Silane coupling agent and preparation method thereof, resin composition, cured film and semiconductor device

Abstract

The present application relates to a silane coupling agent and its preparation method, resin composition, cured film and semiconductor device. The structural formula of the silane coupling agent is shown in formula (I): #imgabs0# In formula (I), X1 and X2 are each independently selected from a nitrogen atom and a carbon atom; Y is an oxygen atom and a sulfur atom; R1 is an alkyl group with 1 to 10 carbon atoms and an alkoxy group with 1 to 10 carbon atoms; R2, R3 and R4 are each independently selected from an alkyl group with 1 to 5 carbon atoms and an alkoxy group with 1 to 5 carbon atoms. The silane coupling agent provided in the application embodiment not only has good compatibility with organic materials, but also has good bonding ability with inorganic interfaces. When the silane coupling agent is added to the resin composition, it can improve the adhesion of the resin composition to the substrate surface after curing and reduce the risk of delamination of the resin composition from the substrate after curing.

Description

Technical Field

[0001] The present application relates to the technical field of resin compositions, and in particular to a silane coupling agent and a preparation method thereof, a resin composition, a cured film, and a semiconductor device. Background Art

[0002] Resins such as polyimide (PI) and polybenzoxazole (PBO) are widely used for surface passivation of integrated circuit chips and in the surface redistribution layer (RDL) process of wafer-level packaging (WLP) due to their excellent heat resistance and mechanical properties after thermal curing. They serve as stress buffers, expand the chip packaging area, and protect the chip within the chip packaging structure, making them key core materials for WLP. However, traditional polyimide and polybenzoxazole resins often lack adhesion to substrates (such as metal and silicon), leading to microvoids and even cracks at the interface. Summary of the Invention

[0003] The embodiments of the present application provide a silane coupling agent and a preparation method thereof, a resin composition, a cured film and a semiconductor device to at least partially solve the above-mentioned technical problems.

[0004] In order to achieve the above-mentioned object, according to the first aspect of the present application, a silane coupling agent is provided, and the structural formula of the silane coupling agent is shown in formula (I):

[0005] Formula (I),

[0006] In formula (I), X1 and X2 are each independently selected from a nitrogen atom and a carbon atom; Y is an oxygen atom and a sulfur atom; R1 is an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms; R2, R3 and R4 are each independently selected from an alkyl group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms.

[0007] Optionally, one of X1 and X2 is a nitrogen atom.

[0008] Alternatively, Y is a sulfur atom.

[0009] Optionally, R1 is a saturated alkyl group having 1 to 4 carbon atoms.

[0010] Optionally, R1 is a straight-chain saturated alkyl group having 2 to 3 carbon atoms.

[0011] Optionally, R2, R3 and R4 are each independently selected from any one of an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms.

[0012] Optionally, based on R2, R3 and R4, the number of the alkoxy groups is less than or equal to 2.

[0013] Optionally, based on R2, R3 and R4, the number of the alkoxy groups is greater than the number of the alkyl groups.

[0014] Optionally, R2, R3 and R4 are each independently selected from any one of methyl, ethyl, methoxy and ethoxy, and based on R2, R3 and R4, the number of the methyl groups is 0 or 1, and the number of the ethyl groups is 0 or 1.

[0015] According to a second aspect of the present application, a method for preparing a silane coupling agent is provided, which is used to prepare the silane coupling agent as described above, comprising:

[0016] The silane coupling agent is obtained by performing a nucleophilic substitution reaction between the first compound and the second compound, wherein the structural formula of the first compound is shown in formula (II):

[0017] Formula (II),

[0018] In formula (II), Z is any one of a hydroxyl group and a thiol group, and R1, R2, R3 and R4 are the same as those in formula (I);

[0019] The structural formula of the second compound is shown in formula (III):

[0020] Formula (III),

[0021] In formula (III), W is a halogen atom that replaces at least one hydrogen atom on the aromatic ring, and X1 and X2 are the same as those in formula (I).

[0022] Alternatively, W is a fluorine atom or a chlorine atom, and the substitution number is 1.

[0023] Optionally, the molar ratio of the first compound to the second compound is 1:1.

[0024] Optionally, the first compound and the second compound undergo the nucleophilic substitution reaction in a polar solvent.

[0025] Optionally, the polar solvent is a polar aprotic solvent.

[0026] Optionally, the polar aprotic solvent includes at least one of N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and N,N-diethylformamide.

[0027] Optionally, the first compound and the second compound undergo the nucleophilic substitution reaction under the catalysis of a basic catalyst.

[0028] Optionally, the basic catalyst includes at least one of an organic base and an inorganic base.

[0029] Optionally, the organic base includes triethylamine, pyridine, sodium methoxide, sodium ethoxide, and N,N - at least one of diisopropylethylamine.

[0030] Optionally, the inorganic base includes at least one of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide and potassium hydroxide.

[0031] Optionally, the molar ratio of the alkaline catalyst to the first compound is 1-10.

[0032] Optionally, the molar ratio of the alkaline catalyst to the first compound is 1 to 1.5.

[0033] Optionally, the reaction temperature of the nucleophilic substitution reaction is 10°C to 50°C.

[0034] Optionally, after the nucleophilic substitution reaction is completed, a reaction liquid containing the silane coupling agent is obtained, and the preparation method of the silane coupling agent further includes purifying the reaction liquid to extract the silane coupling agent from the reaction liquid.

[0035] According to a third aspect of the present application, a resin composition is provided, comprising a silane coupling agent and a resin, wherein the silane coupling agent is at least one of the silane coupling agent described above and a silane coupling agent prepared by the method for preparing the silane coupling agent described above.

[0036] Optionally, the mass ratio of the silane coupling agent to the resin is 0.001-0.1.

[0037] Optionally, the resin composition is a photosensitive resin composition, and the photosensitive resin composition further comprises a photoinitiator.

[0038] Optionally, the photosensitive resin composition further includes at least one of a cross-linking agent and a first solvent.

[0039] Optionally, the resin is an alkali-soluble resin.

[0040] Optionally, the alkali-soluble resin includes at least one of polyimide resin, polyamic acid resin, polyamic acid ester resin and polybenzoxazole resin.

[0041] According to a fourth aspect of the present application, a cured film is provided, comprising a cured product of the above-mentioned resin composition.

