CN101541903B - Adhesive and connection structure using the same - Google Patents

Adhesive and connection structure using the same Download PDF

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Publication number
CN101541903B
CN101541903B CN200780043737.XA CN200780043737A CN101541903B CN 101541903 B CN101541903 B CN 101541903B CN 200780043737 A CN200780043737 A CN 200780043737A CN 101541903 B CN101541903 B CN 101541903B
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Prior art keywords
caking agent
methyl
resin
splicing ear
acrylate
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CN101541903A (en
Inventor
加藤木茂树
工藤直
伊泽弘行
白坂敏明
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Showa Denko Materials Co Ltd
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Hitachi Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
    • H05K3/323—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives by applying an anisotropic conductive adhesive layer over an array of pads
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/01—Dielectrics
    • H05K2201/0104—Properties and characteristics in general
    • H05K2201/0129—Thermoplastic polymer, e.g. auto-adhesive layer; Shaping of thermoplastic polymer

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Electric Connection Of Electric Components To Printed Circuits (AREA)
  • Combinations Of Printed Boards (AREA)
  • Wire Bonding (AREA)
  • Conductive Materials (AREA)

Abstract

Disclosed is an adhesive containing a thermoplastic resin (a), a radically polymerizable compound (b), a urea compound (c) represented by the general formula (10) below, a radical polymerization initiator (d), and an acidic compound (e).

Description

The syndeton body of caking agent and this caking agent of use
Technical field
The present invention relates to the syndeton body of caking agent and this caking agent of use.
Background technology
For the purpose of the various parts combinations that make composed component, in semiconductor element and liquid crystal display device, use caking agent always.This caking agent at first requires to satisfy cementability, and requires to satisfy the very many-sided characteristics such as reliability under thermotolerance, the humid tropical condition.In addition, as caking agent was suitable for by sticky object, can use the organic substrates such as printed circuit board (PCB) or polyimide, and can use and have by the metals such as copper, aluminium or ITO, SiN, SiO 2Base material etc. the formed surface of various materials.Therefore, in caking agent, need to variously be carried out molecular designing by sticky object for described.
In the past, as the caking agent of semiconductor element or used for liquid crystal display element, extensively adopted the thermosetting resin (for example, with reference to patent documentation 1) that has used the Resins, epoxy that demonstrates high adhesion and high reliability.As the constituent of the caking agent that uses Resins, epoxy, usually use Resins, epoxy, have the solidifying agent such as reactive phenol resins with Resins, epoxy, promote the hot potentiality catalyzer that Resins, epoxy and solidifying agent react.Hot potentiality catalyzer has consisted of the important factor that determines solidification value and curing speed, and the curing speed viewpoint the when stability in storage under the room temperature and heating considers, can use various compounds.Condition of cure in the actual operation is by being to heat about 1～3 hour under 170～250 ℃ the temperature.
Yet, along with the high-precision refinement of highly integrated, the liquid crystal cell of recent semiconductor element, because interelement and narrow and smallization of wiring closet spacing, and the heating when solidifying, thereby circumferential component produced dysgenic possibility improve.In addition, in order to reduce cost, also need to improve turnout.Therefore, require under lower temperature and in the shorter time, to be cured, that is to say, require bonding under low temperature fast setting condition.In order to realize this low temperature fast setting, need to use the low hot potentiality catalyzer of activation energy, but the known stability in storage that has low temperature rapidly-curable and near room temperature concurrently is very difficult.
Therefore, recently, and receive publicity with the free-radical polymerised compound such as acrylate derivative or methacrylate derivative with as the radical-curable caking agent of the superoxide of radical polymerization initiator.Radically curing, 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.But because the radical-curable caking agent, the cure shrinkage during curing is large, therefore compares with the situation of using Resins, epoxy, and it has the tendency that bonding strength reduces.Therefore, in order to improve the bonding strength of radical-curable caking agent, proposed and as the method for free-radical polymerised compound (for example to have given flexibility and flexual ammonia ester acrylic compound by ehter bond, with reference to patent documentation 3,4), and the method (for example, with reference to patent documentation 5,6) of also using free-radical polymerised compound, phosphoric acid methacrylic ester and melamine resin.
Patent documentation 1: Unexamined Patent 1-113480 communique
Patent documentation 2: JP 2002-203427 communique
Patent documentation 3: specially permit communique No. 3522634
Patent documentation 4: JP 2002-285128 communique
Patent documentation 5: JP 2003-89775 communique
Patent documentation 6: JP 2003-20464 communique
Summary of the invention
The problem that invention will solve
Yet, use the radical-curable caking agent of above-mentioned ammonia ester acrylate, although its initial stage bonding strength is good, when being exposed to hot and humid environment, have the problem that the characteristics such as bonding strength, contact resistance reduce.In addition, according to the inventor's etc. research as can be known, use the caking agent of phosphoric acid methacrylic ester and melamine resin, stability in storage is not enough, and when using after prolonged preservation, can't obtain enough bonding strengths, contact resistance.
