Method for producing reactivity-imparting compound

Abstract

To provide a reactivity-imparting compound that inhibits photodegradation of a base material and provides high adhesion, a method for producing a reactivity-imparting compound, and a layered body.SOLUTION: This reactivity-imparting compound includes, in one molecule, silane coupling moieties represented by formula (1) below, and diazirine groups, where the number of the silane coupling moieties is two, or the number of the diazirine groups is two. In formula (1), * represents an adjacent carbon atom, R1, R2 and R3 each represent a hydrogen atom or an alkyl group, where R1, R2 and R3 may be the same or different.SELECTED DRAWING: Figure 2

Description

[Technical Field]

[0001] The present invention relates to a reactivity imparting compound, a method for producing the reactivity imparting compound, and a laminate. This application claims priority based on Japanese Patent Application No. 2020-185196 filed on November 5, 2020, and Japanese Patent Application No. 2021-145578 filed on September 7, 2021, the contents of which are incorporated herein by reference. [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 by 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, the compound having an OH group or an OH-yielding group, an azide group, and a triazine ring in one molecule, and the substrate being constructed using a polymer. UV light is irradiated onto a molecule containing an azide group to generate a nitrene from the azide group, and the generated nitrene reacts with the substrate surface, resulting in high adhesion. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent No. 4936344 Summary of the Invention [Problem to be solved by the invention]

[0009] However, there is currently a demand for a method that can provide higher adhesion than the technology of Patent Document 1. Furthermore, the technology of Patent Document 1 involves irradiating molecules having an azide group with short-wavelength ultraviolet light, which causes degradation of the substrate and reduces adhesion, which is a problem.

[0010] 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, a method for producing the reactivity imparting compound, and a laminate. [Means for solving the problem]

[0011] In order to solve the above problems, the present invention proposes the following means. <1> The present invention one In accordance with an embodiment As shown in the following formula (4): The method for producing the reactivity imparting compound 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 represented by the following formula (18) to which one or more diazirine groups have been imparted: The compound of the following formula (4) may be obtained by including a silane coupling moiety imparting step of reacting the diazirine group imparting compound represented by the following formula (18) with 3-aminopropyltriethoxysilane. [ka] [ka] <2> According to one embodiment of the present invention, The method for producing the reactivity imparting compound includes the steps of: 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-imparted compound represented by the following formula (20) having one or more diazirine groups added thereto; The diazirine group-imparting compound represented by the following formula (20) is reacted with 3-aminopropyltriethoxysilane: and a silane coupling moiety imparting step. Thus, a compound of the following formula (13) may be obtained. [ka] [ka] <3> According to one embodiment of the present invention As shown in the following formula (12): The method for producing the reactivity-imparting compound may include 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 represented by the following formula (15) to which one or more diazirine groups have been added, and a silane coupling moiety-imparting step of reacting the diazirine group-imparting compound represented by the following formula (15) with an amino group and 3-aminopropyltriethoxysilane represented by the following formula (6), thereby obtaining a compound of the following formula (12). [ka] [ka] <4> According to one embodiment of the present invention, The method for producing the reactivity imparting compound includes the steps of: 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-imparted compound represented by the following formula (17) having one or more diazirine groups added thereto; The diazirine group-imparting compound represented by the following formula (17) is reacted with 3-aminopropyltriethoxysilane: and a silane coupling moiety imparting step. Thus, a compound of the following formula (14) may be obtained. [ka] [ka] [Effects of the Invention]

[0012] According to the above-described aspects of the present invention, it is possible to provide a reactivity imparting compound that can suppress photodegradation of a substrate and achieve high adhesion, a method for producing the reactivity imparting compound, and a laminate. [Brief explanation of the drawings]

[0013] [Figure 1] 1 is a cross-sectional view of a laminate using a reactivity imparting compound according to an example of the present invention. [Figure 2] 1 is an estimated optical absorption spectrum of a reactivity imparting compound according to an example of the present invention. [Figure 3] 1 is a light absorption spectrum of a reactivity imparting compound according to a comparative example of the present invention. [Figure 4] 1 is a light absorption spectrum of a reactivity imparting compound according to Example 1 of the present invention. [Figure 5] 1 is a light absorption spectrum of a reactivity imparting compound according to Example 2 of the present invention. [Figure 6] FIG. 1 is a diagram showing changes in light absorption spectrum when the reactivity imparting compound according to Reference Example 1 is irradiated with light. [Figure 7] FIG. 1 is a diagram showing changes in light absorption spectrum when the reactivity imparting compound according to Reference Example 2 is irradiated with light. DETAILED DESCRIPTION OF THE INVENTION

[0014] 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.

[0015] (Reactivity-imparting compound) The reactivity-imparting compound according to this embodiment has, in one molecule, a silane coupling moiety represented by the following formula (1) and a diazirine group: In the following formula (1), * represents an adjacent carbon atom.

[0016] [ka]

[0017] The reactivity imparting compound according to this embodiment has one or more silane coupling moieties. The silane coupling moieties are moieties that generate silanol groups upon hydrolysis. The generated silanol groups react with the metal of the metal layer in the laminate, improving adhesion. That is, the reactivity imparting compound according to this embodiment is adsorbed onto the substrate surface to generate silanol groups, thereby improving adhesion to the metal layer. The adhesion to the metal layer improves as the number of silane coupling moieties in the reactivity imparting compound increases. When adhesion to the metal layer is low, it is preferable to increase the number of silane coupling moieties.

[0018] R of the silane coupling moiety in the above formula (1) 1 , R 2 and R 3 represents a hydrogen atom or an alkyl group. 1 , R 2 and R 3 may be the same or different. 1 , R 2 and R 3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. 1 , R 2 and R 3 The alkyl group is preferably a methyl group or an ethyl group.

[0019] The reactivity imparting compound according to this embodiment contains one or more diazirine groups. The diazirine group is chemically stable and generates carbene upon irradiation with long-wavelength ultraviolet light. Carbenes are highly reactive and can form covalent bonds with molecules in the vicinity of the carbene. Therefore, after applying the reactivity imparting compound according to this embodiment to a substrate surface or immersing the substrate in a solution of the reactivity imparting compound to allow the reactivity imparting compound to adsorb onto the substrate surface, light irradiation can form a covalent bond between the substrate and the reactivity imparting compound. This results in high adhesion between the substrate and the reactivity imparting compound according to this embodiment. Furthermore, since carbenes can achieve higher adhesion than nitrenes generated from azide groups, they can achieve 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, thereby suppressing photodegradation of resins. Adhesion to the substrate 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.

[0020] The reactivity-imparting compound is preferably a compound represented by the following formula (2).

[0021] [ka]

[0022] X in the above formula (2) represents a triazine ring or a benzene ring. X functions as a spacer between the silane coupling moiety and the diazirine group. X in the above formula (2) represents Z 1 , Z 2 , Z 3 By adjusting the bonding position with X, it is possible to adjust the positional relationship between the silane coupling moiety involved in adsorption to the metal layer of the laminate and the diazirine group involved in adsorption to the substrate of the laminate. This allows the adhesion between the substrate and the metal layer to be adjusted. X is preferably a triazine ring in order to facilitate production and adjust the positional relationship between the diazirine group and the silane coupling moiety. 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. When X in the above formula (2) is a benzene ring, Z 1 , Z 2 , Z 3 The bonding positions of X and Z are not particularly limited, but are preferably 1-, 3-, and 5-positions. 1 , Z 2 , Z 3 The other portion is not particularly limited and may be a hydrogen atom or any functional group such as a hydroxyl group or a methyl group.

