WO2014069546A1 - 熱硬化性樹脂組成物、光反射性異方性導電接着剤及び発光装置 - Google Patents
熱硬化性樹脂組成物、光反射性異方性導電接着剤及び発光装置 Download PDFInfo
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Images
Classifications
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- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
- C08G59/3281—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen containing silicon
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- 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
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- H01L2224/44—Structure, shape, material or disposition of the wire connectors prior to the connecting process
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- H01L2224/45138—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te) and polonium (Po), and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
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- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
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- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
- H01L2224/732—Location after the connecting process
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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- H01L2924/06—Polymers
- H01L2924/078—Adhesive characteristics other than chemical
- H01L2924/07802—Adhesive characteristics other than chemical not being an ohmic electrical conductor
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/12—Passive devices, e.g. 2 terminal devices
- H01L2924/1204—Optical Diode
- H01L2924/12041—LED
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/181—Encapsulation
Definitions
- the present invention relates to a thermosetting resin composition, a light-reflective anisotropic conductive adhesive using the thermosetting epoxy adhesive, and a light-emitting device in which a light-emitting element is mounted on a wiring board using the adhesive.
- a thermosetting resin composition a thermosetting resin composition
- a light-reflective anisotropic conductive adhesive using the thermosetting epoxy adhesive
- a light-emitting device in which a light-emitting element is mounted on a wiring board using the adhesive.
- Non-Patent Document 1 As an insulating adhesive component in an anisotropic conductive paste or anisotropic conductive film.
- an LED element 33 is bonded to a substrate 31 with a die bond adhesive 32 as shown in FIG. 34 and the n-electrode 35 are wire-bonded to the connection terminal 36 of the substrate 31 with a gold wire 37, and the entire LED element 33 is sealed with a transparent mold resin 38.
- LED blocking light emitting diode
- the gold wire absorbs light having a wavelength of 400 to 500 nm emitted to the upper surface side, and part of the light emitted to the lower surface side is absorbed by the die bond adhesive 32. Since there is a problem that the luminous efficiency of the LED element 33 is lowered, as shown in FIG. 6, it is proposed to flip-chip mount the LED element 33 (Patent Document 1). .
- bumps 39 are formed on the p electrode 34 and the n electrode 35, respectively, and further, the bump formation surface of the LED element 33 is insulated from the p electrode 34 and the n electrode 35.
- the light reflecting layer 40 is provided on the surface.
- the LED element 33 and the substrate 31 are connected and fixed by using an anisotropic conductive paste 41 or an anisotropic conductive film (not shown) and curing them. For this reason, in the light emitting device of FIG. 6, the light emitted upward of the LED element 33 is not absorbed by the gold wire, and most of the light emitted downward is reflected by the light reflecting layer 40 and emitted upward. The light emission efficiency (light extraction efficiency) does not decrease.
- Non-Patent Document 1 when a two-component curable methylsilicone resin or a two-component curable phenylsilicone resin as described in Non-Patent Document 1 is used as an insulating adhesive component of an anisotropic conductive adhesive, it is insulated by heat or light. Although the discoloration of the adhesive adhesive component can be suppressed, there is a problem that the peel strength (die shear strength) of the LED element with respect to the mounting substrate becomes a level unsuitable for practical use.
- the light reflecting layer 40 must be provided on the LED element 33 by a metal vapor deposition method or the like so as to be insulated from the p electrode 34 and the n electrode 35, and an increase in manufacturing cost is inevitable.
- the surface of the conductive particles coated with gold, nickel or copper in the cured anisotropic conductive paste or anisotropic conductive film is brown or
- the epoxy resin binder itself which exhibits a dark brown color and in which conductive particles are dispersed, also exhibits a brown color because of the imidazole-based latent curing agent that is commonly used for its curing. There is a problem that it is difficult to improve the light emission efficiency (light extraction efficiency).
- a first object of the present invention is to solve the above-mentioned problems of the prior art, and to mount a light emitting element such as a light emitting diode (LED) element on a wiring board using an anisotropic conductive adhesive.
- a thermosetting resin composition as an insulating adhesive component suitable for anisotropic conductive adhesives that are resistant to discoloration by heat and light and exhibit practically sufficient die shear strength when manufacturing light emitting devices
- the second object is to provide a light-reflective anisotropic conductive adhesive that can improve the light emission efficiency without providing a light-reflective layer on the LED element that causes an increase in manufacturing cost.
- it is to provide a light emitting device in which a light emitting element is flip-chip mounted on a wiring board using such a light reflective anisotropic conductive adhesive.
- the present inventors have disclosed an epoxy group-containing siloxane compound having a specific structure as an insulating adhesive component of an anisotropic conductive adhesive, more specifically tetrakis (diglycidyl isocyanuryl-modified siloxy). It was found that the use of silane can prevent the anisotropic conductive adhesive from being discolored by heat or light, and exhibits practically sufficient die shear strength.
