CN113801606A - Anisotropic conductive adhesive composition, conductive adhesive film, connector and semiconductor device - Google Patents
Anisotropic conductive adhesive composition, conductive adhesive film, connector and semiconductor device Download PDFInfo
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- CN113801606A CN113801606A CN202111174001.4A CN202111174001A CN113801606A CN 113801606 A CN113801606 A CN 113801606A CN 202111174001 A CN202111174001 A CN 202111174001A CN 113801606 A CN113801606 A CN 113801606A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- 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
- 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
- C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09J171/12—Polyphenylene oxides
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/10—Adhesives in the form of films or foils without carriers
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
- H01L2224/29001—Core members of the layer connector
- H01L2224/29099—Material
- H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
Abstract
The present invention relates to an anisotropic conductive adhesive composition, a conductive adhesive film containing the same, a connector, and a semiconductor device. The anisotropic conductive adhesive composition of the present invention comprises an adhesive composition and conductive particles; wherein the adhesive composition comprises: a thermoplastic resin; a radical polymerizable compound; and a free radical initiator; wherein the radical polymerizable compound comprises at least one acrylic polymer having both a fluorene skeleton and a urethane group. The conductive film of the present invention comprises the composition of the present invention. The connecting body and the semiconductor device of the invention adopt the conductive adhesive film of the invention as an adhesive. The composition of the present invention, when used as an adhesive for connecting a connecting body and a circuit of a semiconductor device, has sufficient adhesiveness and low resistance not only when cured at low temperature for a short time; and can maintain sufficient and stable adhesiveness and low and stable resistance under special conditions (e.g., 85 ℃, 85% RH, 500h exposure).
Description
Technical Field
The present invention relates to the field of circuit connection adhesives, and more particularly, to an anisotropic conductive adhesive composition, a conductive adhesive film, a connector, and a semiconductor device.
Background
In recent years, in the field of precision electronic devices, with the increase in integration of semiconductor elements and the increase in definition of liquid crystal elements, pitches between elements and between wirings have been decreasing.
In order to reduce adverse effects on peripheral members caused by heating during curing, it is necessary to lower the pressure bonding temperature when thermocompression bonding is performed using an anisotropic conductive film, and it is also necessary to shorten the pressure bonding time in order to improve the production efficiency.
In order to solve this problem, in the prior art, a polymerizable acrylic compound curable at low temperature for a short time is generally used as a main component of the anisotropic conductive adhesive film.
The polymerizable acrylic compound can be cured at a low temperature for a short time, and has sufficient adhesiveness and low electric resistance after curing; however, under special conditions, such as 85 ℃ and 85% RH (where RH stands for relative humidity), the adhesion is reduced and the connection resistance is increased after a long time (such as 500 hours) exposure, and thus the requirements of the connectors and semiconductor devices for the reliability of circuit connection cannot be satisfied.
Accordingly, it is highly desirable to provide an anisotropic conductive adhesive composition and a conductive adhesive film that satisfy the above conditions at the same time.
Disclosure of Invention
The invention provides an anisotropic conductive adhesive composition which can have enough adhesiveness and lower resistance after being cured at low temperature for a short time, can maintain enough and stable adhesive force and lower and stable resistance under special conditions (such as 85 ℃, 85% RH and 500 hours of exposure), and meets the requirements of connecting pieces and semiconductor devices on circuit connection reliability.
According to an aspect of the present invention, there is provided an anisotropic conductive adhesive composition including an adhesive composition and conductive particles; wherein the bonding composition comprises:
a thermoplastic resin;
a radical polymerizable compound;
a free radical initiator; wherein the content of the first and second substances,
the radical polymerizable compound includes at least one acrylic polymer having both a fluorene skeleton and a urethane group.
According to one embodiment of the composition of the present invention, the acrylic polymer having both a fluorene skeleton and a urethane group has a weight average molecular weight of 5000 to 60000.
According to one embodiment of the composition of the present invention, in the acrylic polymer having both a fluorene skeleton and a urethane group, the polymerizable monomer constituting the polymerizable unit having the fluorene skeleton is selected from at least one of:
9, 9-bis (4-hydroxyphenyl) fluorene, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxypropoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxydiethoxy) phenyl ] fluorene, 9, 9-bis [4- (2-hydroxydipropyloxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytriethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxytripropoxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytetraethoxy) phenyl ] fluorene and 9, 9-bis [4- (2-hydroxytetrapropoxy) phenoxyethanol ] fluorene;
preferably, the polymerized monomer having a fluorene skeleton polymerized unit is constituted by 5 to 30% by mole of the total polymerized monomers.
According to one embodiment of the composition of the present invention, in the polymer having both a fluorene skeleton and a urethane group, the urethane group-forming polymeric monomer includes a diisocyanate; wherein the content of the first and second substances,
the diisocyanate comprises at least one of the following: 2, 4-tolylene diisocyanate, 4' -diphenylmethane diisocyanate, 1, 6-hexamethylene diisocyanate, and isophorone diisocyanate;
preferably, the diisocyanate accounts for 8-25% of all the polymerized monomers in mole percentage.