[0023] Z in the above formula (2) 1 , Z 2 and Z 3 is preferably any one of O, NH, S, and CH2. 1 , Z 2 and Z 3 is preferably O or NH from the viewpoint of ease of production and chemical stability. 1 , Z 2 and Z 3 may be the same or different.

[0024] The integers m1, m2, and m3 represent the length of the spacer between the silane coupling moiety and the diazirine group. By adjusting the numbers of m1, m2, and m3, it is possible to adjust the contact frequency between the substrate and the diazirine group and the contact frequency between the metal layer and the silane coupling moiety. In the above formula (2), m1, m2, and m3 are preferably integers of 1 to 10. m1, m2, and m3 are preferably integers of 1 to 6. The integers m1, m2, and m3 may be the same or different.

[0025] Y 1 , Y 2 and Y 3 Y is a silane coupling moiety represented by the above formula (1) or a diazirine group represented by the following formula (3) or (11). 1 , Y 2 and Y 3 At least one of the silane coupling moieties is a silane coupling moiety represented by the above formula (1). In the above formula (2), the number of silane coupling moieties is 1 or 2. The reactivity imparting compound represented by the above formula (2) has at least one silane coupling moiety, and therefore can improve the adhesion between the reactivity imparting compound and the metal layer. When it is desired to further improve the adhesion to the metal layer, the number of silane coupling moieties is set to 2.

[0026] Y 1 , Y 2 and Y 3 At least one of the groups is a diazirine group (diazirine-containing group) represented by the following formula (3) or formula (11). In the above formula (2), the number of diazirine groups is 1 or 2. The reactivity imparting compound represented by the above formula (2) has at least one diazirine group, and therefore can form one or more strong covalent bonds between the reactivity imparting compound and the substrate. Therefore, the reactivity imparting compound according to this embodiment has excellent adhesion to the substrate. When it is desired to further improve the adhesion to the metal layer, the number of diazirine groups is set to 2. Note that * in the following formula (3) represents an adjacent carbon atom. R in the following formula (3) 4is not particularly limited and may be any functional group. The presence of a diazirine group near the terminal improves the frequency of contact with the substrate. 4 is preferably a hydrogen atom, a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group. 4 is preferably a trifluoromethyl group or a pentafluoroethyl group, since the photoreaction efficiency is improved.

[0027] In the following formula (11), * represents an adjacent carbon atom. 5 is not particularly limited and may be any functional group. The presence of a diazirine group near the terminal improves the frequency of contact with the substrate. 5 is preferably a hydrogen atom, a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group. 5 is preferably a trifluoromethyl group or a pentafluoroethyl group, since this improves the photoreaction efficiency. In the following formula (11), A is an arylene group or a divalent heterocyclic group. In the arylene group or the divalent heterocyclic group, some or all of the hydrogen atoms may be substituted with halogen atoms, alkyl groups, etc.

[0028] Examples of the arylene group for A in the following formula (11) 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.

[0029] Examples of the divalent heterocyclic group A in the following formula (11) include divalent groups in which two hydrogen atoms have been removed from the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting a heterocycle such as furan, thiophene, or pyridine.

[0030] [ka]

[0031] [ka]

[0032] Specific examples of the above formula (2) include N represented by the following formula (5): 2 ,N 4 -bis(2-(3-methyl-3H-diazirin-3-yl)ethyl)-N 6 -((3-triethoxysilyl)propyl)-1,3,5-triazine-2,4,6-triamine, 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazine-2-amine represented by the following formula (4), 6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazine-2-amine represented by the following formula (12), 2 ,N 4 -bis(3-(triethoxysilyl)propyl)-1,3,5-triazine-2,4-diamine, N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2-amine represented by the following formula (13), N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2-amine represented by the following formula (14), 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2,4-diamine.

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] (Action of reactivity-imparting compound) The reactivity-imparting compound according to this embodiment has a diazirine group, which is a photoreactive nitrogen functional group, and a silane coupling moiety. The diazirine group is photodecomposed by light (at a wavelength of approximately 360 nm) to generate a highly reactive chemical species, carbene (a bicoordinated carbon atom with six valence electrons and no charge). This carbene moiety forms a covalent bond with the substrate surface of the laminate. After forming the covalent bond, the silane coupling moiety of this reactivity-imparting compound is fixed to the substrate surface. The silane coupling moiety forms a silanol group upon hydrolysis with water contained in a solvent or the like. Therefore, the substrate can be imparted with reactivity that allows it to bond with other materials (e.g., a metal layer) via the silanol group.

[0039] Conventionally known compounds having an azide group and a triazine ring are decomposed by light, and the azide group generates a highly reactive chemical species (nitrene). Compared to compounds that generate nitrenes derived from the azide group, the reactivity imparting compound that generates carbene of the present embodiment can be activated by light with a longer wavelength. Furthermore, the reactivity imparting compound having a diazirine group of this embodiment has higher bonding strength than conventional compounds having an azide group. For example, when a resin to which the reactivity imparting compound has been imparted is metal-plated, the reactivity imparting compound of this embodiment is less likely to cause the metal to peel off than conventional compounds having an azide group. The reactivity imparting compound of the present disclosure can be applied not only to bonding between resin and metal, but also to bonding between resins, such as bonding between silicon resins. The reactivity imparting compound of the present disclosure can also be applied to bonding between resin and inorganic materials such as ceramics and quartz.

[0040] (Method of producing reactivity-imparting compound) The reactivity imparting compound of this embodiment can be appropriately produced, for example, by introducing a silane coupling moiety and a diazirine group 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.

[0041] The method for producing a 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 silane coupling moiety imparting step of reacting the diazirine group imparting compound with a compound having an amino group and a silane coupling moiety represented by the following formula (6): In the following formula (6), * represents an adjacent carbon atom. 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; however, 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.

[0042] [ka]

[0043] <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. Examples of the compound having a hydroxyl group and a diazirine group include 2-(3-methyl-3H-diazirin-3-yl)ethanol, 2-(3-butyl-3H-diazirin-3-yl)ethanol, 2-(3-pentyl-3H-diazirin-3-yl)ethanol, and (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol.

[0044] The synthesis using 2-(3-methyl-3H-diazirin-3-yl)ethanol is explained below. When one diazirine group is to be added, for example, the reaction of the following formula (7) can be mentioned. In the following formula (7), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. The reaction of the following formula (7) can yield 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine of the following formula (15).

[0045] [ka]

[0046] [ka]

[0047] Synthesis using (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol is described below. When one diazirine group is to be added, for example, the reaction of the following formula (16) can be mentioned. In the following formula (16), base represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. By the reaction of the following formula (16), 2,4-dichloro-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine of the following formula (17) can be obtained. The reaction temperature is, for example, room temperature (20°C to 30°C).

[0048] [ka]

[0049] [ka]

[0050] When two diazirine groups are added, the reaction can be, for example, as shown in the following formula (8). In the following formula (8), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. 2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine of the following formula (18) can be obtained by the reaction of the following formula (8). The number of diazirine groups added to the triazine ring can be controlled by the reaction temperature when adding the diazirine groups. When only one diazirine group is added, for example, the reaction temperature is room temperature, and when two diazirine groups are added, the reaction temperature is, for example, 40 to 50°C. The reaction temperature can be set appropriately.

