CN114927256A - Circuit connecting material - Google Patents
Circuit connecting material Download PDFInfo
- Publication number
- CN114927256A CN114927256A CN202210473835.3A CN202210473835A CN114927256A CN 114927256 A CN114927256 A CN 114927256A CN 202210473835 A CN202210473835 A CN 202210473835A CN 114927256 A CN114927256 A CN 114927256A
- Authority
- CN
- China
- Prior art keywords
- acrylate
- connecting material
- meth
- circuit
- nitroso
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Dispersion Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a circuit connecting material, and relates to the technical field of electrical elements; the circuit connecting material includes a radical polymerization resin, a polymerization initiator, a nitroso-containing compound, and conductive particles. The circuit connecting material provided by the invention has good electrical connection performance and adhesive force, and meanwhile, has wider process margin and avoids poor connection through the synergistic effect of the nitroso-containing compound and the free radical polymerization resin.
Description
Technical Field
The invention relates to the technical field of electrical elements, in particular to a circuit connecting material.
Background
Thermosetting epoxy resins having high adhesiveness and high reliability have been generally used for a long time as circuit connecting materials for semiconductor elements and liquid crystal display elements. In the bonding process, the circuit connecting material is generally required to be cured within 5 to 20 seconds at a temperature of 170 to 250 ℃, so that the desired electrical connection and bonding strength between the circuits are obtained.
However, with the recent progress of high integration of semiconductor elements and high definition of liquid crystal elements, the pitches between elements and between wirings have been gradually narrowed, and heating at the time of curing of circuit connecting materials has had some adverse effects on peripheral parts. Further, since the electrode width and the electrode interval are extremely narrow and the electrode height is also low, there are problems that the use of the conventional circuit connecting material causes positional deviation of wiring and the like; further, since it is necessary to shorten the process time for cost reduction, there is a strong demand for a circuit connecting material that can be cured and bonded at a relatively low temperature in a short time.
As a method for achieving low-temperature and short-time curing, a radical type adhesive using a radical polymerizable resin such as an acrylate derivative or a methacrylate derivative (hereinafter referred to as a (meth) acrylate derivative) and a peroxide as a radical polymerization initiator in combination has been attracting attention. In radical curing, radicals in reaction have high reactivity, and thus low-temperature short-time curing can be achieved. However, since the adhesive cured using a radical has a narrow process margin due to its high reactivity, and due to the deviation of the curing temperature and curing time, the radical polymerization resin is already cured before the conductive particles are electrically connected, which may cause a poor circuit connection.
A super-narrow-pitch circuit having a wiring pitch of 40 μm or less, such as cof (chip On flex) used as a wiring material for a large television, has been put to practical use. Since COF is a film formed by forming an electrode on a polyimide film, polyimide expands and contracts depending on the ambient temperature and humidity during use or the curing temperature during connection, and the wiring pitch changes slightly depending on the use conditions. In contrast, since the pitch of the wires formed on the corresponding LCD glass is almost unchanged, when the wires are connected by applying heat and pressure, the corresponding wires may have a pitch mismatch, resulting in a connection failure. In order to avoid this problem, there is a technique of designing a COF at a pitch smaller than a predetermined specification, applying radiant heat to the COF by a hot tool of a connecting device to thermally expand the COF, forcibly adjusting the COF to the pitch on the LCD glass side, and then applying pressure to the COF to press the COF. However, since the pushing speed of the heating tool is 0.3mm/sec or less and the pushing speed is extremely slow in this process technology, a radical polymerizable resin is hardened by radiant heat before electrical connection between COF and an electrode of LCD glass, and a connection failure occurs.
