CN103351838A - Adhesive composition, connection structure, method for producing connection structure, and use of adhesive composition - Google Patents

Adhesive composition, connection structure, method for producing connection structure, and use of adhesive composition Download PDF

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Publication number
CN103351838A
CN103351838A CN2013102289914A CN201310228991A CN103351838A CN 103351838 A CN103351838 A CN 103351838A CN 2013102289914 A CN2013102289914 A CN 2013102289914A CN 201310228991 A CN201310228991 A CN 201310228991A CN 103351838 A CN103351838 A CN 103351838A
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China
Prior art keywords
adhesive composite
methyl
circuit block
splicing ear
acid
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Pending
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CN2013102289914A
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Chinese (zh)
Inventor
伊泽弘行
加藤木茂树
工藤直
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Showa Denko Materials Co ltd
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Hitachi Chemical Co Ltd
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Publication of CN103351838A publication Critical patent/CN103351838A/en
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    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
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    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
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    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
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    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
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    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
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    • 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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    • H01—ELECTRIC ELEMENTS
    • 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
    • H01B1/20—Conductive material dispersed in non-conductive organic material
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Abstract

Disclosed is an adhesive composition for connecting a first circuit member having first connection terminals on the primary surface, and a second circuit member having second connection terminals on the primary surface. The disclosed adhesive composition contains (a) a thermoplastic resin, (b) a radical-polymerizable compound, and (c) a radical polymerization initiator, and (d) a vinyl compound containing a phosphoric acid group, wherein the radical-polymerizable compound (b) contains urethane (meth)acrylate having a critical surface tension of 300 to 500%.

Description

The manufacture method of adhesive composite, syndeton body, syndeton body and the application of adhesive composite
The present invention is that application number is that the 2011800010173(international application no is PCT/JP2011/062418), the applying date the dividing an application for the patent application of " manufacture method of adhesive composite, syndeton body, syndeton body and the application of adhesive composite " that be on May 30th, 2011, denomination of invention.
Technical field
The present invention relates to the manufacture method of adhesive composite, syndeton body, syndeton body and the application of adhesive composite.
Background technology
In semiconductor element and liquid crystal display device, in order to make the various parts combinations in the element, use various adhesive composites all the time.To the requirement of caking agent, take cementability as representative, relate to widely reliability under thermotolerance, the humid tropical condition etc.In addition, about bonding employed adherend, can use take organic substrates such as printed-wiring board (PWB) or polyimide, polyethylene terephthalate (PET), polycarbonate (PC), PENs (PEN) as main the metal such as copper, aluminium or ITO (composite oxides of indium and tin), IZO (composite oxides of indium and zinc), SiN, SiO 2Deng the base material with various condition of surface, therefore need to meet the molecular designing of the adhesive composite of each adherend.In addition, in recent years, because therefore the slimming of the electronics of semiconductor element mounted thereon and liquid crystal display device requires the also slimming of base material as adherend.
All the time, as the caking agent of above-mentioned semiconductor element, used for liquid crystal display element, can use and adopt the thermosetting resin (for example, with reference to patent documentation 1) that shows the Resins, epoxy of high adhesion and high reliability.As the constituent of resin, normal operation Resins, epoxy, have the solidifying agent such as reactive resol with Resins, epoxy, promote the hot Latence catalyst that Resins, epoxy and solidifying agent react.Hot Latence catalyst is the material that shows hyperergy not reacting under the storing temps such as room temperature when heating, it is the important factor that determines solidification value and curing speed, the viewpoint of the curing speed during from caking agent stability in storage at room temperature and heating can be used various compounds.As the condition of cure in the actual operation, by 170～250 ℃ temperature-curable 1～3 hour, obtained required bonding.
Yet, along with the high-precision refinement of highly integrated, the liquid crystal cell of nearest semiconductor element, narrow and smallization of spacing between the element and between the circuit, the heating during curing may bring detrimentally affect to circumferential component.And for cost degradation, exist to improve the necessity of throughput, thereby require more solidifying in low temperature and the shorter time, in other words, need to be under low temperature fast setting condition bonding.In order to realize this low temperature fast setting, need to use the low hot Latence catalyst of activation energy, but be difficult to have both the stability in storage of near room temperature.
Wherein, the radical-curable caking agent receives publicity, and the free-radical polymerised compounds such as acrylate derivative, methacrylate derivative and superoxide as radical polymerization initiator have been used in its merging.The radical-curable caking agent, since rich reactive as the free radical of reactive behavior kind, therefore can solidify (for example, with reference to patent documentation 2) short period of time.Yet, the radical-curable caking agent, the cure shrinkage during owing to heating is large, therefore compares with the situation of using Resins, epoxy, and bonding strength is poor.For the reduction of such bonding strength, proposed to give flexible, as to have improved bonding strength caking agent (with reference to patent documentation 3,4) by ehter bond.In addition, also proposed to make the absorption of stress particle that comprises the rubber series resilient material to be dispersed in the caking agent (with reference to patent documentation 5) of the improvement that realizes bonding strength in the caking agent.
Patent documentation 1: Japanese kokai publication hei 1-113480 communique
Patent documentation 2: TOHKEMY 2002-203427 communique
Patent documentation 3: No. 3522634 communique of Japan's special permission
Patent documentation 4: TOHKEMY 2002-285128 communique
Patent documentation 5: No. 3477367 communique of Japan's special permission
Summary of the invention
Invent problem to be solved
Yet, because the radical-curable caking agent is at low temperature, solidify in the short period of time, therefore to organic substrate, ITO, IZO, SiN, SiO such as polyimide, PET, PC, PEN 2Wettability Deng inorganic substrate is difficult to obtain fully.For example, even use the method for record in the above-mentioned patent documentation 3～5, also can produce the sufficient wettability that can not get above-mentioned organic substrate, inorganic substrate, the problem that bonding strength reduces.In addition, along with as the above-mentioned organic substrate of adherend, the slimming of inorganic substrate, more need flexibleization, the elongation of adhesive composite, but in the method for above-mentioned patent documentation 3,4 records, exist adhesive composite to can not get fully flexible, elongation, the problem that bonding strength reduces.
Therefore, even under the condition of cure of low temperature, short period of time, also can obtain excellent bonding strength, and adhesive composite, the syndeton body that has used the circuit block of this adhesive composite, the manufacture method of syndeton body and the application of adhesive composite that also can keep afterwards stable performance (bonding strength, contact resistance) in long reliability test (high temperature and humidity test) even the purpose of this invention is to provide.
Solve the embodiment of problem
In order to achieve the above object, the invention provides a kind of adhesive composite (the 1st adhesive composite), it is for the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, adhesive composite contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) radical polymerization initiator and the vinyl compound that (d) has phosphate, (b) free-radical polymerised compound comprises urethane (methyl) acrylate of the critical surface tension with 20～40mN/m.
Above-mentioned the 1st adhesive composite contains above-mentioned each composition, and (b) free-radical polymerised compound comprises urethane (methyl) acrylate of the critical surface tension with 20～40mN/m, can improve organic substrate, ITO, IZO, SiN, SiO such as polyimide, PET, PC, PEN thus 2Deng the wettability of inorganic substrate, can realize bonding under the low-temperature curing condition can improving the bonding strength between the circuit block.In addition, even also can keep stable performance after the reliability test for a long time.
The 1st adhesive composite of the present invention, optimization polyurethane (methyl) acrylate is 600～5000Pas 25 ℃ viscosity.By make urethane (methyl) acrylate 25 ℃ viscosity in above-mentioned scope, can obtain the flowability of appropriateness, improve wettability, improve the bonding strength between the circuit block.
In addition, the 1st adhesive composite of the present invention, the weight-average molecular weight of optimization polyurethane (methyl) acrylate is more than 10000 and less than 25000.Weight-average molecular weight by making urethane (methyl) acrylate can be given flexible with appropriateness of adhesive composite in above-mentioned scope, improve the bonding strength between the circuit block, obtains excellent connection reliability.
The 1st adhesive composite of the present invention, preferred elongation at break is 300～500%.By making elongation at break in above-mentioned scope, can give adhesive composite with flexible fully, improve the bonding strength between the circuit block, obtain excellent connection reliability.
The invention provides a kind of adhesive composite (the 2nd adhesive composite), it is for the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, adhesive composite contains (a) thermoplastic resin, (b) free-radical polymerised compound and (c) radical polymerization initiator, (b) free-radical polymerised compound comprises urethane (methyl) acrylate, and elongation at break is 300～500%.
Above-mentioned the 2nd adhesive composite contains above-mentioned each composition, and (b) free-radical polymerised compound comprises urethane (methyl) acrylate, elongation at break is in above-mentioned scope, can give thus flexible fully, follow the distortion of adherend (polyimide, PET, PC, PEN etc.), therefore can improve the bonding strength between the circuit block, obtain excellent connection reliability.
The 2nd adhesive composite of the present invention preferably also contains the vinyl compound that (d) has phosphate.The vinyl compound that has phosphate by containing (d) can improve the cementability to metal base.In addition, can obtain bonding strength to the excellence of circuit block with the splicing ear that is consisted of by metal or ITO, IZO etc.
The the of the present invention the 1st and/or the 2nd adhesive composite, preferably the storage modulus in the time of 200 ℃ is 0.5～5MPa.Think by making storage modulus 200 ℃ the time in above-mentioned scope, can have fully flexible and cross-linking density concurrently, and relax the adherend of adhesive composite and the stress at adhesive composite interface.Therefore, can improve the bonding strength between the circuit block, even and also can keep stable performance after the reliability test for a long time.
In addition, the the of the present invention the 1st and/or the 2nd adhesive composite, preferred (a) thermoplastic resin contain at least a kind of resin in the group that is selected from phenoxy resin, urethane resin, polyester urethane resin, butyral resin, acrylic resin and polyimide resin composition.As (a) thermoplastic resin, contain above-mentioned resin, can further improve thus thermotolerance, the cementability of adhesive composite.
In addition, the of the present invention the 1st and/or the 2nd adhesive composite preferably also contains (e) electroconductive particle.By containing (e) electroconductive particle, can give adhesive composite with good electroconductibility or anisotropic conductive, therefore can be more suitable for be used to the bonding purposes each other of the circuit block with splicing ear etc.In addition, can reduce more fully Jie has been carried out the circuit block of electrical connection by the above-mentioned the 1st and/or the 2nd adhesive composite contact resistance.
In addition, the invention provides a kind of syndeton body of circuit block, comprise: the first circuit block that has the first splicing ear on the interarea, the second circuit parts that have the second splicing ear on the interarea, and interconnecting piece, in the first splicing ear mode relative with the second splicing ear, the first circuit block and second circuit parts are situated between by comprising the above-mentioned the 1st and/or the interconnecting piece of the 2nd adhesive composite and disposing, and the first splicing ear and the second splicing ear are electrically connected, and the first circuit block and/or second circuit parts are that the base material of the thermoplastic resin below 200 ℃ consists of by comprising second-order transition temperature.
Such syndeton body, because the connection of a pair of circuit block can use the of the present invention the above-mentioned the 1st and/or the cured article of the 2nd adhesive composite, therefore can follow and comprise the distortion that second-order transition temperature is the base material of the thermoplastic resin below 200 ℃, also can improve the wettability to base material, improve fully the bonding strength between the circuit block.In addition, even also can keep stable performance after the reliability test for a long time.