[0042] Alternatively, the cured film includes at least one of a surface protection film, an interlayer insulating film, a redistribution insulating film, a metal bump stress buffer layer, and a passivation film for a semiconductor package element.

[0043] According to a fifth aspect of the present application, a semiconductor device is provided, comprising the cured film as described above.

[0044] The silane coupling agent provided in the application examples not only has good compatibility with organic materials, but also has good bonding ability with inorganic interfaces. In particular, the silane coupling agent contains both silane groups and benzotriazole groups, which enables the silane coupling agent to have better bonding ability with metal substrates (especially copper surfaces). In this way, when the silane coupling agent is added to the resin composition, the adhesion of the resin composition to the substrate surface after curing can be improved, and the risk of delamination of the cured film formed after curing of the resin composition from the substrate can be reduced.

[0045] Other features and advantages of the present application will be described in detail in the subsequent detailed description. DETAILED DESCRIPTION

[0046] The technical solutions in the embodiments of the present application are described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of the present application, not all of them. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application.

[0047] According to a first aspect of the embodiments of the present application, the embodiments of the present application provide a silane coupling agent, the structural formula of the silane coupling agent is shown in formula (I):

[0048] Formula (I),

[0049] In formula (I), X1 and X2 are each independently selected from a nitrogen atom and a carbon atom; Y is an oxygen atom and a sulfur atom; R1 is an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms; R2, R3 and R4 are each independently selected from an alkyl group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms.

[0050] As can be seen from formula (I), the silane coupling agent contains two types of groups, namely silane groups and benzotriazole groups. The silane group is connected to the benzotriazole group through Y. Y can be an oxygen atom or a sulfur atom. Oxygen and sulfur both belong to the oxygen family and have 6 outermost electrons. Therefore, the two have certain similarities in chemical properties.

[0051] Specifically, the aromatic ring of the benzotriazole group has X1 and X2, where X1 and X2 are each independently selected from a nitrogen atom and a carbon atom. As an example, X1 and X2 are both carbon atoms, so that the aromatic ring is a benzene ring. As an example, X1 and X2 are both nitrogen atoms, or one of X1 and X2 is a carbon atom and the other of X1 and X2 is a nitrogen atom, so that the aromatic ring is an azaaromatic ring.

[0052] Silane groups include R1, R2, R3, and R4. R1 can be an alkyl group with 1 to 10 carbon atoms, or an alkoxy group with 1 to 10 carbon atoms. Any one of R2, R3, and R4 can be an alkyl group with 1 to 5 carbon atoms, or an alkoxy group with 1 to 5 carbon atoms. In other words, R2, R3, and R4 in a silane group can be the same or different. For example, R2, R3, and R4 are all alkoxy groups, or R2, R3, and R4 are all alkyl groups, or one of R2, R3, and R4 is an alkoxy group and the other two are alkyl groups, or one of R2, R3, and R4 is an alkyl group and the other two are alkoxy groups.

[0053] Y is bonded to the aromatic ring in the benzotriazole group, more specifically, to a carbon atom on the aromatic ring. The specific carbon atom on the aromatic ring to which a single Y is bonded can be selected as needed. For example, a single Y can be bonded to a carbon atom on the aromatic ring that is close to X1 or X2, or to a carbon atom on the aromatic ring that is far from X1 or X2. If X1 or X2 is a carbon atom, it can also be bonded to that carbon atom.

[0054] In addition, in formula (I), the number of silane groups can be one or more. When the number of silane groups is multiple, the number of Y is also multiple, so that different Ys can be connected to different carbon atoms on the aromatic ring. Alternatively, the number of silane groups is one, which makes it easier to control the difficulty of preparing the silane coupling agent.

[0055] The silane coupling agent provided in the application examples not only has good compatibility with organic materials, but also has good bonding ability with inorganic interfaces. In particular, the silane coupling agent contains both silane groups and benzotriazole groups, which enables the silane coupling agent to have better bonding ability with metal substrates (especially copper surfaces). In this way, when the silane coupling agent is added to the resin composition, the adhesion of the resin composition to the substrate surface after curing can be improved, and the risk of delamination of the cured film formed after curing of the resin composition from the substrate can be reduced.

[0056] At the same time, the silane coupling agent added to the resin composition does not affect the storage stability of the resin composition. In addition, the silane coupling agent added to the resin composition can maintain good adhesion to the substrate even at a low curing temperature (≤250°C).

[0057] In some embodiments, one of X1 and X2 is a nitrogen atom. In other words, the aromatic ring is an azaaromatic ring having one nitrogen atom, which helps to enhance the bonding ability of the benzotriazole group with the inorganic interface, thereby improving the adhesion of the resin composition to the substrate surface after curing.

[0058] In some embodiments, Y is a sulfur atom. This arrangement can reduce the difficulty of preparing the silane coupling agent.

[0059] In some embodiments, R1 is a saturated alkyl group having 1 to 4 carbon atoms. Within this range, the silane coupling agent and the resin can have good compatibility. As an example, R1 is -CH2-, -CH2CH2-, -CH2CH2CH2-, -CHCH(CH3)-, -CH2CH2CH2CH2-, -CHC(CH3)2-, -CH(CH3)CH(CH3)-, or -CHCH(CH3)CH2-.

[0060] In some embodiments, R1 is a linear saturated alkyl group with 2 to 3 carbon atoms. The regular arrangement of the atoms in the linear saturated alkyl group can improve the solubility of the silane group and thereby enhance the bonding ability of the silane group with the inorganic interface. For example, R1 is -CH2CH2- or -CH2CH2CH2-.

[0061] In some embodiments, R2, R3, and R4 are each independently selected from an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms. For example, R2, R3, and R4 are each independently methyl (—CH3), ethyl (—CH2CH3), methoxy (—OCH3), or ethoxy (—OCH2CH3).

[0062] In some embodiments, the number of alkoxy groups based on R2, R3 and R4 is less than or equal to 2. That is, at least one of R2, R3 and R4 is an alkyl group, and at most two of the three are alkoxy groups. Generally, alkoxy groups are easily hydrolyzed with water and remove hydroxide ions (OH - Increasing the number of alkoxy groups in the silane coupling agent helps improve the bonding ability of the silane coupling agent to the metal substrate (especially the copper surface). However, excessive alkoxy groups can reduce the stability of the silane coupling agent because the silane coupling agent is more likely to be attacked by water, which in turn makes the resin composition containing the silane coupling agent more likely to become cloudy. As an example, based on R2, R3, and R4, the number of alkoxy groups is 1 or 2.