Further, since curing shrinkage at the time of radical curing is large, adhesion strength is inferior, particularly adhesion strength to a base material made of an inorganic material or a metal material is low, as compared with the case of using an epoxy resin; as a method for improving the adhesive strength, a method of improving the adhesive strength of the surface of an inorganic substance such as a metal by using a radical polymerizable substance having a phosphate structure; however, when a radical polymerizable substance having a phosphate structure is used alone, the metal plating layer of the conductive particles themselves also reacts to generate free radicals by redox action, resulting in a decrease in storage stability.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the invention provides a circuit connecting material, aiming at solving the problem that poor circuit connection is easy to occur due to narrow process allowance of a bonding material hardened by free radicals in the prior art, the circuit connecting material can be rapidly cured at low temperature and in short time through the synergistic action of a free radical polymerization resin, a nitroso-containing compound, an initiator and the like, has larger process allowance during the hardening treatment, higher bonding strength to a circuit base material and good storage stability and reliability at room temperature, and solves the problem that poor circuit connection is easy to occur due to narrow process allowance of the bonding material hardened by the free radicals in the prior art.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a circuit connecting material includes a radical polymerization resin, a polymerization initiator, a nitroso-containing compound, and conductive particles.
Optionally, the nitroso-containing compound is an aromatic nitroso compound.
Optionally, the nitroso-containing compound is selected from at least one of N-nitrosophenylhydroxylamine aluminum and N-nitrosophenylhydroxylamine ammonium.
Optionally, the mass fraction of the nitroso-containing compound is 0.01-3%.
Optionally, the species of the radical polymerization resin are two or more; the two or more free radical polymerization resins include a phosphate compound having an acrylate group or a methacrylate group in a molecule and a compound having at least two acrylate groups or methacrylate groups in a molecule.
Alternatively, the structural formula of the phosphate ester compound having an acrylate group or a methacrylate group in the molecule is shown in the following formulas (2) to (4):
wherein R is 1 、R 3 、R 5 Are both acrylate or methacrylate groups, R 2 、R 4 Are each hydrogen or methyl, and Y, Z, W, X, L, M are each an integer of 1 to 8.
Optionally, the mass fraction of the phosphate ester compound having an acrylate group or a methacrylate group in a molecule is 0.1% to 5%.
Alternatively, the compound having at least two acrylate groups or methacrylate groups in a molecule is selected from at least one of epoxy (meth) acrylate oligomer, urethane (meth) acrylate oligomer, polyether (meth) acrylate oligomer, polyester (meth) acrylate oligomer, trimethylolpropane tri (meth) acrylate, polyethylene glycol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, neopentyl glycol di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bis (2-acryloyloxyethyl) isocyanurate, and tris (2-acryloyloxyethyl) isocyanurate.
Optionally, the polymerization initiator is selected from at least one of diacyl peroxides, alkyl peresters, peroxyketals, peroxyesters, and peroxycarbonates.
Optionally, the mass fraction of the polymerization initiator is 0.1% to 10%.
The beneficial effects of the invention are: the circuit connecting material provided by the invention has good electrical connection performance and adhesive force, and meanwhile, has wider process margin and avoids poor connection through the synergistic effect of the nitroso-containing compound and the free radical polymerization resin.
Detailed Description
The present invention will now be described in further detail. The embodiments described below are intended to be illustrative of the invention and should not be understood as limiting the invention, and all other embodiments that can be made by one skilled in the art without inventive effort based on the embodiments of the invention shall fall within the scope of protection of the invention.
In order to solve the problem that poor circuit connection is easy to occur due to narrow process margin of a bonding material hardened by free radicals in the prior art, the invention provides a circuit connection material which comprises free radical polymerization resin, a polymerization initiator, a nitroso-containing compound and conductive particles.
The preferred polymerization initiator of the present invention is a radical polymerization initiator which generates free radicals by heat; since the nitroso group can trap a radical, on the one hand, the storage stability of the circuit connecting material is remarkably improved by the nitroso-containing compound, and on the other hand, the reaction caused by radiant heat of the heating tool is suppressed, thereby improving the process margin.
As a typical example, the present invention shows the reaction mechanism of N-nitroso-N-phenylhydroxylamine aluminum in the following reaction formula:
as shown in the formula, nitroso capture free radical Y is generated firstly, and the nitroso capture free radical Y reacts with acrylic monomers to form a stable coupling product secondly; since the N-N cleavage of the coupling product tends to proceed at temperatures above 50 ℃, it becomes tri-c at the time of ligation; and the third step reacts with two free radicals to form the fourth step.
