Reactivity-imparting compound

Abstract

To provide a reactivity-imparting compound and a method for producing the reactivity-imparting compound, capable of suppressing photodegradation of a substrate and achieving high adhesion even without pretreatment.SOLUTION: According to the present disclosure, the reactivity-imparting compound comprises, in one molecule, reactive functional groups and diazirine groups, wherein the number of reactive functional groups is two or more, the number of diazirine groups is two or more, and the reactive functional group is selected from the group consisting of SH group, SNa group, amino group, trimethoxysilyl group, and triethoxysilyl group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a reactivity-imparting compound. [Background technology]

[0002] Composite materials in which different materials are bonded together, such as laminates in which a metal film is formed on an inorganic or polymer substrate, are used in circuit boards for mobile phones, vehicle components, and the like.

[0003] In a laminate, if the adhesion between materials is low, peeling occurs between the materials. Therefore, improving adhesion is an important characteristic of a laminate. One technique for improving the adhesion between materials is, for example, forming irregularities on the surface of the substrate. When part of the metal film penetrates into the irregularities on the surface of the substrate, an anchor effect is exerted, improving adhesion.

[0004] However, for example, if the surface of a substrate for a circuit board is uneven, the signal transmission distance increases and transmission loss occurs, making it difficult to use a technique for forming unevenness on the surface of a substrate for circuit board applications.

[0005] One technique for improving adhesion without forming surface irregularities is to introduce hydroxyl groups onto the substrate using corona discharge treatment, but corona discharge treatment can cause deterioration of the substrate and only introduces a small number of hydroxyl groups, so there is a limit to how much adhesion can be improved.

[0006] Another technique for improving adhesion without creating surface irregularities involves reacting a substrate surface with a compound that can impart reactivity to the substrate surface. For example, organofunctional silane compounds have been developed to improve the performance of laminates between polymeric materials and glass or metals. This method uses a coupling agent, i.e., a bifunctional molecule, that reacts with both the polymeric material and the bonding target (e.g., metal) to form a covalent bond. Specifically, silane coupling agents are organofunctional silane monomers with bifunctionality. This property allows the functional group at one end of the molecule to hydrolyze to form a silanol, which then bonds with similar functional groups on glass or OH groups on metal oxides through condensation. The other end of the silane molecule contains a functional group, such as an amino group or a mercapto group, that can react with organic materials. Thus, silane coupling agents are known to be extremely useful molecules for covalently bonding organic materials to other materials.

[0007] Patent Document 1 discloses a method for forming a metal film, comprising the steps of applying an agent containing a specific compound to the surface of a substrate and applying a metal film to the surface of the compound by wet plating, wherein the compound has an OH group or an OH-yielding group, an azide group, and a triazine ring in one molecule, and the substrate is constructed using a polymer. The technology in Patent Document 1 involves irradiating a molecule containing an azide group with ultraviolet light to generate a nitrene from the azide group, which then reacts with the substrate surface, thereby achieving high adhesion.

[0008] However, the technology of Patent Document 1 has the problem that the substrate deteriorates and adhesion decreases because a molecule having an azide group is irradiated with short-wavelength ultraviolet light. As a technology that can suppress substrate deterioration and improve adhesion, Patent Document 2 discloses a reactivity-imparting compound that has, in one molecule, a silane coupling moiety represented by a specific formula and a diazirine group. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] Patent No. 4936344 [Patent Document 2] International Publication No. 2022 / 097644 Summary of the Invention [Problem to be solved by the invention]

[0010] However, currently, there is a demand for higher adhesion than that achieved by the technique of Patent Document 2. Even when the technique of Patent Document 2 is used, pretreatment such as corona treatment is required for the substrate in order to achieve higher adhesion.

[0011] The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide a reactivity-imparting compound that suppresses photodegradation of a substrate and provides high adhesion regardless of whether or not a pretreatment is performed. [Means for solving the problem]

[0012] In order to solve the above problems, the present invention proposes the following means. (1) The reactivity imparting compound of the first aspect of the present invention is A reactive functional group and a diazirine group; and the number of reactive functional groups is 2 or more, the number of diazirine groups is 2 or more, The reactive functional group is at least one selected from the group consisting of an SH group, an SNa group, an amino group, a trimethoxysilyl group, and a triethoxysilyl group. (2) Aspect 2 of the present invention is the reactivity imparting compound of Aspect 1, The compound may be a compound represented by the following formula (1). [ka] [ka] [ka] [ka] [ka] [ka] [Z in the above formula (1) 1 , Z 2 represents a triazine ring, a benzene ring, or a nitrogen atom; A represents an acetylene group or the first structure represented by the above formula (2); n is 0 or 1; when n is 0, Z 1 and Z 2 is directly bonded, and Q 1 , Q 2 , Q 3 , and Q 4 At least two of Q are the reactive functional group or the second structure represented by the formula (3), 1 , Q 2 , Q 3 , and Q 4 At least two of the above are the third structure represented by the formula (4), and * in the formula (2) represents an adjacent carbon atom or nitrogen atom, and X 1 and X 2 represents O, NH, or S; m1 represents an integer of 1 to 10; * in the above formula (3) represents an adjacent carbon atom or nitrogen atom; X 3 represents O, NH, or S; m2 represents an integer of 1 to 10; Y 1 represents an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group, * in the above formula (4) represents an adjacent carbon atom or nitrogen atom, and X 4 represents O, NH, S, or CH2; m3 is an integer of 0 to 10; Y 2is a fourth structure represented by the above formula (5) or a fifth structure represented by the above formula (6), in which * represents an adjacent carbon atom, and R 1 is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group, * in the above formula (6) represents an adjacent carbon atom, Ar is an arylene group, a divalent heterocyclic group, or a methylene group, and R 2 is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group. (3) Aspect 3 of the present invention is the reactivity imparting compound of Aspect 2, Said Z 1 is a triazine ring, and said Z 2 may be a nitrogen atom. (4) A fourth aspect of the present invention is the reactivity imparting compound of the third aspect, It may be a compound represented by the following formula (7). [ka] (5) A fifth aspect of the present invention is the reactivity imparting compound of the third aspect, It may be a compound represented by the following formula (8). [ka] (6) A sixth aspect of the present invention is the reactivity imparting compound of the third aspect, It may be a compound represented by the following formula (9). [ka] (7) A seventh aspect of the present invention is the reactivity imparting compound of the second aspect, Said Z 1 is a triazine ring, and Z 2 However, it may also be a triazine ring. (8) In an eighth aspect of the present invention, the reactivity imparting compound of the seventh aspect may be a compound represented by the following formula (10). [ka] (9) A ninth aspect of the present invention is the reactivity imparting compound of the seventh aspect, It may be a compound represented by the following formula (11). [ka] (10) A tenth aspect of the present invention is the reactivity imparting compound of the seventh aspect, It may be a compound represented by the following formula (12). [ka] (11) Aspect 11 of the present invention relates to the reactivity imparting compound of aspect 7, It may be a compound represented by the following formula (13). [ka] (12) Aspect 12 of the present invention relates to the reactivity imparting compound of aspect 7, It may be a compound represented by the following formula (14). [ka] (13) Aspect 13 of the present invention relates to the reactivity imparting compound of aspect 7, It may be a compound represented by the following formula (15). [ka] (14) Aspect 14 of the present invention relates to the reactivity imparting compound of aspect 1, It may be a compound represented by the following formula (16). [ka] [ka] [ka] [X in the above formula (16) 5 and X 6 represents O, NH, or S; m4 represents an integer of 1 to 10; R 3 is the reactive functional group or the sixth structure represented by the formula (17), and R 4 is the seventh structure represented by the above formula (18), and * in the above formula (17) represents an adjacent carbon atom, and X 7 represents O, NH, or S; m5 represents an integer of 1 to 10; Y 3 is an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group. [Effects of the Invention]

