WO2011055784A1 - Système amorceur de thermopolymérisation et composition adhésive - Google Patents

Système amorceur de thermopolymérisation et composition adhésive Download PDF

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WO2011055784A1
WO2011055784A1 PCT/JP2010/069693 JP2010069693W WO2011055784A1 WO 2011055784 A1 WO2011055784 A1 WO 2011055784A1 JP 2010069693 W JP2010069693 W JP 2010069693W WO 2011055784 A1 WO2011055784 A1 WO 2011055784A1
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adhesive composition
polymerization initiator
composition according
group
component
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PCT/JP2010/069693
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English (en)
Japanese (ja)
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晋 川上
永井　朗
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日立化成工業株式会社
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Priority to CN201080050092.4A priority Critical patent/CN102597044B/zh
Priority to KR1020127014112A priority patent/KR101403846B1/ko
Publication of WO2011055784A1 publication Critical patent/WO2011055784A1/fr

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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
    • C08G59/68—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 catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C08F4/34—Per-compounds with one peroxy-radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • C08G65/105—Onium 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • 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
    • C08K5/02—Halogenated hydrocarbons
    • C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings
    • 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
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • the present invention relates to a thermal polymerization initiator system and an adhesive composition.
  • an anisotropic conductive adhesive in which conductive particles are dispersed in the adhesive is used.
  • COG in which the semiconductor silicon chip is directly mounted on the substrate is performed instead of the conventional wire bond, and an anisotropic conductive adhesive is also applied here.
  • a cationic polymerization initiator for example, a polymerization initiator of a cationic polymerizable substance mainly composed of a sulfonium salt represented by the following general formula (II) has been proposed (Patent Document 1).
  • Ra represents any of hydrogen, methyl group, acetyl group, methoxycarbonyl group, ethoxycarbonyl group, benzyloxycarbonyl group, benzoyl group, phenoxycarbonyl group, and 9-fluorenylmethoxycarbonyl group.
  • R b and R c are each independently hydrogen, halogen, or a C 1 -C 4 alkyl group
  • R d is a C 1 -C 4 alkyl group
  • Q is an o-nitrobenzyl group, m- A nitrobenzyl group, a dinitrobenzyl group, a trinitrobenzyl group, an ⁇ -naphthylmethyl group, or a ⁇ -naphthylmethyl group is shown.
  • X is SbF 6 , AsF 6 , PF 6 , or BF 4 . ]
  • Patent Document 2 As a polymerization initiator capable of curing an epoxy resin in a short time by heating, a cationic polymerization initiator containing a sulfonium salt represented by the following general formula (III) or the following general formula (IV) has been proposed.
  • Patent Document 2 a cationic polymerization initiator containing a sulfonium salt represented by the following general formula (III) or the following general formula (IV) has been proposed.
  • R e represents a hydrogen atom, an alkyl group, a halogen atom, a carboxyl group or an alkoxycarbonyl group
  • R f represents an alkyl group
  • R g represents an optionally substituted phenyl group or a substituted group.
  • X represents SbF 6 , AsF 6 , PF 6 or BF 6 .
  • R h represents a hydrogen atom, an alkyl group, a halogen atom, a hydroxyl group, an alkoxy group, a carboxyl group or an alkanoyl group
  • R i represents an alkyl group
  • R j represents an alkenyl group
  • ⁇ - An alkylbenzyl group, an ⁇ , ⁇ -dialkylbenzyl group, an ⁇ -phenylbenzyl group or a fluorenyl group is represented
  • X represents SbF 6 , AsF 6 , PF 6 or BF 4 .
  • the polymerization initiator described in Patent Document 1 or 2 is selected as a sulfonium salt having a structure in which a leaving group (—Q, —CH 2 R g or R j ) is easily eliminated, so that It is considered that it is intended to achieve curing or curing in a short time.
  • the leaving group is considered to be eliminated by a cationic SN1 reaction or SN2 reaction.
  • thermal polymerization type and a photopolymerization type are known.
  • a thermal polymerization initiator system is required to have characteristics that generally trade off between low-temperature curability and storage stability.
  • Patent Document 1 or 2 uses the sulfonium salt, it is preserved when combined with a monomer having a high cationic polymerizability such as an alicyclic epoxy compound, an oxetane compound, or a vinyl ether compound. There is a problem that the curing reaction proceeds.
  • patent document 1 has description that it is excellent in storage stability, the storage conditions are "under light-shielding and 10 degrees C or less", and it cannot necessarily say that storage stability is enough.
  • the present invention has been made in view of the above circumstances, and can be bonded at a low temperature in a short time, has excellent connection reliability, and has excellent storage stability, and the production of the adhesive composition. It is an object to provide a useful thermal polymerization initiator system.
  • the present inventors have combined a iodonium salt compound represented by the following general formula (I) with a radical polymerization initiator, whereby a glycidyl ether compound as a polymerizable substance, It has been found that the curability at low temperature and the practical storage stability can be made compatible even when any of the alicyclic epoxy compound, the oxetane compound and the vinyl ether compound is used, and the present invention has been completed.
  • the present invention provides an initiator system described in the following (1) to (6) and an adhesive composition described in the following (7) to (17).
  • a thermal polymerization initiator system comprising (A) an iodonium salt compound represented by the following general formula (I) and (B) a radical polymerization initiator.
  • R 1 and R 2 each independently represents a substituted or unsubstituted aryl group, and Y ⁇ represents an anion residue.
  • Y ⁇ is SbF 6 ⁇
  • P (R 6 ) a (F) 6-a ] ⁇ (wherein R 6 is an alkyl group in which at least a part of hydrogen atoms are substituted with fluorine atoms)
  • A represents an integer of 0 to 5.