[0063] In some embodiments, the number of alkoxy groups is greater than the number of alkyl groups based on R2, R3, and R4. Increasing the number of alkoxy groups can improve the bonding ability of the silane group to inorganic interfaces. For example, R2, R3, and R4 are all alkoxy groups, or two of R2, R3, and R4 are alkoxy groups and the other is an alkyl group. For example, the metal material includes copper.

[0064] In some embodiments, R2, R3 and R4 are each independently selected from any one of methyl, ethyl, methoxy and ethoxy, and based on R2, R3 and R4, the number of methyl groups is 0 or 1, and the number of ethyl groups is 0 or 1. As an example, R2, R3 and R4 are all methoxy groups, or R2, R3 and R4 are all ethoxy groups, or one of R2, R3 and R4 is ethoxy and the other two are methoxy groups, or one of R2, R3 and R4 is methoxy and the other two are ethoxy groups, or one of R2, R3 and R4 is methoxy and the other two are ethoxy groups, or one of R2, R3 and R4 is methoxy, one of ethoxy and one of methyl groups, or one of R2, R3 and R4 is methoxy, one of ethoxy and one of ethyl groups, or two of R2, R3 and R4 are methoxy and one of methyl groups, or two of R2, R3 and R4 are methoxy and one of ethyl groups, or two of R2, R3 and R4 are ethoxy and one of methyl groups, or two of R2, R3 and R4 are ethoxy and one of ethyl groups.

[0065] According to a second aspect of the embodiments of the present application, the embodiments of the present application provide a method for preparing a silane coupling agent, which is used to prepare the silane coupling agent as described above, comprising:

[0066] The first compound and the second compound are subjected to a nucleophilic substitution reaction to obtain a silane coupling agent, wherein the structural formula of the first compound is shown in formula (II):

[0067] Formula (II),

[0068] In formula (II), Z is any one of a hydroxyl group and a thiol group, and R1, R2, R3 and R4 are the same as those in formula (I);

[0069] The structural formula of the second compound is shown in formula (III):

[0070] Formula (III),

[0071] In formula (III), W is a halogen atom that replaces at least one hydrogen atom on the aromatic ring, and X1 and X2 are the same as those in formula (I).

[0072] Since in formula (II), R1, R2, R3 and R4 are the same as those in formula (I); in formula (III), X1 and X2 are the same as those in formula (I), please refer to the above description and will not be repeated here.

[0073] In formula (II), Z may be a hydroxyl group or a thiol group.

[0074] In formula (III), W is a halogen atom. W is a substitution of at least one hydrogen atom on the aromatic ring, that is, at least one hydrogen atom on the aromatic ring is replaced by a halogen atom, that is, the number of halogen atoms on the aromatic ring is at least one. Specifically, the halogen atom is connected to a carbon atom on the aromatic ring. Usually, the specific carbon atom on the aromatic ring to which a single halogen atom is connected can be selected according to needs. As an example, a single halogen atom can be connected to a carbon atom on the aromatic ring close to X1 or X2, or to a carbon atom on the aromatic ring far away from X1 or X2, and can also be connected to the carbon atom when X1 or X2 is a carbon atom. The halogen atom here includes a fluorine atom (F), a chlorine atom (Cl), a bromine atom (Br) or an iodine atom (I).

[0075] The first compound and the second compound undergo a nucleophilic substitution reaction to generate the target silane coupling agent. Specifically, the first compound is a nucleophilic reagent, which removes protons under alkaline conditions and forms a bond with the carbon atom connected to the halogen atom on the second compound to form an intermediate. Then, the halide ion leaves as a leaving group, and finally forms a new oxygen ether or thioether compound, i.e., the silane coupling agent shown in formula (II).

[0076] The silane coupling agent prepared by the preparation method of the silane coupling agent provided in the second aspect of the embodiment of the present application is the same as the silane coupling agent provided in the first aspect of the embodiment of the present application. Therefore, the silane coupling agent prepared by the preparation method of the silane coupling agent has all the beneficial effects of the above-mentioned silane coupling agent, which will not be repeated in this application.

[0077] In some embodiments, W is a fluorine atom or a chlorine atom, and the number of substitutions is 1. This means that only one hydrogen atom on the aromatic ring is replaced by a halogen atom, and the number of halogen atoms on the aromatic ring is one. For example, there is one fluorine atom attached to the aromatic ring, or one chlorine atom attached to the aromatic ring. Since the halogen atom is attached to the aromatic ring, by designing the halogen atom as a fluorine atom or a chlorine atom, the difficulty of the halogen atom leaving the aromatic ring can be reduced, thereby increasing the rate of the nucleophilic substitution reaction.

[0078] In some embodiments, the molar ratio of the first compound to the second compound is 1:1. When only one hydrogen atom on the aromatic ring of the second compound is substituted with a halogen atom, by controlling the molar ratio of the first compound to the second compound as the reaction raw materials to be 1:1, the first compound and the second compound can react completely or substantially completely, thereby improving the utilization rate of the raw materials and reducing waste.

[0079] In some embodiments, the first and second compounds undergo a nucleophilic substitution reaction in a polar solvent. Polar solvents refer to solvents containing polar groups such as hydroxyl or carbonyl groups, i.e., solvent molecules that are polar. Polarity is generated by the misalignment of the centers of gravity of positive and negative charges within the molecules. Polar solvents can stabilize intermediates through solvation, reducing the activation energy required for their formation, thereby accelerating the rate of the nucleophilic substitution reaction.

[0080] In some embodiments, the polar solvent is a polar aprotic solvent. Aprotic solvents refer to solvents that have extremely weak or no proton self-transfer reaction. Such solvents do not donate protons in chemical reactions and are therefore also called aprotic solvents. By controlling the polar solvent to a polar aprotic solvent, the polar aprotic solvent is less likely to combine with nucleophilic reagents, thereby reducing its nucleophilicity. In addition, the polar aprotic solvent can also improve the stability of the generated silane coupling agent and reduce the risk of the silane coupling agent reacting with the solvent and decomposing.