- the inventors of the present invention have assumed that the anisotropic conductive adhesive itself has a light reflecting function, so that the luminous efficiency can be prevented from being lowered. Furthermore, it has been found that the light-emitting efficiency of the light-emitting element can be prevented from being lowered by blending light-reflective insulating particles. And based on these knowledge, it came to complete this invention.
- this invention contains the epoxy group containing siloxane compound represented by Formula (1), and the hardening
- the thermosetting resin composition characterized by the above-mentioned. I will provide a.
- the substituent R is independently an alkyl group or a phenyl group.
- the linking group A is independently a divalent hydrocarbon group.
- the substituents R1 and R2 are independently an epoxy group-containing organic group, an alkyl group, or an aryl group, and at least one of R1 and R2 is an epoxy group-containing organic group.
- the present invention also provides a light-reflective anisotropic conductive adhesive used for anisotropic conductive connection of a light emitting element to a wiring board in order to achieve the second object, represented by the formula (1).
- a light-reflective anisotropy comprising the thermosetting resin composition of the present invention, the conductive particles, and the light-reflective insulating particles, comprising the epoxy group-containing siloxane compound and the epoxy resin curing agent
- a conductive adhesive is provided.
- a light-reflective anisotropic conductive adhesive which is a light-reflective conductive particle comprising a light-reflecting layer formed from at least one kind of inorganic particles selected from particles or aluminum oxide particles.
- the present invention provides a light emitting device in which a light emitting element is mounted on a wiring board by a flip chip method through the above-described light reflective anisotropic conductive adhesive.
- thermosetting resin composition of the present invention useful as a binder for an anisotropic conductive adhesive used for anisotropic conductive connection of a light emitting element to a wiring board is a formula (1) that cures with a curing agent for epoxy resin.
- the epoxy group containing siloxane compound represented by these is contained.
- this siloxane compound four silyleneoxy groups are bonded to the center silicon atom, and an isocyanurylalkyl group substituted with an epoxy group-containing organic group is bonded to the terminal of each silyleneoxy group. It has the structure. For this reason, it can prevent that an anisotropic conductive adhesive discolors with a heat
- this thermosetting resin composition is useful not only as an anisotropic conductive adhesive but also as a binder for an insulating adhesive or a conductive adhesive.
- the light-reflective anisotropic conductive adhesive of the present invention contains light-reflective insulating particles in addition to the effect of the thermosetting resin composition, it can reflect light.
- the light-reflective insulating particles are at least one inorganic particle selected from the group consisting of titanium oxide, boron nitride, zinc oxide and aluminum oxide, or a resin in which the surface of scaly or spherical metal particles is coated with an insulating resin.
- coated metal particles since the particles themselves are almost white, the wavelength dependency of the reflection characteristic with respect to visible light is small, so that the light emission efficiency can be improved and the light emission color of the light emitting element remains unchanged. Can be reflected by color.
- conductive particles a core particle coated with a metal material, and a white to gray light reflecting layer formed on the surface thereof from titanium oxide particles, boron nitride particles, zinc oxide particles or aluminum oxide particles.
- the light-reflective conductive particles themselves exhibit a white to gray color, so that the wavelength dependence of the reflection characteristics with respect to visible light is small, thus further improving the luminous efficiency.
- the emission color of the light emitting element can be reflected as it is.
- FIG. 1A is a cross-sectional view of light-reflective conductive particles for a light-reflective anisotropic conductive adhesive.
- FIG. 1B is a cross-sectional view of light-reflective conductive particles for a light-reflective anisotropic conductive adhesive.
- FIG. 2 is a cross-sectional view of the light emitting device of the present invention.
- FIG. 3 is an FT-IR measurement chart of the epoxy group-containing siloxane compound of the formula (1a) produced in Example 1.
- FIG. 4 is a 1 H-NMR measurement chart of the epoxy group-containing siloxane compound of the formula (1a) produced in Example 1.
- FIG. 5 is a cross-sectional view of a conventional light emitting device.
- FIG. 6 is a cross-sectional view of a conventional light emitting device.
- thermosetting resin composition of the present invention contains an epoxy group-containing siloxane compound represented by the formula (1) and a curing agent for epoxy resin.
- This thermosetting resin composition is useful as a binder for a light-reflective anisotropic conductive adhesive used for anisotropic conductive connection of a light emitting element to a wiring board.
- thermosetting resin composition of the present invention contains an epoxy group-containing siloxane compound represented by formula (1) and a curing agent for epoxy resin.
- an epoxy group-containing siloxane compound represented by the formula (1) it is possible to prevent the anisotropic conductive adhesive from being discolored by heat or light, and to achieve practically sufficient die shear strength. Can do.