  • a is an integer of 2 or more, a plurality of R 6 may be the same or different from each other), B (C 6 F 5 ) 4 - or C (CF 3 SO 2) 3 - thermal-polymerization initiator system according to a above (1).
  • the radical polymerization initiator is an organic peroxide.
  • the thermal polymerization initiator system according to any one of (1) to (4) which is used for curing a cationically polymerizable substance.
  • the thermal polymerization initiator system according to any one of (1) to (5) which is used for curing by heating.
  • An adhesive composition comprising (A) an iodonium salt compound represented by the following general formula (I), (B) a radical polymerization initiator, and (C) a cationic polymerizable substance.
  • R 1 and R 2 each independently represents a substituted or unsubstituted aryl group, and Y ⁇ represents an anion residue.
  • Y ⁇ represents SbF 6 ⁇
  • P (R 6 ) a (F) 6-a ] ⁇ (wherein R 6 is an alkyl group in which at least a part of hydrogen atoms are substituted with fluorine atoms)
  • A represents an integer of 0 to 5.
  • the iodonium salt compound represented by the above general formula (I) is, for example, a cationic SN1 reaction or SN2 reaction as compared with the sulfonium salt described in Patent Document 1 or 2. Elimination of substituents due to. Therefore, when the iodonium salt compound represented by the general formula (I) is used alone without being combined with the radical polymerization initiator, curing at a low temperature (100 to 170 ° C.) and in a short time (within 10 seconds) It becomes difficult.
  • an initiator system capable of curing at a low temperature in a short time can be obtained by using the iodonium salt compound, which is difficult to cure at a low temperature in a short time alone, in combination with a radical polymerization initiator. I found it. The reason why such an initiator system is obtained is not necessarily clear, but it is considered that the radical generated from the radical polymerization initiator induces the sulfonium salt compound or the iodonium salt compound.
  • an adhesive composition that can be bonded at a low temperature and in a short time, has excellent connection reliability, and has excellent storage stability, and an initiator system useful for producing the adhesive composition. Can do.
  • 6 is a graph showing differential scanning calorimetry results of Examples 1 and 2 and Comparative Example 1. It is a graph which shows the differential scanning calorimetry result of Example 3 and Comparative Example 2. It is a graph which shows the differential scanning calorimetry result of Example 4 and Comparative Example 3. It is a graph which shows the differential scanning calorimetry result of Example 5 and Comparative Example 4.
  • 6 is a graph showing the relationship between the curing temperature and the curing rate of the film adhesive compositions of Examples 1 to 4 obtained in a curing rate measurement test. 6 is a graph showing the relationship between the curing temperature and the curing rate of the film-like adhesive compositions of Comparative Examples 1 to 8 obtained in the curing rate measurement test.
  • 6 is a graph showing the relationship between the curing temperature and the curing rate of the film-like adhesive compositions of Comparative Examples 9 to 11 obtained in the curing rate measurement test.
  • 6 is a graph showing the relationship between the elapsed time and the curing rate of the film-like adhesive compositions of Examples 1 to 4 obtained in a storage stability test.
  • 6 is a graph showing the relationship between the elapsed time and the curing rate of the film-like adhesive compositions of Comparative Examples 1 to 8 obtained in the storage stability test.
  • 6 is a graph showing the relationship between the elapsed time and the curing rate of the film-like adhesive compositions of Comparative Examples 9 to 11 obtained in the storage stability test.
  • the initiator system includes (A) an iodonium salt compound represented by the general formula (I) (hereinafter sometimes referred to as “component (A)”), and (B) a radical polymerization initiator (hereinafter referred to as “polymerization initiator”). In some cases, it is referred to as “component (B)”).
  • component (A) an iodonium salt compound represented by the general formula (I)
  • component (B) a radical polymerization initiator
  • it is referred to as “component (B)”.
  • each of R 1 and R 2 independently represents a substituted or unsubstituted aryl group, and Y ⁇ represents an anion residue.
  • aryl group examples include aryl groups having 6 to 12 carbon atoms. More specific examples include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. These may have a substituent, and the substitution position of the substituent is not particularly limited, and may be any position.
  • each group described above may have include, for example, alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, and a hexyl group.
  • alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, and a hexyl group.
  • Aryl groups such as phenyl and naphthyl groups; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; alkoxycarbonyl groups such as acetoxy, propionyloxy, decylcarbonyloxy, and dodecylcarbonyloxy; Examples thereof include ester groups such as carbonyl group, ethoxycarbonyl group and benzoyloxy group; halogen atoms such as fluorine, chlorine, bromine and iodine; cyano group, nitro group and hydroxy group.
  • the substitution position of these substituents is not particularly limited and may be any position.
  • anion residue examples include monovalent counter anions such as BF 4 ⁇ , SbF 6 ⁇ , AsF 6 ⁇ , [P (R 6 ) a (F) 6-a ] ⁇ (wherein R 6 represents a hydrogen atom An alkyl group at least partially substituted with a fluorine atom, and a represents an integer of 0 to 5.
  • a plurality of R 6 may be the same or different from each other B (C 6 F 5 ) 4 ⁇ , Ga (C 6 F 5 ) 4 ⁇ , Ga (C 6 F 5 ) 2 F 2 ⁇ , Ga (C 6 F 5 ) F 3 ⁇ , C (CF 3 SO 2 ) 3 — and the like can be mentioned.
  • R 6 is preferably an alkyl group in which 80% or more of hydrogen atoms are substituted with fluorine atoms, and 90% or more of hydrogen atoms are preferred. Is more preferably an alkyl group substituted with a fluorine atom, and even more preferably a linear or branched perfluoroalkyl group.