Further, the problem that free radicals are generated by the redox action of the phosphate compound and the metal plating reaction of the conductive particles, and the storage stability is lowered, is solved by the nitroso compound, which can prevent the deterioration of the storage stability by trapping the free radicals.
The present invention can prevent the problem that the radical polymerizable resin is hardened by radiant heat before the COF is crimped even if the heating tool moves slowly in the COF connection of a large television by adding the compound having a nitroso group. This effect can be confirmed not only by actually slowing down the hot tool speed but also by the change in the reaction start temperature of the DSC.
The invention forms an adhesive film with conductive performance by free radical polymerization resin, polymerization initiator and conductive particles; the thermal hardening speed of the adhesive film is adjusted by introducing the nitroso-containing compound, so that the hardening speed of the adhesive film is matched with the operating parameters in the bonding process, the free radical polymerization resin is prevented from hardening before electric connection is realized in the process of connecting the substrates, and poor connection can be avoided.
The circuit connecting material provided by the invention has good electrical connection performance and adhesive force, wide process margin, poor connection avoidance and good storage stability by the synergistic effect of the nitroso-containing compound and the free radical polymerization resin.
Preferred nitroso-containing compounds of the present invention have the formula (1):
wherein R is aryl, L is an integer of 1-3, and M is cation or ammonium salt with a valence of L.
The heating of the aliphatic nitroso compound can stabilize the combination of N-NO, and the combination cutting requires light; on the other hand, the aromatic nitroso compound is preferably an aromatic nitroso compound because it is heated to cause radical cleavage of an N — NO bond, particularly an aryl group having a large steric hindrance, and is likely to explosively cause radical cleavage at a temperature of 50 ℃ or higher, thereby suppressing a reaction caused by radiant heat of a heating tool; specifically, the nitroso-containing compound of the present invention is preferably at least one compound selected from the group consisting of aluminum N-nitrosophenylhydroxylamine and ammonium N-nitrosophenylhydroxylamine.
The comprehensive performance of the circuit connecting material is improved by adding the aromatic nitroso compound and the free radical polymerization resin to perform synergistic action.
In order to ensure the connection effect of the circuit connection material, the circuit connection material is further optimized to contain 0.01 to 3 percent of nitroso compound; that is, when the total amount of the nitroso-containing compound is 100phr, the amount of the nitroso-containing compound is 0.01 to 3.00phr, on one hand, the problem that when the amount of the nitroso-containing compound is less than 0.01phr, the amount of the nitroso-containing compound is insufficient, the hardening speed cannot be effectively adjusted, and the process margin is narrow is avoided; on the other hand, when the amount of the nitroso-containing compound is more than 3phr, the radical polymerization resin does not react sufficiently during the bonding process, thereby causing poor bonding.
The free radical polymerization resin in the invention can be any free radical polymerization resin in the prior art; in order to realize low-temperature short-time hardening of the circuit connecting material, the application preferably selects more than two kinds of free radical polymerization resins; the two or more free radical polymerization resins comprise a phosphate compound with an acrylate group or a methacrylate group in a molecule and a compound with at least two acrylate groups or methacrylate groups in a molecule; that is, one of the two or more radical polymerization resins is a phosphate compound having an acrylate group in the molecule or a phosphate compound having a methacrylate group in the molecule; also, there is a compound having at least two acrylate groups in a molecule, or a compound having at least two methacrylate groups in a molecule.
Specifically, the structural formula of the phosphate ester compound having an acrylate group or a methacrylate group in the molecule is shown in the following formulas (2) to (4):
wherein R is 1 、R 3 、R 5 Are both acrylate or methacrylate groups, R 2 、R 4 Are each hydrogen or methyl, and Y, Z, W, X, L, M are each an integer of 1 to 8.