[0051] [ka]

[0052] [ka]

[0053] When two diazirine groups are added using (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol, the reaction is as shown in formula (19) below. In formula (19) below, base represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. The reaction of formula (19) below can produce 2-chloro-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine of formula (20) below. The number of diazirine groups added to the triazine ring can be controlled by the reaction temperature and compounding ratio when adding the diazirine groups.

[0054] [ka]

[0055] [ka]

[0056] <Silane coupling moiety imparting step> In the silane coupling moiety 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 silane coupling moiety represented by the above formula (6). Through this silane coupling moiety imparting step, the reactivity imparting compound according to this embodiment can be obtained.

[0057] R of the silane coupling moiety in the above formula (6) 1 , R 2 and R 3 represents a hydrogen atom or an alkyl group. 1 , R 2 and R 3 may be the same or different. 1 , R 2 and R 3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. 1 , R2 and R 3 The alkyl group is preferably a methyl group or an ethyl group.

[0058] Examples of compounds having an amino group and a silane coupling moiety represented by the above formula (6) include 3-aminopropyltriethoxysilane and 3-aminopropyltrimethoxysilane.

[0059] 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 (7) and 3-aminopropyltriethoxysilane is shown in the following formula (9). In the following formula (9), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. Through the reaction of the following formula (9), 6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N of the above formula (12) is obtained. 2 ,N 4 -bis(3-(triethoxysilyl)propyl)-1,3,5-triazine-2,4-diamine can be obtained.

[0060] [ka]

[0061] An example of the reaction between 2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine synthesized by the above formula (8) and 3-aminopropyltriethoxysilane is shown in the following formula (10). In the following formula (10), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. Through the reaction of the following formula (10), 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazin-2-amine of the above formula (4) can be obtained.

[0062] [ka]

[0063] An example of the reaction between 2,4-dichloro-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine synthesized by the above formula (16) and 3-aminopropyltriethoxysilane is shown in the following formula (21). In the following formula (21), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. Through the reaction of the following formula (21), N in the above formula (14) can be obtained. 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2,4-diamine can be obtained.

[0064] [ka]

[0065] An example of the reaction between 2-chloro-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine synthesized by the above formula (19) and 3-aminopropyltriethoxysilane is shown in the following formula (22). In the following formula (22), "base" represents a base, and diisopropylethylamine, pyridine, triethylamine, etc. can be used. Through the reaction of the following formula (22), N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazin-2-amine of the above formula (13) can be obtained.

[0066] [ka]

[0067] (Laminate) An example of 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 comprises a substrate (first substrate) 1, a reactivity imparting compound layer 2, and a metal layer (second substrate) 3. Each component will be described below.

[0068] (base material) The substrate 1 may be made of an inorganic material such as ceramics, or a resin. The form of the substrate 1 is not particularly limited, and may be a plate or granule. The substrate 1 is an example of a first substrate.

[0069] The resin 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 another 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 in vehicle parts and the like, and is used in laminates having ABS and metal bonded portions by applying metal plating to the surface. Resins for circuits include epoxy resin, polyimide resin, liquid crystal polymer, cycloolefin polymer (COP), fluorine-based resin, polyphenylene sulfide (PPS), and the like.

[0070] When the laminate 100 is used as a printed wiring board, a thermal load is applied to the laminate 100 during soldering of wiring, etc. Furthermore, when the laminate 100 is used in a moving part of an electronic product, sufficient mechanical strength is required. Therefore, a polyimide resin is preferred, as it has excellent properties in terms of heat resistance, mechanical strength, and dimensional stability.

[0071] An example of the inorganic material of the substrate 1 is a material containing silicon oxide. 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 surface by metal plating or the like.

[0072] The resin of the substrate 1 may contain inorganic particles such as talc, a lubricant, an antistatic agent, etc., depending on the purpose of improving the mechanical strength, etc.

[0073] When the laminate 100 is used as a printed wiring board, its thickness is not particularly limited. For example, when the substrate 1 is used as a flexible wiring board, the thickness of the substrate 1 is preferably 1 μm or more and 200 μm or less. If the thickness of the substrate 1 is less than 1 μm, the mechanical strength of the substrate 1 may be insufficient, which is not preferred. The thickness of the substrate 1 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 1 is more preferably 150 μm or less.

[0074] When the laminate 100 is used as a printed wiring board, the arithmetic mean roughness Ra of the substrate 1 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.

[0075] (Reactivity-imparting compound layer 2) The reactivity imparting compound layer 2 is provided on the substrate 1 and is composed of the reactivity imparting compound according to this embodiment. Here, "provided on the substrate 1" not only means providing the reactivity imparting compound layer 2 so as to be in contact with the surface of the substrate 1, but also includes providing an intermediate layer between the substrate 1 and the reactivity imparting compound layer 2. It also includes providing the reactivity imparting compound layer partially on the surface of the substrate 1.

[0076] The thickness of the reactivity imparting compound layer 2 is not particularly limited as long as it covers the entire surface of the substrate 1. The thickness of the reactivity imparting compound layer 2 may be, for example, equal to or greater than the thickness of a monomolecule of the reactivity imparting compound (equal to or greater than a monomolecular layer) that constitutes the reactivity imparting compound layer 2. The upper limit of the thickness of the reactivity imparting compound layer 2 is not particularly limited, but is, for example, 400 nm or less.

[0077] (metal layer) The metal layer 3 is provided on the reactivity imparting compound layer 2. The metal layer 3 is made of silver, tin, copper, a copper alloy, or the like. When the laminate 100 is a printed circuit board, copper and copper alloys, which have high conductivity, are preferred as metals for the metal layer 3 from the viewpoint of power loss and transmission loss. The metal layer is an example of a second substrate.

[0078] The thickness of the metal layer is not particularly limited, but is, for example, 0.1 μm to 50 μm. More preferably, the thickness of the metal layer is 2 μm to 10 μm. If the thickness of the metal layer is 0.1 μm to 50 μm, sufficient mechanical strength can be obtained.

[0079] The laminate 100 according to the present embodiment has been described above. In the present embodiment, the metal layer 3 has been described as an example of the second substrate; however, the second substrate of the present invention is not limited to the metal layer 3. For example, instead of a metal layer, a resin substrate made of a liquid crystal polymer, epoxy resin, silicone resin, or the like may be used as the second substrate. Furthermore, instead of a metal layer, an inorganic substrate made of ceramics, quartz, or the like may be used as the second substrate. Furthermore, although the present embodiment exemplifies the use of a metal layer as the second substrate, the shape of the second substrate is not limited to a layered structure as long as the first substrate and the second substrate can be bonded via the reactivity-imparting compound. The combination of the first substrate and the second substrate of the laminate of the present disclosure can be, for example, a combination of an inorganic material such as a resin and a ceramic, a combination of a resin and a metal, a combination of an inorganic material such as a ceramic and a metal, or a combination of the same or different resins.

[0080] (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.

[0081] When producing the laminate according to this embodiment, first, a reactivity imparting compound layer 2 made of the reactivity imparting compound according to this embodiment is formed on a substrate (first substrate) 1. The method for forming the reactivity imparting compound layer 2 is not particularly limited. For example, the reactivity imparting compound layer 2 may be formed by applying a solution containing the reactivity imparting compound to the surface of the substrate 1. Alternatively, the reactivity imparting compound layer 2 may be formed by immersing the substrate 1 in a solution containing the reactivity imparting compound.

