EP0865653A2 - Melange electroconducteur de resine de reaction - Google Patents

Melange electroconducteur de resine de reaction

Info

Publication number
EP0865653A2
EP0865653A2 EP96946140A EP96946140A EP0865653A2 EP 0865653 A2 EP0865653 A2 EP 0865653A2 EP 96946140 A EP96946140 A EP 96946140A EP 96946140 A EP96946140 A EP 96946140A EP 0865653 A2 EP0865653 A2 EP 0865653A2
Authority
EP
European Patent Office
Prior art keywords
resin mixture
reaction resin
electrically conductive
component
layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96946140A
Other languages
German (de)
English (en)
Inventor
Heiner Bayer
Wilhelm Hekele
Erich Kattner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siemens AG
Original Assignee
Siemens AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Siemens AG filed Critical Siemens AG
Publication of EP0865653A2 publication Critical patent/EP0865653A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/09—Use of materials for the conductive, e.g. metallic pattern
    • H05K1/092—Dispersed materials, e.g. conductive pastes or inks
    • H05K1/095—Dispersed materials, e.g. conductive pastes or inks for polymer thick films, i.e. having a permanent organic polymeric binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • 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

Definitions

  • Reaction resins filled with electrically conductive particles are increasingly being used in electronic technology to produce electrically conductive connections. They are used for chip assembly, with semiconductor chips being glued onto the back in an electrically conductive manner, for bonding, for producing conductor tracks on rigid and flexible substrates and increasingly also for assembling components as a replacement or alternative to soldering.
  • Reactive resin-based conductive adhesives with chemical systems based on epoxies, silicones and acrylates are available on the market.
  • thermally hardening conductive adhesives there is a conflict for the user between the possible service life and the time required for the hardening.
  • Such conductive adhesives either have a too short useful life or a too long thermal curing time, which inadmissibly increases the throughput time in production and processing processes.
  • the user of the commercially available conductive adhesives is usually given the choice of using either two-component systems or only one-component systems which can be stored in a refrigerated state.
  • the two-component systems require an increased mixing effort and have a limited service life, with the resins that can only be stored in a refrigerated state, increased logistical effort and uncertainty during transport and storage have to be accepted.
  • the cooled products usually also require a large increase in temperature for curing. However, this is usually not desired and, in the case of materials with different coefficients of expansion, causes different thermal expansions which arise during heating and lead to stresses after cooling. These tensions can affect the durability of the adhesive bonds or the service life. he shorten the components manufactured or fastened by the gluing or in particular also impair the function of sensitive components.
  • electrically conductive reactive resins arise from the conductive particles themselves, which make the resins non-transparent due to their metallic nature and thus greatly reduce the penetration depth of the light required for curing.
  • electrically conductive reaction resin systems which, in addition to their UV curability, can also be thermally cured at usable temperatures are not known.
  • the problem of the present invention is therefore to provide a UV-curable reactive resin system which is simple and safe to process and which is sufficiently short Time leads to completely hardened and electrically conductive resin layers, which can be used as an adhesive and which can be produced in a purity sufficient for microelectronic applications.
  • the reaction resin mixture according to the invention is a one-component system which can be stored for several months at room temperature. Neither use properties such as viscosity or curing profile nor the final properties of the cured resin, such as for example, change during the storage period