[0081] In some embodiments, the polar aprotic solvent includes at least one of N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and N,N-diethylformamide.

[0082] In some embodiments, the first compound and the second compound undergo a nucleophilic substitution reaction under the catalysis of a basic catalyst. The basic catalyst can deprotonate the first compound, which is a nucleophilic reagent, thereby increasing its nucleophilicity.

[0083] In some embodiments, the basic catalyst comprises at least one of an organic base and an inorganic base. Alternatively, the organic base comprises at least one of triethylamine, pyridine, sodium methoxide, sodium ethoxide, and N,N-diisopropylethylamine. Alternatively, the inorganic base comprises at least one of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, and potassium hydroxide.

[0084] In some embodiments, the molar ratio of the alkaline catalyst to the first compound is 1 to 10. In the case where only one hydrogen atom on the aromatic ring of the second compound is replaced by a halogen atom, by controlling the amount of the alkaline catalyst to be appropriately greater than the amount of the first compound used as a nucleophile, that is, the alkaline catalyst is excessive, this can promote as many first compounds as possible to lose protons and improve the efficiency of the reaction of the first compound. However, alkaline catalysts are generally corrosive, so the molar ratio of the alkaline catalyst to the first compound should not be too large, otherwise it will increase the damage to the production setting and also increase the difficulty of purifying the silane coupling agent. As an example, the molar ratio of the alkaline catalyst to the first compound is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0085] In some embodiments, the molar ratio of the basic catalyst to the first compound is 1 to 1.5. Within this range, the reaction efficiency of the first compound is better and the difficulty of purifying the silane coupling agent is less. As an example, the molar ratio of the basic catalyst to the first compound is 1.0, 1.1, 1.2, 1.3, 1.4, or 1.5.

[0086] In some embodiments, the reaction temperature of the nucleophilic substitution reaction is 10° C. to 50° C. For example, the reaction temperature is 10° C., 20° C., 30° C., 40° C., or 50° C.

[0087] In some embodiments, after the nucleophilic substitution reaction is completed, a reaction solution containing a silane coupling agent is obtained. The method for preparing the silane coupling agent further includes purifying the reaction solution to extract the silane coupling agent from the reaction solution.

[0088] In some embodiments, the purification process includes filtering to remove by-products in the reaction solution, collecting the resulting filtrate, and then distilling and purifying to obtain the silane coupling agent. In the case where an alkaline catalyst is also added during the reaction, the alkaline catalyst is also removed by filtration. As an example, a poor solvent for the alkaline catalyst (i.e., a solvent in which the alkaline catalyst is insoluble) is added to the reaction solution to precipitate the alkaline catalyst, and then the precipitated alkaline catalyst is removed by filtration.

[0089] According to the third aspect of the embodiment of the present application, the embodiment of the present application provides a resin composition, which includes a silane coupling agent and a resin, and the silane coupling agent is at least one of the silane coupling agent as described above and the silane coupling agent prepared by the preparation method of the silane coupling agent as described above.

[0090] According to the third aspect of the present application, a resin composition is provided, which includes the above-mentioned silane coupling agent. The resin composition has all the beneficial effects of the above-mentioned silane coupling agent, which will not be described in detail in this application.

[0091] In some embodiments, the mass ratio of the silane coupling agent to the resin is 0.001 to 0.1. Generally, in a resin composition, the mass ratio of the silane coupling agent to the resin should not be too small. Otherwise, when the resin composition is applied to the surface of the substrate, the coverage of the silane coupling agent on the substrate surface is low, and the adhesion promoting effect cannot be achieved. However, the mass ratio of the silane coupling agent to the resin should not be too large, otherwise it may impair the stability and mechanical properties of the resin composition. As an example, the mass ratio of the silane coupling agent to the resin is 0.001, 0.005, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, or 0.1.

[0092] In some embodiments, the mass ratio of the silane coupling agent to the resin is 0.01 to 0.05. Within this range, the resin composition has good bonding effect, mechanical properties, and stability. Alternatively, the mass ratio of the silane coupling agent to the resin is 0.01 to 0.03.

[0093] In some embodiments, the resin composition is a photosensitive resin composition, further comprising a photoinitiator. When the resin composition further comprises a photoinitiator, the resin composition is a photosensitive resin composition. Optionally, the photoinitiator comprises an oxime ester photoinitiator, such as OXE-1. During use of the photosensitive resin composition, the resin can further polymerize under the action of the photoinitiator under illumination.

[0094] In some embodiments, the photosensitive resin composition further comprises at least one of a crosslinking agent and a first solvent. Optionally, the crosslinking agent comprises trimethylolpropane triacrylate. Optionally, the first solvent comprises N-methylpyrrolidone.

[0095] In some embodiments, the resin is an alkali-soluble resin. An alkali-soluble resin is a polymer material having specific alkali-soluble groups. This type of resin can be applied to a photosensitive resin composition and has good developability and pattern forming properties.

[0096] In some embodiments, the alkali-soluble resin includes at least one of a polyimide resin, a polyamic acid resin, a polyamic acid ester resin, and a polybenzoxazole resin.

[0097] According to a fourth aspect of the embodiments of the present application, the embodiments of the present application provide a cured film, which comprises a cured product of the resin composition as described above.

[0098] The cured film includes a cured product of the resin composition. The cured film has all the beneficial effects of the resin composition, which will not be described in detail in this application.

[0099] In some embodiments, the cured film includes at least one of a surface protection film for a semiconductor package element, an interlayer insulating film, a redistribution insulating film, a metal bump stress buffer, and a passivation film. As examples, the cured film is a surface protection film for a semiconductor package element; or the cured film is an interlayer insulating film for a semiconductor package element; or the cured film is a redistribution insulating film for a semiconductor package element; or the cured film is a metal bump stress buffer for a semiconductor package element; or the cured film is a passivation film for a semiconductor package element.

[0100] According to a fifth aspect of the embodiments of the present application, the embodiments of the present application provide a semiconductor device, which includes the cured film as described above.

[0101] In some embodiments, a semiconductor device includes a semiconductor package component including a cured film.

[0102] The following describes the method in conjunction with specific embodiments.

[0103] Example 1

[0104] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0105] .

