Compound, bonding agent, bonded body, printed circuit board, and method for manufacturing the bonded body.

Abstract

The present disclosure is a compound that includes, in a molecule: at least one functional group of an OH group and an OH-generating group; an organic group that contains a carbon-carbon double bond; and a triazine ring.

Description

[Technical Field]

[0001] This disclosure relates to compounds, bonding agents, bonded structures, printed circuit boards, and methods for manufacturing bonded structures. [Background technology]

[0002] Conventionally, bonding agents containing the compound of the following chemical formula (1) have been used to join dissimilar materials (for example, Patent Document 1). XY-Si-(CH3) a (OR) 3-a ...(1) (In chemical formula (1), X is an unsaturated group containing an alkenyl group, and Y is -(CH2) n1 -, -(C6H4)-, -(C6H4)CH2-, -NH-C6H4-, -NH-C6H4CH2-, and -NH-(CH2) n2 - is a spacer group selected from the following, where n1-n2 are numbers from 1 to 12, R is a methyl, ethyl, propyl, isopropyl, or butyl group, and a is a number from 0 to 2. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 2012 / 077676 [Overview of the project] [Problems that the invention aims to solve]

[0004] Incidentally, there may be a need for bonding agents and compounds that can further enhance bonding strength in the future, but such bonding agents and compounds have not been sufficiently studied to date.

[0005] Therefore, the present disclosure aims to provide a compound that can increase bonding strength, a bonding agent that can increase bonding strength, a bonded body obtained from the bonding agent, a printed circuit board containing the bonded body, and a method for manufacturing the bonded body using the bonding agent.

Means for Solving the Problem

[0006] The first aspect of the present disclosure relates to a compound having, in one molecule, at least one functional group selected from an OH group and an OH-generating group, an organic group containing a carbon-carbon double bond, and a triazine ring. Preferably, the compound has an alkoxysilyl group as the OH-generating group. Preferably, the compound is represented by the following general formula (1).

[0007]

Chemical formula

[0008] In the general formula (1), J is an organic group containing a carbon-carbon double bond, E is a group containing an OH group or an OH-generating group, Q is an organic group containing a carbon-carbon double bond that is the same as or different from J, or NR1(R2), R1 and R2 are each H, a hydrocarbon group having 1 to 24 carbon atoms, or -RSi(R’) n1 (OR’’) 3-n1 and may be the same or different, R is a linear divalent hydrocarbon group having 1 to 12 carbon atoms, R’ is a linear hydrocarbon group having 1 to 4 carbon atoms, R’’ is H or a linear hydrocarbon group having 1 to 4 carbon atoms, n1 is an integer of 0 to 2.

[0009] Preferably, E in the general formula (1) is NR1(R2). Preferably, Q in the general formula (1) is J. Preferably, Q in the general formula (1) is NR1(R2). Preferably, the compound has at least one of the following functional groups as the organic group containing a carbon-carbon double bond. CH2=CHNH-、 CH2=CH(CH2)NH- CH2=CH(CH2) n2 NH-(n2=2~16) 、 CH2=CHCH2(N-)CH2CH=CH2、 CH2=C(CH3)CH2NH- CH2=CHCH2(N-)C(CH3)3、 CH2=CHC6H4NH- CH2=CHC6H4CH2NH- CH2=C(CH3)(C=O)NH- CH2=CHCH2NH(C=O)NH- C6H5(N-)CH2CH=CH2、 -NH(NH2)C3N3CH=CH2、 CH2=CHO-、 CH2=CH(CH2)O- CH2=CH(CH2) n3 O-(n3=2~16)、 CH2=C(CH3)CH2O- CH2=CHC6H4O- CH2=CHC6H4CH2O- CH2=CH-O(CH2) n4 O-(n4=1-16)ぁ CH2=CH-O(CH2)2O- (CH2)2O-、 CH2=CHS-、 CH2=CH(CH2)S-、 CH2=CH(CH2) n5 S-(n5=2~16)、 CH2=C(CH3)CH2S- CH2=CHC6H4S-、 CH2=CHC6H4CH2S-、 (CH2=CHCH2NCH2CH=CH2)2C3N3S-、 (CH2=CHCH2NH)2C3N3S-、 (CH2=CHCH2NCH2CH=CH2)C3N3(SH)S-、 (CH2=CHCH2NH)C3N3(SH)S-, CH2=CHCOO-(CH2) n7 -S-(n7=1~16), CH2=C(CH3)COO-(CH2) n8 -S-(n8=1~16), CH2=CH-, CH2=CH(CH2)- CH2=CH(CH2) n6 -(n6=2~16) CH2=C(CH3)CH2-, CH2=CHC6H4-, CH2=CHC6H4CH2-,

[0010] The second part of this disclosure relates to a bonding agent containing the compound (α). Preferably, the bonding agent is used to bond material A and polymer material B. Preferably, material A is a metallic material.

[0011] A third aspect of this disclosure relates to a bonded body in which material A and polymer material B are bonded together by the bonding agent.

[0012] The fourth aspect of this disclosure relates to a printed circuit board including the bonded body.

[0013] The fifth aspect of this disclosure is a method for producing a bonded body, comprising joining a substrate A having material A on its surface A and a substrate B having polymer material B on its surface B with a bonding agent, The process of applying the bonding agent to the surface A (X), The process (Y) involves butting the substrate A and the substrate B together so that the surface A and the surface B come into contact with each other via the bonding agent, The process (Z) involves applying pressure to the contact surfaces of surface A and front surface B via the bonding agent to obtain the joined body, The present invention relates to a method for manufacturing a joint, which includes the following features. Preferably, the method for manufacturing the bonded body further comprises step (A) before step (X), in which one or more treatments selected from the group consisting of degreasing, corona discharge, plasma discharge, ultraviolet irradiation, acid treatment, alkali treatment, steam treatment, and chemical conversion treatment are applied to the surface A to generate OH groups on the surface A. Preferably, the method for producing the bonded body involves heating the surface A and the bonding agent after step (X) to chemically bond the OH groups of the surface A to at least one of the functional groups of the OH groups and OH-forming groups of the compound (α) by dehydration condensation. Preferably, in the method for manufacturing the joint, step (X) involves immersing the surface A in the adhesive, spraying the adhesive onto the surface A, or applying the adhesive to the surface A using a coating device to provide the adhesive to the surface A. Preferably, in the method for manufacturing the bonded body, in (Z), pressure is applied to the contact surfaces of surface A and front surface B via the bonding agent so that the polymer material B and the adhesive come into contact. Preferably, the method for manufacturing the joint involves performing the pressurization in step (Z) under temperature conditions of 0 to 350°C. Preferably, in the method for manufacturing the joint, step (Z) involves heating and pressurizing the contact surface.

[0014] The sixth aspect of this disclosure is a method for producing a bonded body in which a metal material and a polymer material B are joined together with a bonding agent, Using the aforementioned bonding agent, The bonding agent has an alkoxysilyl group as the OH generating group, A step of providing the bonding agent to the surface B of a substrate B having the polymer material B on its surface B, thereby causing the triazine ring and the alkoxysilyl group to appear on the surface B, The step of applying an electroless plating solution to the triazine ring and the alkoxysilyl group of the surface B, The present invention relates to a method for manufacturing a joint, which includes the following features.