- R is an alkyl group or a phenyl group independently.
- An alkyl group is preferred from the viewpoint of difficulty in discoloration.
- Examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms from the viewpoint of adhesion to a substrate, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert- A butyl group, a heptyl group, an isoheptyl group, and a hexyl group are preferable, and among them, a lower alkyl group having 1 to 3 carbon atoms such as a methyl group, an ethyl group, a propyl group, and an isopropyl group are preferable.
- a methyl group is preferable from the viewpoint of heat-resistant yellowing resistance.
- A is independently a divalent hydrocarbon group, for example, an alkylene group having 2 or more carbon atoms, an arylene group, or an aralkylene group, and an alkylene group having 2 or more carbon atoms is preferable from the viewpoint of difficulty in discoloration.
- an alkylene group having 2 or more carbon atoms for example, an alkylene group having up to 6 carbon atoms is preferable, and specific examples include a dimethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
- An alkyl group such as a methyl group may be bonded to these alkylene groups.
- arylene group examples include a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 1,4-naphthalene group, and a 1,5-naphthalene group.
- a 1,4-phenylene group is preferred.
- Examples of the aralkylene group include a phenyl dimethylene group and a phenyl trimethylene group.
- the substituents R1 and R2 are independently an epoxy group-containing organic group, an alkyl group, or an aryl group, but at least one of R1 and R2, preferably both, is an epoxy group-containing organic group.
- Examples of the epoxy group-containing organic group include glycidyl group, 1,2-epoxy-5-hexenyl group, 2,6-dimethyl-2,3-epoxy-7-octenyl group, and 1,2-epoxy-9-decenyl. Groups. Among these, a glycidyl group is preferable from the viewpoint of adhesiveness with a substrate.
- the substituent R is a lower alkyl group having 1 to 3 carbon atoms
- the linking group A is an alkylene group having 2 to 6 carbon atoms.
- the substituents R1 and R2 are both epoxy group-containing organic groups.
- a particularly preferred embodiment of the epoxy group-containing siloxane compound represented by the formula (1) is a compound represented by the following formula (1a).
- the amount is preferably 45 to 65% by mass, more preferably 50 to 60% by mass.
- the epoxy group-containing siloxane compound represented by the formula (1) as shown in the following reaction formula (so-called hydrosilylation reaction), tetrakis (hydrogensilyleneoxysilane) of the formula (a) and the formula (b ) Isocyanurate, and then in the presence of a Karlstedt catalyst (1,3-divinyl-1,1,3,3-tetramethyldisiloxane platinum (0) complex solution) at room temperature to The compound of the formula (1) can be isolated from the reaction mixture by a conventional method (concentration treatment, column treatment, etc.).
- R, A, R1 and R2 are as described in formula (1).
- a ′ is a terminal alkenyl group corresponding to the linking group A.
- A is a dimethylene group, it is a vinyl group, when it is a trimethylene group, it is an allyl group, and when it is a hexamethylene group, it is a 5-hexenyl group.
- the compound of formula (1a) which is a particularly preferred embodiment of the epoxy group-containing siloxane compound of formula (1), is also represented by the following formula: tetrakis (hydrogendimethylsiloxy) silane of formula (a ′) and formula (b ′ ) Of 1-allyl-3,5-diglycidyl isocyanurate.
- thermosetting resin composition of the present invention is a heterocyclic epoxy compound, an alicyclic epoxy compound, or a hydrogenated epoxy compound as long as the effects of the invention are not impaired. Etc. can be contained.
- heterocyclic epoxy compound examples include epoxy compounds having a triazine ring, such as 1,3,5-tris (2,3-epoxypropyl) -1,3,5-triazine-2,4,6- (1H, 3H , 5H) -trione (in other words, triglycidyl isocyanurate).
- Preferred examples of the alicyclic epoxy compound include those having two or more epoxy groups in the molecule. These may be liquid or solid. Specific examples include glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate, and the like. Among these, glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 ′, 4 is preferable because it can ensure light transmission suitable for mounting LED elements on the cured product and is excellent in rapid curing. '-Epoxycyclohexenecarboxylate can be preferably used.
- hydrogenated epoxy compound hydrogenated products of the aforementioned heterocyclic epoxy compounds and alicyclic epoxy compounds, and other known hydrogenated epoxy resins can be used.
- alicyclic epoxy compounds, heterocyclic epoxy compounds and hydrogenated epoxy compounds may be used alone or in combination of two or more with respect to the epoxy group-containing siloxane compound of formula (1). Good. In addition to these epoxy compounds, other epoxy compounds may be used in combination as long as the effects of the present invention are not impaired.
- epoxy resin curing agent a known epoxy resin curing agent can be used.
