Dopamine compound, preparation method and application thereof

Abstract

The present application relates to the field of organic materials, in particular to a kind of dopa compound and its preparation method and application.The dopa compound has nitrogen-containing heterocyclic structure, using the compound can efficiently bond inorganic materials such as metal, metal oxide or organic resin, can realize the roughing without the condition, there is enough bonding force between materials, and there is good signal transmission effect, meet the requirement of high frequency high speed communication, and the application range of material is wider than existing coupling agent, and heat resistance is more superior, can guarantee the bonding effect between materials long-term stable in high temperature environment.The present application can be applied to the manufacture of PCB, such as the manufacture of multilayer laminated board, can also be used for the preparation of semiconductor components, can also be used for high frequency communication electronic components, such as dielectric ceramic bonding or metallization and the like, has good application prospect.

Description

Technical Field

[0001] This invention relates to the field of organic materials, specifically to a dopa-like compound, its preparation method, and its applications. Background Technology

[0002] With technological advancements, higher demands are being placed on the high-speed / high-frequency signal transmission performance of multilayer PCBs. The relatively smooth surface of HVLP copper foil results in insufficient contact area / bonding force between layers, impacting the performance of PCB products.

[0003] In existing production processes, a browning solution is typically used to grow a uniform layer of fluff on the copper surface of the substrate to improve the bonding between the layers. However, the waste liquid generated during the browning process causes significant environmental pollution.

[0004] Therefore, it is necessary to develop a new type of green and environmentally friendly adhesive that introduces chemical action to replace mechanical interlocking, while meeting the environmental protection requirements of the production process and reducing the cost of waste liquid treatment, thereby solving the problems existing in the current technology. Summary of the Invention

[0005] This invention provides a dopa-like compound, its preparation method, and its application. The dopa-like compound has a nitrogen-containing heterocyclic structure. Using this compound, inorganic materials such as metals and metal oxides or organic resins can be bonded efficiently. It can achieve sufficient bonding force between materials without coarsening and has good signal transmission effect, meeting the requirements of high-frequency and high-speed communication. Moreover, the material has a wider range of applications than existing coupling agents and has better heat resistance. It can also ensure long-term stability of the bonding effect between materials in high-temperature environments.

[0006] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0007] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R1s, then R1s can be independently selected from different groups.

[0008] The object of this invention is to provide a dopa-like compound, wherein the dopa-like compound is selected from the following structures:

[0009]

[0010] in,

[0011] The Ar is a nitrogen-containing heterocycle;

[0012] Z is selected from C=O or C=S;

[0013] The n is selected from integers from 0 to 12;

[0014] The m is selected from integers from 1 to 4.

[0015] Furthermore, the dopa-like compounds are selected from the following structures:

[0016]

[0017] in,

[0018] X1-X6 are independently selected from CR1 or N;

[0019] The Y is selected from O, S, NR1, CR1=CR1, C=O, CR1=N or C=NR1;

[0020] Z is selected from C=O or C=S;

[0021] The n is selected from integers from 0 to 12;

[0022] The m is selected from integers from 1 to 4;

[0023] R1 is independently selected from -H, -D, -OR2, -N(R2)2 or -SR2;

[0024] The R2 is independently selected from -H, -D, alkenyl, styryl, substituted or unsubstituted epoxy groups, and siloxanes.

[0025] Furthermore, among X1-X6, at least two are N.

[0026] Preferably, n is selected from an integer from 1 to 9. More preferably, n is selected from an integer from 1 to 5.

[0027] Preferably, m is selected from an integer from 1 to 9. More preferably, m is selected from an integer from 1 to 5.

[0028] Further, n represents the number of methylene groups, and m represents... The number of groups.

[0029] Another object of the present invention is to provide a method for preparing the aforementioned dopa-like compounds, comprising the following steps:

[0030] In a solvent, a compound having the structure of formula (I), formula (II), formula (III) or formula (IV) and a compound having the structure of formula (V) are mixed and heated to react, yielding the product;

[0031]

[0032]

[0033] in,

[0034] X1-X6 are independently selected from CR1 or N;

[0035] The Y is selected from O, S, NR1, CR1=CR1, C=O, CR1=N or C=NR1;

[0036] Z is selected from C=O or C=S;

[0037] The n is selected from integers from 0 to 12;

[0038] The m is selected from integers from 1 to 4;

[0039] R1 is independently selected from -H, -D, -OR2, -N(R2)2 or -SR2;

[0040] The R2 is independently selected from -H, -D, alkenyl, styryl, substituted or unsubstituted epoxy groups, and siloxanes;

[0041] The R3 is independently selected from halogen atoms or hydroxyl groups.