[0013] According to the above-described aspect of the present invention, it is possible to provide a reactivity-imparting compound that suppresses photodegradation of a substrate and provides high adhesion regardless of whether or not a pretreatment is performed. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a cross-sectional view of a laminate using a reactivity imparting compound according to an example of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0015] The reactivity-imparting compound according to the embodiment of the present invention will be described below, but the present invention is not limited to the following embodiment.

[0016] (Reactivity-imparting compound) The reactivity imparting compound according to this embodiment has a reactive functional group and a diazirine group in one molecule, the number of reactive functional groups is two or more, the number of diazirine groups is two or more, and the reactive functional group is one or more selected from the group consisting of an SH group, an SNa group, an amino group, a triethoxysilyl group, and a trimethoxysilyl group.

[0017] The reactivity imparting compound according to this embodiment has two or more reactive functional groups. The reactive functional group is one or more selected from the group consisting of an SH group, an SNa group, an amino group, a trimethoxysilyl group, and a triethoxysilyl group. The reactive functional group improves adhesion to metals, rubber, resins, ceramics, and the like. The thiol group (SH group) and the SNa group improve adhesion to Au, Ag, Cu, and rubber. Therefore, when improving adhesion to Au, Ag, Cu, and rubber, the SH group and the SNa group are preferred as reactive functional groups. Furthermore, the thiol group and the SNa group have excellent storage stability, facilitating long-term storage of the reactivity imparting compound. The presence of the thiol group and the SNa group can improve the solubility of the reactivity imparting compound in a basic aqueous solution. This allows the use of water, which has a low environmental impact, as a solvent. Similarly, amino groups are likely to support Pd and other catalysts for forming plating. This facilitates the formation of a plating layer with high adhesion. Therefore, when forming a plating layer, amino groups are preferred as reactive functional groups. Furthermore, amino groups have excellent storage stability, making it easier to store the reactivity-imparting compound for long periods of time. Having an amino group in the reactivity-imparting compound improves the solubility of the reactivity-imparting compound in an acidic aqueous solution. This allows the use of water, which has a low environmental impact, as a solvent. Trimethoxysilyl groups and trimethoxysilyl groups generate silanol groups upon hydrolysis. The generated silanol groups react with metals, resins, etc., covered with oxides or hydroxides, improving adhesion. Therefore, trimethoxysilyl groups and triethoxysilyl groups are particularly preferred as reactive functional groups when the metal surface is covered with an oxide, when the resin has been subjected to surface treatment such as corona discharge, or when the material is ceramics. The silanol group also has the ability to support precious metals that serve as plating catalysts. Furthermore, the adhesion between metals and rubber, resins, ceramics, etc. improves with the number of reactive functional groups in the reactivity-imparting compound. To improve adhesion between metals and rubber, resins, ceramics, etc., it is preferable to increase the number of reactive functional groups.

[0018] The reactivity imparting compound according to this embodiment has two or more diazirine groups. The diazirine group is chemically stable and generates a carbene upon irradiation with ultraviolet light or heat. The carbene is highly reactive and can form a covalent bond with a molecule in the vicinity of the carbene. Therefore, after applying the reactivity imparting compound according to this embodiment to a substrate surface, a covalent bond can be formed between the substrate and the reactivity imparting compound by irradiating light or heating. This allows for high adhesion between the substrate and the reactivity imparting compound according to this embodiment. Furthermore, since carbenes can provide higher adhesion than nitrenes generated from azide groups, they can provide higher adhesion than conventional reactivity imparting compounds that use azide groups. Furthermore, diazirine groups have an absorption band at a longer wavelength than azide groups and diazomethyl groups that generate carbene, and therefore can suppress photodegradation of substrates (e.g., resin substrates). Adhesion to substrates improves as the number of diazirine groups in the reactivity imparting compound increases. In cases where a substrate with poor adhesion is used, it is preferable to increase the number of diazirine groups.

[0019] The reactivity imparting compound is not particularly limited as long as it has a reactive functional group and a diazirine group in one molecule, the number of reactive functional groups is two or more, the number of diazirine groups is two or more, and the reactive functional group is one or more selected from the group consisting of an SH group, an SNa group, an amino group, a triethoxysilyl group, and a trimethoxysilyl group. For example, when the number of reactive functional groups and the number of diazirine groups are equal, the reactivity imparting compound is preferably a compound represented by the following formula (1):

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] In the above formula (1), Z 1 , Z 2 represents a triazine ring, a benzene ring, or a nitrogen atom. 1 , Z 2 At least one of Z is preferably a triazine ring or a benzene ring.1 , Z 2 Z in the above formula (1) functions as a spacer between the reactive functional group and the diazirine group. 1 , Z 2 The bonding position of the reactive functional group and the diazirine group can be adjusted. This allows the adhesion between the substrate and the coating layer described later to be adjusted. In order to facilitate production and adjust the positional relationship between the diazirine group and the reactive functional group, Z 1 , Z 2 is preferably a triazine ring or a nitrogen atom. The triazine ring may be any of 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine, with 1,3,5-triazine being particularly preferred. Z in the above formula (1) 1 , Z 2 If is a benzene ring, A, Q 1 , Q 2 , Q 3 , and Q 4 The bonding positions of A, Q and X are not particularly limited, but are preferably 1-, 3-, and 5-positions. 1 , Q 2 , Q 3 , and Q 4 The other portion is not particularly limited and may be a hydrogen atom or any functional group.