[0082] 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 evaporated by air drying, heating, etc.

[0083] An amplifier may be added to the solution containing the reactivity-imparting compound. Examples of the amplifier include compounds that contribute to other bonds, such as silane coupling agents, and photosensitizers, such as benzophenone.

[0084] After forming the reactivity imparting compound layer 2 on the substrate 1, energy is applied to generate carbene from the diazirine group of the reactivity imparting compound. This carbene reacts with the substrate 1, resulting in high adhesion between the reactivity imparting compound layer 2 and the substrate 1.

[0085] The energy can be applied, for example, by irradiation with light. The diazirine group of the reactivity imparting compound of this embodiment is activated in response to a wide range of wavelengths, but to suppress deterioration due to light, it is preferable that the light be on the long wavelength side. Specifically, a wavelength of 300 nm or more is preferable, and a wavelength of 450 nm or less is preferable. For light irradiation, an existing light irradiation device can be appropriately used. In this case, the substrate 1 on which the reactivity imparting compound layer 2 has been formed may be heated before irradiation to enhance the activation effect.

[0086] After applying energy to the reactivity imparting compound layer 2 to improve the adhesion between the substrate 1 and the reactivity imparting compound layer 2, a metal layer (second substrate) 3 is provided. The metal layer 3 may be provided by plating or the like. As a 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 metal layer 3, it is preferable to use wet plating such as electroless plating or electroplating to form a thin metal film. Before forming the metal layer 3, a conventionally known pretreatment process for the plating process may also be applied as appropriate. Furthermore, when a resin substrate or an inorganic substrate is formed as the second substrate on the reactivity imparting compound layer 2, a known method can be used. [Example]

[0087] 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.

[0088] (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) Mass spectrometry: JEOL JMS-700 mass spectrometer ·reagent Various reagents: Commercially available products were used and purified by standard methods as necessary. 2-(3-methyl-3H-diazirin-3-yl)ethanol was purchased from Amadis Chemical. (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol was purchased from Tokyo Chemical Industry Co., Ltd. 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.)

[0089] The synthesis method of the sample will be explained below.

[0090] Example 1 A 10 mL side-arm flask was purged with argon and charged with anhydrous THF (1.1 mL), 2-(3-methyl-3H-diazirin-3-yl)ethanol (0.39 mL, 4.07 mmol, 2.50 eq.), and diisopropylethylamine (0.54 mL, 4.07 mmol, 2.50 eq.), followed by cooling to 0 °C. Cyanuric chloride (0.307 g, 1.63 mmol, 1.00 eq.) dissolved in anhydrous THF (0.72 mL) was added and stirred for 1 hour in the dark. The mixture was warmed to room temperature (20-30 °C) and stirred for 16 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (0.654 g). The crude product was separated and purified by silica gel column chromatography using hexane:chloroform = 1:1 as a developing solvent to obtain 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.292 g, 1.18 mmol, 72%) as a yellow liquid.

[0091] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine) are shown below. 1 H NMR(500MHz,CDCl3):δ 1.14(s,3H,CH3),1.88(t,J=6.6Hz,2H,CH2),4.43(t,J=6.6Hz,2H,CH2); 13 C NMR(126MHz,CDCl3):δ 20.1,23.7,33.6,65.4,170.8,172.7; FAB-MS: m / z 248 [(M+H) + ].

[0092] Next, 2,4-dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.500 g, 2.02 mmol, 1.00 eq.) was placed in a 50 mL side-arm flask and purged with argon. Anhydrous 1,4-dioxane (10.1 mL), 3-aminopropyltriethoxysilane (0.86 mL, 3.69 mmol, 1.83 eq.), and diisopropylethylamine (0.81 mL, 4.76 mmol, 2.36 eq.) were added, 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a colorless liquid (1.04 g). The crude product was separated and purified by silica gel column chromatography using chloroform:ethyl acetate=3:1 as a developing solvent to obtain 6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N 2 ,N 4 -bis(3-(triethoxysilyl)propyl)-1,3,5-triazine-2,4-diamine (0.476 g, 0.770 mmol, 38%) was obtained as a colorless liquid.

[0093] The resulting compound (6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N 2 ,N 4 The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of -bis(3-(triethoxysilyl)propyl)-1,3,5-triazine-2,4-diamine) are shown below. 1 H NMR(500MHz,CDCl3):δ 0.66(brt,4H,CH2),1.09(s,3H,CH3),1.23(t,J=6.9Hz,18H,CH3),1.67(brs,4H,CH2),1.77(brs,2H,CH2),3.33 and 3.40(each brs,total 4H,CH2),3.82(q,J=6.9Hz,12H,CH2),4.13 and 4.20(each brs,total 2H,CH2),5.14 and 5.24(brs,2H,NH); 13C NMR(126MHz,CDCl3):δ 7.75,18.4,20.1,23.0,24.1,34.1,43.3,58.5,61.4,16.3,170.0; HR-FAB-MS: m / z calculation for C 25 H 52 N7O7Si2[(M+H) + ]:618.3467;Found:618.3471.

[0094] Example 2 A 10 mL side-arm flask was purged with argon and charged with anhydrous THF (1.1 mL), 2-(3-methyl-3H-diazirin-3-yl)ethanol (0.39 mL, 4.07 mmol, 2.50 eq.), and diisopropylethylamine (0.54 mL, 4.07 mmol, 2.50 eq.), followed by cooling to 0 °C. Cyanuric chloride (0.308 g, 1.63 mmol, 1.00 eq.) dissolved in anhydrous THF (0.72 mL) was added and stirred for 1 hour in the dark. The mixture was heated to 40 °C and stirred for 17 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (0.582 g). The crude product was separated and purified by silica gel column chromatography using hexane:chloroform = 1:1 as a developing solvent to obtain 2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.227 g, 0.728 mmol, 45%) as a yellow liquid.

[0095] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine) are shown below. 1 H NMR(500MHz,CDCl3):δ 1.13(s,6H,CH3),1.85(t,J=6.4Hz,4H,CH2),4.37(t,J=6.4Hz,4H,CH2); 13C NMR(126MHz,CDCl3):δ20.2,23.8,33.8,64.4,171.9,172.9; FAB-MS: m / z 312 [(M+H) + ].

[0096] Next, 2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.396 g, 1.27 mmol, 1.00 eq.) was placed in a 50 mL side-arm flask and placed under an argon atmosphere. Anhydrous 1,4-dioxane (8.5 mL), 3-aminopropyltriethoxysilane (0.34 mL, 1.46 mmol, 1.15 eq.), and diisopropylethylamine (0.33 mL, 1.94 mmol, 1.53 eq.) were added, 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (0.645 g). The crude product was separated and purified by silica gel column chromatography using chloroform:ethyl acetate=4:1 as a developing solvent, to obtain 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazin-2-amine (0.501 g, 1.01 mmol, 80%) of Example 2 as a yellow liquid.