[0042] Furthermore, among X1-X6, at least two are N.

[0043] Understandably, the solvent does not react with compounds having the structures shown in formulas (I)-(V).

[0044] Preferably, the solvents include, but are not limited to: hydrocarbon solvents such as toluene, xylene, and n-hexane; alcohol solvents such as methanol and ethanol; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ketone solvents such as acetone and cyclohexanone; ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; ester solvents such as ethyl acetate and butyl acetate; acetonitrile, dimethyl sulfoxide, etc.

[0045] The amount of each raw material added should take into account factors such as reaction temperature, reaction time, type of raw material, type of solvent, and reaction scale.

[0046] Preferably, the molar ratio of the compound having the structure shown in formula (V) to the compound having the structure shown in formula (I) or formula (II) is 0.8-2.4.

[0047] Preferably, the molar ratio of the compound having the structure shown in formula (V) to the compound having the structure shown in formula (III) or (IV) is 0.8-2.4.

[0048] The reaction temperature is set to the temperature at which the chemical reaction can proceed smoothly.

[0049] Preferably, the temperature of the heating reaction is 0-150°C. More preferably, the temperature of the heating reaction is 50-100°C.

[0050] The reaction time is adjusted according to the set reaction temperature. Preferably, the heating reaction time is 0.5-24 hours. More preferably, the heating reaction time is 5-12 hours.

[0051] Understandably, some examples of compounds having the structure shown in formula (V) are given below:

[0052] 4-Aminophenyl-1,2-diol, 4-Formamidophenyl-1,2-diol, 2-(3,4-dihydroxyphenyl)methylamine, 2-(3,4-dihydroxyphenyl)formamide, 2-(3,4-dihydroxyphenyl)ethylamine, 2-(3,4-dihydroxyphenyl)acetamide, 2-(3,4-dihydroxyphenyl)propylamine, 2-(3,4-dihydroxyphenyl)propionamide, 2-(3,4-dihydroxyphenyl)butanamine, 2-(3,4-dihydroxyphenyl)butanamide, 2-(3,4-dihydroxyphenyl)pentanamine, 2-(3,4-dihydroxyphenyl)pentanamide, 2-(3,4-dihydroxyphenyl)hexylamine, 2-(3,4-dihydroxyphenyl)hexylamide, 2-(3,4-dihydroxyphenyl)octylamine, 2-(3,4-dihydroxyphenyl)octylamide.

[0053] Compounds having the structure shown in formula (I) or formula (II) and compounds having the structure shown in formula (III) or formula (IV) are partially exemplified below:

[0054] 1,2,4-triazole, 2,5-dimercaptothiadiazole, thiadiazole, benzimidazole.

[0055] Another object of the present invention is to provide a coupling agent comprising the above-mentioned dopa compounds and / or the products of oxidation, coordination, and cross-linking of the dopa groups in the dopa compounds.

[0056] Furthermore, the structure of the coupling agent is selected from formula (VI), formula (VII), formula (VIII), formula (IX) or the product of oxidation, coordination and crosslinking of catechol group in formula (VI), formula (VII), formula (VIII), formula (IX);

[0057]

[0058]

[0059] in,

[0060] X1-X6 are independently selected from CR1 or N;

[0061] The Y is selected from O, S, NR1, CR1=CR1, C=O, CR1=N or C=NR1;

[0062] Z is selected from C=O or C=S;

[0063] The n is selected from integers from 0 to 12;

[0064] The m is selected from integers from 1 to 4;

[0065] R1 is independently selected from -H, -D, -OR2, -N(R2)2 or -SR2;

[0066] The R2 is independently selected from -H, -D, alkenyl, styryl, substituted or unsubstituted epoxy groups, and siloxanes.

[0067] Furthermore, among X1-X6, at least two are N.