[0015] The seventh aspect of this disclosure is a bonding agent used for joining a metal material and a polymer material B, This invention relates to a bonding agent that exhibits a peel strength of 5 N / cm or more when peeled at a speed of 50 mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel". Preferably, the bonding agent has a peel strength of 5 N / cm or more after a solder reflow test at 260°C. Preferably, the bonding agent is used to bond copper foil having the metallic material copper. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.5 μm. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.0 μm. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.8 μm. Preferably, the bonding agent contains a compound (α) represented by the following general formula (1).

[0016] [ka]

[0017] In addition, in the above general formula (1), J is an organic group containing a carbon-carbon double bond, E is a group containing an OH group or an OH-forming group. Q is an organic group containing a carbon-carbon double bond, which is the same as or different from J, or NR1(R2). R1 and R2 are, respectively, H, a hydrocarbon group having 1 to 24 carbon atoms, or -RSi(R') n1 (OR'') 3-n1 They may be the same or different, The aforementioned R is a chain-like, divalent hydrocarbon group having 1 to 12 carbon atoms. The aforementioned R' is a chain-like hydrocarbon group having 1 to 4 carbon atoms. The aforementioned R'' is H, or a chain-like hydrocarbon group having 1 to 4 carbon atoms. (The aforementioned n1 is an integer between 0 and 2.)

[0018] The eighth aspect of this disclosure is a bonded body in which a metal material and a polymer material B are bonded together with a bonding agent, This invention relates to a bonded material in which the peel strength is 5 N / cm or more when a metallic or polymer material is peeled at a speed of 50 mm / min, in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel". Preferably, the peel strength of the bonded body after a solder reflow test at 260°C is 5 N / cm or more. Preferably, the joint is formed by joining copper foil having the metallic material copper. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.5 μm. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.0 μm. Preferably, the surface roughness (Rz) of the bonding surface of the copper foil is 0.8 μm.

[0019] The ninth part of this disclosure relates to a printed circuit board including the bonded body. [Effects of the Invention]

[0020] According to this disclosure, the bonding strength can be increased. [Modes for carrying out the invention]

[0021] An embodiment of this disclosure will be described below.

[0022] The configurations and combinations thereof in each embodiment are examples only, and additions, omissions, substitutions, and other modifications are permitted as appropriate, without departing from the spirit of this disclosure. This disclosure is not limited by the embodiments, but is limited only by the scope of the claims. Furthermore, each aspect disclosed herein can be combined with any other features disclosed herein.

[0023] <This embodiment> The compound according to this embodiment is a compound (α) having at least one of an OH group and an OH-forming group, an organic group containing a carbon-carbon double bond, and a triazine ring in one molecule.

[0024] Examples of triazines in the triazine ring include 1,3,5-triazine.

[0025] The compound (α) preferably has an alkoxysilyl group as the OH generating group. The aforementioned alkoxysilyl group is -RSi(R') n1 (OR'') 3-n1 It is preferable that this be the case. Furthermore, R is a chain-like divalent hydrocarbon group having 1 to 12 carbon atoms, R' is a chain-like hydrocarbon group having 1 to 4 carbon atoms, R'' is H or a chain-like hydrocarbon group having 1 to 4 carbon atoms, and n1 is an integer from 0 to 2.

[0026] In this embodiment, the "hydrocarbon group" and "hydrocarbon" may each have groups such as -NH-, -CO-, -O-, -S-, and -COO-. Furthermore, the terms "hydrocarbon group" and "hydrocarbon" may be either a chain-like hydrocarbon group or a cyclic group. Furthermore, the "hydrocarbon group" and "hydrocarbon" may each have substituents (cyclic or chain-like).

[0027] The number of carbon atoms in R is preferably 1 to 18, more preferably 1 to 12. For example, R can be -C n H 2n These are some examples.

[0028] For example, R' can be -C n H 2n+1 These are some examples.

[0029] When R'' is a hydrocarbon group, examples of R'' include -CH3, -C2H5, -CH(CH3)2, -C(CH3)3, etc.

[0030] Furthermore, the compound (α) is preferably represented by the following general formula (1).

[0031] [ka]

[0032] In the general formula (1) above, J is an organic group containing a carbon-carbon double bond. E is a group containing an OH group or an OH-forming group. Q is an organic group containing a carbon-carbon double bond, which is the same as or different from J, or NR1(R2). R1 ​​and R2 are H, a hydrocarbon group having 1 to 24 carbon atoms, or -RSi(R'), respectively. n1 (OR'') 3-n1 These may be the same or different. R is a chain-like divalent hydrocarbon group having 1 to 12 carbon atoms. R' is a chain-like hydrocarbon group having 1 to 4 carbon atoms. R'' is H, or a chain-like hydrocarbon group having 1 to 4 carbon atoms. n1 is an integer from 0 to 2.

[0033] In the general formula (1) above, it is preferable that E is NR1(R2). In other words, the compound (α) is preferably represented by the following general formula (2).

[0034] [ka]

[0035] In the general formula (2) above, it is preferable that Q is J. In other words, the compound (α) is preferably represented by the following general formula (3).

[0036] [ka]

[0037] Furthermore, in the general formula (2) above, it is preferable that Q is NR1(R2). In other words, the compound (α) is preferably represented by the following general formula (4).

[0038] [ka]

[0039] An organic group containing a carbon-carbon double bond can react with carbon-carbon double bonds, etc., contained in polymer material B of substrate B, which will be described later. The organic group may have a benzene ring, but if it has a benzene ring, it will have carbon-carbon double bonds other than the carbon-carbon double bonds contained in the benzene ring.

[0040] The compound (α) preferably contains two or more, more preferably two to four, and even more preferably four carbon-carbon double bonds per molecule that can react with the carbon-carbon double bonds contained in the substrate B described later. The bonding strength is further enhanced when the compound (α) contains two or more carbon-carbon double bonds in a single molecule.

[0041] The organic group containing the carbon-carbon double bond may also include nitrogen or sulfur.

[0042] Examples of organic groups containing the carbon-carbon double bond include the following functional groups.

[0043] CH2=CHNH-, CH2=CH(CH2)NH-, CH2=CH(CH2) n2 NH-(n2=2~16) CH2=CHCH2(N-)CH2CH=CH2, CH2=C(CH3)CH2NH-, CH2=CHCH2(N-)C(CH3)3, CH2=CHC6H4NH- CH2=CHC6H4CH2NH- CH2=C(CH3)(C=O)NH- CH2=CHCH2NH(C=O)NH- C6H5(N-)CH2CH=CH2、 -NH(NH2)C3N3CH=CH2

[0044] CH2=CHO-、 CH2=CH(CH2)O- CH2=CH(CH2) n3 O-(n3=2~16)、 CH2=C(CH3)CH2O- CH2=CHC6H4O- CH2=CHC6H4CH2O- CH2=CH-O(CH2) n4 O-(n4=1-16)ぁ CH2=CH-O(CH2)2O- (CH2)2O-

[0045] CH2=CHS-、 CH2=CH(CH2)S-、 CH2=CH(CH2) n5 S-(n5=2~16)、 CH2=C(CH3)CH2S- CH2=CHC6H4S-、 CH2=CHC6H4CH2S-、 (CH2=CHCH2NCH2CH=CH2)2C3N3S-、 (CH2=CHCH2NH)2C3N3S-、 (CH2=CHCH2NCH2CH=CH2)C3N3(SH)S-、 (CH2=CHCH2NH)C3N3(SH)S-、 CH2=CHCOO-(CH2) n7 -S-(n7=1~16)、 CH2=C(CH3)COO-(CH2) n8 -S-(n8=1~16)

[0046] CH2=CH-, CH2=CH(CH2)- CH2=CH(CH2) n6 -(n6=2~16) CH2=C(CH3)CH2-, CH2=CHC6H4-, CH2=CHC6H4CH2-

[0047] Next, we will describe an example of a method for producing compound (α) according to this embodiment, using 2,4-bis(diallylamino)-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine (formula shown below) as an example of compound (α) according to this embodiment. A more specific production method will be shown in Example 1, which will be described later.