[0097] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazin-2-amine) are shown below. 11H NMR (500 MHz, CDCl3): δ 0.67 (t, J = 7.6 Hz, 2H, CH2), 1.10 (s, 3H, CH3), 1.11 (s, 3H, CH3), 1.23 (t, J = 6.9 Hz, 9H, CH3), 1.71 (quint, J = 7.6 Hz, 2H, CH2), 1.79 (t, J = 6.3 Hz, 2H, CH2), 1.81 (t, J = 6.3 Hz, 2H, CH2), 3.44 (q, J = 7.6 Hz, 2H, CH2), 3.83 (q, J = 6.9 Hz, 6H, CH2), 4.22 (t, J = 6.3 Hz, 2H, CH2), 4.28 (t, J = 6.3 Hz, 2H, CH2), 5.80 (brt, 1H, NH); 13 13C NMR (126 MHz, CDCl3): δ 7.73, 18.4, 20.12, 20.14, 22.9, 23.97, 24.01, 33.9, 43.5, 58.5, 62.3, 62.4, 168.1, 171.3, 171.9; HR-FAB-MS: m / z calcd for C 20 H 37 N8O5Si [(M + H) + : 497.2656; Found: 497.2652.

[0098] (Example 3) Cyanuric chloride (1.00 g, 5.42 mmol, 1.00 eq.) was placed in a 50 mL side-arm flask and purged with argon. It was dissolved in anhydrous methylene chloride (9.5 mL) and cooled to 0 °C. (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol (1.17 g, 5.41 mmol, 1.00 eq.) and diisopropylethylamine (1.01 mL, 5.94 mmol, 1.10 eq.) were dissolved in anhydrous methylene chloride (5.4 mL) and stirred for 1 hour in the dark. The mixture was warmed to room temperature (20-30 °C) and stirred for 1.5 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (1.88 g). The crude product was separated and purified by silica gel column chromatography using hexane:chloroform=1:4 as a developing solvent to obtain 2,4-dichloro-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine (1.45 g, 3.98 mmol, 73%) as a yellow liquid.

[0099] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (2,4-dichloro-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine) are shown below. 1 H NMR(500MHz,CDCl3):δ 5.53(s,2H,CH2),7.23(d,J=8.6Hz,2H,benzene-H),7.51(d,J=8.6Hz,2H,benzene-H); 13 C NMR (126MHz, CDCl3): δ 28.4(q,J=40.9Hz),70.7,122.1(q,J=275Hz),127.0,128.9,130.0,135.5,170.8,172.8; 19 F NMR (471 MHz, CDCl3): δ -65.0; HR-FAB-MS: m / z calculation for C 12H7Cl2F3N5O[(M+H) + ]:363.9980;Found:363.9972.

[0100] Next, 2,4-dichloro-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine (0.300 g, 0.824 mmol, 1.00 eq.) was placed in a 20 mL side-arm flask and purged with argon. Anhydrous 1,4-dioxane (6.04 mL), 3-aminopropyltriethoxysilane (0.44 mL, 1.89 mmol, 2.29 eq.), and diisopropylethylamine (0.42 mL, 2.47 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (0.360 g). The crude product was separated and purified by silica gel column chromatography using chloroform:ethyl acetate=4:1 as a developing solvent to obtain N 2 ,N 4 -bis((3-triethoxysilyl)propyl)-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2,4-diamine (0.160 g, 0.218 mmol, 26%) as a yellow liquid.

[0101] The resulting compound (N 2 ,N 4 The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of -bis((3-triethoxysilyl)propyl)-6-((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine-2,4-diamine) are shown below. 11H NMR (500 MHz, CDCl3): δ 0.65 and 0.66 (each brt, total 4H, CH2), 1.22 (t, J = 6.9 Hz, 18H, CH3), 1.68 (brs, 4H, CH2), 3.33 and 3.39 (each brs, total 4H, CH2), 3.82 (q, J = 6.9 Hz, 12H, CH2), 5.14, 5.23 and 5.29 (each brs, total 2H, NH), 5.33 (brs, 2H, CH2), 7.16 (d, J = 6.9 Hz, 2H, benzene-H), 7.43 - 7.48 (brm, 2H, benzene-H); 13 13C NMR (126 MHz, CDCl3): δ 7.75, 18.4, 23.0, 23.1, 28.4 (q, J = 40.9 Hz), 43.4, 58.5, 66.8, 67.0, 67.2, 122.2 (q, J = 275 Hz), 126.5, 127.9, 128.3, 128.4, 128.5, 138.9, 166.8, 167.3, 167.6, 170.0, 170.4; 19 19F NMR (471 MHz, CDCl3): δ -65.2.

[0102] (Example 4) Cyanuric chloride (1.00 g, 5.42 mmol, 1.00 eq.) was placed in a 50 mL side-arm flask and purged with argon. It was dissolved in anhydrous methylene chloride (9.5 mL) and cooled to 0 °C. (4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)methanol (2.42 g, 11.9 mmol, 2.20 eq.) and diisopropylethylamine (2.02 mL, 11.9 mmol, 2.20 eq.) were dissolved in anhydrous methylene chloride (5.4 mL) and stirred for 1 hour in the dark. The mixture was warmed to room temperature (20-30 °C) and stirred for 16 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow solid (3.32 g). The crude product was separated and purified by silica gel column chromatography using hexane:chloroform=1:4 as a developing solvent to obtain 2-chloro-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine (2.46 g, 4.52 mmol, 83%) as a white solid.

[0103] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (2-chloro-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine) are shown below. 1 H NMR(500MHz,CDCl3):δ 5.47(s,4H,CH2),7.21(d,J=8.4Hz,4H,benzene-H),7.47(d,J=8.4Hz,4H,benzene-H); 13 C NMR(126MHz,CDCl3):δ 28.4(q,J=40.9Hz),69.8,122.1(q,J=275Hz),126.9,128.7,129.7,136.3,172.0,173.0; 19 F NMR (471 MHz, CDCl3): δ -65.0. HR-FAB-MS: m / z calculation for C 21 H13 ClF6N7O2[(M+H) + ]:544.0723;Found:544.0722.

[0104] Next, 2-chloro-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazine (0.266 g, 0.489 mmol, 1.00 eq.) was placed in a 20 mL side-arm flask and purged with argon. Anhydrous 1,4-dioxane (5.35 mL), 3-aminopropyltriethoxysilane (0.12 mL, 0.515 mmol, 1.05 eq.), and diisopropylethylamine (0.12 mL, 0.706 mmol, 1.44 eq.) were added, 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a yellow liquid (0.339 g). The crude product was separated and purified by silica gel column chromatography using chloroform:ethyl acetate=4:1 as a developing solvent to obtain N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazin-2-amine (0.243 g, 0.333 mmol, 68%) as a yellow liquid.

[0105] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (N-((3-triethoxysilyl)propyl)-4,6-bis((4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)oxy)-1,3,5-triazin-2-amine) are shown below. 1H NMR(500MHz,CDCl3):δ 0.64(t,J=7.5Hz,2H,CH2),1.22(t,J=6.9Hz,9H,CH3),1.69(quint,J=7.5Hz ,2H,CH2),3.41(q,J=7.5Hz,2H,CH2),3.82(q,J=6.9Hz,6H,CH2),5.36(s,2H, CH2),5.39(s,2H,CH2),5.91(t,J=7.5Hz,1H,NH),7.18(d,J=7.9Hz,4H,benzene-H),7.43(d,J=7.9Hz,2H,benzene-H),7.46(d,J=7.9Hz,2H,benzene-H); 13 C NMR(126MHz,CDCl3):δ 7.73,18.4,22.8,28.4(q,J=40.9Hz),43.5,58.6,67.8,68.1,122.1(q,J =275Hz),126.6,128.2,128.5,128.9,129.0,138.0,168.1,171.3,171.9; 19 F NMR (471 MHz, CDCl3): δ -65.1.