[0068] Understandably, dopa coupling agents having structures as shown in formulas (VI), (VII), (VIII) and (IX) can (1) adhere to adjacent dopa molecules through intermolecular hydrogen bonds; (2) adhere through coordination with metal cations; (3) adhere through π-π interactions between dopa molecules; (4) adhere through thiol reduction; (5) aggregate through cation-π interactions; and (6) have hydroxyl groups that can be oxidized and then aggregate intermolecularly.

[0069] Figure 1 This is a flowchart illustrating the various adhesion mechanisms of the coupling agent of this invention.

[0070] Another object of the present invention is to provide a surface treatment liquid, wherein the raw materials for preparing the surface treatment liquid include the above-mentioned dopa compounds, water and additives;

[0071] or

[0072] The raw materials for preparing the surface treatment liquid include the coupling agent and additives mentioned above.

[0073] Similarly, in order to improve the stability of the surface treatment solution and the uniformity of the chemical conversion film, substances that generate halogen ions such as chloride ions, bromide ions, and iodide ions, as well as metal ions such as copper ions, iron ions, and zinc ions can also be used.

[0074] In the preparation of the surface treatment solution, the dopa compound or dopa coupling agent of the present invention can be dissolved in an organic solvent and / or water. The organic solvent may include, but is not limited to, methanol, ethanol, 1-propanol, isopropanol, n-butanol, tert-butanol, ethylene glycol, diethylene glycol, glycerol, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol methyl ether, benzene, toluene, xylene, n-hexane, cyclohexane, dichloromethane, chloroform, dichlorobenzene, acetone, butanone, and other solvents.

[0075] Another object of the present invention is to provide a method for surface treatment of a material, including the step of contacting the material surface with the above-described surface treatment liquid.

[0076] Furthermore, the material is selected from inorganic materials and / or resin materials. The shape of the material is not limited.

[0077] Furthermore, the inorganic material is selected from at least one of metals, metal oxides, silicon-containing materials, ceramics, or magnetic materials;

[0078] The resin material is selected from at least one of acrylic resin, epoxy resin, modified epoxy resin, polyimide resin, modified polyimide resin, liquid crystal polymer, polyphenylene ether resin, polyphenylene sulfide resin, hydrocarbon resin or polytetrafluoroethylene resin.

[0079] Furthermore, the metal is selected from at least one of copper, aluminum, titanium, nickel, tin, iron, silver, gold, and their alloys;

[0080] The metal oxide is selected from at least one of copper oxide, cuprous oxide, iron oxide, calcium oxide, sodium oxide, magnesium oxide, barium oxide, aluminum oxide, zinc oxide, manganese heptaoxide, manganese zinc ferrite, or nickel zinc ferrite.

[0081] The silicon-containing material is selected from at least one of silicon, glass, silicon carbide, silicon dioxide, glass or diatomaceous earth;

[0082] The ceramic contains at least one of nitrogen boride, titanium boride, zirconium boride, magnesium titanate, calcium titanate, barium titanate, aluminum nitride, or silicon nitride.

[0083] The magnetic material contains at least one of manganese-zinc ferrite or nickel-zinc ferrite.

[0084] The surface treatment liquid of the present invention can be brought into contact with the material surface using conventional methods, such as spraying or immersion.

[0085] The contact time between the surface treatment liquid and the material is not particularly limited, but is preferably 1s-24h, and more preferably 10s-1h, so that the surface treatment liquid can interact with the material surface.

[0086] The temperature of the surface treatment liquid when in contact with the material is preferably 0℃-80℃, more preferably 20℃-50℃.

[0087] After the surface treatment liquid comes into contact with the material, it can be left to stand at room temperature, or it can be dried directly with cold or hot air, or dried at 50℃-200℃.

[0088] By using the surface treatment liquid of the present invention to treat the surface of a material, an organic film can be formed on the surface of the material, thereby improving the adhesion to other materials.

[0089] Another object of the present invention is to provide a method for bonding materials, comprising the following steps:

[0090] The surface treatment liquid described above is used to contact the first material to form a thin film, which is then bonded to the second material.

[0091] Furthermore, the first material and the second material are independently selected from inorganic materials and / or resin materials.

[0092] Another object of the present invention is to provide an adhesive material prepared by the above-described bonding method between materials.