[0106] The preparation method of the silane coupling agent comprises:

[0107] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 6.18 g (0.04 mol, CAS 36258-82-9) of 4-chloro-3H-[1,2,3]triazolo[4,5-c]pyridine and 6.63 g (0.048 mol) of potassium carbonate and 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropylmethyldimethoxysilane (0.04 mol, CAS 31001-77-1) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature, the 3-mercaptopropylmethyldimethoxysilane solution was slowly added dropwise to the flask while stirring. After the addition was complete, the reaction was continued for 18 hours.

[0108] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the solution is concentrated by rotary evaporation in a 35°C water bath to remove the ethyl acetate. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A1 containing a benzotriazole group is obtained at a concentration of 10.4% (calculated from the integral ratio of the solvent to the silane coupling agent A1 in the H-NMR spectrum).

[0109] The nuclear magnetic resonance information of silane coupling agent A1 is as follows: 1H NMR (CDCl3): δ=0.15(s, 3H), 0.61(m, 2H),1.65(m, 2H), 3.10(m, 2H), 3.55(s, 6H), 7.50(d, 1H), 8.31(d, 1H).

[0110] Example 2

[0111] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0112] .

[0113] The preparation method of the silane coupling agent comprises:

[0114] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 6.18 g (0.04 mol, CAS No. 120641-09-0) of 6-chloro-3H-[1,2,3]triazolo[4,5-c]pyridine and 6.63 g (0.048 mol) of potassium carbonate and 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropylmethyldimethoxysilane (0.04 mol, CAS No. 31001-77-1) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature, the 3-mercaptopropylmethyldimethoxysilane solution was slowly added dropwise to the flask while stirring. After the addition was complete, the reaction was continued for 18 hours.

[0115] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the solution is concentrated by rotary evaporation in a 35°C water bath to remove the ethyl acetate. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A2 containing a benzotriazole group is obtained at a concentration of 10.5% (calculated from the integral ratio of the solvent to the silane coupling agent A2 in the H-NMR spectrum).

[0116] The nuclear magnetic information of silane coupling agent A2 is as follows: 1H NMR (CDCl3): δ=0.15(s, 3H), 0.61(m, 2H), 1.65(m, 2H), 3.08(m, 2H), 3.55(s, 6H), 7.29(s, 1H), 8.48(s, 1H).

[0117] Example 3

[0118] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0119] .

[0120] The preparation method of the silane coupling agent comprises:

[0121] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 6.18 g (0.04 mol, CAS No. 120641-09-0) of 6-chloro-3H-[1,2,3]triazolo[4,5-c]pyridine and 6.63 g (0.048 mol) of potassium carbonate in 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropyltrimethoxysilane (0.04 mol, CAS No. 4420-74-0) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature, the 3-mercaptopropyltrimethoxysilane solution was slowly added dropwise to the flask while stirring. The reaction was continued for 18 hours after the addition was complete.

[0122] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the ethyl acetate is removed by rotary evaporation in a 35°C water bath. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A3 containing a benzotriazole group is obtained at a concentration of 10.2% (calculated from the integral ratio of the solvent to the silane coupling agent A3 in the H-NMR spectrum).

[0123] The nuclear magnetic resonance information of silane coupling agent A3 is as follows: 1H NMR (CDCl3): δ=0.58(m, 2H), 1.65(m, 2H), 3.08(m, 2H), 3.57(s, 9H), 7.29(s, 1H), 8.48(s, 1H).

[0124] Example 4

[0125] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0126] .

[0127] The preparation method of the silane coupling agent comprises:

[0128] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 5.48 g (0.04 mol, CAS No. 18225-90-6) of 5-fluoro-1H-benzotriazole and 6.63 g (0.048 mol) of potassium carbonate and 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropylmethyldimethoxysilane (0.04 mol, CAS No. 31001-77-1) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature (20-30°C), the 3-mercaptopropylmethyldimethoxysilane solution was slowly added dropwise to the flask while stirring. After the addition was complete, the reaction was continued for 18 hours.

[0129] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the ethyl acetate is removed by rotary evaporation in a 35°C water bath. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A4 containing a benzotriazole group is obtained at a concentration of 10.7% (calculated from the integral ratio of the solvent to the silane coupling agent A4 in the H-NMR spectrum).

[0130] The nuclear magnetic resonance information of silane coupling agent A4 is as follows: 1H NMR (CDCl3): δ=0.15(m, 3H), 0.61(m, 2H),1.65(m, 2H), 2.93(m, 2H), 3.55(s, 6H), 7.37(d, 1H), 7.86(d, 1H), 7.91(s, 1H).

[0131] Example 5

[0132] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0133] .

[0134] The preparation method of the silane coupling agent comprises:

[0135] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 5.48 g (0.04 mol, CAS No. 243464-29-1) of 7-fluoro-1H-benzotriazole and 6.63 g (0.048 mol) of potassium carbonate and 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropylmethyldimethoxysilane (0.04 mol, CAS No. 31001-77-1) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature (20-30°C), the 3-mercaptopropylmethyldimethoxysilane solution was slowly added dropwise to the flask while stirring. After the addition was complete, the reaction was continued for 18 hours.

[0136] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the solution is concentrated by rotary evaporation in a 35°C water bath to remove the ethyl acetate. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A5 containing a benzotriazole group is obtained at a concentration of 10.9% (calculated from the integral ratio of the solvent to the silane coupling agent A5 in the H-NMR spectrum).

[0137] The nuclear magnetic resonance information of silane coupling agent A5 is as follows: 1H NMR (CDCl3): δ=0.15(m, 3H), 0.61(m, 2H),1.65(m, 2H), 2.93(m, 2H), 3.55(s, 6H), 7.30-7.37(m, 2H), 7.74(d, 1H).

[0138] Example 6

[0139] This embodiment provides a silane coupling agent, the structural formula of the silane coupling agent is as follows:

[0140] .

[0141] The preparation method of the silane coupling agent comprises:

[0142] To a 250 mL three-necked flask equipped with a stirrer and thermometer, add 5.48 g of 7-fluoro-1H-benzotriazole (0.04 mol, Merck, CAS No. 243464-29-1) and 6.63 g of potassium carbonate (0.048 mol, J&K) in 50 mL of anhydrous N-methylpyrrolidone. Stirring was initiated. Meanwhile, 3-mercaptopropyltrimethoxysilane (0.04 mol, CAS No. 4420-74-0) was weighed and dissolved in 50 mL of anhydrous N-methylpyrrolidone. At room temperature (20-30°C), the 3-mercaptopropyltrimethoxysilane solution was slowly added dropwise to the flask while stirring. After the addition was complete, the reaction was continued for 18 hours.

