WO2011024719A1 - 異方性導電材料、接続構造体及び接続構造体の製造方法 - Google Patents

異方性導電材料、接続構造体及び接続構造体の製造方法 Download PDF

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WO2011024719A1
WO2011024719A1 PCT/JP2010/064077 JP2010064077W WO2011024719A1 WO 2011024719 A1 WO2011024719 A1 WO 2011024719A1 JP 2010064077 W JP2010064077 W JP 2010064077W WO 2011024719 A1 WO2011024719 A1 WO 2011024719A1
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anisotropic conductive
conductive material
compound
group
weight
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PCT/JP2010/064077
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English (en)
French (fr)
Japanese (ja)
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茂雄 真原
敬士 久保田
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積水化学工業株式会社
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Priority to CN201080037248.5A priority Critical patent/CN102484326B/zh
Priority to JP2011528764A priority patent/JP5602743B2/ja
Publication of WO2011024719A1 publication Critical patent/WO2011024719A1/ja

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    • H—ELECTRICITY
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    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R11/00—Individual connecting elements providing two or more spaced connecting locations for conductive members which are, or may be, thereby interconnected, e.g. end pieces for wires or cables supported by the wire or cable and having means for facilitating electrical connection to some other wire, terminal, or conductive member, blocks of binding posts
    • H01R11/01—Individual connecting elements providing two or more spaced connecting locations for conductive members which are, or may be, thereby interconnected, e.g. end pieces for wires or cables supported by the wire or cable and having means for facilitating electrical connection to some other wire, terminal, or conductive member, blocks of binding posts characterised by the form or arrangement of the conductive interconnection between the connecting locations
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    • H01R12/00—Structural associations of a plurality of mutually-insulated electrical connecting elements, specially adapted for printed circuits, e.g. printed circuit boards [PCB], flat or ribbon cables, or like generally planar structures, e.g. terminal strips, terminal blocks; Coupling devices specially adapted for printed circuits, flat or ribbon cables, or like generally planar structures; Terminals specially adapted for contact with, or insertion into, printed circuits, flat or ribbon cables, or like generally planar structures
    • H01R12/50—Fixed connections
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    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
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Definitions

  • the present invention is an anisotropic conductive material including a plurality of conductive particles, and can be used for electrical connection between electrodes of various connection target members such as a flexible printed circuit board, a glass substrate, and a semiconductor chip.
  • the present invention relates to an anisotropic conductive material, a connection structure using the anisotropic conductive material, and a method of manufacturing the connection structure.
  • Anisotropic conductive materials such as anisotropic conductive paste, anisotropic conductive ink and anisotropic conductive adhesive are widely known.
  • anisotropic conductive materials a plurality of conductive particles are dispersed in paste, ink, or resin.
  • the anisotropic conductive material is, for example, a connection between a flexible printed circuit board and a glass substrate (FOG (Film on Glass)), a connection between a semiconductor chip and a flexible printed circuit board (COF (Chip on Film)), or a semiconductor chip. Used for connection to glass substrates (COG (Chip on Glass)) and the like.
  • Patent Document 1 As an example of the anisotropic conductive material, Patent Document 1 below includes an epoxy resin, rubber-like polymer particles, a thermally active latent epoxy curing agent, high softening point polymer particles, and conductive particles. An anisotropic conductive material is disclosed.
  • Patent Document 2 describes anisotropy satisfying the following formulas (A) and (B) when the viscosity at 25 ° C. and 2.5 pm is ⁇ 1, and the viscosity at 25 ° C. and 20 rpm is ⁇ 2.
  • a conductive adhesive is disclosed. 50 Pa ⁇ s ⁇ ⁇ 2 ⁇ 200 Pa ⁇ s Formula (A) 1.5 ⁇ ⁇ 1 / ⁇ 2 ⁇ 4.3 Formula (B)
  • an anisotropic conductive material containing conductive particles is disposed on the glass substrate.
  • the semiconductor chips are stacked, and heated and pressurized.
  • the anisotropic conductive material is cured, and the electrodes are electrically connected via the conductive particles to obtain a connection structure.
  • the anisotropic conductive material applied on the glass substrate at the time of electrical connection between the electrodes and the anisotropic conductive material In some cases, the conductive particles contained in the fluid flow largely before curing. For this reason, the hardened
  • An object of the present invention is an anisotropic conductive material containing conductive particles, which can increase conduction reliability when used for electrical connection between electrodes, and the It is to provide a connection structure using an anisotropic conductive material and a method for manufacturing the connection structure.
  • the composition contains a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles, and the content of the conductive particles is within a range of 1 to 19% by weight.
  • An anisotropic conductive material is provided.
  • the curable compound includes an episulfide compound.
  • the curable compound includes a curable compound having at least one of an epoxy group and a thiirane group and a (meth) acryloyl group. .
  • the viscosity of the anisotropic conductive material according to the present invention at 25 ° C. and 2.5 rpm is preferably in the range of 20 to 200 Pa ⁇ s.
  • the viscosity after being cured by light irradiation and converted into a B stage is in the range of 2000 to 3500 Pa ⁇ s.
  • the ⁇ 2 is 20 Pa ⁇ s or more and 200 Pa ⁇ s or less.
  • the ratio ( ⁇ 1 / ⁇ 2) of ⁇ 1 to ⁇ 2 is preferably 0.9 or more and 1.1 or less.
  • the curable compound includes a crystalline compound.
  • a connection structure includes a first connection target member, a second connection target member, and a connection portion that electrically connects the first and second connection target members, and The connecting portion is formed by curing an anisotropic conductive material configured according to the present invention.
  • an anisotropic conductive material is applied to the upper surface of the first connection target member to form an anisotropic conductive material layer, and light is applied to the anisotropic conductive material layer.
  • anisotropic conductive material a curable compound, a thermosetting agent, and photocuring
  • the anisotropic conductive material according to the present invention contains a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles
  • the anisotropic conductive material can be cured by light irradiation and heating. It can.
  • the anisotropic conductive material can be cured by thermosetting or photocuring.
  • the anisotropic conductive material and the conductive particles contained in the anisotropic conductive material can be flowed by irradiating the anisotropic conductive material with light or applying heat to the anisotropic conductive material at an appropriate time after coating. Can be suppressed. Therefore, the hardened
  • the anisotropic conductive material according to the present invention contains a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles, and the content of the conductive particles is in the range of 1 to 19% by weight. Since it is inside, when it is used for the electrical connection between electrodes, conduction
  • the anisotropic conductive material layer is cured by irradiating light to the anisotropic conductive material layer so that the viscosity is in the range of 2000 to 3500 Pa ⁇ s.
  • the anisotropic conductive material layer is B-staged so that the flow of the anisotropic conductive material layer and the conductive particles contained in the anisotropic conductive material layer can be suppressed. Therefore, the hardened
  • FIG. 1 is a partially cutaway front sectional view schematically showing a connection structure using an anisotropic conductive material according to an embodiment of the present invention.
  • 2 (a) to 2 (c) are partially cutaway front cross-sectional views for explaining each step of a method for manufacturing a connection structure using an anisotropic conductive material according to an embodiment of the present invention.
  • 3 (a) and 3 (b) show a method for manufacturing a connection structure using an anisotropic conductive material according to an embodiment of the present invention, using a composite device including a dispenser and a light irradiation device. It is a typical front view for demonstrating the method of forming the staged anisotropic conductive material layer.
  • FIGS. 4A and 4B are schematic front views for explaining a modification of the method of forming the B-staged anisotropic conductive material layer.
  • the anisotropic conductive material according to the present invention contains a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles.
  • the content of the conductive particles is in the range of 1 to 19% by weight.
  • the curable compound is not particularly limited.
  • a conventionally known curable compound can be used.
  • hardenable compound only 1 type may be used and 2 or more types may be used together.
  • the curable compound examples include light and thermosetting compounds, photocurable compounds, and thermosetting compounds.
  • the light and thermosetting compounds have photocuring properties and thermosetting properties.
  • the said photocurable compound has photocurability, for example, and does not have thermosetting.
  • the said thermosetting compound does not have photocurability, for example, and has thermosetting.