  • the reaction resin mixtures can only be cured by UV and additionally have a thermal curing process which leads to fully cured, electrically conductive resins at moderate temperatures of 80 to 150 ° C. With suitable electrically conductive particles as fillers, sufficient electrical conductivity is obtained which corresponds to a low specific resistance value of, for example, 10 ⁇ ohm x cm. Without any sedimentation of the conductive particles being observed, the reactive resin mixture according to the invention can be used to produce electrically conductive layers up to a thickness of, for example, 50 ⁇ m. However, even thin adhesive joints from a thickness of approx. 2 ⁇ m can be easily cured with UV and fully cured thermally.
  • the electrically conductive layers or structures produced with the reaction resin mixture show good adhesion to metals, semiconductor surfaces or other organic and inorganic layers.
  • Electrically conductive adhesive connections produced with the reactive resin mixture have a high shear strength of, for example, 10 to 20 N / mm 2 . Due to the fast and at any temperature bare UV curing, it is possible to perform demanding adhesive tasks with the reactive resin mixture, which for example require exact and quick adjustment or a high dimensional stability of the applied adhesive layer during the curing process. Due to the thermal
  • Post-curing can also produce large-area electrically conductive bonds which are only accessible to UV radiation at the edge of the adhesive joint. Due to the UV curing, the adhesive points are fixed in such a way that during thermal post-curing there is no running of the reaction resin layer and no slipping of the fixed parts to be bonded.
  • the components of the reaction resin mixture can be selected so that they are low in corrosion-promoting ingredients such as free chlorides. They are therefore well suited for electronic applications.
  • the reaction resin mixture according to the invention has a resin matrix with components A to E in the following proportions:
  • Reaction resin mixture additionally as component F) 10 to 40 Volume percent, preferably 15 to 30 volume percent contain electrically conductive particles.
  • Cycloaliphatic epoxides are preferred for component A). These are largely harmless with regard to environmental compatibility and occupational safety. They can be represented in a highly pure and therefore low in corrosion-promoting ingredients. Commercial cycloaliphatic epoxides also include mixtures of several different cycloaliphatic epoxides. Suitable compounds obey, for example, the following structural formulas
  • epoxy resins or components containing epoxy groups are, for example, the glycidyl ethers and glycidyl esters widely used in industry.
  • suitable diluents are, for example, epoxidized olefins and polyolefins.
  • Component B) contains a compound containing hydroxyl groups, preferably a polyhydric, aliphatic or cycloaliphatic alcohol.
  • a compound containing hydroxyl groups preferably a polyhydric, aliphatic or cycloaliphatic alcohol.
  • glycols and other aliphatic diols, trifunctional or tetrafunctional alcohols such as trimethylolpropane or the ethers of glycols with phenols or bisphenols can be used.
  • More Suitable compounds are polymer polyols which are used in the production of polyurethanes.
  • the polyols offered by Dow Chemical under the names NIAX ® and TONE ® may serve as examples.
  • component B) those hydroxyl-containing compounds which are obtained by reacting epoxy compounds with alcohols or phenols.
  • the addition product of a cycloaliphatic is, for example, very suitable as component B)
  • Epoxy with a polyphenol preferably with a bisphenol such as bisphenol A.
  • a bisphenol such as bisphenol A.
  • Such addition products can be obtained under base conditions under mild conditions.
  • a preferred addition product is the 2: 1 adduct, in which one equivalent of phenolic groups is reacted with two equivalents of epoxy groups. Starting from a diepoxide and a bisphenol, the 2: 1 adduct is also a diepoxide.
  • the reaction mixture has practically no free phenolic OH groups if the reaction leading to the addition product is carried out in a molar ratio greater than 2: 1 to 20: 1 and preferably from 3: 1 to 10: 1.
  • the addition product may contain notable proportions of cycloaliphatic epoxide and thus unreacted epoxides corresponding to component A).
  • a cationic photoinitiator or a cationic photoinitiator system is contained as component C).
  • photoinitiators When UV irradiation occurs, these photoinitiators release reactive cations, for example protons, which initiate the cationic curing process of the epoxy resin.