- amine curing agent, polyamide curing agent, acid anhydride curing agent, imidazole curing agent, polymercaptan curing agent, polysulfide curing agent, boron trifluoride-amine complex curing agent, dicyandiamide, organic acid It can be selected from among hydrazides and the like.
- acid anhydride curing agents can be preferably used from the viewpoints of light transmittance, heat resistance, and the like.
- Acid anhydride curing agents include succinic anhydride, phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydro Phthalic anhydride, or a mixture of 4-methyl-hexahydrophthalic anhydride and hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl-tetrahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, norbornane-2,3-dicarboxylic acid An acid anhydride, methylnorbornane-2,3-dicarboxylic acid anhydride, methylcyclohexene dicarboxylic acid anhydride, etc. can be mentioned.
- the amount of the epoxy resin curing agent such as an acid anhydride curing agent in the thermosetting resin composition is too small relative to 100 parts by mass of the epoxy group-containing siloxane compound represented by the formula (1),
- the amount of the cured epoxy component increases, and if the amount is too large, the corrosion of the adherend material tends to be accelerated due to the influence of the excess curing agent. Therefore, the amount is preferably 50 to 120 parts by mass, more preferably 60 to 100 parts by mass. is there.
- the thermosetting resin composition of the present invention can contain a known curing accelerator in order to complete the curing reaction smoothly and in a short time.
- Preferred curing accelerators include quaternary phosphonium salt-based curing accelerators and imidazole-based curing accelerators. Specific examples include quaternary phosphonium bromide salts (“U-CAT5003” (trademark), manufactured by San Apro), 2-ethyl-4-methylimidazole, and the like.
- U-CAT5003 quaternary phosphonium bromide salts
- an imidazole curing accelerator can be preferably used as a curing accelerator for an acid anhydride curing agent.
- the imidazole curing accelerator is preferably 0.20 to 2.00 parts by mass, and more preferably 0.60 to 1.00 parts by mass with respect to parts.
- thermosetting resin composition of the present invention described above is as colorless and transparent as possible when used as a binder that is an insulating adhesive component of a light-reflective anisotropic conductive adhesive for mounting a light-emitting element. It is preferable. This is because the light-reflecting conductive particles in the light-reflective anisotropic conductive adhesive are reflected without lowering the light reflection efficiency and without changing the light color of the incident light.
- colorless and transparent means that the light-reflective anisotropic conductive adhesive cured product has a light transmittance (JIS K7105) of 80% or more with respect to visible light having a wavelength of 380 to 780 nm, preferably 80% or more. It means 90% or more.
- thermosetting resin composition of the present invention is produced by mixing the epoxy group-containing siloxane compound of formula (1), the curing agent for epoxy, and other components blended as necessary by a known method. can do.
- This light-reflective anisotropic conductive adhesive contains a thermosetting resin composition, conductive particles and light-reflective insulating particles, and the thermosetting resin composition contains an epoxy group represented by the formula (1).
- the thermosetting resin composition of the present invention contains a siloxane compound and an epoxy resin curing agent.
- the light-reflective insulating particles contained in the light-reflective anisotropic conductive adhesive of the present invention are for reflecting light incident on the anisotropic conductive adhesive to the outside.
- the light-reflective particles include metal particles, particles coated with metal particles, inorganic particles such as metal oxides, metal nitrides, and metal sulfides that are gray to white under natural light, resin core particles
- corrugation on the surface are contained irrespective of the material of particle
- the light-reflective insulating particles that can be used in the present invention do not include metal particles that are not covered with insulation because they are required to exhibit insulating properties.
- Such light-reflective insulating particles include at least selected from the group consisting of titanium oxide (TiO 2 ), boron nitride (BN), zinc oxide (ZnO), and aluminum oxide (Al 2 O 3 ).
- TiO 2 titanium oxide
- BN boron nitride
- ZnO zinc oxide
- Al 2 O 3 aluminum oxide
- TiO 2 it is preferable to use TiO 2 from the viewpoint of a high refractive index.
- the shape of the light-reflective insulating particles may be spherical, scaly, irregularly shaped, or needle-like, but considering the reflection efficiency, spherical and scaly are preferable. Further, in the case of a spherical shape, if it is too small, the reflectance is low, and if it is too large, the connection by anisotropic conductive particles tends to be inhibited.
- the major axis is preferably 0.1 to 100 ⁇ m, more preferably 1 to 50 ⁇ m, and the minor axis is preferably 0.01 to 10 ⁇ m, and more preferably 0.8.
- the thickness is preferably 1 to 5 ⁇ m, and the thickness is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- the light-reflective insulating particles made of inorganic particles have a refractive index (JIS K7142) that is preferably larger than the refractive index of a cured product of the thermosetting resin composition (JIS K7142), more preferably at least 0.02. It is preferable that the degree is large. This is because when the difference in refractive index is small, the reflection efficiency at the interface between them decreases.