In the syndeton body of circuit block of the present invention, second-order transition temperature is that the thermoplastic resin below 200 ℃ is preferably at least a kind of resin that is selected from polyethylene terephthalate, polycarbonate and the PEN.Above-mentioned syndeton body, because the connection of a pair of circuit block can use the of the present invention the above-mentioned the 1st and/or the cured article of the 2nd adhesive composite, therefore can follow the distortion that comprises the base materials such as polyethylene terephthalate, also can improve the wettability to base material, improve fully the bonding strength between the circuit block.In addition, even also can keep stable performance after the reliability test for a long time.
In addition, in the syndeton body of circuit block of the present invention, a circuit block in the first circuit block or the second circuit parts consists of by containing the base material that is selected from a kind of material in the group that polyethylene terephthalate, polycarbonate and PEN form at least, and another circuit block in the first circuit block or the second circuit parts is polyimide resin preferably.In this syndeton body, the first circuit block and second circuit parts consist of with base material as described above, can further improve thus wettability and bonding strength with adhesive composite, obtain excellent connection reliability.
The invention provides a kind of manufacture method of syndeton body of circuit block, comprise following operation: the operation that the second circuit parts that have the second splicing ear on the first circuit block of having the first splicing ear on the interarea and the interarea are situated between and are disposed in the first splicing ear mode relative with the second splicing ear by above-mentioned adhesive composite; And with adhesive composite heating, it is solidified, thereby connect the operation of the first circuit block and second circuit parts.According to this manufacture method, connect by the first circuit block is connected above-mentioned adhesive composite with the second circuit parts, can obtain to have the syndeton body of the circuit block of excellent connection reliability.
In addition, the invention provides a kind of application of adhesive composite, for the second circuit parts that have the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, described adhesive composite (the 1st adhesive composite) contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) radical polymerization initiator and the vinyl compound that (d) has phosphate, (b) free-radical polymerised compound comprises urethane (methyl) acrylate of the critical surface tension with 20～40mN/m.Above-mentioned the 1st adhesive composite, owing to contain above-mentioned each composition, and (b) free-radical polymerised compound comprises urethane (methyl) acrylate of the critical surface tension with 20～40mN/m, therefore can improve organic substrate, ITO, IZO, SiN, SiO such as polyimide, PET, PC, PEN 2Deng the wettability of inorganic substrate, can realize bonding under the low-temperature curing condition can improving the bonding strength between the circuit block.In addition, even also can keep stable performance after the reliability test for a long time.
In above-mentioned application, the viscosity of optimization polyurethane (methyl) acrylate in the time of 25 ℃ is 600～5000Pas.By making the viscosity of urethane (methyl) acrylate 25 ℃ the time in above-mentioned scope, can obtain the flowability of appropriateness, improve wettability, obtain excellent connection reliability.
In above-mentioned application, the weight-average molecular weight of optimization polyurethane (methyl) acrylate is more than 10000 and less than 25000.Weight-average molecular weight by making urethane (methyl) acrylate can be given flexible with appropriateness of adhesive composite in above-mentioned scope, improve the bonding strength between the circuit block, obtains excellent connection reliability.
In above-mentioned application, the elongation at break of preferred adhesive composite is 300～500%.By making elongation at break in above-mentioned scope, can give adhesive composite with flexible fully, improve the bonding strength between the circuit block, obtain excellent connection reliability.
In addition, the invention provides a kind of application of adhesive composite, for the second circuit parts that have the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, described adhesive composite (the 2nd adhesive composite) contains (a) thermoplastic resin, (b) free-radical polymerised compound and (c) radical polymerization initiator, (b) free-radical polymerised compound comprises urethane (methyl) acrylate, and elongation at break is 300～500%.Above-mentioned the 2nd adhesive composite, owing to contain above-mentioned each composition, and (b) free-radical polymerised compound comprises urethane (methyl) acrylate, elongation at break is in above-mentioned scope, thereby can give flexible fully, and the distortion of following adherend (polyimide, PET, PC, PEN etc.), therefore can improve the bonding strength between the circuit block, obtain excellent connection reliability.
In above-mentioned application, adhesive composite preferably also contains the vinyl compound that (d) has phosphate.The vinyl compound that has phosphate by containing (d) can improve the cementability to metal base, but also can obtain the bonding strength to the excellence of circuit block with the splicing ear that is made of metal, ITO, IZO etc.
In above-mentioned application, the preferred storage modulus of adhesive composite in the time of 200 ℃ is 0.5～5MPa.Think by making 200 ℃ storage modulus in above-mentioned scope, can have fully flexible and cross-linking density concurrently, relaxed the adherend of adhesive composite and the stress at adhesive composite interface.Therefore, can improve the bonding strength between the circuit block, even and also can keep stable performance after the reliability test for a long time.
In above-mentioned application, preferred (a) thermoplastic resin contains at least a kind of resin in the group that is selected from phenoxy resin, urethane resin, polyester urethane resin, butyral resin, acrylic resin and polyimide resin composition.As (a) thermoplastic resin, by containing above-mentioned resin, can further improve thermotolerance, the cementability of adhesive composite.
In above-mentioned application, preferred adhesive composite also contains (e) electroconductive particle.By containing (e) electroconductive particle, can give adhesive composite with good electroconductibility or anisotropic conductive, thereby can be more suitable for be used to the bonding purposes each other of the circuit block with splicing ear etc., and can reduce more fully to be situated between and carried out the contact resistance of the circuit block that is electrically connected by the above-mentioned the 1st and/or the 2nd adhesive composite.
The invention effect
According to the present invention, even under the condition of cure of low temperature, also can obtain excellent bonding strength, and adhesive composite, the syndeton body that has used the circuit block of this adhesive composite, the manufacture method of syndeton body and the application of adhesive composite that also can keep afterwards stable performance (bonding strength, contact resistance) in long reliability test (high temperature and humidity test) even can provide.
Description of drawings
Fig. 1 is the diagrammatic cross-section of an embodiment that shows the syndeton body of the circuit block used adhesive composite of the present invention.
Fig. 2 is the diagrammatic cross-section that is presented at syndeton body the first circuit block, second circuit parts and the adhesive composite before of making circuit block shown in Figure 1.
Fig. 3 is the diagrammatic cross-section of an embodiment that shows the syndeton body of the circuit block used adhesive composite of the present invention (containing electroconductive particle).
Fig. 4 is the diagrammatic cross-section that is presented at syndeton body the first circuit block, second circuit parts and the adhesive composite (containing electroconductive particle) before of making circuit block shown in Figure 3.
Embodiment
Below, according to circumstances with reference to accompanying drawing preferred implementation of the present invention is elaborated.In addition, in the accompanying drawings, to identical or corresponding section mark same-sign, the repetitive description thereof will be omitted.In addition; in the present invention; (methyl) vinylformic acid represents vinylformic acid or the methacrylic acid corresponding with it, and (methyl) acrylate refers to acrylate or the methacrylic ester corresponding with it, and (methyl) acryl refers to acryl or methacryloyl.
" critical surface tension (γ in the present embodiment c) " refer to; urethane (methyl) acrylate of liquid or urethane (methyl) acrylate are dissolved in the solvent; the liquids of gained is coated on the fluororesin film by coating unit; at 70 ℃; maybe can remove in 10 minutes under the temperature and time of employed solvent and carry out warm air drying; practical measurement drips pure water to membranaceous urethane (methyl) acrylate of gained respectively at 23 ℃, wetting tension test mixing solutions No.50, at once the angle (contact angle θ) that becomes with urethane (methyl) acrylate surface after 60 (with the pure pharmaceutical worker of light industry (strain) system), the 1 μ l, when the surface tension with each liquid is made as the x axle, when COS θ is made as the drawing of y axle, the surface tension of straight line when Y=1.In addition, passing 3 the straight line during at Y=1 of measuring gained by above-mentioned pure water, No.50,60, becoming in the situation of negative value at X, also can use pure water, wetting tension test to carry out and above-mentioned same mensuration with mixing solutions No.60,1-bromonaphthalene (with the pure pharmaceutical worker's industry of light (strain) system), use the capillary value of 3 straight line when Y=1 of passing gained.
In addition, " storage modulus " in the present embodiment refers to, adhesive composite is coated on the fluororesin film by coating unit, at 70 ℃, maybe can remove in 10 minutes under the temperature and time of employed solvent and carry out warm air drying, the membranaceous adhesive composite of gained was heating and curing 1 hour at 180 ℃, the sample of gained is used TA instrument company's viscoelasticity analysis device processed " RSA-3 " (trade(brand)name), 5 ℃/minute of heat-up rates, frequency 10Hz, measure under the condition of temperature-150～300 ℃ and measure, in the value of 200 ℃ storage moduluss (E ').
" elongation at break " in the present embodiment refers to, adhesive composite is coated on the fluororesin film by coating unit, at 70 ℃, maybe can remove in 10 minutes under the temperature of employed solvent and the condition and carry out warm air drying, the membranaceous adhesive composite of gained was heating and curing 1 hour at 180 ℃, the sample of gained is used Instron company's prepared material trier " microtester5548 " (trade(brand)name), at draw speed 50mm/ minute, measuring temperature measures under 25 ℃ condition, when film ruptures, by between the length L between punctuate and original punctuate apart from L 0Use following formula (1) to calculate the value of gained.
Elongation at break (%)=(L-L 0)/L 0* 100 (1)
In addition, " viscosity " in the present embodiment refers to urethane (methyl) acrylate is used Anton Paar company rheometer processed " Physica MCR301 " (trade(brand)name), at frequency 1Hz, measure the value of mensuration gained under the condition of 25 ℃ of temperature.
" second-order transition temperature (Tg) " in the present embodiment refers to membranaceous organic substrate is used TA instrument company's viscoelasticity analysis device processed " RSA-3 " (trade(brand)name), at 5 ℃/minute of heat-up rates, frequency 10Hz, near the value of tan δ peak temperature that measure that mensuration obtains under the condition of temperature-150～300 ℃, the Tg.
In addition, in the present embodiment, " weight-average molecular weight " and " number-average molecular weight " refer to according to the condition shown in the table 1, the value of the standard curve determination gained by gel permeation chromatography (GPC) Application standard polystyrene.
[table 1]
Figure BDA00003327258900091
(the 1st embodiment)
The adhesive composite that the 1st embodiment of the present invention relates to is characterised in that, it is for the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, adhesive composite contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) radical polymerization initiator, (d) have the vinyl compound of phosphate, (b) free-radical polymerised compound comprises carbamate (methyl) acrylate of the critical surface tension with 20～40mN/m.
Below, explain each composition.The resin (polymer) that present embodiment employed (a) thermoplastic resin refers to have following character: become the high liquid state of viscosity by heating, if the freely distortion by external force is cooling and remove external force then keeping under the state of its shape hardening and can repeat this process.In addition, also comprise the resin that contains reactive functional groups (polymer) with above-mentioned character.(a) second-order transition temperature of thermoplastic resin (Tg) is preferably 0～190 ℃, more preferably 20～170 ℃.
As such (a) thermoplastic resin, can use polyimide resin, polyamide resin, phenoxy resin, (methyl) acrylic resin, urethane resin, polyester urethane resin, polyvinyl butyral resin etc.These resins can use separately or mix more than 2 kinds and use.In addition, in these thermoplastic resins, can comprise siloxane bond, fluoro substituents.So long as the resin that mixes is fully compatible or produce microphase-separated and the state of gonorrhoea each other, just can be fit to use.
