JP5533041B2 - Method for manufacturing conductive connection material, semiconductor device, and electronic apparatus - Google Patents

Description

  The present invention relates to a method for producing a conductive connection material, a method for connecting terminals, a method for forming connection terminals, a semiconductor device, and an electronic apparatus.

  In recent years, along with the demand for higher functionality and miniaturization of electronic equipment, the pitch between connection terminals in electronic materials is becoming increasingly narrow, and the connection between terminals in a fine wiring circuit is also becoming more sophisticated.

As a connection method between the terminals, for example, the following method is used when the terminals included in the IC chip are electrically connected to the terminals included in the circuit board.
That is, first, a solder layer is formed on the surface of the terminal provided in the circuit board. Then, the terminals to be connected are in contact with each other via the solder layer, and the solder layer is heated and melted, and then solidified again to electrically connect the terminals via the solder layer. Can be made.

  In the connection method between the terminals as described above, it is necessary to form a solder layer on the surface of the terminal included in the circuit board, and a plating method or a printing method is used for forming the solder layer (for example, patents) References 1 and 2). According to these methods, a solder layer can be collectively formed on the surfaces of a plurality of terminals.

However, when the plating method is used, an apparatus for forming the solder layer becomes large, and a lot of man-hours are required for the management of the chemical solution. Furthermore, since it is necessary to provide a plating lead on the terminal, it is difficult to form the solder layer on a high-density terminal (wiring) with high patterning accuracy. Further, when a thick solder layer is formed, it takes a long time, so that it is not suitable for forming a solder layer having such a configuration.
Further, when the printing method is used, if the solder layer is not suitable for forming a thin solder layer or if the terminal has a high density, the solder layer is formed on the surface of the terminal with excellent accuracy. There was a problem that I could not.

JP-A 63-256268 Japanese Patent Laid-Open No. 03-018092

  An object of the present invention is to provide a method for producing a conductive connection material capable of connecting between terminals or forming a connection terminal with high accuracy even if the terminals are dense, without using a large-scale device, and such a conductive connection. It is an object to provide a highly reliable connection method between terminals, a terminal formation method, a highly reliable semiconductor device, and an electronic device using a conductive connection material manufactured by a material manufacturing method.

Such an object is achieved by the present invention described in the following (1) to (16).
(1) A metal layer forming step of forming an alloy containing tin as a main component or a metal layer of tin on a supporting substrate by a vacuum sputtering method or a vacuum deposition method, and a first resin composition layer containing a resin component A first resin composition layer forming step to be formed; and transferring the metal layer from the support substrate to at least one surface of the first resin composition layer, thereby forming the first resin composition and the A metal layer transfer step of laminating a metal layer, and a method for producing a conductive connection material,
(2) A second resin composition forming step of forming a second resin composition layer containing a resin component on the surface of the metal layer opposite to the surface in contact with the first resin composition layer. A method for producing the conductive connection material according to (1),
(3) The metal layer includes tin (Sn), lead (Pb), silver (Ag), bismuth (Bi), indium (In), zinc (Zn), nickel (Ni), antimony (Sb), iron ( Fe), aluminum (Al), gold (Au), germanium (Ge), and an alloy of at least two metals selected from the group consisting of copper (Cu), a simple substance of tin or indium (1) or ( 2) A method for producing a conductive connecting material according to 2),
(4) The method for producing a conductive connecting material according to any one of (1) to (3), wherein the metal layer is composed mainly of a Sn—Pb alloy, a Sn—Ag—Cu alloy, or a Sn—Ag alloy. (5) The method for producing a conductive connecting material according to any one of (1) to (4), wherein the metal layer is composed of a Sn-37Pb alloy or a Sn-3.0Ag-0.5Cu alloy as a main material. (6) The first resin composition layer and the second resin composition layer are composed of a resin composition containing the resin component and a compound having a flux function. A method for producing the conductive connecting material according to claim 1,
(7) The method for producing a conductive connecting material according to (6), wherein the compound having a flux function includes a compound having at least one of a phenolic hydroxyl group and a carboxyl group.
(8) The method for producing a conductive connecting material according to (6), wherein the compound having the flux function includes a compound represented by the following general formula (1):
_{HOOC- (CH 2) n-COOH} ····· (1)
(In Formula (1), n is an integer of 1-20.)
(9) The compound having the flux function includes at least one of the compounds represented by the following general formula (2) and the following general formula (3). Production method,
[Wherein, R ^{1 to} R ⁵ are each independently a monovalent organic group, and at least one of R ^{1 to} R ⁵ is a hydroxyl group. ]
[Wherein, R ^{6 to} R ²⁰ are each independently a monovalent organic group, and at least one of R ^{6 to} R ²⁰ is a hydroxyl group or a carboxyl group. ]
(10) In the said resin composition, content of the compound which has the said flux function is 1-50 weight%, The manufacturing method of the conductive connection material in any one of (6) thru | or (9),
(11) An arrangement in which the conductive connection material manufactured by the method for manufacturing a conductive connection sheet according to any one of (1) to (11) is disposed between a terminal included in the base material and a terminal included in the counter base material. Process,
A heating step of heating the conductive connection sheet at a temperature that is equal to or higher than the melting point of the metal material and the curing of the resin composition layer is not completed, and a curing step of curing the resin composition layer,
At least one of the terminal of the base material or the terminal of the counter base material protrudes from the base material or the counter base material, and in the arrangement step, the first resin composition layer is on the protruding terminal side. A connection method between terminals, characterized in that the conductive connection sheet is arranged to be positioned;
(12) An arrangement in which the conductive connection material manufactured by the method for manufacturing a conductive connection material according to any one of (1) to (11) is disposed between a terminal included in the base material and a terminal included in the counter base material. Process,
A heating step of heating the conductive connection sheet at a temperature that is equal to or higher than the melting point of the metal material and the softening of the resin composition layer; and a solidification step of solidifying the resin composition layer, At least one of the terminal of the substrate or the terminal of the counter substrate protrudes from the substrate or the counter substrate, and the first resin composition layer is positioned on the protruding terminal side in the arranging step. A connection method between terminals, characterized in that the conductive connection sheet is disposed on
(13) An arrangement step of arranging the conductive connection material manufactured by the method for manufacturing a conductive connection material according to any one of (1) to (11) on a base material having terminals, and a melting point of the metal material or higher And a heating step of heating the conductive connecting material at a temperature at which the curing of the resin composition layer is not completed, and the terminal of the base material protrudes from the base material, and in the placement step, A method of forming a connection terminal, characterized in that the conductive connection material is disposed so that the first resin composition layer is located on the terminal side;
(14) An arrangement step of arranging the conductive connection material manufactured by the method for manufacturing a conductive connection material according to any one of (1) to (11) on a base material having terminals, and a melting point of the metal material or higher And a heating step of heating the conductive connecting material at a temperature at which the resin composition layer is softened, and a terminal of the base material protrudes from the base material, On the side, the conductive connection material is arranged so that the first resin composition layer is located;
(15) Terminals facing each other are electrically connected via a connection portion formed using a conductive connection material manufactured by the method for manufacturing a conductive connection material according to any one of (1) to (11). A semiconductor device which is characterized by being made.
(16) The terminals facing each other are electrically connected via a connection portion formed using the conductive connection material manufactured by the method for manufacturing a conductive connection material according to any one of (1) to (11). Electronic device characterized by being made.

  According to the present invention, without using a large-scale device, a method for manufacturing a conductive connection material capable of connecting between terminals or forming a connection terminal with high accuracy even between high-density terminals, and such conductive connection A highly reliable connection method between terminals, a terminal formation method, a highly reliable semiconductor device, and an electronic device using the conductive connection material manufactured by the material manufacturing method can be provided.

It is a plane schematic diagram which shows an example of the shape of the metal layer used for this invention. In the connection method between terminals of this invention, it is sectional drawing which shows roughly an example of the state of the board | substrate after arrange | positioning a conductive connection material between terminals, and a conductive connection material. In the connection method between the terminals of this invention, it is sectional drawing which shows roughly an example of the state of the board | substrate after heating and hardening / solidifying the conductive connection material arrange | positioned between terminals, an electroconductive area | region, and an insulating area | region. In the connection method between terminals of this invention, it is sectional drawing which shows roughly an example of the state of the board | substrate after arrange | positioning a conductive connection material between terminals, and a conductive connection material. In the manufacturing method of the connection terminal of this invention, it is sectional drawing which shows roughly an example of the state of a board | substrate after arrange | positioning a conductive connection material on the electrode provided on the board | substrate, and a conductive connection material. In the manufacturing method of the connection terminal of this invention, it is sectional drawing which shows roughly an example of the state of a board | substrate after arrange | positioning a conductive connection material on the electrode provided on the board | substrate, and a conductive connection material. In the manufacturing method of the connection terminal of this invention, it is sectional drawing which shows roughly an example of the state of the board | substrate, a conductive area | region, and an insulating area | region after heating and hardening / solidifying the conductive connection material arrange | positioned on the electrode of a board | substrate. is there.

  Hereinafter, the method for producing a conductive connection material, the method for connecting terminals, the method for forming connection terminals, the semiconductor device, and the electronic device according to the present invention will be specifically described.

