Classifications

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  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets
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  • 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
  • C08G59/24—Di-epoxy compounds carbocyclic
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  • 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
  • C08G59/24—Di-epoxy compounds carbocyclic
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  • 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
  • C08G59/40—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 curing agents used
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  • C08G59/40—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 curing agents used
  • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
  • C08G59/4014—Nitrogen containing compounds
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  • C08G59/40—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 curing agents used
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  • C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
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  • 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
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  • C08G59/686—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 containing nitrogen
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  • 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
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  • 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
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  • C08G65/18—Oxetanes
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Definitions

• the present invention relates to an anisotropic conductive film.
• an anisotropic conductive film in which conductive particles are dispersed in an insulating binder composition containing a polymerizable compound has been widely used.
• an anisotropic conductive film in order to achieve low temperature fast curability, an alicyclic epoxy compound having higher cationic polymerization reactivity than a general-purpose glycidyl ether compound is used as a polymerizable compound, It has been proposed to use a sulfonium salt thermal acid generator that generates protons by heat as a polymerization initiator that does not inhibit polymerization by oxygen and exhibits dark reactivity (Patent Documents 1 to 3).
• Such a conventional anisotropic conductive film containing an alicyclic epoxy compound and a sulfonium salt-based thermal acid generator has a relatively low curing temperature (for example, about 100 ° C.).
• the anisotropic conductive film as described above may be stored in a warehouse where air-conditioning is not provided, and there is a problem that the time from manufacture to actual use becomes long due to internationalization of commercial transactions. As a result, there are concerns about a decrease in storage stability (storage life) from the viewpoints of temporary sticking properties and indentations, and a decrease in connection reliability from the viewpoint of adhesion characteristics.
• the problem of the present invention is that the cationic polymerizable anisotropic conductive film using the alicyclic epoxy compound has better storage than ever before while ensuring the same curing temperature and connection reliability as before. It is to be able to realize life.
• the present inventor uses a low-polar oxetane compound in a specific ratio in addition to an alicyclic epoxy compound as a cationic polymerizable compound, and a quaternary quaternary polymerization initiator instead of a sulfonium salt-based thermal acid generator.
• a quaternary quaternary polymerization initiator instead of a sulfonium salt-based thermal acid generator.
• the present invention is an anisotropic conductive film containing a binder composition containing a film-forming component and a cationic polymerizable component, a cationic polymerization initiator, and conductive particles
• a cationic polymerization initiator is a quaternary ammonium salt thermal acid generator
• the cationic polymerizable component contains an alicyclic epoxy compound and a low polarity oxetane compound.
• the present invention also provides a connection structure in which the first electronic component and the second electronic component are anisotropically conductively connected using the anisotropic conductive film described above.
• the anisotropic conductive film of the present invention containing a binder composition containing a film-forming component and a cationic polymerizable component, a cationic polymerization initiator, and conductive particles is a quaternary ammonium as a cationic polymerization initiator.
• a salt-based thermal acid generator is used, and an alicyclic epoxy compound and a low-polar oxetane compound are contained as a cationic polymerizable component. For this reason, while ensuring the same curing temperature and connection reliability as before, it is possible to realize better storage life than ever.
• the anisotropic conductive film of the present invention contains a binder composition containing a film-forming component and a cationic polymerizable component, a cationic polymerization initiator, and conductive particles.
• the binder composition containing and holding the conductive particles contains a film forming component and a cationic polymerizable component.
• the film-forming component is a component used for forming an anisotropic conductive film into a film and is a component having film-forming ability.
• the film forming component include phenoxy resin, epoxy resin, unsaturated polyester resin, saturated polyester resin, urethane resin, butadiene resin, polyimide resin, polyamide resin, polyolefin resin, and the like. The above can be used together. Among these, a phenoxy resin can be preferably used from the viewpoints of film formability, processability, and connection reliability.
• the blending ratio of the film-forming component in the binder composition is preferably 10 to 70% by mass, more preferably 20 to 50% by mass. If it is this range, sufficient film formation ability can be exhibited.
• the cationic polymerizable component is a component that cures the anisotropic conductive film and contains an alicyclic epoxy compound and a low-polar oxetane compound.