In the situation about utilizing, the molecular weight of above-mentioned thermoplastic resin is larger making adhesive composite form membranaceous, and the film formative that easier acquisition is good in addition, can be set impact in a wide range as the melt viscosity of the flowability of film-like adhesive composition.As the weight-average molecular weight of (a) thermoplastic resin, be preferably 5,000～150,000, more preferably 10,000～80,000.If weight-average molecular weight is lower than 5,000, then tend to be difficult for obtaining good film formative, if greater than 150,000, then tend to be difficult for the excellent compatibility of acquisition and other composition.
The content of (a) thermoplastic resin in the adhesive composite take the adhesive composite total amount as benchmark, is preferably 5～80 quality %, more preferably 15～70 quality %.If its content is lower than 5 quality %, then in the situation about utilizing, tend to especially be difficult for obtaining good film formative making adhesive composite form membranaceous, if greater than 80 quality %, then tend to be difficult for obtaining the flowability of good adhesive composite.
(b) free-radical polymerised compound that the adhesive composite of present embodiment is contained, the effect at radical polymerization initiator that refers to issues the compound of living radical polymerization, but also can be to make the compound that itself produces free radical by giving the activation energy such as light, heat.As (b) free-radical polymerised compound, can be fit to use have the compound that comes the functional group of polymerization such as vinyl, (methyl) acryl, allyl group, dimaleoyl imino etc. by living radical.
As (b) free-radical polymerised compound, particularly, can enumerate epoxy (methyl) origoester acrylate, carbamate (methyl) origoester acrylate, polyethers (methyl) origoester acrylate, the oligopolymer such as polyester (methyl) origoester acrylate, trimethylolpropane tris (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, polyalkylene glycol two (methyl) acrylate, dicyclopentenyl (methyl) acrylate, dicyclopentenyl oxygen base ethyl (methyl) acrylate, neopentyl glycol two (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, isocyanuric acid modification 2 officials energy (methyl) acrylate, isocyanuric acid modification 3 officials energy (methyl) acrylate, two phenoxyethyl alcohol fluorenes acrylate, the glycidyl that makes the bisphenol fluorene diglycidyl ether with (methyl) vinylformic acid addition and epoxy (methyl) acrylate, two phenoxyethyl alcohol fluorenes acrylate, the glycidyl that makes the bisphenol fluorene diglycidyl ether with (methyl) vinylformic acid addition and epoxy (methyl) acrylate, in the glycidyl that makes the bisphenol fluorene diglycidyl ether and ethylene glycol and/or propylene glycol addition and compound in import the compound of (methyl) acryloxy gained, following general formula (A) and (B) shown in compound etc.
[changing 1]
Figure BDA00003327258900111
[in the formula (A), R 1And R 2Represent independently of one another hydrogen atom or methyl, a and b represent 1～8 integer independently of one another.]
[changing 2]
[in the formula (B), R 3And R 4Represent independently of one another hydrogen atom or methyl, c and d represent 0～8 integer independently of one another.]
In addition, as (b) free-radical polymerised compound, can be separately in situation about leaving standstill under 30 ℃ for wax-like (ワ ッ Network ス shape), wax shape (ろ う shape), crystalloid, glassy, powdery etc. without compound mobile, that show solid state, can use with being not particularly limited.As such (b) free-radical polymerised compound, particularly, can enumerate N, N '-methylene-bisacrylamide, diacetone-acryloamide(DAA), N-hydroxymethyl acrylamide, N-phenyl methyl acrylamide, 2-acrylamide-2-methyl propane sulfonic acid, three (2-acryloxy ethyl) isocyanuric acid ester, N-phenylmaleimide, N-(o-methyl-phenyl-) maleimide, N-(aminomethyl phenyl) maleimide, N-(p-methylphenyl)-maleimide, N-(o-methoxyphenyl) maleimide, N-(m-methoxyphenyl) maleimide, N-(p-methoxyphenyl)-maleimide, N-methyl maleimide, NEM, N-octyl group maleimide, 4,4 '-ditan bismaleimides, meta-phenylene bismaleimide, 3,3 '-dimethyl-5,5 '-diethyl-4,4 '-ditan bismaleimides, the 4-methyl isophthalic acid, 3-phenylene bismaleimides, N-methacryloxy maleimide, N-acryloxy maleimide, 1,6-bismaleimides-(2,2,4-trimethylammonium) hexane, N-methacryloxy succsinic acid imide, N-acryloxy succsinic acid imide, 2-naphthyl methyl acrylate, 2-naphthyl acrylate, tetramethylol methane tetraacrylate, the divinyl ethylidene-urea, divinyl propylidene urea, the polystyrene-based ethyl of 2-(methacrylic ester), N-phenyl-N '-(3-methacryloxy-2-hydroxypropyl)-Ursol D, N-phenyl-N '-(3-acryloxy-2-hydroxypropyl)-Ursol D, tetramethyl-piperidyl (methacrylic ester), the tetramethyl-piperidyl acrylate, pentamethyl-piperidyl (methacrylic ester), pentamethyl-piperidyl acrylate, the octadecyl acrylate, N tert butyl acrylamide, diacetone acrylamide, N-(hydroxymethyl) acrylamide, compound shown in the following general formula (C)～(L) etc.
[changing 3]
Figure BDA00003327258900121
[in the formula (C), e represents 1～10 integer.]
[changing 4]
Figure BDA00003327258900122
[changing 5]
Figure BDA00003327258900123
[in the formula (E), R 5And R 6Represent independently of one another hydrogen atom or methyl, f represents 15～30 integer.]
[changing 6]
[in the formula (F), R 7And R 8Represent independently of one another hydrogen atom or methyl, g represents 15～30 integer.]
[changing 7]
Figure BDA00003327258900132
[in the formula (G), R 9Expression hydrogen atom or methyl.]
[changing 8]
Figure BDA00003327258900133
[in the formula (H), R 10Expression hydrogen atom or methyl, h represents 1～10 integer.]
[changing 9]
Figure BDA00003327258900134
[in the formula (I), R 11Expression hydrogen atom or following general formula (i) or (ii) shown in organic group, i represents 1～10 integer.]
[changing 10]
Figure BDA00003327258900141
[changing 11]
Figure BDA00003327258900142
[changing 12]
Figure BDA00003327258900143
[in the formula (J), R 12Expression hydrogen atom or following general formula (iii) or (iv) shown in organic group, j represents 1～10 integer.]
[changing 13]
Figure BDA00003327258900144
[changing 14]
Figure BDA00003327258900145
[changing 15]
Figure BDA00003327258900151
[in the formula (K), R 13Expression hydrogen atom or methyl.]
[changing 16]
Figure BDA00003327258900152
[in the formula (L), R 14Expression hydrogen atom or methyl.]
In addition, can with as the compound that belongs to (b) free-radical polymerised compound be selected from N-vinyl compound and N, the N-vinyl compound in the N-dialkyl group vinyl compound merges with in addition (b) free-radical polymerised compound and uses.Use the N-vinyl compound by merging, can improve the crosslinking rate of adhesive composite.
As the N-vinyl compound, particularly, can enumerate N-vinyl imidazole, N-vinyl pyridine, NVP, N-vinyl formamide, N-caprolactam, 4, two (the N of 4 '-vinylidene, accelerine), N-vinyl acetamide, N, N-DMAA, N, N-diethyl acrylamide etc.
In addition, the vinyl compound that (d) described later has phosphate is the compound that works as free-radical polymerised compound, but (b) free-radical polymerised compound in this specification sheets refers to the free-radical polymerised compound except (d) has the vinyl compound of phosphate.
The content of (b) free-radical polymerised compound in the adhesive composite with respect to (a) thermoplastic resin 100 mass parts, is preferably 50～250 mass parts, more preferably 60～150 mass parts.If above-mentioned content is lower than 50 mass parts, be difficult for obtaining sufficient thermotolerance after then tending to solidify, in addition, if surpass 250 mass parts, then in situation about using as film, tend to be difficult for obtaining good film formative.
The adhesive composite of present embodiment contains the urethane that critical surface tension is 20～40mN/m (methyl) acrylate as (b) free-radical polymerised compound.Wherein, in the present embodiment, more preferably use the urethane acrylate of above-mentioned critical surface tension.Above-mentioned urethane (methyl) acrylate can obtain by the condensation reaction of fatty family vulcabond and aliphatic diol.
The fatty family vulcabond that consists of above-mentioned urethane (methyl) acrylate is selected from the fourth vulcabond, hexamethylene diisocyanate, lysinediisocyanate, 2-methylpentane-1, the 5-vulcabond, 3-methylpentane-1, the 5-vulcabond, 2,2,4-tri-methyl hexamethylene-1, the 6-vulcabond, 2,4,4-tri-methyl hexamethylene-1, the 6-vulcabond, isophorone diisocyanate, cyclohexyl diisocyanate, the hydrogenation of benzene dimethylene diisocyanate, hydrogenated diphenyl methane diisocyanate, hydrogenation Three methyl Benzene dimethylene diisocyanate etc.
In addition, the aliphatic diol that consists of above-mentioned urethane (methyl) acrylate is selected from ethylene glycol, propylene glycol, 1, the 2-propylene glycol, 1, ammediol, 1, the 3-butyleneglycol, 1, the 4-butyleneglycol, neopentyl glycol, 1, the 2-pentanediol, 1, the 4-pentanediol, 1, the 5-pentanediol, 2, the 4-pentanediol, 2-methyl-2, the 4-pentanediol, 2,4-dimethyl-2, the 4-pentanediol, 2,2,4-trimethylammonium-1, the 3-pentanediol, 1, the 2-hexylene glycol, 1, the 5-hexylene glycol, 1, the 6-hexylene glycol, 2, the 5-hexylene glycol, 2-ethyl-1, the 3-hexylene glycol, 2,5-dimethyl-2, the 5-hexylene glycol, 1, the 2-ethohexadiol, 1, the 8-ethohexadiol, 1, the 7-heptanediol, 1, the 9-nonanediol, 1, the 2-decanediol, 1, the 10-decanediol, 1, the 12-decanediol, dodecanediol, tetramethyl ethylene ketone, 1, the 4-butynediol, triethylene glycol, glycol ether, dipropylene glycol, the low-molecular-weight diol class that cyclohexanedimethanol etc. are saturated, by the polycarbonate diol class of the above-mentioned glycols more than at least a kind and carbonyl chloride reaction gained, with the above-mentioned glycols more than at least a kind as initiator with oxyethane, propylene oxide, the polyether glycol class by known method addition polymerization gained more than a kind or a kind of the monomers such as Epicholorohydrin is with hexanodioic acid, 3-methyl hexanodioic acid, 2,2,5,5-tetramethyl-hexanodioic acid, toxilic acid, fumaric acid, succsinic acid, 2,2-dimethyl succinate, 2-Ethyl-2-Methyl succsinic acid, 2, the 3-dimethyl succinate, oxalic acid, propanedioic acid, Methylpropanedioic acid, ethyl malonic acid, butyl malonic acid, dimethyl malonic acid, pentanedioic acid, the 2-methylglutaric acid, the 3-methylglutaric acid, 2, the 2-dimethylated pentanedioic acid, 3,3-dimethylated pentanedioic acid, 2,4-dimethylated pentanedioic acid, pimelic acid, suberic acid, nonane diacid, the polyester glycol class of the diprotic acid such as sebacic acid or the acid anhydrides dehydrating condensation gained corresponding with them; Polyester glycol class with cyclic ester compound ring-opening polymerization gained such as 6-caprolactones.Both can be used separately by the polyester glycol class that above-mentioned glycols and dicarboxylic acid obtain, and also polyester glycol class more than 2 kinds can be mixed and use.If use these polyester glycol classes, then be easy to the critical surface tension of urethane (methyl) acrylate is controlled in the scope of 20～40mN/m.