1. Conductive connection material The conductive connection material obtained by the manufacturing method of the conductive connection material of this invention is comprised from the resin composition layer and the alloy or tin metal layer which has tin as a main component. The form is a laminate having a multilayer structure composed of a resin composition layer and a metal layer, and each of the resin composition layer and the metal layer may be a single layer or a plurality of layers. The metal layer of the conductive connecting material is produced by transferring a metal layer formed directly on the supporting base material by vacuum sputtering or vacuum vapor deposition from the supporting base material onto the resin composition, and the laminated structure is particularly limited. Alternatively, a two-layer structure (resin composition layer / metal layer) of a resin composition layer and a metal layer may be used, or a three-layer structure including a plurality of either or both of the resin composition layer and the metal layer, or more A multilayer structure may be used. In addition, when using two or more resin composition layers or metal layers, the composition of each layer may be the same or different.

In one embodiment of the present invention, the upper and lower layers of the metal layer are preferably resin composition layers from the viewpoint of reducing the surface oxide film of the metal layer with a compound having a flux function. For example, a three-layer structure (resin composition layer / metal layer / resin composition layer) is preferable. In this case, the thickness of the resin composition layer on both sides of the metal layer may be the same or different. The thickness of the resin composition layer may be appropriately adjusted depending on the conductor thickness of the terminal to be connected. For example, when manufacturing a connection terminal using conductive connection materials having different thicknesses of the resin composition layers on both sides of the metal layer, it is preferable to arrange the thinner one on one connection terminal side (electrode side). Thus, by shortening the distance between the metal layer and the connection terminal, it becomes easier to control the aggregation of tin or the alloy mainly composed of tin on the connection terminal portion.

  In another embodiment of the present invention, for example, when manufacturing a connection terminal on an electronic member such as a semiconductor wafer, if the conductive connection material has a resin composition layer only on one side of the metal layer, a part of the metal layer Can be exposed. When connecting opposing connection terminals using a conductive connection material having a two-layer structure, the resin composition layer side may be disposed so as to contact the connection terminal, or the metal layer side may be disposed so as to contact the connection terminal. However, it is preferable to arrange the metal layer side so as to be in contact with the connection terminal because it is easy to be mounted on the terminal. When connecting connection terminals of opposing electronic members using a conductive connection material having a two-layer structure, the conductive connection material is attached to both of the opposing electronic members, and then the electronic member with the conductive connection material is attached. However, a conductive connection material having a two-layer structure may be attached to one terminal side, only the resin composition layer may be attached to the other terminal side, and then the electronic members may be attached to each other.

  Next, the resin composition and metal layer used in the present invention will be described.

(1) Resin composition layer In this invention, a resin composition layer is comprised with the resin composition containing a resin component. The resin composition may be in a liquid or solid form at normal temperature. Here, “liquid at normal temperature” means a state where there is no fixed form at normal temperature (25 ° C.). Paste forms are also included in liquid form.

  In the present invention, any of a curable resin composition and a thermoplastic resin composition may be used as the resin composition. Examples of the curable resin composition used in the present invention include those that are cured by heating or irradiation with actinic radiation. A thermosetting resin composition is preferable in that it is excellent in mechanical properties such as linear expansion coefficient and elastic modulus after curing. The thermoplastic resin composition used in the present invention is not particularly limited as long as it is flexible enough to be molded by heating to a predetermined temperature.

(A) Curable resin composition In addition to the curable resin, the curable resin composition used in the present invention, if necessary, a film-forming resin, a curing agent, a curing accelerator, a compound having a flux function, Silane coupling agents, fillers and the like are included.

(I) Curable resin The curable resin used by this invention will not be specifically limited if normally used as an adhesive component for semiconductor device manufacture. For example, epoxy resin, phenoxy resin, silicone resin, oxetane resin, phenol resin, (meth) acrylate resin, polyester resin (unsaturated polyester resin), diallyl phthalate resin, maleimide resin, polyimide resin (polyimide precursor resin), bismaleimide -Triazine resin etc. are mentioned. In particular, the use of a thermosetting resin containing at least one selected from the group consisting of epoxy resins, (meth) acrylate resins, phenoxy resins, polyester resins, polyimide resins, silicone resins, maleimide resins, and bismaleimide-triazine resins. preferable. Especially, it is preferable to use an epoxy resin from a viewpoint that it is excellent in sclerosis | hardenability and preservability, the heat resistance of a hardened | cured material, moisture resistance, and chemical resistance. These curable resins may be used alone or in combination of two or more.

Content of curable resin can be suitably set according to the form of curable resin composition.
For example, when the curable resin composition is liquid, the content of the curable resin is preferably 10% by weight or more, more preferably 15% by weight or more, and more preferably 20% by weight with respect to the total weight of the curable resin composition. The above is more preferable, 25% by weight or more is further more preferable, 30% by weight or more is still more preferable, and 35% by weight or more is particularly preferable. Further, it is preferably less than 100% by weight, more preferably 95% by weight or less, still more preferably 90% by weight or less, still more preferably 75% by weight or less, still more preferably 65% by weight or less, and particularly preferably 55% by weight or less.
When the curable resin composition is solid, the content of the curable resin is preferably 5% by weight or more, more preferably 10% by weight or more, and more preferably 15% by weight with respect to the total weight of the curable resin composition. The above is more preferable, and 20% by weight or more is particularly preferable. Moreover, 90 weight% or less is preferable, 85 weight% or less is more preferable, 80 weight% or less is further more preferable, 75 weight% or less is still more preferable, 65 weight% or less is still more preferable, 55 weight% or less is especially preferable.
When the content of the curable resin is within the above range, the electrical connection strength and the mechanical adhesive strength between the terminals can be sufficiently secured.

  In the present invention, any epoxy resin that is liquid at room temperature and solid at room temperature may be used. An epoxy resin that is liquid at room temperature and an epoxy resin that is solid at room temperature may be used in combination. When the curable resin composition is liquid, it is preferable to use a liquid epoxy resin at room temperature, and when the curable resin composition is solid, use either a liquid or solid epoxy resin. However, when a solid epoxy resin is used, it is preferable to use a film-forming resin in combination.

Preferred examples of the epoxy resin that is liquid at room temperature (25 ° C.) include bisphenol A type epoxy resins and bisphenol F type epoxy resins. A bisphenol A type epoxy resin and a bisphenol F type epoxy resin may be used in combination.
The epoxy equivalent of the epoxy resin that is liquid at room temperature is preferably 150 to 300 g / eq, more preferably 160 to 250 g / eq, and particularly preferably 170 to 220 g / eq. If the epoxy equivalent is less than the above lower limit, the shrinkage of the cured product tends to increase, and warping may occur. On the other hand, when the upper limit is exceeded, when a film-forming resin is used in combination, the reactivity with a film-forming resin, particularly a polyimide resin, tends to decrease.

Examples of solid epoxy resins at room temperature (25 ° C.) include bisphenol A type epoxy resins, bisphenol S type epoxy resins, phenol novolac type epoxy resins, cresol novolac type epoxy resins, glycidyl amine type epoxy resins, and glycidyl ester type epoxies. Resin, trifunctional epoxy resin, tetrafunctional epoxy resin, etc. are mentioned. Among these, solid trifunctional epoxy resin, cresol novolac type epoxy resin and the like are preferable. These epoxy resins may be used alone or in combination of two or more.
The epoxy equivalent of the epoxy resin solid at room temperature is preferably 150 to 3000 g / eq, more preferably 160 to 2500 g / eq, and particularly preferably 170 to 2000 g / eq.
The softening point of the epoxy resin solid at room temperature is preferably 40 to 120 ° C, more preferably 50 to 110 ° C, and particularly preferably 60 to 100 ° C. When the softening point is within the above range, tackiness can be suppressed and handling can be easily performed.

(Ii) Film-forming resin When a solid curable resin composition is used, it is preferable to use the curable resin and the film-forming resin in combination. The film-forming resin used in the present invention is not particularly limited as long as it is soluble in an organic solvent and has a film-forming property alone. Either a thermoplastic resin or a thermosetting resin can be used, and these can be used in combination. Specifically, as the film-forming resin, (meth) acrylic resin, phenoxy resin, polyester resin (saturated polyester resin), polyurethane resin, polyimide resin, polyamideimide resin, siloxane-modified polyimide resin, polybutadiene resin, polypropylene resin, Styrene-butadiene-styrene copolymer, styrene-ethylene-butylene-styrene copolymer, polyacetal resin, polyvinyl butyral resin, polyvinyl acetal resin, butyl rubber, chloroprene rubber, polyamide resin, acrylonitrile-butadiene copolymer, acrylonitrile-butadiene- Acrylic acid copolymer, acrylonitrile-butadiene-styrene copolymer, polyvinyl acetate, nylon and the like can be mentioned. Among these, (meth) acrylic resins, phenoxy resins, polyester resins, and polyimide resins are preferable. A film-forming resin may be used alone or in combination of two or more.

  In this specification, “(meth) acrylic resin” refers to a polymer of (meth) acrylic acid and its derivatives, or a copolymer of (meth) acrylic acid and its derivatives and other monomers. Means. When expressed as “(meth) acrylic acid” or the like, it means “acrylic acid or methacrylic acid” or the like.