• the blending amount of the cationically polymerizable component in the binder composition is preferably 10 to 80% by mass, more preferably 20 to 60% by mass. If it is this range, the binder composition which has a higher hardening rate can be given.
• the reason for using the alicyclic epoxy compound is to impart good low-temperature rapid curability to the anisotropic conductive film by utilizing its reactivity higher than that of a general-purpose glycidyl ether type epoxy compound.
• Preferred examples of such alicyclic epoxy compounds include those having two or more epoxy groups in the molecule. These may be liquid or solid. Specific examples include diglycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate, diepoxybicyclohexyl and the like. Among these, diglycidyl hexahydrobisphenol A, particularly diepoxybicyclohexyl, can be preferably used from the viewpoint that the light transmittance of the cured product can be ensured and the fast curability is excellent.
• a low polarity oxetane compound is used in combination with an alicyclic epoxy compound.
• a low-polar oxetane compound is an oxetane compound having a dipole moment of 3.0 d or less, has a relatively low surface tension, and can impart good leveling properties to the film of an anisotropic conductive film. It becomes possible to improve the storage life of the anisotropic conductive film.
• a low polarity oxetane compound has the effect
• Examples of such low polarity oxetane compounds include 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3-hydroxymethyloxetane, di [1-ethyl (3-oxetanyl)] methyl ether, 4,4'-bis [(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl and the like.
• the blending ratio of the alicyclic epoxy compound and the low polarity oxetane compound is preferably 25:75 to 60:40, more preferably 45:55 to 60:40, and particularly preferably 50:50 to 55:45 on a mass basis. It is.
• the blending amount of the low-polar oxetane compound is higher than this range, the reaction start temperature and the reaction end temperature tend to increase, and conversely, when it decreases, the storage life tends to decrease. Therefore, by adjusting the blending ratio of the alicyclic epoxy compound and the low polarity oxetane compound, it is possible to control the reaction start temperature and the reaction end temperature of the anisotropic conductive film, and further, the temperature rise during the reaction.
• the reaction time can be controlled by adjusting the temperature rate and the like.
• Binder composition is bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, other epoxy resins such as their modified epoxy resin, silane coupling agent, filler, softener, acceleration as required Agents, anti-aging agents, colorants (pigments, dyes), organic solvents, ion catchers and the like.
• a (meth) acrylate compound and a radical polymerization initiator can be contained as needed.
• the (meth) acrylate compound a conventionally known (meth) acrylate monomer can be used as the (meth) acrylate compound.
• a monofunctional (meth) acrylate monomer or a bifunctional or higher polyfunctional (meth) acrylate monomer can be used as the (meth) acrylate compound.
• (meth) acrylate includes acrylate and methacrylate.
• radical polymerization initiator well-known radical polymerization initiators, such as an organic peroxide and an azobis britonitrile, can be contained.
• the anisotropic conductive film of the present invention contains conductive particles in the binder composition in order to enable anisotropic conductive connection.
• the conductive particles can be appropriately selected from those used in conventionally known anisotropic conductive films.
• metal particles such as nickel, cobalt, silver, copper, gold, and palladium, alloy particles such as solder, metal-coated resin particles, and the like can be given. Two or more kinds can be used in combination.
• the average particle size of the conductive particles is preferably 2.5 ⁇ m or more and 30 ⁇ m or less in order to be able to cope with variations in wiring height, to suppress increase in conduction resistance, and to suppress occurrence of short circuit. Preferably they are 3 micrometers or more and 9 micrometers or less.
• the particle size of the conductive particles can be measured by a general particle size distribution measuring device, and the average particle size can also be obtained using the particle size distribution measuring device.
• the particle hardness (20% K value; compression elastic deformation characteristic K 20 ) of the resin core particles is preferably 100 to 1000 kgf in order to obtain good connection reliability. / Mm 2 , more preferably 200 to 500 kgf / mm 2 .
• the compression elastic deformation characteristic K 20 can be measured at a measurement temperature of 20 ° C. using, for example, a micro compression tester (MCT-W201, Shimadzu Corporation).