  • the photoinitiators are derived from stable organic onium salts, especially with nitrogen, phosphorus, oxygen, sulfur, selenium or iodine as the central atom of the cation.
  • Aromatic sulfonium and iodonium salts with complex anions have proven to be particularly advantageous.
  • a photoinitiator which releases a Lewis acid and is implemented, for example, as a pi-donor transition metal complex is also possible.
  • Phenacylsulfonium salts, hydroxyphenylsulfonium salts and sulfoxonium salts should also be mentioned.
  • Onium salts can also be used, which are not stimulated directly by acid sensitization but rather by a sensitizer.
  • Organic silicon compounds which release a silicon on exposure to UV radiation in the presence of aluminum-organic compounds can also be used as photoinitiators for the cationic curing process.
  • the following sulfonium salt for example, is highly suitable as a photoinitiator. It is a main component of Cyracure ® UVI 6974 (Union Carbide):
  • a thiolanium salt is present as component D), which acts as a thermally activatable initiator.
  • Benzylthiolanium salts of the general structure are preferred:
  • Rl is hydrogen, alkyl, aryl, alkoxy, thioether, halogen, CN or N0 2 .
  • R2 is hydrogen, alkyl or aryl;
  • R3 is hydrogen, alkyl or aryl or an aromatic system condensed to the thiolane ring;
  • X ⁇ PF 6 ⁇ , AsF 6 "or Sb F ⁇
  • Unsubstituted benzylthiolanium salts are preferably used, in particular benzylthiolaniumhexafluoroantimonate.
  • Components E) which may contain customary additives, such as leveling agents, adhesion promoters, thixotropic agents, etc., are optionally present.
  • Component F) preferably contains metallic or at least metallic coated fillers.
  • Well-suited fillers are, for example, silver flakes or silver powder.
  • Metal-coated fillers, such as glass spheres coated with silver, are suitable to a limited extent.
  • the percolation threshold ie the filler content, above which a rapid increase in electrical conductivity is observed, is approximately 15 to 20 percent by volume for the specified electrically conductive particles.
  • the reaction resin mixture according to the invention has a particle content above the percolation threshold, which can be achieved for different particles with different filler contents.
  • the type and external shape of the electrically conductive particles are in principle of less importance than expected with regard to their suitability for the reactive resin mixture according to the invention.
  • the size and the shape of the filler particles influence the layer thickness that can be produced with the resin, but not the hardening properties. For example, flakes show little sedimentation, that is to say more flat and flake-shaped particles, while with powdery and more compact particles, comparable conductivity can only be achieved with a higher filler content.
  • the surface properties of the filler particles which the manufacturer has already provided with various unspecified coatings, e.g. with soaps.
  • Such coatings can be residues of solvents used in the manufacture or intentionally
  • FIG. 1 shows this finding on the basis of DSC measurements of two reaction resin mixtures. With the same resin matrix
  • reaction resin matrix has a thermally almost completely inhibited hardening, which can be seen from the absence of a hardening peak in the region of the hardening temperature.
  • Figure 1 shows the hardening behavior of two already mentioned
  • FIG. 2 shows an adhesive connection produced with the reaction resin mixture according to the invention in a schematic cross section.
  • FIG. 3 shows a multilayer conductor track structure which is also produced using the reaction resin mixture according to the invention.
  • the resin matrix VO is now mixed in seven preliminary tests, each with one of seven different fillers. 70 percent by weight of filler are chosen. Table 2 shows the fillers examined.
  • ADOH120 is the addition product of a cycloaliphatic epoxide CY177 and bisphenol A (Merck) in a ratio of 10: 2; CY177: cycloaliphatic epoxy; Cyracure UVI6974: cationic photoinitiator, triarylsulfonium salt.
  • VI to V5 are suitable for the reaction resin mixture according to the invention, V3 to V5 being only suitable to a limited extent.
  • VI and V2 show good curability both under UV and thermally.