  • the curable compound includes light and a thermosetting compound, or includes a photocurable compound and a thermosetting compound.
  • the curable compound may not include at least one of the photocurable compound and the thermosetting compound.
  • at least one of a photocurable compound and a thermosetting compound may be further included.
  • the said curable compound does not contain the said light and a thermosetting compound, the said curable compound contains a photocurable compound and a thermosetting compound.
  • the curable compound includes the light and the thermosetting compound, and at least one of the photocurable compound and the thermosetting compound, Or it is preferable that a photocurable compound and a thermosetting compound are included. More preferably, the curable compound includes a photocurable compound and a thermosetting compound.
  • the curable compound is not particularly limited.
  • examples of the curable compound include epoxy compounds, episulfide compounds, (meth) acrylic compounds, phenolic compounds, amino compounds, unsaturated polyester compounds, polyurethane compounds, silicone compounds, and polyimide compounds.
  • the (meth) acryl means acryl or methacryl.
  • the anisotropic conductive material according to the present invention preferably contains the photocurable compound and the thermosetting compound in a weight ratio of 1:99 to 90:10, preferably 5:95 to 60:40. More preferably, it is more preferably included at 20:80 to 40:60.
  • the curable compound preferably contains a crystalline resin.
  • the crystalline resin is not particularly limited as long as it has crystallinity.
  • Examples of the crystalline resin include a resin having the light and thermosetting functional groups in the naphthalene skeleton structure, and a resin having the light and thermosetting functional groups in the resorcin skeleton structure.
  • a preferable lower limit of the content of the crystalline resin in 100 parts by weight of the curable compound is 80 parts by weight, and a more preferable lower limit. Is 90 parts by weight.
  • the curable compound is an epoxy compound or an episulfide compound (thiirane group-containing compound). It is preferable that at least one of these is included, and it is more preferable that an episulfide compound is included.
  • the preferred lower limit of the content of the episulfide compound is 10 parts by weight, the more preferred lower limit is 20 parts by weight, and the preferred upper limit is 50 parts by weight. Parts, more preferred upper limit is 40 parts by weight.
  • Each of the epoxy compound and the episulfide compound preferably has an aromatic ring.
  • the aromatic ring include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, tetracene ring, chrysene ring, triphenylene ring, tetraphen ring, pyrene ring, pentacene ring, picene ring and perylene ring.
  • the said aromatic ring is a benzene ring, a naphthalene ring, or an anthracene ring, and it is more preferable that it is a benzene ring or a naphthalene ring.
  • the episulfide compound has a thiirane group instead of an epoxy group, it can be quickly cured at a low temperature. That is, the episulfide compound having a thiirane group can be cured at a lower temperature derived from the thiirane group as compared with the epoxy compound having an epoxy group.
  • the episulfide compound preferably has a structure represented by the following formula (1), (2), (5), (7) or (8). It is more preferable to have a structure represented by the formula (1) or (2).
  • R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms
  • 2 to 4 groups out of 4 groups of R3, R4, R5 and R6 represent hydrogen
  • R3 , R4, R5 and R6 which are not hydrogen represent a group represented by the following formula (3).
  • All of the four groups R3, R4, R5 and R6 in the above formula (1) may be hydrogen.
  • One or two of the four groups of R3, R4, R5 and R6 are groups represented by the following formula (3), and among the four groups of R3, R4, R5 and R6
  • the group that is not a group represented by the following formula (3) may be hydrogen.
  • R7 represents an alkylene group having 1 to 5 carbon atoms.
  • R51 and R52 each represents an alkylene group having 1 to 5 carbon atoms, and 4 to 6 groups out of 6 groups of R53, R54, R55, R56, R57 and R58 are hydrogen.
  • the group which is not hydrogen among R53, R54, R55, R56, R57 and R58 represents a group represented by the following formula (4).
  • All of the six groups of R53, R54, R55, R56, R57 and R58 in the above formula (2) may be hydrogen.
  • One or two of the six groups of R53, R54, R55, R56, R57 and R58 are groups represented by the following formula (4), and R53, R54, R55, R56, R57 and R58. Of these, the group that is not a group represented by the following formula (4) may be hydrogen.
  • R59 represents an alkylene group having 1 to 5 carbon atoms.
  • R101 and R102 each represent an alkylene group having 1 to 5 carbon atoms.
  • Six to eight groups out of the eight groups R103, R104, R105, R106, R107, R108, R109 and R110 represent hydrogen.
  • the non-hydrogen group in R103, R104, R105, R106, R107, R108, R109, and R110 in the above formula (5) represents a group represented by the following formula (6). All of the eight groups of R103, R104, R105, R106, R107, R108, R109 and R110 may be hydrogen. One or two of the eight groups of R103, R104, R105, R106, R107, R108, R109 and R110 are groups represented by the following formula (6), and R103, R104, R105, R106 , R107, R108, R109 and R110, which is not a group represented by the following formula (6), may be hydrogen.
  • R111 represents an alkylene group having 1 to 5 carbon atoms.
  • R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms.
  • R3 and R4 each represent an alkylene group having 1 to 5 carbon atoms.
  • the episulfide compound having a structure represented by the above formula (1) or (2) has at least two thiirane groups (episulfide groups).
  • a group having a thiirane group is bonded to a benzene ring or a naphthalene ring. Since it has such a structure, the anisotropic conductive material can be rapidly cured at a low temperature by heating the anisotropic conductive material.
  • low temperature means a temperature of 200 ° C. or lower.
  • the episulfide compound having the structure represented by the above formula (1), (2), (5), (7) or (8) is represented by the above formula (1), (2), (5), (7) or The reactivity is high compared with the compound whose thiirane group in (8) is an epoxy group. This is because a thiirane group is easier to open a ring and has higher reactivity than an epoxy group. Since the episulfide compound having the structure represented by the above formula (1), (2), (5), (7) or (8) has high reactivity, the anisotropic conductive material is rapidly cured at a low temperature. Can do. In particular, since an episulfide compound having a structure represented by the above formula (1) or (2) has a considerably high reactivity, an anisotropic conductive material can be rapidly cured at a low temperature.
  • R1 and R2 in the above formula (1), R51 and R52 in the above formula (2), R7 in the above formula (3), R59 in the above formula (4), R101 in the above formula (5) and R102, R111 in the above formula (6), R1 and R2 in the above formula (7), and R3 and R4 in the above formula (8) are alkylene groups having 1 to 5 carbon atoms. If the alkylene group has more than 5 carbon atoms, the curing rate of the episulfide compound tends to be slow.
  • R1 and R2 in the above formula (1), R51 and R52 in the above formula (2), R7 in the above formula (3), R59 in the above formula (4), R101 in the above formula (5) and R102, R111 in the above formula (6), R1 and R2 in the above formula (7), and R3 and R4 in the above formula (8) are each preferably an alkylene group having 1 to 3 carbon atoms. More preferably, it is a group.
  • the alkylene group may be an alkylene group having a straight chain structure or an alkylene group having a branched structure.
  • the structure represented by the above (1) is preferably a structure represented by the following formula (1A).
  • An episulfide compound having a structure represented by the following formula (1A) is excellent in curability.
  • R1 and R2 each represent an alkylene group having 1 to 5 carbon atoms.
  • the structure represented by the above formula (1) is more preferably a structure represented by the following formula (1B).
  • An episulfide compound having a structure represented by the following formula (1B) is more excellent in curability.
  • the structure represented by the above (2) is preferably a structure represented by the following formula (2A).
  • An episulfide compound having a structure represented by the following formula (2A) is excellent in curability.
  • R51 and R52 each represent an alkylene group having 1 to 5 carbon atoms.
  • the structure represented by the above formula (2) is more preferably a structure represented by the following formula (2B).
  • An episulfide compound having a structure represented by the following formula (2B) is more excellent in curability.
  • the epoxy compound is not particularly limited.
  • a conventionally well-known epoxy compound can be used as an epoxy compound.
  • As for the said epoxy compound only 1 type may be used and 2 or more types may be used together.
  • Examples of the epoxy compound include phenoxy resin having an epoxy group, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, biphenol type epoxy resin, naphthalene type epoxy resin, fluorene type epoxy resin, phenol aralkyl type epoxy.