• the abundance of the conductive particles in the anisotropic conductive film is preferably 50 or more and 100,000 or less per square mm, more preferably, in order to suppress a decrease in the efficiency of capturing the conductive particles and suppress the occurrence of short circuit. 200 or more and 70000 or less. This abundance can be measured by observing a thin film of material with an optical microscope.
• anisotropic conductive connection since the electroconductive particle in an anisotropic conductive film exists in a binder composition, it may be difficult to observe with an optical microscope. In such a case, the anisotropic conductive film after anisotropic conductive connection may be observed. In this case, the abundance can be determined in consideration of the film thickness change before and after connection.
• the abundance of the conductive particles in the anisotropic conductive film can also be expressed on a mass basis.
• the abundance is preferably 1 part by mass or more and 30 parts by mass or less, and more preferably 3 parts by mass or more and 10 parts by mass. It is an amount that is equal to or less than part by mass.
• the anisotropic conductive film of the present invention contains a quaternary ammonium salt thermal acid generator instead of a sulfonium salt thermal acid generator as a cationic polymerization initiator. This is to improve the storage life.
• quaternary ammonium salt thermal acid generator a quaternary ammonium cation, a hexafluoroantimonate anion, a hexafluorophosphate anion, a trifluoromethanesulfonate anion, a perfluorobutanesulfonate anion
• examples thereof include salts with dinonylnaphthalene sulfonate anion, p-toluene sulfonate anion, dodecylbenzene sulfonate anion, or tetrakis (pentafluorophenyl) borate anion.
• R1, R2, R3 and R4 are linear, branched or cyclic alkyl groups or aryl groups having 1 to 12 carbon atoms, each having a hydroxyl group, a halogen, an alkoxyl group, an amino group, an ester group or the like. You may do it.
• quaternary ammonium salt thermal acid generator examples include King Industries, Inc. Examples thereof include CXC-1612, CXC-1733, CXC-1738, TAG-2678, CXC-1614, TAG-2690, TAG-2690, TAG-2700, CXC1802-60, and CXC-1821. These are available from Enomoto Kasei Co., Ltd.
• the layer thickness of the anisotropic conductive film of the present invention is preferably 3 to 50 ⁇ m, more preferably 5 to 20 ⁇ m.
• the anisotropic conductive film of the present invention is obtained by dissolving conductive particles and a cationic polymerization initiator in the binder composition described above in an organic solvent such as toluene to form a paint, and using the known film-forming technique. It can be manufactured by forming a film.
• the anisotropic conductive film of the present invention may be a single layer, but reduces the production cost by reducing the amount of conductive particles used without reducing the particle trapping property during anisotropic conductive connection.
• an insulating resin layer may be laminated.
• the anisotropic conductive film of the present invention has a two-layer structure of conductive particle containing layer / insulating resin layer.
• Such an insulating resin layer can be basically formed from a composition obtained by blending a binder composition used in an anisotropic conductive film with a cationic polymerization initiator without containing conductive particles.
• the reaction start temperature of the reaction peak measured with a differential scanning calorimeter is adjusted to 60 to 80 ° C., and the reaction end temperature is 155 to 185 ° C. It is preferable to adjust to. These adjustments can be made by adjusting the blending ratio of the alicyclic epoxy compound and the low polarity oxetane compound.
• the anisotropic conductive film of the present invention anisotropically conducts a first electronic component such as an IC chip, an IC module, and an FPC and a second electronic component such as a plastic substrate, a glass substrate, a rigid substrate, a ceramic substrate, and an FPC. It can be preferably applied when connecting.
• a connection structure in which the first electronic component and the second electronic component are anisotropically conductively connected in the anisotropic conductive film of the present invention is also a part of the present invention.
• a well-known method can be utilized as a connection method of the electronic component using an anisotropic conductive film.
• Example 1 (Formation of conductive particle-containing layer) 60 parts by mass of phenoxy resin (YP-50, Nippon Steel & Sumikin Chemical Co., Ltd.), 10 parts by mass of diepoxybicyclohexyl (Celoxide 8000, Daicel Co., Ltd.) as an alicyclic epoxy compound, low polarity oxetane compound (OXBP, Ube Industries) 20 parts by mass, thermal cationic polymerization initiator (quaternary ammonium salt thermal acid generator, trade name CXC-1612, Enomoto Kasei Co., Ltd.) 2 parts by mass, and conductive particles having an average particle size of 3 ⁇ m 50 parts by mass (Ni / Au plating resin particles, AUL704, Sekisui Chemical Co., Ltd.) was added to toluene to prepare a mixed solution so that the solid content was 50% by mass.