  • Hardened layers of adhesive have good electrical conductivity. With V3, only a small penetration depth of the UV radiation is observed, so that in the case of thicker layers only skin formation is achieved by pure UV curing. Mixture V3 is therefore not suitable for UV curing thick layers.
  • the mixtures according to V4 and V5 can be hardened well, but then have only a low electrical conductivity, which makes them unsuitable for various applications.
  • the mixtures according to preliminary tests V6 and V7 show a massive inhibition of thermal curing, so that they are not suitable for the process according to the invention.
  • the silane A187 is an adhesion promoter, BYK A500 a defoamer and TCD alcohol a cycloaliphatic alcohol.
  • the reaction resin mixture RH1 is used for the production of conductor tracks.
  • Modified stencil printing is used to print conductor tracks with a cross section of 1.0 ⁇ 0.06 mm 2 and a length of 2 cm onto an insulating substrate (for example glass, aluminum oxide ceramic or polystyrene).
  • the curing takes place by UV radiation (for example 1.5 min with 50 mW / cm 2 ) and / or by increasing the temperature (for example 30 to 90 minutes to 120 to 150 ° C.). Shorter UV curing is also possible with thinner layers.
  • the conductor tracks After hardening, the conductor tracks have a resistance of 1.2 ohms, over which a specific resistance of 4 x 10 ⁇ 4 ohms x cm calculated. Further properties are a glass transition temperature of approx. 80 ° C, an expansion coefficient of 100 ppm below Tg and an elastic modulus of 3900 N / mm 2 .
  • E ⁇ shows itself as a major advantage that the printed structures remain dimensionally stable in the production process.
  • the resin itself is stable to viscosity in screen or stencil printing. As a preferred application, this enables the production of multilayer metallizations by multilayer printing.
  • FIG. 3 Resin structures of a first conductor track level L 1 are printed on the electrically insulating substrate S and hardened by means of UV.
  • an insulation layer I is printed, for which a reaction resin with the same reaction resin matrix is used, but without the electrically conductive particles (without component F).
  • the insulation layer I can be applied over the entire surface or in a structured manner in such a way that regions of the first conductor track level L1 which are provided for contacting the second conductor track level L2 remain uncovered.
  • the insulation layer I is also hardened with UV.
  • conductor track structures L2 of the second conductor track level are printed on and hardened with UV. In this case, the electrical contact between the first and second interconnect levels is produced in the areas not covered by the insulation layer I.
  • a further insulation layer can be applied over the entire surface (not shown in the figure).
  • the multilayered layer stack can then be cured together in a thermal process.
  • UV-curable resins for insulation layers are commercially available and can be used instead of the resin matrix according to the invention.
  • the reaction resin mixture RH2 is tested for fastening semiconductor chips. After curing, it has a specific resistance of less than 6 x 10 " ohms x cm, the resistance being measured on printed strips.
  • Figure 2 shows a semiconductor chip C, which was glued with the aid of an adhesive layer KS with its metallized back to a substrate S '.
  • the adhesive layer KS is applied in such a way that after the semiconductor chip C has been placed on its edge or on portions of the edge, a bead remains which is readily accessible to UV radiation.
  • UV radiation is used for hardening and the entire system is thermally hardened. Adhesive joints between 2 and 50 ⁇ m thick can be realized in this way.
  • additives such as deaerators, flow control agents, adhesion promoters, thixotropic agents are added to the resin systems, these additives being able to vary depending on the desired application.
  • the reactive resin mixture according to the invention can generally be seen where high conductivity is required. It is particularly suitable as an adhesive application for fastening chips (the bonds), for fastening components on printed circuit boards and hybrids, for producing printed conductors on printed circuit boards or ceramics and in particular for producing complex conductive geometries. It is applied using planar technology, preferably with screen printing or stamp printing or by dispenser application, for example with a robot-guided dispensing needle.