According to one embodiment of the composition of the present invention, the polymerized monomers of the acrylic polymer having both a fluorene skeleton and a urethane group include: succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate and hydroxypropyl acrylate.
According to one embodiment of the composition of the present invention, the polymerized monomers of the acrylic polymer having both a fluorene skeleton and a urethane group include: adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate, and hydroxypropyl acrylate.
According to one embodiment of the composition of the present invention, the adhesive composition comprises 30 to 60 parts by weight of a thermoplastic resin; 20-150 parts of a free radical polymerizable compound; 0.05-20 parts of a free radical initiator; wherein the content of the first and second substances,
the radical polymerizable compound includes: 20-100 parts of acrylic polymer containing fluorene skeleton and carbamate group;
the conductive particles account for 0.1-30% of the bonding composition by volume percentage.
According to another aspect of the present invention, there is provided an anisotropic conductive adhesive film comprising the composition of the present invention.
According to another aspect of the present invention, there is provided a connector using the anisotropic conductive film of the present invention as a circuit connection adhesive.
According to another aspect of the present invention, there is provided a semiconductor device comprising the anisotropic-electroconductive adhesive film of the present invention as a circuit connection adhesive.
Compared with the prior art, the technical scheme of the invention has the following beneficial effects:
in the composition of the present invention, at least one acrylic polymer having both a fluorene skeleton and a urethane group is contained, and when the composition is used for a circuit connection adhesive, the composition can have sufficient adhesiveness and low resistance after being cured at low temperature in a short time; the adhesive can maintain enough and stable adhesiveness and lower and stable resistance under special conditions (such as 85 ℃, 85% RH and 500h exposure), and meets the requirements of the connecting piece and the semiconductor device on the circuit connection reliability.
The anisotropic conductive adhesive film of the present invention, when used for a connector, also has the above-mentioned excellent effects, because of using the composition of the present invention.
The connector of the present invention has the above-mentioned excellent effects because the anisotropic conductive film of the present invention is used.
The semiconductor device of the present invention also has the above-mentioned excellent effects because the anisotropic conductive film of the present invention is used.
Drawings
FIG. 1 shows a cross-sectional view of an anisotropic-electroconductive adhesive film according to the present invention;
FIG. 2 shows a cross-sectional view of one embodiment of a connector of the present invention;
reference numerals: anisotropic conductive adhesive composition 1, conductive particles 2, adhesive composition 3;
a connecting body 101; an anisotropic conductive adhesive film 1 a; a first circuit part 10; a first substrate 11; a first circuit electrode 12; a second circuit part 20; a second substrate 21; and a second circuit electrode 22.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the drawings and embodiments of the specification, and it is obvious that the described embodiments are only a part of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
According to an aspect of the present invention, there is provided an anisotropic conductive adhesive composition including an adhesive composition and conductive particles; wherein the bonding composition comprises:
a thermoplastic resin;
a radical polymerizable compound;
a free radical initiator; wherein the content of the first and second substances,
the radical polymerizable compound includes at least one acrylic polymer having both a fluorene skeleton and a urethane group.
The composition of the invention comprises at least one polymer simultaneously having a fluorene skeleton and a urethane group, and when the composition is used for a circuit connection adhesive, the composition can be cured within a short time (such as a few seconds) at a low temperature (such as 120-170 ℃), so that the composition has sufficient adhesiveness and low resistance; sufficient and stable adhesiveness and low and stable resistance can be maintained under special conditions (e.g., 85 ℃, 85% RH, 500h exposure).
This is because the composition of the present invention can improve the elastic modulus and the glass transition temperature of a cured product formed after radical polymerization curing of the composition, because the composition contains an acrylic polymer having both a fluorene skeleton and a urethane group in the radical polymerizable compound and has a benzene ring contained in the fluorene skeleton as a rigid structure.
The improvement in the elastic modulus and the glass transition temperature can improve the heat resistance and hydrolysis resistance of the cured product.
Due to the improvement of the heat resistance and hydrolysis resistance of the cured product, the formed cured product has high temperature (such as 85 ℃) and high humidity (such as 85% RH), and after long-term exposure (such as 500h), the adhesive is not damaged by heat and moisture, so the adhesive force is not reduced.
Meanwhile, due to the improvement of the heat resistance and the hydrolysis resistance of the cured product, the cured product can not be degraded due to heating and moisture, so that the conductive particles can keep the original deformation, and the resistance is lower and stable.
On the other hand, since the fluorene skeleton has a low linear expansion coefficient, the expansion of a cured product is small after a long-term exposure (e.g., 500 hours) in an environment of a high temperature (e.g., 85 ℃) and a high humidity (85% RH), and the conductive particles can maintain their original deformation, thereby reducing and stabilizing the resistance.
On the other hand, since the fluorene skeleton is contained, the elastic modulus of the cured product is increased, and therefore, the cohesiveness of the cured product is increased, thereby increasing the adhesive strength of the cured product.
In conclusion, the introduction of the fluorene skeleton makes it possible to maintain a sufficient and stable adhesive force and a low and stable electric resistance of the cured product under special conditions.