Specifically, the phosphate ester compound having an acrylate group or a methacrylate group in a molecule is preferably at least one selected from the group consisting of acidic phosphoric acid (meth) acrylate, acidic oxypolyoxyethylene glycol monomethacrylate, acidic oxypolyoxypropylene glycol monomethacrylate, diethyl 2,2' -di (meth) acryloyloxy phosphate, EO-modified dimethacrylate phosphate, and phosphoric acid-modified epoxy acrylate; and further preferably the mass fraction of the phosphate compound having an acrylate group or a methacrylate group in the molecule is 0.1% to 5%; that is, when the total blending part is 100phr, the bonding strength between the circuit connecting material and the surface of inorganic matter such as metal is improved by using 0.1-5 phr of phosphate compound with acrylate group or methacrylate group in the molecule; when the content is less than 0.1phr, it may be difficult to obtain a high adhesive strength, and when it exceeds 5phr, since the phosphate ester compound having an acrylate group or a methacrylate group in the molecule is a highly acidic substance, corrosion of a circuit electrode may be accelerated after connection, and reliability of conduction may be lowered.
Another type of radical polymerizable resin having at least two acrylate groups or methacrylate groups in a molecule can use well-known compounds without particular limitation; it is preferable in the present invention that the compound having at least two acrylate groups or methacrylate groups in the molecule is at least one selected from the group consisting of epoxy (meth) acrylate oligomer, urethane (meth) acrylate oligomer, polyether (meth) acrylate oligomer, polyester (meth) acrylate oligomer, trimethylolpropane tri (meth) acrylate, polyethylene glycol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, neopentyl glycol di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bis (2-acryloyloxyethyl) isocyanurate, and tris (2-acryloyloxyethyl) isocyanurate; in particular, a solid urethane (meth) acrylate oligomer is suitable for use at room temperature because it has high adhesion to a substrate such as polyimide and also has excellent film formability.
In order to ensure the stability, reactivity and compatibility of the circuit connecting material, it is preferable that the polymerization initiator is at least one selected from the group consisting of diacyl peroxides, alkyl peresters, peroxyketals, peroxyesters and peroxycarbonates.
Specifically, the temperature range of the 1-minute half-life period of the polymerization initiator is preferably 90-160 ℃; so as to prevent the storage stability of the circuit connecting material from being reduced when the temperature of the half-life period of 1 minute is lower than 90 ℃, and faults caused by the reaction of the circuit connecting material caused by the difference of environmental temperature in the storage process or engineering use; if the 1 minute half-life temperature is higher than 160 deg.c, it is difficult for the circuit connecting material to achieve connection in a short time, for example, 10 seconds.
The mass fraction of the polymerization initiator in the circuit connecting material is preferably 0.1-10 percent; that is, when the total amount of addition is 100phr, the amount of addition of the polymerization initiator is 0.1 to 10phr so as not to cause insufficient curing of the circuit connecting material when the amount of addition is less than 0.1 phr; addition of more than 10phr of component results in a decrease in process margin.
Preferred polymerization initiators for the present invention are selected from the group consisting of bis (3,5, 5-trimethylhexanoyl) peroxide (1 minute half-life temperature 112 ℃), dilauroyl peroxide (1 minute half-life temperature 116 ℃), disuccinic acid peroxide (1 minute half-life temperature 131 ℃), bis (3-methylbenzoyl) peroxide (1 minute half-life temperature 131 ℃), benzoyl peroxide (3-methylbenzoyl) peroxide (1 minute half-life temperature 130 ℃), 2, 5-dimethyl-2, 5-bis (2-ethylhexanoyl peroxide) hexane (1 minute half-life temperature 118 ℃), bis (2-ethylhexyl) peroxydicarbonate (1 minute half-life temperature 90 ℃), 1, 3, 3-tetramethylbutyl peroxy-2-ethylhexanoate (1 minute half-life temperature 124 ℃), and combinations thereof, T-butyl peroxy (2-ethylhexanoate) (1-minute half-life temperature 134 ℃ C.), 1-di-t-butylperoxycyclohexane (1-minute half-life temperature 153 ℃ C.), bis (4) -t-butylcyclohexyl) peroxydicarbonate (1-minute half-life temperature 92 ℃ C.), t-amyl peroxy-2-ethylhexanoate (1-minute half-life temperature 127 ℃ C.), t-amyl peroxy-3, 5, 5-trimethylhexanoate (1-minute half-life temperature 154 ℃ C.).