Abstract

L'invention concerne un mélange de résine de réaction à base d'époxyde pour produire des composés adhésifs électroconducteurs et des structures électroconductrices. Ce mélange peut durcir au moyen d'un système initiateur sélectionné, aussi bien par rayonnement ultraviolet que par voie thermique. Ce mélange de résine de réaction à un composant, stable au stockage, peut être appliqué, par exemple, par sérigraphie. Il durcit rapidement aux UV et complètement par voie thermique.
EP96946140A 1995-12-06 1996-12-04 Melange electroconducteur de resine de reaction Withdrawn EP0865653A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19545522 1995-12-06
DE19545522 1995-12-06
PCT/DE1996/002322 WO1997021229A2 (fr) 1995-12-06 1996-12-04 Melange electroconducteur de resine de reaction

Publications (1)

Publication Number Publication Date
EP0865653A2 true EP0865653A2 (fr) 1998-09-23

Family

ID=7779358

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96946140A Withdrawn EP0865653A2 (fr) 1995-12-06 1996-12-04 Melange electroconducteur de resine de reaction

Country Status (3)

Country Link
EP (1) EP0865653A2 (fr)
JP (1) JP2000501551A (fr)
WO (1) WO1997021229A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6020508A (en) * 1997-05-16 2000-02-01 National Starch And Chemical Investment Holding Corporation Radiation- or thermally-initiated cationically-curable epoxide compounds and compositions made from those compounds
AU711786B2 (en) * 1997-05-16 1999-10-21 National Starch And Chemical Investment Holding Corporation Reactive radiation- or thermally-initiated cationically- curable epoxide monomers and compositions made from those monomers
JP2002097443A (ja) * 2000-09-21 2002-04-02 Hitachi Chem Co Ltd 接着剤組成物及びこれを用いた回路接続材料並びに接続体
DE10062865A1 (de) * 2000-12-16 2002-07-04 Technoplast Beschichtungsgmbh Leitfähige, kratzfeste und bedruckbare Oberflächen
JP4949626B2 (ja) * 2002-09-04 2012-06-13 コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ ２つの板状の形状の物体を接着するための方法及び装置
JP5953131B2 (ja) * 2011-06-10 2016-07-20 積水化学工業株式会社 異方性導電材料、接続構造体及び接続構造体の製造方法
CN103087640A (zh) * 2011-11-08 2013-05-08 汉高股份有限公司 双固化粘合剂组合物及其用途以及粘合基底的方法
BR112015007082A2 (pt) * 2012-09-29 2017-07-04 3M Innovative Properties Co composição adesiva e fita adesiva
JP2015168803A (ja) 2014-03-10 2015-09-28 日立化成株式会社 導電性接着剤組成物、接続体、太陽電池モジュール及びその製造方法
WO2018180685A1 (fr) * 2017-03-30 2018-10-04 デクセリアルズ株式会社 Adhésif électroconducteur anisotrope et procédé de production de corps de connexion
JP2018178125A (ja) * 2018-06-26 2018-11-15 日立化成株式会社 導電性接着剤組成物、接続体、太陽電池モジュール及びその製造方法

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US4780371A (en) * 1986-02-24 1988-10-25 International Business Machines Corporation Electrically conductive composition and use thereof
DE3939628A1 (de) * 1989-11-30 1991-06-06 Siemens Ag Verfahren zur befestigung von bauelementen und integrierten halbleiterschaltungen auf schichtschaltungen
JPH04255776A (ja) * 1991-02-07 1992-09-10 Hitachi Chem Co Ltd 紫外線硬化型接着剤シートその製造法その製造法に用いる装置その接着剤シートを用いて配線板用基板を製造する方法およびその接着剤シートを用いて配線板を製造する方法
JPH06107913A (ja) * 1992-08-10 1994-04-19 Siemens Ag 反応樹脂混合物
JPH07268065A (ja) * 1993-11-17 1995-10-17 Sophia Syst:Kk 紫外線硬化型の無溶媒導電性ポリマー材料

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Title
See references of WO9721229A3 *

Also Published As

Publication number Publication date
WO1997021229A2 (fr) 1997-06-12
WO1997021229A3 (fr) 1997-08-07
JP2000501551A (ja) 2000-02-08

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