[0048] [ka]

[0049] In a three-necked flask under a nitrogen atmosphere, a mixed solution of cyanuryl chloride and tetrahydrofuran (THF) is added to a mixed solution of 3-aminopropyltriethoxysilane and tetrahydrofuran (THF), and then a mixed solution of triethylamine (TEA) and tetrahydrofuran (THF). This reaction, as shown in the chemical equation below, produces the intermediate 6-(3-triethoxysilylpropylamino)-1,3,5-triazine-2,4-dichloride.

[0050] [ka]

[0051] Next, by adding a mixed solution of diallylamine and tetrahydrofuran (THF) to a mixed solution of the intermediate and tetrahydrofuran (THF), the compound (α), 2,4-bis(diallylamino)-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine, can be produced by the reaction shown in the chemical equation below.

[0052] [ka]

[0053] In the above chemical reaction equation for generating the intermediate, only one group containing an alkoxysilyl group is bonded to the triazine ring. However, by adjusting the amount of 3-aminopropyltriethoxysilane relative to the amount of cyanuryl chloride, two groups containing alkoxysilyl groups may be bonded to the triazine ring.

[0054] Furthermore, in the above reaction equation for generating compound (α) from the intermediate, diallylamine was used to bond "CH2=CH(CH2)NH-" to the triazine ring, but a different amine may be used to bond the following organic group to the triazine ring. CH2=CHNH-, CH2=CH(CH2) n2 NH-(n2=2~16) CH2=CHCH2(N-)CH2CH=CH2, CH2=C(CH3)CH2NH-, CH2=CHCH2(N-)C(CH3)3, CH2=CHC6H4NH-, CH2=CHC6H4CH2NH-, CH2=C(CH3)(C=O)NH-, CH2=CHCH2NH(C=O)NH-, C6H5(N-)CH2CH=CH2, -NH(NH2)C3N3CH=CH2

[0055] Alternatively, an alcohol may be used instead of diallylamine to bond the following organic groups to the triazine ring. CH2=CHO-, CH2=CH(CH2)O-, CH2=CH(CH2) n3 O-(n3=2~16) CH2=C(CH3)CH2O-, CH2=CHC6H4O-, CH2=CHC6H4CH2O-, CH2=CH-O(CH2) n4 O-(n4=1-16), CH2=CH-O(CH2)2O- (CH2)2O-

[0056] Furthermore, a thiol may be used instead of diallylamine to bond the following organic groups to the triazine ring. CH2=CHS-, CH2=CH(CH2)S-, CH2=CH(CH2) n5 S-(n5=2~16), CH2=C(CH3)CH2S-, CH2=CHC6H4S-, CH2=CHC6H4CH2S- (CH2=CHCH2NCH2CH=CH2)2C3N3S-, (CH2=CHCH2NH)2C3N3S-, (CH2=CHCH2NCH2CH=CH2)C3N3(SH)S-, (CH2=CHCH2NH)C3N3(SH)S-, CH2=CHCOO-(CH2) n7 -S-(n7=1~16), CH2=C(CH3)COO-(CH2) n8 -S-(n8=1~16)

[0057] Alternatively, a Grignard reagent may be used instead of diallylamine to bond the following organic groups to the triazine ring. CH2=CH-, CH2=CH(CH2)- CH2=CH(CH2) n6 -(n6=2~16) CH2=C(CH3)CH2-, CH2=CHC6H4-, CH2=CHC6H4CH2-

[0058] Next, the adhesive according to this embodiment will be described.

[0059] The bonding agent according to this embodiment contains compound (α) according to this embodiment.

[0060] The bonding agent according to this embodiment may contain a solvent. Examples of solvents include water, alcohols (e.g., methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, cellosorb, carbitol), ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (e.g., benzene, toluene, xylene), aliphatic hydrocarbons (e.g., hexane, octane, decane, dodecane, octadecane), esters (e.g., ethyl acetate, methyl propionate, methyl phthalate), ethers (e.g., tetrahydrofuran, ethyl butyl ether, anisole), and the like. The concentration of compound (α) in the bonding agent according to this embodiment is preferably 0.0001 to 10% by mass, more preferably 0.01 to 5.0% by mass, and even more preferably 0.1 to 3.0% by mass.

[0061] The bonding agent according to this embodiment is preferably used for joining dissimilar materials. The bonding agent according to this embodiment is preferably used to bond material A and polymer material B. Specifically, the bonding agent according to this embodiment is used to bond a substrate A having material A on its surface A and a substrate B having polymer material B on its surface B. The bonding agent according to this embodiment is used so that surface A and front surface B come into contact via the bonding agent. Material A is a different material from the polymer material.

[0062] The polymer material B is preferably a polymer material having a "carbon-carbon double bond" that can react with the "carbon-carbon double bond" contained in the compound (α). In this embodiment, the term "polymer material having a carbon-carbon double bond that can react with the carbon-carbon double bond contained in compound (α)" also includes the concept of "a polymer material that, as a result of modification, has acquired a carbon-carbon double bond that can react with the carbon-carbon double bond contained in compound (α)." In other words, in this embodiment, "a polymer material having a carbon-carbon double bond that can react with the carbon-carbon double bond contained in compound (α)" means a polymer material having a carbon-carbon double bond that can react with the carbon-carbon double bond contained in compound (α), either due to modification or without modification.

[0063] Examples of polymer materials having a "carbon-carbon double bond" that can react with the "carbon-carbon double bond" contained in the aforementioned compound (α) include polyphenylene ether (m-PPE), which is a modified resin having a carbon-carbon double bond at its terminal or side chain.

[0064] Furthermore, polymer materials having a "carbon-carbon double bond" that can react with the "carbon-carbon double bond" contained in the compound (α) include polybutadiene, unsaturated polyester, bismaleimidotriazine, natural rubber (NR), butadiene rubber (BR), styrene-butadiene rubber (SBR), acrylonitrile-butadiene rubber (NBR), butyl rubber (isobutylene-isoprene copolymer) (IIR), ethylene-propylene rubber (EPDM), and chloroprene rubber (CR).

[0065] Furthermore, polymer materials having carbon-carbon double bonds that can react with the carbon-carbon double bonds contained in compound (α) include polymer materials that have been modified to have carbon-carbon double bonds, as listed below. Polyethylene (PE), polypropylene (PP), polystyrene (PS), cycloolefin polymer (COP), cycloolefin copolymer (COC), polyimide, polyphenylene sulfide (PPS), polysulfone, polyethersulfone, polyetheretherketone, fluororesin, silicone resin, polyamide, polyester, liquid crystal polymer (LCP), etc.