  Examples of the (meth) acrylic resin used in the present invention include polyacrylic acid such as polyacrylic acid, polymethacrylic acid, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, and poly-2-ethylhexyl acrylate. Esters, polymethacrylates such as polymethyl methacrylate, polyethyl methacrylate, polybutyl methacrylate, polyacrylonitrile, polymethacrylonitrile, polyacrylamide, butyl acrylate-ethyl acrylate-acrylonitrile copolymer, acrylonitrile-butadiene Copolymer, acrylonitrile-butadiene-acrylic acid copolymer, acrylonitrile-butadiene-styrene copolymer, acrylonitrile-styrene copolymer, methyl methacrylate-styrene copolymer, methacrylate Acid methyl-acrylonitrile copolymer, methyl methacrylate-α-methylstyrene copolymer, butyl acrylate-ethyl acrylate-acrylonitrile-2-hydroxyethyl methacrylate-methacrylic acid copolymer, butyl acrylate-ethyl acrylate- Acrylonitrile-2-hydroxyethyl methacrylate-acrylic acid copolymer, butyl acrylate-acrylonitrile-2-hydroxyethyl methacrylate copolymer, butyl acrylate-acrylonitrile-acrylic acid copolymer, butyl acrylate-ethyl acrylate-acrylonitrile Examples thereof include a copolymer and an ethyl acrylate-acrylonitrile-N, N-dimethylacrylamide copolymer. Of these, butyl acrylate-ethyl acrylate-acrylonitrile copolymer and ethyl acrylate-acrylonitrile-N, N-dimethylacrylamide are preferable. These (meth) acrylic resins may be used alone or in combination of two or more.

  Although the skeleton of the phenoxy resin used in the present invention is not particularly limited, bisphenol A type, bisphenol F type, biphenyl type, and the like are preferable.

  The polyimide resin used in the present invention is not particularly limited as long as the resin has an imide bond in the repeating unit. For example, what is obtained by making diamine and acid dianhydride react, heating the obtained polyamic acid, and carrying out dehydration ring closure is mentioned.

  Examples of the diamine include aromatic diamines such as 3,3′-dimethyl-4,4′diaminodiphenyl, 4,6-dimethyl-m-phenylenediamine, and 2,5-dimethyl-p-phenylenediamine, Examples thereof include siloxane diamines such as 3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane. A diamine may be used individually by 1 type, or may use 2 or more types together.

Examples of the acid dianhydride include 3,3,4,4′-biphenyltetracarboxylic acid, pyromellitic dianhydride, 4,4′-oxydiphthalic dianhydride, and the like. An acid dianhydride may be used individually by 1 type, or may use 2 or more types together.

  The polyimide resin may be soluble or insoluble in a solvent, but is preferably a solvent-soluble one because it can be easily varnished when mixed with other components and has excellent handleability. In particular, a siloxane-modified polyimide resin is preferably used because it can be dissolved in various organic solvents.

  The weight average molecular weight of the film-forming resin used in the present invention is preferably 8,000 to 1,000,000, more preferably 8,500 to 950,000, and still more preferably 9,000 to 900,000. When the weight average molecular weight of the film-forming resin is within the above range, the film-forming property can be improved, and the fluidity of the conductive connecting material before curing can be suppressed. The weight average molecular weight of the film-forming resin can be measured by GPC (gel permeation chromatography).

  In the present invention, commercially available products can be used as such film-forming resins. Furthermore, as long as the effect of the present invention is not impaired, a film-forming resin may be used in which various additives such as a plasticizer, a stabilizer, an antistatic agent, an antioxidant, a filler and a pigment are blended. Good.

In the conductive connection material used in the present invention, the content of the film-forming resin can be appropriately set according to the form of the curable resin composition to be used.
For example, in the case of a solid curable resin composition, the content of the film-forming resin is preferably 5% by weight or more with respect to the total weight of the curable resin composition, and is 10% by weight or more. It is more preferable that the content is 15% by weight or more. Further, it is preferably 50% by weight or less, more preferably 45% by weight or less, and particularly preferably 40% by weight or less. When the content of the film-forming resin is within the above range, the fluidity of the curable resin composition before melting can be suppressed, and the conductive connecting material can be easily handled.

(Iii) Curing Agent Preferred examples of the curing agent used in the present invention include phenols, acid anhydrides, and amine compounds. A hardening | curing agent can be suitably selected according to the kind etc. of curable resin. For example, when an epoxy resin is used as the curable resin, good reactivity with the epoxy resin, low dimensional change during curing, and appropriate physical properties after curing (for example, heat resistance, moisture resistance, etc.) are obtained. Phenols are preferably used as the curing agent, and bifunctional or higher functional phenols are more preferable in terms of excellent physical properties after curing of the curable resin. Moreover, such a hardening | curing agent may be used individually by 1 type, and may use 2 or more types together.

  Examples of the phenols include bisphenol A, tetramethylbisphenol A, diallyl bisphenol A, biphenol, bisphenol F, diallyl bisphenol F, trisphenol, tetrakisphenol, phenol novolac resin, and cresol novolac resin. Of these, phenol novolac resins and cresol novolac resins are preferable because they have good reactivity with epoxy resins and excellent physical properties after curing.

When the content of the curing agent has a functional group that functions as a curing agent when the compound having a flux function described below and the type of the curable resin or the curing agent to be used have a functional group, the content should be selected as appropriate. Can do.
For example, when an epoxy resin is used as the curable resin, the content of the curing agent is preferably 0.1 to 50% by weight and more preferably 0.2 to 40% by weight with respect to the total weight of the curable resin composition. 0.5 to 30% by weight is preferable. When the content of the curing agent is within the above range, the electrical connection strength between the terminals and the mechanical adhesive strength can be sufficiently secured.

(Iv) Curing accelerator The curing accelerator used in the present invention is imidazole, 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole. 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl- 4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate 2 , 4-Diamino-6- [2'-methylimidazolyl (1 ')]-ethyl-s-triazine, 2,4-diamino-6- [2'-undecylimidazolyl (1')]-ethyl-s- Triazine, 2,4-diamino-6- [2'-ethyl-4-methylimidazolyl (1 ')]-ethyl-s-triazine, 2,4-diamino-6- [2'-methylimidazolyl (1') ] Isocyanuric acid adduct of 2-ethyl-s-triazine, isocyanuric acid adduct of 2-phenylimidazole, isocyanuric acid adduct of 2-methylimidazole, 2-phenyl-4,5-dihydroxydimethylimidazole, 2-phenyl-4 -Imidazole compounds such as methyl-5-hydroxymethylimidazole.

Content of a hardening accelerator can be suitably set according to the kind of hardening accelerator to be used.
For example, when an imidazole compound is used, the content of the imidazole compound is preferably 0.001% by weight or more, more preferably 0.003% by weight or more, based on the total weight of the curable resin composition. 0.005% by weight or more is particularly preferable. Moreover, 1.0 weight% or less is preferable, 0.7 weight% or less is more preferable, and 0.5 weight% or less is especially preferable. When the content of the imidazole compound is less than the lower limit, the effect as a curing accelerator is not sufficiently exhibited, and the curable resin composition may not be sufficiently cured. On the other hand, if the content of the imidazole compound exceeds the above upper limit, the alloy containing tin as a main component or tin does not sufficiently move to the terminal surface before the curing of the curable resin composition is completed, and the insulating region has tin. In some cases, an alloy containing tin as a main component or tin remains, and sufficient insulation cannot be secured. In addition, the storage stability of the conductive connection material may be reduced.

(V) Compound having a flux function The compound having a flux function used in the present invention has an action of reducing a metal oxide film such as a surface oxide film of a terminal and a metal layer. For example, the compound having a flux function is preferably a compound having a phenolic hydroxyl group and / or a carboxyl group. Examples of the compound having a phenolic hydroxyl group include phenol, o-cresol, 2,6-xylenol, p-cresol, m-cresol, o-ethylphenol, 2,4-xylenol, 2,5-xylenol, m- Ethylphenol, 2,3-xylenol, meditol, 3,5-xylenol, p-tert-butylphenol, catechol, p-tert-amylphenol, resorcinol, p-octylphenol, p-phenylphenol, bisphenol F, bisphenol AF, biphenol Monomers containing phenolic hydroxyl groups such as diallyl bisphenol F, diallyl bisphenol A, trisphenol, tetrakisphenol, phenol novolac resins, o-cresol novolac resins, bisphenols Nord F novolak resins, resins containing a phenolic hydroxyl group such as bisphenol A novolac resin.

Examples of the compound having a carboxyl group include aliphatic acid anhydrides, alicyclic acid anhydrides,
Aromatic acid anhydrides, aliphatic carboxylic acids, aromatic carboxylic acids and the like can be mentioned. Examples of the aliphatic acid anhydride include succinic anhydride, polyadipic acid anhydride, polyazeline acid anhydride, and polysebacic acid anhydride. Examples of the alicyclic acid anhydride include methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylhymic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, methylcyclohexene dicarboxylic acid. An anhydride etc. are mentioned. Examples of the aromatic acid anhydride include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic anhydride, ethylene glycol bistrimellitate, and glycerol tris trimellitate.

Examples of the aliphatic carboxylic acid include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, acrylic acid, methacrylic acid, crotonic acid, Examples include oleic acid, fumaric acid, maleic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, dodecanedioic acid, and pimelic acid. Among them, the following formula (1):
_{HOOC- (CH 2) n -COOH (} 1)
(In Formula (1), n is an integer of 1-20.)
Are preferable, and adipic acid, sebacic acid, and dodecanedioic acid are more preferable.

