WO2020093556A1 - Adhésif conducteur anisotrope et film conducteur associé - Google Patents

Adhésif conducteur anisotrope et film conducteur associé Download PDF

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Publication number
WO2020093556A1
WO2020093556A1 PCT/CN2018/123004 CN2018123004W WO2020093556A1 WO 2020093556 A1 WO2020093556 A1 WO 2020093556A1 CN 2018123004 W CN2018123004 W CN 2018123004W WO 2020093556 A1 WO2020093556 A1 WO 2020093556A1
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WO
WIPO (PCT)
Prior art keywords
conductive adhesive
anisotropic conductive
acrylate
resin
silane
Prior art date
Application number
PCT/CN2018/123004
Other languages
English (en)
Chinese (zh)
Inventor
孙作榜
张霞
王海军
李泳锐
Original Assignee
深圳市华星光电技术有限公司
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Filing date
Publication date
Application filed by 深圳市华星光电技术有限公司 filed Critical 深圳市华星光电技术有限公司
Publication of WO2020093556A1 publication Critical patent/WO2020093556A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C09J171/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/314—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive layer and/or the carrier being conductive

Definitions

  • the present invention relates to the field of semiconductor technology, and in particular, to a conductive adhesive and its conductive film for electrical connection between semiconductor electronic components.
  • the conductive adhesive has high adhesion and reliability, but also to accurately turn on the micro circuit, especially to realize the anisotropic conduction of the micro circuit, such as the vertical conduction of the upper and lower circuits, and the horizontal guarantee of insulation , That is, anisotropic conductive adhesive.
  • the application process in addition to improving the performance of the conductive adhesive itself, the application process must also be able to meet the requirements of the production process.
  • the most important point is that the anisotropic conductive adhesive needs to cure in a very short time, usually less than 15s, to complete the bonding of the circuit board, thereby improving production efficiency and increasing output.
  • the anisotropic conductive adhesives commonly used in the industry can be divided into two major categories from the main components: the first category is a system of thermosetting epoxy resin mixed with conductive gold balls; the second category is a thermosetting acrylic resin Mixed conductive gold ball system.
  • the curing time is too long, and the curing temperature is too high, these two problems are particularly prominent for the anisotropic conductive adhesive of the epoxy system;
  • the bonding strength is not enough. It is not enough to just increase the degree of adhesion inside the glue. It is also necessary to consider how to increase the adhesion at the interface of the glued substrate;
  • One aspect of the present invention is to provide an anisotropic conductive adhesive with a fast reaction speed and a short curing time.
  • An anisotropic conductive adhesive (ACF) based on a thermally cured acrylate system.
  • the acrylate system includes the following components in mass ratio: 5% to 40% of acrylate monomer, 0.5 to 10% of free radical initiator, 5% to 40% of film-forming resin, 5% to 40 % Rubber with carboxyl group or hydroxyl group, 0.1 ⁇ 5% silane coupling agent, 0.1 ⁇ 5% anti-aging agent, 1% ⁇ 10% conductive ball and remaining solvent.
  • the acrylate monomers include methyl acrylate, methyl methacrylate, isobutyl acrylate, bisphenol A epoxy acrylate, ethyl acrylate, ethylene glycol diacrylate Combination of monofunctional groups, difunctional groups and multifunctional groups such as esters, trifluoroethyl methacrylate, ethoxy diethylene glycol acrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, Wherein the monofunctional and bifunctional acrylate monomers account for the main part, and the multifunctional acrylate monomers are the accessory part to increase the degree of crosslinking.
  • the acrylate monomer includes one of methyl methacrylate, ethylene glycol diacrylate, and pentaerythritol triacrylate.
  • the conductive spheres include polystyrene beads modified with carbon nanotubes, the surface of which is uniformly coated with the carbon nanotubes.
  • the organic peroxide can exist stably under normal temperature and low temperature conditions below 60 ° C without decomposing into free radicals; and At 120 °C -150 °C, it will quickly decompose into free radicals.
  • the peroxide includes methylcyclohexanone peroxide, dibenzoyl peroxide, t-butyl toluene peroxide, t-butyl peroxybenzoate, and laurel peroxide
  • dibenzoyl peroxide and lauroyl peroxide are preferred, but not limited to.
  • the film-forming resin includes phenoxy resin, urea resin, polyimide resin, polyvinyl methylal, xylene resin, polyamide resin, polyester resin, and poly One of ethylene butyral, and the molecular weight of the selected resin is between 10,000 and 100,000.
  • the selected resin can contain more hydroxyl groups or carboxyl groups, it is more suitable, which is conducive to improving the adhesion of the adhesive; at the same time, the selected resin must have sufficient heat resistance, when the temperature changes, it has more Small volume change rate. Phenoxy resins with molecular weights between 20,000 and 60,000 are preferred here.
  • the performance parameter requirement is that the molecular weight is between 100000-1000000, Glass transition temperature Tg ⁇ 0 ° C.
  • the more hydroxyl group / carboxyl group content in the selected rubber is better, which is beneficial to increase the adhesion; in addition, the acid value can be preferentially selected according to the acid value> 10mgKOH / g rubber.