[0066] Furthermore, the substrate B may contain additives as needed. Examples of additives include crosslinking agents, crosslinking accelerators, crosslinking aids, radical initiators, cationic initiators, photopolymerization initiators, scorch inhibitors, stabilizers, anti-aging agents, UV inhibitors, fillers, reinforcing agents, plasticizers, softeners, colorants, viscosity modifiers, and flame retardants.

[0067] Various types of polymerization initiators, crosslinking agents, crosslinking accelerators, and crosslinking aids can be used. For example, peroxides, cationic polymerization initiators, photopolymerization initiators, sulfur, sulfur-based crosslinking accelerators, polyol-based crosslinking agents, polyamine-based crosslinking agents, polythiol-based crosslinking agents, acrylate-based crosslinking aids, methacrylate-based crosslinking aids, and allyl-based crosslinking aids are used. Specifically, examples include azobisbutyronitrile, benzophenone, Michler ketone, benzoin isopropyl ether, chlorothioxanthone, isopropylthioxanthone, benzyldimethyl ketal, acetophenone diethyl ketal, α-hydroxycyclohexylphenyl ketone, and 2-hydroxy-2-methylphenylpropane. Acetophenone derivative compounds (for example, 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl)ketone, α-hydroxy-α,α'-dimethylacetophenone, methoxyacetophenone, and 2,2-dimethoxy-2-phenylacetophenone) are also used. Benzoin ether compounds (e.g., benzoin ethyl ether, benzoin propyl ether) are also examples. Ketal derivative compounds such as benzyldimethyl ketal are also examples. Halide ketones, acyl phosphine oxides, acyl phosphonates, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide, phenyldimethyl sulfonium chloride, and triarylsulfonium hexafluorophosphate are also examples. Triazine dithiol crosslinking agents, resin crosslinking agents, polyol crosslinking agents, H-terminated siloxane crosslinking agents, and silanol condensation crosslinking agents are also examples.Dibenzothiazoyl disulfide, 4-morpholinodithiobenzothiazole, N-cyclohexyl-2-benzothiazoyl sulfenamide, Nt-butyl-2-benzothiazoyl sulfenamide, N-oxydiethylene-2-benzothiazoyl sulfenamide, N-diisopropyl-2-benzothiazoyl sulfenamide, N-dicyclohexyl-2-benzothiazoyl sulfenamide, tetramethylthuram disulfide, tetraethylthuram disulfide, tetrabutylthuram disulfide, tetraoctylthuram disulfide, amines, hexamethylenetetramine, zarigen, quaternary ammonium salts, phosphonium salts, dialkyltin organic salts, titanates, polyethylene glycol, chloroplatinic acid, zinc oxide, magnesium oxide, calcium oxide, barium oxide, aluminum oxide, calcium hydroxide, tin oxide Other examples include iron oxide, calcium hydroxide, calcium carbonate, magnesium carbonate, sodium fatty acid, calcium octoate, potassium isooctylate, potassium butoxide, cesium octoate, potassium isostearate, polyethylene glycol, polypropylene glycol, hexanediol, cyclohexanediol, dodecanediol, hexamethylenediamine, dodecanediamine, terminal diaminopolyethylene glycol, terminal diaminopolypropylene glycol, benzenedithiol, hexanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, polypropylene glycol diacrylate, polypropylene glycol dimethacrylate, diallyl ether, triallyl isocyanurate, and triallyl cyanurate.

[0068] The shape of the substrate B may be sheet-like, plate-like, columnar, rod-like, frame-like, box-like, fibrous, or thread-like. Alternatively, the shape of the substrate B may be film-like, woven fabric-like, nonwoven fabric-like, or foam-like.

[0069] The substrate B may contain various fillers and reinforcing agents in appropriate amounts as needed. For example, various carbon blacks, calcium carbonate, talc, clay, kaolin, glass, wet silica, and dry silica may be included as needed. Rayon, nylon, polyester, vinylon, steel, Kevlar, carbon fiber, glass fiber, and cloth may be included as needed. Metal particles (copper, nickel, silver, gold, tin, etc.) may be included as needed. Carbon particles may be included as needed. Conductive materials may be included as needed. Heat transfer materials such as alumina, silicon nitride, alumina nitride, silicon carbide, and diamond may be included as needed. The content is 200 parts by mass or less per 100 parts by mass of polymer material. Generally, it is 100 parts by mass or less.

[0070] The aforementioned base B may contain a stabilizer in an appropriate amount as needed. The stabilizer may be, for example, an anti-aging agent or an ultraviolet absorber. For example, it may be an amine-ketone condensate such as poly(2,2,4-trimethyl-1,2-dihydroquinoline) or 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline. It may also be an aromatic secondary amine compound such as octyldiphenylamine, 4,4-bis(α,α-dimethylbenzyl)diphenylamine, N,N-diphenyl-p-phenylenediamine, N-phenyl-N'-isopropyl-p-phenylenediamine, or N-phenyl-N'-isopropyl-1,3-dimethylbutyl-p-phenylenediamine. These are mono- or bisphenol compounds such as styrene-phenol, 2,6-di-t-butyl-4-phenol, 2-t-butyl-6-(3-t-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate, 2,2-methylenebis(4-methyl-6-t-butylphenol), 4,4-thiobis(3-methyl-6-t-butylphenol)2,5-di-t-butylhydroquinone, etc. These are sulfur-based or phosphorus-based compounds such as 2-mercaptobenzimidazole, 2-Zn mercaptobenzimidazole, nickel dimethyldithiocarbamate, 1,3-bis(dimethylaminopropyl)thiourea, dilauryl-3,3-thiodipropionate, tris(nonylated phenyl)phosphite, etc. The content is preferably 30 parts by mass or less, more preferably 0.5 to 5 parts by mass, and even more preferably 0.5 to 3 parts by mass, per 100 parts by mass of polymer material B.

[0071] The substrate B may contain, as needed, softeners, plasticizers, processing aids, viscosity modifiers, colorants, etc., in appropriate amounts.

[0072] When the substrate B is used as a substrate for a printed circuit board, the elastic modulus of the substrate B is preferably 2.0 GPa or higher, and more preferably 2.3 GPa or higher. Furthermore, the elastic modulus of the substrate B is preferably 4.5 GPa or lower, and more preferably 2.6 GPa or lower.

[0073] It is preferable that the material A has a functional group that can react with at least one of the "OH group and OH-forming group" contained in the compound (α). Examples of functional groups that can react with "at least one of the functional groups of an OH group and an OH-producing group" include OH groups, OH-producing groups, and so on. Furthermore, if material A does not have a functional group that reacts with "at least one of the functional groups of an OH group and an OH-forming group" contained in compound (α), it is preferable that the surface A of the substrate A is subjected to one or more treatments selected from the group consisting of degreasing, corona discharge, plasma discharge, ultraviolet irradiation, acid treatment, alkali treatment, steam treatment, and chemical conversion treatment, so that the substrate A has an OH group on its surface A. The substrate A has a functional group on its surface A that can react with at least one of the functional groups of an OH group and an OH-producing group. This allows the substrate A to react with at least one of the functional groups of an OH group and an OH-producing group contained in compound (α) and chemically bond with compound (α), thereby further increasing the bonding strength.