The structure of the aromatic carboxylic acid is not particularly limited, but a compound represented by the following formula (2) or (3) is preferable.
[Wherein, R ^{1 to} R ⁵ are each independently a monovalent organic group, and at least one of R ^{1 to} R ⁵ is a hydroxyl group. ]
[Wherein, R ^{6 to} R ²⁰ are each independently a monovalent organic group, and at least one of R ^{6 to} R ²⁰ is a hydroxyl group or a carboxyl group. ]

  Aromatic carboxylic acids include benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, trimesic acid, merophanic acid, platnic acid, pyromellitic acid, meritic acid, xylylic acid, hemelitonic acid, mesitylene Acid, prenylic acid, toluic acid, cinnamic acid, salicylic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, gentisic acid (2,5-dihydroxybenzoic acid), 2,6-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, gallic acid (3,4,5-trihydroxybenzoic acid), 4-dihydroxy-2-naphthoic acid, 3,5-dihydroxy-2-naphthoic acid, 3,5-2 Examples include naphthoic acid derivatives such as dihydroxy-2-naphthoic acid; phenolphthaline; diphenolic acid and the like.

  Among these, in the present invention, a compound that not only has a flux function but also acts as a curing agent for the curable resin is preferable. That is, as the compound having a flux function used in the present invention, a compound having a functional group capable of reacting with a curable resin and exhibiting an action of reducing a metal surface oxide film such as a metal layer and a terminal is used. preferable. The functional group is appropriately selected depending on the type of curable resin. For example, when an epoxy resin is used as the curable resin, the functional group is preferably a functional group capable of reacting with an epoxy group such as a carboxyl group, a hydroxyl group, and an amino group. The compound having the flux function also acts as a curing agent, thereby reducing the metal surface oxide film such as the metal layer and the terminal to increase the wettability of the metal surface, facilitating the formation of the conductive region, and conducting After forming the property region, it can be added to the curable resin to increase the elastic modulus or Tg of the resin. In addition, since the compound having a flux function acts as a curing agent, there is an advantage that flux cleaning is not required and the occurrence of ion migration due to the remaining flux component can be suppressed.

The compound having such a flux function preferably has at least one carboxyl group. For example, when an epoxy resin is used as the curable resin, examples of the compound include aliphatic dicarboxylic acids or compounds having a carboxyl group and a phenolic hydroxyl group.
Preferred examples of the aliphatic dicarboxylic acid include compounds in which two carboxyl groups are bonded to an aliphatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated acyclic, or may be saturated or unsaturated cyclic. Further, when the aliphatic hydrocarbon group is acyclic, it may be linear or branched.

  As such aliphatic dicarboxylic acid, the compound whose n is an integer of 1-20 in the said Formula (1) is mentioned preferably. When n in the formula (1) is within the above range, the balance between the flux activity, the outgas at the time of bonding, the elastic modulus after the conductive connecting material is cured, and the glass transition temperature becomes good. In particular, n is preferably 3 or more because an increase in the elastic modulus after curing of the conductive connecting material can be suppressed and the adhesion to the adherend can be improved. In addition, n is preferably 10 or less because it is possible to suppress a decrease in elastic modulus and further improve connection reliability.

  Examples of the aliphatic dicarboxylic acid represented by the formula (1) include glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecane. Examples include diacid, octadecanedioic acid, nonadecanedioic acid, and eicosanedioic acid. Among these, adipic acid, suberic acid, sebacic acid and dodencandioic acid are preferable, and sebacic acid is particularly preferable.

  Examples of the compound having a carboxyl group and a phenolic hydroxyl group include salicylic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, gentisic acid (2,5-dihydroxybenzoic acid), and 2,6-dihydroxybenzoic acid. Benzoic acid derivatives such as acid, 3,4-dihydroxybenzoic acid, gallic acid (3,4,5-trihydroxybenzoic acid); 1,4-dihydroxy-2-naphthoic acid, 3,5-dihydroxy-2- Naphthoic acid derivatives such as naphthoic acid; phenolphthaline; diphenolic acid and the like. Of these, phenolphthaline, gentisic acid, 2,4-dihydroxybenzoic acid, and 2,6-dihydroxybenzoic acid are preferable, and phenolphthalin and gentisic acid are particularly preferable.

  A compound having a flux function may be used alone or in combination of two or more. Moreover, since any compound easily absorbs moisture and causes voids, it is preferable to dry the compound having a flux function in advance before use.

Content of the compound which has a flux function can be suitably set according to the form of the resin composition to be used.
For example, when the resin composition is liquid, the content of the compound having a flux function is preferably 1% by weight or more, more preferably 2% by weight or more, more preferably 3% by weight with respect to the total weight of the curable resin composition. % Or more is particularly preferable. Moreover, 50 weight% or less is preferable, 40 weight% or less is more preferable, 30 weight% or less is further more preferable, and 25 weight% or less is especially preferable.
In the case of a solid resin composition, the content of the compound having a flux function is preferably 1% by weight or more, more preferably 2% by weight or more, more preferably 3% by weight with respect to the total weight of the curable resin composition. % Or more is particularly preferable. Moreover, 50 weight% or less is preferable, 40 weight% or less is more preferable, 30 weight% or less is further more preferable, and 25 weight% or less is especially preferable.
When the content of the compound having the flux function is within the above range, the metal layer and the surface oxide film of the terminal can be removed to such an extent that they can be electrically joined. Further, when the resin composition is a curable resin, it can be efficiently added to the resin at the time of curing to increase the elastic modulus or Tg of the resin. Moreover, generation | occurrence | production of the ion migration resulting from the compound which has an unreacted flux function can be suppressed.

(Vi) Silane coupling agent Examples of the silane coupling agent used in the present invention include an epoxy silane coupling agent and an aromatic-containing aminosilane coupling agent. By adding the silane coupling agent, the adhesion between the bonding member and the conductive connecting material can be enhanced. A silane coupling agent may be used individually by 1 type, and may use 2 or more types together.

  Content of a silane coupling agent can be suitably selected according to types, such as a joining member and curable resin. For example, the content of the silane coupling agent is preferably 0.01% by weight or more, more preferably 0.05% by weight or more, and particularly preferably 0.1% by weight or more with respect to the total weight of the curable resin composition. It is preferably 2% by weight or less, more preferably 1.5% by weight or less, and particularly preferably 1% by weight or less.

  The curable resin composition used in the present invention contains a plasticizer, a stabilizer, a tackifier, a lubricant, a filler, an antistatic agent, an antioxidant, a pigment, and the like as long as the effects of the present invention are not impaired. May be.

  In the present invention, the curable resin composition can be prepared by mixing and dispersing the above components. The mixing method and dispersion method of each component are not specifically limited, It can mix and disperse | distribute by a conventionally well-known method.

  Moreover, in this invention, you may mix the said each component in a solvent or under absence of solvent, and may prepare a liquid curable resin composition. The solvent used at this time is not particularly limited as long as it is inert to each component. For example, acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), diisobutyl ketone (DIBK), cyclohexanone, Ketones such as diacetone alcohol (DAA); aromatic hydrocarbons such as benzene, xylene and toluene; alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol and n-butyl alcohol; methyl cellosolve, ethyl cellosolve, butyl cellosolve; Cellosolves such as methyl cellosolve acetate and ethyl cellosolve acetate, N-methyl-2-pyrrolidone (NMP), tetrahydrofuran (THF), dimethylformamide (DMF), dibasic acid ester (DB ), Ethyl 3-ethoxypropionate (EEP), and dimethyl carbonate (DMC). Moreover, it is preferable that the usage-amount of a solvent is an quantity from which the solid content concentration of the component mixed with the solvent will be 10 to 60 weight%.

(B) Thermoplastic resin composition In this invention, a thermoplastic resin composition can also be used as a resin composition.
The thermoplastic resin composition used in the present invention includes a compound having a flux function, a silane coupling agent, and the like, as necessary, in addition to the thermoplastic resin and the filler.

(I) Thermoplastic resin Examples of the thermoplastic resin used in the present invention include vinyl acetate, polyvinyl alcohol resin, polyvinyl butyral resin, vinyl chloride resin, (meth) acrylic resin, phenoxy resin, polyester resin, polyimide resin, and polyamide. Imide resin, siloxane-modified polyimide resin, polybutadiene resin, acrylic resin, styrene resin, polyethylene resin, polypropylene resin, polyamide resin, cellulose resin, isobutylene resin, vinyl ether resin, liquid crystal polymer resin, polyphenylene sulfide resin, polyphenylene ether resin, polyether mon Phon resin, polyether imide resin, polyether ether ketone resin, polyurethane resin, styrene-butadiene-styrene copolymer, styrene-ethylene-buty Lene-styrene copolymer, polyacetal resin, polyvinyl butyral resin, polyvinyl acetal resin, butyl rubber, chloroprene rubber, acrylonitrile-butadiene copolymer, acrylonitrile-butadiene-acrylic acid copolymer, acrylonitrile-butadiene-styrene copolymer, poly Examples include vinyl acetate. The thermoplastic resin may be a single polymer or two or more copolymers of the above thermoplastic resins.

The softening point of the thermoplastic resin is not particularly limited, but is preferably 10 ° C. or more lower than the melting point of the metal layer constituting the conductive connecting material, particularly preferably 20 ° C. or more, and more preferably 30 ° C. or more.

  The decomposition temperature of the thermoplastic resin is not particularly limited, but is preferably 10 ° C. or higher, particularly preferably 20 ° C. or higher, and more preferably 30 ° C. or higher than the melting point of the metal layer constituting the conductive connecting material. More preferred.

