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WO2011021780A2 - Composition pour film conducteur anisotrope - Google Patents

Composition pour film conducteur anisotrope Download PDF

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Publication number
WO2011021780A2
WO2011021780A2 PCT/KR2010/004720 KR2010004720W WO2011021780A2 WO 2011021780 A2 WO2011021780 A2 WO 2011021780A2 KR 2010004720 W KR2010004720 W KR 2010004720W WO 2011021780 A2 WO2011021780 A2 WO 2011021780A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
anisotropic conductive
epoxy
resin
conductive film
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2010/004720
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English (en)
Korean (ko)
Other versions
WO2011021780A3 (fr
Inventor
박영우
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cheil Industries Inc
Original Assignee
Cheil Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cheil Industries Inc filed Critical Cheil Industries Inc
Publication of WO2011021780A2 publication Critical patent/WO2011021780A2/fr
Publication of WO2011021780A3 publication Critical patent/WO2011021780A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/10—Metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons

Definitions

  • This invention relates to the composition for anisotropic conductive films which can be used as a connection material of a liquid crystal display device and a display apparatus panel, and the anisotropic conductive film by the composition.
  • FCCL Flexible Copper Clad Laminate
  • FCCL method has wide space and relatively thick copper foil, so the physical properties of anisotropic conductive film composed of epoxy resin and phenoxy resin are mainly used. The binding could be excellent.
  • the epoxy-based adhesive is exposed in the FCCL space part, and thus the chemical usability is good, and it has excellent adhesion and connection reliability.
  • FOG Flexible Printed Circuit Board
  • FPCB Flexible Printed Circuit Board
  • the cured products of conventional bisphenol-A type (BPA) type epoxy resins, bisphenol-F type (BPF) type epoxy resins, phenoxy resins and small amount of rubber resins are hard and strong, but hard Absorption capacity is weak and has brittleness. Regarding the reliability, there is a problem that bubbles are generated and a problem of deterioration of adhesion is more prominent in the two-layer non-adhesive FPCB than the three-layer adhesive FPCB.
  • the thickness of the copper foil is relatively thin, thereby causing a problem of physical adhesion deterioration, and the above-mentioned problem occurs because the FPCB space part is made of a polyimide film without epoxy adhesive. do.
  • the present invention appropriately controls the content of the polycyclic aromatic ring-containing epoxy resin and acrylic rubber resin, so as to compensate for brittle properties of the epoxy resin in a high temperature and high humidity state so that the anisotropic conductive film of the curing state is not broken.
  • An object of the present invention is to provide a composition for anisotropic conductive films having both flexibility and layer resistance.
  • an object of the present invention is to provide a composition for an anisotropic conductive film that can lower the connection resistance and supplement the heat stabilized partial.
  • an object of the present invention is to provide an anisotropic conductive film having high reliability and high adhesion.
  • the composition for anisotropic conductive films of the present invention comprises a polycyclic aromatic ring-containing epoxy resin, an acrylic rubber-based resin, conductive particles and a curing agent, and the polycyclic aromatic ring-containing epoxy resin has a glass transition temperature (Tg) after curing. It is about 165 ° C ⁇ 220 ° C, and the acrylic rubber resin has a glass transition temperature (Tg) of about 0 ° C ⁇ 20 ° C after curing, the content of the polycyclic aromatic ring-containing epoxy resin and acrylic rubber resin The sum is about 45 to 65% by weight of the total weight of the composition (solid content).
  • polycyclic aromatic ring-containing epoxy resin is cured from an epoxy monomer having the structure of Formula 2:
  • (Ar) n -E m In the above, (Ar) n is a polycyclic aromatic hydrocarbon, n is 2 to 4 as the number of benzene ring, E is selected from an epoxy group, glycidyl group or glycidyloxy group, m Is 1 to 3. In embodiments, the polycyclic aromatic . Gora-containing epoxy resin
  • the acrylic rubber resin may be a copolymer of two or more kinds of Cl-20 alkyl acrylates and one or more comonomers selected from methyl methacrylate, acrylonitrile and styrene.
  • the acrylic rubber resin may contain at least one functional group selected from the group consisting of hydroxyl group, carboxyl group and epoxy group.
  • the content ratio of the polycyclic aromatic ring-containing epoxy resin and acrylic rubber resin is about 1: 1.