[0074] Examples of material A include metallic materials, ceramics, polymer materials, and the like.

[0075] Examples of the aforementioned metallic material include single metals and alloys. Examples of the aforementioned single metals include Be, Mg, Ca, St, Ba, Ra, Sc, It, Ti, Zr, V, Nb, Ta, Cr, Mo, W, Mn, Fe, Co, rhodium, Ir, Ni, palladium, Pt, Cu, Ag, Au, Zn, Cd, Hg, Al, Ge, Sn, Pb, An, Bi, neodymium, and the like. Examples of the aforementioned alloys include iron alloys, copper alloys, aluminum alloys, magnesium alloys, zinc alloys, tin alloys, nickel alloys, gold alloys, silver alloys, platinum alloys, palladium alloys, lead alloys, titanium alloys, cadmium alloys, zirconium alloys, cobalt alloys, chromium alloys, molybdenum alloys, tungsten alloys, manganese alloys, ferritic stainless steel, martensitic stainless steel, austinite stainless steel, precipitation-strengthened stainless steel, nickel-titanium alloys, iron-manganese-titanium alloys, and superelastic alloys (nickel-titanium alloys). Furthermore, the metal may be a functional metal, amorphous metal, fiber-reinforced metal, shape memory alloy, or superelastic alloy.

[0076] Examples of the aforementioned ceramics include metal oxides, ceramics, glass, cement, and gypsum. Enamelware is also acceptable. Diamond-based materials are also acceptable. Metal oxides such as alumina, mullite, zirconia, and zinc oxide are also acceptable. Hydroxides such as hydroxyapatite are also acceptable. Carbides such as silicon carbide are also acceptable. Carbonate-based materials are also acceptable. Nitride-based materials such as silicon nitride, silicon nitride, and aluminum nitride are also acceptable. Halide-based materials such as fluorite are also acceptable. Phosphate-based materials such as apatite are also acceptable. Barium titanate and lead zirconate titanate are also acceptable. Ferrite, steatite, forsterite, cordierite, sialon, zircon, etc. are also acceptable. In addition, high-temperature superconducting ceramics and machinable ceramics are also acceptable. Fiber-reinforced ceramics such as carbon fiber, organic fiber, metal fiber, and glass fiber are also acceptable.

[0077] Examples of polymer materials for material A include cellulose, cellulose derivatives, hydroxyethylcellulose, starch, cellulose diacetate, surface saponified vinyl acetate resin, low-density polyethylene, high-density polyethylene, polypropylene, ethylene-propylene copolymer, petroleum resin, polystyrene, syndiotactic-polystyrene, styrene copolymer, chroman-indene resin, terpene resin, styrene-divinylbenzene copolymer, acrylonitrile-butadiene-styrene copolymer resin, methyl polyacrylate, ethyl polyacrylate, polyacrylonitrile, methyl polyacrylate, polymethyl methacrylate, polyethyl methacrylate, polycyanoacrylate, polyvinyl acetate, ethylene-vinyl acetate copolymer resin, polyvinyl alcohol, polyvinyl formal, and Polyvinyl acetal, vinyl acetate copolymer, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, polyvinylidene fluoride, vinylidene fluoride-ethylene copolymer, vinylidene fluoride-propylene copolymer, poly-1,4-transpolybutadiene, poly-1,2-transpolybutadiene, polyoxymethylene, polyethylene glycol, polypropylene glycol, phenol-formaldehyde resin, cresol-formaldehyde resin, resorcinol resin, melamine resin, xylene resin, toluene resin, glyptal resin, modified glyptal resin, polyethylene terephthalate, polybutylene terephthalate, unsaturated polyester resin, polyester acrylate, allyl ester resin, polycarbonate, 6-nylon, 6',6-nylon, 6',10-Nylon, polyimide, polyamide, polybenzimidazole, polybenzoxazole, polybenzthiazole, polyamideimide, silicon resin, addition-curing silicone rubber, polymerization-curing silicone rubber, condensation-curing silicone rubber, addition-curing silicone resin, furan resin, polyurethane resin, epoxy resin, polyphenylene oxide, polydimethylphenylene oxide, blend polymers (polymer alloys) of polyphenylene oxide or polydimethylphenylene oxide and triallyl isocyanurate, blend polymers (polymer alloys) of polyphenylene oxide or polydimethylphenylene oxide and triallyl isocyanurate peroxide, polyxylene, polyphenylene sulfide, polycycloolefin, polysulfone, polyethersulfone, polyetheretherketone, polyimide, liquid crystal resin (LCP), natural rubber, 1,4-cis-butadiene rubber, isoprene rubber, polychloroprene, styrene-butadiene copolymer rubber, hydrogenated styrene-butadiene copolymer rubber Examples include acrylonitrile-butadiene copolymer rubber, hydrogenated acrylonitrile-butadiene copolymer rubber, polybutene rubber, polyisobutylene rubber, ethylene-propylene rubber, ethylene-propylene-diene rubber, ethylene oxide-epichlorohydrin copolymer rubber, chlorinated polyethylene rubber, chlorosulfonated polyethylene rubber, alkylated chlorosulfonated polyethylene rubber, chloroprene rubber, chlorinated acrylic rubber, brominated acrylic rubber, fluororubber, epichlorohydrin copolymer rubber, chlorinated ethylene-propylene rubber, chlorinated butyl rubber, brominated butyl rubber, homopolymer rubbers such as tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, and tetrafluoroethylene, and their binary and ternary copolymer rubbers, ethylene-tetrafluoroethylene copolymer rubber, propylene-tetrafluoroethylene copolymer rubber, ethylene acrylic rubber, peroxide-type silicone rubber, addition-type silicone rubber, condensation-type silicone rubber, epoxy rubber, urethane rubber, and elastomers with unsaturated groups at both ends.

[0078] As material A, a material that can coordinately bond with the triazine ring contained in compound (α) is preferred. The bonding strength is further increased when material A and the triazine ring contained in compound (α) form a coordinate bond. From the standpoint of being able to coordinate bond with the triazine ring, a metallic material is preferred for material A, and Cu, Zn, Ni, and Fe are more preferred.

[0079] The shape of the substrate A may be sheet-like, plate-like, columnar, rod-like, frame-like, box-like, fibrous, or thread-like. Alternatively, the shape of the substrate A may be film-like, woven fabric-like, nonwoven fabric-like, or foam-like.

[0080] Incidentally, conventionally, when manufacturing a flexible printed circuit board (FPC) by joining a substrate A having copper on its surface to a resin substrate B, the surface roughness of the copper-surfaced substrate A is increased to enhance the bonding strength between substrate A and substrate B, thereby enabling an anchoring effect. However, if the surface of the substrate A is rough, conductor loss occurs, resulting in transmission loss. Consequently, it becomes difficult to ensure the quality of the transmitted signal in the high-frequency range. However, by using the bonding agent according to this embodiment, even if the surface roughness of the copper-surfaced substrate A is small, the bonding strength between the copper-surfaced substrate A and the resin substrate B can be increased. As a result, it becomes easier to ensure the quality of the transmitted signal, especially in the high-frequency range. Therefore, the bonding agent according to this embodiment is particularly suitable for manufacturing a flexible printed circuit board (FPC) by bonding a substrate A having copper on its surface to a resin substrate B.