[0027] A is an acetylene group or the first structure represented by the above formula (2), n is 0 or 1, and when n is 0, Z 1 and Z 2 A is directly bonded to Z 1 and Z 2 By adjusting the distance between the carbon atom and the coating layer, the number of bonds with the substrate or coating layer per unit area can be adjusted. In the above formula (2), * represents an adjacent carbon atom or nitrogen atom, and X 1 and X 2 represents O, NH, or S, and m1 represents an integer of 1 to 10. X 1 and X 2 is preferably O or NH in terms of chemical stability. 1 and X 2may be the same or different. The integer m1 represents the length of the spacer between the reactive functional group and the diazirine group. By adjusting the value of m1, the number of bonds with the substrate or coating layer per unit area can be adjusted.

[0028] Q in the above formula (1) 1 , Q 2 , Q 3 , and Q 4 At least two of the structures Q contain reactive functional groups (reactive structures). 1 , Q 2 , Q 3 , and Q 4 At least two of the reactive structures are preferably the reactive functional group or the second structure represented by the above formula (3). The reactive structures may be the same or different. In the above formula (3), * represents an adjacent carbon atom or nitrogen atom, and X 3 represents O, NH, or S, and m2 represents an integer of 1 to 10. X 3 is preferably O or NH in terms of chemical stability. The integer m2 represents the length of the spacer between the reactive functional group and the diazirine group. By adjusting the value of m2, the frequency of contact between the coating layer and the reactive functional group can be adjusted. In the above formula (3), m2 is preferably an integer of 1 to 10. Y 1 is an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group. Y in each reactive structure 1 may be the same or different, but are preferably the same in order to improve adhesion to the coating layer.

[0029] Q in the above formula (1) 1 , Q 2 , Q 3 , and Q 4 At least two of the structures contain a diazirine group (diazirine structure). 1 , Q 2 , Q 3 , and Q 4At least two of the above are preferably the third structure represented by the above formula (4). In the above formula (4), * represents an adjacent carbon atom or nitrogen atom, and X 4 represents O, NH, S, or CH2. X 4 is preferably O, NH, or CH2 in terms of chemical stability. m3 is an integer of 0 to 10. The integer m3 represents the length of the spacer between the reactive functional group and the diazirine group. By adjusting the number of m3, the contact frequency between the substrate and the diazirine group can be adjusted. Y in the above formula (4) 2 is the fourth structure represented by the above formula (5) or the fifth structure represented by the above formula (6). Y in each diazirine structure 2 may be the same or different.

[0030] In the above formula (5), * represents an adjacent carbon atom, and R 1 is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group. 1 is preferably a trifluoromethyl group or a pentafluoroethyl group, since the photoreaction efficiency is improved.

[0031] In the above formula (6), * represents an adjacent carbon atom, Ar is an arylene group, a divalent heterocyclic group, or a methylene group, and R 2 is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group. 2 is preferably a trifluoromethyl group or a pentafluoroethyl group, since the photoreaction efficiency is improved.

[0032] Examples of the arylene group for Ar in the above formula (6) include a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, and a 2,6-naphthylene group.

[0033] The divalent heterocyclic group of Ar in the following formula (6) includes a divalent group obtained by removing two hydrogen atoms from the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting a heterocycle such as furan, thiophene, or pyridine.

[0034] Z 1 is a triazine ring, and Z 2 Specific examples of the above formula (1) when is a nitrogen atom include N represented by the following formula (7): 2 , N 4 -bis((3-triethoxysilyl)propyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine, 6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-dithiol represented by the following formula (8), N-(2-hydroxybenzoyl)-1,3,5-triazine-2,4-dithiol represented by the following formula (9), 2 ,N 4 -bis(2-aminoethyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine, etc. To improve adhesion to metals, resins, or ceramics covered with oxides or hydroxides, N-type amines represented by the following formula (7) are used. 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine is preferred. To improve adhesion to Au, Ag, Cu, rubber, etc., -(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-dithiol represented by the following formula (8) is preferred. To improve adhesion to a plating layer catalyzed by Pd, etc., N-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-dithiol represented by the following formula (9) is preferred. 2 ,N 4 -bis(2-aminoethyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine is preferred.

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] Z in the above formula (1) 1 is a triazine ring, and Z 2 When Z is a triazine ring, specific examples of the compound (1) include compounds represented by the following formulas (10) to (15): 1 is a triazine ring, and Z 2 However, the triazine ring has the effect of easily introducing a substituent into the aromatic ring, thereby improving productivity. Furthermore, it is preferable that the triazine ring has one diazirine group and one reactive functional group. This configuration facilitates bonding to the substrate more easily than when one triazine ring has two diazirine groups. To improve adhesion to metals or resins covered with oxides or hydroxides, or to ceramics, etc., compounds represented by the following formulas (10) and (13) are preferred. To improve adhesion to plating layers using Pd or the like as a catalyst, compounds represented by the following formulas (11) and (14) are preferred. To improve adhesion to Au, Ag, Cu, rubber, etc., compounds represented by the following formulas (12) and (15) are preferred.

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] For example, when the number of reactive functional groups and the number of diazirine groups are different, the reactivity-imparting compound is preferably a compound represented by the following formula (16): The reactivity-imparting compound represented by the following formula (16) has four diazirine groups and two reactive functional groups, and therefore can further improve adhesion to the substrate.

[0046] [ka]

[0047] [ka]

[0048] [ka]

[0049] X in the above formula (16) 5 and X 6 represents O, NH, or S. X 5 and X 6 is preferably O or NH in terms of chemical stability. 5 and X 6may be the same or different. m4 represents an integer of 1 to 10. R 3 is the reactive functional group or the sixth structure represented by the formula (17), and R 4 is the seventh structure represented by the above formula (18). The seventh structure has two diazirine groups. The integer m4 represents the length of the spacer between the reactive functional group and the diazirine group. By adjusting the value of m4, the number of bonds with the substrate or coating layer per unit area can be adjusted.

[0050] * in (14) above represents the adjacent carbon atom, and X 7 represents O, NH, or S; m5 represents an integer of 1 to 10; Y 3 is an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group. 7 In terms of chemical stability, Y is preferably O or NH. 3 may be the same or different, but are preferably the same in order to improve adhesion to the coating layer.