Content of a thermoplastic resin can be suitably set according to the form of the thermoplastic resin composition to be used.
For example, when the thermoplastic resin composition is liquid, the content of the thermoplastic resin is preferably 10% by weight or more, more preferably 15% by weight or more, and more preferably 20% by weight with respect to the total weight of the thermoplastic resin composition. The above is more preferable, 25% by weight or more is further more preferable, 30% by weight or more is still more preferable, and 35% by weight or more is particularly preferable. Moreover, 100 weight% or less is preferable, 95 weight% or less is more preferable, 90 weight% or less is more preferable, 75 weight% or less is still more preferable, 65 weight% or less is still more preferable, 55 weight% or less is especially preferable.
When the thermoplastic resin composition is solid, the content of the thermoplastic resin is preferably 5% by weight or more, more preferably 10% by weight or more, and more preferably 15% by weight with respect to the total weight of the thermoplastic resin composition. The above is more preferable, and 20% by weight or more is particularly preferable. Moreover, 90 weight% or less is preferable, 85 weight% or less is more preferable, 80 weight% or less is further more preferable, 75 weight% or less is still more preferable, 65 weight% or less is still more preferable, 55 weight% or less is especially preferable.
When the content of the thermoplastic resin is within the above range, the electrical connection strength between the terminals and the mechanical adhesive strength can be sufficiently secured.

(Ii) Other additives The compound having a flux function, the silane coupling agent, and other additives used in the thermoplastic resin composition of the present invention are the same as those described in the above “(a) Curable resin composition”. The same can be used. The content of each component, preferred compounds and preparation methods are also the same as those described for the curable resin composition.

  In the present invention, it is preferable to use a curable resin composition as the resin composition. Among them, the epoxy resin is 10 to 90% by weight, the curing agent is 0.1 to 50% by weight, the film-forming resin is 5 to 50% by weight, and the compound having a flux function is 1 to 50% by weight with respect to the total weight of the resin composition. More preferably, it contains The epoxy resin is 20 to 80% by weight, the curing agent is 0.2 to 40% by weight, the film-forming resin is 10 to 45% by weight, and the compound having a flux function is 2 to 40% by weight with respect to the total weight of the resin composition. More preferably, those containing The epoxy resin is 35 to 55% by weight, the curing agent is 0.5 to 30% by weight, the film-forming resin is 15 to 40% by weight, and the compound having a flux function is 3 to 25% by weight with respect to the total weight of the resin composition. Those containing are particularly preferred.

  In the conductive connection material of the present invention, the thickness of each resin composition layer is not particularly limited, but is preferably 1 μm or more, more preferably 3 μm or more, and particularly preferably 5 μm or more. Further, the thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, and particularly preferably 100 μm or less. When the thickness of the resin composition layer is within the above range, the gap between adjacent terminals can be sufficiently filled with the resin composition, and after the resin composition is cured, the mechanical adhesive strength after solidification and the opposite are opposed. A sufficient electrical connection between the terminals can be ensured, and the connection terminals can be manufactured.

When the conductive connection material of the present invention includes a plurality of resin composition layers, the composition of each resin composition layer may be the same, or may differ depending on the type of resin component used, the difference in formulation, and the like. The physical properties such as melt viscosity and softening temperature of the resin composition layer may be the same or different. For example, a liquid resin composition layer and a solid resin composition layer may be used in combination.

(2) Metal layer In this invention, a metal layer is a layer comprised by the alloy which has a tin as a main component, or the metal layer of tin. The metal layer should just be formed in at least one part of the resin composition layer by planar view, and may be formed in the whole surface of the resin composition layer.

  The shape of the metal layer is not particularly limited, and a certain shape may be repeatedly formed in a pattern shape, or the shape may be irregular. Regular shapes and irregular shapes may be mixed. FIG. 1 is a schematic plan view showing an example of the shape of the metal layer. Metal layers 110 having various shapes are formed on the resin composition layer 120. As the shape of the metal layer, for example, a dotted pattern (a), stripe pattern (b), polka dot pattern (c), rectangular pattern (d), checker pattern (as shown in FIG. e), frame shape (f), lattice pattern shape (g), or multiple frame shape (h). These shapes are examples, and these shapes can be combined or deformed depending on the purpose and application.

  In one embodiment of the present invention, when connecting a full grid type adherend in which the electrode to be connected is disposed on the entire connection surface of the adherend, a metal layer is formed on the entire surface of the resin composition. It is preferable to do.

  In addition, when connecting a peripheral type adherend in which the electrode to be connected is arranged in the periphery of the connection surface of the adherend, a viewpoint of effectively using the metal layer and between adjacent electrodes From the viewpoint of not leaving the metal layer, it is preferable to form a patterned metal layer repeatedly on at least a part of the resin composition. At this time, the shape of the metal layer can be appropriately selected depending on the pitch and form of the electrodes.

  The metal layer used in the present invention is not particularly limited, but tin (Sn), lead (Pb), silver (Ag), bismuth (Bi), indium (In), zinc (Zn), nickel (Ni), An alloy of at least two metals selected from the group consisting of antimony (Sb), iron (Fe), aluminum (Al), gold (Au), germanium (Ge), and copper (Cu), or a simple substance of tin It is preferable.

  Among these, considering the melting temperature and mechanical properties, the metal layer is composed of an Sn—Pb alloy, an Sn—Bi alloy that is a lead-free solder, an Sn—Ag—Cu alloy, an Sn—In alloy, Sn. An alloy containing Sn as a main component, such as an alloy of -Ag, is more preferable. When using an Sn—Pb alloy, the content of tin is preferably 30% by weight or more and less than 100% by weight, more preferably 35% by weight or more and less than 100% by weight, and particularly preferably 40% by weight or more. Moreover, less than 100 weight% is preferable. In the case of lead-free solder, the content of tin is preferably 15% by weight or more and less than 100% by weight, more preferably 20% by weight or more and less than 100% by weight, and particularly preferably 25% by weight or more and less than 100% by weight. For example, Sn 63-Pb (melting point 183 ° C.), Sn-3.0Ag-0.5Cu (melting point 217 ° C.), Sn-3.5Ag (melting point 221 ° C.), Sn-58 Bi (Melting point 139 ° C.), Sn-9.0Zn (melting point 199 ° C.), Sn-3.5Ag-0.5Bi-3.0In (melting point 193 ° C.), Au-20Sn (melting point 280 ° C.), etc. .

What is necessary is just to select a metal layer suitably according to the heat resistance of the electronic member and semiconductor device which are going to connect. For example, in the connection between terminals in a semiconductor device, the melting point is 330 ° C. or lower (more preferably 300 ° C. or lower, particularly preferably 280 ° C. or lower, more preferably, in order to prevent the members of the semiconductor device from being damaged by thermal history. It is preferable to use a metal layer that is 260 ° C. or lower. In order to ensure the heat resistance of the semiconductor device after the connection between terminals, the melting point is 100.
It is preferable to use a metal layer having a temperature of ℃ or higher (more preferably 110 ℃ or higher, particularly preferably 120 ℃ or higher). In addition, melting | fusing point of a metal layer can be measured with a differential scanning calorimeter (DSC).

  The thickness of the metal layer can be appropriately selected according to the gap between the opposing terminals, the separation distance between adjacent terminals, and the like. For example, in the case of connection between connection terminals such as a semiconductor chip, a substrate, and a semiconductor wafer in a semiconductor device, the thickness of the metal layer is preferably 0.5 μm or more, more preferably 1 μm or more, particularly preferably 5 μm or more, 100 micrometers or less are preferable, 50 micrometers or less are more preferable, and 20 micrometers or less are especially preferable. When the thickness of the metal layer is less than the lower limit, the number of unconnected terminals tends to increase due to an alloy containing tin as a main component or tin. It tends to cause a short circuit between the terminals.

  As a formation method of a metal layer, it can form on the whole surface on a support base material by a vacuum evaporation method or a vacuum sputtering method. In addition, as a method for producing a repetitive patterned metal layer, for example, after forming a metal layer on the entire surface of the support substrate by a vacuum sputtering method or a vacuum vapor deposition method, an unnecessary metal layer is etched to repeat the repetitive pattern shape. The metal layer can be formed. Furthermore, by using a shielding plate, a mask, or the like, it is possible to repeatedly form a patterned metal layer at a desired position of the support substrate by vacuum deposition or vacuum sputtering.

The support substrate is not particularly limited, and examples thereof include metal substrates such as copper, aluminum, and gold, resin substrates such as polyethylene, polypropylene, polyethylene terephthalate, polybutylene terephthalate, and fluororesin. Polyethylene, polypropylene, and fluororesin that are excellent in transferability from the supporting substrate are preferred.
Further, for the purpose of improving the transferability of the metal layer from the supporting substrate, the surface of the supporting substrate may be subjected to a mold release treatment with a fluorine resin, a silicon resin, or the like.

  The content of the metal layer is preferably 5% by weight or more, more preferably 20% by weight or more, and particularly preferably 30% by weight or more with respect to the total weight of the conductive connecting material. Moreover, less than 100 weight% is preferable, 80 weight% or less is more preferable, and 70 weight% or less is especially preferable. If the content of the metal layer is less than the above lower limit, there may be an increase in the number of unconnected terminals due to an alloy containing tin as a main component or tin shortage. On the other hand, when the content of the metal layer exceeds the above upper limit, it becomes easy to cause a bridge between adjacent terminals due to an alloy containing tin as a main component or an excess of tin.