  • Examples thereof include a resin, a naphthol aralkyl type epoxy resin, a dicyclopentadiene type epoxy resin, an anthracene type epoxy resin, an epoxy resin having an adamantane skeleton, an epoxy resin having a tricyclodecane skeleton, and an epoxy resin having a triazine nucleus in the skeleton.
  • epoxy compound examples include, for example, epichlorohydrin and bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol D type epoxy resin and the like, bisphenol type epoxy resin, and epichlorohydrin and phenol novolac or cresol novolak.
  • epoxy novolac resins derived from Various epoxy compounds having two or more oxirane groups in one molecule such as glycidylamine, glycidyl ester, and alicyclic or heterocyclic may be used.
  • the curable compound includes an epoxy compound having a structure in which the thiirane group in the structure represented by the formula (1), (2), (5), (7) or (8) is replaced with an epoxy group. Also good.
  • the structures represented by the above formulas (3), (4) and (6) are also preferably structures in which the thiirane group is replaced with an epoxy group.
  • the said curable compound may contain the epoxy compound represented by following formula (11) or (12).
  • the curable compound preferably contains an episulfide compound represented by the above formula (1) or (2) and an epoxy compound represented by the following formula (11) or (12).
  • R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms
  • 2 to 4 groups out of 4 groups of R13, R14, R15 and R16 represent hydrogen
  • R13 , R14, R15 and R16, which are not hydrogen represent a group represented by the following formula (13).
  • All four groups of R13, R14, R15, and R16 in the above formula (11) may be hydrogen.
  • One or two of the four groups of R13, R14, R15 and R16 is a group represented by the following formula (13), and among the four groups of R13, R14, R15 and R16
  • the group that is not a group represented by the following formula (13) may be hydrogen.
  • R17 represents an alkylene group having 1 to 5 carbon atoms.
  • R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms, and 4 to 6 groups out of 6 groups of R63, R64, R65, R66, R67 and R68 are hydrogen.
  • the group which is not hydrogen among R63, R64, R65, R66, R67 and R68 represents a group represented by the following formula (14).
  • All of the six groups of R63, R64, R65, R66, R67 and R68 in the above formula (12) may be hydrogen.
  • One or two of the six groups R63, R64, R65, R66, R67 and R68 are groups represented by the following formula (14), and R63, R64, R65, R66, R67 and R68. Of these six groups, a group that is not a group represented by the following formula (14) may be hydrogen.
  • R69 represents an alkylene group having 1 to 5 carbon atoms.
  • R11 and R12 in the formula (11), R61 and R62 in the formula (12), R17 in the formula (13), and R69 in the formula (14) are alkylene groups having 1 to 5 carbon atoms. It is. If the alkylene group has more than 5 carbon atoms, the curing rate of the epoxy compound represented by the above formula (11) or (12) tends to be slow.
  • R11 and R12 in the above formula (11), R61 and R62 in the above formula (12), R17 in the above formula (13), and R69 in the above formula (14) are each an alkylene having 1 to 3 carbon atoms. It is preferably a group, more preferably a methylene group.
  • the alkylene group may be an alkylene group having a straight chain structure or an alkylene group having a branched structure.
  • the structure represented by the above (11) is preferably a structure represented by the following formula (11A).
  • An epoxy compound having a structure represented by the following formula (11A) is commercially available and can be easily obtained.
  • R11 and R12 each represent an alkylene group having 1 to 5 carbon atoms.
  • the structure represented by the above formula (11) is more preferably a structure represented by the following formula (11B).
  • the epoxy compound having a structure represented by the following formula (11B) is resorcinol diglycidyl ether. Resorcinol diglycidyl ether is commercially available and can be easily obtained.
  • the structure represented by (12) is preferably a structure represented by the following formula (12A).
  • An epoxy compound having a structure represented by the following formula (12A) can be easily obtained.
  • R61 and R62 each represent an alkylene group having 1 to 5 carbon atoms.
  • the structure represented by the above formula (12) is more preferably a structure represented by the following formula (12B).
  • An epoxy compound having a structure represented by the following formula (12B) can be easily obtained.
  • a mixture of an episulfide compound having a structure represented by the above formula (1) or (2) and an epoxy compound represented by the above formula (11) or (12) (hereinafter sometimes abbreviated as “mixture A”)
  • the content of the episulfide compound having the structure represented by the formula (1) or (2) is 10 to 50% by weight
  • the epoxy represented by the formula (11) or (12) The content of the compound is preferably 90 to 50% by weight
  • the content of the episulfide compound having a structure represented by the above formula (1) or (2) is 20 to 30% by weight
  • the above formula (11) Alternatively, the content of the epoxy compound represented by (12) is more preferably 80 to 70% by weight.
  • the curing rate of the mixture A tends to be slow.
  • the viscosity of the said mixture A will become high too much, or the said mixture A may become a solid.
  • the method for producing the mixture A is not particularly limited.
  • Examples of the production method include a production method in which an epoxy compound represented by the above formula (11) or (12) is prepared and a part of the epoxy group of the epoxy compound is converted into a thiirane group.
  • the epoxy compound represented by the above formula (11) or (12) or the solution containing the epoxy compound is continuously or intermittently added to the first solution containing the sulfurizing agent.
  • a method in which the second solution containing the sulfurizing agent is further added continuously or intermittently is preferable.
  • some epoxy groups of the epoxy compound can be converted into thiirane groups.
  • the mixture A can be obtained.
  • the sulfurizing agent include thiocyanates, thioureas, phosphine sulfide, dimethylthioformamide, N-methylbenzothiazole-2-thione, and the like.
  • the thiocyanates include sodium thiocyanate, potassium thiocyanate, and sodium thiocyanate.
  • the curable compound is a monomer of an epoxy compound having a structure represented by the following formula (21), a multimer in which at least two epoxy compounds are bonded, or a mixture of the monomer and the multimer. May be included.
  • R1 represents an alkylene group having 1 to 5 carbon atoms
  • R2 represents an alkylene group having 1 to 5 carbon atoms
  • R3 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms
  • R4 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a structure represented by the following formula (23).
  • R5 represents an alkylene group having 1 to 5 carbon atoms.
  • R6 represents an alkylene group having 1 to 5 carbon atoms.
  • the epoxy compound having a structure represented by the above formula (21) has an unsaturated double bond and at least two epoxy groups.
  • the anisotropic conductive material can be rapidly cured at a low temperature.
  • the curable compound includes a monomer having a structure represented by the following formula (31), a multimer in which at least two of the compounds are bonded, or a mixture of the monomer and the multimer. You may go out.
  • R1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms or a structure represented by the following formula (32), R2 represents an alkylene group having 1 to 5 carbon atoms, and R3 represents carbon X 1 represents an oxygen atom or a sulfur atom, and X 2 represents an oxygen atom or a sulfur atom.
  • R4 represents an alkylene group having 1 to 5 carbon atoms
  • X3 represents an oxygen atom or a sulfur atom.
  • the epoxy compound corresponding to the compound having the structure represented by the above formula (31) can be synthesized as follows, for example.
  • a raw material compound, a fluorene compound having a hydroxyl group, epichlorohydrin, sodium hydroxide, and methanol are mixed, cooled, and reacted. Thereafter, an aqueous sodium hydroxide solution is dropped. After dripping, it is further reacted to obtain a reaction solution. Next, water and toluene are added to the reaction solution, and the toluene layer is taken out. The toluene layer is washed with water and then dried to remove water and the solvent. In this way, an epoxy compound corresponding to the compound having the structure represented by the formula (31) can be easily obtained.
  • the fluorene compound which has a hydroxyl group which is a raw material compound is marketed, for example from JFE Chemical Company etc., for example.
  • the thiirane group-containing compound corresponding to the compound having the structure represented by the above formula (31) has the epoxy group of the epoxy compound corresponding to the compound having the structure represented by the above formula (31) as a thiirane group. It can be synthesized by conversion. For example, an epoxy compound as a raw material compound or a solution containing the epoxy compound is added to the solution containing the sulfurizing agent, and then the solution containing the sulfurizing agent is further added to easily convert the epoxy group to a thiirane group. it can.