[0051] (Action of reactivity-imparting compound) The reactivity imparting compound according to this embodiment has a diazirine group, which is a photo- and heat-reactive nitrogen functional group, and a reactive functional group. The diazirine group is photodecomposed by light (wavelength around 360 nm) to generate a highly reactive chemical species, carbene (carbon with six valence electrons and no charge). In addition to light, heat (80°C to 180°C) also generates carbene. The carbene moiety forms a covalent bond with the substrate surface of the laminate. After forming the covalent bond, the reactive functional group of this reactivity imparting compound is fixed to the surface of the substrate (e.g., a resin substrate). This imparts reactivity that allows bonding with other materials (e.g., a coating layer) via the reactive functional group.

[0052] Furthermore, the reactivity-imparting compound having a diazirine group of this embodiment has higher bonding strength than conventional compounds having an azide group. When a resin substrate to which reactivity has been imparted with the reactivity-imparting compound is metal-plated, the reactivity-imparting compound of this embodiment is less likely to cause metal peeling than conventional compounds having an azide group. Furthermore, since the reactivity-imparting compound has two or more diazirine groups and two or more reactive functional groups, high adhesion can be obtained without pretreatment or the like.

[0053] (Method of producing reactivity-imparting compound) The reactivity imparting compound of this embodiment can be appropriately produced, for example, by introducing a reactive functional group and a diazirine moiety into a compound having a triazine ring or a benzene ring. Here, a trihalogenated triazine ring will be described as an example, but a benzene ring can also be synthesized using a chemical reaction. A trihalogenated triazine ring refers to a triazine ring in which three hydrogen atoms are substituted with halogen. Chlorine is preferred as the substituted halogen. Examples of compounds having a trihalogenated triazine ring include cyanuric chloride, 3,5,6-trichloro-1,2,4-triazine, and 4,5,6-trichloro-1,2,3-triazine.

[0054] The method for producing the reactivity imparting compound according to this embodiment includes a diazirine group imparting step of reacting a compound having a trihalogenated triazine ring with a compound having a hydroxyl group and a diazirine group to obtain a diazirine group imparting compound, and a reactive functional group imparting step of reacting the diazirine group imparting compound with a compound having a reactive functional group. Here, an example is described in which cyanuric chloride in which 1,3,5-triazine is chlorinated is used as the compound having a trihalogenated triazine ring, but the reactivity imparting compound according to this embodiment can also be obtained by a similar reaction in the case of compounds having other trihalogenated triazine rings.

[0055] <Diazirine Group Addition Step> In the diazirine group-imparting step, cyanuric chloride is reacted with a compound having a hydroxyl group and a diazirine group to obtain a diazirine group-imparted compound, such as bis-[3-(trifluoromethyl)-3H-diazirine-3-yl]benzylamine.

[0056] The synthesis using bis-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine is described below. For example, the reaction is as shown in the following formula (19). In the following formula (19), DIEA represents N,N-diisopropylethylamine. A base other than diisopropylethylamine may be used in the reaction of the following formula (19). In the reaction of the following formula (19), for example, pyridine, triethylamine, etc. can be used instead of N,N-diisopropylethylamine. In the reaction of the following formula (19), 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine can be obtained as the diazirine group-imparting compound.

[0057] [ka]

[0058] <Reactive Functional Group Addition Step> In the reactive functional group imparting step, the diazirine group imparting compound obtained in the diazirine group imparting step is reacted with a compound having an amino group and a reactive functional group. The reactive functional group of the compound having an amino group and a reactive functional group may be protected with a protecting group. The reactive functional group imparting step can be used to obtain the reactivity imparting compound according to this embodiment. If the reactive functional group is protected with a protecting group, the reactivity imparting compound according to this embodiment can be obtained by deprotecting the reactive functional group after the reactive functional group imparting step (deprotection step).

[0059] Examples of compounds having an amino group and a reactive functional group include 3-aminopropyltriethoxysilane and N-(t-butoxycarbonyl)-1,2-diaminoethane.

[0060] An example of the reaction between 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine synthesized by the above formula (19) and 3-aminopropyltriethoxysilane is shown in the following formula (20). In the following formula (20), DIEA represents N,N-diisopropylethylamine. A base other than diisopropylethylamine may be used in the reaction of the following formula (20). In the reaction of the following formula (20), for example, pyridine, triethylamine, etc. may be used instead of N,N-diisopropylethylamine. Through the reaction of the following formula (20), N 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine can be obtained.

[0061] [ka]

[0062] An example of the reaction between 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine synthesized by the above formula (19) and N-(t-butoxycarbonyl)-1,2-diaminoethane is shown in the following formula (21). In the following formula (21), DIEA represents N,N-diisopropylethylamine. A base other than diisopropylethylamine may be used in the reaction of the following formula (21). In the reaction of the following formula (21), for example, pyridine, triethylamine, etc. can be used instead of N,N-diisopropylethylamine. Through the reaction of the following formula (21), N 2 ,N 4-bis(2-Nt-butoxycarbonylamino)ethylamino)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine can be obtained.

[0063] [ka]

[0064] <Deprotection process> N obtained by the reaction of the above formula (21) 2 ,N 4 -bis(2-Nt-butoxycarbonylamino)ethylamino)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine is protected with an amino group. When the reactive functional group is protected with a protecting group, a reactivity imparting compound can be obtained by deprotection. The deprotection method can be appropriately selected depending on the type of protecting group. For example, when the amino group is protected with a tert-butoxycarbonyl (Boc) group, it can be deprotected with trifluoroacetic acid (TFA) as in the reaction of the following formula (22). In this way, the reactivity imparting compound according to this embodiment can be obtained.

[0065] [ka]

[0066] (Laminate) A laminate using the reactivity imparting compound according to this embodiment will now be described. As shown in Fig. 1, a laminate 100 according to this embodiment of the present invention includes a substrate 10, a reactivity imparting compound layer 20, and a coating layer 30. Each component will be described below.

[0067] (base material) Examples of materials for the substrate 10 include inorganic materials such as ceramics and glass, and resins. The form of the substrate 10 is not particularly limited, and may be plate-like or granular.

[0068] The resin of the substrate 10 may be a curable resin (e.g., thermosetting resin, photocurable resin, or electron beam curable resin), a thermoplastic resin, a fiber-reinforced resin, rubber (vulcanized rubber), or other material having a coating film containing these polymers on its surface. Specific examples of resins include acrylonitrile butadiene styrene (ABS) resin. ABS resin is used for vehicle components and is used in laminates having ABS-to-metal bonded portions when metal plating is applied to the surface. Resins used for circuit boards include epoxy resin, polyimide resin, fluorine-based resin, polyphenylene ether resin (PPE), cycloolefin polymer (COP), polypropylene (PP), polyphenylene sulfide (PPS), and liquid crystal polymer. However, resins with low dielectric constants and dielectric loss tangents are used for high-speed communications.