[0081] The bonded body according to this embodiment is a bonded body in which material A and polymer material B are joined together with a bonding agent according to this embodiment.

[0082] The printed circuit board according to this embodiment includes a bonded body according to this embodiment.

[0083] The method for manufacturing a bonded body according to this embodiment is a method for producing a bonded body in which a substrate A having material A on its surface A and a substrate B having polymer material B on its surface B are joined together with a bonding agent. Furthermore, the method for manufacturing the joint according to this embodiment comprises the steps of: (X) providing the adhesive according to this embodiment to the surface A; (Y) butting the base body A and the base body B together so that the surface A and the surface B come into contact with each other via the adhesive; and (Z) obtaining the joint by applying pressure to the contact surfaces of the surface A and the front surface B via the adhesive.

[0084] In the method for manufacturing the bonded body according to this embodiment, step (X) chemically bonds the substrate A with the compound (α) contained in the bonding agent according to this embodiment, so that a triazine ring and a carbon-carbon double bond appear on the surface of the substrate A. Furthermore, by step (Z), a chemical bond is formed between the substrate B and the carbon-carbon double bond of compound (α), thereby increasing the bonding strength between substrate A and substrate B.

[0085] Furthermore, the method for manufacturing the bonded body according to this embodiment further comprises a step (A) prior to step (X) in which one or more treatments selected from the group consisting of degreasing, corona discharge, plasma discharge, ultraviolet irradiation, acid treatment, alkali treatment, steam treatment, and chemical conversion treatment are applied to the surface A to generate OH groups on the surface A.

[0086] In step (X), the surface A is immersed in the adhesive, the adhesive is sprayed onto the surface A, or the adhesive is applied to the surface A using a coating device to provide the adhesive to the surface A.

[0087] In (Z) above, pressure is applied to the contact surface between surface A and front surface B via the bonding agent so that the polymer material B and the adhesive come into contact. In step (Z) above, the contact surface is pressurized, preferably at 0.01 to 50 MPa, more preferably at 0.1 to 5 MPa. Furthermore, the pressurization in step (Z) is preferably carried out under temperature conditions of 0 to 350°C, more preferably 40 to 350°C, and even more preferably 80 to 350°C. Furthermore, in step (Z), the contact surface may be heated while applying pressure.

[0088] <Other embodiments> Next, other embodiments will be described. Note that explanations that overlap with this embodiment will be omitted, and unless otherwise specified in other embodiments, the content will be the same as that described in this embodiment.

[0089] Another embodiment describes a method for manufacturing a bonded body in which a metal material and a polymer material B are joined together with a bonding agent. Furthermore, in the method for manufacturing the bonded body according to other embodiments, the bonding agent according to this embodiment is used. The bonding agent has an alkoxysilyl group as the OH generating group. Furthermore, a method for manufacturing a bonded body according to another embodiment comprises the steps of: (X') providing the bonding agent to the surface B of a substrate B having the polymer material B on its surface B, thereby causing the triazine ring and the alkoxysilyl group to appear on the surface B; and (YZ') obtaining the bonded body by applying an electroless plating solution to the triazine ring and the alkoxysilyl group on the surface B.

[0090] In the method for manufacturing the bonded body according to another embodiment, step (X') chemically bonds the substrate B with the compound (α) contained in the bonding agent according to this embodiment, causing a triazine ring and an alkoxysilyl group to appear on the surface of the substrate B. Furthermore, the aforementioned step (YZ') chemically bonds the metal material with the alkoxysilyl group, thereby increasing the bonding strength between the metal material and polymer material B. Furthermore, the aforementioned step (YZ') allows for coordination bonding between the metal material and the triazine ring, thereby increasing the bonding strength between the metal material and polymer material B.

[0091] In step (X'), the adhesive is applied to surface B by immersing surface B in the adhesive, spraying the adhesive onto surface B, or applying the adhesive to surface A using a coating device.

[0092] The electroless plating solution contains a metallic material. Examples of metal materials included in the electroless plating solution include Ni and Cu.

[0093] Furthermore, it is preferable to adsorb the catalyst onto the triazine ring or the alkoxysilyl group on surface B after step (X') and before step (YZ'). Examples of such catalysts include Pd and Ag.

[0094] The electroless plating solution preferably contains a reducing agent. Because the electroless plating solution contains a reducing agent, the electrons released by the oxidation of the reducing agent in step (YZ') facilitate the deposition of the metal material, and as a result, the bonding strength between the metal material and polymer material B can be further enhanced.

[0095] The bonding agent according to another embodiment is a bonding agent used for bonding a metal material and a polymer material B. Furthermore, the peel strength of the adhesive according to the other embodiment is 5 N / cm or more, preferably 6 N / cm or more, and more preferably 6 to 20 N / cm. In addition, in the adhesive according to other embodiments, the peel strength is the peel strength when peeled at a speed of 50 mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel".

[0096] Furthermore, the peel strength of the bonding agent according to the other embodiment after a solder reflow test at 260°C is preferably 5 N / cm or more, more preferably 6 N / cm or more, and even more preferably 6 to 20 N / cm. Note that the reflow test refers to the reflow method described in JIS C60068-2-58:2016.

[0097] As the aforementioned metal material, the metal material described as material A in this embodiment can be used. The bonding agent according to the other embodiment is preferably used for bonding copper foil having the metal material copper. The surface roughness (Rz) of the bonding surface of the copper foil is preferably 0.5 to 1.5 μm, more preferably 0.5 to 1.0 μm, and even more preferably 0.8 μm. Note that surface roughness (Rz) refers to the "arithmetic mean roughness of the surface" determined in accordance with JIS B0601:2013. Furthermore, the "arithmetic mean roughness of the surface" is the value obtained by summing the absolute values ​​of the deviations from the mean line to the measurement curve and averaging them over the reference length.

[0098] The polymer material B of this embodiment can be used as the polymer material B.

[0099] The bonding agent according to the other embodiment preferably contains compound (α) according to this embodiment.

[0100] Another embodiment of the jointed body is a jointed body in which a metal material and a polymer material B are joined together with a bonding agent. Furthermore, the peel strength of the jointed body according to the other embodiment is 5 N / cm or more, preferably 6 N / cm or more, and more preferably 6 to 20 N / cm. In addition, in the joint according to other embodiments, the peel strength is the peel strength when the metal material or polymer material is peeled at a speed of 50 mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel".

[0101] Furthermore, in the joint according to the other embodiment, the peel strength after a solder reflow test at 260°C is preferably 5 N / cm or more, more preferably 6 N / cm or more, and even more preferably 6 to 20 N / cm.

[0102] As the aforementioned metal material, the metal material described as material A in this embodiment can be used. In the other embodiment, it is preferable that the joined body is formed by joining copper foil having the aforementioned metallic material, copper. The surface roughness (Rz) of the bonding surface of the copper foil is preferably 0.5 to 1.5 μm, more preferably 0.5 to 1.0 μm, and even more preferably 0.8 μm.