The conductive particles in the present invention may be metal particles, or may be metal-coated resin particles, and are not particularly limited; wherein the metal particles are selected from at least one of nickel, cobalt, silver, copper, gold and palladium; among them, nickel, silver and copper are preferred; in order to prevent oxidation of the surface of these metal particles, gold or palladium particles may be applied to the surface, or metal projections or a material coated with an organic substance as an insulating film may be used on the surface; the metal-coated resin particles may be particles obtained by coating the surface of a resin core with a metal such as nickel, copper, gold, or palladium; gold and palladium particles may be applied to the outermost surfaces of these particles, and similarly, metal projections or a material coated with an organic substance as an insulating film may be used on the surfaces; the resin core of the metal-coated resin particle may be styrene-divinylbenzene copolymer, amphetamine resin, crosslinked polystyrene resin, acrylic resin, styrene-quartz composite resin, or the like.
The present invention is not limited to a specific method for producing the metal-coated particles, and the metal-coated particles can be produced by an electroless plating method, a sputtering method, or the like.
The amount of the conductive particles added may be determined depending on the wiring pitch, connection area, and the like of the circuit component.
In addition, the circuit connecting material provided by the invention can also comprise other film-forming resins or inorganic fillers, organic fillers, silane coupling agents and the like; wherein the film-forming resin can be at least one selected from solid polyurethane resin, phenyl resin, epoxy resin, polyester resin, butadiene resin, polyimide resin and polyolefin resin; among them, polyurethane resins are preferred from the viewpoint of film-forming properties, processability and adhesiveness.
The circuit connecting material of the present invention may further include a silane coupling agent for improving adhesion to a substrate such as glass; the silane coupling agent is not particularly limited, and an epoxy silane coupling agent, an acryl silane coupling agent, a thiol silane coupling agent, an amino silane coupling agent, and the like may be selected.
The inorganic filler in the invention can be selected from quartz, titanium oxide, aluminum hydroxide and the like; wherein, the quartz can reduce the moisture absorption rate and the linear expansion coefficient of the hardened substance and improve the elastic modulus, thereby improving the reliability of the connection of the circuit connecting material; the titanium oxide can color the circuit connecting material black or white, etc., and can easily confirm whether the circuit connecting material is adhered to a proper position of the circuit board; the aluminum hydroxide can play a role in neutralizing acid remained in the resin after hardening, and the corrosion to the circuit electrode is relieved; the specific type of inorganic filler may be selected as desired.
The organic filler in the present invention may be fine particles composed of a copolymer containing components such as acrylic resin, silicone resin, butadiene rubber, polyester, polyurethane, polyvinyl butyral, polyacrylate, polyvinyl ester, polymethacrylate, polystyrene, NBR, SBR, etc., or fine particles having a core-shell structure; these organic fillers may be used singly or in combination of two or more; circuit connecting materials containing such organic fillers are effective in improving adhesion, stress relaxation after curing, and impact resistance.
The circuit connecting material provided by the invention simultaneously comprises the phosphate and the metal particles, so that free radicals are easily generated due to redox reaction, and the storage stability of the circuit connecting material is reduced; by adding the nitroso-containing compound, free radicals generated by redox reaction can be trapped, and further, the storage stability of the circuit connecting material can be prevented from being lowered.
The invention provides a circuit connecting material which can rapidly perform a connecting process at a low temperature in a short time, has a wide process margin when performing the connecting process, and can obtain a sufficiently stable adhesive strength.
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, embodiments of the present invention are described in detail below.
Examples 1 to 1
After 5 wt% of conductive particles (AUL704, manufactured by hydrochemical industries, Ltd.) was mixed and stirred with 35 wt% of urethane resin (Desmocoll406, manufactured by Covestro, Ltd.), 15 wt% of ester fluorene acrylate (TR-FR-301, manufactured by TRONLY, Ltd.), 40 wt% of urethane acrylate (Sartomer CN9782, manufactured by ARKEMA, Ltd.), 1 wt% of phosphate acrylate (Sartomer SR9050, manufactured by ARKEMA, Ltd.), 1 wt% of acrylic silane coupling agent (A-171, manufactured by MOMENTIVE, manufactured by MOVE, Ltd.), 3 wt% of sulfur dioxide-based organic peroxide (LUPEROX 331, 1 minute half-life temperature 124 ℃, manufactured by ARKEMA, Ltd.), and 0.01 wt% of nitroso-containing compound (CT5301, manufactured by ZAJO, manufactured by NEW chemical industries, Ltd.) by an automixer by means of a rotary stirrer, an applicator (BEVS1818, manufactured by CRES, manufactured by CROS, manufactured by BEVS 3, manufactured by CROS, manufactured by 60 ℃ C.) was painted, dried by means of a drying oven at 5 minutes, thus, a circuit connecting material A-1 containing conductive particles and having a thickness of 15 μm was obtained.