[0093] Another object of the present invention is to provide an electronic device comprising the above-described adhesive material.

[0094] Compared with the prior art, the present invention has the following beneficial effects:

[0095] This invention designs nitrogen-containing heterocyclic dopa compounds with special molecular structures. While retaining the structural characteristics of dopa coupling agents, it introduces or modifies functional groups at specific positions, resulting in a final compound with a wider range of material applications and higher temperature resistance compared to existing silane coupling agents. This ensures that the performance of the resulting adhesive materials and electronic components meets the requirements of high-frequency and high-speed communication.

[0096] When using a surface treatment liquid adhesive material with the nitrogen-containing heterocyclic dopa compound of the present invention as the main component, the peel strength between materials can be guaranteed and the bonding force can be improved without the need for surface roughening. It also has good heat resistance and can be applied to the manufacture of PCBs, such as the manufacture of multilayer laminates, the preparation of semiconductor components, and high-frequency communication electronic components, such as the bonding or metallization of dielectric ceramics, etc., showing good application prospects. Attached Figure Description

[0097] Figure 1 This is a flowchart illustrating the various adhesion mechanisms of the coupling agent of this invention.

[0098] Figure 2 This is a schematic diagram of the peel strength test plate being pressed together.

[0099] Figure 3 This is a schematic diagram of the reflow soldering test board pressing. Detailed Implementation

[0100] The present invention will be further described in detail below with reference to specific embodiments. The present invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of the present invention.

[0101] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the specification of this invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0102] Unless otherwise specified, the following specific embodiments are all conventional methods; unless otherwise specified, the raw materials, reagents and other materials used in the following specific embodiments are all commercially available products.

[0103] The following examples are intended to further illustrate the present invention, but are not intended to limit its scope.

[0104] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0105] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R1s, then R1s can be independently selected from different groups.

[0106] All operations in the following detailed embodiments can be performed at atmospheric pressure.

[0107] Example 1

[0108] A dopa-like compound has the following structure:

[0109]

[0110] The preparation method of the dopa-like compound includes the following steps:

[0111] Dihydroxybenzylamine (8.35 g, 60 mmol) was dissolved in chloroform (30 mL), and triethylamine (25.23 g, 250 mmol) was added. The mixture was stirred at 75 °C until a clear solution was obtained. Then, 5-chlorobenzotriazole (7.68 g, 50 mmol) was added, and the mixture was stirred until completely dissolved. The reaction was carried out at 75 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain the crude product. The crude product was purified by gradient elution on a silica gel column (ethyl acetate:hexane = 1:1) to obtain a pale yellow oily substance (10.32 g, 40 mmol, yield 80%).

[0112] The 1H NMR spectrum of the obtained oily substance is as follows:

[0113] 1H NMR(500MHz,Chloroform-d)δ13.48(s,1H),7.65(d,1H),7.20(d,1H),6.86(dd,1 H),6.73-6.70(m,3H),6.62(s,1H),6.29(s,1H),5.38(t,1H),4.38-4.37(dd,2H).

[0114] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f1.

[0115] Example 2

[0116] A dopa-like compound has the following structure:

[0117]

[0118] The preparation method of the dopa-like compound includes the following steps:

[0119] Dihydroxybenzylamine (15.30 g, 110 mmol) was dissolved in dry N,N-dimethylformamide (30 mL), and triethylamine (25.23 g, 250 mmol) was added. The mixture was stirred at 75 °C until a clear solution was obtained. Then, 3,5-dichloro-1H-1,2,4-triazole (6.70 g, 50 mmol) was added, and the mixture was stirred until completely dissolved. The reaction was carried out at 75 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain the crude product. The crude product was purified by silica gel column gradient elution (ethyl acetate:hexane = 1:5) to obtain a white oily substance (14.58 g, 42.5 mmol, yield 85%).

[0120] The 1H NMR spectrum of the obtained oily substance is as follows:

[0121] 1 H NMR (500MHz, Chloroform-d) δ10.44(s,1H),6.73-6.69(m,6H),6.45(s,2H),6.29(s,2H),5.69(t,2H),4.70-4.60(m,4H).

[0122] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f2.