[0103] In the joint according to other embodiments, the bonding agent preferably contains compound (α) according to this embodiment.

[0104] The bonding agent in the joint according to other embodiments may be the bonding agent according to this embodiment, or it may be the bonding agent according to other embodiments.

[0105] A printed circuit board according to another embodiment includes a bonding body according to another embodiment. [Examples]

[0106] Next, the present disclosure will be described in more detail with reference to examples and comparative examples. However, the present disclosure is not limited in any way to these examples.

[0107] (Example 1) (Synthesis 1: Formation of intermediates) A stirring bar and 10.0 g (54 mmol) of cyanuryl chloride (manufactured by Kanto Chemical Industry Co., Ltd.) were placed in a 500 mL three-necked flask. Next, a thermometer and a dropping funnel were attached to the three-necked flask. Then, the three-necked flask was subjected to a nitrogen atmosphere. Next, 100 mL of tetrahydrofuran (THF) was added to the three-necked flask, and the contents of the flask were cooled to -10°C. Then, a mixed solution of 11.95 g (54 mmol) of 3-aminopropyltriethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 20 mL of tetrahydrofuran (THF) (manufactured by Kanto Chemical Industry Co., Ltd.) was gradually added dropwise to the three-necked flask over a period of 30 minutes. Next, a mixed solution of 5.55 g (59.4 mmol) of triethylamine (TEA) (manufactured by Tokyo Chemical Industry Co., Ltd.) and 20 mL of tetrahydrofuran (THF) was gradually added dropwise to the three-necked flask over a period of 30 minutes. Then, while maintaining the temperature inside the three-necked flask at -10°C, the contents inside the three-necked flask were stirred using the stirring bar, and the intermediate 6-(3-triethoxysilylpropylamino)-1,3,5-triazine-2,4-dichloride was produced by the following reaction. The reactions that produce intermediates are shown below.

[0108] [ka]

[0109] After the reaction, the by-product triethylamine hydrochloride was filtered off from the contents of the three-necked flask. Then, the contents from which the by-product triethylamine hydrochloride had been filtered off were concentrated in a rotary evaporator and dried under reduced pressure to obtain purified 6-(3-triethoxysilylpropylamino)-1,3,5-triazine-2,4-dicloride.

[0110] (Synthesis 2: Formation of compound (α)) A stirring bar and 15.0 g (40.6 mmol) of purified 6-(3-triethoxysilylpropylamino)-1,3,5-triazine-2,4-dichloride were placed in a 300 mL three-necked flask. Next, a condenser and a dropping funnel were attached to the three-necked flask. Then, the three-necked flask was subjected to a nitrogen atmosphere. Next, 100 mL of tetrahydrofuran (THF) was added to the three-necked flask. Then, a mixed solution of 23.7 g (243.6 mmol) of diallylamine and 50 mL of tetrahydrofuran (THF) (manufactured by Kanto Chemical Industry Co., Ltd.) was gradually added dropwise to the three-necked flask over a period of 30 minutes. Next, the temperature inside the three-necked flask was gradually increased and reflux was performed inside the three-necked flask. While refluxing was occurring inside the three-necked flask, the contents inside the flask were stirred for 48 hours using the stirring bar, and compound (α), 2,4-bis(diallylamino)-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine, was produced by the following reaction. The reaction that produces compound (α) from the intermediate is shown below.

[0111] [ka]

[0112] After the reaction, the contents of the three-necked flask were cooled to room temperature. Then, the contents were filtered by suction using a filtration aid (product name: Celite) to obtain a filtrate. Next, the filtrate was concentrated using a rotary evaporator and dried under reduced pressure to obtain purified 2,4-bis(diallylamino)-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine.

[0113] (Preparation of bonding agent) A bonding agent was prepared by mixing compound (α), 2,4-bis(diallylamino)-6-(3-triethoxysilylpropyl)amino-1,3,5-triazine, with ethanol (EtOH) to obtain a compound (α) concentration of 0.1% by mass.

[0114] (Fabrication of the joint) As substrate A, two sheets of copper foil (ultra-low roughness, un-roughened electrolytic copper foil T9DA manufactured by Fukuda Metal Foil & Powder Industry Co., Ltd.) (30 mm x 60 mm) with a matte surface (Rz = 0.8 μm) were prepared. Furthermore, a prepreg sheet (30 mm x 60 mm) was prepared as substrate B (the resin composition in the prepreg sheet contains a modified polyphenylene ether (m-PPE) having carbon-carbon double bonds at its ends, and a peroxide as a radical initiator (polymerization initiator)). The elastic modulus of the copper foil is 120 GPa. The elastic modulus of the prepreg sheet is 2.6 GPa. Then, the two copper foils were immersed in the bonding agent for 1 minute, dried with a hairdryer, and then heated in an oven at 120°C for 10 minutes. Next, copper foil, prepreg sheet, and copper foil were laminated in this order and pressed in a press machine (pressing conditions: "177°C, 0.8 MPa, 30 minutes" → "216°C, 0.8 MPa, 60 minutes") to obtain a bonded body. Then, the joint was cut, and six 30mm x 10mm joints were created.

[0115] (Initial peel adhesion strength test) Using a single 30mm x 10mm bonded piece, the peel adhesive strength (hereinafter also referred to as "peel strength") was measured by peeling one of the copper foils at a speed of 50mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel adhesive strength - Part 1: 90-degree peel". The results are shown in Table 1 below.

[0116] (Steel adhesion strength test after solder reflow test) A solder reflow test (260°C) (hereinafter also simply referred to as "reflow test") was performed on five 30mm x 10mm bonded components. Then, similar to the initial peel adhesion strength test, the peel strength of the five 30mm x 10mm bonded pieces was measured after the reflow test. The results (arithmetic mean, n=5) are shown in Table 1 below.

[0117] (Comparative Example 1) A bonded body was prepared in the same manner as in Example 1, except that it was immersed in a bonding agent, dried with a dryer, and heated in an oven. An initial peel adhesion strength test and a peel adhesion strength test after solder reflow testing were then performed. The results are shown in Table 1 below.

[0118] (Comparative Example 2) A bond was prepared in the same manner as in Example 1, except that vinyltriethoxysilane was used instead of compound (α), and an initial peel adhesion strength test and a peel adhesion strength test after solder reflow were performed. The results are shown in Table 1 below.

[0119] (Comparative Example 3) A bond was prepared in the same manner as in Example 1, except that 3-acryloxypropyltrimethoxysilane was used instead of compound (α), and an initial peel adhesion strength test and a peel adhesion strength test after solder reflow were performed. The results are shown in Table 1 below.

[0120] [Table 1]

[0121] As shown in Table 1, Example 1, which is within the scope of this disclosure, showed higher peel strength in both the initial peel adhesion strength test and the peel adhesion strength test after the solder reflow test compared to Comparative Example 1, which did not use a bonding agent, and Comparative Examples 2 and 3, which did not use compound (α). From this, it can be seen that the bonding strength can be increased according to this disclosure. Furthermore, the peel strength at which substrate failure is considered to occur is 5 N / cm, and in Example 1, this value was exceeded.