Meanwhile, the carbamate compound has good adhesion to circuit board materials, so the polymer synthesized by the invention simultaneously has carbamate groups.
The adhesive composition has enough and stable adhesive force and low and stable resistance after being cured and subjected to 85 ℃ and 85% RH aging test.
Wherein the fluorene skeleton is
The carbamate group is
The acrylic polymer having both a fluorene skeleton and a urethane group contained in the composition of the present invention is named as an acrylic polymer because the polymer includes a terminal block, and a polymerization unit of the terminal block contains an acrylic group, and a polymerization monomer thereof is preferably a hydroxyl group-containing methacrylic acid and/or a hydroxyl group-containing acrylic compound.
Further preferred are hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, 2-methacrylic acid, mono [2- [ (2-methyl-acryloyl) oxy ] ethyl ] succinate, di (2-methyl-2-acrylic acid) 2-hydroxy-1, 3-propanediol, 2-acrylic acid-2-hydroxy-1, 3-propanediol, 2-hydroxy-2-acrylate, butyl 2-hydroxy-2-acrylate, 2-hydroxy-3-phenoxypropyl 2-acrylate, mono-2- (2-acryloyloxy) hydroxyethyl succinate, 1, 2-phthalic acid-mono [2- [ (1-oxo-2-propenyl) Oxy ] ethyl ester, 2-hydroxyethyl-2- [ (2-acryloyl) oxy ] ethyl 1, 2-benzenedicarboxylate.
Because the acrylic group of the end-capping group contains a double bond, a radical polymerization reaction can occur under the initiation of a radical initiator.
According to one embodiment of the composition of the present invention, the weight average molecular weight of the polymer having both a fluorene skeleton and a urethane group is 5000 to 60000.
When the weight average molecular weight of the polymer is less than 5000, the composition, after radical polymerization, forms a cured product having a low elastic modulus and a low glass transition temperature, and after exposure to a specific condition (e.g., 85 ℃ C., 85% RH) for a long time (e.g., 500 hours), the composition has a high electric resistance and a low adhesive strength.
When the weight average molecular weight of the polymer exceeds 60000, reactivity may be reduced and crosslinking density may be reduced.
In summary, when the weight average molecular weight of the polymer is 5000 to 60000, the adhesion and the electrical resistance of the cured product are optimized.
Specifically, the weight average molecular weight is further preferably 10000 to 55000; further preferably 15000-50000; further preferably 20000 to 45000; further preferably 25000 to 40000; further preferably 30000 to 35000.
According to one embodiment of the composition of the present invention, in the acrylic polymer having both a fluorene skeleton and a urethane group, the polymerizable monomer constituting the polymerizable unit having the fluorene skeleton is selected from at least one of:
9, 9-bis (4-hydroxyphenyl) fluorene, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxypropoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxydiethoxy) phenyl ] fluorene, 9, 9-bis [4- (2-hydroxydipropyloxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytriethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxytripropoxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytetraethoxy) phenyl ] fluorene and 9, 9-bis [4- (2-hydroxytetrapropoxy) phenoxyethanol ] fluorene;
preferably, the polymerized monomer having a fluorene skeleton polymerized unit is constituted by 5 to 30% by mole of the total polymerized monomers.
According to the composition of the present invention, if the molar percentage of the polymerizable monomer having a fluorene skeleton-polymerized unit to all the polymerizable monomers is less than 5%, the content of the fluorene skeleton in the composition is small, and the composition cannot maintain sufficient and stable adhesiveness and low and stable resistance under special conditions when used as an adhesive for a interconnector; if the content is more than 30%, the content of the fluorene skeleton in the composition becomes too high, and the composition cannot be used as an adhesive for a interconnector, and sufficient adhesiveness is maintained under special conditions.
Further, it is preferably 10% to 25%, and more preferably 15% to 20%.
According to one embodiment of the composition of the present invention, in the acrylic polymer having both a fluorene skeleton and a urethane group, the polymeric monomer forming the urethane group includes a diisocyanate, wherein the diisocyanate includes at least one of:
2, 4-tolylene diisocyanate, 4' -diphenylmethane diisocyanate, 1, 6-hexamethylene diisocyanate and isophorone diisocyanate.
Preferably, the diisocyanate accounts for 8-25% of all the polymerized monomers in mole percentage.
According to the composition of the present invention, if the molar ratio of diisocyanate to all the polymerized monomers is less than 8%, the content of urethane groups in the polymer is small, and the composition cannot maintain sufficient adhesion as a connected body; if the amount is more than 25%, a large amount of low molecular weight compounds are formed in the composition, which may affect the properties of the polymer.
More preferably 10% to 23%, still more preferably 13% to 20%, and still more preferably 15% to 18%.
In addition, the urethane group-forming polymeric monomer may also include a compound having two or more NCO groups, that is, may also include a polyisocyanate.
According to one embodiment of the composition of the present invention, the polymerized units of the acrylic polymer having both a fluorene skeleton and a urethane group include: succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate and hydroxypropyl acrylate.
According to one embodiment of the composition of the present invention, the polymerized units of the acrylic polymer having both a fluorene skeleton and a urethane group include: adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate, and hydroxypropyl acrylate.