[0123] Example 3

[0124] A dopa-like compound has the following structure:

[0125]

[0126] The preparation method of the dopa-like compound includes the following steps:

[0127] Dihydroxybenzylamine (15.30 g, 110 mmol) was dissolved in dry chloroform (30 mL), and triethylamine (25.23 g, 250 mmol) was added. The mixture was stirred at 75 °C until a clear solution was obtained. Then, 5,6-dichloro-1H-benzotriazole (9.40 g, 50 mmol) was added, and the mixture was stirred until completely dissolved. The reaction was carried out at 75 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain the crude product. The crude product was purified by gradient elution on a silica gel column (ethyl acetate:hexane = 1:5) to obtain a yellow oily substance (14.74 g, 37.5 mmol, yield 75%).

[0128] The 1H NMR spectrum of the obtained oily substance is as follows:

[0129] 1 H NMR(500MHz,Chloroform-d)δ12.22(s,1H),7.18(s,1H),6.78(s,1H),6.73(m,2H),6.70(s,4H),6.62(s,2H),6.29(s,2H),6.06(q,2H),4.40(d,4H).

[0130] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f3.

[0131] Example 4

[0132] A dopa-like compound has the following structure:

[0133]

[0134] The preparation method of the dopa-like compound includes the following steps:

[0135] 5-Carboxybenzotriazole (0.82 g, 5 mmol) was dissolved in dry N,N-dimethylformamide (30 mL), and N,N-diisopropylethylamine (6.46 g, 50 mmol) was added. The mixture was stirred at 80 °C until a clear solution was obtained. Then, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (7.60 g, 20 mmol) was added, and the reaction was carried out at 80 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain a crude product. The crude product was purified by gradient elution on a silica gel column (ethyl acetate:hexane = 1:3) to obtain a pale yellow oil (1.13 g, 4 mmol, 80% yield).

[0136] The 1H NMR spectrum of the obtained oily substance is as follows:

[0137] 1 H NMR(500MHz,Chloroform-d)δ14.10(s,1H),8.72(t,1H),8.30(d,1H),8.16(s ,1H),7.95-7.89(m,2H),6.76-6.62(m,3H),6.29(s,1H),4.47-4.46(dt,2H).

[0138] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f4.

[0139] Example 5

[0140] A dopa-like compound has the following structure:

[0141]

[0142] The preparation method of the dopa-like compound includes the following steps:

[0143] 4H-1,2,4-triazol-3,5-dicarboxylic acid (0.79 g, 5 mmol) was dissolved in dry N,N-dimethylformamide (30 mL), and N,N-diisopropylethylamine (12.92 g, 100 mmol) was added. The mixture was stirred at 80 °C until a clear solution was obtained. Then, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (15.20 g, 40 mmol) was added, and the reaction was carried out at 80 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain a crude product. The crude product was purified by gradient elution on a silica gel column (ethyl acetate:hexane = 1:3) to obtain a pale yellow oil (1.60 g, 4 mmol, 80% yield).

[0144] The 1H NMR spectrum of the obtained oily substance is as follows:

[0145] 1 H NMR (500MHz, Chloroform-d) δ11.46(s,1H),8.58(t,2H),6.76-6.69(m,6H),6.62(s,2H),6.29(s,2H),4.65(dt,4H).

[0146] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f5.

[0147] Example 6

[0148] A dopa-like compound has the following structure:

[0149]

[0150] The preparation method of the dopa-like compound includes the following steps:

[0151] 1,2-Benzenediol, 4-(bromomethyl) (10.10 g, 50 mmol) was dissolved in chloroform (30 mL), and triethylamine (25.23 g, 250 mmol) was added. The mixture was stirred at 75 °C until a clear solution was obtained. Then, 5-aminobenzotriazole (6.70 g, 50 mmol) was added, and the mixture was stirred until completely dissolved. The reaction was carried out at 75 °C for 24 h. After cooling to room temperature, the solution was transferred to a separating funnel containing 30 mL of water. DCM (25 mL) was added to the separating funnel for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated to obtain a crude product. The crude product was purified by silica gel column gradient elution (ethyl acetate:hexane = 1:1) to obtain a pale yellow oil (10.32 g, 40 mmol, yield 80%).