  • the anion residue preferably has low nucleophilicity. Therefore, as the anion residue, SbF 6 ⁇ , [P (R 6 ) a (F) 6-a ] ⁇ (wherein R 6 is an alkyl group in which at least a part of hydrogen atoms are substituted with fluorine atoms) A represents an integer of 0 to 5. When a is an integer of 2 or more, a plurality of R 6 may be the same or different from each other), B (C 6 F 5 4 ⁇ , C (CF 3 SO 2 ) 3 — is preferable, and SbF 6 ⁇ , B (C 6 F 5 ) 4 ⁇ , and C (CF 3 SO 2 ) 3 — are more preferable. When the nucleophilicity of the anion residue is low, the growth reaction rate of the cationic polymerizable compound is high, and the polymerization occurs at a low temperature and in a short time.
  • iodonium salt compound a diaryl iodonium salt compound in which R 1 and R 2 are substituted or unsubstituted aryl groups is preferable.
  • An initiator system containing such an iodonium salt compound is further excellent in storage stability and low temperature fast curability.
  • iodonium salt compounds include diphenyliodonium arsenic hexafluoride, di (4-chlorophenyl) iodonium arsenic hexafluoride, di (4-bromophenyl) iodonium arsenic hexafluoride, phenyl (4-methoxyphenyl) iodonium Arsenic fluoride, UVE series manufactured by General Electric, FC series manufactured by Minnesota Mining and Manufacturing, UV-9310C (counter anion: SbF 6 ⁇ ) manufactured by Toshiba Silicone, and Photoinitiator 2074 manufactured by Rhône-Poulenc (Counter anion: (C 6 F 5 ) 4 B ⁇ ).
  • the component (A) one type of iodonium salt compound may be used alone, or two or more types may be used in combination.
  • the component (A) has a function as a cationic polymerization initiator.
  • the component (A) preferably exhibits activity at a temperature of 140 to 250 ° C. from the viewpoint of storage stability, and gives a peak temperature of 140 to 250 ° C. in differential scanning calorimetry for a mixture with a glycidyl ether type epoxy compound. Those are more preferred.
  • component (B) conventionally known peroxides and azo compounds can be used, and organic peroxides are preferable from the viewpoint of further excellent storage stability and low-temperature rapid curing.
  • organic peroxide examples include diacyl peroxide, peroxydicarbonate, peroxyester, peroxyketal, dialkyl peroxide, hydroperoxide, and silyl peroxide. Of these, peroxyesters and diacyl peroxides are preferred because of their good stability and reactivity.
  • the peroxyester has a structure represented by —C ( ⁇ O) —O—O—
  • the diacyl peroxide is —C ( ⁇ O) —O—O—C ( ⁇ O) —. It has the structure represented.
  • a peroxyester or diacyl peroxide having a 1 minute half-life temperature of 80 to 170 ° C. and a molecular weight of 180 to 1000 is more preferable. Such an organic oxide provides an initiator system that is further excellent in storage stability and low-temperature rapid curability.
  • component (B) examples include cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxynoedeca Noate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexano 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxyneoheptanoate, t-amylperoxy-2-ethylhexanoate, di-t-butyl
  • peroxyesters having a 1-minute half-life temperature of 80 to 170 ° C. and a molecular weight of 180 to 1000 include 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy). ) Hexane and the like.
  • diacyl peroxide having a 1 minute half-life temperature of 80 to 170 ° C. and a molecular weight of 180 to 1000 include lauroyl peroxide.
  • One radical polymerization initiator may be used alone, or two or more radical polymerization initiators may be used in combination.
  • the content ratio of the component (B) in the initiator system according to the present embodiment is preferably 25% by mass or more and more preferably 50% by mass or more based on the total amount of the component (A).
  • (B) By making the content rate of a component in the said range, the initiator system which is further excellent in storage stability and low-temperature rapid curability can be obtained.
  • the content ratio of the component (B) is less than the above range, there is a tendency that the starting species of cationic polymerization is not sufficiently generated.
  • the initiator system contains an organic peroxide as the component (B), a 1 minute half-life temperature ⁇ of the organic peroxide, and a mixture of the component (A) and a glycidyl ether type epoxy compound
  • the difference ⁇ from the peak temperature ⁇ in the differential scanning calorimetry is preferably 30 to 200 ° C.
  • the initiator system comprises at least one onium selected from the group consisting of a sulfonium salt compound and an iodonium salt compound that gives a peak temperature of 140 to 250 ° C. in differential scanning calorimetry for a mixture with a glycidyl ether type epoxy compound. It may contain a salt and an organic peroxide having a half-life temperature of 80 to 170 ° C. for 1 minute. Similar to the initiator system according to the above embodiment, such an initiator system can polymerize a cationically polymerizable substance such as an epoxy compound at a low temperature in a short time and has excellent storage stability.
  • the iodonium salt compound and the organic oxide those similar to the above can be used.
  • the initiator system according to this embodiment can polymerize a cationically polymerizable substance such as an epoxy compound in a short time at a low temperature and is excellent in storage stability. Therefore, according to the initiator system according to the present embodiment, it is possible to produce an adhesive composition that can be bonded at a low temperature in a short time, has excellent connection reliability, and excellent storage stability.
  • the reason why such an effect is achieved by the combined use of the onium salt compound and the radical polymerization initiator is not necessarily clear, but since the onium salt compound is excellent in stability, the storage stability is improved, and the radical polymerization initiator is obtained. It is considered that low-temperature rapid curing can be realized because the radicals generated from the liquid induce the generation of cationic species by decomposition of the onium salt compound.
  • the adhesive composition according to the present embodiment includes (A) an iodonium salt compound represented by the general formula (I), (B) a radical polymerization initiator, (C) a cationic polymerizable substance (hereinafter referred to as “ (C) component ").
  • iodonium salt compound and the radical polymerization initiator those similar to the components (A) and (B) in the above-described initiator system are used.
  • the content ratio of the component (A) in the adhesive composition according to this embodiment is preferably 0.05 to 30% by mass, and 0.1 to 15% by mass based on the total amount of the component (C). It is more preferable.