[0069] When the laminate 100 is used as a high-frequency printed wiring board, materials with small dielectric properties (dielectric constant, dielectric loss tangent), such as COP, PP, PPE, fluorine-based resin, and liquid crystal polymer, are desirable. However, if wiring is formed on a smooth surface, there is a problem with adhesion to metals. However, by using the reactivity-imparting compound according to this embodiment, adhesion to metals can be improved even when the surface is smooth.

[0070] Examples of inorganic materials for the substrate 10 include materials containing silicon oxide such as glass, alumina, zirconia, etc. In addition, components of electronic devices and circuit boards include substrates containing various inorganic and organic materials, and are used as laminates by forming circuits on the surfaces by metal plating or the like.

[0071] When the substrate 10 is made of resin, it may contain inorganic particles such as talc, a lubricant, an antistatic agent, etc., depending on the purpose of improving the mechanical strength and surface properties.

[0072] When the laminate 100 is used as a printed wiring board, its thickness is not particularly limited. However, for example, when the substrate 10 is used as a flexible wiring board, the thickness of the substrate 10 is preferably 1 μm or more and 200 μm or less. If the thickness of the substrate 10 is less than 1 μm, the mechanical strength of the substrate 10 may be insufficient, which is not preferred. The thickness of the substrate 10 is more preferably 3 μm or more. Furthermore, if the thickness of the film exceeds 200 μm, the foldability may decrease, which is not preferred. The thickness of the substrate 10 is more preferably 150 μm or less.

[0073] When the laminate 100 is used as a high-frequency printed wiring board, the arithmetic mean roughness Ra of the substrate 10 is, for example, 0.01 to 1 μm. If the arithmetic mean roughness Ra is between 0.01 μm and 1 μm, it can accommodate miniaturized circuits. Furthermore, if the arithmetic mean roughness Ra is 0.2 μm or less, transmission loss in the high-frequency range can be reduced. The arithmetic mean roughness Ra can be measured in accordance with JIS B 0601:2013.

[0074] (Reactivity imparting compound layer 20) The reactivity imparting compound layer 20 is provided on the substrate 10 and is composed of the reactivity imparting compound according to this embodiment. Here, "provided on the substrate 10" not only means providing the reactivity imparting compound layer 20 so as to be in contact with the surface of the substrate 10, but also includes providing an intermediate layer between the substrate 10 and the reactivity imparting compound layer 20.

[0075] The thickness of the reactivity imparting compound layer 20 is not particularly limited as long as it covers the entire surface of the substrate 10. The thickness of the reactivity imparting compound layer 20 may be, for example, equal to or greater than the thickness of a single molecule (a monomolecular layer or greater) of the reactivity imparting compound that constitutes the reactivity imparting compound layer 20. The upper limit of the thickness of the reactivity imparting compound layer 20 is not particularly limited, but is, for example, 400 nm or less.

[0076] (covering layer) The coating layer 30 is provided on the reactivity imparting compound layer 20. The coating layer 30 is made of, for example, a metal, a resin, an inorganic insulating material, etc. Examples of metals for the coating layer 30 include gold (Au), silver (Ag), tin (Sn), copper (Cu), and copper alloys. Examples of resins for the coating layer 30 include rubber, liquid crystal polymer, epoxy resin, and silicone resin. Examples of inorganic insulating materials for the coating layer 30 include ceramics, glass, and quartz. When the laminate 100 is a printed circuit board, the metal constituting the covering layer 30 is preferably Cu or a Cu alloy, which has high electrical conductivity, from the viewpoint of power loss and transmission loss.

[0077] The thickness of the coating layer 30 is not particularly limited, but is, for example, 0.1 μm to 50 μm. More preferably, the thickness of the coating layer 30 is 2 μm to 10 μm. If the thickness of the coating layer 30 is 0.1 μm to 50 μm, sufficient mechanical strength can be obtained.

[0078] (Method of manufacturing laminate) A method for producing the laminate according to this embodiment will be described below, but the method for producing the laminate according to this embodiment is not limited to the following method.

[0079] When producing the laminate according to this embodiment, first, a reactivity imparting compound layer 20 made of the reactivity imparting compound according to this embodiment is formed on a substrate 10. The method for forming the reactivity imparting compound layer 20 is not particularly limited. For example, the reactivity imparting compound layer 20 may be formed by applying a solution containing the reactivity imparting compound to the surface of the substrate 10. Alternatively, the reactivity imparting compound layer 20 may be formed by immersing the substrate 10 in a solution containing the reactivity imparting compound.

[0080] When a solution containing a reactivity-imparting compound is used, the solvent can be appropriately selected from water, an organic solvent, etc. Specifically, the solvent may be water, an alcohol, a ketone, an aromatic hydrocarbon, an ester, an ether, etc. The reactivity-imparting compound may be dispersed in the solvent without dissolving. When a solution is used, the solvent in the solution may be dried by air drying, heating, etc.

[0081] A reactivity amplifier may be added to the solution containing the reactivity-imparting compound. Examples of the reactivity amplifier include compounds that contribute to other bonding, such as silane coupling agents. Examples of other reactivity amplifiers include photosensitizers, such as benzophenone.

[0082] After forming the reactivity imparting compound layer 20 on the substrate 10, energy is applied to generate carbene from the diazirine group of the reactivity imparting compound. This carbene reacts with the substrate 10, resulting in high adhesion between the reactivity imparting compound layer 20 and the substrate 10.

[0083] The energy can be applied by, for example, light irradiation. The diazirine group of the reactivity imparting compound of this embodiment is activated in response to a wide range of wavelengths, but the light is preferably on the long wavelength side in order to suppress deterioration of the substrate due to light. Specifically, the wavelength is preferably 300 nm or more, and preferably 400 nm or less. For light irradiation, an existing light irradiation device can be used as appropriate. Alternatively, the energy can be applied by heating. The heating temperature is preferably 80°C to 180°C. As the energy application method, light irradiation and heating may be used in combination.