  • the ratio of the carboxyl group / hydroxyl group-containing rubber to the phenoxy resin in the film-forming resin is preferably 1: 1, but it is not limited thereto.
  • the silane coupling agent includes vinyl silane, amino silane, methacryloxy silane, A151 (vinyl triethoxy silane), A171 (vinyl trimethoxy) Silane), A172 (vinyl tri ( ⁇ -methoxyethoxy) silane), 2,3 epoxypropyl propyl trimethoxy silane, amino functional group tri methoxy silane and (3-aminopropyl) tri One of ethoxysilane. Specifically, it is preferably (3-aminopropyl) triethoxysilane, but is not limited thereto.
  • the anti-aging stabilizer includes one of amines, phenols, sulfides, and phosphites.
  • an amine anti-aging agent is preferred, which may be N-phenyl-2-naphthylamine, but is not limited thereto.
  • the main selection principle is to have good solubility in the polymer resin and rubber used, which includes methyl ethyl ketone, n-butyl glycidyl ether, toluene and dichloromethane One of methane.
  • it is preferably an epoxy-containing n-butyl glycidyl ether, because it has an epoxy group, and the residual solvent can also react with the system to solidify.
  • another aspect of the present invention is to provide a conductive film, which includes a release film.
  • the anisotropic conductive adhesive according to the present invention is attached to the release film.
  • Another aspect of the present invention is to provide a method for preparing the conductive film according to the present invention, including the following steps:
  • the film-forming resin is dispersed into the solvent at a predetermined concentration, and then the silane coupling agent, anti-aging agent, rubber, and acrylate monomer are sequentially added at a predetermined ratio to perform the steps of mixing, stirring, and defoaming To get pre-mixed rubber material;
  • a predetermined amount of the free radical initiator is added to perform the rubber-mixing, stirring and defoaming steps to obtain a medium-mixed rubber material;
  • the final mixed rubber material is coated on a release film with a thickness of 10 to 100 um and dried, to obtain the anisotropic conductive film according to the present invention.
  • the material of the release film includes one of PET, PTFT, or a composite film material.
  • the coating method of the final mixed glue material includes one of film forming methods such as knife coating, spin coating, and screen printing.
  • the drying treatment method is to heat it at 50 to 100 ° C. for 3 min to 15 min, or use an infrared lamp drying process; the specific may be determined according to actual needs and is not limited.
  • the invention relates to an anisotropic conductive adhesive, which adopts free radical polymerized acrylate system, which has fast reaction speed and short curing time. Further, by incorporating carboxyl-terminated nitrile rubber and acrylic rubber into the acrylate system, the adhesive force at the bonding interface is increased, thereby greatly improving the bonding strength.
  • FIG. 1 is a schematic layout diagram of a test structure for testing the conduction resistance and insulation resistance of an anisotropic conductive adhesive according to the present invention.
  • An embodiment of the present invention provides an anisotropic conductive adhesive, which is mainly based on a thermally cured acrylate system, which contains at least (A) acrylate monomer, (B) free radical initiator, (C) Film-forming resin, (D) rubber with carboxyl or hydroxyl groups, (E) silane-based coupling agent, (F) anti-aging agent, (G) carbon nanotube modified polystyrene beads, and (H ) Solvent.
  • A acrylate monomer
  • B free radical initiator
  • C Film-forming resin
  • D rubber with carboxyl or hydroxyl groups
  • E silane-based coupling agent
  • F anti-aging agent
  • G carbon nanotube modified polystyrene beads
  • H Solvent
  • the added mass ratio is 5% to 40%.
  • monofunctional groups, difunctional groups and multifunctional groups such as diethylene glycol esters, pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, etc., where monofunctional and bifunctional acrylate monomers account for The main part, the multifunctional acrylate monomer accounts for a small part, which is used to increase the degree of crosslinking.
  • one of methyl methacrylate, ethylene glycol diacrylate, and pentaerythritol triacrylate is preferred.
  • the mass ratio is 0.5 to 10%.
  • the main choices are organic peroxides, such as methylcyclohexanone peroxide, dibenzoyl peroxide, t-butyl toluene peroxide, t-butyl peroxybenzoate, lauroyl peroxide, stearoyl peroxide and many more.
  • the main selection principle is that the peroxide can exist stably under normal temperature and low temperature conditions, and will not decompose into free radicals, but will decompose into free radicals rapidly under high temperature (120 °C -150 °C).
  • one of dibenzoyl peroxide and lauroyl peroxide is preferably selected.
  • the (C) film-forming resin a mass ratio of 5% to 40% is added.
  • the molecular weight of these resins is preferably located at 10000 -100000. If the selected resin can contain more hydroxyl groups or carboxyl groups, it is more suitable, which is conducive to improving the adhesion of the adhesive; at the same time, the selected resin must have sufficient heat resistance and a small temperature change For volume change rate, phenoxy resin with molecular weight between 20,000 and 60,000 is preferred here.
  • the mass ratio is 5% to 40%.
  • acrylic rubber with carboxyl groups / hydroxyl groups and / or nitrile rubber with carboxyl groups at the ends can be selected.
  • the performance parameters are required to have a molecular weight between 100000-1000000 and a glass transition temperature Tg ⁇ 0 ° C.