[0143] After the reaction is complete, 60 g of ethyl acetate is slowly added to the reaction system and stirred for 1 hour to fully precipitate the potassium salt. The reaction solution is then filtered through 5 μm and then 0.5 μm filter papers. After filtration, the ethyl acetate is removed by rotary evaporation in a 35°C water bath. After vacuum distillation, the N-methylpyrrolidone of the silane coupling agent A6 containing a benzotriazole group is obtained at a concentration of 10.8% (calculated from the integral ratio of the solvent to the silane coupling agent A6 in the H-NMR spectrum).

[0144] The nuclear magnetic resonance information of silane coupling agent A6 is as follows: 1H NMR (CDCl3): δ=0.56(m, 2H), 1.65(m, 2H),2.94(m, 2H), 3.57(s, 9H), 7.30-7.37(m, 2H), 7.74(d, 1H).

[0145] Synthesis example 1

[0146] Preparation of polyamic acid ester polymer R1:

[0147] To a double-jacketed 500 mL reactor equipped with a stirrer and thermometer, 31.0 g of 4,4'-diphenyl ether dianhydride (ODPA, 0.1 mol) and 120 mL of anhydrous N-methylpyrrolidone were added. The reaction system was placed under nitrogen and the temperature was raised to 40°C. Subsequently, a solution of 2,2'-bis(trifluoromethyl)-4,4'-diaminophenyl ether (33.0 g, 0.09 mol) in anhydrous N-methylpyrrolidone (120 mL) was slowly added dropwise. This solution had been pre-dissolved 8 hours prior. After the addition, the reaction mixture was allowed to react at 40°C for a further 4 hours. Then, 3-aminophenol (2.18 g, 0.02 mol) dissolved in 10 mL of anhydrous N-methylpyrrolidone was added as a capping agent, and the reaction continued at 40°C for 2 hours. Then, N,N-dimethylformamide dimethyl acetal (21.4 g, 0.18 mol) diluted with 50 mL of anhydrous N-methylpyrrolidone was slowly added dropwise. After the addition was complete, the mixture was reacted at 40°C for 3 hours. After the reaction was completed, the solution was poured into 3 L of deionized water, and the polymer solid precipitate was collected by filtration. After washing away the solvent and by-product residues with a large amount of deionized water, the polymer solid was dried in a vacuum dryer at 80°C for 48 hours to obtain polyamic acid ester polymer R1.

[0148] The molecular weight of the polyamic acid ester polymer R1 was determined by gel permeation chromatography. The column model was Waters Styragel HR 4 and the mobile phase was 0.05 mol / L LiCl in N-methylpyrrolidone. The number average molecular weight of the polyamic acid ester polymer R1 was 1.6×10 4 .

[0149] Synthesis example 2

[0150] Preparation of polyamic acid ester polymer R2:

[0151] To a double-jacketed 500 mL reactor equipped with a stirrer and thermometer, 31.0 g of 4,4'-diphenyl ether dianhydride (ODPA, 0.1 mol) and 120 mL of anhydrous N-methylpyrrolidone were added. The reaction system was placed under nitrogen and the temperature was raised to 40°C. Subsequently, a solution of bis(3-amino-4-hydroxyphenyl)sulfone (25.2 g, 0.09 mol) in anhydrous N-methylpyrrolidone (120 mL) was slowly added dropwise. This solution had been pre-dissolved 8 hours prior. After the addition, the reaction mixture was allowed to react at 40°C for a further 4 hours. Then, 3-aminophenol (2.18 g, 0.02 mol) dissolved in 10 mL of anhydrous N-methylpyrrolidone was added as a capping agent, and the reaction continued at 40°C for 2 hours. Then, N,N-dimethylformamide dimethyl acetal (21.4 g, 0.18 mol) diluted with 50 mL of anhydrous N-methylpyrrolidone was slowly added dropwise. After the addition was complete, the mixture was reacted at 40°C for 3 hours. After the reaction was completed, the solution was poured into 3 L of deionized water, and the polymer solid precipitate was collected by filtration. After washing the solvent and by-product residues with a large amount of deionized water, the polymer solid was dried in a vacuum dryer at 80°C for 48 hours to obtain polyamic acid ester polymer R2.

[0152] The molecular weight of the polyamic acid ester polymer R2 was determined by gel permeation chromatography. The column model was Waters Styragel HR 4 and the mobile phase was 0.05 mol / L LiCl in N-methylpyrrolidone. The number average molecular weight of the polyamic acid ester polymer R2 was 1.8×10 4 .

[0153] Application Example 1

[0154] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A1 obtained in Example 1 (i.e., 1.92 g of the solution of the silane coupling agent A1) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0155] Application Example 2

[0156] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A2 obtained in Example 2 (i.e., 1.90 g of the solution of the silane coupling agent A2) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0157] Application Example 3

[0158] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A3 obtained in Example 3 (i.e., 1.96 g of the solution of the silane coupling agent A3) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0159] Application Example 4

[0160] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A4 obtained in Example 4 (i.e., 1.87 g of the solution of the silane coupling agent A4) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0161] Application Example 5

[0162] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A5 obtained in Example 5 (i.e., 1.83 g of the solution of the silane coupling agent A5) and 0.3 g of the photoinitiator OXE-1 (molecular formula C27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0163] Application Example 6

[0164] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A6 obtained in Example 6 (i.e., 1.85 g of the solution of the silane coupling agent A6) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0165] Application Example 7

[0166] 10.0 g of the above-mentioned polyamic acid ester polymer R1 and 31.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.1 g of the silane coupling agent A1 obtained in Example 1 and 0.1 g of the silane coupling agent A2 obtained in Example 2 (i.e., 0.96 g and 0.95 g of the solutions of silane coupling agent A1 and silane coupling agent A2, respectively) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0167] Application Example 8

[0168] 10.0 g of the polyamic acid ester polymer R2 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A1 obtained in Example 1 (i.e., 1.92 g of the solution of the silane coupling agent A1) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0169] Application Example 9