- the inorganic particles described above may be used, but resin-coated metal particles obtained by coating the surface of scale-like or spherical metal particles with a transparent insulating resin may be used.
- the metal particles include nickel, silver, and aluminum.
- the shape of the particles include an amorphous shape, a spherical shape, a scaly shape, and a needle shape.
- a spherical shape is preferable from the viewpoint of the light diffusion effect
- a scaly shape is preferable from the viewpoint of the total reflection effect.
- they are scaly silver particles or spherical silver particles.
- the particle diameter is preferably from 0.1 to 30 ⁇ m, more preferably from 0.2 to 10 ⁇ m.
- the long diameter is preferably from 0.1 to 100 ⁇ m, more preferably from 1 to
- the thickness at 50 ⁇ m is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- the size of the light-reflective insulating particles is the size including the insulating coating when the insulating coating is applied.
- a cured product of acrylic resin can be preferably used.
- a preferable example is a resin obtained by radical copolymerization of methyl methacrylate and 2-hydroxyethyl methacrylate in the presence of a radical initiator such as an organic peroxide such as benzoyl peroxide.
- a radical initiator such as an organic peroxide such as benzoyl peroxide.
- it is more preferably crosslinked with an isocyanate-based crosslinking agent such as 2,4-tolylene diisocyanate.
- the metal particles it is preferable to introduce a ⁇ -glycidoxy group, a vinyl group, or the like into the metal surface in advance with a silane coupling agent.
- such resin-coated metal particles are prepared by adding metal particles and a silane coupling agent in a solvent such as toluene and stirring the mixture at room temperature for about 1 hour, and then, if necessary, a radical monomer and a radical polymerization initiator. Then, a crosslinking agent is added, and the mixture is stirred by heating to the radical polymerization starting temperature.
- the light-reflective insulating particles in the light-reflective anisotropic conductive adhesive are preferably 1 to 50% by volume, more preferably 5 to 25% by volume.
- conductive particles constituting the light-reflective anisotropic conductive adhesive of the present invention metal particles used in conventional conductive particles for anisotropic conductive connection can be used. Examples thereof include gold, nickel, copper, silver, solder, palladium, aluminum, alloys thereof, multilayered products thereof (for example, nickel plating / gold flash plating products), and the like. Above all, gold, nickel, and copper turn the conductive particles brown, so that the effects of the present invention can be enjoyed over other metal materials.
- metal-coated resin particles obtained by coating resin particles with a metal material can be used.
- resin particles include styrene resin particles, benzoguanamine resin particles, and nylon resin particles.
- a method of coating the resin particles with a metal material a conventionally known method can be employed, and an electroless plating method, an electrolytic plating method, or the like can be used.
- the layer thickness of the metal material to be coated is sufficient to ensure good connection reliability, and is usually 0.1 to 3 ⁇ m although it depends on the particle size of the resin particles and the type of metal.
- the particle size of the resin particle is too small, poor conduction tends to occur, and if it is too large, there is a tendency for a short circuit between patterns to occur. Therefore, it is preferably 1 to 20 ⁇ m, more preferably 3 to 10 ⁇ m, and particularly preferably 3 to 5 ⁇ m. is there.
- the shape of the core particle 1 is preferably a spherical shape, but may be a flake shape or a rugby ball shape.
- the metal-coated resin particles have a spherical shape, and if the particle size is too large, the connection reliability is lowered. Therefore, it is preferably 1 to 20 ⁇ m, more preferably 3 to 10 ⁇ m.
- 1A and 1B are sectional views of such light-reflective conductive particles 10 and 20. First, the light reflective conductive particles in FIG. 1A will be described.
- the light-reflective conductive particles 10 include a core particle 1 coated with a metal material, and titanium oxide (TiO 2 ) particles, boron nitride (BN) particles, zinc oxide (ZnO) particles, or aluminum oxide (Al 2 ) on the surface thereof. And a light reflecting layer 3 formed of at least one kind of inorganic particles 2 selected from O 3 ) particles. Titanium oxide particles, boron nitride particles, zinc oxide particles, or aluminum oxide particles are inorganic particles that exhibit white under sunlight. Accordingly, the light reflecting layer 3 formed from them exhibits white to gray.
- the expression of white to gray means that the wavelength dependency of the reflection characteristic for visible light is small and the visible light is easily reflected.
- titanium oxide particles boron nitride particles, zinc oxide particles, or aluminum oxide particles
- zinc oxide particles which are not catalytic to photodegradation and have a high refractive index.
- the surface thereof is made of a metal material.
- the surface is coated with a metal material, as described above, an aspect in which the core particle 1 itself is a metal material, or an aspect in which the surface of the resin particle is coated with a metal material can be given.
- the thickness of the light reflecting layer 3 formed from the inorganic particles 2 is too low with respect to the particle size of the core particle 1. If it is too large, poor conduction will occur. Therefore, it is preferably 0.5 to 50%, more preferably 1 to 25%.