  • the acid value can be selected preferentially> 10mgKOH / g rubber.
  • the preferred ratio of the rubber with carboxyl groups / hydroxyl groups to the phenoxy resin is 1: 1.
  • the (E) silane-based coupling agent a mass ratio of 0.1 to 5% is added.
  • (F) anti-aging stabilizer add a mass ratio of 0.1 to 5%.
  • amines, phenols, sulfides, phosphites, etc. can be selected, and amine anti-aging agents are preferred here.
  • N-phenyl-2-naphthylamine is used in this patent.
  • (G) carbon nanotube modified polystyrene beads the mass ratio is 1% to 10%.
  • the surface of the polystyrene beads is uniformly coated with carbon nanotubes, and then by adjusting the particle size of the polystyrene beads, conductive beads with different particle diameters can be prepared, thereby making full use of the carbon nanotubes. Conductivity greatly reduces costs.
  • the (H) solvent it is the balance.
  • the main selection principle is to have good solubility in the polymer resin and rubber used.
  • methyl ethyl ketone, n-butyl glycidyl ether, toluene, and methylene chloride can be used.
  • N-butyl glycidyl ether with epoxy groups is preferred here, because it has epoxy groups, and the residual solvent can also react with the system to solidify.
  • another aspect of the present invention is to provide a conductive film, which includes a release film.
  • the anisotropic conductive adhesive according to the present invention is attached to the release film.
  • Another embodiment of the present invention provides a method for preparing the conductive film according to the present invention, which includes the following steps:
  • Step1 Firstly disperse the selected predetermined amount of phenoxy resin in the solvent at a predetermined concentration, and then add the silane coupling agent, anti-aging agent, rubber and acrylate monomers in a predetermined ratio in order to mix the glue , Mixing and defoaming processes to obtain pre-mixed rubber materials; wait for the pre-mixed rubber materials to cool, then add the free radical initiator, intermittent, multiple times of mixing, stirring and de-foaming processes, for example, parameter settings It can be 2000 rpm, pressure adjusted to 30Kpa and time 1min, homogenization operation, after cooling, recirculation 3 times, control the homogenization temperature ⁇ 40 °C; and then the carbon nanotube modified polystyrene beads (CNT Ball) is dispersed in the mixed rubber material at a predetermined ratio, and the mixing, stirring and defoaming processes are performed again to ensure full mixing.
  • the free radical initiator intermittent, multiple times of mixing, stirring and de-foaming processes
  • Step2 Apply the defoamed glue from step 1 on the 10 ⁇ 100um thick release film, and apply and dry it.
  • the release film can be made of PET, PTFT or its composite film, and can be processed.
  • the coating can be formed by scraping, spin coating, screen printing and other processes, and the drying can be heated at 50 ⁇ 100 °C for 3min ⁇ 15min, or using infrared lamp drying process.
  • Step3 Cut the large ACF film produced in step 2 to obtain ACF films of different widths, such as 1.2mm width, as required.
  • the test method of the above-mentioned adhesive strength is that the anisotropic conductive adhesive film in each embodiment column in the above list is attached to the connection point of the PCBA circuit board, the conductive film length is 42mm, the width is 2mm, Press (pressure 0.3 Mpa, temperature 120 °C, time 2s), tear off the release film (PET material), paste COF on it, and then pass this pressure (pressure 0.3 Mpa, temperature 180 °C, time 10s)
  • Press pressure 0.3 Mpa, temperature 120 °C, time 2s
  • PET material tear off the release film
  • paste COF paste COF on it
  • For sample preparation use a tensile machine, perpendicular to the PCBA board, and pull the COF upward at 90 degrees to determine the bonding strength.
  • the phenoxy resin + nitrile rubber system has a hard texture, and the adhesion during pre-pressing is too weak, which is not conducive to the alignment of PCBA and COF, while the phenoxy resin + acrylic rubber system When slightly melted and softened, it has a certain adhesion, which is conducive to the alignment of PCBA and COF and achieves preliminary adhesion. From this aspect, the performance of acrylic rubber is better than that of nitrile rubber.
  • the resistance of the nitrile rubber system is higher than that of the acrylic rubber system. From this aspect, the performance of the acrylic rubber is better than that of the nitrile rubber. Furthermore, the selected carbon nanotube spheres have excellent conductivity, and the density can be controlled by choosing an appropriate ratio to achieve anisotropic conductivity, which has excellent reliability and can completely replace expensive gold spheres.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Non-Insulated Conductors (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un adhésif conducteur anisotrope et un film conducteur associé. L'adhésif conducteur utilise un système d'acrylate thermodurcissable en tant que base, et comprend un monomère acrylate, un initiateur radicalaire, une résine filmogène, un caoutchouc contenant un groupe carboxyle ou hydroxy, un agent de couplage au silane, un agent anti-vieillissement, des billes de polystyrène modifiées par un nanotube de carbone et un solvant. La présente invention concerne un adhésif conducteur anisotrope ayant une vitesse de réaction élevée et un temps de solidification court.
PCT/CN2018/123004 2018-11-09 2018-12-24 Adhésif conducteur anisotrope et film conducteur associé WO2020093556A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201811328083.1 2018-11-09
CN201811328083.1A CN109628049A (zh) 2018-11-09 2018-11-09 一种各向异性导电胶黏剂及其导电膜