  • the content ratio of the component (A) is less than the above range, curing may be insufficient, and when it exceeds the above range, the compatibility tends to decrease.
  • the content ratio of the component (B) in the adhesive composition according to the present embodiment is preferably 25% by mass or more, and more preferably 50% by mass or more based on the total amount of the component (A).
  • (B) By making the content rate of a component in the said range, the initiator system which is further excellent in storage stability and low-temperature rapid curability can be obtained.
  • the content ratio of the component (B) is less than the above range, there is a tendency that the starting species of cationic polymerization is not sufficiently generated.
  • Examples of the component (C) include epoxy compounds, oxetane compounds, vinyl ether compounds and the like, and examples of the epoxy compounds include glycidyl ether type epoxy compounds and alicyclic epoxy compounds.
  • the (C) component cationically polymerizable substituent equivalent is preferably 43 to 1000, more preferably 50 to 800, and even more preferably 73 to 600.
  • the cation polymerizable substituent equivalent means the average molecular weight of one molecule of the cation polymerizable compound contained in the quotient of the cation polymerizable substituent in one molecule of the cation polymerizable compound, that is, per unit cation polymerizable substituent. Refers to average molecular weight.
  • component (C) it is preferable to use a high-purity product in which the content of impurity ions (Na + , Cl ⁇ , etc.) and hydrolyzable chlorine is reduced to 300 ppm or less, from the viewpoint of preventing corrosion.
  • the content ratio of the component (C) in the adhesive composition according to this embodiment is preferably 10 to 90% by mass, and more preferably 25 to 75% by mass based on the total amount of the adhesive composition. .
  • an adhesive composition having poor physical properties (glass transition temperature, elastic modulus, etc.) of the cured product may be obtained. May increase and the adhesive strength may decrease.
  • the glycidyl ether type epoxy compound as the component (C) is a compound having a glycidyl ether group in the molecule and can be cured by irradiation with actinic rays or heating in the presence or absence of a curing agent. Among them, those having two or more epoxy groups in one molecule are preferable because the crosslink density when cured is high.
  • the glycidyl ether type epoxy compound is not particularly limited as long as it is a compound having a glycidyl ether group, and known compounds can be used.
  • bisphenol type epoxy resins derived from epichlorohydrin and bisphenol A, bisphenol F, etc. polyglycidyl ethers, polyglycidyl esters, aromatic epoxy compounds, alicyclic epoxy compounds, cresol novolac type epoxy resins, phenols Novolac epoxy compounds such as novolac epoxy resins, glycidylamine epoxy compounds, glycidyl ester epoxy compounds, biphenyl diglycidyl ether, triglycidyl isocyanurate, polyglycidyl methacrylate, glycidyl methacrylate and vinyl monomers copolymerizable therewith And a copolymer thereof. These are used alone or in combination of two or more.
  • the (C) component alicyclic epoxy compound is a compound having an epoxy group composed of two oxygen atoms and carbon atoms constituting a cyclic hydrocarbon skeleton in the molecule, and in the presence or absence of a curing agent. Any material can be used as long as it is cured by irradiation with active light or heating. Among them, those having two or more epoxy groups in one molecule are preferable because the crosslink density when cured is high.
  • the alicyclic epoxy compound is not particularly limited as long as it is a compound having an alicyclic epoxy group, and known compounds can be used.
  • Examples thereof include cyclohexene oxide and cyclopentene oxide-containing compounds obtained by oxidizing cyclohexene and cyclopentene ring-containing compounds. More specifically, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-metadioxane, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy- 1-methylhexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy 5-methylcyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylcarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 6-methyl
  • the oxetane compound as the component (C) may be any oxetane compound having an oxetanyl group in the molecule and capable of being cured by irradiation with actinic rays or heating in the presence or absence of a curing agent.
  • a compound having two or more oxetane rings is preferable because the crosslink density when cured is high.
  • an aliphatic or alicyclic compound having 2 to 6 oxetane rings and 1 to 6 hydroxyl groups in the molecule is preferable from the viewpoint of excellent curability.
  • Examples of the oxetane compound include compounds represented by the following general formula (V).
  • R 9 represents a hydrogen atom, a fluorine atom or a monovalent hydrocarbon group
  • R 10 represents a hydrogen atom, an alkyl group or an aryl group
  • n represents an integer of 1 to 4.
  • n is 1 when R 10 is a hydrogen atom.
  • a plurality of oxygen atom bonding to R 10 may be bonded to the same carbon atom of R 10 may be mutually bonded to different carbon atoms of R 10.
  • oxetane compound 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene, 4,4′-bis [(3-oxetanyl-n-butoxy) methyl] biphenyl
  • examples include 3-ethyl-3 ⁇ [(3-ethyloxetane-3-yl) methoxy] methyl ⁇ oxetane, 3-ethyl 3-hydroxymethyloxetane, 2-ethylhexyloxetane and the like.
  • the vinyl ether compound as component (C) may be any compound having a vinyl ether group in the molecule and capable of being cured by irradiation with actinic rays or heating in the presence or absence of a curing agent. Among them, those having two or more epoxy groups in one molecule are preferable because the crosslink density when cured is high.
  • Examples of the vinyl ether compound include compounds represented by the following general formula (VI).
  • R 11 represents an alkyl group or an aryl group
  • n represents an integer of 1 to 4.
  • a plurality of oxygen atoms bonded to R 11 may be bonded to the same carbon atom of R 11 may be mutually bonded to different carbon atoms of R 11.
  • vinyl ether compound examples include 1,4-butanediol divinyl ether, cyclohexane dimethanol divinyl ether, diethylene glycol divinyl ether, and triethylene glycol divinyl ether.
  • one type may be used alone, or two or more types may be used in combination.
  • the adhesive composition according to this embodiment can be cured by heating.