[0084] Energy is applied to the reactivity-imparting compound layer 20 to improve the adhesion between the substrate 10 and the reactivity-imparting compound layer 20, and then the coating layer 30 is provided. The coating layer 30 may be provided by plating or the like, or by bonding a metal plate or foil. In the case of bonding, the same reactivity-imparting compound may be applied to the surface of the metal plate or foil that will be bonded to the substrate 10, and energy may be applied to achieve adhesion. As the plating method, a dry plating method (vapor deposition or sputtering) or a wet plating method may be appropriately selected, or both may be used in combination. When forming the coating layer 30, it is preferable to use wet plating such as electroless plating or electroplating to form a metal thin film. Before forming the coating layer 30, a conventionally known pretreatment process for plating may be performed. [Example]

[0085] Next, examples of the present invention will be described, but the conditions in the examples are merely examples adopted to confirm the feasibility and effects of the present invention, and the present invention is not limited to these examples. Various conditions can be adopted in the present invention as long as they do not deviate from the gist of the present invention and the object of the present invention is achieved.

[0086] (Test conditions) The following instruments and reagents were used for the synthesis of samples and the analysis of the synthesized samples. ·Analytical equipment Nuclear magnetic resonance spectrum: JEOL JNM-ECA500 NMR measurement device (500 MHz) ·reagent Various reagents: Commercially available reagents were used and purified by standard methods as necessary. Various reaction solvents: dried and purified by standard methods as necessary. Silica gel: Wako-gel C-200 (Wako Pure Chemical Industries, Ltd.), Silica gel 60N (Kanto Chemical Co., Ltd.)

[0087] The synthesis method of the sample will be explained below.

[0088] (Synthesis of Intermediate 1) A 25 mL two-necked recovery flask was purged with argon and charged with sodium tert-butoxide (19.2 mg, 0.20 mmol, 1.00 eq.), dehydrated dimethylformamide (DMF) (1.0 mL), and 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine hydrochloride (50.3 mg, 0.20 mmol, 1.00 eq.) and cooled to -20 °C. 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl bromide (55.8 mg, 0.20 mmol, 1.00 eq.) dissolved in dehydrated DMF (2.5 mL) was slowly added dropwise and stirred overnight at -20 °C. After stirring, 1N aqueous sodium hydroxide solution was added and the mixture was extracted with toluene. The organic layer was dried over anhydrous sodium sulfate, filtered, removed the solvent, and dried under vacuum. The obtained crude product was separated and purified by silica gel column chromatography using hexane:ethyl acetate=7:1 as a developing solvent to obtain intermediate 1 (bis-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine) (40.2 mg, 9.73×10 -2 1 mmol, yield 49%) was obtained as a yellow liquid.

[0089] The results of nuclear magnetic resonance spectroscopy of the obtained intermediate 1 are shown below. 1 H NMR (500MHz, CDCl3 ) :δ7.37(d,J=8.0Hz,4H),δ7.15(d,J=8.0Hz,4H),δ3.79(s,4H). 13 C NMR (126 MHz, CDCl3): δ141.9,128.5,127.8,126.5,123.2,121.0,52.4. 19 F NMR (471 MHz, CDCl3):δ-63.4.

[0090] (Synthesis of Intermediate 2) A 25 mL two-necked recovery flask was purged with argon and charged with anhydrous dichloromethane (3.0 mL), cyanuric chloride (60.2 mg, 0.33 mmol, 1.50 eq.), and N,N-diisopropylethylamine (146 mg, 1.13 mmol, 5.20 eq.), followed by cooling to 0°C. Intermediate 1 (90.0 mg, 0.22 mmol, 1.00 eq.) dissolved in anhydrous dichloromethane (2.0 mL) was slowly added dropwise, and the mixture was stirred at 0°C for 3 hours. After stirring, water was added, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent removed, and then vacuum dried. The obtained crude product was separated and purified by silica gel column chromatography using hexane:ethyl acetate=15:1 as a developing solvent to obtain intermediate 2 ((4,6-dichloro-1,3,5-triazin-2-yl)-bis-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine) (114 mg, 0.20 mmol, yield 93%) as a yellow liquid.

[0091] The results of nuclear magnetic resonance spectroscopy of the obtained intermediate 2 are shown below. 1 H NMR (500MHz, CDCl3): δ7.23(d,J=8.6Hz,4H), δ7.17(d,J=8.0Hz,4H),δ4.79(s,4H). 13 C NMR (126MHz, CDCl3): δ170.8,165.7,136.9,129.2, 128.4,127.0,123.1,120.9,49.1. 19 F NMR (471 MHz, CDCl3): δ -66.4.

[0092] (Synthesis of reactivity imparting compound of Example 1) Intermediate 2 (56.1 mg, 0.10 mmol, 1.00 eq.) was added and the mixture was placed under an argon atmosphere. Anhydrous 1,4-dioxane (1.00 mL), 3-aminopropyltriethoxysilane (221.4 mg, 1.00 mmol, 10.00 eq.), and diisopropylethylamine (38.8 mg, 0.30 mmol, 3.00 eq.) were added, and the mixture was heated to 65°C and stirred for 3 hours in the dark. After stirring, water was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was removed and dried under vacuum to obtain a yellow liquid as a crude product. The crude product was separated and purified by silica gel column chromatography using toluene:acetone = 20:1 as a developing solvent to obtain the reactivity imparting compound (N 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine) (41.2 mg, 0.047 mmol, 44% yield) was obtained as a yellow liquid.

[0093] The results of nuclear magnetic resonance spectroscopy of the reactivity imparting compound of Example 1 obtained are shown below. 1 H NMR (500MHz, CDCl3): δ7.28-7.18(brm,4H), δ7.10(d,J=8.0Hz,4H),δ5.02(brs,2H),δ4.71 (brs,4H),3.79(brs,12H),3.31(brs,4H),1.64 (brs,4H),1.20(brs,J=7.2Hz18H),0.62(brs, 4H). 19 F NMR (471 MHz, CDCl3): δ -65.2.

[0094] (Synthesis of reactivity imparting compound of Example 2) In a 20 mL Schlenk tube, add (4,6-dichloro-1,3,5-triazin-2-yl)-bis-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine (35 mg, 6.24×10 -2The mixture was then placed under an argon atmosphere. Anhydrous 1,4-dioxane (1.00 mL), N-(t-butoxycarbonyl)-1,2-diaminoethane (150 mg, 0.93 mmol, 15 eq.), and diisopropylethylamine (24.2 mg, 0.18 mmol, 3.0 eq.) were added and stirred at 30 °C for 12 hours in the dark. After stirring, water was added and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and filtered, after which the solvent was removed and the mixture was dried under vacuum to obtain a crude product. The crude product was separated and purified by silica gel column chromatography using acetone:toluene = 1:5 as a developing solvent to obtain N 2 ,N 4 -bis(2-N-tert-butoxycarbonylamino)ethylamino)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine (44.1 mg, 5.43 × 10 -2 1 mmol, 87% yield) was obtained as a white solid.