The method for producing an acrylic polymerizable compound (PFUA) having both a fluorene skeleton and a urethane group is as follows: the polyester polyol is obtained by the polymerization reaction of polyhydric alcohol containing fluorene skeleton, polybasic acid and other polyhydric alcohol; reacting a polyol with a polyisocyanate; and then end-capping with hydroxyl-containing methacrylic acid or hydroxyl-containing acrylic acid.
The general procedure is as follows: dissolving polyester polyol obtained by reacting dicarboxylic acid, dihydric alcohol and dihydric alcohol containing a fluorene skeleton (the reaction temperature is 170-200 ℃ generally, and the reaction time is 5-7 hours) in a solvent (such as butanone) to obtain a standby solution. After introducing nitrogen gas into a reaction vessel equipped with a stirrer, a thermometer, a condenser tube and a nitrogen gas introducing device, the polyester polyol solution was added thereto, and then a predetermined amount of isocyanate and 0.15% by weight of dibutyltin laurate as a catalyst to the polyester polyol were added, and the reaction temperature was controlled to 60 to 90 ℃ and the reaction was carried out for a predetermined time. Then adding hydroxyl-containing acrylic acid and 0.1 to 0.3 percent of o-methyl hydroquinone relative to the hydroxyl-containing acrylic acid for end capping. The acrylic polymer having both a fluorene skeleton and a urethane group is obtained by treating the above solution.
Among these, in one embodiment of the composition of the present invention, an acrylic polymer having a fluorene skeleton and a urethane group together with succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate, and hydroxypropyl acrylate as polymerization monomers is preferably used, and is referred to as PFUA-1.
In one embodiment of the composition of the present invention, an acrylic polymer having a fluorene skeleton and a urethane group together with adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate, and hydroxypropyl acrylate as polymerization monomers is preferably used, and is referred to as PFUA-2.
In order to more clearly explain and explain the acrylic polymer having both a fluorene skeleton and a urethane group according to the present invention, the reaction process of PFUA-1 is exemplified.
In the preparation process of PFUA-1, one of a plurality of generation modes and a plurality of structural formulas of polyester polyol is selected for illustration, a specific equation is shown as follows, and a structural schematic diagram of the polyester polyol is shown as A.
Of course, there are many reaction modes of the polyester polyol and many structural formulas of the polyester polyol, and the reaction modes are only for schematically illustrating the technical scheme of the invention and are not limited thereto.
A schematic diagram of one reaction mode of the polyester polyol and isocyanate reaction, and the capping reaction, is shown below.
It should also be noted here that other reaction modes and products exist in the two-step reaction, and the reaction modes and products are only exemplary to illustrate the reaction modes and products, so as to more clearly illustrate the structure of the acrylic polymer containing both fluorenyl group and urethane group in the present invention.
According to one embodiment of the composition of the present invention, the radical polymerizable compound further includes a vinyl compound containing a phosphoric group.
The composition of the present invention further contains a vinyl compound containing a phosphoric group, and the adhesive strength to the surface of an inorganic material such as a metal when the composition is used as an adhesive can be enhanced.
According to one embodiment of the composition of the present invention, the adhesive composition comprises 30 to 60 parts by weight of a thermoplastic resin; 20-150 parts of a free radical polymerizable compound; 0.05-20 parts of a free radical initiator; wherein the content of the first and second substances,
20 to 100 parts of an acrylic polymer having both a fluorene skeleton and a urethane group;
the conductive particles account for 0.1-30% of the bonding composition by volume percentage.
Thermoplastic resin
In the composition of the present invention, a known thermoplastic resin can be selected without any particular limitation. Specifically, polyimide, polyamide, phenoxy resins, poly (meth) acrylates, polyimides, polyurethanes (urethane resins), polyesters, polyvinyl butyrals, and the like are preferable. These may be used singly or in combination of two or more. Furthermore, these resins may also contain siloxane bonds and fluorine substituents. These resins may be used as long as they are completely compatible with each other or microphase-separated to cause cloudiness.
Among these, the thermoplastic resin is preferably 30 to 60 parts, more preferably 35 to 55 parts, and still more preferably 40 to 50 parts.
Radical polymerizable compound
In the radically polymerizable compound of the present invention, it is preferably 20 to 150 parts, more preferably 30 to 140 parts, further preferably 40 to 120 parts, further preferably 50 to 110 parts, further preferably 60 to 100 parts, further preferably 70 to 90 parts, and further preferably 80 to 90 parts.
A radically polymerizable compound which is required to include at least one acrylic polymer having both a fluorene skeleton and a urethane group; the polymer is preferably 20 to 100 parts; more preferably 30 to 90 parts, still more preferably 40 to 80 parts, still more preferably 50 to 70 parts, and still more preferably 60 to 65 parts.
The radical polymerizable compound may be a vinyl compound containing a phosphoric group, in addition to the above-mentioned polymer.
The phosphoric acid group-containing vinyl compound is preferably a vinyl compound having at least 1 phosphoric acid group in the molecule.