  • the heating temperature is preferably 40 to 180 ° C., more preferably 50 to 150 ° C., and the heating time is preferably 0.1 second to 10 hours, more preferably 1 second to 1 hour.
  • the heating temperature is less than 40 ° C.
  • the curing rate is slow, and when it exceeds 180 ° C., unwanted side reactions may progress and connection reliability may be lowered.
  • the heating time is less than 0.1 seconds, the curing reaction may not proceed. If the heating time exceeds 10 hours, the productivity of the cured product decreases, and an undesirable side reaction proceeds and connection reliability decreases. There is.
  • the adhesive composition according to this embodiment contains the initiator system according to the above-described embodiment. That is, when the adhesive composition according to this embodiment is cured by heating, radicals generated from the radical polymerization initiator (B) component induce the onium salt compound (A) component. it is conceivable that. Therefore, it is preferable that the adhesive composition according to this embodiment does not substantially contain a radical scavenger. Further, the content of the radically polymerizable vinyl compound is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, based on the total amount of the adhesive composition, and 0 to 3% by mass. Is more preferably 0 to 1% by mass, particularly preferably 0% by mass.
  • the adhesive composition according to this embodiment may further contain conductive particles.
  • the conductive particles include metal particles such as Au, Ag, Ni, Cu, and solder, and carbon.
  • non-conductive glass, ceramic, plastic, or the like may be used as a core, and the core, metal particles, or carbon may be coated on the core.
  • conductive particles with plastic as the core and the core coated with the above metal, metal particles or carbon, or hot-melt metal particles the contact area with the electrode increases during connection because it is deformable by heating and pressing. This is preferable because the reliability is improved.
  • fine particles with the surface of these conductive particles coated with a polymer resin or the like suppress short-circuiting due to contact between particles when the amount of conductive particles is increased, and improve insulation between electrode circuits. Therefore, it may be used alone or mixed with conductive particles as appropriate.
  • the average particle size of the conductive particles is preferably 1 to 18 ⁇ m from the viewpoint of good dispersibility and conductivity.
  • the content ratio of the conductive particles in the adhesive composition according to this embodiment is not particularly limited, but is preferably 0.1 to 30% by volume with respect to 100% by volume of the adhesive composition. More preferably, it is 1 to 10% by volume. If the content of the conductive particles is less than 0.1% by volume, the conductivity tends to be inferior, and if it exceeds 30% by volume, a short circuit may occur.
  • the “volume%” is determined based on the volume of each component before curing at 23 ° C., but the volume of each component can also be calculated by converting mass using specific gravity. In addition, do not dissolve or swell the component in a graduated cylinder, etc., but put in a suitable solvent (water, alcohol, etc.) that wets the component well. You can ask for it.
  • a corrosion inhibitor made of a metal hydroxide or a metal oxide can be added and mixed for the purpose of preventing corrosion of the adherend. More specifically, the corrosion inhibitor includes aluminum hydroxide, magnesium hydroxide, calcium hydroxide, silicon oxide, aluminum oxide, magnesium oxide, antimony oxide, tin oxide, titanium oxide, manganese oxide, and zirconium oxide. At least one selected from the above is preferred. Furthermore, from the viewpoint of dispersion in the adhesive composition, high adhesion to the adherend, and corrosion resistance of the adherend, when the corrosion inhibitor is in the form of particles, the particle size is 10 ⁇ m or less. Is preferred.
  • the content of the corrosion inhibitor in the adhesive composition according to this embodiment is preferably 0.1 to 60% by mass, more preferably 1 to 30% by mass, based on the total amount of the component (A). preferable.
  • the content of the corrosion inhibitor is less than 0.1% by mass, the corrosion prevention effect is not sufficiently obtained, and when it exceeds 60% by mass, the dispersibility is lowered and the connection reliability of the adhesive composition may be lowered. is there.
  • the adhesive composition according to this embodiment may further contain a chain ether compound or a cyclic ether compound.
  • a chain ether compound or a cyclic ether compound may be contained as the component (C)
  • the curing behavior of the alicyclic epoxy compound can be easily and reliably controlled by further containing a chain or cyclic ether compound.
  • the chain or cyclic ether compound is not particularly limited as long as it has two or more ether bonds in one molecule, and a known one can be used.
  • the chain ether compound polyethylene glycols such as diethylene glycol, triethylene glycol, and tetraethylene glycol; derivatives obtained by functionalizing terminal hydroxyl groups of polyethylene glycols with ether bonds or ester bonds; ethylene oxide, propylene oxide, cyclohexene oxide, etc.
  • cyclic ether compounds include 12-crown-4-ether, 14-crown-4-ether, 15-crown-5-ether, 18-crown-6-ether, 21-crown-7-ether, 24- Crown-8-ether, 30-crown-7-ether, benzo-18-crown-6-ether, dibenzo-18-crown-6-ether, tribenzo-18-crown-6-ether, cyclized products of polyethylene glycols And cyclized products of polymers of epoxy compounds. These can be used alone or in combination.
  • cyclic ether compounds are preferable from the viewpoint of reaction control ability, and 12-crown-4-ether, 14-crown-4-ether, 15-crown-5-ether, 18-crown-6-ether, 21- Crown-7-ether, 24-crown-8-ether, 30-crown-7-ether, benzo-18-crown-6-ether, dibenzo-18-crown-6-ether, tribenzo-18-crown-6- Ether is more preferred.
  • the content of the chain or cyclic ether compound in the adhesive composition according to the present embodiment is preferably 0.005 to 10 mol%, and 0.01 to 5 mol% with respect to the component (A). More preferably. If the content of the chain or cyclic ether compound is less than 0.005 mol%, high adhesive strength is difficult to obtain, and if it exceeds 20 mol%, curing is prohibited, and as a result, a low cross-linking density may occur.