  Or you may define content of a metal layer by the volume ratio with respect to a conductive connection material. For example, the content of the metal layer is preferably 1% by volume or more, more preferably 5% by volume or more, and particularly preferably 10% by volume or more with respect to the conductive connection material. Moreover, 90 volume% or less is preferable, 80 volume% or less is more preferable, and 70 volume% or less is especially preferable. If the content of the metal layer is less than the above lower limit, there may be an increase in the number of unconnected terminals due to an alloy containing tin as a main component or tin shortage. On the other hand, when the content of the metal layer exceeds the above upper limit, it becomes easy to cause a bridge between adjacent terminals due to an alloy containing tin as a main component or an excess of tin.

In the present invention, the form of the conductive connection material can be appropriately selected according to the form of the resin composition. For example, when the resin composition is in liquid form, the resin composition is applied onto a release substrate such as a polyester sheet, dried at a predetermined temperature for semi-curing (B-stage), etc. By transferring the metal layer formed on the supporting base material to the resin composition using a vapor deposition apparatus or a vacuum sputtering apparatus, it can be used as a conductive connection material. When the resin composition is solid, the resin composition varnish dissolved in an organic solvent is applied onto a release substrate such as a polyester sheet, dried at a predetermined temperature, and then applied to a vacuum deposition apparatus or a vacuum sputtering apparatus. Then, the metal layer formed on the supporting substrate can be transferred to the resin composition and used as a conductive connection material.

  The thickness of the conductive connecting material of the present invention is not particularly limited, but is preferably 1 μm or more, more preferably 3 μm or more, particularly preferably 5 μm or more, preferably 200 μm or less, more preferably 150 μm or less, and particularly preferably 100 μm or less. . When the thickness of the conductive connecting material is within the above range, the resin composition can be sufficiently filled in the gap between adjacent terminals. In addition, the mechanical adhesive strength after the resin component is cured or solidified and the electrical connection between the opposing terminals can be sufficiently ensured. In addition, it is possible to manufacture a connection terminal according to the purpose and application.

Next, a method for manufacturing the conductive connection material will be described.
When the resin composition used in the present invention is liquid at 25 ° C., for example, after applying the resin composition on a release substrate and drying and film-forming at a predetermined temperature for the purpose of semi-curing (B stage), The two-layer conductive connection material of the present invention can be produced by transferring a metal layer formed on a support substrate to a resin composition using a vacuum deposition apparatus or a vacuum sputtering apparatus.
When the resin composition is formed on both sides of the metal layer, a semi-cured resin composition is laminated on the opposite side of the metal layer of the two-layer conductive connecting material. What is necessary is just to manufacture by doing. When it is necessary to control the thickness of the resin composition, after applying the liquid resin composition on the peeling substrate, the method of passing a bar coater having a certain gap or the liquid resin composition by a spray coater or the like It can be produced by a method of spraying a predetermined amount on the peeling substrate.

  Moreover, when the resin composition used by this invention is solid at 25 degreeC, a conductive connection material can be manufactured as follows, for example. First, a varnish of a resin composition dissolved in an organic solvent is applied onto a peeling substrate such as a polyester sheet, dried at a predetermined temperature, and formed into a film to prepare a film-like resin composition. Next, the metal layer formed on the support substrate is transferred to the resin composition formed on the release substrate using a vacuum vapor deposition apparatus or a vacuum sputtering apparatus, and the surface of the metal layer having the resin composition is then transferred. From the resin composition / metal layer / resin composition in which the resin composition is arranged above and below the metal layer by laminating another prepared film-like resin composition with a hot roll on the opposite surface A three-layer conductive connection material can be produced.

When producing a conductive connection material with a patterned metal layer, a mask with an opening for forming the metal layer is placed on the support substrate, and the metal layer is formed into a pattern by vacuum evaporation or vacuum sputtering. can do. Other than using a mask, a metal layer is formed on the entire surface of the support substrate by vacuum deposition or sputtering, and then coated with a photosensitive resist used for circuit formation. After exposure and development, an unnecessary metal layer is formed. It is also possible to form a patterned metal layer by etching and removing the photosensitive resist. When the resin composition is provided on both sides of the patterned metal layer, the metal layer formed on the support substrate is transferred to the resin composition formed on the release substrate using a vacuum vapor deposition device or vacuum sputtering device. Further, a film-like resin composition may be further laminated on the surface opposite to the surface on which the resin composition of the patterned metal layer is formed.
In addition, the manufacturing method of a conductive connection material is not restrict | limited to the said method. The manufacturing method of the conductive connection material can be appropriately selected by those skilled in the art according to the purpose and application.

A commercially available vacuum sputtering apparatus can be used for the vacuum sputtering method, and the degree of vacuum is preferably 1 × 10 ⁻¹ to 1 × 10 ⁻⁵ Torr, particularly preferably 1 × 10 ⁻² to 1 × 10 ⁻⁴ Torr. . The discharge power can be 1000 to 2000 W, and argon or the like can be used as the inert gas.

In the vacuum deposition method, a commercially available vacuum deposition apparatus can be used, and the degree of vacuum is preferably 1 × 10 ⁻⁴ Torr or less, particularly preferably 1 × 10 ⁻⁵ Torr or less. Further, the acceleration voltage is preferably 1 to 30 kv, and particularly preferably 2 to 25 kv.

2. Next, a connection method between terminals according to the present invention will be described.
The connection method of the present invention relates to a method of connecting terminals using the conductive connection material manufactured by the method of manufacturing the conductive connection material, and an arrangement step of arranging the conductive connection material between opposing terminals; A heating step of heating the conductive connecting material; and a curing / solidifying step of curing or solidifying the resin composition. The connection method of the present invention can be used, for example, when connecting terminals formed on a semiconductor wafer, a semiconductor chip, a rigid substrate, a flexible substrate, and other electrical and electronic components.

  In the connection method of the present invention, the steps of the connection method are slightly different depending on whether the resin composition of the conductive connection material is a curable resin composition or a thermoplastic resin composition. Hereinafter, the case where the resin composition of the conductive connecting material is a curable resin composition will be described as a first embodiment, and the case where it is a thermoplastic resin composition will be described as a second embodiment.

(1) 1st embodiment The connection method between the terminals of the 1st embodiment of this invention WHEREIN: The arrangement | positioning process which arrange | positions the electrically-conductive connection material containing the said curable resin composition and a metal layer between the opposing terminals, It includes a heating step of heating the conductive connecting material at a temperature that is equal to or higher than the melting point of the metal layer and the curing of the curable resin composition is not completed, and a curing step of curing the curable resin composition.

  In this connection method, an alloy mainly composed of heat-melted tin or tin is selectively aggregated between terminals to form a conductive region, and an insulating region is formed around the curable resin composition. Can do. As a result, insulation between adjacent terminals can be ensured and leakage current can be prevented, so that connection reliability of connection between terminals can be improved. In addition, even in a fine wiring circuit, electrical connection between a large number of terminals can be performed collectively. Furthermore, the mechanical strength of the conductive region or the insulating region can be increased by curing the curable resin composition.

Hereinafter, preferred embodiments of the connection method between terminals of the first embodiment of the present invention will be described in detail with reference to the drawings, but the connection method of the present invention is not limited to these drawings.
(A) Arrangement Step First, as shown in FIG. 2, the substrate 10 provided with the terminal 11 and the substrate 20 provided with the terminal 21 are aligned so that the terminal 11 and the terminal 21 face each other. The conductive connection material 30 composed of the metal layer 110 and the curable resin composition 120 provided on both surfaces of the metal layer 110 is disposed between the terminals. At this time, the conductive connecting material 30 is thermocompression bonded to one side of the substrate 10 or the substrate 20 or both of the substrate 10 and the substrate 20 as shown in FIG. 4 using an apparatus such as a roll laminator or a press. Also good. Further, the surfaces of the terminals 11 and 21 may be subjected to treatments such as cleaning, polishing, plating, and surface activation as necessary in order to improve electrical connection.

(B) Heating step In the heating step, the conductive connecting material arranged between the terminals in the arranging step is heated at a temperature equal to or higher than the melting point of the metal layer. The heating temperature should just be more than melting | fusing point of a metal layer, for example, the range which can move the alloy or tin which has tin as a main component, or tin in a curable resin by adjusting heating time, such as shortening heating time, ie, " The upper limit is not particularly limited as long as the curing of the curable resin composition is not completed. The heating temperature is preferably 5 ° C. or more higher than the melting point of the metal layer, more preferably 10 ° C. or more, more preferably 20 ° C. or more, and particularly preferably 30 ° C. or more.

  The heating temperature can be appropriately selected depending on the metal layer to be used and the composition of the curable resin composition, but is preferably 100 ° C or higher, more preferably 130 ° C or higher, particularly preferably 140 ° C or higher, and 150 ° C or higher. Most preferred. In order to prevent thermal degradation of the substrate or the like to be connected, the heating temperature is preferably 260 ° C. or lower, more preferably 250 ° C. or lower, and particularly preferably 240 ° C. or lower.