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WO2020093556A1 true WO2020093556A1 (fr) 2020-05-14

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CN112310266A (zh) * 2020-10-23 2021-02-02 深圳市华星光电半导体显示技术有限公司 Led芯片的固晶方法及led面板

Citations (3)

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JP2013229240A (ja) * 2012-04-26 2013-11-07 Hitachi Chemical Co Ltd 導電性粒子及びその製造方法
CN104046315A (zh) * 2014-06-11 2014-09-17 深圳职业技术学院 紫外光双重固化导电胶黏剂及其制备方法
CN104342058A (zh) * 2014-10-25 2015-02-11 深圳市飞世尔实业有限公司 一种光固化异方性导电膜及其制备方法

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Publication number Priority date Publication date Assignee Title
CN102634286B (zh) * 2012-05-17 2013-08-14 深圳市飞世尔实业有限公司 一种光热双重固化型异方性导电膜的制备方法
CN105585728B (zh) * 2015-11-26 2018-11-06 中国科学院金属研究所 一种碳纳米管包覆聚合物微球的方法
CN107418469A (zh) * 2017-05-26 2017-12-01 深圳市华星光电技术有限公司 一种碳纳米管导电球及其制备方法和应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013229240A (ja) * 2012-04-26 2013-11-07 Hitachi Chemical Co Ltd 導電性粒子及びその製造方法
CN104046315A (zh) * 2014-06-11 2014-09-17 深圳职业技术学院 紫外光双重固化导电胶黏剂及其制备方法
CN104342058A (zh) * 2014-10-25 2015-02-11 深圳市飞世尔实业有限公司 一种光固化异方性导电膜及其制备方法

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