- the particle size of the inorganic particles 2 constituting the light-reflecting layer 3 is preferably 0.02 to 4 ⁇ m, more preferably 0.1 to 1 ⁇ m, and particularly preferably 0.2 to 0.5 ⁇ m.
- the particle size of the inorganic particles 2 is set so that the light to be reflected (that is, the light emitted from the light emitting element) is not transmitted. It is preferable that it is 50% or more.
- examples of the shape of the inorganic particles 2 include an amorphous shape, a spherical shape, a scaly shape, and a needle shape.
- a spherical shape is preferable from the viewpoint of the light diffusion effect
- a scaly shape is preferable from the viewpoint of the total reflection effect.
- the light-reflective conductive particles 10 in FIG. 1A are formed by a known film forming technique (so-called mechano-fusion method) in which a film composed of small-sized particles is formed on the surface of large-sized particles by physically colliding large and small powders. ).
- the inorganic particles 2 are fixed so as to bite into the metal material on the surface of the core particle 1, and on the other hand, the inorganic particles monolithically constitute the light reflecting layer 3 because the inorganic particles are not easily fused and fixed together. Therefore, in the case of FIG. 1A, the layer thickness of the light reflecting layer 3 is considered to be equivalent to or slightly thinner than the particle size of the inorganic particles 2.
- the light reflective conductive particles 20 in FIG. 1B will be described.
- the light-reflecting layer 3 contains a thermoplastic resin 4 that functions as an adhesive
- the inorganic particles 2 are also fixed together by this thermoplastic resin 4, and the inorganic particles 2 are multilayered (for example, It differs from the light-reflective conductive particle 10 of FIG. 1A in that it is multi-layered into two or three layers.
- thermoplastic resin 4 By including such a thermoplastic resin 4, the mechanical strength of the light reflecting layer 3 is improved, and the inorganic particles are less likely to be peeled off.
- thermoplastic resin 4 a halogen-free thermoplastic resin can be preferably used for the purpose of low environmental load, and for example, polyolefins such as polyethylene and polypropylene, polystyrene, acrylic resins and the like can be preferably used.
- Such light-reflective conductive particles 20 can also be manufactured by a mechanofusion method. If the particle diameter of the thermoplastic resin 4 applied to the mechano-fusion method is too small, the adhesion function is lowered, and if it is too large, it is difficult to adhere to the core particles, so that it is preferably 0.02 to 4 ⁇ m, more preferably 0.1 ⁇ 1 ⁇ m. Further, if the amount of the thermoplastic resin 4 is too small, the adhesive function is lowered, and if it is too large, aggregates of particles are formed. The amount is 2 to 500 parts by mass, more preferably 4 to 25 parts by mass.
- the blending amount of the conductive particles such as the light-reflective conductive particles in the light-reflective anisotropic conductive adhesive of the present invention is too small, conduction failure tends to occur, and if it is too large, there is a tendency to cause a short circuit between patterns. Therefore, the blending amount of conductive particles such as light-reflective conductive particles with respect to 100 parts by mass of the thermosetting resin composition is preferably 1 to 100 parts by mass, more preferably 10 to 50 parts by mass.
- the light-reflective anisotropic conductive adhesive of the present invention can be produced by uniformly mixing the light-reflective insulating particles, the conductive particles, and the thermosetting resin composition described above according to a conventional method.
- light-reflective anisotropic conductive films they are dispersed and mixed together with a solvent such as toluene, and applied to a peeled PET film so as to have a desired thickness, and a temperature of about 80 ° C. Just dry.
- the reflection characteristic of the light-reflective anisotropic conductive adhesive of the present invention is such that the reflectance of the cured light-reflective anisotropic conductive adhesive to light having a wavelength of 450 nm (JIS) is improved in order to improve the light emission efficiency of the light-emitting element.
- K7105 is at least 30%.
- the reflection characteristics and blending amount of the light-reflective conductive particles to be used, the blending composition of the thermosetting resin composition, and the like may be appropriately adjusted. Usually, if the amount of the light-reflective conductive particles having good reflection characteristics is increased, the reflectance tends to increase.
- the reflection characteristics of the light-reflective anisotropic conductive adhesive can be evaluated from the viewpoint of refractive index. That is, when the refractive index of the cured product is larger than the refractive index of the cured product of the thermosetting resin composition excluding the conductive particles and the light-reflective insulating particles, the light-reflective insulating particles and the heat surrounding them are obtained. This is because the amount of light reflection at the interface between the curable resin composition and the cured product increases.
- the difference obtained by subtracting the refractive index of the cured product of the thermosetting resin composition (JIS K7142) from the refractive index of the light reflective particles (JIS K7142) is preferably 0.02 or more, more preferably It is desired to be 0.2 or more.