Further preferred are: acid phosphoxyethyl methacrylate, acid phosphoxyethyl acrylate, acid phosphoxypropyl methacrylate, acid phosphoxypolyoxyethylene glycol monomethacrylate, acid phosphoxypolyoxypropylene glycol monomethacrylate, 2' -di (meth) acryloyloxy diethyl phosphate, EO (ethylene oxide) -modified phosphodimethacrylate and phosphoric acid-modified epoxy acrylate.
The amount of the phosphoric acid group-containing vinyl compound is preferably 0.1 to 15 parts, more preferably 1 to 13 parts, still more preferably 2 to 12 parts, yet more preferably 3 to 10 parts, yet more preferably 4 to 9 parts, and yet more preferably 5 to 7 parts.
In addition, a conventional radical polymerizable compound can be selected as the radical polymerizable compound. For example: acrylate compounds, methacrylate compounds, styrene derivatives, maleimide derivatives, and the like, which are polymerizable by free radicals.
Free radical polymerization initiator
As the radical polymerization initiator, known compounds such as peroxides, azo compounds, photoinitiators and the like can be used.
Specifically, the following can be selected: isobutyl peroxide, trimethyladipic acid dibutyl peroxide, 2, 4-dichlorobenzoyl peroxide, 2, 5-dimethyl-2, 5-di (tert-butylperoxy) hexane, diisopropyl peroxydicarbonate, bis (4-tert-butylcyclohexyl) peroxydicarbonate, tert-butylperoxyisobutyrate, tert-butylperoxy pivalate, diisopropylbenzene hydroperoxide, cumene hydroperoxide, 1 ' -bis (tert-butylperoxy) -3, 3, 5-trimethylcyclohexane, 2,2 ' -azobisisobutyronitrile, 2,2 ' -azobis (2-methylbutyronitrile), 2,2 ' -azobis-2, 4-dimethylvaleronitrile, 4 ' -azobis (4-cyanovaleric acid), Ketones such as benzophenone and acetophenone, and derivatives thereof. These compounds may be used alone, or two or more compounds may be mixed and used.
Preferably, the radical initiator is 0.05 to 20 parts, more preferably 1 to 18 parts, further preferably 2 to 15 parts, further preferably 3 to 13 parts, further preferably 4 to 10 parts, and further preferably 5 to 8 parts.
Conductive particles
As the conductive particles, metal particles such as Au, Ag, Ni, Cu, and solder, carbon, and the like can be used. Particles in which a core is made of non-conductive glass, ceramic, plastic, or the like and a metal, metal particles, and carbon are coated on the core can also be used.
Wherein, the conductive particles preferably account for 0.1-30% of the bonding composition in volume percentage; more preferably from 2% to 25%, still more preferably from 5% to 20%, still more preferably from 10% to 15%.
According to an embodiment of the composition of the present invention, a filler may be further included, and the filler is selected from silica, calcium carbonate, titanium dioxide, and the like.
The filler is preferably 1 to 30 parts, more preferably 5 to 25 parts, further preferably 10 to 20 parts, and further preferably 15 to 18 parts.
According to an embodiment of the composition of the present invention, the composition may further comprise an auxiliary agent, wherein the auxiliary agent is selected from a stabilizer, a coupling agent, an adhesion promoter, and the like.
The auxiliary is preferably 0.1 to 10 parts, more preferably 2 to 9 parts, and further preferably 4 to 8 parts.
According to another aspect of the present invention, there is provided an anisotropic conductive adhesive film comprising the composition of the present invention.
The conductive adhesive film of the present invention containing the composition of the present invention, including at least one acrylic polymer having both a fluorene skeleton and a urethane group, can be cured at low temperature in a short time and has sufficient adhesiveness and low resistance when used for circuit connection of a semiconductor device; it is also possible to maintain sufficient and stable adhesion and low and stable resistance after exposure to specific conditions (e.g., 85 ℃ C., 85% RH) for a long period of time (500 hours).
The anisotropic conductive adhesive film according to the present invention is prepared by the following method.
The components are mixed and dispersed into the solvent according to the proportion of the components in the composition to obtain the dispersion liquid. The resulting dispersion was coated on a PET release film (thickness of the release film is generally 50 μm) by a coating apparatus, and dried by hot air (drying at 70 ℃ C. for 5 minutes, generally) to obtain an anisotropic conductive adhesive film (thickness is generally 25 μm).
The solvent selected for use in the conductive adhesive film dispersion of the present invention has very low reactivity with the anisotropic conductive adhesive composition and has sufficient solubility in the composition.
The solvent is preferably 50 to 300 parts, more preferably 100 to 250 parts, and still more preferably 150 to 200 parts.
The solvent is preferably at least one of the following: butanone, toluene, ethyl acetate, and cyclohexanone.
As shown in fig. 1, the conductive adhesive film according to the present invention is shown in fig. 1, and as can be seen from fig. 1, in the anisotropic conductive adhesive film made of the anisotropic conductive adhesive composition 1, conductive particles 2 are dispersed in an adhesive composition 3.
According to another aspect of the present invention, there is provided a connector using the conductive adhesive film of the present invention as an adhesive for circuit connection.