[0095] The results of nuclear magnetic resonance spectroscopy of the reactivity imparting compound of Example 2 obtained are shown below. 1 H NMR (500MHz, CDCl3): δ7.19(s,4H),7.11(s,4H),6.07-4.96(brm,4H),4.84-4.77(brm,4H),3.58-3.10(brm, 8H),1.40(s,18H). 13 C NMR (126MHz, CDCl3): δ166.4,165.9,156.2,140.2,127.9,126.6,122.1(q,J=275Hz),79.2,48.6,41.0,28.3. 19 F NMR (471 MHz, CDCl3): δ-66.4.

[0096] (Synthesis of reactivity imparting compound of Example 2A) In a 20 mL Schlenk tube, add the reactive additive compound from Example 2 (50 mg, 6.18 × 10 -2The mixture was charged with 1.0 mmol, 1.0 eq.) and dichloromethane (1.5 mL), and stirred at 0°C under an argon atmosphere. Trifluoroacetic acid (282 mg, 2.47 mmol, 40 eq.) was slowly added dropwise with stirring at 0°C, and then stirring was continued at room temperature for 2 hours. After stirring, the mixture was diluted with dichloromethane, and excess 1N NaOH was added and stirred for 15 minutes. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and then the solvent was removed and dried under vacuum to obtain the reactivity imparting compound (N 2 ,N 4 -bis(2-aminoethyl)-6-(bis-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzylamine)-1,3,5-triazine-2,4-diamine) as a white solid.

[0097] The results of nuclear magnetic resonance spectroscopy of the resulting reactivity imparting compound of Example 2A are shown below. 1 H NMR(500MHz,CDCl3):δ7.23(s,4H),7.10(d,4H,J=7.5Hz,4H),7.02(brs,1H), 5.50-5.02(brm,1H),4.72(s,4H),3.52-3.24(brm,4H),2.94-2.66(brm,4H). 13 C NMR (126MHz, CDCl3): δ166.3,166.0,140.6,128.0,127.8,126.5,122.1(q,J=275Hz),48.4,43.4,41.5,28.3(q,J=40.9Hz). 19 F NMR (471 MHz, CDCl3): δ-66.4.

[0098] (Synthesis of reactivity-imparting compound of Comparative Example 1) N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazin-2-amine was prepared as the reactivity imparting compound of Comparative Example 1. The reactivity imparting compound of Comparative Example 1 was obtained using the method described in Patent Document 2.

[0099] (Preparation of laminates using reactivity-imparting compounds and evaluation of peel strength) Next, laminates were produced using the reactivity-imparting compounds of Example 1, Example 2, and Comparative Example 1, and the peel strength (adhesion) thereof was evaluated. The evaluation samples were prepared according to the following procedure.

[0100] "Pre-dip solution" A pre-dip solution was prepared by adding 4.25 g of Cataprep 404A (manufactured by Rohm and Haas Electronic Materials) and 13.2 g of NaCl to 50 mL of distilled water while ultrasonically stirring for 10 minutes.

[0101] "Catalyst solution" 12.5 g of Cataprep 404 (manufactured by Rohm and Haas Electronic Materials) was added to 50 mL of distilled water while ultrasonically stirring for 10 minutes. After the Cataprep 404 was completely dissolved, 1.5 mL of Cataposit 44 (manufactured by Rohm and Haas Electronic Materials) was added to prepare a catalyst solution.

[0102] "Accelerator solution" An accelerator solution was prepared by adding 2.5 g of Accelerator 19E (manufactured by Rohm and Haas Electronic Materials) to 47.5 mL of distilled water while ultrasonically stirring for 10 minutes.

[0103] "Electroless plating solution" To 42.6 mL of distilled water, 2.5 mL of Okuno Pharmaceutical Co., Ltd. Adcopper IW-A, 0.75 mL of Okuno Pharmaceutical Co., Ltd. Adcopper C, 4 mL of Okuno Pharmaceutical Co., Ltd. Adcopper, and 0.15 mL of Okuno Pharmaceutical Co., Ltd. Electroless Copper RN were added while ultrasonically stirring for 10 minutes to prepare an electroless plating solution.

[0104] The substrate used was a cycloolefin polymer substrate (ZF16-100, COP substrate) or a polypropylene substrate (PP substrate). The COP substrate used was a COP substrate (30 mm × 60 mm × 100 μm thick) manufactured by Zeon Corporation. The PP substrate used was a PP substrate (30 mm × 60 mm × 1 mm thick) manufactured by Japan Polypropylene Corporation. The PP substrate or COP substrate was immersed in ethanol, and then ultrasonically irradiated twice for 5 minutes to clean the substrate, followed by drying. Thereafter, the PP substrate or COP substrate was immersed in Example 1, Example 2A, or Comparative Example 1 for 1 minute without corona discharge or plasma treatment, and then dried to form a reactivity-imparting compound layer.

[0105] (light irradiation) After forming the reactivity-imparting compound layer, the PP substrate was irradiated with light from a high-pressure mercury lamp. The dominant wavelength of the light from the high-pressure mercury lamp (UV curing device HLR 100T-2, AS ONE Corporation) was 365 nm, the irradiation distance was 10 cm, and the illuminance was 170 mW / cm. 2 The irradiation time was 1 minute.

[0106] (heat treatment) The COP substrate on which the reactivity-imparting compound layer was formed was subjected to a heat treatment in an oven at 130° C. for 10 minutes.

[0107] (plating process) The PP substrate after light irradiation or the COP substrate after heat treatment was immersed in a pre-dip solution for 1 minute, and then, without rinsing, immersed in a catalyst solution at 50°C for 1 minute and then rinsed with distilled water. The PP or COP substrate was then immersed in an accelerator solution for 3 minutes without drying and then rinsed with distilled water. After rinsing, the PP or COP substrate, while still wet, was immersed in an electroless copper plating solution at 34°C for 15 minutes, rinsed with distilled water and ethanol, and then dried. After drying, the PP or COP substrate (laminate) on which the copper layer was formed was annealed at 120°C for 10 minutes. After annealing, it was cooled to room temperature. After cooling, the annealed laminate was immersed in a copper sulfate-based electrolytic copper plating solution at a voltage of 15 V and a current density of 0.02 A / cm. 2 The substrate was then washed with distilled water, dried, and annealed at 120° C. for 10 minutes to obtain copper-plated laminates using the reactivity-imparting compounds of the respective Examples and Comparative Examples.