  • the curable compound may include an epoxy compound having a heterocyclic ring containing a nitrogen atom.
  • the epoxy compound having a heterocyclic ring containing a nitrogen atom is preferably an epoxy compound represented by the following formula (41) or an epoxy compound represented by the following formula (42).
  • R1 to R3 each represent an alkylene group having 1 to 5 carbon atoms, and Z represents an epoxy group or a hydroxymethyl group.
  • R21 to R23 may be the same or different.
  • R1 to R3 each represents an alkylene group having 1 to 5 carbon atoms
  • p, q and r each represents an integer of 1 to 5
  • R4 to R6 each represents an alkylene group having 1 to 5 carbon atoms. Represents a group.
  • R1 to R3 may be the same or different.
  • p, q and r may be the same or different.
  • R4 to R6 may be the same or different.
  • the epoxy compound having a heterocyclic ring containing a nitrogen atom is preferably triglycidyl isocyanurate or trishydroxyethyl isocyanurate triglycidyl ether.
  • the curable compound preferably contains an epoxy compound having an aromatic ring.
  • an epoxy compound having an aromatic ring By using an epoxy compound having an aromatic ring, the curing rate of the anisotropic conductive material can be further increased and the anisotropic conductive material can be easily applied.
  • the aromatic ring is preferably a benzene ring, a naphthalene ring or an anthracene ring.
  • the epoxy compound having an aromatic ring include resorcinol diglycidyl ether and 1,6-naphthalenediglycidyl ether. Among these, resorcinol diglycidyl ether having a structure represented by the above formula (11B) is particularly preferable. By using resorcinol diglycidyl ether, the curing rate of the anisotropic conductive material can be increased and the anisotropic conductive material can be easily applied.
  • the curable compound according to the present invention may contain a photocurable compound so as to be cured by light irradiation.
  • the curable compound can be semi-cured by light irradiation, and the fluidity of the curable compound can be reduced.
  • the photocurable compound is not particularly limited, and examples thereof include (meth) acrylic resins and cyclic ether group-containing resins.
  • Examples of the (meth) acrylic resin include an ester compound obtained by reacting (meth) acrylic acid and a compound having a hydroxyl group, and an epoxy (meth) acrylate obtained by reacting (meth) acrylic acid and an epoxy compound.
  • Urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with isocyanate is preferably used.
  • the photocurable compound may be a crosslinkable compound or a non-crosslinkable compound.
  • crosslinkable compound examples include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, (poly ) Ethylene glycol di (meth) acrylate, (poly) propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, glycerol methacrylate acrylate, pentaerythritol tri (meth) acrylate, tri Examples include methylolpropane trimethacrylate, allyl (meth) acrylate, vinyl (meth) acrylate, divinylbenzene, polyester (meth) acrylate, and urethane (meth) acrylate.
  • non-crosslinkable compound examples include ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) ) Acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (Meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate,
  • the curable compound contains, for example, a thermosetting compound and a photopolymerizable compound, from the viewpoint of easily controlling the curing of the anisotropic conductive material or further improving the conduction reliability of the connection structure.
  • the curable compound preferably contains a light and thermosetting compound having at least one of an epoxy group and a thiirane group and a (meth) acryloyl group. It is preferable that the said curable compound contains the light and thermosetting compound (henceforth a partial (meth) acrylated epoxy resin) which has an epoxy group and a (meth) acryloyl group.
  • the (meth) acryloyl means acryloyl or methacryloyl.
  • the (meth) acrylate means acrylate or methacrylate.
  • the partial (meth) acrylated epoxy resin can be obtained, for example, by reacting an epoxy resin and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method. It is preferable that 20% or more of the epoxy groups are converted to (meth) acryloyl groups (conversion rate) and partially (meth) acrylated. More preferably, 50% of the epoxy groups are converted to (meth) acryloyl groups.
  • the preferable lower limit of the content of the partially (meth) acrylated epoxy resin is 0.1% by weight and the more preferable lower limit is 0 in 100% by weight of the curable compound.
  • the preferred upper limit is 2 wt%, and the more preferred upper limit is 1.5 wt%.
  • epoxy (meth) acrylate examples include bisphenol type epoxy (meth) acrylate, cresol novolac type epoxy (meth) acrylate, carboxylic acid anhydride-modified epoxy (meth) acrylate, and phenol novolac type epoxy (meth) acrylate. .
  • thermosetting agent The said thermosetting agent is not specifically limited.
  • a conventionally known thermosetting agent can be used as the thermosetting agent.
  • examples of the thermosetting agent include imidazole curing agents, amine curing agents, phenol curing agents, polythiol curing agents, and acid anhydrides.
  • the said thermosetting agent only 1 type may be used and 2 or more types may be used together.
  • the thermosetting agent is preferably an imidazole curing agent, a polythiol curing agent or an amine curing agent.
  • a latent curing agent is preferable because the storage stability of the anisotropic conductive material can be improved.
  • the latent curing agent is preferably a latent imidazole curing agent, a latent polythiol curing agent or a latent amine curing agent.
  • the thermosetting agent may be coated with a polymer material such as polyurethane resin or polyester resin.
  • the imidazole curing agent is not particularly limited, and 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2, 4-Diamino-6- [2'-methylimidazolyl- (1 ')]-ethyl-s-triazine and 2,4-diamino-6- [2'-methylimidazolyl- (1')]-ethyl-s- Examples include triazine isocyanuric acid adducts.
  • the polythiol curing agent is not particularly limited, and examples include trimethylolpropane tris-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol hexa-3-mercaptopropionate. .
  • the amine curing agent is not particularly limited, and hexamethylenediamine, octamethylenediamine, decamethylenediamine, 3,9-bis (3-aminopropyl) -2,4,8,10-tetraspiro [5.5].
  • examples include undecane, bis (4-aminocyclohexyl) methane, metaphenylenediamine, and diaminodiphenylsulfone.
  • the content of the thermosetting agent is not particularly limited.
  • a preferable lower limit of the content of the thermosetting agent is 5 parts by weight, a more preferable lower limit is 10 parts by weight, a preferable upper limit is 30 parts by weight, and a more preferable upper limit is 20 parts by weight with respect to a total of 100 parts by weight of the curable compound. It is. If content of the said thermosetting agent satisfy
  • the photocuring initiator is not particularly limited.
  • a conventionally known photocuring initiator can be used as the photocuring initiator.
  • As for the said photocuring initiator only 1 type may be used and 2 or more types may be used together.
  • the photocuring initiator is not particularly limited, and examples thereof include acetophenone photocuring initiator, benzophenone photocuring initiator, thioxanthone, ketal photocuring initiator, halogenated ketone, acyl phosphinoxide, and acyl phosphonate. .
  • acetophenone photocuring initiator examples include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, methoxy Examples include acetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, and 2-hydroxy-2-cyclohexylacetophenone.
  • ketal photocuring initiator examples include benzyldimethyl ketal.
  • the content of the photocuring initiator is not particularly limited.
  • the preferable lower limit of the content of the photocuring initiator is 0.1 parts by weight, the more preferable lower limit is 0.2 parts by weight, and the preferable upper limit is 2 parts by weight with respect to the total of 100 parts by weight of the curable compound.
  • the upper limit is 1 part by weight. If content of the said photocuring initiator satisfy
  • the conductive particles contained in the anisotropic conductive material according to the present invention for example, conventionally known conductive particles capable of electrically connecting the electrodes are used.
  • the conductive particles are preferably particles having a conductive layer on the outer surface.
  • the conductive particles may have insulating particles attached to the surface of the conductive layer, or the surface of the conductive layer may be covered with an insulating layer. In this case, the insulating particles or the insulating layer is removed by pressurization when the electrodes are connected.
  • the conductive particles include organic particles, inorganic particles, organic-inorganic hybrid particles, or conductive particles whose surfaces are covered with a conductive layer, and metal particles that are substantially composed of only metal. Is mentioned.
  • the conductive layer is not particularly limited. Examples of the conductive layer include a gold layer, a silver layer, a copper layer, a nickel layer, a palladium layer, or a conductive layer containing tin.