  When the conductive connecting material is heated at such a temperature, the metal layer 110 is melted, and the alloy or tin mainly containing molten tin can move in the curable resin composition 120. When the curable resin composition contains a compound having a flux function, the tin-based alloy or the surface oxide film of tin is removed by the reducing action of the compound having the flux function contained in the curable resin composition. Therefore, an alloy containing tin as a main component or tin is in a state in which wettability is enhanced, and metal bonding is promoted to easily aggregate between opposing terminals. On the other hand, since the surface oxide films of the terminals 11 and 21 are also removed by the reducing action of the compound having a flux function and the wettability is enhanced, the metal bond with the tin-based alloy or tin is facilitated. As a result, as shown in FIG. 3, a conductive region 130 is formed between the terminals, and the terminals 11 and 21 are electrically connected. On the other hand, the insulating region 140 is formed by filling the periphery of the conductive region with the curable resin composition. As a result, insulation between adjacent terminals is ensured, and a short circuit between adjacent terminals can be prevented.

In the connection method of the present invention, heating may be performed by applying pressure so as to reduce the distance between the opposing terminals. For example, the distance between the terminals facing each other can be controlled to be constant by heating and pressurizing using means such as a known thermocompression bonding apparatus in the direction in which the substrates 10 and 20 in FIG. 2 face each other. It is possible to increase the reliability of electrical connection between the terminals to be performed.
Furthermore, when heating or heating, an ultrasonic wave or an electric field may be applied, or special heating such as laser or electromagnetic induction may be applied.

(C) Curing Step In the connection method of the present invention, after forming the conductive region 130 and the insulating region 140 in the heating step, the curable resin composition is cured and the insulating region 140 is fixed. Thereby, electrical reliability and mechanical connection strength between the terminals can be sufficiently ensured. In particular, in the connection method of the present invention, since a curable resin composition having a high insulation resistance value is used, the insulation of the insulating region can be more sufficiently ensured.

  Curing of the curable resin composition can be performed by heating the conductive connecting material. The curing temperature of the conductive connecting material can be appropriately set according to the composition of the curable resin composition, but is preferably at least 5 ° C. lower than the heating temperature in the heating step, and at least 10 ° C. lower temperature. It is particularly preferred that Specifically, it is preferably 100 ° C. or higher, more preferably 120 ° C. or higher, particularly preferably 130 ° C. or higher, and most preferably 150 ° C. or higher. Further, it is preferably 300 ° C. or lower, more preferably 260 ° C. or lower, particularly preferably 250 ° C. or lower, and most preferably 240 ° C. or lower. When the curing temperature is within the above range, the conductive connecting material is not thermally decomposed, and the curable resin composition can be sufficiently cured.

(2) Second Embodiment Next, a method for connecting terminals according to a second embodiment of the present invention will be described. The connection method between the terminals of the second embodiment of the present invention is an arrangement step of disposing a conductive connection material including the thermoplastic resin composition and a metal layer between opposing terminals, and a melting point of the metal layer or higher. And a heating step of heating the conductive connecting material at a temperature at which the thermoplastic resin composition is softened, and a solidification step of solidifying the thermoplastic resin composition. Hereinafter, each step will be described.

(A) Arrangement process Even when a conductive connection material including a thermoplastic resin composition and a metal layer is used, the conductive connection is performed in the same manner as when a conductive connection material including the thermosetting resin composition and a metal layer is used. Material can be placed.

(B) Heating step Although the heating step is not particularly limited, the conductive connecting material arranged between the terminals in the arrangement step is heated at a temperature equal to or higher than the melting point of the metal layer. The heating temperature is preferably 5 ° C. or more higher than the melting point of the metal layer, more preferably 10 ° C. or more, more preferably 20 ° C. or more, and particularly preferably 30 ° C. or more. The heating temperature is equal to or higher than the melting point of the metal layer, and the thermoplastic resin composition is softened so that the alloy containing tin as a main component or tin can move in the thermoplastic resin, that is, “the thermoplastic resin composition is softened”. If it is a range, the upper limit in particular will not be restrict | limited.

  The heating temperature can be appropriately selected depending on the metal layer to be used and the composition of the thermoplastic resin composition. For example, it can be heated at the same heating temperature as the conductive connecting material containing the curable resin composition and the metal layer.

  When the conductive connecting material is heated at the above temperature, the metal layer 110 is melted, and the molten tin-based alloy or tin can move through the thermoplastic resin composition 120. When the thermoplastic resin composition contains a compound having a flux function, the tin-based alloy or the surface oxide film of tin is removed by the reducing action of the compound having the flux function contained in the thermoplastic resin composition. Therefore, an alloy containing tin as a main component or tin is in a state in which wettability is enhanced, and metal bonding is promoted to easily aggregate between opposing terminals. On the other hand, since the surface oxide films of the terminals 11 and 21 are also removed by the reducing action of the compound having a flux function and the wettability is enhanced, the metal bond with the tin-based alloy or tin is facilitated. As a result, as shown in FIG. 3, a conductive region 130 is formed between the terminals, and the terminals 11 and 21 are electrically connected. On the other hand, the insulating region 140 is formed by filling the periphery of the conductive region with the thermoplastic resin composition. As a result, insulation between adjacent terminals is ensured, and a short circuit between adjacent terminals can be prevented.

(C) Solidification step In the connection method of the present invention, after forming the conductive region 130 and the insulating region 140 in the heating step, the thermoplastic resin composition is solidified to fix the insulating region 140 region. Thereby, electrical reliability and mechanical connection strength between the terminals can be sufficiently ensured.

  Solidification of the thermoplastic resin composition can be carried out by cooling and solidifying the conductive connecting material heated and melted in the heating step. Cooling and solidification of the conductive connecting material can be appropriately set according to the composition of the thermoplastic resin composition, and is not particularly limited, but may be a method by natural cooling, or a method such as blowing cold air But you can.

The solidification temperature of the thermoplastic resin composition is not particularly limited, but is preferably lower than the melting point of the metal layer. More specifically, the solidification temperature of the thermoplastic resin composition is preferably 10 ° C. or more lower than the melting point of the metal layer, and particularly preferably 20 ° C. or lower. The solidification temperature of the thermoplastic resin composition is preferably 50 ° C. or higher, particularly preferably 60 ° C. or higher, and further preferably 100 ° C. or higher. When the solidification temperature of the thermoplastic resin composition is within the above range, the conductive region 130 can be reliably formed,
The insulating region 140 can have a desired heat resistance. For this reason, the insulation between adjacent terminals is ensured, and a short circuit between adjacent terminals can be more reliably prevented.

  According to a preferred embodiment of the present invention, an alloy or tin based on tin is selected by using a conductive connecting material comprising a resin composition containing a specific resin component and a compound having a flux function and a metal layer. Therefore, the terminals can be aggregated between the terminals facing each other, the terminals can be electrically connected, and insulation between adjacent terminals can be ensured. Furthermore, it is possible to conduct a large number of terminals in a lump, and it is possible to implement a connection between terminals with excellent reliability.

3. Next, a method for manufacturing a connection terminal according to the present invention will be described.
The manufacturing method of the connection terminal of the present invention is related to a method of manufacturing the connection terminal on the electrode of the electronic member using the conductive connection material, and an arrangement step of arranging the conductive connection material on the electrode of the electronic member; And a heating step of heating the conductive connecting material and a curing / solidifying step of curing or solidifying the resin composition. The method for manufacturing a connection terminal of the present invention can be used, for example, when manufacturing a connection terminal on an electrode of a semiconductor wafer, a semiconductor chip, a rigid substrate, a flexible substrate, or other electrical and electronic components.

  In the method for producing a connection terminal of the present invention, the production process of the connection terminal is slightly different depending on whether the resin composition of the conductive connection material is a curable resin composition or a thermoplastic resin composition. Hereinafter, the case where the resin composition of the conductive connecting material is a curable resin composition will be described as a third embodiment, and the case where the resin composition is a thermoplastic resin composition will be described as a fourth embodiment.

(1) 1st embodiment The manufacturing method of the connection terminal of the 1st embodiment of the present invention arranges the conductive connection material containing the curable resin composition and the metal layer on the electrode of the electronic member, A heating step of heating the conductive connecting material at a temperature that is equal to or higher than the melting point of the metal layer and the curing of the curable resin composition is not completed, and a curing step of curing the curable resin composition. .
In this connection terminal manufacturing method, an alloy mainly composed of heat-melted tin or tin is selectively agglomerated on an electrode on a substrate to form a connection terminal, and an insulating region formed by a curable resin composition around the connection terminal. Can be formed. As a result, since the periphery of the connection terminal can be covered with the curable resin composition, the conductive region is fixed. Moreover, since the insulation between adjacent connection terminals is ensured by the insulating region, the connection reliability can be improved. According to this method, a large number of connection terminals can be manufactured at once even in a fine wiring circuit.

  Hereinafter, the manufacturing method of the connection terminal according to the first embodiment of the present invention will be described in more detail with reference to the drawings. However, the connection method of the present invention is not limited to these drawings.

(A) Arrangement Step First, as shown in FIG. 5, a conductive connection material having a curable resin composition 120 and a metal layer 110 is arranged on a substrate 40 on which an electrode 41 is provided. At this time, when a patterned metal layer is used, it is necessary to align the conductive connection material 50 and the electrode 41 on the substrate. In FIG. 5, the curable resin composition 120 formed on one side of the metal layer 110 is used. However, the curable resin composition 120 may be formed on both sides of the metal layer 110. . Moreover, in FIG. 5, although the curable resin composition 120 is arrange | positioned so that a connection terminal may be opposed, you may arrange | position so that the metal layer 110 may oppose a connection terminal.
As shown in FIG. 6, the conductive connection material 50 may be thermocompression bonded to the substrate 40 using an apparatus such as a roll laminator or a press. In FIG. 6, the curable resin composition 120 covers the electrode 41, but the thermosetting resin composition 120 may be thinner than the electrode 41 or thicker than the electrode 41. It can be appropriately adjusted according to the purpose and application. Further, the surface of the electrode 41 is subjected to treatments such as cleaning, polishing, plating, and surface activation as necessary in order to improve electrical connection or to improve the bondability with the metal layer. May be applied.