The critical surface tension of above-mentioned urethane (methyl) acrylate is 20～40mN/m, is preferably 20～35mN/m, more preferably 20～33mN/m.In the situation of critical surface tension in above-mentioned scope of urethane (methyl) acrylate, with approach as critical surface tensions such as the polyimide of adherend, PET, wettability improves, and therefore can improve bonding strength, obtains excellent connection reliability.In addition, if this critical surface tension is lower than 20mN/m or surpasses 40mN/m, then may be to wettability reduction, the consistency variation of polyimide, PET, PC, PEN etc.Think that the critical surface tension of above-mentioned urethane (methyl) acrylate is relevant with the ammonia ester bond equivalent, and can adjust by the number-average molecular weight that changes glycol.For example, if the number-average molecular weight of glycol is increased, then tend to the ammonia ester bond equivalent and reduce, critical surface tension reduces.
In the adhesive composite of present embodiment, from improving the viewpoint to the bonding strength of the base materials such as polyimide, PET, PC, PEN, the weight-average molecular weight of above-mentioned urethane (methyl) acrylate is preferably more than 10000 and in less than 25000 scope.As long as the weight-average molecular weight of above-mentioned urethane (methyl) acrylate is in above-mentioned scope, just can obtain flexibility and cohesive force, and can raising and the bonding strength of the organic substrates such as polyimide, PET, PC, PEN, obtain excellent connection reliability.In addition, from obtaining fully the viewpoint of above-mentioned effect, the weight-average molecular weight of above-mentioned urethane (methyl) acrylate is more preferably more than 12000 and be lower than 20000.The weight-average molecular weight of above-mentioned urethane (methyl) acrylate if be lower than 10000, is then tended to can not get flexible fully, if be more than 25000, then the flowability of adhesive composite is tended to reduce.
The viscosity of above-mentioned urethane (methyl) acrylate in the time of 25 ℃ is preferably 600～5000Pas, more preferably 600～4500Pas.In the situation of viscosity in above-mentioned scope of urethane (methyl) acrylate in the time of 25 ℃, can obtain sufficient flowability, obtain excellent connection reliability.In addition, can obtain the bonding force of appropriateness, operability is excellent.On the other hand, be lower than in the situation of 600Pas, tending to bonding force increases, and the operability variation if surpass 5000Pas, then tends to can not get sufficient flowability, to the wettability reduction of adherend, bonding strength and connection reliability variation.
In addition, the content of above-mentioned urethane (methyl) acrylate is preferably 5～95 quality % take the adhesive composite total amount as benchmark, more preferably 10～80 quality %.Be lower than at content in the situation of 5 quality %, thermotolerance is tended to be easy to reduce, if surpass 95 quality %, then in situation about using as film, the film formative is tended to be easy to reduce.
As contained (c) radical polymerization initiator of the adhesive composite of present embodiment, can use all the time known organo-peroxide, azo-compound etc. by provide energy to produce the compound of free radical from the outside.As (c) radical polymerization initiator, from the viewpoint of stability, reactive, consistency, preferred 1 minute half life temperature is that 90～175 ℃ and molecular weight are 180～1000 organo-peroxide.1 minute half life temperature is in this scope, and stability in storage is excellent thus, improves fully free-radical polymerisedly, can solidify at short notice.
As (c) radical polymerization initiator, particularly, can enumerate 1,1,3,3-tetramethyl butyl new decanoate ester peroxide, two (4-tert-butylcyclohexyl) peroxy dicarbonate, two (2-ethylhexyl) peroxy dicarbonate, the cumyl new decanoate ester peroxide, 1,1,3,3-tetramethyl butyl new decanoate ester peroxide, dilauroyl peroxide, 1-cyclohexyl-1-methylethyl new decanoate ester peroxide, uncle's hexyl new decanoate ester peroxide, tert-butyl hydroperoxide neodecanoic acid ester, t-butylperoxy pivarate, 1,1,3,3-tetramethyl butyl peroxidation-2-ethylhexanoate, 2,5-dimethyl-2,5-two (peroxidation of 2-ethyl hexanoyl) hexane, uncle's hexyl peroxidation-2-ethylhexanoate, tert-butyl hydroperoxide-2-ethylhexanoate, the new heptanoate of tert-butyl hydroperoxide, t-amyl peroxy-2-ethylhexanoate, di-tert-butyl peroxide six hydrogen terephthalate, t-amyl peroxy-3,5,5-tri-methyl hexanoic acid ester, 3-hydroxyl-1,1-dimethylbutyl new decanoate ester peroxide, 1,1,3,3-tetramethyl butyl peroxidation-2-ethylhexanoate, t-amyl peroxy neodecanoic acid ester, t-amyl peroxy-2-ethylhexanoate, peroxidation two (3-toluyl), dibenzoyl peroxide, peroxidation two (4-toluyl), uncle's hexyl peroxidation sec.-propyl monocarbonate, the tert-butyl hydroperoxide maleic acid ester, tert-butyl hydroperoxide-3,5,5-tri-methyl hexanoic acid ester, the tert-butyl hydroperoxide laurate, 2,5-dimethyl-2,5-two (peroxidation of 3-toluyl) hexane, tert-butyl hydroperoxide-2-ethylhexyl monocarbonate, uncle's hexyl peroxide benzoate, 2,5-dimethyl-2,5-two (benzoyl peroxidation) hexane, tert butyl peroxy benzoate, dibutyl peroxidation trimethyladipic acid ester, t-amyl peroxy n-caprylic acid ester, the different nonenoate of t-amyl peroxy, the organo-peroxides such as t-amyl peroxy benzoic ether; 2,2 '-azo two-2,4-methyl pentane nitrile, 1,1 '-azo two (1-acetoxyl group-1-diphenylphosphino ethane), 2,2 '-Diisopropyl azodicarboxylate, 2,2 '-azo two (2-methylbutyronitrile), dimethyl-2,2 '-Diisopropyl azodicarboxylate, 4,4 '-azo two (4-cyanopentanoic acid), 1, the two azo-compounds such as (1-hexanaphthene formonitrile HCNs) of 1 '-azo etc.
These compounds both can use separately, also can compound use more than 2 kinds.
In addition, as (c) radical polymerization initiator, can use the compound that produces free radical by the rayed of 150～750nm.As such compound, for example, Photoinitiation, Photopolymerization, and Photocuring(is light-initiated, photopolymerization and photocuring), J.-P.Fouassier, Hanser Publishers (nineteen ninety-five, the α that puts down in writing among the p17～p35)-acetparaminosalol amphyl, phosphinoxide is to light-struck highly sensitive, therefore more preferably.
These compounds both can use separately, also can mix use with above-mentioned organo-peroxide, azo-compound.
The content of above-mentioned (c) radical polymerization initiator is preferably 0.1～500 mass parts with respect to (a) thermoplastic resin 100 mass parts, 1～300 mass parts more preferably, and more preferably 5～50 mass parts are particularly preferably 10～30 mass parts.If (c) content of radical polymerization initiator is lower than 0.1 mass parts, then adhesive composite tends to be difficult for solidifying fully, if surpass 500 mass parts, then stability in storage is tended to variation.
The vinyl compound (vinyl compound that contains phosphate) that has phosphate as (d) in the present embodiment; get final product so long as have the compound of phosphate and vinyl; be not particularly limited, more preferably have (methyl) acryl of at least more than one free-radical polymerised excellence in the molecule as phosphoric acid (methyl) acrylic compound of vinyl.As such compound, can enumerate the compound shown in the following general formula (M)～(O).
[changing 17]
Figure BDA00003327258900191
[in the formula (M), R 15Expression (methyl) acryloxy, R 16Expression hydrogen atom or methyl, k and l represent 1～8 integer independently of one another.In addition, in the formula, R 15Each other, R 16Each other, k is identical or different each other with l each other.]
[changing 18]
[in the formula (N), R 17Expression (methyl) acryloxy, m and n represent 1～8 integer independently of one another.In addition, in the formula, R 17Each other, m is identical or different each other with n each other.]
[changing 19]
Figure BDA00003327258900202
[in the formula (O), R 18Expression (methyl) acryloxy, R 19Expression hydrogen atom or methyl, o and p represent 1～8 integer independently of one another.In addition, in the formula, R 19Identical or different each other with o each other.]
The vinyl compound that contains phosphate as (d), particularly, can enumerate acid phosphate oxygen base ethyl (methacrylic ester) (acid phosphor oxy ethyl methacrylate), acid phosphate oxygen base ethyl propylene acid esters, acid phosphate oxygen base propyl group (methacrylic ester), acid phosphate oxygen base polyoxyethylene glycol monomethacrylates, acid phosphate oxygen base polyoxy propylene glycol monomethyl acrylate, 2,2 '-two (methyl) acryloxy diethyl phosphoric acid ester, EO modified phosphate two (methacrylic ester), the phosphoric acid modification epoxy acrylate, phosphoric acid vinyl acetate etc.
(d) in the adhesive composite contains the content of the vinyl compound of phosphate, with the content of (b) free-radical polymerised compound except the vinyl compound that contains phosphate independently, with respect to (a) thermoplastic resin 100 mass parts, be preferably 0.2～300 mass parts, 1～200 mass parts more preferably, more preferably 1～50 mass parts is particularly preferably 1～10 mass parts.Be lower than 0.2 mass parts if (d) contain the content of the vinyl compound of phosphate, then tend to be difficult for obtaining high-adhesive-strength, if surpass 300 mass parts, the physical property of the adhesive composite after then solidifying is tended to easy reduction, is difficult for guaranteeing reliability.
(e) electroconductive particle that the adhesive composite of present embodiment is contained is so long as its whole or surface has the particle of electroconductibility gets final product, but in the situation about using in the connection of the circuit block with splicing ear, preferred median size is less than distance between splicing ear.
As (e) electroconductive particle, can enumerate the metallics of Au, Ag, Ni, Cu, scolder etc., carbon etc.In addition, also can be with dielectric glass, pottery, plastics etc. as nuclear, the above-mentioned metal of coating, metallics, carbon on this nuclear and material.As nuclear with plastics at (e) electroconductive particle, at the above-mentioned metal of coating, metallics, carbon on this nuclear and material or the situation of hot molten metal particle under, owing to have deformability by heating and pressurizing, therefore when connecting with the contact area increase of electrode, Reliability Enhancement, thereby be preferred.
In addition, the surface of these (e) electroconductive particles further with the coating such as macromolecule resin particulate, can suppress when increasing the content of electroconductive particle to be contacted with each other by particle caused short circuit, improve the insulativity between telegraph circuit, therefore can suitably it be used separately or mix use with (e) electroconductive particle.
About the median size of this (e) electroconductive particle, from viewpoint dispersed, electroconductibility, be preferably 1～18 μ m.In the situation that contains such (e) electroconductive particle, adhesive composite can preferably use as anisotropic conductive adhesive.