Therefore, the object of the invention is to provide a kind of high-adhesive-strength that shows, and simultaneously has high patience for the reliability test hot and humid under, and then the also radical-curable caking agent of excellence of stability in storage, and the syndeton body that uses this caking agent.
The means of dealing with problems
Caking agent of the present invention contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) by the represented urea compounds of following general formula (10), (d) radical polymerization initiator and (e) acidic cpd.In the formula (10), R 1And R 2Independent expression can have substituent alkyl or hydrogen atom, R separately 1And R 2Also can interosculate and form ring, R 3And R 4Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.
[changing 1]
Figure G200780043737XD00031
The caking agent of the invention described above owing to adopted the combination of above-mentioned special component, therefore shows high-adhesive-strength, have high patience for the reliability test under hot and humid simultaneously, and then stability in storage is also excellent.
Syndeton body of the present invention possesses: have the first splicing ear the first circuit block, have the second splicing ear and according to making this second splicing ear mode relative with described the first splicing ear and the second circuit parts of the relative configuration of described the first circuit block and between described the first circuit block and described second circuit parts and the adhesive linkage that they are bonding.This adhesive linkage is formed by the caking agent of the invention described above.
The syndeton body of the invention described above, with high-adhesive-strength that circuit block is bonding each other, have high patience for the reliability test under hot and humid simultaneously.
The invention effect
According to the present invention, a kind of radical-curable caking agent is provided, it shows high-adhesive-strength, has high patience for the reliability test under hot and humid simultaneously, and then stability in storage is also excellent.
In addition, according to the present invention, provide a kind of syndeton body, it is bonding each other with circuit block with high-adhesive-strength, has high patience for the reliability test under hot and humid simultaneously.
Description of drawings
Fig. 1 is the pattern sectional view of an embodiment of expression syndeton body.
Nomenclature
1... syndeton body, 7... electroconductive particle, 10... adhesive linkage, 11... insulation layer, 20... the first circuit block, 21... the first circuit substrate, 22... the first splicing ear, 30... second circuit parts, 31... second circuit substrate, 32... the second splicing ear.
Embodiment
Below, preferred implementation of the present invention is elaborated.But the present invention is not limited to following embodiment.
The caking agent of present embodiment contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) urea compounds, (d) radical polymerization initiator and (e) acidic cpd.Caking agent of the present invention for example can be preferably used as, and is mutually bonding for the circuit block that will have splicing ear, and forms the anisotropically conducting adhesive of syndeton body.
Thermoplastic resin as (a) composition is not particularly limited, and can use known material.For example, can use phenoxy resin, vibrin, urethane resin, polyester urethane resin, butyral resin (butyral resin), acrylic resin, polyimide resin, polyamide resin, poly-(methyl) esters of acrylic acid, polyvinyl butyral acetal class or vinyl-vinyl acetate copolymer as thermoplastic resin.Particularly, the thermoplastic resin in the caking agent preferably comprises at least a from the group that phenoxy resin, vibrin, urethane resin, polyester urethane resin, butyral resin, acrylic resin and polyimide resin form.They can use separately, or are used in combination more than 2 kinds.
Thermoplastic resin can have siloxane bond or contain the substituting group of fluorine atom.As long as these thermoplastic resins are when mixing with other composition, mix fully or microphase-separated occurs and the material of gonorrhoea then can particularly preferably use.
The molecular weight of thermoplastic resin is larger, and the easier film-forming properties that obtains then simultaneously, can be set as wide range as the melt viscosity of the flowability of caking agent with impact.Specifically, the weight-average molecular weight of thermoplastic resin is preferably 5000～500000, and more preferably 10000～100000.If weight-average molecular weight, then has the tendency that film-forming properties reduces less than 5000, and if it surpasses 500000, then have the tendency that the intermiscibility with other composition reduces.
As the free-radical polymerised compound of (b) composition, so long as have free-radical polymerised functional group's compound, then be not particularly limited, can use known material.For example, can use styrene derivatives, polymer maleimides and have acryl or methacryloyl (below, be called " (methyl) acryl ".) compound.Wherein, free-radical polymerised compound preferably comprises multifunctional (methyl) acrylic compound with (methyl) acryl more than 2.