  • the adhesive composition according to this embodiment has various known additives such as inorganic fillers, reinforcing materials, colorants, and stabilizers (thermal stabilizers, weather resistance) as long as the effects of the present invention are not impaired.
  • Property improvers, etc. extenders, viscosity modifiers, terpene phenol copolymers, terpene resins, rosin derivatives, alicyclic hydrocarbon resins, tackifiers, flame retardants, UV absorbers, antioxidants Agents, anti-discoloring agents, antibacterial agents, antifungal agents, anti-aging agents, antistatic agents, plasticizers, lubricants, foaming agents, mold release agents and the like.
  • the colorant examples include direct dyes, acid dyes, basic dyes, metal complex dyes, inorganic pigments such as carbon black and mica, and coupling azo, condensed azo, anthraquinone, thioindigo, and dioxazone. And organic pigments such as phthalocyanine.
  • the stabilizer include hindered phenol-based, hydrazine-based, phosphorus-based, benzophenone-based, benzotriazole-based, and oxalic acid anilide-based compounds.
  • the inorganic filler glass fiber, asbestos fiber, carbon fiber, silica fiber, alumina fiber, zirconia fiber, boron nitride fiber, silicon nitride fiber, basic magnesium sulfate fiber, boron fiber, stainless steel fiber, aluminum Inorganic and metal fibers such as titanium, copper, brass, magnesium, etc., metal powders such as copper, iron, nickel, zinc, tin, lead, stainless steel, aluminum, gold and silver, wood powder, aluminum silicate, talc, clay, Carbonates, sulfates, phosphates, borates, borosilicates, aluminosilicates, titanates, basic sulfates, basic carbonates and other basic salts, glass hollow spheres, glass flakes, etc. Examples thereof include glass materials, silicon carbide, aluminum nitride, mullite, cordierite and the like.
  • the adhesive composition according to the present embodiment may appropriately contain various polymers for the purpose of thickening or forming a film.
  • a polymer to be contained a known polymer can be used without limitation as long as it does not significantly inhibit the curing of the component (C).
  • examples of such polymers include phenoxy resins, polymethacrylates, polyacrylates, polyesters, polyvinyl butyrals, SBS (styrene butadiene styrene block copolymer) and its epoxy modified products, SEBS (styrene ethylene butylene styrene block copolymer). Polymer) and modified products thereof. These can be used alone or in admixture of two or more.
  • these polymers may contain siloxane bonds or fluorine substituents.
  • These can be suitably used as an adhesive composition as long as the resins to be mixed are completely compatible with each other or microphase separation occurs and the mixture becomes cloudy.
  • Denka butyral 3000-1, 3000-2, 3000-4, 3000-K, 4000-2, 5000-A, 5000-D product name of Denki Kagaku Kogyo Co., Ltd.
  • It is preferable to contain a film-forming polymer such as
  • the weight average molecular weight of the polymer is not particularly limited, but is preferably 5000 to 150,000, and more preferably 10,000 to 80,000. If the weight average molecular weight is less than 5,000, the film formability tends to be inferior, and if it exceeds 150,000, the compatibility with other components tends to deteriorate.
  • the content of the polymer in the adhesive composition according to this embodiment is preferably 20 to 320% by mass and more preferably 50 to 150% by mass with respect to 100 parts by mass of the component (C).
  • the content of the polymer is less than 20% by mass or exceeds 320% by mass, the fluidity and adhesiveness of the adhesive composition tend to decrease.
  • the adhesive composition according to this embodiment can be used in the form of a paste when it is liquid at room temperature.
  • a solid at room temperature it may be heated and used, or may be made into a paste using a solvent.
  • Solvents that can be used are not particularly limited as long as they are not reactive with the adhesive composition and additives and exhibit sufficient solubility, but have a boiling point of 50 to 150 ° C. at normal pressure. Those are preferred.
  • the solvent has a boiling point of less than 50 ° C., it may volatilize when left at room temperature, and its use in an open system is restricted.
  • the adhesive composition according to the present embodiment can be bonded by using heating and pressurization together.
  • the heating temperature is not particularly limited, but a temperature of 50 to 190 ° C. is preferable.
  • the pressure is not particularly limited as long as it does not damage the adherend, but it is generally preferably 0.1 to 30 MPa. These heating and pressurization are preferably performed in the range of 0.5 to 120 seconds.
  • the adhesive composition according to the present embodiment can be used as an adhesive for different types of adherends having different thermal expansion coefficients. Specifically, it is used as a semiconductor element adhesive material typified by anisotropic conductive adhesive, silver paste, silver film, etc., circuit connection material, CSP elastomer, CSP underfill material, LOC tape, etc. Can do.
  • the anisotropic conductive film is disposed between the electrodes facing each other on the substrate. And heating and pressurizing. By this method, contact between both electrodes and adhesion between the substrates can be obtained and connection with the electrodes can be performed.
  • Substrates for forming electrodes include inorganic materials such as semiconductors, glass and ceramics, polyimide substrates represented by TCP, FPC and COF, substrates having electrodes formed on films such as polycarbonate, polyester and polyethersulfone, and prints. Each combination of these composites such as a wiring board can be applied.
  • DSC peak temperature means a peak temperature in differential scanning calorimetry for a mixture with a glycidyl ether type epoxy compound.
  • Photoinitiator 2074 (product name of Rhodia, 4-methylphenyl [4- (1-methylethyl) phenyl] iodonium tetrakis (pentafluorophenyl) borate) as component (A), and perhexa25O (product of NOF Corporation) as component (B) Name, 2,5-dimethyl-2,5-di (ethylhexanoylperoxy) hexane, purity 50%, 1 minute half-life temperature 119 ° C), glycidyl ether type epoxy compound YL980 (Japan Epoxy Resin) as component (C)
  • the product name was bisphenol F type epoxy resin), and the binder was phenoxy resin (YP-70, product name manufactured by Tohto Kasei Co., Ltd.).