  • the content of the conductive particles is in the range of 1 to 19% by weight.
  • the minimum with preferable content of the said electroconductive particle is 5 weight%, a preferable upper limit is 15 weight%, and a more preferable upper limit is 10 weight%.
  • the conductive particles can be easily arranged between the upper and lower electrodes to be connected. Furthermore, it becomes difficult to electrically connect adjacent electrodes that should not be connected via a plurality of conductive particles. That is, a short circuit between adjacent electrodes can be prevented.
  • the anisotropic conductive material according to the present invention may contain a solvent.
  • the solvent By using the solvent, the viscosity of the anisotropic conductive material can be easily adjusted.
  • the dispersibility of the curable compound can be increased by adding a solvent to the solid curable compound and dissolving it.
  • the solvent include ethyl acetate, methyl cellosolve, toluene, acetone, methyl ethyl ketone, cyclohexane, n-hexane, tetrahydrofuran and diethyl ether.
  • the anisotropic conductive material according to the present invention preferably contains an adhesive strength adjusting agent.
  • the adhesive strength modifier is preferably a silane coupling agent.
  • the anisotropic conductive material according to the present invention preferably contains a filler.
  • a filler By using the filler, latent heat expansion of the cured product of the anisotropic conductive material can be suppressed.
  • the filler is preferably surface-treated, and is preferably a hydrophilic filler.
  • the filler is not particularly limited.
  • Examples of the filler include silica, aluminum nitride, and alumina.
  • As for the said filler only 1 type may be used and 2 or more types may be used together.
  • the hydrophilic filler is a filler whose surface is covered with a hydrophilic group.
  • the hydrophilic group include polar groups such as hydroxyl group, amino group, amide group, carboxylate group and carboxyl group, and ionic groups such as carboxylate ion group, sulfonate ion group and ammonium ion group.
  • the hydrophilic filler include a hydrophilic filler obtained by surface-treating the conventional filler with a hydrophilic surface treatment agent.
  • hydrophilic surface treatment agent examples include silane coupling agents, titanate coupling agents, aluminum coupling agents, zircoaluminate coupling agents, Al 2 O 3 , TiO 2 , ZrO 2 , silicone, and stearin. An aluminum acid etc. are mentioned. Among these, a silane coupling agent is preferably used as the hydrophilic surface treatment agent.
  • the content of the filler is not particularly limited.
  • the preferable lower limit of the filler content is 5 parts by weight, the more preferable lower limit is 15 parts by weight, the preferable upper limit is 70 parts by weight, and the more preferable upper limit is 50 parts by weight with respect to the total of 100 parts by weight of the curable compound. .
  • content of the said filler satisfy
  • anisotropic conductive material It does not specifically limit as a manufacturing method of the anisotropic electrically-conductive material which concerns on this invention, Adds the said sclerosing
  • the viscosity of the anisotropic conductive material according to the present invention at 25 ° C. and 2.5 rpm is preferably in the range of 20 to 200 Pa ⁇ s. That is, the viscosity of the anisotropic conductive material before coating at 25 ° C. and 2.5 rpm is preferably in the range of 20 to 200 Pa ⁇ s.
  • the flow of the anisotropic conductive material before curing can be further suppressed after applying the anisotropic conductive material on the application target member (first connection target member) such as a substrate.
  • the resin component between the electrode and the conductive particles can be easily removed, and the contact area between the electrode and the conductive particles can be increased.
  • the surface of the application target member (first connection target member) is uneven
  • the surface of the unevenness can be sufficiently filled with an anisotropic conductive material, and voids are less likely to occur after curing. Further, it becomes difficult for the conductive particles to settle in the anisotropic conductive material, and the dispersibility of the conductive particles can be improved.
  • the viscosity after being cured by light irradiation to be B-staged (hereinafter sometimes abbreviated as ⁇ 3 ′) is in the range of 2000 to 3500 Pa ⁇ s. Preferably there is. From the viewpoint of further suppressing the flow of the anisotropic conductive material layer and the conductive particles, the more preferable lower limit of the viscosity ⁇ 3 'is 2250 Pa ⁇ s, and the more preferable upper limit is 3250 Pa ⁇ s. The preferable lower limit of the measurement temperature of the viscosity ⁇ 3 'is 20 ° C, and the preferable upper limit is 30 ° C. The measurement temperature of the viscosity ⁇ 3 ′ is particularly preferably 25 ° C.
  • the anisotropic conductive material according to the present invention when the viscosity at 25 ° C. and 2.5 rpm is ⁇ 1, and the viscosity at 25 ° C. and 5 rpm is ⁇ 2, the ⁇ 2 is 20 Pa ⁇ s or more and 200 Pa ⁇ s or less. And the ratio ( ⁇ 1 / ⁇ 2) of ⁇ 1 to ⁇ 2 is preferably 0.9 or more and 1.1 or less. That is, the anisotropic conductive material according to the present invention preferably satisfies both the following formulas (X) and (Y). 20 Pa ⁇ s ⁇ ⁇ 2 ⁇ 200 Pa ⁇ s Formula (X) 0.9 ⁇ ⁇ 1 / ⁇ 2 ⁇ 1.1 Formula (Y)
  • the anisotropic conductive material according to the present invention when the ⁇ 2 and the ratio ( ⁇ 1 / ⁇ 2) are within the specific range, the anisotropic conductive material is dispensed by a dispenser or the like.
  • the coating width can be made constant, and as a result, variations in the width or thickness of the cured product layer formed of the anisotropic conductive material are less likely to occur.
  • the preferable lower limit of ⁇ 2 is 50 Pa ⁇ s
  • the more preferable lower limit is 100 Pa ⁇ s
  • the preferable upper limit is 180 Pa ⁇ s
  • the more preferable upper limit is 150 Pa ⁇ s. .
  • the above ⁇ 2 and the above ratio ( ⁇ 1 / ⁇ 2) can be adjusted by using a crystalline resin as the curable compound or by using a filler that has been surface-treated to enhance hydrophilicity.
  • the curable compound preferably contains a crystalline resin.
  • the anisotropic conductive material As a method for curing the anisotropic conductive material according to the present invention, after the anisotropic conductive material is irradiated with light, the anisotropic conductive material is heated, and after the anisotropic conductive material is heated, the anisotropic conductive material is heated.
  • a method of irradiating the anisotropic conductive material with light can be given.
  • the photocuring speed and the thermosetting speed are different, light irradiation and heating may be performed simultaneously.
  • the method of heating an anisotropic conductive material after irradiating light to an anisotropic conductive material is preferable.
  • the anisotropic conductive material can be cured in a short time by the combined use of photocuring and heat curing.
  • connection structure can be obtained by connecting the connection target members using the anisotropic conductive material according to the present invention.
  • connection structure includes a first connection target member, a second connection target member, and a connection portion that electrically connects the first and second connection target members.
  • the part is preferably formed of the anisotropic conductive material.
  • the connection portion is a cured product layer obtained by curing the anisotropic conductive material.
  • connection structure using an anisotropic conductive material according to an embodiment of the present invention and a method for manufacturing the connection structure will be described in more detail with reference to the drawings.
  • FIG. 1 schematically shows an example of a connection structure using an anisotropic conductive material according to an embodiment of the present invention in a partially cutaway front sectional view.
  • the cured product layer 3 is a connection part.
  • the cured product layer 3 is formed by curing an anisotropic conductive material including a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles 5.
  • the anisotropic conductive material includes a plurality of conductive particles 5.
  • a plurality of electrodes 2 b are provided on the upper surface 2 a of the first connection target member 2.
  • a plurality of electrodes 4 b are provided on the lower surface 4 a of the second connection target member 4.
  • the electrode 2b and the electrode 4b are electrically connected by one or a plurality of conductive particles 5.
  • connection structure 1 a glass substrate is used as the first connection target member 2, and a semiconductor chip is used as the second connection target member 4.
  • the first and second connection target members are not particularly limited. Specific examples of the first and second connection target members include electronic components such as semiconductor chips, capacitors, and diodes, and circuit boards such as printed boards, flexible printed boards, and glass boards.