According to one embodiment of the connector of the present invention, as shown in fig. 2, the connector 101 includes a first circuit part 10 of a first substrate 11 having a first circuit electrode 12 and a second circuit part 20 having a second circuit electrode 22 and a second substrate 21.
The preparation method comprises the following steps: the first circuit electrode 12 and the second circuit electrode 22 were arranged to face each other, and the anisotropic conductive adhesive film 1a (2 is conductive particles, 3a is an adhesive composition) of the present invention was interposed between the first substrate 11 and the second substrate 21 which were arranged to face each other, and heated and pressurized to electrically connect the first circuit electrode 12 and the second circuit electrode 22.
A method of manufacturing an embodiment of a semiconductor device according to the present invention is: the anisotropic conductive film of the present invention is interposed between a semiconductor element and a semiconductor mounting substrate which are arranged to face each other, and the semiconductor element and the semiconductor mounting substrate are electrically connected to each other by heating and pressurizing the film.
The anisotropic conductive adhesive film is used as a circuit connection adhesive in the connector, so that the connector has sufficient adhesiveness and low resistance after being cured at low temperature for a short time; sufficient and stable adhesion and low and stable resistance can be maintained under special conditions (such as 85 ℃, 85% RH, exposure for 500 h).
The present invention also provides a semiconductor device using the anisotropic conductive film as a circuit adhesive, which also has the above-described effects.
The present invention will be described with reference to specific examples, which are to be construed as merely illustrative and not limitative of the remainder of the disclosure.
PREPARATION EXAMPLE 1 preparation of PFUA-1
The polymerization monomers adopted in the preparation example are: succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate and hydroxypropyl acrylate.
The mol ratio of succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate and hydroxypropyl acrylate is 1.0: 1.0: 0.2: 0.3: 0.2.
dissolving polyester polyol obtained by reacting succinic acid, hexanediol and 9, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene at 180 ℃ for 6 hours in butanone to obtain a standby solution.
After introducing nitrogen gas into a reaction vessel equipped with a stirrer, a thermometer, a condenser and a nitrogen gas introducing device, the polyester polyol solution was charged into the reaction vessel. Next, isophorone diisocyanate and 0.15% by weight of dibutyltin laurate as a catalyst to polyester polyol were charged, and the reaction temperature was controlled at 80 ℃ to react for 18 hours. Then adding hydroxypropyl acrylate and o-methyl hydroquinone which is 0.1 to 0.3 percent relative to hydroxypropyl acrylate for end capping to obtain PFUA-1-1; the weight average molecular weight of PFUA-1-1 was 25000 as determined by gel permeation chromatography.
PREPARATION EXAMPLE 2 preparation of PFUA-2-1
The polymerized monomers in this preparation were: adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate, and hydroxypropyl acrylate.
The molar ratio of adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate and hydroxypropyl acrylate is 1.0: 1.0: 0.2: 0.3: 0.2.
the other preparation steps and parameters are the same as those of preparation example 1, and PFUA-2-1 is obtained; the weight average molecular weight of PFUA-2 was determined to be 17000 by gel permeation chromatography.
In order to explain the technical scheme of the present invention, an anisotropic conductive film prepared by using the anisotropic adhesive composition of the present invention will be described in detail as an example.
Example 1
50g of phenoxy resin (PKHC, trade name of Union carbon, average molecular weight 45000) (thermoplastic resin), 1-140 g of PFUA-1, 10g of pentaerythritol triacrylate (A-TMM-3L, trade name of New Mediterran chemical Co., Ltd.), 2g of 2- (meth) acryloyloxyethyl phosphate (9051, trade name of chemical Co., Ltd., Sadoma, Guangzhou Co., Ltd.), and 3g of dilauroyl peroxide (radical initiator) were mixed in parts by mass to 100g of methyl ethyl ketone, and then conductive particles accounting for 2.0% by volume of the adhesive composition were added to the mixture, and the mixture was uniformly dispersed to obtain a coating liquid.
Wherein a nickel layer with a thickness of 0.2 μm and a gold layer with a thickness of 0.02 μm are sequentially formed on the surface of a particle with polystyrene as a core to prepare conductive particles with an average particle size of 5 μm.
The obtained coating liquid was coated on a 50 μm PET release film by a coating apparatus, and dried by hot air at 70 ℃ for 5 minutes to obtain an anisotropic conductive adhesive film having a thickness of 25 μm.
Example 2
The procedure of example 1 was repeated except that PFUA-2-1 was used in place of PFUA-1-1.
Example 3
The procedure was repeated in the same manner as in example 1 except that the amount of PFUA-1-1 was changed to 20g, and 20g of urethane acrylate (U-2PPA, trade name of Ninghamura chemical industries, Ltd.) was added.
Preparation example comparative 1
Synthesis of PUA-1
The polymerization monomer comprises succinic acid, 1, 6-hexanediol, isophorone diisocyanate and hydroxypropyl acrylate.
The mol ratio of succinic acid, 1, 6-hexanediol, isophorone diisocyanate and hydroxypropyl acrylate is 1.0: 1.2: 0.3: 0.2.
the other procedure was exactly the same as in preparation example 1 to give PUA-1, and the weight-average molecular weight of PUA-1 was measured by gel permeation chromatography to be 27000.