  • a nickel layer of 0.2 ⁇ m is provided and the outside of this nickel layer , It was used to create an average particle diameter of 3 ⁇ m having a metal thickness 0.02 [mu]
  • the components (A) to (C) and the binder are blended at a weight ratio shown in Table 1, and 8% by volume of conductive particles are further dispersed and applied to a PET resin film having a thickness of 40 ⁇ m using a coating apparatus.
  • the film adhesive composition with an adhesive layer thickness of 20 ⁇ m was obtained by hot air drying at 70 ° C. for 5 minutes.
  • Example 2 As component (B), Perroyl L (Nissho Corporation product name, dilauroyl peroxide, purity 98%, half-life temperature 116 ° C.) was used in place of Perhexa 25O.
  • the film adhesive composition was obtained by the method. Table 1 shows the mixing ratio of each component.
  • Example 3 (Example 3) (C)
  • YL980 alicyclic epoxy compound Cexaloid GT401 (product name of Daicel Chemical Industries, Ltd., epoxidized butanetetracarboxylic acid tetrakis- (3-cyclohexenylmethyl) modified ⁇ -caprolactone)
  • Table 1 shows the mixing ratio of each component.
  • Example 4 Example except that oxetane compound OXT-121 (product name of Toagosei Co., Ltd., 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene) was used as component (C) instead of YL980 2 was used to obtain a film adhesive composition.
  • Table 1 shows the mixing ratio of each component.
  • Example 5 As a component (C), a film-like adhesive composition was obtained in the same manner as in Example 2 except that YL980 and vinyl ether compound CHDVE (Nippon Carbide Industries, Ltd., product name, cyclohexanedimethanol divinyl ether) were used in combination. Table 1 shows the mixing ratio of each component.
  • Example 1 A film adhesive composition was obtained in the same manner as in Example 2 except that the component (B) was not used. Table 2 shows the mixing ratio of each component.
  • Example 5 A film adhesive composition was obtained in the same manner as in Example 2 except that the component (A) was not used. Table 2 shows the mixing ratio of each component.
  • Comparative Example 7 Comparative Example 5 except that oxetane compound OXT-121 (product name of Toagosei Co., Ltd., 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene) was used as the component (C) instead of YL980
  • OXT-121 product name of Toagosei Co., Ltd., 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene
  • Table 2 shows the mixing ratio of each component.
  • Comparative Example 11 Comparative Example 9 except that oxetane compound OXT-121 (product name of Toagosei Co., Ltd., 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene) was used as the component (C) instead of YL980.
  • OXT-121 product name of Toagosei Co., Ltd., 1,4-di [(3-oxetanyl-n-butoxy) methyl] benzene
  • a film-like adhesive composition was obtained by the same method. Table 2 shows the mixing ratio of each component.
  • PI2074 indicates Photoinitiator 2074.
  • the mixing ratio of each component is shown as parts by mass.
  • FIG. 1 shows the differential scanning calorimetry results of Comparative Example 2
  • FIG. 3 shows the differential scanning calorimetry results of Example 4 and Comparative Example 3 using OXT-121 which is oxetane as Component C, and glycidyl ether type as Component C.
  • FIG. 4 shows the results of differential scanning calorimetry in Example 5 and Comparative Example 4 using YL980, which is epoxy, and CHDVE, which is vinyl ether.
  • Example 1 In Examples 1 to 5 containing an onium salt compound and a radical polymerization initiator, an exothermic peak was observed near 100 ° C. and at a low temperature. In Example 2 using Parroyl L having a lower half-life temperature of 1 minute than that in Example 1, a relatively exothermic peak was observed on the low temperature side. On the other hand, in Comparative Examples 1 to 4 containing no radical polymerization initiator, the exothermic peak was relatively high.
  • Examples 1 to 5 containing an onium salt compound and a radical polymerization initiator a high curing rate was exhibited at a low temperature.
  • Comparative Examples 1 to 4 containing no radical polymerization initiator curing hardly proceeded at low temperatures.
  • Comparative Examples 5 to 8 containing no onium salt compound curing did not proceed. That is, it can be seen that the onium salt compound and the radical polymerization initiator each show high curability at low temperatures when they are combined, although they are low in activity with respect to the cationic polymerizable substance.
  • Comparative Examples 9 to 11 using the onium salt compound SI-60 that does not correspond to the component (A) of the present invention the composition was cured at a low temperature even without a radical polymerization initiator.
  • the combination of the onium salt compound (A), the radical polymerization initiator (B) and the cationic polymerizable substance (C) achieves both low-temperature fast curability and storage stability. It became clear that it was an excellent effect system.
  • An IC chip (outside 1.7 mm ⁇ 17.2 mm, thickness 0.55 mm, bump size 50 ⁇ m ⁇ 50 ⁇ m, bump pitch 50 ⁇ m) under the mounting conditions (temperature and time) shown in Table 3 is 80 MPa (bump area conversion) ) It was mounted by heating and pressing under load. Moreover, the film adhesive composition after a storage stability test was similarly mounted.
  • connection resistance A resistance value (maximum value among 14 terminals measured) between adjacent circuits of the connection body produced as described above was measured. The obtained results are shown in Table 3.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
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  • Epoxy Resins (AREA)
  • Wire Bonding (AREA)
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  • Non-Insulated Conductors (AREA)

Abstract

L'invention porte sur un système initiateur de thermopolymérisation qui comprend (A) un sel d'iodonium représenté par la formule générale (I) et (B) un amorceur de polymérisation radicalaire. Dans la formule générale (I), R1 et R2 représentent chacun indépendamment aryle substitué ou non substitué ; et Y- est un reste anionique.