  • connection structure 1 shown in FIG. 1 can be obtained as follows, for example.
  • a first connection target member 2 having an electrode 2b on the upper surface 2a is prepared.
  • an anisotropic conductive material including a plurality of conductive particles 5 is applied to the upper surface 2a of the first connection target member 2, and the anisotropic conductive material layer 3A is applied to the upper surface 2a of the first connection target member 2.
  • the anisotropic conductive material layer 3A is cured by irradiating the anisotropic conductive material layer 3A with light.
  • the anisotropic conductive material layer 3A is B-staged.
  • a B-staged anisotropic conductive material layer 3B is formed on the upper surface 2a of the first connection target member 2.
  • the viscosity of the B-staged anisotropic conductive material layer 3B (hereinafter abbreviated as ⁇ 3).
  • the anisotropic conductive material layer 3A is preferably B-staged so that it is within the range of 2000 to 3500 Pa ⁇ s.
  • the flow of the anisotropic conductive material layer can be sufficiently suppressed. For this reason, it becomes easy to arrange the conductive particles 5 between the electrodes 2b and 4b. Furthermore, it is possible to suppress the anisotropic conductive material layer from flowing unintentionally in a region lateral to the outer peripheral surface of the first connection target member 2 or the second connection target member 4.
  • a more preferable lower limit of the viscosity ⁇ 3 is 2250 Pa ⁇ s, and a more preferable upper limit is 3250 Pa ⁇ s.
  • the preferable lower limit of the measurement temperature of the viscosity ⁇ 3 is 20 ° C., and the preferable upper limit is 30 ° C.
  • the measurement temperature of the viscosity ⁇ 3 is particularly preferably 25 ° C.
  • connection structure 1 It is preferable to irradiate the anisotropic conductive material layer 3A with light while applying the anisotropic conductive material to the upper surface 2a of the first connection target member 2. Furthermore, it is also preferable to irradiate the anisotropic conductive material layer 3 ⁇ / b> A simultaneously with the application of the anisotropic conductive material to the upper surface 2 a of the first connection target member 2 or immediately after the application.
  • application and light irradiation are performed as described above, the flow of the anisotropic conductive material layer can be further suppressed. For this reason, the conduction
  • the time from application of the anisotropic conductive material to the upper surface 2a of the first connection target member 2 until irradiation with light is preferably within a range of 0 to 3 seconds, and within a range of 0 to 2 seconds. It is more preferable that
  • connection structure 1 It is preferable to irradiate the anisotropic conductive material layer 3A with light while applying the anisotropic conductive material to the upper surface 2a of the first connection target member 2. Furthermore, it is also preferable to irradiate the anisotropic conductive material layer 3 ⁇ / b> A simultaneously with the application of the anisotropic conductive material to the upper surface 2 a of the first connection target member 2 or immediately after the application.
  • application and light irradiation are performed as described above, the flow of the anisotropic conductive material layer can be further suppressed. For this reason, the conduction
  • the time from application of the anisotropic conductive material to the upper surface 2a of the first connection target member 2 until irradiation with light is preferably within a range of 0 to 3 seconds, and within a range of 0 to 2 seconds. It is more preferable that
  • the light irradiation intensity for appropriately proceeding curing of the anisotropic conductive material layer 3A is, for example, 0.1 to 100 mW / cm. It is about 2 .
  • the light source used when irradiating light is not particularly limited.
  • the light source include a light source having a sufficient light emission distribution at a wavelength of 420 nm or less.
  • Specific examples of the light source include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a chemical lamp, a black light lamp, a microwave excitation mercury lamp, and a metal halide lamp.
  • the second connection target member 4 is laminated on the upper surface 3a of the B-staged anisotropic conductive material layer 3B.
  • the second connection target member 4 is laminated so that the electrode 2b on the upper surface 2a of the first connection target member 2 and the electrode 4b on the lower surface 4a of the second connection target member 4 face each other.
  • the anisotropic conductive material layer 3B is further cured by applying heat to the anisotropic conductive material layer 3B, thereby forming the cured product layer 3.
  • heat may be applied to the anisotropic conductive material layer 3B before the second connection target member 4 is laminated.
  • the preferable lower limit of the heating temperature for sufficiently curing the anisotropic conductive material layer 3B is 160 ° C
  • the preferable upper limit is 250 ° C
  • the more preferable upper limit Is 200 ° C.
  • pressure By compressing the conductive particles 5 with the electrodes 2b and 4b by pressurization, the contact area between the electrodes 2b and 4b and the conductive particles 5 can be increased. For this reason, conduction reliability can be improved.
  • connection target member 2 and the second connection target member 4 are connected via the cured product layer 3 by curing the anisotropic conductive material layer 3B. Further, the electrode 2 b and the electrode 4 b are electrically connected through the conductive particles 5. In this way, the connection structure 1 shown in FIG. 1 can be obtained. In this embodiment, since photocuring and thermosetting are used together, the anisotropic conductive material can be cured in a short time.
  • the anisotropic conductive material layer 3A is irradiated with light to form a B-staged anisotropic conductive material layer 3B, and then heat is applied to the anisotropic conductive material layer 3B. It is preferable to do.
  • the composite apparatus shown in FIG. 3A is preferably used.
  • the dispenser 12 includes a syringe 12a for filling the inside with an anisotropic conductive material, and a grip portion 12b that grips the outer peripheral surface of the syringe 12a.
  • the light irradiation device 13 includes a light irradiation device main body 13a and a light irradiation unit 13b. In the composite apparatus 11, the grip part 12b and the light irradiation apparatus main body 13a are connected. Therefore, the distance between the dispenser 12 and the light irradiation device 13 can be reduced, that is, the distance between the discharge part of the dispenser 12 and the light irradiation part 13b can be reduced. Furthermore, the dispenser 12 and the light irradiation device 13 can be easily moved at the same speed.
  • the syringe 12a and the light irradiation apparatus main body 13a may be directly connected.
  • the syringe 12a when applying and irradiating light, while moving the composite device 11 in the direction of arrow A, the syringe 12a is anisotropically moved from the syringe 12a to the upper surface 2a of the first connection target member 2.
  • a conductive conductive material is applied to form the anisotropic conductive material layer 3A.
  • the anisotropic conductive material layer 3 ⁇ / b> A is irradiated with light from the light irradiation unit 13 b of the light irradiation device 13 connected to the dispenser 12 as indicated by an arrow B while being applied.
  • the dispenser 12 and the light irradiation device 13 are moved at the same speed from the viewpoint of controlling the time until the light irradiation with high accuracy.
  • the table 31 may be moved in the direction of the arrow A without moving the composite apparatus 11.
  • the light irradiation device 21 includes a light irradiation device main body 21 a and a light irradiation unit 21 b.
  • the light irradiation device 21 is configured to irradiate light over a wider area than the light irradiation device 13.
  • the light irradiation device 21 When using the dispenser 12 and the light irradiation device 21 not connected to the dispenser 12, for example, as shown in FIG. 4A, the light irradiation device 21 is placed above the first connection target member 2. Deploy. Next, while the dispenser 12 is moved in the direction of the arrow A between the first connection target member 2 and the light irradiation device 21, anisotropic conduction is performed from the syringe 12 a to the upper surface 2 a of the first connection target member 2. The material is applied to form the anisotropic conductive material layer 3A. Next, as shown in FIG.
  • the light irradiation unit 21b of the light irradiation device 21 disposed above the first connection target member 2 is different from the first irradiation target member 2.
  • the isotropic conductive material layer 3A is irradiated with light. The light irradiation is performed, for example, simultaneously with the application of the anisotropic conductive material or immediately after the application.
  • the light irradiation device 21 is disposed above the first connection target member 2 at the time of application. In this case, light can be irradiated quickly after application. After the application, it is preferable to irradiate the entire region of the anisotropic conductive material layer 3A all together. In this case, the anisotropic conductive material layer 3A can be made B-stage even more uniformly.
  • the anisotropic conductive material is applied simultaneously or immediately after the application of the anisotropic conductive material to the upper surface 2a of the first connection target member 2.
  • the material layer 3A can be easily irradiated with light.