[0106] (Reference example 1) 2,4-Dichloro-6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.110 g, 0.443 mmol, 1.00 eq.) was placed in a 10 mL side-arm flask and placed under an argon atmosphere. Anhydrous 1,4-dioxane (2.21 mL), propylamine (0.08 mL, 0.974 mmol, 2.20 eq.), and diisopropylethylamine (0.23 mL, 1.35 mmol, 3.05 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 the mixture was dried under vacuum to obtain a crude white solid (0.152 g). The crude product was separated and purified by silica gel column chromatography using chloroform as a developing solvent to obtain 6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N 2 ,N 4-dipropyl-1,3,5-triazine-2,4-diamine (0.130 g, 0.443 mmol, 100%) was obtained as a white solid.

[0107] The resulting compound (6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N 2 ,N 4 The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the compound (dipropyl-1,3,5-triazine-2,4-diamine) are shown below. 1 H NMR(500MHz,CDCl3):δ 0.95(t,J=7.2Hz,6H,CH3),1.09(s,3H,CH3),1.58(br sext,4H,CH2),1.74 and 1.78(br t and br s,total 2H,CH2),3.30 and 3.36(each br s,total 4H,CH2),4.13 and 5.07(each br s,total 2H,NH); 13 C NMR(126MHz,CDCl3):δ 11.5,20.2,23.0,24.1,34.1,42.7,61.3,61.4,166.9,167.3,170.3; HR-FAB-MS: m / z calculation for C 13 H 24 NO [(M+H) + ]:294.2042;Found:294.2044.

[0108] (Reference example 2) A 20 mL side-arm flask was charged with 2-chloro-4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-1,3,5-triazine (0.280 g, 0.898 mmol, 1.00 eq.) and placed under an argon atmosphere. Anhydrous 1,4-dioxane (5.58 mL), propylamine (0.09 mL, 1.10 mmol, 1.22 eq.), and diisopropylethylamine (0.23 mL, 1.35 mmol, 1.50 eq.) were added, the mixture was heated to 65 °C, and stirred for 3 h 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, filtered, and the solvent was removed. The crude product was then dried under vacuum to give a white solid (0.300 g). The crude product was separated and purified by silica gel column chromatography using chloroform as a developing solvent to obtain 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-propyl-1,3,5-triazin-2-amine (0.291 g, 0.870 mmol, 97%) as a white solid.

[0109] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-propyl-1,3,5-triazin-2-amine) are shown below. 1 H NMR(500MHz,CDCl3):δ 0.96(t,J=7.2Hz,3H,CH3),1.10(s,3H,CH3),1.11(s,3H,CH3),1.61(sext,J=7.2Hz,2H,CH2),1.79(t,J=6.6Hz,2H,CH2 ),1.82(t,J=6.9Hz,2H,CH2),3.40(q,J=7.2Hz,2H,CH2),4.23(t,J=6.6Hz,2H,CH2),4.29(t,J=6.9Hz,2H,CH2),5.65(br s,1H,NH); 13 C NMR(126MHz,CDCl3):δ 11.4,20.2,22.8,24.0,24.1,34.0,42.9,62.3,62.5,168.2,171.3,171.9; HR-FAB-MS: m / z calculation for C14 H 23 N8O2[(M+H) + ]:335.1944;Found:335.1948.

[0110] (Comparative Example 1) A 50 mL three-neck flask was charged with a stir bar and cyanuric chloride (1.00 g, 5.42 mmol), followed by the addition of THF (6 mL) and acetonitrile (6 mL) and the mixture was cooled to -10 °C. Trimethylsilyldiazomethane (2.0 M hexane solution, 3.0 mL, 6.0 mmol) was added, and the mixture was warmed to room temperature (20-30 °C) and stirred for 6 h. After stirring, water was added, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated on a rotary evaporator, and dried under reduced pressure to obtain a crude product as a brown solid. This crude product was separated and purified by silica gel chromatography using chloroform:hexane = 4:1 as a developing solvent to obtain 2,4-dichloro-6-(diazomethyl)-1,3,5-triazine (0.689 g, 3.63 mmol, 67%) as a yellow solid.

[0111] Next, a 50 mL three-neck flask was charged with a stir bar and 2,4-dichloro-6-(diazomethyl)-1,3,5-triazine (0.758 g, 3.99 mmol), and the flask was argon-exposed. Then, dry 1,4-dioxane (25 mL) was added. Triethylamine (1.66 mL, 12.0 mmol) was added, followed by 3-aminopropyltriethoxysilane (2.14 mL, 9.18 mmol), and the mixture was stirred at 65°C for 3 hours. After stirring, water was added, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated on a rotary evaporator, and dried under reduced pressure to obtain a crude product as a yellow viscous oil. This crude product was separated and purified by silica gel column chromatography using chloroform as a developing solvent to obtain the reactivity-imparting compound, 2,4-bis[(3-triethoxysilylpropyl)amino]-6-diazomethyl-1,3,5-triazine (1.661 g, 2.97 mmol, 74%), as a yellow viscous oil.

[0112] The results of nuclear magnetic resonance spectroscopy and mass spectroscopy of the resulting compound (2,4-bis[(3-triethoxysilylpropyl)amino]-6-diazomethyl-1,3,5-triazine) are shown below. 1 H NMR(400MHz,CDCl3)δ 0.66 (t,J=8.4Hz,4H,CH2),1.27(t,J=7.0Hz,18H,CH3),1.67(br s,4H,CH2),3.36(br s,4H,CH2),3.82(q,J=7.0Hz,12H,CH2),4.83-5.24(m,2H,NH),5.44(br s,1H, CH) 13 C NMR (101 MHz, CDCl3)δ 7.7,18.3,23.0, 43.1, 51.5, 58.4, 146.8,165.1; FAB-MS m / z [(M+H) + ]: 560.3048

[0113] (UV-vis absorption spectrum simulation) The following theoretical calculation program was used to simulate the UV-vis absorption spectrum of the reactivity-imparting compound. Theoretical calculation program Gaussian 16, Revision C.01 Simulation method for UV-vis absorption spectrum: A model compound in which the triethoxysilylpropylamino group of the reactivity imparting compound of formula (4) above was simplified to a methylamino group (the model compound in Example 2 in which the triethoxysilylpropylamino group was replaced with a methylamino group) was molecular modeled, and the molecular structure was optimized by density functional (DFT) calculations. The functional used in the DFT calculations was B3LYP, and the basis set was 6-31G(d). Using the optimized structure of the model compound obtained, time-dependent density functional (TD-DFT) calculations were performed to obtain simulation results for the UV-vis absorption spectrum. The functional used in the TD-DFT calculations was B3LYP, and the basis set was 6-31+G(d,p).