• phenoxy resin YP-50, Nippon Steel & Sumikin Chemical Co., Ltd.
• the obtained mixed liquid was applied on a polyethylene terephthalate release film (PET release film) having a thickness of 50 ⁇ m so as to have a dry thickness of 6 ⁇ m, and dried in an oven at 60 ° C. for 5 minutes to thereby obtain a conductive particle-containing layer. Formed.
• PET release film polyethylene terephthalate release film
• the obtained mixed solution was applied onto a PET peel film having a thickness of 50 ⁇ m so that the dry thickness was 12 ⁇ m, and dried in an oven at 60 ° C. for 5 minutes to form an insulating resin layer.
• Examples 2-4 An alicyclic epoxy compound (Celoxide 8000, Daicel Corp.) and 4,4'-bis [(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl as a low-polar oxetane compound in the conductive particle-containing layer and the insulating resin layer
• An anisotropic conductive film was obtained in the same manner as in Example 1 except that the blending amount (ratio) with (0XBP, Ube Industries, Ltd.) was changed as shown in Table 1.
• Comparative Example 5 Table 1 shows the blending amounts (ratio) of the alicyclic epoxy compound (Celoxide 8000, Daicel Corporation) and the low-polar oxetane compound (0XBP, Ube Industries, Ltd.) in the conductive particle-containing layer and the insulating resin layer.
• An anisotropic conductive film was prepared in the same manner as in Example 1 except for the change as shown.
• the PET release film on the conductive particle-containing layer side of the anisotropic conductive film is peeled off, the anisotropic conductive film is attached to the raw glass from the conductive particle-containing layer side, and a laminate of the raw glass and the anisotropic conductive film is formed. Produced.
• This laminated body was mounted so that the raw glass side was in contact with a hot plate set to 45 ° C., pressure was applied manually from the anisotropic conductive film side, and then cooled to room temperature. After cooling, the PET release film on the insulating resin layer side was peeled from the laminate, and it was confirmed whether only the PET release film was peeled off without peeling the anisotropic conductive film from the raw glass.
• the reaction rate of the anisotropic conductive film in this connection was measured as described below, and the curing temperature was determined from the measurement result. The obtained results are shown in Table 1.
• reaction rate measurement The IC chip of the connection object for evaluation was picked and peeled by hand, the cured anisotropic conductive film was exposed, and the anisotropic conductive film was sampled. The obtained sample was dissolved in acetonitrile so as to have a concentration of 0.1 g / mL. Separately, the anisotropic conductive film before curing was dissolved in acetonitrile so as to have the same concentration, and the peak intensity of each monomer was confirmed using HPLC-MS (WaterS) under the following conditions. The reaction rate at each temperature was determined from the amount of decrease in peak intensity after curing, and the temperature at which the reaction rate reached 80% or more was taken as the curing temperature.
• ⁇ Reaction time> About 5 mg of a sample cut out from the obtained anisotropic conductive film was stored in aluminum PAN (TA Instruments Inc.), which was set in a DSC measuring apparatus (Q2000, TA Instruments Inc.), and 30 ° C. to 250 ° C. Differential scanning calorimetry (DSC) measurement was performed at a temperature rising rate of 10 ° C./min up to ° C. From the obtained DSC chart, the temperature when the exothermic peak rose was read as the reaction start temperature, and the temperature when the exothermic peak changed to the baseline was read as the reaction end temperature. The reaction time was calculated according to the following formula. The obtained results are shown in Table 1.
• the cationic conductive anisotropic conductive film of the present invention using an alicyclic epoxy compound has the same curing temperature and connection reliability as a conventional anisotropic conductive film using a sulfonium salt thermal acid generator. While guaranteeing, it is possible to realize a better storage life than ever, which is useful for anisotropic conductive connection of an electronic component such as an IC chip to a wiring board.

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