[0152] The 1H NMR spectrum of the obtained oily substance is as follows:

[0153] 1 H NMR(500MHz,Chloroform-d)δ13.48(s,1H),7.65(d,1H),7.20(d,1H),6.86(dd,1 H),6.73-6.70(m,3H),6.62(s,1H),6.29(s,1H),5.38(t,1H),4.38-4.37(dd,2H).

[0154] Based on these spectral data, the oily substance obtained in this embodiment was identified as a dopa-like compound represented by chemical formula f6.

[0155] Test case

[0156] Test method:

[0157] (1) Preparation of surface treatment solution

[0158] 5g each of the dopa-like compounds prepared in Examples 1-5 and 4-(aminomethyl)benzene-1,2-diol (without nitrogen heterocyclic structure) were dissolved in 250g of ethylene glycol monobutyl ether, and then 250g of deionized water was added to each. The mixtures were stirred at room temperature for 24h to obtain surface treatment solutions (1)-(6). A blank surface treatment solution (7) containing only 250g of ethylene glycol monobutyl ether and 250g of deionized water without any dopa-like compounds was prepared. All of the above surface treatment solutions were kept for later use.

[0159] (2) Processing flow

[0160] Pickling (room temperature, 60s) — water washing — alkaline washing (30℃, 60s) — water washing — surface treatment solution treatment (30℃, 60s) — water washing — drying (100℃, 10min).

[0161] (3) Fabrication of the test board

[0162] 1. The peel strength test involves placing M6 resin (polyphenylene oxide resin) on a standard copper-clad laminate, then placing the smooth side of the surface-treated copper foil facing the resin, with the lamination structure as shown. Figure 2 As shown, the final pressing is performed according to the pressing conditions of M6 resin.

[0163] 2. The heat resistance (lead-free reflow soldering) test involves placing M6 resin on a standard copper-clad laminate that has undergone surface treatment, then placing the rough side of the standard copper foil towards the resin, and laminating the structure as follows: Figure 3 As shown, the final pressing is performed according to the pressing conditions of M6 resin.

[0164] (4) Adhesion evaluation test

[0165] The peel strength was determined using a 7cm x 8cm ordinary electrolytic copper foil (1 ounce) according to the standard “IPC-TM-650 No.2.4.8”.

[0166] (5) Heat resistance evaluation test

[0167] The heat resistance (lead-free reflow soldering) was determined using a 7cm × 8cm ordinary electrolytic copper foil (1 ounce) in accordance with the standard “IPC-TM-650 No.2.6.8”.

[0168] Figure 2 This is a schematic diagram of the peel strength test plate being pressed together.

[0169] Figure 3 This is a schematic diagram of the reflow soldering test board pressing.

[0170] The test results are shown in Table 1:

[0171] Table 1 Performance Test Results

[0172]

[0173]

[0174] The above results show that the bonding strength between adhesive materials treated with the dopamine compounds of this invention is greater than 3.0 Ib / in, and the number of reflow soldering (thermal shock) cycles is more than 10, indicating good mechanical properties and thermal stability. In contrast, adhesive materials treated with 4-(aminomethyl)benzene-1,2-diol (without nitrogen-containing heterocycles) do not meet the requirements for mechanical properties and thermal stability. Treating materials with a blank treatment solution containing no dopamine compounds does not result in any bonding ability or thermal stability loss. In summary, this invention has excellent technical effects and solves the problems existing in the prior art.

[0175] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0176] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of the present invention. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these modifications and improvements all fall within the scope of protection of the present invention. Therefore, the scope of protection of this patent should be determined by the appended claims.

Claims

1. A dopa-like compound, characterized in that, The dopamine compounds are selected from the following structures: or or or or 。 2. A coupling agent, characterized in that, The coupling agent includes the dopa-like compound of claim 1.

3. A surface treatment liquid, characterized in that, The raw materials for preparing the surface treatment liquid include the dopa-like compound of claim 1, water, and additives.

4. A method for surface treatment of a material, characterized in that, The method for surface treatment of the material includes the step of contacting the surface of the material with the surface treatment liquid of claim 3.

5. A method for bonding materials, characterized in that, The bonding method between the materials includes the following steps: The surface treatment liquid of claim 3 is used to contact the first material to form a thin film, which is then bonded to the second material.

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