[0114] (UV-vis absorption spectrum) The following instruments and reagents were used to analyze the obtained results of Examples 1 to 4 and Comparative Example 1. Measurement equipment: UV-vis absorption spectrum: JASCO V-670 Sample solution: After washing each compound of Example 1, Example 2, and Comparative Example 1 with acetone, a sample solution with a sample concentration of 50 μmol / L was added to a dried 50 mL volumetric flask. -3 or 2mmoldm -3 The reason for choosing dehydrated ethanol was to prevent hydrolysis of the ethoxysilane moiety present in each compound. Measurement: The sample solution was placed in a quartz glass cell (1 cm) that had been washed with acetone and dried, and measurements were performed under the following conditions. UV-vis absorption spectrum measurement conditions: Bandwidth: 2 nm, Scanning speed: 200 nm / min, Response: Fast, Data acquisition interval: 1 nm

[0115] FIG. 2 shows the absorption spectrum obtained by simulation. FIG. 3 shows the observed spectrum of Comparative Example 1. As shown in FIGS. 2 and 3, in the case of the model compound having a diazirine group, absorption due to the n-π* transition of the diazirine group can be confirmed around 360 nm, but in the case of Comparative Example 1 having a diazomethyl group, no absorption was confirmed around 360 nm. Therefore, according to the simulation of Example 2, carbene can be generated with light of a longer wavelength than the diazomethyl group of Comparative Example 1, and therefore, photodegradation can be suppressed by using the reactivity imparting compound of the present disclosure.

[0116] Figure 4 shows the absorption spectrum of Example 1. Figure 4(a) shows the absorption spectrum of Example 1 at a sample concentration of 50 μmol / dm. -3 The absorption spectrum of the sample at a concentration of 2 mmol / L is shown in Fig. 4(b). -3 5 shows the absorption spectrum of Example 2. -3 The absorption spectrum of the sample at a concentration of 2 mmol / L is shown in Fig. 5(b). -3The measurement results are summarized in Table 1 below. abs means the light absorption wavelength (nm), and ε is the molar absorption coefficient (dm 3 mol -1 cm -1 ) means. The horizontal axis of Figures 4(a) and 4(b) is wavelength (nm), and the vertical axis is absorbance (arbitrary units). The horizontal axis of Figures 5(a) and 5(b) is wavelength (nm), and the vertical axis is absorbance (arbitrary units). As shown in Figures 4(b) and 5(b), two absorption bands were observed in the ultraviolet region below 400 nm for both Example 1 and Example 2. When analyzed in conjunction with the simulation results, the absorption band observed near 360 nm can be attributed to absorption derived from the n-π* transition of the diazirine group, i.e., absorption inducing photodecomposition to carbene. This proves that Example 1 and Example 2, which have diazirine groups, can generate carbene when irradiated with long-wavelength ultraviolet light (UVA), and can react with the substrate surface while suppressing photodegradation. Similarly, a light absorption peak was observed near 357 nm for Example 3 and Example 4.

[0117] [Table 1]

[0118] (Photodecomposition confirmation experiment 1 of diazirine unit) Next, an experiment was carried out to confirm whether the diazirine group in Examples 1 and 2 would decompose into carbene by irradiation with long-wavelength ultraviolet light (UVA) (wavelength 365 nm). 2 ,N 4 -bis(3-(triethoxysilyl)propyl)-1,3,5-triazine-2,4-diamine has no silane coupling moiety and is easy to handle, so 6-(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N 2 ,N 4A confirmation experiment was carried out using -dipropyl-1,3,5-triazine-2,4-diamine. Similarly, a confirmation experiment was carried out using 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-((3-triethoxysilyl)propyl)-1,3,5-triazine-2-amine of Reference Example 2 instead of 4,6-bis(2-(3-methyl-3H-diazirin-3-yl)ethoxy)-N-propyl-1,3,5-triazine-2-amine of Example 2. The measurement conditions were as follows: Measurement equipment: UV-vis absorption spectrum: JASCO V-670 Sample solution: After washing the compound of Reference Example 1 with acetone, add a solution of 4 mmol / L of sample to a dried 50 mL measuring flask. -3 The compound of Reference Example 2 was washed with acetone and then added to a dried 50 mL volumetric flask so that the sample concentration was 2 mmol / L. -3 The solution was weighed out so that the volume was equal to the amount of the solution, and then made up to the desired volume with dehydrated methanol. Measurement: The sample solution was placed in a quartz glass cell (1 cm) that had been washed with acetone and dried, and measurements were performed under the following conditions. UV-vis absorption spectrum measurement conditions: Bandwidth: 2 nm, Scanning speed: 200 nm / min, Response: Fast, Data acquisition interval: 1 nm Light source: AS ONE handy UV lamp (254nm / 365nm compatible) ·Light irradiation conditions: Wavelength: 365nm, time 0~40min

[0119] Figure 6 shows the change in absorption spectrum when the sample solution of Reference Example 1 is irradiated with light. Figure 7 shows the change in absorption spectrum when the sample solution of Reference Example 2 is irradiated with light. The horizontal axis represents wavelength, and the vertical axis represents absorbance (arbitrary units). As shown in Figures 6 and 7, it was found that the longer the irradiation time, the smaller the peak (near 360 nm) resulting from the n-π* transition of the diazirine group became. This indicates that the diazirine group was photodecomposed into carbene by light irradiation. Therefore, it was confirmed that the diazirine group can be decomposed into carbene by light irradiation at a wavelength of 365 nm.

[0120] (Photodecomposition confirmation experiment 2 of diazirine unit) To confirm that carbene is generated by photolysis of the diazirine group, Reference Examples 1 and 2 were each dissolved in methanol, and the photoreaction products were investigated by mass spectrometry before and after irradiating the solution with 365 nm UV light for 10 minutes. The measurement conditions were as follows: ·Measurement equipment: JEOL JMS-700 mass spectrometer Sample solution: 6 mg of sample was weighed into a sample bottle, and 3 mL of dehydrated methanol was added to make the sample solution. Light source: AS ONE handy UV lamp (254nm / 365nm compatible) Measurement: A portion of the prepared sample solution was placed in a sample bottle without any further manipulation, and this was used as the sample before UV irradiation. A portion of the remaining prepared solution was placed in a quartz cell, and the quartz cell was then irradiated with 365 nm UV light from a handy UV lamp for 10 minutes. The solution was then placed in a sample bottle, and this was used as the sample after UV irradiation. These were then analyzed by mass spectrometry.

[0121] In the mass spectrum (ionization method: electron ionization) of the sample solution of Reference Example 1 before irradiation with ultraviolet light, a molecular ion (M + On the other hand, in the mass spectrum of the sample solution after UV irradiation, a molecular ion (M + ) peak was detected. This peak is due to the 6-(3-methoxybutoxy)-N, which is generated by the hydroxyl group (OH group) of methanol through an OH insertion reaction with the carbene generated by photolysis of the diazirine group. 2 ,N 4This corresponds to the molecular weight of 297 of N-dipropyl-1,3,5-triazine-2,4-diamine. In the mass spectrum (ionization method: fast atom bombardment ionization) of the sample solution of Reference Example 2 before UV irradiation, a molecular ion peak at m / z 335 was detected. If m / z 335 is considered to be a protonated molecular ion species, the mass of this peak would be 334, which corresponds to the molecular weight of 334 of Reference Example 2. In the mass spectrum of the sample solution of Reference Example 2 after UV irradiation, a molecular ion peak at m / z 343 was detected. If m / z 343 is considered to be a protonated molecular ion species, the mass of this peak would be 342, which corresponds to the molecular weight of 342 of 4,6-bis(3-methoxybutoxy)-N-propyl-1,3,5-triazine-2-amine, which is produced by photolysis of two diazirine groups in the molecular structure, resulting in the formation of carbene, which then undergoes an OH insertion reaction with the hydroxyl group (OH group) of methanol. The photoreaction product detected was the insertion reaction product of carbene into the OH bond of the alcohol, confirming that the diazirine group can be decomposed into carbene by irradiation with light at a wavelength of 365 nm.