Content to (e) electroconductive particle in the adhesive composite is not particularly limited, and is preferably 0.1～30 volume % with respect to the adhesive composite cumulative volume, more preferably 0.1～10 volume %.If its value is lower than 0.1 volume %, then electroconductibility is tended to reduce, if surpass 30 volume %, then easy generation is tended in the short circuit of circuit.In addition, volume % depends on the volume of each composition that 23 ℃ curing is front, but the volume of each composition can utilize proportion to be converted into volume by weight.In addition, also can add therein this composition by in graduated cylinder etc., being added in the appropriate solvent (water, alcohol etc.) that can make this composition good wet in the situation that does not make this composition dissolving or swelling, the volume that increased is obtained as the volume of this composition.
In addition, about the adhesive composite of present embodiment, in order to control curing speed, to give stability in storage, can add stablizer.Stablizer as such is not particularly limited, and can use known compound, is preferably the quinone derivatives such as benzoquinones, quinhydrones; The amphyls such as 4-methoxyphenol, 4-tert-butyl catechol; 2,2,6,6-tetramethyl piperidine-1-oxygen base, 4-hydroxyl-2,2,6, the 6-tetramethyl piperidine-amino oxygen radical derivatives such as 1-oxygen base; The hindered amine derivatives such as tetramethyl-piperidyl methacrylic ester etc.
The content of stablizer is preferably 0.01～30 mass parts with respect to adhesive composite 100 mass parts, more preferably 0.05～10 mass parts.Be lower than at content in the situation of 0.01 mass parts, wayward curing speed, be difficult for giving stability in storage, surpassing in the situation of 30 mass parts, easily to bringing detrimentally affect with the consistency of other composition.
In addition, can in the adhesive composite of present embodiment, suitably add bonding auxiliary agents such as coupling agent, adaptation improving agent and flow agent take alkoxyl silicone alkane derivatives, silazane derivative as representative.As coupling agent, particularly, the compound shown in the preferred following general formula (P).Bonding auxiliary agent both can use separately also and can compound use more than 2 kinds.
[changing 20]
Figure BDA00003327258900221
[in the formula (P), R 20, R 21And R 22Represent independently of one another the alkyl of hydrogen atom, carbonatoms 1～5, the alkoxyl group of carbonatoms 1～5, alkoxy carbonyl or the aryl of carbonatoms 1～5, R 23Expression (methyl) acryl, vinyl, isocyanate group, imidazolyl, sulfydryl, amino, methylamino, dimethylamino, benzylamino, phenyl amino, cyclohexyl amino, morpholinyl, piperazinyl, urea groups or glycidyl, q represents 1～10 integer.]
The adhesive composite of present embodiment in order to relax stress and to improve cementability, can merge the use rubber constituent.The composition that rubber constituent refers to show the composition of caoutchouc elasticity (JIS K6200) under state originally or shows caoutchouc elasticity by reaction.Rubber constituent both can be that solid also can be liquid in room temperature (25 ℃), from improving mobile viewpoint preferred liquid.As rubber constituent, preferably has the compound of polyhutadiene skeleton.Rubber constituent can have cyano group, carboxyl, hydroxyl, (methyl) acryl or morpholinyl.In addition, from improving the viewpoint of cementability, preferred side chain or the terminal cyano group as high polar group, the rubber constituent of carboxyl of comprising.In addition, even have the compound of polyhutadiene skeleton, in the thermoplastic situation of demonstration, be classified into (a) thermoplastic resin, in the free-radical polymerised situation of demonstration, be classified into (b) free-radical polymerised compound.
As rubber constituent; particularly; can enumerate polyisoprene; polyhutadiene; carboxy terminated polybutadiene; hydroxy-terminated polybutadienes; 1; the 2-polyhutadiene; end carboxyl 1; the 2-polyhutadiene; terminal hydroxy group 1, the 2-polyhutadiene; acrylic rubber; styrene-butadiene rubber(SBR); end hydroxy styrene-butadiene rubber; paracril; polymer ends contains carboxyl; hydroxyl; the paracril of (methyl) acryl or morpholinyl; carboxylated nitrile rubber; terminal hydroxy group gathers (oxypropylene); end alkoxysilyl poly-(oxypropylene); poly-(oxygen butylidene) glycol; polyolefin diols etc.
In addition; as above-mentionedly having high polar group, at room temperature being the rubber constituent of liquid; particularly; can enumerate liquid acrylonitrile butadiene rubber, contain liquid acrylonitrile butadiene rubber, the carboxylated nitrile rubber of liquid of carboxyl, hydroxyl, (methyl) acryl or morpholinyl etc. in polymer ends, be preferably 10～60 quality % as the acrylonitrile content of polar group.
These rubber constituents both can have been used separately also and can compound use more than 2 kinds.
In addition, in order to relax stress and to improve cementability, also can in the adhesive composite of present embodiment, add organic fine particles.The median size of organic fine particles is preferably 0.05～1.0 μ m.In addition, comprise at organic fine particles in the situation of above-mentioned rubber constituent, not being to be categorized into organic fine particles but to be categorized into rubber constituent, comprising at organic fine particles in the situation of above-mentioned (a) thermoplastic resin, is not to be categorized into organic fine particles but to be categorized into (a) thermoplastic resin.
As organic fine particles; particularly; can enumerate by polyisoprene; polyhutadiene; carboxy terminated polybutadiene; hydroxy-terminated polybutadienes; 1; the 2-polyhutadiene; end carboxyl 1, the 2-polyhutadiene; acrylic rubber; styrene-butadiene rubber(SBR); paracril; polymer ends contains carboxyl; hydroxyl; the paracril of (methyl) acryl or morpholinyl; carboxylated nitrile rubber; terminal hydroxy group gathers (oxypropylene); end alkoxysilyl poly-(oxypropylene); poly-(oxygen butylidene) glycol; polyolefin diols (methyl) alkyl acrylate-butadiene-styrene copolymer; the organic fine particles that (methyl) alkyl acrylate-Organosiliconcopolymere or organosilicon (methyl)-acrylic copolymer or complex body form.
These organic fine particles both can use separately also can merge use by compound more than 2 kinds.
The elongation at break of the adhesive composite of present embodiment is preferably 300～500%, and more preferably 300～450%.By making elongation at break in above-mentioned scope, can give flexible fully, even have the adherend (polyimide, PET, PC, PEN etc.) of organic substrate, also can follow their distortion, and can improve bonding strength between the circuit block, obtain excellent connection reliability.If it is flexible fully that elongation at break less than 300%, then can not be given, tend to be difficult for following the distortion of adherend, if greater than 500%, then flexible excessive, the bonding strength between the circuit block is tended to easy reduction.
Think that elongation at break can adjust by using by urethane (methyl) acrylate of the glycol gained of the vulcabond of fatty family or fragrant family and fatty family.For example, if make above-mentioned urethane (methyl) acrylate to contain quantitative change many, then elongation at break tends to become large.In addition, large if the weight-average molecular weight of above-mentioned urethane (methyl) acrylate becomes, then elongation at break also tends to become large.In addition, if weight-average molecular weight height and the Tg of thermoplastic resin are low, then elongation at break tends to become large.In addition, when the shared ratio of above-mentioned urethane (methyl) acrylate in the free-radical polymerised compound was high, it is large that elongation at break tends to become.In addition, when adding rubber constituent, it is large that elongation at break tends to become.In addition, if the content of organic fine particles, mineral filler is low, then elongation at break tends to become large.
The adhesive composite of present embodiment is preferably 0.5～5MPa 200 ℃ storage modulus, more preferably 0.5～3.5MPa.Think that by making 200 ℃ storage modulus in above-mentioned scope can have fully flexible and cross-linking density concurrently, the stress at the adherend of adhesive composite and adhesive composite interface obtains relaxing.Therefore, the bonding strength between the circuit block is improved, even and also can keep stable performance after the reliability test for a long time.If storage modulus less than 0.5MPa or greater than 5MPa, then tends to be difficult for having concurrently sufficient strength of joint and good connection reliability.
The adhesive composite of present embodiment is in the situation of liquid, can use with pasty state at normal temperatures.At room temperature be in the situation of solid, both can heat rear use, also can use the solvent gelatinization.As operable solvent, preferably do not have reactivity with adhesive composite and additive and show sufficient deliquescent solvent, preferably the boiling point under normal pressure is 50～150 ℃ solvent.Be lower than at boiling point in 50 ℃ the situation, if at room temperature place, then probably volatilization is tended to be difficult to use in open system.In addition, if boiling point surpasses 150 ℃, then be difficult to make solvent evaporates, often the reliability after bonding brought detrimentally affect.
In addition, the adhesive composite of present embodiment also can form membranaceous use.Can with in adhesive composite as required by adding solution coat that the modes such as solvent obtain on the separability base materials such as fluororesin film, polyethylene terephthalate film, release paper, or make the base materials such as mentioned solution immersion non-woven fabrics and be positioned on the separability base material, desolventizing etc. and using as film.If adhesive composite is used with the shape of film, be more convenient from viewpoints such as operability then.
The adhesive composite of present embodiment can merge the use heating and pressurization makes it bonding.Heating temperature is preferably 100～200 ℃ temperature.Pressure preferably in the scope to the adherend injury not, generally is preferably 0.1～10MPa.These heating and pressurization are preferably carried out in 0.5 second～120 seconds scope, also can make it bonding under 120～190 ℃, 3MPa, 10 seconds heating.
The caking agent that the adhesive composite of present embodiment can be used as the different xenogenesis adherend of thermal expansivity uses.Particularly, the circuit connection material, the CSP that can be used as take anisotropically conducting adhesive, silver-colored thickener, silverskin etc. as representative use with the semiconductor element adhesives as representative such as underfill, LOC adhesive tape with elastomerics, CSP.
(the 2nd embodiment)
In addition, the adhesive composite that the 2nd embodiment of the present invention relates to is characterised in that, it is for the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea, comprise (a) thermoplastic resin, (b) free-radical polymerised compound and (c) radical polymerization initiator, (b) free-radical polymerised compound contains urethane (methyl) acrylate, and elongation at break is 300～500%.
Contain above-mentioned each composition by the adhesive composite that above-mentioned the 2nd embodiment is related to, (b) free-radical polymerised compound contains urethane (methyl) acrylate, elongation at break is 300～500%, can give adhesive composite with flexible fully, follow the distortion of adherend (polyimide, PET, PC, PEN etc.), therefore can improve the bonding strength between the circuit block, obtain excellent connection reliability.The elongation at break of above-mentioned adhesive composite more preferably 300～450%.
In the adhesive composite that above-mentioned the 2nd embodiment relates to, about (a) thermoplastic resin and (c) radical polymerization initiator, use the same material of adhesive composite that relates to above-mentioned the 1st embodiment.In addition, (b) free-radical polymerised compound, although it is different being not particularly limited this aspect at the critical surface tension of contained urethane (methyl) acrylate, but the adhesive composite that relates to the 1st embodiment similarly, the critical surface tension of contained urethane (methyl) acrylate is preferably 20～40mN/m, more preferably 20～35mN/m, more preferably 20～33mN/m.In addition, about 200 ℃ storage modulus, the adhesive composite that also relates to above-mentioned the 1st embodiment similarly is preferably 0.5～5MPa, more preferably 0.5～3.5MPa.
The adhesive composite that above-mentioned the 2nd embodiment relates to, the adhesive composite that relates to the 1st embodiment similarly preferably comprises the vinyl compound that (d) has phosphate.The vinyl compound that has phosphate by comprising (d) can make adhesive composite that the cementability of metal base is improved.In addition, can obtain excellent bonding strength to the circuit block with the splicing ear that is consisted of by metal, ITO, IZO etc.