[0108] (Substrate adhesion) A copper plate (Yamamoto Plating, 2 cm x 3 cm x 0.3 mm thick) and a COP substrate (ZF14-100, 30 mm x 60 mm x 100 μm thick) manufactured by Zeon Corporation were washed and dried, and then immersed in an ethanol solution (concentration 2.07 mmol / L) of Example 1, Example 2A, or Comparative Example 1 for 1 minute and dried to form a reactivity imparting compound layer. Next, the copper plate and COP substrate on which the reactivity imparting compound layer had been formed were irradiated with light from a high-pressure mercury lamp (UV curing device HLR 100T-2, AS ONE Corporation). The dominant wavelength of the light from the high-pressure mercury lamp was 365 nm, and the illuminance was 170 mW / cm. 2 The irradiation time was 1 minute. The same reactivity imparting compound was used for the reactivity imparting compound layers of the COP substrate and the copper plate. After light irradiation, the copper plate and COP substrate were subjected to a force of 0.1 kN / cm 2 A copper plate laminate was obtained by bonding under conditions of a pressure of 1000 kJ / cm2 and 140°C for 30 minutes. As a control experiment, bonding was also attempted under the same conditions with a substrate not having a reactivity imparting compound layer, but bonding was not possible with the substrate not having a reactivity imparting compound layer.

[0109] "Peel strength measurement of copper plate laminate" The peel strength between the copper plate and the COP substrate was measured using the laminates prepared using the reactivity-imparting compounds of Example 1, Example 2A, and Comparative Example 1 at a pulling speed of 50 mm / min and a pulling angle of 90° using an adhesion tester (IMADA FORCE MEASUREMENT model mX2 manufactured by IMADA). The results are shown in Table 1. The reference example shows the results of substrate bonding without forming a reactivity-imparting compound layer. In Table 1, "-" indicates that no bonding was achieved.

[0110] "Peel strength measurement of copper-plated laminates" A 1 cm wide cut was made in the copper layer (copper foil) of each of the copper-plated laminates prepared using the reactivity-imparting compounds of Example 1, Example 2A, and Comparative Example 1, and the peel strength between the copper layer and the PP substrate or COP substrate was measured using an adhesion tester (IMADA FORCE MEASUREMENT model mX2, manufactured by IMADA) at a pulling speed of 50 mm / min and a pulling angle of 90°. The results for the copper layer and the PP substrate are shown in Table 2. The results for the copper layer and the COP substrate are shown in Table 3. The reference examples in Tables 2 and 3 are results of copper plating performed without forming a reactivity-imparting compound layer. In Table 2, a "-" indicates that a copper layer could not be formed. In Table 3, a "-" indicates that the peel strength could not be measured due to peeling.

[0111] [Table 1]

[0112] [Table 2]

[0113] [Table 3]

[0114] As shown in Tables 1 to 3, Example 1 and Example 2A showed higher adhesion than Comparative Example 1. In particular, when the copper plates were bonded by heat treatment, the peel strength of Example 1 and Example 2A increased by more than two times compared to Comparative Example 1. Furthermore, Example 1 and Example 2A showed high adhesion even without pretreatment such as corona treatment. [Industrial Applicability]

[0115] The reactivity imparting compound and the method for producing the reactivity imparting compound of the present invention are highly industrially applicable because they can suppress photodegradation of the substrate and provide high adhesion. [Explanation of symbols]

[0116] 10 substrate, 20 reactivity imparting compound layer, 30 coating layer, 100 laminate

Claims

1. A reactive functional group and a diazirine group; and the number of reactive functional groups is 2 or more, the number of diazirine groups is 2 or more, The reactivity-imparting compound, wherein the reactive functional group is at least one selected from the group consisting of an SH group, an SNa group, an amino group, a trimethoxysilyl group, and a triethoxysilyl group.

2. The reactivity-imparting compound according to claim 1, which is a compound represented by the following formula (1): 【Chemical 1】 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 [Z in the above formula (1)] １ , Z ２ represents a triazine ring, a benzene ring, or a nitrogen atom; A represents an acetylene group or the first structure represented by the above formula (2); n is 0 or 1; when n is 0, Z １ and Z ２ is directly bonded, and Q １ , Q ２ , Q ３ , and Q ４ At least two of Q are the reactive functional group or the second structure represented by formula (3), １ , Q ２ , Q ３ , and Q ４ At least two of the above are the third structure represented by the formula (4), and * in the formula (2) represents an adjacent carbon atom or nitrogen atom, and X １ and X ２ represents O, NH, or S; m1 represents an integer of 1 to 10; * in the above formula (3) represents an adjacent carbon atom or nitrogen atom; X ３ represents O, NH, or S; m2 represents an integer of 1 to 10; Y １ represents an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group, * in the above formula (4) represents an adjacent carbon atom or nitrogen atom, and X ４ is O, NH, S, or CH ２ m3 is an integer of 0 to 10, and Y ２ is a fourth structure represented by the above formula (5) or a fifth structure represented by the above formula (6), in which * represents an adjacent carbon atom, and R １ is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group, * in the above formula (6) represents an adjacent carbon atom, Ar is an arylene group, a divalent heterocyclic group, or a methylene group, R ２ is a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group.

3. Said Z １ is a triazine ring, and the Z ２ The reactivity imparting compound of claim 2, wherein is a nitrogen atom.

4. The reactivity imparting compound according to claim 3, which is a compound represented by the following formula (7): 【Chemistry 7】

5. The reactivity imparting compound according to claim 3, which is a compound represented by the following formula (8): 【Chemistry 8】

6. The reactivity-imparting compound according to claim 3, which is a compound represented by the following formula (9): 【Chemistry 9】

7. Said Z １ is a triazine ring, and the Z ２ The reactivity imparting compound of claim 2, wherein is a triazine ring.

8. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (10): 【Chemistry 10】

9. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (11): 【Chemistry 11】

10. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (12): 【Chemistry 12】

11. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (13): 【Chemistry 13】

12. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (14): 【Chemistry 14】

13. The reactivity imparting compound according to claim 7, which is a compound represented by the following formula (15): 【Chemistry 15】

14. The reactivity imparting compound according to claim 1 , which is a compound represented by the following formula (16): 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 [X in the above formula (16)] ５ and X ６ represents O, NH, or S; m4 represents an integer of 1 to 10; R ３ is the reactive functional group or the sixth structure represented by the formula (17), and R ４ is the seventh structure represented by the above formula (18), and * in the above formula (17) represents an adjacent carbon atom, and X ７ represents O, NH, or S; m5 represents an integer of 1 to 10; Y ３ is an SH group, an SNa group, an amino group, a triethoxysilyl group, or a trimethoxysilyl group.

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