[0170] 10.0 g of the polyamic acid ester polymer R2 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of the silane coupling agent A2 obtained in Example 2 (i.e., 1.90 g of the solution of the silane coupling agent A2) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0171] Application Example 10

[0172] 10.0 g of the polyamic acid ester polymer R1 and 30.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.1 g of the silane coupling agent A2 obtained in Example 2 (i.e., 0.95 g of the solution of the silane coupling agent A2) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0173] Application Example 11

[0174] 10.0 g of the polyamic acid ester polymer R1 and 27.0 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.5 g of the silane coupling agent A2 obtained in Example 2 (i.e., 4.76 g of the solution of the silane coupling agent A2) and 0.3 g of the photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0175] Comparative Example 1

[0176] 10.0 g of the above-mentioned polyamic acid ester polymer R1 and 31.7 g of electronic grade N-methyl pyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of silane coupling agent 3-mercaptopropylmethyldimethoxysilane and 0.3 g of photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0177] Comparative Example 2

[0178] 10.0 g of the above-mentioned polyamic acid ester polymer R1 and 31.70 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.1 g of silane coupling agent 3-mercaptopropylmethyldimethoxysilane and 0.1 g of copper surface additive 3H-1,2,3-triazolo[4,5-C]pyridine, 0.3 g of photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0179] Comparative Example 3

[0180] 10.0 g of the above-mentioned polyamic acid ester polymer R1 and 31.7 g of electronic grade N-methylpyrrolidone were added to a 250 mL three-necked flask and stirred until uniformly dissolved. Subsequently, 0.2 g of copper surface additive 3H-1,2,3-triazolo[4,5-C]pyridine and 0.3 g of photoinitiator OXE-1 (molecular formula C 27 H 27 NO3S, purity ≥98%) and 6.0 g of a cross-linking agent trimethylolpropane triacrylate (abbreviated as TMPTA, purity ≥95%) were fully dissolved and filtered using a 0.5 μm filter membrane to obtain the corresponding photosensitive resin composition.

[0181] The type and amount of the polyamic acid ester polymer and the type and amount of the additives in each application example and comparative example are recorded in Table 1.

[0182] Table 1

[0183]

[0184] The photosensitive resin compositions prepared according to the corresponding examples and comparative examples were subjected to the following tests, and the test results are recorded in Table 3:

[0185] 1. Copper Surface Adhesion Test: The photosensitive resin composition was spin-coated onto an 8-inch silicon wafer that had been sputtered with 0.1μm titanium and 0.4μm copper. The wafer was pre-baked at 105°C on a hot plate for 180 seconds to form a coating approximately 8μm thick. A temperature-programmed curing oven was used to heat the wafer at 250°C for 2 hours under a nitrogen atmosphere to obtain a cured resin film approximately 7μm thick. The coated wafer was then placed in a high-temperature, high-humidity accelerated aging chamber at 130°C and 85% RH for 264 hours. After the accelerated aging test, the adhesion between the cured resin film and the copper surface was evaluated using the crosscut method according to JIS K 5600-5-6. The evaluation criteria are shown in Table 2:

[0186] Table 2

[0187]

[0188] 2. Glue stability test: Visual observation is adopted. If the photosensitive resin composition becomes turbid or has precipitates within 14 days, it is recorded as "white turbidity". If it is still clear and has good fluidity, it is recorded as "normal".

[0189] 3. Copper Surface Adhesion Stability Test: The photosensitive resin composition was placed in air at room temperature for 14 days. The adhesion properties of the cured resin coating to the copper surface were tested and evaluated again according to the copper surface adhesion test method 14 days after opening the bottle. Please refer to Table 2 for the evaluation criteria.

[0190] Table 3

[0191]

[0192] As can be seen from the test results in Table 3, compared to Comparative Examples 1 to 3, the silane coupling agents provided in Examples 1 to 6 of the present application were applied to the photosensitive resin compositions (i.e., Application Examples 1 to 11). Even when the photosensitive resin compositions were cured at a relatively low temperature (250°C), the cured resin coatings formed maintained good adhesion to the copper surface. This demonstrates that the silane coupling agents provided in the examples of the present application can effectively improve the adhesion of the photosensitive resin compositions to the copper surface, and their performance is similar to or even better than that of the copper surface additive provided in the related art (Comparative Example 3). In addition, with the exception of Application Examples 3 and 6, the photosensitive resin compositions of the other application examples were able to cure at a relatively low temperature (250°C) and maintain good adhesion to the copper surface even after 14 days of storage. This demonstrates that the silane coupling agents provided in the examples of the present application, when added to the photosensitive resin compositions, are not likely to affect the storage stability of the photosensitive resin compositions. Abnormal adhesive stability was observed in Application Examples 3 and 6 because the silane coupling agents used in these examples contained an excessive number of alkoxy groups. Compared to the silane coupling agents used in Application Examples 1, 2, 4, and 5, the silane coupling agents used in Application Examples 3 and 6 contained only three methoxy groups. Consequently, when the silane coupling agents in the photosensitive resin compositions were stored in air at room temperature, they were attacked by water in the air, causing hydrolysis, which in turn affected the storage stability of the photosensitive resin compositions.

[0193] However, compared with Application Example 1, Application Example 2, Application Example 4, and Application Example 5, when the number of methoxy groups in the silane coupling agent is the same, the photosensitive resin composition provided in Comparative Example 1 has worse stability and is more likely to become turbid during storage in air. This is because the silane coupling agent used in Comparative Example 1 is 3-mercaptopropylmethyldimethoxysilane, which has less steric hindrance than the silane coupling agents A1, A2, A4, and A5 used in Application Examples 1, 2, 4, and 5. Therefore, the methoxy groups in 3-mercaptopropylmethyldimethoxysilane react more easily with water, thereby reducing the storage stability of the photosensitive resin composition.

[0194] Compared with Application Examples 1, 2, and 4, the stability of the photosensitive resin composition provided in Comparative Example 3 is worse. This is presumably due to the interaction (stacking) between the aromatic rings on the copper surface additive 3H-1,2,3-triazolo[4,5-C]pyridine used in Comparative Example 3, resulting in poor solubility and precipitation after static storage. Although the silane coupling agents A1, A2, A4, and A5 used in Application Examples 1, 2, 4, and 5 also contain aromatic rings, the increased steric hindrance prevents the aromatic rings on silane coupling agents A1, A2, A4, and A5 from interacting with each other, thereby improving the stability of the photosensitive resin composition.