In addition, in the adhesive composite that above-mentioned the 2nd embodiment relates to, the adhesive composite that relates to the 1st embodiment similarly can add (e) electroconductive particle, stablizer, coupling agent, bonding auxiliary agent, rubber constituent and organic fine particles.
The adhesive composite that above-mentioned the 2nd embodiment relates to, about (a) thermoplastic resin, (b) free-radical polymerised compound and (c) radical polymerization initiator, preferably has the content of the same scope of the adhesive composite that relates to the 1st embodiment.In addition, in the situation of the vinyl compound, (e) electroconductive particle, stablizer, coupling agent, bonding auxiliary agent, rubber constituent and the organic fine particles that contain (d) and have phosphate, also preferably has the content of the same scope of the adhesive composite that relates to the 1st embodiment about these compositions.
The adhesive composite that the 1st embodiment of the present invention or the 2nd embodiment relate to is as using for the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea.Here, above-mentioned the first circuit block and/or above-mentioned second circuit parts are that the base material of the thermoplastic resin below 200 ℃ consists of by comprising second-order transition temperature preferably, and above-mentioned the first splicing ear and/or above-mentioned the second splicing ear preferably are made of ITO and/or IZO.Be thermoplastic resin below 200 ℃ as second-order transition temperature, be not particularly limited, for example can enumerate polyethylene terephthalate, polycarbonate and PEN etc.
Next, the syndeton body of the circuit block of the adhesive composite that used above-mentioned present embodiment described.Fig. 1 is the diagrammatic cross-section that shows an embodiment of syndeton body adhesive composite, circuit block that has used the present embodiment that does not contain (e) electroconductive particle.Fig. 2 is the diagrammatic cross-section that is presented at syndeton body the first circuit block, second circuit parts and the adhesive composite (not containing electroconductive particle) before of making circuit block shown in Figure 1.
The syndeton body 100 of circuit block shown in Figure 1 comprises: the interarea 31a of the first circuit substrate 31 have the first splicing ear 32 the first circuit block 30, have the second circuit parts 40 of the second splicing ear 42 at the interarea 41a of second circuit substrate 41, connect the interconnecting piece 10C of the interarea 41a of the interarea 31a of the first circuit substrate 31 and second circuit substrate 41 in the first splicing ear 32 mode relative with the second splicing ear 42.The first splicing ear 32 is electrically connected by contacting each other with the second splicing ear 42.In addition, interconnecting piece 10C comprises the cured article of the adhesive composite 10 of present embodiment.
The syndeton body 100 of circuit block shown in Figure 1 for example can followingly be made.
At first, as shown in Figure 2, prepare the first circuit block 30, second circuit parts 40 and be shaped to membranaceous adhesive composite 10.Next, adhesive composite 10 is placed on the interarea 41a that is formed with the second splicing ear 42 in the second circuit parts 40, then, on adhesive composite 10, place the first circuit block 30 in the first splicing ear 32 mode relative with the second splicing ear 42.Then, make its curing on one side across the first circuit block 30 and second circuit parts 40 caking agent compositions 10 on one side, simultaneously in the direction pressurization vertical with interarea 31a, 41a, between the first and second circuit blocks 30,40, form interconnecting piece 10C, thereby obtain the syndeton body 100 of the circuit block of Fig. 1.
Fig. 3 is the diagrammatic cross-section of an embodiment of syndeton body that shows the circuit block of the adhesive composite used the present embodiment that contains (e) electroconductive particle.Fig. 4 is the diagrammatic cross-section that is presented at syndeton body the first circuit block, second circuit parts and the adhesive composite (containing electroconductive particle) before of making circuit block shown in Figure 3.
The syndeton body 200 of circuit block shown in Figure 3 comprises: have the second circuit parts 40 that have the second splicing ear 42 on the interarea 41a of the first circuit block 30, second circuit substrate 41 of the first splicing ear 32 on the interarea 31a of the first circuit substrate 31, connect the interconnecting piece 20C of the interarea 41a of the interarea 31a of the first circuit substrate 31 and second circuit substrate 41 in the first splicing ear 32 mode relative with the second splicing ear 42.In addition, interconnecting piece 20C be in the composition except electroconductive particle 21 of adhesive composite, be dispersed with electroconductive particle 22 adhesive composite 20 cured article (namely, in the cured article 21C of the composition except electroconductive particle of adhesive composite, be dispersed with the material of electroconductive particle 22), between relative the first splicing ear 32 and the second splicing ear 42, by electroconductive particle 22 is contacted with two splicing ears, two splicing ears are electrically connected by electroconductive particle 22 thereby be situated between.
The syndeton body 200 of circuit block shown in Figure 3, for example as shown in Figure 4, can be by preparing the first circuit block 30, second circuit parts 40 and be shaped to membranaceous adhesive composite 20, utilize with the same methods of the syndeton body 100 that obtains above-mentioned circuit block and make.
Here, at least one in the first circuit block 30 and the second circuit parts 40 is that the base material of the thermoplastic resin below 200 ℃ consists of by second-order transition temperatures such as containing polyethylene terephthalate, polycarbonate and PEN preferably.That is, to contain the second-order transition temperatures such as polyethylene terephthalate, polycarbonate and PEN be thermoplastic resin below 200 ℃ at least one in preferred the first circuit substrate 31 and the second circuit substrate 41.If at least one in the first circuit block 30 and the second circuit parts 40 is the circuit block that consists of by containing the base material that is selected from least a kind of material in polyethylene terephthalate, polycarbonate and the PEN, then can improve the wettability with adhesive composite, further improve bonding strength.Therefore, the syndeton body of such circuit block can obtain more excellent connection reliability.
In addition, one or two in the first circuit block 30 and the second circuit parts 40 can be that the base material of the thermoplastic resin below 200 ℃ consists of by second-order transition temperatures such as not containing polyethylene terephthalate, polycarbonate and PEN.As the base material that forms such circuit block, can use inorganicss such as comprising semi-conductor, glass, pottery base material, comprise the organic base material such as polyimide, make the inorganics such as glass/epoxy and organism make up the base material etc. of gained.
In addition, at least one in the first splicing ear 32 and the second splicing ear 42 preferably is made of the a kind of institute that is selected among ITO and the IZO at least.ITO and IZO are owing to easy etching and pattern excellent in workability, therefore preferably as splicing ear.And, by using the adhesive composite of present embodiment, can suppress fully the corrosion of the splicing ear that consisted of by ITO and/or IZO.
In addition, one or two in the first splicing ear 32 and the second splicing ear 42 can be made of the material except ITO and IZO.As such splicing ear, can use the splicing ear that comprises copper, silver, aluminium, gold, palladium, nickel and their metals such as alloy.
In addition, the adhesive composite of the present embodiment of using as interconnecting piece does not need to solidify fully (curing of the topnotch that can reach) under the regulation condition of cure, as long as produce above-mentioned characteristic, can be partly solidified state.
Embodiment
Below, specifically describe the present invention based on embodiment, but the present invention is not limited to this.
＜thermoplastic resin＞
(preparation of PAUR)
Polyester urethane resin (Co., Ltd.'s system is spun by Japan, UR-8200 (trade(brand)name)) has used the methyl ethyl ketone of resin Composition 30 quality % and the 1:1 mixed solvent dissolving product of toluene.
(preparation of phenoxy resin)
Phenoxy resin (Toto Kasei KK's system, YP-50 (trade(brand)name)) is that resin 40 mass parts are dissolved in the solution of making solids component 40 quality % in methyl ethyl ketone 60 mass parts.
(preparation of vinyl-vinyl acetate copolymer)
Vinyl-vinyl acetate copolymer (Mitsui Du Pont polymerization length of schooling, EV40W (trade(brand)name)) has used the toluene dissolving product of resin Composition 30 quality %.
＜free-radical polymerised compound＞
(synthesizing of urethane acrylate (UA1))
Possessing stirrer, thermometer, the reflux cooling pipe that possesses calcium chloride tube, add vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles) in the reaction vessel of nitrogen ingress pipe, Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, poly-(1 of number-average molecular weight 1000,6-hexylene glycol carbonic ether) (trade(brand)name: DURANOL T5652, Asahi Chemical Corp's system) 2000 mass parts (2.00 moles), dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably hydrogenated diphenyl methane diisocyanate (trade(brand)name: VESTANAT H through 3 hours 12MD, Degussa company system) 787 mass parts (3.00 moles), make its reaction.After dripping end, make its reaction 11 hours, measure by IR and confirm that isocyanic ester disappears, the end reaction, thus obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA1) is 24mN/m, and weight-average molecular weight is 13500, and viscosity is 2500Pas.
(synthesizing of urethane acrylate (UA2))
Possessing stirrer, thermometer, the reflux cooling pipe that possesses calcium chloride tube, be added into vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles) in the reaction vessel of nitrogen ingress pipe, Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, poly-(1 of number-average molecular weight 1000,6-hexylene glycol carbonic ether) (trade(brand)name: DURANOL T5652, Asahi Chemical Corp's system) 1000 mass parts (2.00 moles), dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably hydrogenated diphenyl methane diisocyanate (trade(brand)name: VESTANAT H through 3 hours 12MD, Degussa company system) 787 mass parts (3.00 moles), make its reaction.After dripping end, make its reaction 13 hours, measure by IR and confirm that isocyanic ester disappears, the end reaction, thus obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA2) is 23mN/m, and weight-average molecular weight is 15500, and viscosity is 4100Pas.
(synthesizing of urethane acrylate (UA3))
Possessing stirrer, thermometer, the reflux cooling pipe that possesses calcium chloride tube, be added into vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles) in the reaction vessel of nitrogen ingress pipe, Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, the polycaprolactone glycol of number-average molecular weight 2000 (trade(brand)name: Placcel220, Daisel chemical industry Co., Ltd's system) 4000 mass parts (2.00 moles), dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably isophorone diisocyanate (Aldrich Co., Ltd. system) 666 mass parts (3.00 moles) through 3 hours, make its reaction.After dripping end, make its reaction 12 hours, measure by IR and confirm that isocyanic ester disappears, the end reaction, thus obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA3) is 27mN/m, and weight-average molecular weight is 13800, and viscosity is 650Pas.
(synthesizing of urethane acrylate (UA4))
Possessing stirrer, thermometer, possessing in the reaction vessel of reflux cooling pipe, nitrogen ingress pipe of calcium chloride tube, with the 3-methyl isophthalic acid, 5-pentanediol 1650 mass parts (14 moles) and sebacic acid 2023 mass parts (10 moles) add in the reactor, under normal pressure, import fully nitrogen, then at about 170 ℃ the water that generates distilled in the system on one side and remove, Yi Bian carry out esterification.Become moment below the 0.3mgKOH/g at the acid number of polyester, by the vacuum pump vacuum tightness that little by little raises, reaction is finished.The polyester glycol that obtains like this has number-average molecular weight 1000.
Then, possessing stirrer, thermometer, possessing in the reaction vessel of reflux cooling pipe, nitrogen ingress pipe of calcium chloride tube and add vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles), Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, polyester glycol 2000 mass parts (2.00 moles) of above-mentioned acquisition, dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably isophorone diisocyanate (Aldrich Co., Ltd. system) 666 mass parts (3.00 moles) through 3 hours, make its reaction.After dripping end, it was reacted about 15 hours, measure by IR and confirm that isocyanic ester disappears, finish to react, thereby obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA4) is 43mN/m, and weight-average molecular weight is 18500, and viscosity is 4800Pas.