- the refractive index of a thermosetting resin composition mainly composed of an epoxy resin is about 1.5.
- the light-emitting device 200 includes the connection terminal 22 on the substrate 21 and the connection bumps 26 formed on the n-electrode 24 and the p-electrode 25 of the LED element 23 as light-emitting elements.
- This is a light emitting device in which a light reflective anisotropic conductive adhesive is applied and the substrate 21 and the LED element 23 are flip-chip mounted.
- the light-reflective anisotropic conductive adhesive cured product 100 is formed by dispersing the light-reflective insulating particles 10 in the cured product 11 of the thermosetting resin composition.
- the light emitting device 200 configured as described above, among the light emitted from the LED element 23, the light emitted toward the substrate 21 is light in the cured product 100 of the light-reflective anisotropic conductive adhesive. The light is reflected by the reflective insulating particles 10 and emitted from the upper surface of the LED element 23. Accordingly, it is possible to prevent a decrease in luminous efficiency.
- Configurations other than the light-reflective anisotropic conductive adhesive (the LED element 23, the bump 26, the substrate 21, the connection terminal 22, and the like) in the light-emitting device 200 of the present invention can be the same as the configuration of the conventional light-emitting device. .
- the light emitting device 200 of the present invention can be manufactured by using a conventional anisotropic conductive connection technique except that the light reflective anisotropic conductive adhesive of the present invention is used.
- a well-known light emitting element can be applied in the range which does not impair the effect of this invention other than an LED element.
- FT-IR measurement FT-IR measurement (measurement) for the hydrosilylation reaction residue under reduced pressure and the raw materials 1-allyl-3,5-diglycidyl isocyanurate (MADGIC) and tetrakis (hydrogendimethylsiloxy) silane (SIT7278.0)
- MADGIC 1-allyl-3,5-diglycidyl isocyanurate
- SIT7278.0 tetrakis (hydrogendimethylsiloxy) silane
- FIG. The starting material, tetrakis (hydrogen dimethylsiloxy) silane (SIT7278.0), as Si-H group-specific spectral, stretching peak around 2140 cm -1, is bending vibration peak near 900 cm -1 were detected.
- thermosetting resin composition of the present invention was prepared as an insulating adhesive by uniformly mixing the components of the composition shown in Table 1 using the obtained epoxy group-containing siloxane compound.
- an epoxy compound and an acid anhydride curing agent were blended so that the ratio of the number of functional groups of epoxy group / acid anhydride was 1 / 1.1.
- thermosetting resin composition as the insulating adhesive of Comparative Example 1 is an example in which 1,3,5-triglycidyl isocyanate is used as the epoxy compound in place of the epoxy group-containing siloxane compound of the formula (1a).
- the thermosetting resin composition as the insulating adhesive of Comparative Example 2 is a two-component curable dimethyl silicone resin (IVS4742, Momentive Materials), and the thermosetting as the insulating adhesive of Comparative Example 3
- the conductive resin composition is a two-component curable phenyl silicone resin (SCR-1012, Shin-Etsu Chemical Co., Ltd.).
- thermosetting resin composition as the obtained insulating adhesive was subjected to a die shear strength test, a heat resistance test, and a heat resistance light test. The obtained results are shown in Table 2.
- a glass epoxy substrate for LED (special order product, Kansai Electronics Co., Ltd.) having a silver solid electrode with a thickness of 10 ⁇ m on which gold bumps (high 10 ⁇ m, diameter 80 ⁇ m, pitch 190 ⁇ m) are formed so that the diameter is 4 mm.
- the LED element was placed on a held hot plate and heated for 2 minutes to temporarily fix the LED element on the glass epoxy substrate for LED.
- the glass epoxy substrate for LED to which this LED element is temporarily fixed, is applied to a thermocompression bonding apparatus and subjected to thermocompression bonding at 230 ° C. for 15 seconds while applying a pressure of 80 gf / chip to the LED element.
- An LED device having LED elements mounted on a substrate was created.
- a reflow treatment at 260 ° C. for 20 seconds was further performed after the thermocompression treatment.
- the die shear strength (gf / chip) was measured for the LED device thus prepared.
- the die shear strength is desired to be at least 200 gf / chip, preferably 250 gf / chip or more.
- Example 1 and Comparative Example 1 are sandwiched between two aluminum flat plates (length 100 mm ⁇ width 50.0 mm ⁇ thickness 0.50 mm) in which spacers having a height of 1 mm are arranged at the four corners.
- a cured resin sheet sample was prepared by first heating at 120 ° C. for 30 minutes and then heating at 140 ° C. for 1 hour.
- a cured resin sheet sample was prepared by first heating at 80 ° C. for 1 hour and then heating at 150 ° C. for 2 hours.