[0122] Except for using copper foil with a matte surface roughness (Rz) of 1.1 μm (H-VLP2 grade) and copper foil with a matte surface roughness (Rz) of 1.4 μm (H-VLP grade), the same tests as described above for the "initial peel adhesion strength test" and the "peel adhesion strength test after solder reflow test" were performed. The results are shown in Table 2 below, along with the results in Table 1 above. The evaluation criteria for peel strength are as follows: "◎": 6.0N / cm or more "〇": 5.0 N / cm or more and less than 6.0 N / cm "×": Less than 5.0 N / cm

[0123] [Table 2]

[0124] As shown in Table 2, the embodiment using the bonding agent of Example 1, which is within the scope of this disclosure, showed higher peel strength in both the initial peel adhesion strength test and the peel adhesion strength test after the solder reflow test, compared to the embodiment without a bonding agent (corresponding to Comparative Example 1) and the embodiment using a bonding agent that does not contain compound (α) (bonding agents of Comparative Examples 2 and 3). From this, it can be seen that, according to this disclosure, even if the surface roughness (Rz) of the copper foil differs, the peel strength can be set to 5.0 N / cm or higher, and a bonded body with high bonding strength can be obtained.

Claims

1. One molecule contains an OH-generating group, an organic group containing a carbon-carbon double bond, and a triazine ring. The aforementioned OH generating group is an alkoxysilyl group, It is expressed by the following general formula (3), A compound having at least one of the following functional groups as the organic group containing the carbon-carbon double bond. CH 2 =CHNH-、 CH 2 =CH(CH 2 )NH-、 CH 2 =CH(CH 2 ) n2 NH-(n2=2~16) 、 CH 2 =CHCH 2 (N-)CH 2 CH=CH 2 、 CH 2 =C(CH 3 )CH 2 NH- CH 2 =CHCH 2 (N-)C(CH 3 ) 3 、 CH 2 =CHC 6 H 4 NH- CH 2 =CHC 6 H 4 CH 2 NH- CH 2 =C(CH 3 )(C=O)NH-、 CH 2 =CHCH 2 NH(C=O)NH-, C 6 H 5 (N-)CH 2 CH=CH 2 、 -NH(NH 2 )C 3 N 3 CH=CH 2 、 (CH 2 =CHCH 2 NO 2 CH=CH 2 ) 2 C 3 N 3 S-, (CH 2 =CHCH 2 NH) 2 C 3 N 3 S-, (CH 2 =CHCH 2 NO 2 CH=CH 2 )C 3 N 3 (SH)S-、 (CH 2 =CHCH 2 NH)C 3 N 3 (SH)S-、 【Chemistry 1】 (In the above general formula (3), J is an organic group containing a carbon-carbon double bond. The aforementioned R1 is H, a hydrocarbon group having 1 to 24 carbon atoms, or -RSi(R') ｎ１ (OR'') ３－ｎ１ And, R2 is -RSi(R') n1 (OR'') 3-n1, The aforementioned R is a chain-like, divalent hydrocarbon group having 1 to 12 carbon atoms. The R' is a chain-like hydrocarbon group having 1 to 4 carbon atoms. The R'' is H, or a chain-like hydrocarbon group having 1 to 4 carbon atoms. (The aforementioned n1 is an integer between 0 and 2.)

2. A bonding agent containing the compound described in claim 1.

3. The bonding agent according to claim 2, used for joining material A and polymer material B.

4. The bonding agent according to claim 3, wherein material A is a metallic material.

5. A bonded body comprising the material A and the polymer material B joined together with the bonding agent described in claim 3 or 4.

6. A printed circuit board comprising the bonded body described in claim 5.

7. A method for producing a bonded body, comprising joining a substrate A having material A on its surface A and a substrate B having polymer material B on its surface B with a bonding agent, The step (X) of applying the bonding agent according to claim 3 or 4 to the surface A, The process (Y) involves bringing the substrate A and the substrate B together so that surface A and surface B come into contact via the bonding agent, The process (Z) of obtaining the joined body by applying pressure to the contact surfaces of surface A and front surface B via the bonding agent, A method for manufacturing a joint, comprising:

8. The method for manufacturing a bonded body according to claim 7, further comprising step (A) of applying one or more treatments selected from the group consisting of degreasing, corona discharge treatment, plasma discharge treatment, ultraviolet irradiation, acid treatment, alkali treatment, steam treatment, and chemical conversion treatment to the surface A to generate OH groups on the surface A, prior to step (X).

9. A method for producing a bonded body according to claim 8, wherein after step (X), the surface A and the bonding agent are heated to chemically bond the OH groups of the surface A to at least one of the functional groups of the OH groups and OH-forming groups of the compound by dehydration condensation.

10. A method for manufacturing a bonded body according to any one of claims 7 to 9, wherein in step (X), the bond is applied to the surface A by immersing the surface A in the bond, spraying the bond onto the surface A, or applying the bond to the surface A with a coating device.

11. The method for manufacturing a bonded body according to any one of claims 7 to 10, wherein in (Z) above, pressure is applied to the contact surfaces of surface A and surface B via the adhesive so that the polymer material B and the adhesive come into contact.

12. A method for manufacturing a bonded body according to any one of claims 7 to 11, wherein the pressurization in step (Z) is performed under temperature conditions of 0 to 350°C.

13. The method for manufacturing a joined body according to any one of claims 7 to 12, wherein in step (Z), the contact surface is heated and pressurized.

14. A method for manufacturing a bonded body, wherein a metal material and a polymer material B are bonded together with a bonding agent, Using the bonding agent described in claim 4, The bonding agent has an alkoxysilyl group as the OH generating group, A step of providing the bonding agent to the surface B of a substrate B having the polymer material B on its surface B, thereby causing the triazine ring and the alkoxysilyl group to appear on the surface B, The process of obtaining the bonded body involves applying an electroless plating solution to the triazine ring and the alkoxysilyl group of the surface B, A method for manufacturing a joint, comprising:

15. A bonding agent used for joining a metal material and a polymer material B, The adhesive according to claim 2, wherein the peel strength is 5 N / cm or more when peeled at a speed of 50 mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel".

16. The bonding agent according to claim 15, wherein the peel strength after a solder reflow test at 260°C is 5 N / cm or more.

17. The bonding agent according to claim 15 or 16, used for joining copper foil having the aforementioned metallic material, copper.

18. The bonding agent according to claim 17, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.5 μm.

19. The bonding agent according to claim 17, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.0 μm.

20. The bonding agent according to claim 17, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.8 μm.

21. A bonded body comprising a metal material and a polymer material B joined together with the bonding agent described in claim 2, A bonded body having a peel strength of 5 N / cm or more when a metal material or polymer material is peeled at a speed of 50 mm / min in accordance with the method of JIS K6854-1:1999 "Adhesives - Test method for peel strength - Part 1: 90-degree peel".

22. The bonded body according to claim 21, wherein the peel strength after a solder reflow test at 260°C is 5 N / cm or more.

23. The bonded body according to claim 21 or 22, wherein copper foil having the aforementioned metallic material copper is joined together.

24. The bonded body according to claim 23, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.5 μm.

25. The bonded body according to claim 23, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.5 to 1.0 μm.

26. The bonded body according to claim 23, wherein the surface roughness (Rz) of the bonding surface of the copper foil is 0.8 μm.

27. A printed circuit board comprising a bonded body according to any one of claims 21 to 26.

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