(synthesizing of urethane acrylate (UA5))
Possessing stirrer, thermometer, the reflux cooling pipe that possesses calcium chloride tube, add vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles) in the reaction vessel of nitrogen ingress pipe, Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, the polytetramethylene ether glycol of number-average molecular weight 1000 (trade(brand)name: Baotugu Chemical Industrial Co., Ltd's system, TG1000) 2000 mass parts (2.00 moles), dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably isophorone diisocyanate (Aldrich Co., Ltd. system) 666 mass parts (3.00 moles) through 3 hours, make its reaction.After dripping end, its reaction was carried out 13 hours.Measure the affirmation isocyanic ester by IR and disappear, finish reaction, thereby obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA5) is 17mN/m, and weight-average molecular weight is 14500, and viscosity is 2900Pas.
(synthesizing of urethane acrylate (UA6))
Possessing stirrer, thermometer, possessing in the reaction vessel of reflux cooling pipe, nitrogen ingress pipe of calcium chloride tube, with the 3-methyl isophthalic acid, 5-pentanediol 1650 mass parts (14 moles) and sebacic acid 2023 mass parts (10 moles) add in the reactor, under normal pressure, import fully nitrogen, then at about 170 ℃ the water that generates distilled in the system on one side and remove, Yi Bian carry out esterification.Become moment below the 0.3mgKOH/g at the acid number of polyester, by the vacuum pump vacuum tightness that little by little raises, reaction is finished.The polyester glycol that obtains like this has number-average molecular weight 1000.
Then, possessing stirrer, thermometer, possessing in the reaction vessel of reflux cooling pipe, nitrogen ingress pipe of calcium chloride tube and add vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles), Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, polyester glycol 2500 mass parts (2.50 moles) of above-mentioned acquisition, dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably isophorone diisocyanate (Aldrich Co., Ltd. system) 666 mass parts (3.00 moles) through 3 hours, make its reaction.After dripping end, it was reacted about 17 hours, measure by IR and confirm that isocyanic ester disappears, finish to react, thereby obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA6) is 41mN/m, and weight-average molecular weight is 23500, and viscosity is 6800Pas.
(synthesizing of urethane acrylate (UA7))
Possessing stirrer, thermometer, possessing the polytetramethylene ether diol (trade(brand)name: Baotugu Chemical Industrial Co., Ltd's system, TG1000) 2500 mass parts (2.50 moles), dibutyltin dilaurate (Aldrich Co., Ltd. system) 5.53 mass parts of adding vinylformic acid 2-hydroxyl ethyl ester (Aldrich Co., Ltd. system) 238 mass parts (2.05 moles), Hydroquinone monomethylether (Aldrich Co., Ltd. system) 0.53 mass parts, number-average molecular weight 1000 in the reaction vessel of reflux cooling pipe, nitrogen ingress pipe of calcium chloride tube.Import fully nitrogen, then be heated to 70～75 ℃, dripped equably isophorone diisocyanate (Aldrich Co., Ltd. system) 666 mass parts (3.00 moles) through 3 hours, make its reaction.After dripping end, make its reaction 15 hours.Measure the affirmation isocyanic ester by IR and disappear, finish reaction, thereby obtained urethane acrylate.The critical surface tension of the urethane acrylate of gained (UA7) is 16mN/m, and weight-average molecular weight is 20400, and viscosity is 3500Pas.
(isocyanuric acid modification 2 functional acrylates' (M-215) preparations)
Prepare isocyanuric acid modification 2 functional acrylates (Toagosei Co., Ltd's system, M-215 (trade(brand)name)).
(preparation with vinyl compound (P-2M) of phosphate)
Prepare 2-(methyl) acryloxy ethyl phosphonic acid ester (trade(brand)name: lightester P-2M, Kyoeisha Chemical Co., Ltd.'s system).
＜radical polymerization initiator＞
Preparation is as the dibenzoyl peroxide (trade(brand)name: Nipar BW, Japan Oil Co's system) of radical polymerization initiator.
＜electroconductive particle＞
(making of electroconductive particle)
Polystyrene is arranged the nickel dam of thickness 0.2 μ m as the surface of particle of nuclear, at the gold layer of the arranged outside thickness 0.02 μ m of this nickel dam, thereby making the electroconductive particle of median size 10 μ m, proportion 2.5.
[embodiment 1～12 and comparative example 1～5]
, electroconductive particle 1.5 volume % are cooperated disperse, thereby obtained adhesive composite than cooperating thermoplastic resin, free-radical polymerised compound and radical polymerization initiator according to the solid masses shown in the table 2.Use coating unit that the adhesive composite of gained is coated on the fluororesin film of thickness 80 μ m, the thickness that obtains bond layer by 70 ℃, 10 minutes warm air dryings is the film-like adhesive composition of 20 μ m.
[table 2]
Figure BDA00003327258900321
(mensuration of elongation at break, storage modulus, contact resistance, bonding strength)
The film-like adhesive composition that makes embodiment 1～12 and comparative example 1～5 is between the flexible electric circuit board (FPC) of the copper circuit that has 500 live widths, 25 μ m, spacing 50 μ m, thickness 8 μ m on the polyimide film and the glass that is formed with the ITO thin layer of 0.2 μ m (between thickness 1.1mm, surface resistivity 20 Ω/).Use thermo-compression bonding device (type of heating: permanent pattern of fever, eastern Li Gongchengshe system) with its heating and pressurizing 10 seconds under 160 ℃, the condition of 3MPa, connect and relate to wide 2mm, thereby make linker.(after the test) is with the resistance value between the adjacent circuit of this linker of multitester measuring keep 240 hours after just bonding and in 85 ℃, the hot and humid groove of 85%RH after.Resistance value represents with the mean value of the resistance between 37 place's adjacent circuits.
In addition, spend the bonding strength that stripping methods are measured each linker according to JIS-Z0237 by 90, estimate.Here, the determinator of bonding strength uses the tensilon UTM-4 processed of Japan Baldwin Co., Ltd. (peeling rate 50mm/ minute, 25 ℃).
In addition, the following mensuration of the elongation at break of film-like adhesive composition: membranaceous adhesive composite was heating and curing 1 hour at 180 ℃, with Instron company prepared material trier " microtester5548 " (draw speed 50mm/ minute, 25 ℃) sample of gained is measured.In addition, the following mensuration of the storage modulus of film-like adhesive composition: membranaceous adhesive composite was heating and curing 1 hour at 180 ℃, with TA instrument company viscoelasticity analysis device processed " RSA-3 " (5 ℃/minute of heat-up rates, frequency 10Hz measures temperature-150～300 ℃) sample of gained is measured.The mensuration of elongation at break, storage modulus, contact resistance and the bonding strength of the film-like adhesive composition that as above carries out the results are shown in following table 3.
[table 3]
Figure BDA00003327258900331
The adhesive composite that is obtained by embodiment 1～7 contains (a), (b), (c) and (d) composition, comprise urethane (methyl) acrylate of the critical surface tension with specified range as the adhesive composite of (b) composition by use, compare with comparative example 1～5 with the embodiment 8～12 that has used the adhesive composite that comprises the outer critical surface tension of specified range, under 160 ℃ of Heating temperatures, after just bonding and at 85 ℃, keep (testing rear) after 240 hours in the hot and humid groove of 85%RH and all demonstrate the following good contact resistance of about 2.6 Ω and the above good bonding strength of 600N/m.In addition, the elongation at break of film-like adhesive composition and storage modulus also demonstrate good value.
On the other hand, the adhesive composite that is obtained by comparative example 1～5, after just bonding and in 85 ℃, the hot and humid groove of 85%RH, keep 240 hours after (after the test) all demonstrate low bonding strength.In addition, the adhesive composites that obtained by comparative example 4 and 5, in 85 ℃, the hot and humid groove of 85%RH, keep 240 hours after the contact resistance of (after the test) high, bonding strength is also low.In addition, the elongation at break of film-like adhesive composition or storage modulus also demonstrate good value, but demonstrate value less than good scope at comparative example 2 and 3 Fracture elongations, demonstrate value greater than good scope at comparative example 4 and 5 Fracture elongations.In addition, storage modulus also demonstrates value greater than good scope in comparative example 2 and 3.
In addition, the adhesive composite that is obtained by embodiment 8～12 contains (a), (b) and (c) composition, comprise urethane (methyl) acrylate as (b) composition, use has the adhesive composite of the elongation at break of specified range, thus, compare at extraneous comparative example 2～5 with elongation at break, the balance between contact resistance and the bonding strength is good.Therefore think that elongation at break by making adhesive composite is in specified range, even do not use urethane (methyl) acrylate of the critical surface tension with specified range, also can give to adhesive composite flexiblely, and can obtain the good characteristic of balance.
In addition, make embodiment 1,2,4,5 and 10 and the film-like adhesive composition of comparative example 5 on polyimide film, have the FPC of copper circuit of 80 live widths, 150 μ m, spacing 300 μ m, thickness 18 μ m with between the substrate of the Ag thickener circuit that is formed with live width 150 μ m, spacing 300 μ m, thickness 10 μ m on PET film (thickness 0.1mm, Tg120 ℃), PC film (thickness 0.1mm, Tg150 ℃) and pen film (thickness 0.1mm, the Tg160 ℃) film.Use thermo-compression bonding device (type of heating: permanent pattern of fever, eastern Li Gongchengshe system) with they heating and pressurizing 10 seconds under 150 ℃, the condition of 2MPa respectively, crimping relates to wide 2mm, thereby makes linker.
In addition, bonding strength and the aforesaid method of each linker are similarly measured.The mensuration of the bonding strength of the film-like adhesive composition that as above carries out the results are shown in following table 4.
[table 4]
Adhesive composite by embodiment 13～16 gained, to any base material, under 150 ℃ of Heating temperatures, after just bonding and in 85 ℃, the hot and humid groove of 85%RH, keep 240 hours after (after the test) all demonstrate the good bonding strength more than the 560N/m.Relative therewith, in comparative example 6, after just bonding and in 85 ℃, the hot and humid groove of 85%RH, keep 240 hours after (after the test), the bonding strength step-down.In addition, embodiment 17 is not as embodiment 13～16, improved bonding strength but compare with comparative example 6.
The industry utilizability
According to the present invention, even under the condition of cure of low temperature, also can obtain excellent bonding strength also can keep stable performance (bonding strength, contact resistance) afterwards in long reliability test (high temperature and humidity test) adhesive composite, the syndeton body that has used the circuit block of this adhesive composite, the manufacture method of syndeton body and the application of adhesive composite even can provide.
Nomenclature
10,20 is adhesive composite;
10C, 20C are interconnecting piece;
21 for not comprising the adhesive composite of electroconductive particle;
22 is electroconductive particle;
21C is the cured article that does not comprise the adhesive composite of electroconductive particle;
30 is the first circuit block;
31 is the first circuit substrate;
31a is interarea;
32 is the first splicing ear;
40 is the second circuit parts;
41 is the second circuit substrate;
41a is interarea;
42 is the second splicing ear;
100,200 is the syndeton body of circuit block.

Claims (37)

1. adhesive composite, it is the adhesive composite that has the second circuit parts of the second splicing ear on the first circuit block of having the first splicing ear on the interarea and the interarea for connecting,
Described adhesive composite contains (a) thermoplastic resin, (b) free-radical polymerised compound and (c) radical polymerization initiator,
Described (b) free-radical polymerised compound comprises urethane (methyl) acrylate,
Elongation at break is 300～500%.