Comparative example 1
The conditions were the same as in example 1 except that PFUA-1-1 was replaced with PUA-1.
Comparative example 2
The procedure was repeated in the same manner as in example 2 except that PFUA-2-1 was replaced with urethane acrylate (U-2PPA, trade name of Ningmura chemical Co., Ltd.).
Comparative example 3
The procedure was as in example 3 except that PFUA-1-1 was replaced with PUA-1.
Comparative example 4
The procedure was carried out in the same manner as in example 1 except that PFUA-1-1 was replaced with 9, 9-bis [4- (2-acryloyloxyethoxy) phenyl ] fluorene (A-BPEF-2, trade name of NONSHOM CHEMICAL INDUSTRIAL CO., LTD.).
Performance testing
In order to more clearly illustrate the present invention, the connector was prepared using the above anisotropic conductive film, and performance tests were performed thereon.
(1) Preparation of the linkers
A circuit member was prepared in which 500 chromium circuits (line width 50 μm, pitch 100 μm, thickness 0.4 μm) as circuit electrodes were formed on a glass substrate.
The anisotropic conductive adhesive film obtained in example 1 was adhered to the circuit member, and the resultant was heated and pressed at 70 ℃ and 1MPa for 2 seconds to pre-bond the circuit member.
Subsequently, the PET film was peeled off, and a 3-layer flexible circuit member (FPC) in which 500 copper circuits (50 μm in line width, 100 μm in pitch, and 18 μm in thickness) were bonded to the polyimide film via an adhesive layer was placed on the anisotropic conductive adhesive film, and heated and pressed at 160 ℃ and 3MPa for 5 seconds. Thus, the circuit component having the glass substrate and the FPC were connected across a width of 1 mm.
Also, examples 2 and 3; the anisotropic conductive adhesive films of comparative examples 1 to 4; other conditions are the same as the above steps; different linkers were obtained.
(2) Connection resistance testing
Measuring a resistance value between the opposing circuit electrodes, i.e., a connection resistance, using a multimeter with respect to the connected body; the measurement was carried out in the initial stage (when the treatment was not carried out in a constant temperature and humidity chamber at 85 ℃ and 85% RH for 500 hours); and a late stage (85 ℃, 85% RH constant temperature and humidity box exposure 500 hours) determination.
(3) Adhesive strength
The adhesive strength of the prepared bonded body was measured at a peeling speed of 50mm/min at 90 ° peeling. The measurement was carried out in the initial stage (when the treatment was not carried out in an incubator at 85 ℃ and 85% RH for 500 hours) and in the latter stage (when the treatment was carried out in an incubator at 85 ℃ and 85% RH for 500 hours).
The measurement results of the connection resistance and the adhesive strength are shown in table 1.
TABLE 1
As can be seen from Table 1, the initial connection resistance of the connectors obtained using the anisotropic conductive adhesive films prepared in examples 1 to 3 was low, and the connection resistance was hardly increased by the post-detection of the treatment at 85 ℃ and 85% RH for 500 hours.
The adhesive force is enough in the initial stage, and the adhesive force obtained by the later detection of 500h treatment under the conditions of 85 ℃ and 85% RH can be maintained to be more than 8N/cm.
It can be seen that the anisotropic conductive adhesive film prepared from the anisotropic conductive adhesive composition of the present invention has good reliability when used as a circuit adhesive for a connector.
However, in contrast, in the anisotropic conductive adhesive films prepared in comparative examples 1 to 3, since the radical polymerizable compound does not use a urethane-based polymer having a fluorene skeleton, and only contains urethane groups, although the initial connection resistance is low and the adhesive strength is still sufficient, the adhesive strength is greatly reduced to 4.2N/cm and the resistance is also sharply increased to 3.5 Ω at the later stage of exposure for 500 hours under the conditions of 85 ℃ and 85% RH.
Particularly, the anisotropic conductive adhesive film has the advantages that the embodiment 1 and the comparative example 1 are independently compared, the embodiment 2 and the comparative example 2 are independently compared, and the embodiment 3 and the comparative example 3 are independently compared, so that the film is more comparable, and the anisotropic conductive adhesive film has good connection resistance and bonding performance and good reliability under special conditions.
In comparative example 4 using an acrylic monomer containing only a fluorene skeleton, the initial connection resistance was low, and the connection resistance was hardly increased even in the later stage of treatment at 85 ℃ and 85% RH for 500 hours, but the adhesive strength was low in both the initial stage and the later stage of treatment at 85 ℃ and 85% RH; since the adhesive property is insufficient and a good adhesive effect cannot be obtained, the adhesive is not suitable for circuit connection between a connector and a semiconductor device.
In addition, by comparing the data of example 1, comparative example 1 and comparative example 4, it can be seen that:
the initial adhesion of comparative example 1, which uses only the urethane group-containing polymer, is lower than that of example 1, although it can be used;
in comparative example 4, only the compound having a fluorene skeleton was used, and the initial connection resistance was slightly higher than that in example 1, although not high;
in contrast, in example 1, the initial adhesion was improved as compared with comparative example 1 and the initial resistance was reduced as compared with comparative example 4 by using a polymer containing both a fluorene skeleton and a urethane group.