PCT/JP2010/069693 2009-11-05 2010-11-05 Système amorceur de thermopolymérisation et composition adhésive WO2011055784A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103081236B (zh) * 2010-08-06 2016-03-09 旭化成电子材料株式会社 各向异性导电性粘接膜及固化剂
JP2013187375A (ja) * 2012-03-08 2013-09-19 Hitachi Chemical Co Ltd 半導体装置用接着フィルム、半導体装置の製造方法及びそれを用いた半導体装置
JP2013187376A (ja) * 2012-03-08 2013-09-19 Hitachi Chemical Co Ltd 半導体装置用接着フィルム、半導体装置の製造方法及びそれを用いた半導体装置
JP6044261B2 (ja) * 2012-10-22 2016-12-14 日立化成株式会社 異方導電性接着剤組成物
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JPWO2016021535A1 (ja) * 2014-08-08 2017-05-18 横浜ゴム株式会社 導電性組成物、太陽電池セルおよび太陽電池モジュール
WO2016060191A1 (fr) * 2014-10-17 2016-04-21 太陽インキ製造株式会社 Film sec et carte de circuits imprimé souple
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JP6894686B2 (ja) * 2016-09-30 2021-06-30 リンテック株式会社 粘接着剤組成物、粘接着剤、粘接着シートおよび表示体
TW202016240A (zh) * 2018-07-27 2020-05-01 日商琳得科股份有限公司 硬化性薄膜狀接著劑及裝置的製造方法
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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006096925A (ja) * 2004-09-30 2006-04-13 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2006124518A (ja) * 2004-10-29 2006-05-18 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2006265483A (ja) * 2005-03-25 2006-10-05 Kaneka Corp 熱ラジカル硬化／熱カチオン硬化併用硬化性組成物
WO2007074813A1 (fr) * 2005-12-26 2007-07-05 Kaneka Corporation Composition durcissable
JP2008013721A (ja) * 2006-07-10 2008-01-24 Kyocera Chemical Corp 硬化性樹脂組成物、表示素子用接着剤及び接着方法
JP2008291137A (ja) * 2007-05-25 2008-12-04 Kaneka Corp 硬化性組成物
JP2009513777A (ja) * 2005-10-26 2009-04-02 スリーエム イノベイティブ プロパティズ カンパニー 同時に硬化可能なハイブリッド接着剤組成物
WO2009075233A1 (fr) * 2007-12-10 2009-06-18 Kaneka Corporation Composition durcissable développable par un alcali, film mince isolant utilisant celle-ci et transistor à film mince
JP2009194359A (ja) * 2008-01-16 2009-08-27 Hitachi Chem Co Ltd 回路接続用接着フィルム、これを用いた回路部材の接続構造及び回路部材の接続方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ201589A (en) * 1981-11-02 1985-08-16 Grace W R & Co Heat activatable adhesive or sealant compositions
JP2002097443A (ja) * 2000-09-21 2002-04-02 Hitachi Chem Co Ltd 接着剤組成物及びこれを用いた回路接続材料並びに接続体
US7550097B2 (en) * 2003-09-03 2009-06-23 Momentive Performance Materials, Inc. Thermal conductive material utilizing electrically conductive nanoparticles
JP2005215443A (ja) * 2004-01-30 2005-08-11 Fuji Photo Film Co Ltd 重合性組成物及びそれを用いた画像形成材料
JP5168860B2 (ja) * 2006-09-14 2013-03-27 株式会社スリーボンド 光重合性組成物
JP2009086337A (ja) * 2007-09-28 2009-04-23 Fujifilm Corp 重合性組成物及び平版印刷版原版

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006096925A (ja) * 2004-09-30 2006-04-13 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2006124518A (ja) * 2004-10-29 2006-05-18 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2006265483A (ja) * 2005-03-25 2006-10-05 Kaneka Corp 熱ラジカル硬化／熱カチオン硬化併用硬化性組成物
JP2009513777A (ja) * 2005-10-26 2009-04-02 スリーエム イノベイティブ プロパティズ カンパニー 同時に硬化可能なハイブリッド接着剤組成物
WO2007074813A1 (fr) * 2005-12-26 2007-07-05 Kaneka Corporation Composition durcissable
JP2008013721A (ja) * 2006-07-10 2008-01-24 Kyocera Chemical Corp 硬化性樹脂組成物、表示素子用接着剤及び接着方法
JP2008291137A (ja) * 2007-05-25 2008-12-04 Kaneka Corp 硬化性組成物
WO2009075233A1 (fr) * 2007-12-10 2009-06-18 Kaneka Corporation Composition durcissable développable par un alcali, film mince isolant utilisant celle-ci et transistor à film mince
JP2009194359A (ja) * 2008-01-16 2009-08-27 Hitachi Chem Co Ltd 回路接続用接着フィルム、これを用いた回路部材の接続構造及び回路部材の接続方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013137238A1 (fr) * 2012-03-16 2013-09-19 株式会社ダイセル Composition durcissable et produit durci à base de celle-ci
WO2022085741A1 (fr) * 2020-10-22 2022-04-28 昭和電工マテリアルズ株式会社 Film d'agent adhésif pour connexion de circuit, structure de connexion et procédé de fabrication de structure de connexion

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TWI529186B (zh) 2016-04-11
CN102597044A (zh) 2012-07-18
TW201412800A (zh) 2014-04-01
TWI425014B (zh) 2014-02-01
CN104017173A (zh) 2014-09-03
KR101403846B1 (ko) 2014-06-03
JP2014139328A (ja) 2014-07-31
JP5892192B2 (ja) 2016-03-23
CN104017173B (zh) 2017-04-12
JP2011116977A (ja) 2011-06-16
TW201134842A (en) 2011-10-16
JP5533568B2 (ja) 2014-06-25
KR20120088796A (ko) 2012-08-08

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