[0122] (Preparation of laminates using reactivity-imparting compounds and evaluation of peel strength) Next, laminates were produced using the reactivity-imparting compounds of Examples 1, 2, and 4, and the peel strength (adhesion) thereof was evaluated. The evaluation samples were prepared according to the following procedure.

[0123] "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.

[0124] "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.

[0125] "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.

[0126] "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.

[0127] An ABS substrate (1 mm x 30 mm x 130 μm thick) manufactured by Mitsubishi Chemical Corporation was used as the acrylonitrile butadiene styrene resin substrate (ABS substrate). The ABS substrate was immersed in ethanol, irradiated with ultrasonic waves for 10 minutes, cleaned, and then dried. After drying, the surface of the ABS substrate was subjected to corona treatment three times using a corona discharge device (Corona Master manufactured by Shinko Electric Instrumentation, voltage output: 12 kV, irradiation distance: 0.5 mm). The ABS substrate was then immersed in the ethanol solution (concentration 0.1 wt%) of Example 1 or Example 2 for 10 seconds and dried to form a reactivity-imparting compound layer. For Example 4, laminates were prepared both without and with corona discharge treatment.

[0128] After forming the reactivity imparting compound layer, the ABS substrate was irradiated with light from a high-pressure mercury lamp or an LED lamp. The dominant wavelength of light from both the high-pressure mercury lamp and the LED was 365 nm, and the illuminance was 17 mW / cm2, as measured with an ultraviolet integrating illuminometer UVPF-A2 (peak sensitivity 355 nm). 2 , 396mW / cm 2The irradiation time was 5 minutes. After the light irradiation, the ABS substrate was immersed in the pre-dip solution for 1 minute, and after immersion, without being washed, it was immersed in a catalyst solution at 50°C for 1 minute, and then washed with distilled water. Thereafter, without drying, the ABS substrate was immersed in an accelerator solution for 3 minutes and washed with distilled water. After washing, the ABS substrate, while still wet, was immersed in an electroless copper plating solution at 32°C for 15 minutes, washed with distilled water and ethanol, and dried. After drying, the ABS substrate (laminate) on which the copper layer was formed was annealed at 80°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 80° C. for 10 minutes to obtain a laminate using the reactivity-imparting compound of each Example.

[0129] "Peel strength measurement" A 1 cm wide cut was made in the copper layer of the laminate using the reactivity-imparting compounds of Examples 1 and 2, and the peel strength between the copper layer and the ABS substrate was measured using an adhesion tester (IMADA FORCE MEASUREMENT model mX2, manufactured by IMADA) at a pulling rate of 50 mm / min and a pulling angle of 90°. The results are shown in Table 2. The results of Example 4 with and without corona discharge treatment are shown in Table 3.

[0130] [Table 2]

[0131] [Table 3]

[0132] As shown in Table 2, when irradiated with ultraviolet light from a high-pressure mercury lamp, both laminates using Example 1 and Example 2 as the reactivity imparting compound exhibited high peel strength. It is believed that the carbene generated from Example 1 or Example 2 caused an OH insertion reaction with the hydroxyl groups (OH groups) on the substrate surface generated by corona discharge, forming a covalent bond between the reactivity imparting compound and the substrate surface, leading to high adhesion. Furthermore, because the number of hydroxyl groups introduced onto the substrate surface by corona discharge is small, it is difficult to achieve high adhesion without further treatment. However, we confirmed that adhesion can be improved by attaching the reactivity-imparting compounds of Examples 1 and 2 to the substrate surface via the photoreaction of diazirine groups to impart silanol-generating groups, thereby forming bonds between the silanol and the copper layer. When using an LED lamp, the laminate using Example 2, which has two diazirine groups in the molecule, exhibited higher peel strength than the laminate using Example 1, which has one diazirine group in the molecule. Furthermore, the laminate using a mercury lamp exhibited higher peel strength than the LED lamp. When using a high-pressure mercury lamp with a dominant wavelength of 365 nm and a wide spectrum in the ultraviolet region, carbene is easily generated, increasing the photoreaction efficiency between the reactivity-imparting compound and the substrate. Therefore, high plating adhesion can be achieved regardless of the number of diazirine groups in the molecule, regardless of the reactivity-imparting compound used. On the other hand, when an LED lamp with a narrow spectrum centered around 365 nm is used, carbene is less likely to be generated and the efficiency of the photoreaction between the reactivity imparting compound and the substrate is low, so higher adhesion can be obtained by using Example 2, which has many diazirine groups and a high probability of reaction with the substrate. On the other hand, as shown in Table 3, when the reactivity imparting compound of Example 4 was used, the peel strength was comparable whether a high-pressure mercury lamp or an LED lamp was used as the photoreaction light source. In addition, high peel strength was also observed even without corona treatment. This is thought to be because the reactivity imparting compound of Example 4 has a 3-trifluoromethyl-3-phenyldiazirine skeleton, which improves the photodecomposition efficiency of the diazirine group and enables not only OH insertion reaction but also CH insertion reaction of the generated carbene. From the above results, it is believed that reactivity-imparting compounds having diazirine groups are very useful as photoreactive molecular bonding agents. [Industrial Applicability]

[0133] The reactivity imparting compound, the method for producing the reactivity imparting compound, and the laminate of the present invention suppress photodegradation of the substrate and provide high adhesion, and therefore have high industrial applicability. [Explanation of symbols]

[0134] 1 substrate, 2 reactivity imparting compound layer, 3 metal layer, 100 laminate

Claims

1. 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-imparted compound represented by the following formula (18) to which one or more diazirine groups have been added; A method for producing a reactivity-imparting compound represented by formula (4) below, comprising a silane coupling moiety-imparting step of reacting the diazirine group-imparting compound represented by formula (18) below with 3-aminopropyltriethoxysilane, thereby obtaining a compound represented by formula (4) below. 【Chemistry 3】 【Chemistry 4】

2. 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-imparted compound represented by the following formula (20) to which one or more diazirine groups have been added; A method for producing a reactivity-imparting compound represented by the following formula (13), comprising a silane coupling moiety-imparting step of reacting the diazirine group-imparting compound represented by the following formula (20) with 3-aminopropyltriethoxysilane, thereby obtaining a compound of the following formula (13). 【Chemistry 5】 【Chemistry 6】

3. 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-imparted compound represented by the following formula (15) having one or more diazirine groups added thereto; A method for producing a reactivity-imparting compound represented by formula (12) below, comprising a silane coupling moiety-imparting step of reacting the diazirine group-imparting compound represented by formula (15) below with 3-aminopropyltriethoxysilane, thereby obtaining a compound represented by formula (12) below. 【Chemistry 7】 【Chemistry 8】

4. 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-imparted compound represented by the following formula (17) to which one or more diazirine groups have been added; A method for producing a reactivity-imparting compound represented by formula (14) below, comprising a silane coupling moiety-imparting step of reacting the diazirine group-imparting compound represented by formula (17) below with 3-aminopropyltriethoxysilane, thereby obtaining a compound represented by formula (14) below. 【Chemistry 9】 【Chemistry 10】

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