja) | 2009-04-30 |
JP5277632B2 (ja) | 2013-08-28 |
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