[0195] It can be understood that the photosensitive resin composition in Comparative Example 2 contains both 3-mercaptopropylmethyldimethoxysilane and 3H-1,2,3-triazolo[4,5-C]pyridine, and the storage stability of the photosensitive resin composition is also poor.

[0196] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, "plurality" means two or more, unless otherwise specifically defined.

[0197] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0198] The embodiments, implementation methods and related technical features of the present application can be combined and replaced with each other without conflict.

[0199] The above are merely preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. A silane coupling agent, characterized in that The structural formula of the silane coupling agent is shown in formula (I): Formula (I), In formula (I), X1 and X2 are each independently selected from a nitrogen atom and a carbon atom; Y is an oxygen atom and a sulfur atom; R1 is an alkyl group having 1 to 10 carbon atoms; R2, R3 and R4 are each independently selected from an alkyl group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms, and the number of the alkoxy groups based on R2, R3 and R4 is greater than or equal to 1.

2. The silane coupling agent according to claim 1, characterized in that wherein one of X1 and X2 is a nitrogen atom.

3. The silane coupling agent according to claim 1, characterized in that Y is a sulfur atom.

4. The silane coupling agent according to claim 1, characterized in that R1 is a saturated alkyl group having 1 to 4 carbon atoms.

5. The silane coupling agent according to any one of claims 2 to 4, characterized in that R1 is a straight-chain saturated alkyl group having 2 to 3 carbon atoms.

6. The silane coupling agent according to any one of claims 1 to 4, characterized in that R2, R3 and R4 are each independently selected from any one of an alkyl group having 1 to 2 carbon atoms and an alkoxy group having 1 to 2 carbon atoms.

7. The silane coupling agent according to claim 6, characterized in that The number of the alkoxy groups is greater than or equal to 1 and less than or equal to 2 based on R2, R3, and R4.

8. The silane coupling agent according to claim 6, characterized in that The number of the alkoxy groups is greater than the number of the alkyl groups based on R2, R3 and R4.

9. The silane coupling agent according to claim 8, characterized in that R2, R3 and R4 are each independently selected from any one of methyl, ethyl, methoxy and ethoxy groups, and the number of the methyl groups is 0 or 1, and the number of the ethyl groups is 0 or 1 based on R2, R3 and R4.

10. A method for preparing a silane coupling agent, for preparing the silane coupling agent according to claim 1, characterized in that: include: The silane coupling agent is obtained by performing a nucleophilic substitution reaction between the first compound and the second compound, wherein the structural formula of the first compound is shown in formula (II): Formula (II), In formula (II), Z is any one of a hydroxyl group and a thiol group, and R1, R2, R3 and R4 are the same as those in formula (I); The structural formula of the second compound is shown in formula (III): Formula (III), In formula (III), W is a halogen atom that replaces at least one hydrogen atom on the aromatic ring, and X1 and X2 are the same as those in formula (I).

11. The method for preparing a silane coupling agent according to claim 10, wherein: The first compound and the second compound undergo the nucleophilic substitution reaction in a polar solvent.

12. The method for preparing a silane coupling agent according to claim 11, wherein: The polar solvent is a polar aprotic solvent; the polar aprotic solvent includes at least one of N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and N,N-diethylformamide.

13. The method for preparing a silane coupling agent according to claim 10, wherein: The first compound and the second compound undergo the nucleophilic substitution reaction under the catalysis of a basic catalyst.

14. The method for preparing a silane coupling agent according to claim 13, wherein: The basic catalyst includes at least one of an organic base and an inorganic base.

15. The method for preparing a silane coupling agent according to claim 14, wherein: The organic base includes triethylamine, pyridine, sodium methoxide, sodium ethoxide, and N,N - at least one of diisopropylethylamine.

16. The method for preparing a silane coupling agent according to claim 14, wherein: The inorganic base includes at least one of sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide and potassium hydroxide.

17. The method for preparing a silane coupling agent according to claim 13, wherein: The molar ratio of the basic catalyst to the first compound is 1-10.

18. The method for preparing a silane coupling agent according to claim 13, wherein: The molar ratio of the basic catalyst to the first compound is 1 to 1.

5.

19. The method for preparing a silane coupling agent according to any one of claims 10 to 18, characterized in that: The reaction temperature of the nucleophilic substitution reaction is 10°C to 50°C.

20. The method for preparing a silane coupling agent according to any one of claims 10 to 18, characterized in that: W is a fluorine atom or a chlorine atom, and the number of substitution is 1.

21. The method for preparing a silane coupling agent according to any one of claims 10 to 18, characterized in that: The molar ratio of the first compound to the second compound is 1:

1.

22. The method for preparing a silane coupling agent according to any one of claims 10 to 18, characterized in that: After the nucleophilic substitution reaction is completed, a reaction liquid containing the silane coupling agent is obtained. The preparation method of the silane coupling agent further includes purifying the reaction liquid to extract the silane coupling agent from the reaction liquid.

23. A resin composition, characterized in that The invention comprises a silane coupling agent and a resin, wherein the silane coupling agent is at least one of the silane coupling agent according to any one of claims 1 to 9 and the silane coupling agent prepared by the preparation method of the silane coupling agent according to any one of claims 10 to 22.

24. The resin composition according to claim 23, characterized in that The mass ratio of the silane coupling agent to the resin is 0.001-0.

1.

25. The resin composition according to claim 23, characterized in that The resin composition is a photosensitive resin composition, and the photosensitive resin composition further comprises at least one of a photoinitiator, a crosslinking agent, and a first solvent.

26. The resin composition according to any one of claims 23 to 25, characterized in that The resin is an alkali-soluble resin; the alkali-soluble resin includes at least one of polyimide resin, polyamic acid resin, polyamic acid ester resin and polybenzoxazole resin.

27. A cured film, characterized in that The cured film comprises a cured product of the resin composition according to any one of claims 23 to 26.

28. The cured film according to claim 27, wherein The cured film includes at least one of a surface protection film, an interlayer insulating film, an insulating film for redistribution, a metal bump stress buffer layer, and a passivation film for a semiconductor package element.

29. A semiconductor device, characterized in that The semiconductor device includes the cured film according to claim 27 or 28.

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