  • the anisotropic conductive material used in the method for manufacturing a connection structure according to the present invention contains a curable compound, a thermosetting agent, a photocuring initiator, and conductive particles.
  • the flow of the anisotropic conductive material applied to the upper surface 2a of the member 2 or the conductive particles contained in the anisotropic conductive material can be sufficiently suppressed.
  • the anisotropic conductive material and the connection structure manufacturing method according to the present invention include, for example, connection between a flexible printed circuit board and a glass substrate (FOG (Film on Glass)), connection between a semiconductor chip and a flexible printed circuit board (COF ( (Chip on Film)) or a connection between a semiconductor chip and a glass substrate (COG (Chip on Glass)) or the like.
  • the manufacturing method of the anisotropic electrically-conductive material and connection structure which concern on this invention is suitable for a COG use.
  • the manufacturing method of the anisotropic conductive material and the connection structure according to the present invention is suitably used for the connection between the semiconductor chip and the glass substrate.
  • the use of the anisotropic conductive material and the connection structure manufacturing method according to the present invention is not limited to the above-described use.
  • the distance between adjacent electrodes of a semiconductor chip and the distance between adjacent electrodes of a glass substrate may be about 10 to 20 ⁇ m, and fine wiring is often formed. Even if fine wiring is formed, the anisotropic conductive material and the manufacturing method of the connection structure according to the present invention can connect the electrodes of the semiconductor chip and the glass substrate with high accuracy, and the conduction reliability. Can be increased.
  • Example 1 (1) Preparation of episulfide compound-containing mixture In a 2 L vessel equipped with a stirrer, a cooler and a thermometer, ethanol 250 mL, pure water 250 mL, and potassium thiocyanate 20 g were added to dissolve potassium thiocyanate, One solution was prepared. Thereafter, the temperature in the container was kept within the range of 20 to 25 ° C. Next, 160 g of resorcinol diglycidyl ether was added dropwise at a rate of 5 mL / min to the first solution while stirring the first solution in a container maintained at 20 to 25 ° C. After dropping, the mixture was further stirred for 30 minutes to obtain an epoxy compound-containing mixed solution.
  • a second solution in which 20 g of potassium thiocyanate was dissolved in a solution containing 100 mL of pure water and 100 mL of ethanol was prepared.
  • the obtained second solution was added to the obtained epoxy group-containing mixed solution at a rate of 5 mL / min, and then stirred for 30 minutes.
  • a second solution in which 20 g of potassium thiocyanate is dissolved in a solution containing 100 mL of pure water and 100 mL of ethanol is further prepared, and the second solution is further added to the container at a rate of 5 mL / min. And stirred for 30 minutes. Thereafter, the temperature in the container was cooled to 10 ° C., and stirred for 2 hours to be reacted.
  • magnesium sulfate was added to the supernatant liquid to which toluene was added and stirred for 5 minutes. After stirring, magnesium sulfate was removed with a filter paper to separate the solution. The remaining solvent was removed by drying the separated solution under reduced pressure at 80 ° C. using a vacuum dryer. In this way, an episulfide compound-containing mixture was obtained.
  • the resulting episulfide compound-containing mixture was subjected to 1 H-NMR measurement using chloroform as a solvent. As a result, the signal in the 6.5 to 7.5 ppm region indicating the presence of the epoxy group decreased, and the signal appeared in the 2.0 to 3.0 ppm region indicating the presence of the episulfide group. This confirmed that some epoxy groups of resorcinol diglycidyl ether were converted into episulfide groups. From the integral value of the measurement result of 1 H-NMR, the episulfide compound-containing mixture contains 70% by weight of resorcinol diglycidyl ether and 30% by weight of the episulfide compound having the structure represented by the above formula (1B). It was confirmed.
  • anisotropic conductive paste 30 parts by weight of the resulting episulfide compound-containing mixture, 5 parts by weight of an amine adduct (“PN-23J” manufactured by Ajinomoto Fine Techno Co.) as a thermosetting agent, and a photocurable compound 5 parts by weight of epoxy acrylate (“EBECRYL 3702" manufactured by Daicel-Cytec), 0.1 parts by weight of acylphosphine oxide compound ("DAROCUR TPO" manufactured by Ciba Japan) as a photopolymerization initiator, and curing acceleration 1 part by weight of 2-ethyl-4-methylimidazole as an agent, 20 parts by weight of silica having an average particle diameter of 0.25 ⁇ m and 20 parts by weight of alumina having an average particle diameter of 0.5 ⁇ m are blended, and average particles Conductive particles having a diameter of 3 ⁇ m were added so that the content in 100% by weight of the composition was 10% by weight. , By stirring for 5 minutes at 2000rpm using a
  • the conductive particles used are conductive particles having a metal layer in which a nickel plating layer is formed on the surface of divinylbenzene resin particles and a gold plating layer is formed on the surface of the nickel plating layer. is there.
  • the obtained composition was filtered using a nylon filter paper (pore diameter: 10 ⁇ m) to obtain an anisotropic conductive paste having a conductive particle content of 10% by weight.
  • a transparent glass substrate having an ITO electrode pattern with an L / S of 30 ⁇ m / 30 ⁇ m formed on the upper surface was prepared. Further, a semiconductor chip was prepared in which a copper electrode pattern having L / S of 30 ⁇ m / 30 ⁇ m was formed on the lower surface.
  • the obtained anisotropic conductive paste was applied on the transparent glass substrate so as to have a thickness of 30 ⁇ m to form an anisotropic conductive paste layer.
  • the anisotropic conductive paste layer was irradiated with ultraviolet rays using an ultraviolet irradiation lamp, and the anisotropic conductive paste layer was semi-cured by photopolymerization to form a B stage.
  • the semiconductor chip was stacked on the anisotropic conductive paste layer so that the electrodes face each other.
  • a pressure heating head is placed on the upper surface of the semiconductor chip, and the pressure of 3 MPa is applied to apply the anisotropic conductive paste layer. Completely cured at 185 ° C. to obtain a connection structure.
  • Example 2 In the preparation of the anisotropic conductive paste, the conductive particles were used in the same manner as in Example 1 except that the conductive particles were used so that the content in 100% by weight of the blend was 5% by weight. An anisotropic conductive paste having a content of 5% by weight was obtained. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Example 3 In the preparation of the anisotropic conductive paste, the conductive particles were used in the same manner as in Example 1 except that the conductive particles were used so that the content in 100% by weight of the blend was 15% by weight. An anisotropic conductive paste having a content of 15% by weight was obtained. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Example 4 In the preparation of the anisotropic conductive paste, the conductive particles were used in the same manner as in Example 1 except that the conductive particles were used so that the content in 100% by weight of the composition was 1% by weight. An anisotropic conductive paste having a content of 1 wt% was obtained. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Anisotropic conductive paste was prepared in the same manner as in Example 1 except that epoxy acrylate as a photocurable compound and acylphosphine oxide compound as a photopolymerization initiator were not used. Conductive paste was obtained. In 100% by weight of the obtained anisotropic conductive paste, the content of conductive particles was 10% by weight. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Example 2 In the preparation of the anisotropic conductive paste, the conductive particles were used in the same manner as in Example 1 except that the conductive particles were used so that the content in 100% by weight of the blend was 20% by weight. An anisotropic conductive paste having a content of 20 wt% was obtained. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Example 3 In the preparation of the anisotropic conductive paste, the conductive particles were used in the same manner as in Example 1 except that the conductive particles were used so that the content in 100% by weight of the blend was 0.1% by weight. An anisotropic conductive paste having a particle content of 0.1% by weight was obtained. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • connection structure Presence or absence of leakage Using the obtained connection structure, whether or not leakage occurred in 20 adjacent electrodes was measured with a tester.
  • connection structure Presence / absence of voids In the obtained connection structure, whether or not voids were generated in the cured product layer formed of the anisotropic conductive paste layer was visually observed from the lower surface side of the transparent glass substrate.
  • the anisotropic conductive pastes of Examples 1 to 4 had no leaks and no voids.