(B) Heating step In the heating step, the conductive connecting material 50 placed on the electrode 41 on the substrate 40 in the placement step is not lower than the melting point of the metal layer, and the curing of the curable resin composition is not completed. Heat at temperature. Thereby, the connection terminal 150 can be formed on the electrode 41 as shown in FIG. On the other hand, a curable resin composition is filled around the connection terminal 150 to form an insulating region 140. As a result, insulation between the adjacent connection terminals 150 is ensured, and a short circuit between the adjacent connection terminals 150 can be prevented.

  The heating temperature and the pressurizing condition of the curable resin composition can be performed under the same conditions as when the connection between terminals is performed using the conductive connection material having the curable resin composition and the metal layer. .

(C) Curing Step In the curing step, after forming the connection terminal 150 and the insulating region 140 in the heating step, the curable resin composition is cured and the insulating region 140 is fixed. Thereby, joining of the electrode 41 and the connection terminal 150 on a board | substrate can be reinforced. In particular, in the first embodiment of the present invention, since the curable resin composition having a high insulation resistance value is used, the insulation of the insulating region can be more sufficiently ensured. Although not particularly limited, this curing step is preferably performed after the connection terminal 150 is formed and then the substrate 60 is mounted and connected to another electrical or electronic component or substrate.
The heating temperature of the conductive connection material in the curing step can be performed under the same conditions as in the case where the connection between terminals is performed using the conductive connection material having the curable resin composition and the metal layer.

(2) Second Embodiment Next, a method for manufacturing a connection terminal according to a second embodiment of the present invention will be described.
The manufacturing method of the connection terminal of the second embodiment of the present invention includes an arrangement step of disposing a conductive connection material including the thermoplastic resin composition and a metal layer on an electrode of an electronic member, and a melting point of the metal layer or higher. And a heating step of heating the conductive connecting material at a temperature at which the thermoplastic resin composition is softened, and a solidification step of solidifying the thermoplastic resin composition as necessary.
In the manufacturing method of the second embodiment, an alloy mainly composed of heat-melted tin or tin is selectively agglomerated on an electrode on a substrate to form a connection terminal, and an insulating property by a thermoplastic resin composition is formed around the connection terminal. Regions can be formed. As a result, since the periphery of the connection terminal can be covered with the thermoplastic resin composition, the conductive region is fixed. Moreover, since the insulation between adjacent connection terminals is ensured by the insulating region, the connection reliability can be improved. According to this method, a large number of connection terminals can be manufactured at once even in a fine wiring circuit.

(A) Arrangement step When a conductive connection material including a thermoplastic resin composition and a metal layer is used, a conductive connection material including the thermosetting resin composition of the first embodiment and a metal layer is used. Similarly to the above, the conductive connecting material can be disposed on the substrate provided with the electrodes.

(B) Heating step In the heating step, the conductive connecting material 50 arranged on the electrode provided on the substrate in the arranging step is at a temperature equal to or higher than the melting point of the metal layer and the thermoplastic resin composition is softened. Heat. Thereby, a connection terminal can be manufactured on an electrode similarly to the 1st embodiment.
On the other hand, a thermoplastic resin composition is filled around the connection terminal to form an insulating region. As a result, insulation between adjacent connection terminals is ensured, and a short circuit between adjacent connection terminals can be prevented.

  In addition, the heating temperature and pressurizing conditions of the thermoplastic resin composition should be the same as the case where the connection between terminals is performed using the conductive connection material having the thermoplastic resin composition and the metal layer. Can do.

(C) Solidification step In the solidification step, after forming the connection terminal and the insulating region in the heating step, the thermoplastic resin composition is cooled and solidified, and the insulating region is fixed. Can be reinforced.
In addition, about the cooling method and preferable solidification temperature of a thermoplastic resin composition, it is the same as that of the case where the connection between terminals is performed using the conductive connection material which has the said thermoplastic resin composition and a metal layer.

  As described above, in the present invention, by using the conductive connection material of the present invention, an alloy containing tin as a main component or tin can be selectively agglomerated at the connection terminal formation site, so that the connection terminal can be simply formed. Can be manufactured. According to the method for manufacturing a connection terminal of the present invention, not only can a plurality of connection terminals be manufactured at once, but also an insulating region can be formed around the connection terminal. It is possible to ensure insulation between connecting terminals. Thereby, the connection terminal excellent in connection reliability can be manufactured.

4). TECHNICAL FIELD The present invention also includes an electronic member with a conductive connection material formed by adhering the conductive connection material of the present invention to an electrical connection surface of an electronic member. In the electronic member with a conductive connection material of the present invention, the adhesive surface of the conductive connection material with the electrical connection surface of the electronic member is preferably a resin composition layer. The resin composition layer may be directly bonded to the electrical connection surface of the electronic member, or may be bonded via an adhesive layer. The electronic members with the conductive connection material of the present invention are bonded to each other, or the electronic members with the conductive connection material of the present invention are bonded to the electrical connection surfaces of the other electronic members and thermocompression bonded so that the electronic members are electrically connected. Can be connected.
In the present invention, a semiconductor wafer, a semiconductor chip, a rigid substrate, a flexible substrate, and other electrical and electronic components in which electronic members are electrically connected using the conductive connection material of the present invention thus obtained are provided. Is also included.

  The conductive connecting material obtained by laminating the resin composition layer and the metal layer obtained by the manufacturing method of the present invention can be used to electrically connect electronic members between electrical and electronic components, or to manufacture connection terminals on a substrate. Can be suitably used. By using the conductive connection material according to the present invention, it is possible to achieve both good electrical connection between electronic members and high insulation reliability. By using the conductive connection material according to the present invention, connection between terminals in a fine wiring circuit is also possible. By using the conductive connection material according to the present invention, it is possible to meet the demand for higher functionality and downsizing of electronic devices.

10, 20 Substrate 11, 21 Terminal 30 Conductive connecting material 40 Substrate 41 Electrode 50 Conductive connecting material 60 Substrate 110 Metal layer 120 Resin composition 130 Conductive region 140 Insulating region 150 Connecting terminal

Claims (10)

A metal layer forming step of forming an alloy containing tin as a main component or a metal layer of tin on a supporting substrate by a vacuum sputtering method or a vacuum evaporation method;
A first resin composition layer forming step of forming a first resin composition layer containing a resin component;
A metal layer transfer step of laminating the first resin composition and the metal layer by transferring the metal layer from the support substrate to at least one surface of the first resin composition layer;
A second resin composition forming step of forming a second resin composition layer containing a resin component on the surface of the metal layer opposite to the surface in contact with the first resin composition layer;
A method for producing a conductive connecting material comprising:
The first resin composition layer and the second resin composition layer are composed of a resin composition containing the resin component and a compound having a flux function,
The method for producing a conductive connecting material, wherein the thickness of the metal layer is 5 μm or more and 100 μm or less . The metal layer includes tin (Sn), lead (Pb), silver (Ag), bismuth (Bi), indium (In), zinc (Zn), nickel (Ni), antimony (Sb), iron (Fe), The conductive connection according to claim 1 , wherein the conductive connection is an alloy of at least two kinds of metals selected from the group consisting of aluminum (Al), gold (Au), germanium (Ge), and copper (Cu), and a simple substance of tin or indium. Material manufacturing method. The metal layer, Sn-Pb alloy, Sn-Ag-Cu method for producing an alloy or a conductive connecting material according to claim 1 or 2 configured to Sn-Ag alloy as a main material. The metal layer, Sn-37Pb alloy or Sn-3.0Ag-0.5Cu alloy manufacturing method of the conductive connecting material according to any of constituted claims 1 to 3 as a main material. The compound having a flux function, manufacturing method of a phenolic hydroxyl group and a conductive connecting material according to any one of claims 1 to 4 containing a compound having at least one of the carboxyl groups. The method for producing a conductive connecting material according to any one of claims 1 to 5, wherein the compound having a flux function contains a compound represented by the following general formula (1).
_{HOOC- (CH 2) n -COOH ·····} (1)
(In Formula (1), n is an integer of 1-20.) The method for producing a conductive connecting material according to any one of claims 1 to 5, wherein the compound having a flux function contains at least one of compounds represented by the following general formula (2) and the following general formula (3). .

[Wherein, R ^{1 to} R ⁵ are each independently a monovalent organic group, and at least one of R ^{1 to} R ⁵ is a hydroxyl group. ]

[Wherein, R ^{6 to} R ²⁰ are each independently a monovalent organic group, and at least one of R ^{6 to} R ²⁰ is a hydroxyl group or a carboxyl group. ] In the said resin composition, content of the compound which has the said flux function is 1 to 50 weight%, The manufacturing method of the electrically-conductive connection material in any one of Claim 1 thru | or 7 . Terminals facing each other is, that it is electrically connected via a connecting portion which is formed using a conductive connecting material produced by the production method of the conductive connecting material according to any one of claims 1 to 8 A featured semiconductor device. Terminals facing each other is, that it is electrically connected via a connecting portion which is formed using a conductive connecting material produced by the production method of the conductive connecting material according to any one of claims 1 to 8 Features electronic equipment.