Examples 1 to 2
The nitroso-containing compound in this example was added in an amount of 0.1 wt%, and the rest was the same as in example 1. This example obtained a circuit-connecting material A-2 having a thickness of 15 μm.
Examples 1 to 3
The amount of the nitroso-containing compound added in this example was 3 wt%, and the rest was the same as in example 1. This example obtained a circuit-connecting material A-3 having a thickness of 15 μm.
Comparative example 1
This comparative example differs from example 1 in that no nitroso-containing compound is added. This comparative example obtained a circuit connecting material a having a thickness of 15 μm.
Example 2
The polymerization initiator in this example was a dioxy organic peroxide (PERKADOX L-W75, 1-minute half-life temperature 130 ℃ C., manufactured by Nouroyon Co., Ltd.) prepared from a dioxymethyl ester organic peroxide, and the rest was the same as in example 1. This example obtained a circuit-connecting material B-1 having a thickness of 15 μm.
Comparative example 2
This comparative example differs from example 2 in that no nitroso-containing compound is added. This comparative example obtained a circuit-connecting material B having a thickness of 15 μm.
Example 3
The polymerization initiator in this example was an alkyl methyl ester-based organic peroxide (LUPEROX575, a 1-minute half-life temperature of 125 ℃ C., manufactured by ARKEMA corporation), and the rest was the same as in example 1. This example obtained a circuit-connecting material C-1 having a thickness of 15 μm.
Comparative example 3
This comparative example differs from example 3 in that no nitroso-containing compound is added. This comparative example obtained a circuit-connecting material C having a thickness of 15 μm.
Example 4
The polymerization initiator in this example was an organic peroxide of oxoester type (Trigonox141, 1-minute half-life temperature 119 ℃ C., manufactured by Nouyon Co., Ltd.), and the rest was the same as in example 1. This example obtained a circuit-connecting material D-1 having a thickness of 15 μm.
Comparative example 4
This comparative example differs from example 4 in that no nitroso-containing compound is added. This comparative example obtained a circuit-connecting material D having a thickness of 15 μm.
Example 5
The polymerization initiator in this example was a palmitate-based organic peroxide (PARKADOX16, 1-minute half-life temperature 92 ℃, manufactured by Nouroyon Co., Ltd.), and the rest was the same as in example 1. This example obtained a circuit-connecting material E-1 having a thickness of 15 μm.
Comparative example 5
This comparative example differs from example 5 in that no nitroso-containing compound is added. This comparative example obtained a circuit-connecting material E having a thickness of 15 μm.
The circuit connecting materials prepared in the above examples and comparative examples were subjected to performance tests.
Measurement of DSC exothermic peak temperature
The circuit connecting materials prepared in the above examples and comparative examples were measured by differential scanning calorimetry (DSC250, TA Co., Ltd.) at a sample amount of 50mg, a measurement temperature range of 50 to 200 ℃ and a temperature rise rate of 10 ℃/min to determine a peak heating temperature; the test data are detailed in table 1.
Preparation of circuit connection structure
Cutting the circuit connecting materials A-E and (A-1) - (E-1) into pieces of 1.5mm multiplied by 50mm, and rolling on all ITO coated glass by adopting a desk type temporary sticking device (manufactured by model LD-02 bridge) under the condition of 70 ℃/1MP/2 sec; after the PET film was peeled off, a COF substrate (50umP, Line/Space 1/1, S' perflex substrate ") was attached, and then, by using a hot press (model BD-01, manufactured by Dodge corporation), connection was performed under a pressure condition of 170 ℃/3MPa/10sec at a Heat Tool speed of 10mm/sec and 0.1mm/sec, thereby obtaining a circuit connection structure.