  • the anisotropic conductive paste of Comparative Example 1 since it was not semi-cured by photopolymerization when irradiated with ultraviolet rays, the anisotropic conductive paste flowed more to the side than the outer peripheral surface of the semiconductor chip during pressurization and heating. For this reason, the anisotropic conductive paste was insufficiently filled between the glass substrate and the semiconductor chip, and voids were observed.
  • Example 5 The anisotropic conductive material obtained in Example 1 was prepared.
  • a transparent glass substrate having an ITO electrode pattern with an L / S of 30 ⁇ m / 30 ⁇ m formed on the upper surface was prepared. Further, a semiconductor chip was prepared in which a copper electrode pattern having L / S of 30 ⁇ m / 30 ⁇ m was formed on the lower surface.
  • a composite apparatus including a dispenser as shown in FIG. 3A and an ultraviolet irradiation lamp as a light irradiation apparatus connected to the dispenser was prepared.
  • the anisotropic conductive paste obtained was applied from the syringe of the dispenser to the upper surface of the transparent glass substrate so as to have a thickness of 30 ⁇ m to form an anisotropic conductive paste layer. Further, while moving the composite device and applying the anisotropic conductive paste, using the ultraviolet irradiation lamp on the anisotropic conductive paste layer, the ultraviolet irradiation of 420 nm is irradiated so that the light irradiation intensity becomes 50 mW / cm 2. Then, the anisotropic conductive paste layer was B-staged by photopolymerization. The time T from the time when the anisotropic conductive paste was applied to the transparent glass substrate to the time when the anisotropic conductive paste layer was irradiated with light was 0.5 seconds. .
  • the semiconductor chip was stacked on the upper surface of the B-staged anisotropic conductive paste layer so that the electrodes face each other. Then, while adjusting the temperature of the head so that the temperature of the anisotropic conductive paste layer becomes 185 ° C., a pressure heating head is placed on the upper surface of the semiconductor chip, and a pressure of 3 MPa is applied to make the B-staged difference. The isotropic conductive paste layer was completely cured at 185 ° C. to obtain a connection structure.
  • Example 6 An anisotropic conductive paste was obtained in the same manner as in Example 1 except that the epoxy acrylate was changed to urethane acrylate ("EBECRYL8804" manufactured by Daicel-Cytec Co., Ltd.) during the preparation of the anisotropic conductive paste.
  • EBECRYL8804 urethane acrylate
  • connection structure was obtained in the same manner as in Example 5 except that the obtained anisotropic conductive paste was used.
  • Example 7 The anisotropic conductive material obtained in Example 1 was prepared.
  • An anisotropic conductive paste is applied using a dispenser shown in FIG. 4A and an ultraviolet irradiation lamp as a light irradiation device not connected to the dispenser, instead of the composite device shown in FIG.
  • a connection structure was obtained in the same manner as in Example 5 except that the light was irradiated immediately after the completion of.
  • the time T from application to irradiation with light was 2 seconds.
  • Comparative Example 4 The anisotropic conductive material obtained in Comparative Example 1 was prepared.
  • a transparent glass substrate having an ITO electrode pattern with an L / S of 30 ⁇ m / 30 ⁇ m formed on the upper surface was prepared. Further, a semiconductor chip was prepared in which a copper electrode pattern having L / S of 30 ⁇ m / 30 ⁇ m was formed on the lower surface.
  • the obtained anisotropic conductive paste was applied on the upper surface of the transparent glass substrate from a syringe of a dispenser so as to have a thickness of 30 ⁇ m to form an anisotropic conductive paste layer. No light was applied during and after application.
  • the semiconductor chip was laminated on the upper surface of the anisotropic conductive paste layer so that the electrodes face each other. Then, while adjusting the temperature of the head so that the temperature of the anisotropic conductive paste layer becomes 185 ° C., a pressure heating head is placed on the upper surface of the semiconductor chip and a pressure of 3 MPa is applied to form the anisotropic conductive paste layer. Completely cured at 185 ° C. to obtain a connection structure.
  • a transparent glass substrate having an ITO electrode pattern with an L / S of 30 ⁇ m / 30 ⁇ m formed on the upper surface was prepared. Further, a semiconductor chip was prepared in which a copper electrode pattern having L / S of 30 ⁇ m / 30 ⁇ m was formed on the lower surface.
  • the obtained anisotropic conductive paste was applied on the upper surface of the transparent glass substrate from a syringe of a dispenser so as to have a thickness of 30 ⁇ m to form an anisotropic conductive paste layer.
  • light was not irradiated, thermal polymerization was not performed, and the anisotropic conductive material layer was not B-staged.
  • the semiconductor chip was laminated on the upper surface of the anisotropic conductive paste layer that was not B-staged so that the electrodes face each other. Then, while adjusting the temperature of the head so that the temperature of the anisotropic conductive paste layer becomes 185 ° C., a pressure heating head is placed on the upper surface of the semiconductor chip and a pressure of 3 MPa is applied to form the anisotropic conductive paste layer. Completely cured at 185 ° C. to obtain a connection structure.
  • Viscosity of the B-staged anisotropic conductive paste layer After the anisotropic conductive paste layer is B-staged by photopolymerization, on the upper surface of the B-staged anisotropic conductive paste layer The viscosity of the B-staged anisotropic conductive paste layer immediately before stacking the semiconductor chips was measured using a rheometer (manufactured by Anton Paar) at 25 ° C. and 2.5 rpm.
  • Example 8 Resorcinol type epoxy resin (crystalline resin, “EX-201” manufactured by Nagase ChemteX Corporation), 16 parts by weight, naphthalene type epoxy resin (crystalline resin, “HP-4032” manufactured by DIC), 14 parts by weight, and thermosetting 5 parts by weight of an amine adduct (“PN-23J” manufactured by Ajinomoto Fine Techno Co.) as an agent, 5 parts by weight of an epoxy acrylate (“EBECRYL 3702” manufactured by Daicel-Cytech) as a photocurable resin, 0.1 part by weight of an acylphosphine oxide compound (“DAROCUR TPO” manufactured by Ciba Japan), 1 part by weight of 2-ethyl-4-methylimidazole as a curing accelerator, and an average particle size of 0.
  • PN-23J manufactured by Ajinomoto Fine Techno Co.
  • the conductive particles used are conductive particles having a metal layer in which a nickel plating layer is formed on the surface of divinylbenzene resin particles and a gold plating layer is formed on the surface of the nickel plating layer. is there.
  • the obtained composition was filtered using nylon filter paper (pore diameter: 10 ⁇ m) to obtain an anisotropic conductive paste.
  • a connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • Example 9 Other than changing the addition amount of resorcinol type epoxy resin from 16 parts by weight to 25 parts by weight and changing 14 parts by weight of naphthalene type epoxy resin to 5 parts by weight of bisphenol A type epoxy resin (“Epicoat 1001” manufactured by JER) Obtained an anisotropic conductive paste in the same manner as in Example 8. A connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • the obtained composition was filtered using nylon filter paper (pore diameter: 10 ⁇ m) to obtain an anisotropic conductive paste.
  • a connection structure was obtained in the same manner as in Example 1 except that the obtained anisotropic conductive paste was used.
  • the obtained anisotropic conductive paste was filled into a syringe having a nozzle diameter of 1.1 mm, and using a dispenser, the pressure was 300 Pa, the coating thickness was 30 ⁇ m, the moving speed was 10 mm / s, the coating line distance was 20 mm, and An anisotropic conductive paste was applied on a glass substrate under the condition of an application width of 1 mm.
  • the coating width at each point of 2 mm, 5 mm, and 10 mm from the application start point of the anisotropic conductive paste was measured with a microscope with a length measuring function.
  • the anisotropic conductive pastes of Examples 8 to 9 could be applied stably and the application width was almost constant. Furthermore, in the anisotropic conductive paste of Example 8, since the flow of the anisotropic conductive paste was suppressed at the time of application, the thickness of the obtained cured product layer was 30 ⁇ m.
  • the coating amount varied and the coating width varied even though the coating pressure was constant.

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PCT/JP2010/064077 2009-08-26 2010-08-20 異方性導電材料、接続構造体及び接続構造体の製造方法 WO2011024719A1 (ja)

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