2. adhesive composite according to claim 1 wherein, also contains the vinyl compound that (d) has phosphate.
3. adhesive composite according to claim 1 and 2, wherein, the critical surface tension of described urethane (methyl) acrylate is 20～40mN/m.
4. adhesive composite according to claim 1 and 2, wherein, the critical surface tension of described urethane (methyl) acrylate is 20～35mN/m.
5. adhesive composite according to claim 1 and 2, wherein, the critical surface tension of described urethane (methyl) acrylate is 20～33mN/m.
6. adhesive composite according to claim 1 and 2, wherein, described urethane (methyl) acrylate is that the condensation reaction by fatty family vulcabond and aliphatic diol obtains.
7. adhesive composite according to claim 6, wherein, described fatty family vulcabond is the fourth vulcabond, hexamethylene diisocyanate, lysinediisocyanate, 2-methylpentane-1, the 5-vulcabond, 3-methylpentane-1, the 5-vulcabond, 2,2,4-tri-methyl hexamethylene-1, the 6-vulcabond, 2,4,4-tri-methyl hexamethylene-1, the 6-vulcabond, isophorone diisocyanate, cyclohexyl diisocyanate, the hydrogenation of benzene dimethylene diisocyanate, hydrogenated diphenyl methane diisocyanate or hydrogenation Three methyl Benzene dimethylene diisocyanate.
8. adhesive composite according to claim 6, wherein, described aliphatic diol is: with ethylene glycol, propylene glycol, 1, the 2-propylene glycol, 1, ammediol, 1, the 3-butyleneglycol, 1, the 4-butyleneglycol, neopentyl glycol, 1, the 2-pentanediol, 1, the 4-pentanediol, 1, the 5-pentanediol, 2, the 4-pentanediol, 2-methyl-2, the 4-pentanediol, 2,4-dimethyl-2, the 4-pentanediol, 2,2,4-trimethylammonium-1, the 3-pentanediol, 1, the 2-hexylene glycol, 1, the 5-hexylene glycol, 1, the 6-hexylene glycol, 2, the 5-hexylene glycol, 2-ethyl-1, the 3-hexylene glycol, 2,5-dimethyl-2, the 5-hexylene glycol, 1, the 2-ethohexadiol, 1, the 8-ethohexadiol, 1, the 7-heptanediol, 1, the 9-nonanediol, 1, the 2-decanediol, 1, the 10-decanediol, 1, the 12-decanediol, dodecanediol, tetramethyl ethylene ketone, Isosorbide-5-Nitrae-butynediol, triethylene glycol, glycol ether, dipropylene glycol or cyclohexanedimethanol are saturated low-molecular-weight diol class, by the polycarbonate diol class of the described low-molecular-weight diol class more than at least a kind and carbonyl chloride reaction gained, to be selected from oxyethane with the described low-molecular-weight diol class more than at least a kind as initiator, propylene oxide, the polyether glycol class of at least a kind of addition polymerization gained in the Epicholorohydrin, with hexanodioic acid, 3-methyl hexanodioic acid, 2,2,5,5-tetramethyl-hexanodioic acid, toxilic acid, fumaric acid, succsinic acid, 2, the 2-dimethyl succinate, 2-Ethyl-2-Methyl succsinic acid, 2,3-dimethyl succinate, oxalic acid, propanedioic acid, Methylpropanedioic acid, ethyl malonic acid, butyl malonic acid, dimethyl malonic acid, pentanedioic acid, the 2-methylglutaric acid, the 3-methylglutaric acid, 2,2-dimethylated pentanedioic acid, 3, the 3-dimethylated pentanedioic acid, 2,4-dimethylated pentanedioic acid, pimelic acid, suberic acid, the polyester glycol class of the acid anhydrides dehydrating condensation gained of the diprotic acid of nonane diacid or sebacic acid or described diprotic acid; Perhaps with the polyester glycol class of cyclic ester compound ring-opening polymerization gained.
9. adhesive composite according to claim 1 and 2, wherein, the weight-average molecular weight of described urethane (methyl) acrylate is more than 12000 and is lower than 20000.
10. adhesive composite according to claim 1 and 2, wherein, the viscosity of described urethane (methyl) acrylate in the time of 25 ℃ is 600～4500Pas.
11. adhesive composite according to claim 1 and 2, wherein, the use level of described urethane (methyl) acrylate is 5～95 quality % take described adhesive composite total amount as benchmark.
12. adhesive composite according to claim 1 and 2, wherein, the vinyl compound that described (d) has phosphate is phosphoric acid (methyl) acrylic compound that has at least more than one (methyl) acryl in the molecule.
13. adhesive composite according to claim 1 and 2; wherein; phosphoric acid (methyl) acrylic compound that has at least more than one (methyl) acryl in the described molecule is the compound shown in the following general formula (M)～(O)
Figure FDA00003327258800021
In the formula (M), R 15Expression (methyl) acryloxy, R 16Expression hydrogen atom or methyl, k and l represent 1～8 integer independently of one another; In addition, in the formula, R 15Each other, R 16Each other, k is identical or different each other with l each other,
Figure FDA00003327258800031
In the formula (N), R 17Expression (methyl) acryloxy, m and n represent 1～8 integer independently of one another; In addition, in the formula, R 17Each other, m is identical or different each other with n each other,
Figure FDA00003327258800032
In the formula (O), R 18Expression (methyl) acryloxy, R 19Expression hydrogen atom or methyl, o and p represent 1～8 integer independently of one another; In addition, in the formula, R 19Identical or different each other with o each other.
14. adhesive composite according to claim 1 and 2, wherein, described (d) contains the content of the vinyl compound of phosphate, is 0.2～300 mass parts with respect to described (a) thermoplastic resin 100 mass parts.
15. adhesive composite according to claim 1 and 2, wherein, the content of described (b) free-radical polymerised compound is 50～250 mass parts with respect to described (a) thermoplastic resin 100 mass parts.
16. adhesive composite according to claim 1 and 2, wherein, the storage modulus in the time of 200 ℃ is 0.5～5MPa.
17. adhesive composite according to claim 1 and 2, wherein, the storage modulus in the time of 200 ℃ is 0.5～3.5MPa.
18. adhesive composite according to claim 1 and 2, wherein, described elongation at break is 300～450%.
19. adhesive composite according to claim 1 and 2, wherein, described (a) thermoplastic resin contains at least a kind of resin that is selected from the group that is comprised of phenoxy resin, urethane resin, polyester urethane resin, polyvinyl butyral resin, acrylic resin and polyimide resin.
20. adhesive composite according to claim 1 and 2, wherein, the weight-average molecular weight of described (a) thermoplastic resin is 5,000～150,000.
21. adhesive composite according to claim 1 and 2, wherein, the content of described (a) thermoplastic resin is 5～80 quality % take described adhesive composite total amount as benchmark.
22. adhesive composite according to claim 1 and 2, wherein, described (c) radical polymerization initiator is organo-peroxide or azo-compound.
23. adhesive composite according to claim 1 and 2, wherein, the content of described (c) radical polymerization initiator is 0.1～500 mass parts with respect to described (a) thermoplastic resin 100 mass parts.
24. adhesive composite according to claim 1 and 2 wherein, also contains (e) electroconductive particle.
25. a circuit connection material, it comprises each the described adhesive composite in the claim 1～24.
26. a film-like adhesive composition, it is that each the described adhesive composite in the claim 1～24 is formed membranaceous forming.
27. the syndeton body of a circuit block comprises: have the second circuit parts and the interconnecting piece that have the second splicing ear on first circuit block, interarea of the first splicing ear on the interarea,
Described the first circuit block is situated between with described second circuit parts and is disposed in described the first splicing ear mode relative with described the second splicing ear by described interconnecting piece, and described the first splicing ear and described the second splicing ear be electrically connected,
Described interconnecting piece is the cured article of each the described adhesive composite in the claim 1～24,
Described the first circuit block and/or described second circuit parts are that the base material of the thermoplastic resin below 200 ℃ consists of by comprising second-order transition temperature.
28. the syndeton body of a circuit block comprises: have the second circuit parts and the interconnecting piece that have the second splicing ear on first circuit block, interarea of the first splicing ear on the interarea,
Described the first circuit block is situated between with described second circuit parts and is disposed in described the first splicing ear mode relative with described the second splicing ear by described interconnecting piece, and described the first splicing ear and described the second splicing ear be electrically connected,
Described interconnecting piece is the cured article of each the described adhesive composite in the claim 1～24,
Described the first circuit block and/or described second circuit parts consist of by containing the base material that is selected from a kind of material in the group that is comprised of polyethylene terephthalate, polycarbonate and PEN at least.
29. the syndeton body of a circuit block comprises: have the second circuit parts and the interconnecting piece that have the second splicing ear on first circuit block, interarea of the first splicing ear on the interarea,
Described the first circuit block is situated between with described second circuit parts and is disposed in described the first splicing ear mode relative with described the second splicing ear by described interconnecting piece, and described the first splicing ear and described the second splicing ear be electrically connected,
Described interconnecting piece is the cured article of each the described adhesive composite in the claim 1～24.
30. according to claim 27 or the syndeton body of 28 described circuit blocks, wherein,
A circuit block in described the first circuit block or the described second circuit parts consists of by containing the base material that is selected from a kind of material in the group that is comprised of polyethylene terephthalate, polycarbonate and PEN at least,
Another circuit block in described the first circuit block or the second circuit parts is polyimide resin.
31. the manufacture method of the syndeton body of a circuit block comprises following operation:
The operation that the second circuit parts that have the second splicing ear on the first circuit block of having the first splicing ear on the interarea and the interarea are situated between and are disposed in described the first splicing ear mode relative with described the second splicing ear by each the described adhesive composite in the claim 1～24
With described adhesive composite heating, it is solidified, connect the operation of described the first circuit block and described second circuit parts.
32. the described adhesive composite of each in the claim 1～24 is as the application of circuit connection material, described circuit connection material is for the second circuit parts that have the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea.
33. application according to claim 32, wherein, described second-order transition temperature is that the thermoplastic resin below 200 ℃ is at least a kind of resin that is selected from the group that polyethylene terephthalate, polycarbonate and PEN form.
34. according to claim 32 or 33 described application, wherein, a circuit block in described the first circuit block or the described second circuit parts consists of by containing the base material that is selected from a kind of material in the group that polyethylene terephthalate, polycarbonate and PEN form at least
Another circuit block in described the first circuit block or the described second circuit parts is polyimide resin.
35. the application of the described adhesive composite of each in the claim 1～24 in the manufacturing of circuit connection material, described circuit connection material is for the second circuit parts that have the second splicing ear on the first circuit block that has the first splicing ear on the connection interarea and the interarea.
36. application according to claim 35, wherein, described second-order transition temperature is that the thermoplastic resin below 200 ℃ is at least a kind of resin that is selected from the group that polyethylene terephthalate, polycarbonate and PEN form.
37. according to claim 35 or 36 described application, wherein, a circuit block in described the first circuit block or the described second circuit parts consists of by containing the base material that is selected from a kind of material in the group that polyethylene terephthalate, polycarbonate and PEN form at least
Another circuit block in described the first circuit block or the described second circuit parts is polyimide resin.
CN2013102289914A 2010-07-26 2011-05-30 Adhesive composition, connection structure, method for producing connection structure, and use of adhesive composition Pending CN103351838A (en)

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