Preferred object lesson as multifunctional (methyl) acrylate, can enumerate epoxy (methyl) origoester acrylate, ammonia ester (methyl) origoester acrylate, the oligopolymer such as polyethers (methyl) origoester acrylate and polyester (methyl) origoester acrylate, trimethylolpropane tris (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, polyalkylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, tricarbimide modification 2 officials energy (methyl) acrylate, tricarbimide modification 3 officials energy (methyl) acrylate, make epoxy (methyl) acrylate of the glycidyl addition gained of (methyl) vinylformic acid and bisphenol fluorene diglycidylether, (methyl) acryloxy is directed in the compound of the glycidyl addition gained that makes ethylene glycol or propylene glycol and bisphenol fluorene diglycidylether and the compound that obtains, and following general formula (A) or (B) represented multifunctional (methyl) acrylic compound such as compound.These multifunctional (methyl) acrylic compound can use separately as required, or be used in combination more than 2 kinds.
[changing 2]
Figure G200780043737XD00051
In the formula (A), R 21And R 22Represent independently of one another hydrogen atom or methyl, k and m represent 1～8 integer independently of one another.In the formula (B), R 23And R 24Represent independently of one another hydrogen atom or methyl, n represents 1～8 integer, and p represents 0～8 integer.
In order to improve flowability, as (b) composition, also may be used multifunctional (methyl) acrylic compound and simple function (methyl) acrylic compound.By using simple function (methyl) acrylic compound, improved the flowability of caking agent.Object lesson as simple function (methyl) acrylic compound; can enumerate tetramethylolmethane (methyl) acrylate; 2-cyano ethyl (methyl) acrylate; cyclohexyl (methyl) acrylate; dicyclopentenyl (methyl) acrylate; two cyclopentenes oxygen base ethyl (methyl) acrylate; 2-(2-ethoxy ethoxy) ethyl (methyl) acrylate; 2-ethoxyethyl group (methyl) acrylate; 2-ethylhexyl (methyl) acrylate; n-hexyl (methyl) acrylate; 2-hydroxyethyl (methyl) acrylate; hydroxypropyl (methyl) acrylate; isobornyl (methyl) acrylate; isodecyl (methyl) acrylate; iso-octyl (methyl) acrylate; dodecyl (methyl) acrylate; 2-methoxy ethyl (methyl) acrylate; 2-phenoxy group ethyl (methyl) acrylate; tetrahydrofurfuryl (methyl) acrylate; N; N-dimethyl aminoethyl (methyl) acrylate; N; N-dimethyl aminoethyl (methyl) acrylate; N; N-dimethylaminopropyl (methyl) acrylate; N, N-dimethylaminopropyl (methyl) acrylate; (methyl) acryloyl morpholine and two phenoxyethyl alcohol fluorenes acrylate.These compounds can use separately, perhaps as required, also can be used in combination more than 2 kinds.
Free-radical polymerised compound also can comprise the compound of the free-radical polymerised functional group beyond (methyl) acryls such as having allyl group, dimaleoyl imino and vinyl.As its object lesson, 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, NIPA and N, N-diethyl acrylamide acrylamide.
The amount of the free-radical polymerised compound in the caking agent with respect to 100 weight part thermoplastic resins, is preferably 30～250 weight parts.When the amount of free-radical polymerised compound during less than 30 weight part, have the tendency that the thermotolerance after the curing reduces easily, and if it surpasses 250 weight parts, then when caking agent being formed film and use, have the tendency that film-forming properties reduces.Consider the amount of free-radical polymerised compound, more preferably 50～150 weight parts from same viewpoint.
In addition, as described later, when the acidic cpd of (e) composition had the free-radical polymerised functional groups such as vinyl, the free-radical polymerised compound different with (e) composition can be used as (b) composition.
(c) urea compounds of composition is the represented compound of above-mentioned general formula (10).By this urea compounds and acidic cpd are used in combination, the contact resistance that can suppress under hot and humid rises and bonding strength decline, and then stability is improved specifically.On the other hand, according to the inventor's etc. discovery, with acidic cpd and melamine resin combination the time, although the bonding strength at initial stage is relatively good, in the situation such as after the prolonged preservation, bonding strength significantly reduces.Its reason is not yet clear and definite, but can consider that this is because when prolonged preservation, in the presence of acidic cpd, self slowly reacts melamine resin easily.
In the formula (10), R 1And R 2Independent expression can have substituent alkyl or hydrogen atom, R separately 1And R 2Also can interosculate and form ring.R 3And R 4Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.As R 1And R 2Alkyl, also can be by for example Carbamido substituted.
More particularly, urea compounds is preferably more than one that are selected from following general formula (11), (12), (13), (14), (15), (16) or (17) represented compound.By using these compounds, played significantly especially and improved the patience of hot and humid environment and the effect that improves stability in storage.
[changing 3]
Figure G200780043737XD00071
In formula (11)～(17), R 3And R 4With the R in the formula (10) 3And R 4Synonym.In the formula (13), R 5And R 6Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.In the formula (14), R 7And R 8Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.In the formula (16), R 9Expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl.In the formula (17), R 10And R 11Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.
More particularly, as urea compounds, the represented R of formula (11) is arranged 3And R 4Be the N of hydrogen atom, N '-dihydroxymethyl urea, the represented R of formula (12) 3And R 4Be 1 of methyl, 3-dimethoxy-methyl ethylidene urea and the represented R of formula (17) 3, R 4, R 10And R 11Be 1,3,4 of methyl, 6-four (methoxymethyl) glycoluril.
The amount of urea compounds in the caking agent with respect to 100 weight part thermoplastic resins, is preferably 1～50 weight part.If the amount of urea compounds is less than 1 weight part, then with respect to reliability test, have the tendency that effect that patience improves reduces, and if surpass 50 weight parts, then when caking agent being formed film use, have the tendency that film-forming properties reduces.Consider the amount of urea compounds, more preferably 5～30 weight parts from same viewpoint.
As the radical polymerization initiator of (d) composition, can use the in the past known compound such as known superoxide or azo-compound.From stability, reactive, intermiscibility viewpoint consideration, half life temperature was 90～175 ℃ in preferred 1 minute, and molecular weight is 180～1000 superoxide.
Object lesson as the radical polymerization initiator that is fit to; 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; two bay acyl peroxides; 1-cyclohexyl-1-methylethyl new decanoate ester peroxide; uncle's hexyl new decanoate ester peroxide; tert-butyl hydroperoxide neodecanoic acid ester; tert-butyl hydroperoxide trimethylacetic acid ester; 1; 1; 3; 3-tetramethyl butyl peroxidation-2-ethylhexanoate; 2; 5-dimethyl-2; 5-two (peroxidation of 2-ethyl hexyl acyl group) 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; two (3-methyl benzoyl) superoxide; the dibenzoyl superoxide; two (4-methyl benzoyl) superoxide; 2; 2 '-azo two-2; the 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; 1 '-azo two (1-cyclohexane nitrile); uncle's hexyl peroxidation sec.-propyl monocarbonate; the tert-butyl hydroperoxide toxilic acid; 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-methyl benzoyl) 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 pelargonate of t-amyl peroxy and t-amyl peroxy benzoic ether.These compounds may be used alone, two or more kinds can also be used in combination.
As radical polymerization initiator, also preferably (be typically 150～750nm) the optical free radical polymerization starters that produce free radical by rayed.As the optical free radical polymerization starter, for example, Photoinitiation, Photopolymerization, and Photocuring, J.-P.Fouassier, HanserPublishers (nineteen ninety-five), alpha-acetamido-amphyl or the phosphinoxide put down in writing in the 17th～35 page, because they are high to light-struck susceptibility, thereby more preferably.These optical free radical polymerization starters can use separately, also can be used in combination with superoxide or azo-compound.
The amount of radical polymerization initiator in the caking agent with respect to 100 weight part thermoplastic resins, is preferably 0.1～30 weight part.If less than 0.1 weight part, then having to produce, the amount of radical polymerization initiator solidifies the tendency that not enough possibility uprises, and if above 30 weight parts, then have stability in storage and improve the tendency that effect diminishes.Consider the amount of radical polymerization initiator, more preferably 2～20 weight parts from same viewpoint.
(e) acidic cpd of composition is the compound with 1 or 2 acidic-group such as above phosphate.And particularly preferably has an acidic cpd of phosphate and vinyl.Have the acidic cpd of phosphate and vinyl by use, can keep higher bonding force.As the acidic cpd with phosphate and vinyl ((methyl) acrylic), for example, can enumerate following general formula (21), (22) or (23) represented compound.
[changing 4]
Figure G200780043737XD00091
In the formula (21), R 30And R 31Independently represent separately hydrogen atom or methyl, w and x independently represent 1～8 integer separately.In the formula (22), R 30Expression hydrogen atom or methyl, x, y and z independently represent 1～8 integer separately.In the formula (23), R 30And R 31Independently represent separately hydrogen atom or methyl, a and b independently represent 1～8 integer separately.
More particularly, acidic cpd is preferably and is selected from acid phosphorus oxygen base ethyl-methyl acrylate, acid phosphorus oxygen base ethyl propylene acid esters, acid phosphorus oxygen base propyl methyl acid esters, acid phosphorus oxygen base polyoxyethylene glycol monomethacrylates, acid phosphorus oxygen base polyoxy propylene glycol monomethyl acrylate, 2-(methyl) acryloxy ethyl phosphonic acid ester, 2,2 '-two (methyl) acryloxy diethyl phosphoric acid ester, EO (ethylene oxide) modified phosphate dimethacrylate, the phosphoric acid modification epoxy acrylate, at least a in phosphoric acid vinyl acetate and the lactone modified phosphate methacrylic ester.
The amount of acidic cpd in the caking agent with respect to 100 weight part thermoplastic resins, is preferably 0.05～30 weight part.If the amount of acidic cpd less than 0.05 weight part, then has the tendency that is difficult to obtain high-adhesive-strength, and if surpass 30 weight parts, the caking agent physical property that then has after the curing reduces, and the tendency that reduces of the effect of Reliability Enhancement.Consider the amount of acidic cpd, more preferably 0.1～20 weight part from same viewpoint.
Caking agent in the present embodiment can further contain the electroconductive particle as (f) composition.The caking agent that contains electroconductive particle, as anisotropically conducting adhesive, particularly useful.As electroconductive particle, can enumerate metallics or the carbon such as Au, Ag, Ni, Cu, scolding tin.Also can use and contain the non-conductive nucleome that is formed by glass, pottery, plastics etc., and by the coating particles of the metal that coats this nucleome or the formed coating layer of carbon as electroconductive particle.When electroconductive particle is to have the nucleome that formed by plastics and during by the coating particles of the metal that coats nucleome or the formed coating layer of carbon or hot molten metal particle, owing to have the heating and pressurizing deformability, therefore when connecting and the contact area of electrode increase, Reliability Enhancement, thus preferred.In addition, further coat the particulate of these electroconductive particles surface gained with macromolecule resin etc., can suppress to be in contact with one another caused short circuit because the use level of electroconductive particle increases the particle that causes, and the insulativity between the raising telegraph circuit, therefore can suitably use separately, also can mix with electroconductive particle and use.
The median size of electroconductive particle is considered from viewpoint dispersed, electroconductibility, is preferably 1～18 μ m.The amount of electroconductive particle in the caking agent with respect to the caking agent cumulative volume that contains electroconductive particle, is preferably 0.1～30 volume %.If the amount of electroconductive particle then has the tendency that is difficult to obtain enough electroconductibility less than 0.1 volume %, if it surpasses 30 volume %, then have the tendency that causes easily short circuit.Consider the amount of electroconductive particle, more preferably 0.1～10 weight part from same viewpoint.In addition, the volume % of electroconductive particle determines based on the volume of each composition before solidifying 23 ℃ the time.The volume of each composition can utilize proportion to be scaled to volume by weight.Perhaps, also can will can not dissolve or each composition of swelling, and just fully the appropriate solvent (water, alcohol etc.) of wetting each composition put into graduated cylinder, then to wherein dropping into each composition, and the volume of increase is obtained as this volume.
Caking agent in the present embodiment also can contain stablizer.By using stablizer, can suitably control curing speed, simultaneously, the effect that improves stability in storage is also more remarkable.Stablizer be preferably selected from the amphyls such as the quinone derivatives such as benzoquinones and quinhydrones, 4-methoxyphenol and 4-tert-butyl catechol, 2,2,6,6-tetramethyl piperidine-1-oxygen base and 4-hydroxyl-2,2, the hindered amine derivatives such as the aminooxy derivatives such as 6,6-tetramethyl piperidine-1-oxygen base and tetramethyl-piperidyl methacrylic ester.
The amount of stablizer in the caking agent with respect to 100 weight part thermoplastic resins, is preferably 0.01～30 weight part.If the tendency that the amount of stablizer less than 0.01 weight part, then has its effect to reduce, if it surpasses 30 weight parts, the tendency that then has the intermiscibility with other composition to reduce.Consider the amount of stablizer, more preferably 0.05～10 weight part from same viewpoint.
Caking agent in the present embodiment can also contain coupling agent and the bonding auxiliary agents such as driving fit rising agent, flow agent take alkoxyl silicone alkane derivatives and silazane derivative as representative.Specifically, caking agent can contain the represented silane compound of following general formula (30).This silane compound may be used alone, two or more kinds can also be used in combination.
[changing 5]
In the formula (30), R 32Expression hydrogen atom, carbonatoms are that 1～5 alkyl, carbonatoms are that 1～5 alkoxyl group, carbonatoms are 1～5 alkoxy carbonyl or aryl, with a plurality of R in a part 32Can be identical or different, R 33Expression (methyl) acryloxy, vinyl, isocyanate group, imidazolyl, sulfydryl, amino, methylamino, dimethylamino, benzylamino, phenyl amino, cyclohexyl amino, morpholinyl, piperazinyl, urea groups or glycidyl, c represents 1～10 integer.In addition, work as R 33During for (methyl) acryloxy, silane compound can be used as (b) composition.That is to say, (b) free-radical polymerised compound of composition, also can comprise formula (30) represented, R 33Silane compound for (methyl) acryloxy.
Caking agent in the present embodiment also can contain rubber.By using rubber, the effect that can obtain relaxing stress and improve cementability.Object lesson as rubber; can enumerate polyisoprene; polyhutadiene; the C-terminal polyhutadiene; the C-terminal polyhutadiene; 1; the 2-polyhutadiene; C-terminal 1; the 2-polyhutadiene; C-terminal 1, the 2-polyhutadiene; acrylic rubber; styrene butadiene rubbers; the C-terminal styrene butadiene rubbers; acrylonitrile-butadiene rubber; contain carboxyl in polymer ends; hydroxyl; the acrylonitrile-butadiene rubber of (methyl) acryl or morpholinyl; carboxylated nitrile rubber; C-terminal gathers (oxypropylene); alkoxysilyl terminal poly-(oxypropylene); poly-(oxygen tetramethylene) glycol; polyolefin diols and poly--6-caprolactone.
Consider from the viewpoint that improves cementability, preferably in side chain or terminal containing as the cyano group of high polar group or the rubber of carboxyl.In addition, consider from improving mobile viewpoint, more preferably aqueous rubber.Specifically, can enumerate aqueous acrylonitrile-butadiene rubber, contain aqueous acrylonitrile-butadiene rubber and the aqueous carboxylated nitrile rubber of carboxyl, hydroxyl, (methyl) acryl or morpholinyl in polymer ends.These rubber preferably contain 10～60 quality % vinyl cyanide.These rubber may be used alone, two or more kinds can also be used in combination.
Caking agent in the present embodiment can be aqueous (being preferably pasty state) under room temperature (0～30 ℃), also can be solid.Solid adhesive can use by heating, and also can use solvent with its gelatinization.As available solvent, as long as no with the reactivity of each composition of caking agent, and demonstrate sufficient solvability, just be not particularly limited, and the boiling point under the preferred normal pressure is 50～150 ℃ material.When boiling point during less than 50 ℃, then may volatilize when placing in that room temperature (0～30 ℃) is lower, the use in open system is restricted.In addition, if boiling point surpasses 150 ℃, then be difficult to make solvent evaporates, may produce detrimentally affect to the reliability after bonding.
The caking agent of present embodiment can also be film like.When using with film shape, consider from viewpoints such as operability, convenient.The caking agent of film like, for example, solution coat that can be by caking agent being dissolved in gained in the solvent is on the separability base materials such as fluorine resin film, pet film, release paper, perhaps make gained solution soak into the base materials such as non-woven fabrics and be placed on the separability base material, then the method for desolventizing and obtaining.
Caking agent in the present embodiment can be used as for the different multiple caking agent that is made up by sticky object of bonding thermal expansivity.Specifically, be suitable as take anisotropically conducting adhesive, silver stick with paste and silverskin etc. as the circuit connection material of representative.Perhaps, can be with the caking agent in the present embodiment as the semiconductor element adhesives take CSP elastomerics, CSP underfill, LOC band and chip attachment film (Die Attach Film) etc. as representative.
Fig. 1 is the summary sectional view of an embodiment of expression syndeton body.Syndeton body 1 shown in Figure 1 possesses: has the first circuit block 20 at formed the first splicing ear 22 on the first circuit substrate 21 and the interarea 21a thereof, has the second circuit parts 30 of formed the second splicing ear 32 on second circuit substrate 31 and interarea 31a thereof, and between the first circuit block 20 and second circuit parts 30 and the adhesive linkage 10 that they are bonding.20 relative configurations make the second splicing ear 32 relative with the first splicing ear 22 thereby second circuit parts 30 are with the first circuit block.
Adhesive linkage 10 is formed by the above-mentioned caking agent that contains electroconductive particle, and is made of insulation layer 11 and the electroconductive particles 7 that are dispersed in the insulation layer 11.Insulation layer 11 is to come from the composition except electroconductive particle in the caking agent, and the cured article that forms of the radical polymerization by free-radical polymerised compound.Relative the first splicing ear 22 and the second splicing ear 32 are electrically connected by electroconductive particle 7.On the other hand, on same circuit substrate formed the first splicing ear 22 each other, and the second splicing ear 32 insulate each other.
As the first circuit substrate 31 and second circuit substrate 21, for example, can use inorganic material substrate, plastic base or the glass/epoxy substrates such as semi-conductor, glass and pottery.As plastic base, can enumerate Kapton, polycarbonate film and polyester film.The first splicing ear and the second splicing ear are formed by metals such as copper.
More particularly, one of the first circuit block 20 and second circuit parts 30 can be to have glass substrate or plastic base as circuit substrate, and have the display panels by formed splicing ears such as ITO.In addition, one of the first circuit block 20 and second circuit parts 30, also can be to have Kapton as flexibility printed circuit board (FPC), band year encapsulation (TCP) or the thin membrane flip chip encapsulation (COF) of circuit substrate, or have semiconductor substrate as the semi-conductor silicon chip of circuit substrate.These various circuit blocks, appropriate combination consists of the syndeton body as required.
Syndeton body 1, for example, by so that the first splicing ear 22 mode relative with the second splicing ear 32 is overlapping with caking agent and the second circuit parts 30 of the first circuit block 20, film like successively, and under this state heating and pressurizing, make the method that caking agent solidifies and form.Heating temperature is not particularly limited, and is preferably 100～250 ℃.Pressure so long as can just not be not particularly limited being produced the scope of damage by sticky object, is generally 0.1～10MPa.This heating and pressurization are preferably carried out in 0.5 second～120 seconds scope, can be undertaken bonding by 140～200 ℃, 3MPa, 10 seconds heating.
Embodiment
Below, enumerate embodiment the present invention is made more specific description.But the present invention is not limited to following examples.
Material
(a) thermoplastic resin
Phenoxy resin: PKHM-30 (trade(brand)name), InChem society makes
Butyral resin: electrochemical butyral 3000-1 (デ Application カ Block チ ラ one Le 3000-1, trade(brand)name), electrochemical industry society makes
Polyester urethane resin: UR-3500 (trade(brand)name), Japan spin society and make
Urethane resin: be that 2000 polybutylene adipate diol, 450 weight part molecular-weight average are 2000 polyoxy tetramethylene glycol and 100 weight parts 1 with 450 weight part molecular-weight average, the 4-butyleneglycol evenly mixes in 4000 weight part methyl ethyl ketones, and add 390 weight part diphenylmethanediisocyanates, under 50 ℃, make its reaction and obtain (weight-average molecular weight is 100,000).
(b) free-radical polymerised compound
Tricarbimide EO modification triacrylate: M-315 (trade(brand)name), Toagosei Co., Ltd makes
Ammonia ester acrylate: AT-600 (trade(brand)name), Kyoeisha Chemical Co., Ltd. makes
(c) urea compounds
N, N '-dihydroxymethyl urea (urea compounds 1): Tokyo changes into manufacturing
1,3,4,6-four (methoxymethyl) glycoluril (urea compounds 2): Tokyo changes into manufacturing
1,3-dimethoxy-methyl ethylidene urea (urea compounds 3): make 37% formaldehyde (Northeast chemistry is made) under 43 weight part 2-imidazolones (manufacturing of Aldrich company) and the 122 weight part alkaline conditions descend reaction after 1 hour at 100 ℃, be cooled to room temperature (25 ℃), add 32 weight part methyl alcohol (Northeast chemistry is made), under acidic conditions, stirred 30 minutes, and heated up in a steamer and anhydrate and obtain (yield is 72%).
(d) radical polymerization initiator
Uncle's hexyl peroxidation-2-ethylhexanoate: PERHEXYL O (trade(brand)name), NOF Corp makes
(e) acidic cpd
2-(methyl) acryloxy ethyl phosphonic acid ester: light ester (ラ イ ト エ ス テ Le) P-2M (trade(brand)name), Co., Ltd. of common prosperity society makes
Lactone modified phosphate methacrylic ester: カ ヤ マ one PM-21 (trade(brand)name), Nippon Kayaku K. K makes
The making of film like caking agent
Phenoxy resin and each 40g of butyral resin are dissolved in respectively in the 60g methyl ethyl ketone, prepare thus the solution that solids component is 40 % by weight.With polyester urethane resin, be dissolved in the mixed solvent of methyl ethyl ketone and toluene.With these solution for the preparation of caking agent.
In addition, be produced on by being provided with the nickel dam that thickness is 0.2 μ m on the formed nucleome of the polystyrene surface, and in the arranged outside of this nickel dam thickness to be arranged be the electroconductive particle (median size is 4 μ m, and proportion is 2.5) of the gold layer of 0.02 μ m.
With the composition shown in the table 1 (solid weight ratio) mixed thermoplastic resin, free-radical polymerised compound, urea compounds, radical polymerization initiator and acidic cpd, and then add above-mentioned electroconductive particle with the ratio of 1.5 volume %, and it is disperseed, prepare the adhesive solution in each embodiment and the comparative example.
Use apparatus for coating that the adhesive solution of gained is coated on the fluorine resin film that thickness is 80 μ m, and pass through 70 ℃, 10 minutes warm air drying, obtain the film-like adhesive that thickness is 18 μ m.
[table 1]
Figure G200780043737XD00151
The evaluation of film like caking agent
(1) bonding strength, contact resistance
Use the film like caking agent of gained, for the flexible electric circuit board (FPC) of the copper circuit with 500 live widths, 25 μ m, spacing 50 μ m, thickness 12 μ m be formed with the glass substrate of thin layer of Indium sesquioxide (ITO) of 0.2 μ m (thickness is 1.1 μ m, surface resistivity is 20 Ω/), with hot pressing device (type of heating: permanent pattern of fever, Dongli Engineering Co., Ltd makes) under 160 ℃ of temperature, 3MPa, carry out the heating and pressurizing in 10 seconds, being connected to width is 2mm, makes the syndeton body.After bonding at once and after in 85 ℃, the hot and humid groove of 85%RH, keeping 168 hours, with the resistance value between the adjacent circuit of multitester measuring gained syndeton body.Resistance value represents with the mean value of 37 of the resistance between adjacent circuit.
In addition, according to JIS-Z0237, measure the bonding strength of syndeton body with 90 degree stripping methods.The determinator of bonding strength uses the (East of Japan Powerleader temperature Co., Ltd. ocean ボ one Le De ウ イ Application Co., Ltd.) this grand (テ Application シ ロ Application) UTM-4 (peeling rate is 50mm/min, 25 ℃) of sky of making.
The mensuration of contact resistance and bonding strength, be after bonding at once and with the syndeton body for carrying out after 168 hours the reliability test in 85 ℃, the hot and humid groove of 85%RH, keeping.Measurement result is shown in table 2.
[table 2]
Hence one can see that, and the film like caking agent of embodiment 1～7 at once and after hot and humid processing, all demonstrates good contact resistance and bonding strength, and all has enough patience for reliability test after bonding.On the other hand, in the comparative example 1～3 that does not use urea compounds, can confirm hot and humid processing after, bonding strength significantly reduces.In addition, do not use the comparative example 4 of acidic cpd, at once contact resistance and bonding strength is not enough after bonding, produces after hot and humid processing and peels off.In the table 2, open to the outside world represents that contact resistance is more than 500 Ω, and when " peeling off " referred to measure stripping strength (bonding strength), FPC peeled off.
(2) stability in storage
Film like caking agent to gained among the embodiment 3,6 is implemented vacuum packaging, and 40 ℃ of lower placements 3 days.Then, and the situation of " (1) bonding strength, contact resistance " similarly, makes the syndeton body, measures bonding strength and contact resistance.Measurement result and place before the value of (after bonding at once) be shown in together table 3.
[table 3]
Figure G200780043737XD00171
Hence one can see that, and embodiment 3,6 film like caking agent all demonstrate good contact resistance and bonding strength before and after 40 ℃/3 days placement, and stability in storage is excellent.
Can confirm according to above-mentioned experimental result, according to the present invention, can provide a kind of high-adhesive-strength that shows, simultaneously have high patience for the reliability test hot and humid under, and then the also radical-curable caking agent of excellence of stability in storage.

Claims (5)

1. caking agent, it contains (a) thermoplastic resin, (b) free-radical polymerised compound, (c) by the represented urea compounds of following general formula (10), (d) radical polymerization initiator and the acidic cpd that (e) has phosphate and vinyl
[changing 1]
Figure FSB00000969465400011
In the formula (10), R 1And R 2Independent expression has or does not have substituent alkyl or hydrogen atom, R separately 1And R 2Interosculating, it is also harmless to form ring, R 3And R 4Independent expression hydrogen atom, carbonatoms are that 1～8 straight chained alkyl or carbonatoms are 3～10 branched-chain alkyl separately.
2. caking agent as claimed in claim 1, wherein, described thermoplastic resin comprises select at least a from the group that phenoxy resin, vibrin, urethane resin, butyral resin, acrylic resin and polyimide resin form.
3. caking agent as claimed in claim 1, wherein, described thermoplastic resin comprises polyester urethane resin.
4. such as each described caking agent in the claim 1～3, it further contains (f) electroconductive particle.
5. syndeton body, it possesses:
Have the first splicing ear the first circuit block,
Have the second splicing ear, according to the second circuit parts that make this second splicing ear mode relative with described the first splicing ear and the relative configuration of described the first circuit block and
Between described the first circuit block and described second circuit parts and the adhesive linkage that they are bonding,
Described adhesive linkage is formed by each described caking agent of claim 1～4.
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