Therefore, the polymer containing the fluorene skeleton and the carbamate group is adopted, and the two groups are matched for use, so that the initial adhesive force is improved, the initial connection resistance is reduced, and the synergistic effect is achieved.
In addition, as can be seen from the comparison between the individual correspondence between comparative examples 1 to 3 and examples 1 to 3, and the individual comparison between comparative example 4 and example 1, in the anisotropic conductive adhesive composition of the present application, the fluorene skeleton and the urethane group have a synergistic effect, and the two groups are balanced and complementary to each other, so that the prepared anisotropic conductive adhesive film has good reliability, thereby satisfying the reliability requirements of various connectors and semiconductor devices in special environments.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (10)
1. An anisotropic conductive adhesive composition comprising an adhesive composition and conductive particles; wherein the content of the first and second substances,
the adhesive composition includes:
a thermoplastic resin;
a radical polymerizable compound; and
a free radical initiator; wherein the content of the first and second substances,
the radical polymerizable compound includes at least one acrylic polymer having both a fluorene skeleton and a urethane group.
2. The composition according to claim 1, wherein the acrylic polymer having both a fluorene skeleton and a urethane group has a weight average molecular weight of 5000 to 60000.
3. The composition according to claim 1, wherein in the acrylic polymer having both a fluorene skeleton and a urethane group, the polymerizable monomer constituting the unit having a fluorene skeleton is selected from at least one of:
9, 9-bis (4-hydroxyphenyl) fluorene, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxypropoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxydiethoxy) phenyl ] fluorene, 9, 9-bis [4- (2-hydroxydipropyloxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytriethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxytripropoxy) phenoxyethanol ] fluorene, 9-bis [4- (2-hydroxytetraethoxy) phenyl ] fluorene and 9, 9-bis [4- (2-hydroxytetrapropoxy) phenoxyethanol ] fluorene.
Preferably, the polymerized monomer having a fluorene skeleton polymerized unit is constituted by 5 to 30 mol% of all the polymerized monomers.
4. The composition according to claim 1, wherein in the acrylic polymer having both a fluorene skeleton and a urethane group, a polymerization monomer forming the urethane group includes diisocyanate; wherein the content of the first and second substances,
the diisocyanate comprises at least one of the following: 2, 4-tolylene diisocyanate, 4' -diphenylmethane diisocyanate, 1, 6-hexamethylene diisocyanate, isophorone diisocyanate;
preferably, the diisocyanate accounts for 8-25% of all the polymerized monomers in mole percentage.
5. The composition according to any one of claims 1 to 4, wherein the polymerizable monomer of the acrylic polymer having both a fluorene skeleton and a urethane group comprises: succinic acid, hexanediol, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, isophorone diisocyanate and hydroxypropyl acrylate.
6. The composition according to any one of claims 1 to 4, wherein the polymerizable monomer of the polymer having both a fluorene skeleton and a urethane group comprises: adipic acid, butanediol, 9-bis (4-hydroxyphenyl) fluorene, isophorone diisocyanate, and hydroxypropyl acrylate.
7. The composition as claimed in any one of claims 1 to 6, wherein the adhesive composition comprises, in parts by weight, 30 to 60 parts of a thermoplastic resin; 20-150 parts of a free radical polymerizable compound; 0.05-20 parts of a free radical initiator; wherein the content of the first and second substances,
the radical polymerizable compound includes: 20-100 parts of acrylic polymer containing fluorene skeleton and carbamate group;
the conductive particles account for 0.1-30% of the bonding composition by volume percentage.
8. An anisotropic conductive adhesive film comprising the composition according to any one of claims 1 to 7.
9. A connector, characterized in that the anisotropic conductive film according to claim 8 is used as a circuit connection adhesive.
10. A semiconductor device comprising the anisotropic conductive film according to claim 8 as a circuit connection adhesive.
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| KR20080036425A (en) * | 2006-10-23 | 2008-04-28 | 제일모직주식회사 | Anisotropic conductive film composition for high reliability and adheision |
| JP2008285647A (en) * | 2006-12-25 | 2008-11-27 | Osaka Gas Co Ltd | Urethane (meth)acrylate having fluorene skeleton and its cured product |
| CN102660201A (en) * | 2010-12-06 | 2012-09-12 | 第一毛织株式会社 | Optical member comprising anisotropic conductive film |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100673773B1 (en) * | 2005-10-18 | 2007-01-24 | 제일모직주식회사 | Anisotropic conductive film composition using fluoren-based (meth)acrylate |
| KR20080036425A (en) * | 2006-10-23 | 2008-04-28 | 제일모직주식회사 | Anisotropic conductive film composition for high reliability and adheision |
| JP2008285647A (en) * | 2006-12-25 | 2008-11-27 | Osaka Gas Co Ltd | Urethane (meth)acrylate having fluorene skeleton and its cured product |
| CN102660201A (en) * | 2010-12-06 | 2012-09-12 | 第一毛织株式会社 | Optical member comprising anisotropic conductive film |
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