- the obtained cured resin sheet sample was left in an oven set at 150 ° C. for 1000 hours, and the spectral characteristics (L * , a * , b * ) before and after being left were measured with a spectrocolorimeter (CM-3600d, Konica). Minolta Optics Co., Ltd.), and the color difference ( ⁇ E) was calculated from the measured values.
- ⁇ E is desirably 35 or less.
- ⁇ Heat-resistant light test> A cured resin sheet sample similar to the cured resin sheet sample subjected to the heat resistance test was prepared, and the cured resin sheet sample was prepared at a temperature of 120 ° C. with a light intensity of 16 mW / cm 2 (super win mini, die pla wintes ( ); Used in a metal halide lamp) for 1000 hours, and the resulting cured resin sheet is left in an oven set at 150 ° C. for 1000 hours to obtain spectral characteristics before and after being left (L * , a * , b *). ) was measured using a spectrocolorimeter (CM-3600d, Konica Minolta Optics, Inc.), and the color difference ( ⁇ E) was calculated from the obtained measured values. Practically, ⁇ E is desired to be 20 or less.
- the cured resin sheet sample using the epoxy group-containing siloxane compound of Example 1 as a curing component was practically preferable in terms of die shear strength, heat resistance test and heat resistance light test.
- Comparative Example 1 since a thermosetting epoxy resin composition was used, a favorable result was obtained for the die shear strength, but the epoxy-containing siloxane compound of the formula (1a) was not used. Satisfactory results were not obtained for the heat resistance test.
- Example 2 For 100 parts by mass of the thermosetting resin composition of Example 1 as an insulating adhesive, light-reflective insulating particles (titanium dioxide powder having an average particle size of 0.5 ⁇ m (KR-380, Titanium Industry Co., Ltd.)) 24 0.0 parts by mass and conductive particles (gold-coated resin conductive particles having an average particle size of 5 ⁇ m (particles obtained by electroless gold plating of 0.2 ⁇ m thickness on spherical acrylic resin particles having an average particle size of 4.6 ⁇ m) (Light 20GNB4, Nippon Chemical The light-reflective anisotropic conductive adhesive of Example 2 was prepared by uniformly mixing 5.00 parts by mass with Kogyo Co., Ltd.).
- light-reflective insulating particles titanium dioxide powder having an average particle size of 0.5 ⁇ m (KR-380, Titanium Industry Co., Ltd.)
- conductive particles gold-coated resin conductive particles having an average particle size of 5 ⁇ m (particles obtained by electroless
- Comparative Example 4 An anisotropic conductive adhesive was prepared by repeating the same operation as in Example 4 except that the light-reflective insulating particles were not used.
- the obtained anisotropic conductive adhesives of Example 2 and Comparative Example 4 were applied to a ceramic white plate so as to have a dry thickness of 100 ⁇ m, and heated at 200 ° C. for 1 minute to be cured. About this hardened
- the total luminous flux is desired to be practically 300 mlm or more
- the light-reflective anisotropic conductive adhesive of Example 2 showed a reflectance exceeding 300 mlm, whereas the anisotropic conductive of Comparative Example 4 The adhesive did not show reflectivity above 300 mlm.
- thermosetting resin composition of the present invention and the light-reflective anisotropic conductive adhesive containing the same as an insulating adhesive component include an anisotropic conductive adhesive for a light-emitting element such as a light-emitting diode (LED) element on a wiring board.
- a light-emitting element such as a light-emitting diode (LED) element on a wiring board.
- LED light-emitting diode
- the thermosetting resin composition and the light-reflective anisotropic conductive adhesive of the present invention are useful when LED chips are flip-chip mounted.
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- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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CN201380056560.2A CN104736591A (zh) | 2012-10-30 | 2013-10-30 | 热固性树脂组合物、光反射性各向异性导电粘接剂及发光装置 |
KR1020157005900A KR102139124B1 (ko) | 2012-10-30 | 2013-10-30 | 열경화성 수지 조성물, 광반사성 이방성 도전 접착제 및 발광 장치 |
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TWI556478B (zh) | 2014-06-30 | 2016-11-01 | 億光電子工業股份有限公司 | 發光二極體裝置 |
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JP6623121B2 (ja) * | 2016-06-08 | 2019-12-18 | デクセリアルズ株式会社 | 光硬化性樹脂組成物、並びに画像表示装置、及びその製造方法 |
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JP2012180489A (ja) * | 2011-03-03 | 2012-09-20 | Nippon Steel Chem Co Ltd | エポキシシリコーン樹脂及びそれを用いた硬化性樹脂組成物 |
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WO2012124724A1 (ja) * | 2011-03-16 | 2012-09-20 | ソニーケミカル&インフォメーションデバイス株式会社 | 光反射性異方性導電接着剤及び発光装置 |
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TW201430067A (zh) | 2014-08-01 |
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