Third, measurement of connection resistance
The connection structure thus produced was measured for the connection resistance value when a current of 1mA was applied between the terminals by the 4-terminal method, and the results are shown in table 1.
Fourth, measurement of adhesive Strength
After cutting the circuit connection structure on a COF at a width of 1cm, the adhesive strength was measured at a drawing speed of 50mm/sec using a tensile tester (AGS-5KNX, Shimadzu corporation); the results are shown in Table 1.
Fifth, evaluation of storage stability
After the circuit connecting materials A to E and (A-1) to (E-1) were left to stand at 40 ℃ for 15 days, a circuit connecting structure was fabricated under the same conditions, and the connection resistance value and the adhesive strength were measured; the results are shown in Table 1.
TABLE 1
From the above data, it can be seen that when the circuit connecting material provided by the present application contains a nitroso-containing compound, stable connection resistance can be obtained even under the condition of a slow hot-press apparatus, which is also beneficial to improving the storage stability of the circuit connecting material; further, the same effect can be obtained with different kinds of polymerization initiators.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the contents of the specification, and must be determined according to the claims.
Claims (10)
1. A circuit connecting material characterized by comprising a radical polymerization resin, a polymerization initiator, a nitroso-containing compound, and conductive particles.
2. The circuit-connecting material of claim 1 wherein said nitroso-containing compound is an aromatic nitroso compound.
3. The circuit-connecting material of claim 2 wherein said nitroso-containing compound is at least one member selected from the group consisting of aluminum N-nitrosophenylhydroxylamine and ammonium N-nitrosophenylhydroxylamine.
4. The circuit-connecting material according to claim 2, wherein the nitroso-containing compound is present in an amount of 0.01 to 3% by mass.
5. The circuit-connecting material according to any one of claims 1 to 4, wherein the kinds of the radical polymerization resins are two or more; the two or more free radical polymerization resins include a phosphate compound having an acrylate group or a methacrylate group in a molecule and a compound having at least two acrylate groups or methacrylate groups in a molecule.
6. The circuit-connecting material according to claim 5, wherein the phosphate compound having an acrylate group or a methacrylate group in the molecule has the following structural formulae (2) to (4):
wherein R is 1 、R 3 、R 5 Are both acrylate or methacrylate groups, R 2 、R 4 Are each hydrogen or methyl, and Y, Z, W, X, L, M are each an integer of 1 to 8.
7. The circuit-connecting material according to claim 6, wherein the mass fraction of the phosphate compound having an acrylate group or a methacrylate group in a molecule is 0.1 to 5%.
8. The circuit-connecting material of claim 5, the compound having at least two acrylate groups or methacrylate groups in a molecule is selected from at least one of epoxy (meth) acrylate oligomer, urethane (meth) acrylate oligomer, polyether (meth) acrylate oligomer, polyester (meth) acrylate oligomer, trimethylolpropane tri (meth) acrylate, polyethylene glycol di (meth) acrylate, polyalkylene glycol di (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, neopentyl glycol di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bis (2-acryloyloxyethyl) isocyanurate, and tris (2-acryloyloxyethyl) isocyanurate.
9. The circuit-connecting material of claim 6, wherein the polymerization initiator is at least one selected from the group consisting of diacyl peroxides, alkyl peresters, peroxyketals, peroxyesters, and peroxycarbonates.