  • the composition in embodiments is a polycyclic aromatic ring-containing epoxy resin, about 15 to 30 weight 0/0, and an acrylic rubber-based resin 30 to 45 parts by weight 0/0, and a curing agent 10 to 45% by weight, and the conductive particles of about 0.1 to 15 wt. May contain%.
  • the composition is a bisphenol epoxy, phenol novolac epoxy, s-cresol novolac epoxy, polyfunctional epoxy, amine epoxy, heterocyclic containing epoxy, substituted epoxy, It may further comprise one or more epoxy resins selected from naphtha-based epoxy and derivatives thereof.
  • the curing agent may include at least one of imidazole-based, isocyanate-based, amine-based, amide-based and acid anhydride-based curing agents.
  • the conductive particles are metal particles containing Au, Ag, Ni, Cu, Sn, Ti and Pb; Carbon particles; Particles coated with metal on the polymer resin; And the coated particle surface may include at least one of the insulated particles.
  • the composition may further comprise a silane coupling agent.
  • composition may include at least one additive including organic particles, inorganic particles, polymerization inhibitors, antioxidants, thermal stabilizers and light stabilizers.
  • the present invention provides an anisotropic conductive film formed by the composition. [Favorable effect]
  • the anisotropic conductive film formed by the composition of the present invention to complement the brittle properties of the epoxy resin in the high temperature and high humidity state to have the flexibility and layer resistance to prevent the anisotropic conductive film in the curing state to be broken. .
  • connection resistance can be lowered and the thermal stability part can be compensated for, and high reliability and high adhesion can be expressed.
  • the polycyclic aromatic ring-containing epoxy resin of the present invention is an epoxy resin in which two or more benzene rings are continuously bonded, and has a structure in which an epoxy group is substituted with a polycyclic benzenoid aromatic compound.
  • the polycyclic aromatic ring-containing epoxy resin is cured from an epoxy monomer having a structure of Formula 2 below. [Formula 2]
  • (Ar) n is a polycyclic aromatic hydrocarbon, n is 2-4 by the number of benzene rings, E is selected from an epoxy group, glycidyl group or glycidaloxy group, m is 1-3.
  • Examples of (Ar) n include naphthalene, anthracene and the like.
  • Preferred examples of naphthalene include E, an epoxy group, a glycidyl group glycidyloxy group, and the like, preferably a glycidyloxy group.
  • the epoxy monomer for preparing the polycyclic aromatic ring-containing epoxy resin may be 1,6-bis (2,3-epoxypropoxy) naphthalene or 1,5-bis (2,3-epoxypropoxy) Naphthalene, 2,2'-bis (2,3-epoxypropoxy) binaphthalene, and the like, and are not necessarily limited to this, as long as the glass transition temperature after curing is in the range of about 165 ° C to 220 ° C.
  • 1,6-bis (2,3-epoxypropoxy) naphthalene is preferable.
  • the glass transition temperature after curing of the polycyclic aromatic ring-containing epoxy resin has a range of about 165 ° C ⁇ 220 ° C., preferably about 180 ° C ⁇ 220 ° C.
  • the viscosity of the polycyclic aromatic ring-containing epoxy resin may be about 10,000 to 50,000 cps, preferably about 12,000 to 35,000 cps, and more preferably about 15,000 to 30,000 cps.
  • the acrylic rubber resin of the present invention has a repeating structure in which an acrylic ester is polymerized as shown in Chemical Formula 1, and the alkyl group of the side chain may be in a copolymer form of two or more kinds.
  • methyl methacrylate methyl metacrylate
  • acrylonitrile acrylonitrile
  • styrene styrene
  • R is an alkyl group having 1-20 carbon atoms.
  • Tg glass transition temperature
  • the acrylic rubber resin may include at least two d- 20 alkyl acrylates; And copolymers of at least one comonomer selected from methyl methacrylate, acrylonitrile and styrene.
  • comonomers selected from methyl methacrylate, acrylonitrile and styrene monomers are introduced, additional properties can be obtained while maintaining the basic adhesion and material miscibility of the acrylic rubber resin.
  • ⁇ is the glass jeonyieun degrees after curing of the final polymerized acrylic rubber-based resin it may be adjusted as needed, so that about 0 ° C to 20 ° C.
  • the acrylic rubber resin may have at least one functional group selected from the group consisting of a hydroxyl group, a carboxyl group and an epoxy group.
  • a hydroxyl group a carboxyl group
  • an epoxy group preferably it is an epoxy group containing acrylic copolymer.
  • the acrylic rubber resin of the present invention has a weight average molecular weight in the range of about 100,000 to about 1 million. Within the above range, the film may have excellent strength and adhesion. In addition, since it is excellent in compatibility with other resins, it is possible to have excellent connection reliability because a uniform crude liquid is possible. In the present invention, the glass transition temperature after curing of the acrylic rubber resin is about
  • Anisotropic conductive film is applied to a bisphenol-A type (BPA) type epoxy resin or a bisphenol-F type (BPF) type epoxy resin by applying a predetermined amount as a binder to an acrylic rubber resin having a low glass transition temperature (Tg) as described above. Make the properties very flexible. In addition, by bridging the brittle property, which is an inherent property of the epoxy resin, at high temperature and high humidity, the cured anisotropic conductive film can be combined with flexibility and layer resistance. Anisotropic conductivity according to the present invention.
  • the acrylic rubber resin becomes a matrix, and the polycyclic aromatic ring-containing epoxy resin is distributed in the entire domain.
  • the acryl rubber-based resin is a general composition (solid content) of about 30 to 45 weight 0/0, preferably from about 30 to 40% by weight of the weight.
  • the polycyclic aromatic ring-containing epoxy resin is an overall composition (solid content) of about 15 to 30 weight 0/0, preferably from about 15 to 20% increase of weight.
  • content of the sum of the aromatic ring-containing epoxy resin and the acrylic rubber-based resin is the total composition (solid content) of about 45 ⁇ 65 parts by weight 0/0 by weight, preferably from about 45 to 60 weight 0/0 Is preferably.
  • the content ratio of the polycyclic aromatic ring-containing epoxy resin and the acrylic rubber resin is about 1: 1, preferably about 1: 2 to 3.
  • composition for anisotropic conductive films which concerns on this invention may further contain a hardening
  • curing agent any epoxy curing type thermosetting agent known in the art may be used without limitation.
  • At least one selected from imidazole-based, isocyanate-based, amine-based, amide-based and acid anhydride-based may be used as the curing agent, but is not limited thereto.
  • the curing agent is about 10 to about 45% by weight, preferably about 15 to about
  • the anisotropic conductive film composition of this invention contains electroconductive particle in order to improve the electroconductive performance at the time of a circuit connection.
  • Such conductive particles may include metal particles including Au, Ag, Ni, Cu, Sn, Ti, and Pb; Carbon particles; Particles coated with a metal on the polymer resin; And the coated particle surface is at least one selected from insulated particles.
  • the carbon particles include carbon black, abyss, activated carbon, carbon whiskers, fullerenes, carbon nanotubes, and the like.
  • the polymer resin includes benzoguanamine, polyethylene, polypropylene, polyester, polystyrene, polyvinyl alcohol, and the like, but is not necessarily limited thereto. It may also include their modified resin.
  • Examples of the metal coating the polymer resin include Au, Ag, and Ni, but are not necessarily limited thereto.
  • the coated particles surface-insulated particles may include particles coated with the coated particles insulated particles.
  • the size of the said electroconductive particle can be selected and used according to a use in the range of about 0.1 to about 30 by the pitch of the circuit applied. Preferably from about 0.5 to about 15 / in. .
  • the conductive particles are used in the range of about 0.1 to 15% by weight based on the total composition (solid content).
  • the content of the conductive particles is less than about 0.1% increase does not appear to improve the conductivity, it can lead to insulation failure and if it exceeds about 15 wt. 0/0.
  • the composition for anisotropic conductive films according to the present invention may further include an epoxy resin.
  • the epoxy resins include bisphenol epoxy, phenol novolac epoxy, s-cresol novolac epoxy, polyfunctional epoxy, amine epoxy, heterocyclic containing epoxy, substituted epoxy, naph based It is preferably at least one selected from epoxy and derivatives thereof.
  • the epoxy resin is from about 30 parts by weight 0/0, preferably up to about 25% by weight of the total composition, more preferably it may be used up to about 20% by weight. In embodiments, the epoxy resin may be used at about 0 to about 15% by weight. In other embodiments, the epoxy resin may be used at about 1 to about 10 weight percent.
  • the anisotropic conductive film composition of the present invention without impairing the basic physical properties may further include about 0.01% to about 10% by weight. have.
  • silane coupling agent is 2- (3,4 epoxy cyclonuclear) -ethyltrimethoxysilane, 3-glycidoxytrimethyloxysilane containing epoxy,
  • the silane coupling agent may comprise about 0.1 to about 1 weight percent, more preferably about 1 to about 5 weight percent.
  • the polymerization inhibitor may be selected from the group consisting of hydroquinone monomethyl ether, P-benzoquinone, phenothiazine and mixtures thereof.
  • antioxidants such as branched phenolic or hydroxy cinnamate-based substances may be added for the purpose of preventing oxidation reaction and imparting thermal stability to the composition induced by heat. For example, tetrakis- (methylene -(3,5-di-t-butyl-4-hydrocinnamate) methane,
  • the anisotropic conductive film of this invention can be manufactured easily using the composition for anisotropic conductive films of this invention, without a special apparatus or installation. For example, after dissolving the composition of the present invention in an organic solvent such as toluene and liquefying, the composition is stirred for a predetermined time within a speed range in which the conductive particles are not pulverized, and the coating is applied to the release film at a thickness of about 10 to about 50. After drying for a predetermined time, a solvent such as toluene may be volatilized to obtain an anisotropic conductive film.
  • an organic solvent such as toluene
  • the anisotropic conductive film of the present invention after 500 hours at 85 ° C, 85 RH conditions
  • the resistance measured by ASTM F 3-64T may be about 2 to about 8 ⁇ .
  • composition obtained by mixing each component as shown in Table 1 below was applied on a release film, and dried for 5 minutes at a temperature of 80 ° C. using an oven to obtain an anisotropic conductive film of thickness 35, width 1.5mm.
  • (A) Polycyclic aromatic-containing epoxy resin Naphthalene epoxy resin (product name: HP4032D) manufactured by Japan Ink Chemical Co., Ltd. having a glass transition temperature of 220 ° C. after curing was used.
  • Acrylic rubber resin An acrylate copolymer (product name: SG-P3-TEA) manufactured by Nagase Camtex having a glass transition temperature of 15 ° C. was used.
  • Curing agent A microcapsule-type imidazole (product name: HX3941HP) manufactured by Asahi Kasei was used.
  • Epoxy Resin A BPA epoxy resin (product name: EXA850CRP) manufactured by Nippon Ink Chemical Co., Ltd. was used.
  • Silane coupling agent The epoxy silane (product name: KBM403) manufactured by Shin-Yetsu was used. Property and Reliability Evaluation
  • the temperature is measured using four types of FPCB (Adhesive type 1, Adhesive type 2, Adhesive-less type 1, Adhesive-less type 2) as shown in the following ⁇ Table 2>.
  • Adhesive type 1 Adhesive type 2
  • Adhesive-less type 1 Adhesive-less type 2
  • the occurrence of bubbles was measured by an optical microscope. If the electrode length is a Bubble length is within X "measured in the 800 ⁇ reference ⁇ , 20 (> is within m O, it is within 30O m ⁇ , 40 (> m or more was evaluated as X.
  • the measurement results are shown in Table 2 It was.
  • anisotropic conductive films prepared in Examples and Comparative Examples were connected using a panel with a ⁇ pattern and FPCB at 190 ° C., 10 seconds, and 3 MPadml main compression conditions, and 90 ° adhesive force was measured (ASTM D3330 / D3330M).
  • the connection resistance ASTM F43-64T was measured after 250 hours and after 500 hours, respectively, and the results are shown in Table 3.
  • Table 3 As shown in the results of Table 2 and Table 3, when applied to the adhesive-less type FPCB using an anisotropic conductive film having the same content ratios as Examples 1 to 4, almost no bubbles were generated, showing high reliability. You can check it.
  • the examples show a low resistance value and a high adhesive strength when compared to the comparative examples, it can be seen that the reliability, adhesion, etc. all improved compared to the comparative example. Simple modifications and variations of the present invention can be easily made by those skilled in the art, and all such modifications or changes can be seen to be included in the scope of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Non-Insulated Conductors (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition pour film conducteur anisotrope, comprenant : une résine époxy contenant des noyaux aromatiques polycycliques ; une résine à base de caoutchouc acrylique ; des particules conductrices ; et un durcisseur. Après le durcissement, la résine époxy contenant des noyaux aromatiques polycycliques présente une température de transition vitreuse (Tg) de 165 °C à 220 °C, la résine à base de caoutchouc acrylique présente une Tg de 0 °C à 20 °C, et la teneur combinée de la résine époxy contenant des noyaux aromatiques polycycliques et de la résine à base de caoutchouc acrylique est de 45 à 65 % en poids du pourcentage pondéral total de la composition (partie solide). La composition pour un film conducteur anisotrope présente non seulement une flexibilité et une résistance aux impacts pour compenser la propriété cassante de la résine époxy dans des conditions de température et humidité élevées pour empêcher un film conducteur anisotrope durci de se fissurer, mais peut également diminuer la résistance au raccordement et augmenter la stabilité thermique de manière à présenter une fiabilité et une adhésivité de grande importance.
PCT/KR2010/004720 2009-08-20 2010-07-20 Composition pour film conducteur anisotrope Ceased WO2011021780A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2009-0077079 2009-08-20
KR1020090077079A KR101138799B1 (ko) 2009-08-20 2009-08-20 이방 도전성 필름용 조성물

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WO2011021780A2 true WO2011021780A2 (fr) 2011-02-24
WO2011021780A3 WO2011021780A3 (fr) 2011-05-19

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CN (1) CN101993575B (fr)
TW (1) TWI423267B (fr)
WO (1) WO2011021780A2 (fr)

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KR101464353B1 (ko) 2011-12-28 2014-11-25 제일모직 주식회사 이방 도전성 필름용 조성물, 이방 도전성 필름, 및 이를 이용한 반도체 장치
KR101365107B1 (ko) * 2012-09-21 2014-02-20 제일모직주식회사 이방성 도전 필름 및 이를 포함하는 반도체 장치
JP6180159B2 (ja) * 2013-04-04 2017-08-16 デクセリアルズ株式会社 異方性導電フィルム、接続方法、及び接合体
CN104250525B (zh) * 2013-06-25 2016-04-20 第一毛织株式会社 各向异性导电膜、图像显示器及半导体装置

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Also Published As

Publication number Publication date
CN101993575A (zh) 2011-03-30
CN101993575B (zh) 2013-03-27
TW201108253A (en) 2011-03-01
KR101138799B1 (ko) 2012-04-24
WO2011021780A3 (fr) 2011-05-19
TWI423267B (zh) 2014-01-11
KR20110019519A (ko) 2011-02-28

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