10. The circuit-connecting material according to claim 9, wherein the polymerization initiator is contained in an amount of 0.1 to 10% by mass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210473835.3A CN114927256A (en) | 2022-04-29 | 2022-04-29 | Circuit connecting material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210473835.3A CN114927256A (en) | 2022-04-29 | 2022-04-29 | Circuit connecting material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114927256A true CN114927256A (en) | 2022-08-19 |
Family
ID=82807124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210473835.3A Pending CN114927256A (en) | 2022-04-29 | 2022-04-29 | Circuit connecting material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114927256A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006045459A (en) * | 2004-08-09 | 2006-02-16 | Hitachi Chem Co Ltd | Adhesive composition, circuit-connected structure and semiconductor device |
| CN101925663A (en) * | 2008-04-17 | 2010-12-22 | 日立化成工业株式会社 | Adhesive composition, adhesive for circuit connection, connected structure, and semiconductor device |
| CN102732207A (en) * | 2006-08-22 | 2012-10-17 | 日立化成工业株式会社 | Circuit connecting material, connection structure of circuit member, and method for manufacturing connection structure of circuit member |
| CN104169389A (en) * | 2012-04-25 | 2014-11-26 | 日立化成株式会社 | Circuit connection material, circuit connection structure, adhesive film, and wound body |
| CN108676520A (en) * | 2011-09-06 | 2018-10-19 | 日立化成株式会社 | Anisotropically conducting adhesive, the application of adhesive composite and connector |
-
2022
- 2022-04-29 CN CN202210473835.3A patent/CN114927256A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006045459A (en) * | 2004-08-09 | 2006-02-16 | Hitachi Chem Co Ltd | Adhesive composition, circuit-connected structure and semiconductor device |
| CN102732207A (en) * | 2006-08-22 | 2012-10-17 | 日立化成工业株式会社 | Circuit connecting material, connection structure of circuit member, and method for manufacturing connection structure of circuit member |
| CN101925663A (en) * | 2008-04-17 | 2010-12-22 | 日立化成工业株式会社 | Adhesive composition, adhesive for circuit connection, connected structure, and semiconductor device |
| CN108676520A (en) * | 2011-09-06 | 2018-10-19 | 日立化成株式会社 | Anisotropically conducting adhesive, the application of adhesive composite and connector |
| CN104169389A (en) * | 2012-04-25 | 2014-11-26 | 日立化成株式会社 | Circuit connection material, circuit connection structure, adhesive film, and wound body |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4421161B2 (en) | Wiring connecting material and wiring board manufacturing method using the same | |
| US8003017B2 (en) | Adhesive composition and anisotropic conductive film using the same | |
| KR101098205B1 (en) | Anisotropic electroconductive film | |
| KR100484383B1 (en) | Anisotropic conductive adhesives for connecting circuit, and connecting method of circuit board and circuit connected structure material using the same | |
| KR101393836B1 (en) | Anisotropic conductive film and method for producing connection structure | |
| KR101944125B1 (en) | Circuit connection material, connection method using same, and connection structure | |
| JP4605184B2 (en) | Wiring connecting material and wiring board manufacturing method using the same | |
| KR101872562B1 (en) | Circuitry connecting material and connecting method and connecting structure using same | |
| JP3877090B2 (en) | Circuit connection material and circuit board manufacturing method | |
| JP2001156430A (en) | Method of manufacturing circuit board and circuit connection material | |
| CN114927256A (en) | Circuit connecting material | |
| JP4794703B2 (en) | Circuit connection material, circuit terminal connection structure, and circuit terminal connection method | |
| JP4736280B2 (en) | Adhesive for circuit connection and circuit connection structure using the same | |
| JP2006127956A (en) | Anisotropic conductive film, manufacturing method of anisotropic conductive film, and connection body and semi-conductor device using this | |
| JP6102105B2 (en) | Film-like circuit connection material and circuit connection structure | |
| JPH11279513A (en) | Circuit connection material, connected structure of circuit terminal, and method for connecting circuit terminal | |
| JP2004067908A (en) | Anisotropically electroconductive adhesive | |
| KR102467385B1 (en) | Connection structure, circuit connection member and adhesive composition | |
| KR100714794B1 (en) | Low temperature and rapid curable anisotropic conductive film, and method for preparing the same | |
| JP5067101B2 (en) | Adhesive composition | |
| KR100815384B1 (en) | Composition for use in the formation of anisotropic conductive adhesive | |
| JP2002201440A (en) | Anisotropic conductive resin-film-forming composition, connection method of circuit boards using the same, and connection structure | |
| JP2008169389A (en) | Circuit connecting material and method of manufacturing circuit board | |
| JP2010004067A (en) | Circuit connection material | |
| KR20120078283A (en) | Anisotropic conductive adhesive having superior repairability and fast adhesiveness |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |