Curing agent, semiconductor bonding composition containing the same, semiconductor bonding film, and semiconductor package using the same

Abstract

The present invention relates to a curing agent, a semiconductor adhesive composition containing the curing agent, which exhibits excellent adhesive strength while suppressing the occurrence of cracks and has excellent reliability, a semiconductor adhesive film, and a semiconductor package using the same.

Description

[Technical field]

[0001] This specification claims the benefit of the filing date of Korean Patent Application No. 10-2020-0050164, filed with the Korean Intellectual Property Office on April 24, 2020, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a curing agent, a semiconductor bonding composition containing the same, a semiconductor bonding film, and a semiconductor package using the same. [Background technology]

[0003] Recently, with the growing trend for electronic devices to become smaller, more functional, and larger in capacity, the need for higher density and integration of semiconductor packages has increased dramatically. As a result, the size of semiconductor chips has become larger and larger. In order to improve integration, stack packaging methods in which chips are stacked in multiple layers are gradually becoming more common.

[0004] Bonding between chips using through silicon vias is performed by thermal compression bonding, which applies pressure at a temperature of 200 to 300 degrees Celsius for 2 to 10 seconds. Paste-type non-conductive paste (NCP) or non-conductive film (NCF) is used as an adhesive to fill between each TSV layer, and fillers are dispersed in epoxy or bismaleimide resin to ensure thermal expansion coefficient and rigidity and prevent cracks. However, these adhesives are vulnerable to sudden changes in temperature and pressure during the thermocompression bonding process, and the filler separates from the resin, forming areas in the resin where there is no filler, which causes cracks in the semiconductor package. In particular, existing adhesives use BPA-based hardeners as hardeners, but the BPA hardeners have a problem of being vulnerable to cracks.

[0005] Therefore, there is a current need for a technology for a semiconductor bonding composition that is highly reliable and prevents cracks from occurring even when subjected to rapid pressure and temperature changes during the thermocompression bonding process. Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention provides a curing agent that exhibits excellent adhesive strength while suppressing the occurrence of cracks, a semiconductor bonding composition containing the curing agent, a semiconductor bonding film, and a semiconductor package using the same.

[0007] However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not mentioned will be clearly understood by those skilled in the art from the following description. [Means for solving the problem]

[0008] One embodiment of the present invention provides a curing agent comprising at least one of a compound represented by the following formula 1 and a compound represented by the following formula 2: [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, R1, R2, R3 and R4 are each independently a phenolic compound; n is an integer from 1 to 50, and k is an integer from 1 to 50.

[0009] One embodiment of the present invention provides a semiconductor bonding composition comprising: a thermosetting resin; a thermoplastic resin; and a curing agent comprising at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, R1, R2, R3 and R4 are each independently a phenolic compound; n is an integer of 1 to 50; and k is an integer of 1 to 50.

[0010] One embodiment of the present invention provides a semiconductor adhesive film comprising a cured product of the semiconductor adhesive composition.

[0011] One embodiment of the present invention provides a semiconductor package comprising the semiconductor adhesive film. Effect of the Invention

[0012] By using the curing agent according to one embodiment of the present invention, it is possible to realize an adhesive composition that exhibits excellent adhesive strength while suppressing the occurrence of cracks.

[0013] The semiconductor bonding composition according to one embodiment of the present invention exhibits excellent adhesive strength while suppressing the occurrence of cracks.

[0014] The semiconductor adhesive film according to one embodiment of the present invention has excellent adhesive strength, and can effectively prevent cracks from occurring during the thermocompression bonding process.

[0015] A semiconductor package according to an embodiment of the present invention can be excellent in quality.

[0016] The effects of the present invention are not limited to those described above, and effects not mentioned will be clearly understood by those skilled in the art from the present specification and the accompanying drawings. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] Throughout this specification, when a part is described as "comprising" a certain element, this means that it can further include other elements, but not to the exclusion of other elements, unless specifically stated to the contrary.

[0018] Throughout this specification, when an element is said to be "on" another element, this includes not only when the element is in contact with the other element, but also when there is another element between the two elements.

[0019] Throughout this specification, the unit "parts by weight" can refer to the weight ratio between each component.

[0020] The present specification will be explained in further detail below. One embodiment of the present invention provides a curing agent comprising at least one of a compound represented by the following formula 1 and a compound represented by the following formula 2: [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, R1, R2, R3 and R4 are each independently a phenolic compound; n is an integer of 1 to 50; and k is an integer of 1 to 50.

[0021] By using the curing agent according to one embodiment of the present invention, it is possible to realize an adhesive composition that exhibits excellent adhesive strength while suppressing the occurrence of cracks.

[0022] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 is capped at the end with R1 and R2. R1 and R2 may each be independently a phenolic compound. When R1 and R2 are each independently a phenolic compound, the hardness of the curing agent itself can be reduced. As a result, the softness of the cured product of the adhesive composition containing the curing agent is increased, and an adhesive film having excellent adhesive performance and excellent crack resistance in which crack generation is suppressed can be realized. In addition, the improved crack resistance of the adhesive film can also show excellent performance in reliability.

[0023] In addition, R1 and R2 may be the same. That is, the same phenolic compound may be bonded to both ends of the compound represented by the formula 1, and the dispersibility of the compound represented by the formula 1 may be improved.

[0024] According to one embodiment of the present invention, in the above Chemical Formula 1, n may be an integer of 1 to 50, specifically an integer of 1 to 45, an integer of 5 to 40, an integer of 10 to 35, an integer of 15 to 30, an integer of 20 to 25, an integer of 1 to 20, an integer of 2 to 15, an integer of 3 to 10, an integer of 4 to 7, an integer of 15 to 40, an integer of 20 to 35, an integer of 25 to 30, an integer of 30 to 50, or an integer of 35 to 45. When n is within the above-mentioned range in the above Chemical Formula 1, the compound represented by the above Chemical Formula 1 may have excellent curing performance.

[0025] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 can include at least one of the compounds represented by the following Chemical Formulas 1-1 to 1-4. [ka] [ka] [ka] [ka]

[0026] Specifically, the compound represented by Chemical Formula 1 may be the compound represented by Chemical Formula 1-1. The compound having the structure represented by Chemical Formula 1-1 has excellent curing performance and can effectively reduce the hardness of the cured product of the adhesive composition containing the curing agent.

[0027] According to one embodiment of the present invention, the compound represented by the chemical formula 2 is capped at the end with R3 and R4. R3 and R4 may each be independently a phenolic compound. When R3 and R4 are each independently a phenolic compound, the hardness of the curing agent itself can be reduced, and the softness of the cured product of the adhesive composition containing the curing agent can be increased. As a result, the adhesive composition can provide an adhesive film having excellent adhesive performance and crack resistance.

[0028] In addition, R3 and R4 may be the same as each other. That is, the same phenolic compound may be bonded to both ends of the compound represented by the formula 2, and the dispersibility of the compound represented by the formula 2 may be improved.

[0029] According to one embodiment of the present invention, in the above Chemical Formula 2, k may be an integer of 1 to 50, specifically an integer of 1 to 45, an integer of 5 to 40, an integer of 10 to 35, an integer of 15 to 30, an integer of 20 to 25, an integer of 1 to 20, an integer of 2 to 15, an integer of 3 to 10, an integer of 4 to 7, an integer of 15 to 40, an integer of 20 to 35, an integer of 25 to 30, an integer of 30 to 50, or an integer of 35 to 45. When k is within the above-mentioned range in the above Chemical Formula 2, the compound represented by the above Chemical Formula 2 may have excellent curing performance.

[0030] According to one embodiment of the present invention, the compound represented by Chemical Formula 2 can include at least one of the compounds represented by the following Chemical Formulas 2-1 to 2-4. [ka] [ka] [ka] [ka] In the above chemical formula, R3 and R4 are each independently a phenolic compound, and k is an integer of 1 to 50.

[0031] Specifically, the compound represented by Chemical Formula 2 may be the compound represented by Chemical Formula 2-1. The compound having the structure represented by Chemical Formula 2-1 has excellent curing performance and can effectively reduce the hardness of the cured product of the adhesive composition containing the curing agent.

[0032] According to one embodiment of the present invention, the curing agent can include at least the compound represented by the formula 2-1. As described above, the compound having the structure represented by the formula 2-1 has excellent curing performance, and can effectively reduce the hardness of the cured product of the adhesive composition, and can effectively improve the crack resistance and reliability of the adhesive film.

[0033] According to one embodiment of the present invention, the curing agent may include at least the compound represented by Chemical Formula 1-1 and the compound represented by Chemical Formula 2-1. As described above, the compound represented by Chemical Formula 1-1 and the compound represented by Chemical Formula 2-1 have excellent curing performance and can effectively reduce the hardness of the cured product of the adhesive composition containing the curing agent.

[0034] According to one embodiment of the present invention, the phenolic compound may be a monocyclic compound. That is, R1, R2, R3, and R4 may each independently be a monocyclic phenolic compound. When R1, R2, R3, and R4 are each independently a monocyclic phenolic compound, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. That is, the adhesive composition containing the curing agent has excellent adhesive strength and can effectively suppress cracks that may occur during thermocompression bonding.

[0035] According to one embodiment of the present invention, the phenolic compound may be a phenol group that is unsubstituted or substituted with at least one of a linear or branched alkyl group having 1 to 10 carbon atoms and an alicyclic alkyl group having 4 to 10 carbon atoms. Specifically, the phenolic compound may be an unsubstituted phenol group. Alternatively, the phenolic compound may be a phenol group that is substituted with one or more alkyl groups. Specifically, the phenolic compound may be a phenol group that is substituted with at least one of a linear or branched aliphatic alkyl group and an alicyclic alkyl group.

[0036] By binding the above-mentioned types of phenolic compounds to the terminals of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can exhibit excellent curing performance while having appropriate flexibility.

[0037] According to one embodiment of the present invention, the number of carbon atoms of the linear or branched alkyl group substituted on the phenol group may be 1-10, 1-8, 1-6, 1-5, 1-4, 1-3, 1-2, 2-4, 3-5, or 4-6. When the number of carbon atoms of the linear or branched alkyl group is within the above-mentioned range, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. The linear or branched alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, or 2-ethylbutyl, but the type of the alkyl group is not limited thereto.

[0038] According to one embodiment of the present invention, the carbon number of the alicyclic alkyl group substituted with the phenol group may be 4 to 10, 4 to 8, 5 to 8, or 6 to 8. When the carbon number of the alicyclic alkyl group is within the above-mentioned range, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. The alicyclic alkyl group may be cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, but the type of the alkyl group is not limited thereto.

[0039] According to one embodiment of the present invention, the number of the alkyl groups substituted on the phenol group may be from 1 to 3, or from 1 to 2. When the number of the alkyl groups substituted on the phenol group is within the above-mentioned range, the curing performance of the curing agent can be prevented from decreasing and the flexibility of the curing agent can be effectively increased.

[0040] According to one embodiment of the invention, the phenolic compound may be any one of the following compounds: [ka]

[0041] Specifically, the phenolic compound may be any one of the following compounds: [ka] In the above compounds, "*" denotes the point of attachment.

[0042] When the phenol-based compound is the above compound, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can effectively reduce hardness while maintaining excellent curing performance. Therefore, the adhesive composition containing the curing agent can provide an adhesive film having excellent adhesive performance and crack resistance.

[0043] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may include at least one of a compound represented by Chemical Formula 1-A and a compound represented by Chemical Formula 1-B. [ka] [ka] In the above chemical formula, n is an integer of 1-50.

[0044] The compound represented by Chemical Formula 1-A and the compound represented by Chemical Formula 1-B can effectively reduce hardness and improve the crack resistance of the bonding composition including the curing agent, and can have a curing performance capable of realizing excellent mechanical properties.

[0045] According to one embodiment of the present invention, the compound represented by the chemical formula 1-A may include the following compound 1-A-1, and the compound represented by the chemical formula 1-B may include the following compound 1-B-1. [ka] [ka] In the above compound, n is an integer of 1-50.

[0046] According to one embodiment of the present invention, the compound represented by Chemical Formula 2 may include at least one of a compound represented by Chemical Formula 2-A and a compound represented by Chemical Formula 2-B. [ka] [ka] In the above chemical formula, k is an integer of 1 to 50.

[0047] The adhesive composition containing the compound represented by Chemical Formula 2-A and the compound represented by Chemical Formula 2-B can realize an adhesive film having excellent adhesive performance and crack resistance.

[0048] According to one embodiment of the present invention, the compound represented by the chemical formula 2-A may include the following compound 2-A-1, and the compound represented by the chemical formula 2-B may include the following compound 2-B-1. [ka] [ka] In the above compound, n is an integer of 1-50.

[0049] One embodiment of the present invention provides a semiconductor bonding composition comprising: a thermosetting resin; a thermoplastic resin; and a curing agent comprising at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, R1, R2, R3 and R4 are each independently a phenolic compound; n is an integer of 1 to 50; and k is an integer of 1 to 50.

[0050] The semiconductor bonding composition according to one embodiment of the present invention exhibits excellent adhesive strength while suppressing the occurrence of cracks. Specifically, the semiconductor bonding composition according to one embodiment of the present invention contains a curing agent containing at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, and thus has excellent adhesive strength while effectively suppressing cracks that may occur during thermocompression bonding.

[0051] According to one embodiment of the present invention, the compound represented by the chemical formula 1 is capped at the end with R1 and R2. R1 and R2 may each be independently a phenolic compound. When R1 and R2 are each independently a phenolic compound, the hardness of the curing agent itself can be reduced. As a result, the softness of the cured product of the semiconductor bonding composition containing the curing agent is increased, and an adhesive film having excellent adhesive performance and excellent crack resistance in which crack generation is suppressed can be realized. By improving the crack resistance of the adhesive film, it can also exhibit excellent performance in reliability.

[0052] In addition, R1 and R2 may be the same. That is, the same phenolic compound may be bonded to both ends of the compound represented by the formula 1, and the dispersibility of the compound represented by the formula 1 may be improved.

[0053] According to one embodiment of the present invention, in the above Chemical Formula 1, n may be an integer of 1 to 50, specifically an integer of 1 to 45, an integer of 5 to 40, an integer of 10 to 35, an integer of 15 to 30, an integer of 20 to 25, an integer of 1 to 20, an integer of 2 to 15, an integer of 3 to 10, an integer of 4 to 7, an integer of 15 to 40, an integer of 20 to 35, an integer of 25 to 30, an integer of 30 to 50, or an integer of 35 to 45. When n is within the above-mentioned range in the above Chemical Formula 1, the compound represented by the above Chemical Formula 1 may have excellent curing performance.

[0054] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 can include at least one of the compounds represented by the following Chemical Formulas 1-1 to 1-4. [ka] [ka] [ka] [ka]

[0055] Specifically, the compound represented by Chemical Formula 1 may be the compound represented by Chemical Formula 1-1. The compound having the structure represented by Chemical Formula 1-1 has excellent curing performance and can effectively reduce the hardness of the cured product of the semiconductor bonding composition.

[0056] According to one embodiment of the present invention, the compound represented by the chemical formula 2 is capped at the end with R3 and R4. R3 and R4 may each be independently a phenolic compound. When R3 and R4 are each independently a phenolic compound, the hardness of the curing agent itself can be reduced, and the softness of the cured product of the semiconductor bonding composition containing the curing agent can be increased. As a result, the semiconductor bonding composition can provide an adhesive film having excellent adhesive performance and crack resistance.

[0057] In addition, R3 and R4 may be the same as each other. That is, the same phenolic compound may be bonded to both ends of the compound represented by the formula 2, and the dispersibility of the compound represented by the formula 2 may be improved.

[0058] According to one embodiment of the present invention, in the above Chemical Formula 2, k may be an integer of 1 to 50, specifically an integer of 1 to 45, an integer of 5 to 40, an integer of 10 to 35, an integer of 15 to 30, an integer of 20 to 25, an integer of 1 to 20, an integer of 2 to 15, an integer of 3 to 10, an integer of 4 to 7, an integer of 15 to 40, an integer of 20 to 35, an integer of 25 to 30, an integer of 30 to 50, or an integer of 35 to 45. When k is within the above-mentioned range in the above Chemical Formula 2, the compound represented by the above Chemical Formula 2 may have excellent curing performance.

[0059] According to one embodiment of the present invention, the compound represented by Chemical Formula 2 can include at least one of the compounds represented by the following Chemical Formulas 2-1 to 2-4. [ka] [ka] [ka] [ka]

[0060] Specifically, the compound represented by Chemical Formula 2 may be the compound represented by Chemical Formula 2-1. The compound having the structure represented by Chemical Formula 2-1 has excellent curing performance and can effectively reduce the hardness of the cured product of the semiconductor bonding composition.

[0061] According to one embodiment of the present invention, the curing agent can include at least the compound represented by the formula 2-1. As described above, the compound having the structure represented by the formula 2-1 has excellent curing performance, and can effectively reduce the hardness of the cured product of the semiconductor bonding composition, and can effectively improve the crack resistance and reliability of the adhesive film.

[0062] According to one embodiment of the present invention, the curing agent can include at least the compound represented by Chemical Formula 1-1 and the compound represented by Chemical Formula 2-1. As described above, the compound represented by Chemical Formula 1-1 and the compound represented by Chemical Formula 2-1 have excellent curing performance and can effectively reduce the hardness of the cured product of the semiconductor bonding composition.

[0063] According to one embodiment of the present invention, the phenolic compound may be a monocyclic compound. That is, R1, R2, R3, and R4 may each independently be a monocyclic phenolic compound. When R1, R2, R3, and R4 are each independently a monocyclic phenolic compound, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. That is, the semiconductor bonding composition containing the curing agent has excellent adhesive strength and can effectively suppress cracks that may occur during thermocompression bonding.

[0064] According to one embodiment of the present invention, the phenolic compound may be a phenol group that is unsubstituted or substituted with at least one of a linear or branched alkyl group having 1 to 10 carbon atoms and an alicyclic alkyl group having 4 to 10 carbon atoms. Specifically, the phenolic compound may be an unsubstituted phenol group. Alternatively, the phenolic compound may be a phenol group that is substituted with one or more alkyl groups. Specifically, the phenolic compound may be a phenol group that is substituted with at least one of a linear or branched aliphatic alkyl group and an alicyclic alkyl group.

[0065] By binding the above-mentioned types of phenolic compounds to the terminals of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can exhibit excellent curing performance while having appropriate flexibility.

[0066] According to one embodiment of the present invention, the number of carbon atoms of the linear or branched alkyl group substituted on the phenol group may be 1-10, 1-8, 1-6, 1-5, 1-4, 1-3, 1-2, 2-4, 3-5, or 4-6. When the number of carbon atoms of the linear or branched alkyl group is within the above-mentioned range, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. The linear or branched alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, or 2-ethylbutyl, but the type of the alkyl group is not limited thereto.

[0067] According to one embodiment of the present invention, the carbon number of the alicyclic alkyl group substituted with the phenol group may be 4 to 10, 4 to 8, 5 to 8, or 6 to 8. When the carbon number of the alicyclic alkyl group is within the above-mentioned range, the hardness of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be effectively reduced. The alicyclic alkyl group may be cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, but the type of the alkyl group is not limited thereto.

[0068] According to one embodiment of the present invention, the number of the alkyl groups substituted on the phenol group may be from 1 to 3, or from 1 to 2. When the number of the alkyl groups substituted on the phenol group is within the above-mentioned range, the curing performance of the curing agent can be prevented from decreasing and the flexibility of the curing agent can be effectively increased.

[0069] According to one embodiment of the invention, the phenolic compound may be any one of the following compounds: [ka]

[0070] Specifically, the phenolic compound may be any one of the following compounds: [ka] In the above compounds, "*" denotes the point of attachment.

[0071] When the phenol-based compound is the above compound, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can effectively reduce hardness while maintaining excellent curing performance. As a result, the semiconductor bonding composition containing the curing agent can provide a semiconductor bonding film having excellent adhesive performance and crack resistance.

[0072] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may include at least one of a compound represented by Chemical Formula 1-A and a compound represented by Chemical Formula 1-B. [ka] [ka] In the above chemical formula, n is an integer of 1-50.

[0073] The compound represented by Chemical Formula 1-A and the compound represented by Chemical Formula 1-B can effectively reduce hardness and improve the crack resistance of the semiconductor bonding composition, and can have a curing performance capable of realizing excellent mechanical properties.

[0074] According to one embodiment of the present invention, the compound represented by the chemical formula 1-A may include the following compound 1-A-1, and the compound represented by the chemical formula 1-B may include the following compound 1-B-1. [ka] [ka] In the above compound, n is an integer of 1-50.

[0075] According to one embodiment of the present invention, the compound represented by Chemical Formula 2 may include at least one of a compound represented by Chemical Formula 2-A and a compound represented by Chemical Formula 2-B. [ka] [ka] In the above chemical formula, k is an integer of 1 to 50.

[0076] The semiconductor adhesive composition containing the compound represented by the chemical formula 2-A and the compound represented by the chemical formula 2-B can realize a semiconductor adhesive film having excellent adhesive performance and crack resistance.

[0077] According to one embodiment of the present invention, the compound represented by the chemical formula 2-A may include the following compound 2-A-1, and the compound represented by the chemical formula 2-B may include the following compound 2-B-1. [ka] [ka] In the above compound, n is an integer of 1-50.

[0078] According to one embodiment of the present invention, the content of the curing agent may be 5 parts by weight or more and 195 parts by weight or less with respect to 100 parts by weight of the thermosetting resin. Specifically, the content of the curing agent with respect to 100 parts by weight of the thermosetting resin may be 5 parts by weight or more and 190 parts by weight or less, 10 parts by weight or more and 150 parts by weight or less, 20 parts by weight or more and 130 parts by weight or less, 30 parts by weight or more and 110 parts by weight or less, 40 parts by weight or more and 100 parts by weight or less, 50 parts by weight or more and 80 parts by weight or less, 5 parts by weight or more and 100 parts by weight or less, 5 parts by weight or more and 95 parts by weight or less, 5 parts by weight or more and 85 parts by weight or less, 5 parts by weight or more and 80 parts by weight or less, 5 parts by weight or more and 75 parts by weight or less. or more than 190 parts by weight, 5 parts by weight or more and 70 parts by weight or less, 5 parts by weight or more and 50 parts by weight or less, 5 parts by weight or more and 25 parts by weight or less, 5 parts by weight or more and 10 parts by weight or less, 60 parts by weight or more and 195 parts by weight or less, 65 parts by weight or more and 190 parts by weight or less, 75 parts by weight or more and 190 parts by weight or less, 90 parts by weight or more and 190 parts by weight or less, 100 parts by weight or more and 190 parts by weight or less, 125 parts by weight or more and 190 parts by weight or less, 150 parts by weight or more and 190 parts by weight or less, or 170 parts by weight or more and 190 parts by weight or less.

[0079] By adjusting the content of the curing agent within the above-mentioned range, the hardness of the cured product of the semiconductor bonding composition can be reduced, and the crack resistance of the semiconductor bonding film can be further improved. In addition, when the content of the curing agent is within the above-mentioned range, the heat resistance, strength, and adhesiveness of the cured product of the semiconductor bonding composition can be improved.

[0080] According to one embodiment of the present invention, the curing agent may further include at least one of an amine compound, an acid anhydride compound, and an amide compound. Specifically, the amine compound may be one selected from the group consisting of diaminodiphenylmethane, diethylenetriamine, triethylenetetraamine, diaminodiphenylsulfone, isophoronediamine, or a combination thereof. The acid anhydride compound may be one selected from the group consisting of phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, or a combination thereof. The amide compound may be a polyamide resin synthesized from dicyandiamide, a dimer of linoleic acid, and ethylenediamine. When the curing agent further includes the compound, the mechanical properties of the semiconductor adhesive film formed from the semiconductor adhesive composition can be improved.

[0081] According to one embodiment of the present invention, the thermosetting resin can include at least one of a solid epoxy resin and a liquid epoxy resin. The thermosetting resin can exhibit heat resistance and mechanical strength by reacting with a curing agent.

[0082] According to one embodiment of the present invention, the epoxy resin can include at least one of cresol novolac epoxy resin, bisphenol F type epoxy resin, bisphenol F type novolac epoxy resin, bisphenol A type epoxy resin, bisphenol A type novolac epoxy resin, phenol novolac epoxy resin, tetrafunctional epoxy resin, biphenyl type epoxy resin, biphenyl type novolac epoxy resin, triphenol methane type epoxy resin, alkyl modified triphenol methane epoxy resin, naphthalene type epoxy resin, dicyclopentadiene type epoxy resin, dicyclopentadiene modified phenol type epoxy resin, glycidylamine type epoxy resin, and cycloaliphatic epoxy resin. When the thermosetting resin includes the above-mentioned epoxy resin, the semiconductor adhesive composition can realize a semiconductor adhesive film that ensures physical properties, heat resistance, impact resistance, and other mechanical properties suitable for a multi-layered package of semiconductor chips.

[0083] According to one embodiment of the present invention, the epoxy resin may have an average epoxy equivalent of 100 to 1,000. The average epoxy equivalent is determined based on the weight ratio and epoxy equivalent of each epoxy resin contained in the epoxy resin.

[0084] According to one embodiment of the present invention, the thermoplastic resin may include at least one of polyimide resin, polyetherimide resin, polyesterimide resin, polyamide resin, polyethersulfone resin, polyetherketone resin, polyolefin resin, polyvinyl chloride resin, phenoxy resin, butadiene rubber, styrene-butadiene rubber, modified butadiene rubber, reactive butadiene acrylonitrile copolymer rubber, and (meth)acrylate resin. By selecting the thermoplastic resin from the above, it is possible to increase the compatibility with epoxy resin and reduce the stress caused by the semiconductor package.

[0085] According to one embodiment of the present invention, the thermoplastic resin can include a (meth)acrylate resin having a glass transition temperature of -10°C to 30°C and a weight average molecular weight of 50,000 g / mol to 1,000,000 g / mol.

[0086] According to one embodiment of the present invention, the (meth)acrylate resin may contain glycidyl acrylate or glycidyl methacrylate as an epoxy group-containing acrylic copolymer in an amount of 1% by weight to 30% by weight, or 2% by weight to 28% by weight, or 2.5% by weight to 25% by weight based on the total weight. When the content of epoxy groups in the (meth)acrylate resin is within the above-mentioned range, the compatibility and adhesive strength with the epoxy resin may be excellent. In addition, the viscosity increase rate due to curing is appropriate, and the bonding and embedding of solder bumps are sufficiently performed in the thermal compression bonding process of semiconductor elements.

[0087] According to one embodiment of the present invention, the content of the thermoplastic resin may be 5 parts by weight or more and 350 parts by weight or less with respect to 100 parts by weight of the thermosetting resin. Specifically, the content of the thermoplastic resin relative to 100 parts by weight of the thermosetting resin may be 10 parts by weight or more and 300 parts by weight or less, 25 parts by weight or more and 275 parts by weight or less, 50 parts by weight or more and 250 parts by weight or less, 75 parts by weight or more and 200 parts by weight or less, 100 parts by weight or more and 150 parts by weight or less, 5 parts by weight or more and 200 parts by weight or less, 10 parts by weight or more and 175 parts by weight or less, 25 parts by weight or more and 150 parts by weight or less, 50 parts by weight or more and 125 parts by weight or less, 70 parts by weight or more and 100 parts by weight or less, 150 parts by weight or more and 300 parts by weight or less, 180 parts by weight or more and 275 parts by weight or less, 200 parts by weight or more and 250 parts by weight or less, 250 parts by weight or more and 350 parts by weight or less, 275 parts by weight or more and 325 parts by weight or less, or 290 parts by weight or more and 310 parts by weight or less. By adjusting the content of the thermoplastic resin within the above range, the compatibility with the thermosetting resin can be increased, and stress that may be generated from a semiconductor package can be effectively reduced.

[0088] According to one embodiment of the present invention, the semiconductor bonding composition may further include an inorganic filler and a curing catalyst.

[0089] According to one embodiment of the present invention, the inorganic filler can include at least one of alumina, silica, barium sulfate, magnesium hydroxide, magnesium carbonate, magnesium silicate, magnesium oxide, calcium silicate, calcium carbonate, calcium oxide, aluminum hydroxide, aluminum nitride, and aluminum borate.By using the above-mentioned type of inorganic filler, the mechanical properties of the semiconductor adhesive film can be effectively improved.

[0090] According to one embodiment of the present invention, the content of the inorganic filler may be 5 parts by weight or more and 200 parts by weight or less with respect to 100 parts by weight of the thermosetting resin. Specifically, the content of the inorganic filler may be 10 parts by weight or more and 180 parts by weight or less, 20 parts by weight or more and 150 parts by weight or less, 30 parts by weight or more and 120 parts by weight or less, 50 parts by weight or more and 100 parts by weight or less, 75 parts by weight or more and 85 parts by weight or less, 5 parts by weight or more and 100 parts by weight or less, 15 parts by weight or more and 80 parts by weight or less, 30 parts by weight or more and 60 parts by weight or less, 80 parts by weight or more and 150 parts by weight or less, 90 parts by weight or more and 135 parts by weight or less, 100 parts by weight or more and 115 parts by weight or less, 125 parts by weight or more and 200 parts by weight or less, 140 parts by weight or more and 180 parts by weight or less, or 150 parts by weight or more and 175 parts by weight or less. When the content of the inorganic filler is within the above-mentioned range, the mechanical properties of the semiconductor adhesive film formed using the semiconductor adhesive composition can be improved, and the mismatch of the thermal expansion coefficient with the semiconductor chip can be reduced, thereby improving reliability.

[0091] According to one embodiment of the present invention, the average particle size (based on the longest outer diameter) of the inorganic filler may be 0.01 μm or more and 10 μm or less, specifically 0.02 μm or more and 5 μm or less, or 0.03 μm or more and 2 μm or less. When the average particle size of the inorganic filler is within the above-mentioned range, it is possible to prevent the inorganic filler from aggregating in the semiconductor adhesive composition. In addition, when the average particle size of the inorganic filler is within the above-mentioned range, it is possible to prevent the inorganic filler from damaging the semiconductor circuit or reducing the adhesiveness of the semiconductor adhesive film.

[0092] According to one embodiment of the present invention, the curing catalyst can promote the action of the curing agent and the curing of the semiconductor adhesive composition. The curing catalyst can include at least one of a phosphorus-based compound, a boron-based compound, a phosphorus-boron-based compound, and an imidazole-based compound. However, the type of the curing catalyst is not limited, and any curing catalyst known to be used in the manufacture of a semiconductor adhesive film or the like can be used without limitation.

[0093] According to one embodiment of the present invention, the content of the curing catalyst may be 0.1 parts by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the thermosetting resin. Specifically, the content of the curing catalyst may be 0.5 parts by weight or more and 18 parts by weight or less, 1 part by weight or more and 15 parts by weight or less, 2.5 parts by weight or more and 12.5 parts by weight or less, or 5 parts by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the thermosetting resin. By adjusting the content of the curing catalyst within the above-mentioned range, the curing reaction of the semiconductor bonding composition can be effectively promoted.

[0094] According to one embodiment of the present invention, the semiconductor bonding composition may further contain a leveling agent, a dispersant, or a solvent, if necessary.

[0095] According to one embodiment of the present invention, the solvent can be used for the purpose of dissolving the semiconductor bonding composition and imparting a suitable degree of viscosity for coating the composition. Specific examples of the solvent include ketones such as methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene; glycol ethers (cellosolves) such as ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether; acetates such as ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, and dipropylene glycol monomethyl ether acetate; alcohols such as ethanol, propanol, ethylene glycol, propylene glycol, and carbitol; aliphatic hydrocarbons such as octane and decane; petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, and solvent naphtha; and amides such as dimethylacetamide and dimethylformamide (DMF). These solvents can be used alone or in combination of two or more.

[0096] The solvent can be used in an appropriate amount in consideration of the dispersibility, solubility, or viscosity of the semiconductor bonding composition, and for example, the semiconductor bonding composition can contain 0.1 wt% to 70 wt%, or 1 wt% to 65 wt% of the solvent. When the content of the solvent is within the above range, the coating property of the semiconductor bonding composition can be improved, and the semiconductor bonding composition can be smoothly dried, thereby reducing the stickiness of the produced film.

[0097] Meanwhile, the method for preparing the resin composition for bonding a semiconductor is not particularly limited, and the above-mentioned components may be mixed in various ways, for example, by using a mixer.

[0098] One embodiment of the present invention provides a semiconductor adhesive film comprising a cured product of the semiconductor adhesive composition.

[0099] The adhesive film for semiconductor according to one embodiment of the present invention has excellent adhesive strength and can effectively suppress the occurrence of cracks during thermocompression bonding. That is, the adhesive film for semiconductor manufactured from the adhesive composition for semiconductor, which includes the above-mentioned thermosetting resin, thermoplastic resin, and curing agent including at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, can have excellent adhesive performance and crack resistance.

[0100] According to one embodiment of the present invention, the adhesive film for a semiconductor refers to a fully cured film obtained by the coating, drying, and curing processes of the above-mentioned adhesive composition for a semiconductor, and the polymer contained in the adhesive film for a semiconductor may include a reaction product obtained by a crosslinking reaction of components contained in the adhesive composition for a semiconductor.

[0101] In the coating step, a conventional method and device known to be usable for coating the semiconductor bonding composition may be used. For example, the semiconductor bonding composition may be coated on a substrate film as is or after diluting it in a suitable organic solvent using a comma coater, blade coater, lip coater, rod coater, squeeze coater, reverse coater, transfer roll coater, gravure coater, spray coater, or the like, and then dried.

[0102] According to one embodiment of the present invention, the drying temperature may be 50° C. to 200° C. Specifically, the drying temperature may be 60° C. to 170° C., or 70° C. to 150° C. Furthermore, the drying time may be 2 minutes to 30 minutes. Specifically, the drying time may be 2.5 minutes to 25 minutes, 3 minutes to 20 minutes, or 3.5 minutes to 15 minutes.

[0103] According to one embodiment of the present invention, the supporting substrate for supporting the semiconductor adhesive film may be a resin film having excellent heat resistance and chemical resistance, a crosslinked film obtained by crosslinking the resin constituting the resin film, or a film obtained by applying a silicone resin or the like to the surface of the resin film and subjecting it to a release treatment.

[0104] According to one embodiment of the present invention, examples of the resin constituting the resin film include polyester, polyolefin such as polyethylene, polypropylene, polybutene, and polybutadiene, vinyl chloride, ethylene-methacrylic acid copolymer, ethylene-vinyl acetate copolymer, polyester, polyimide, polyethylene terephthalate, polyamide, and polyurethane.

[0105] According to one embodiment of the present invention, the thickness of the supporting substrate is not particularly limited, but may be 3 to 400 μm, alternatively 5 to 200 μm, or alternatively 10 to 150 μm.

[0106] According to one embodiment of the present invention, an adhesive layer may be interposed between the supporting substrate and the semiconductor adhesive film. As the adhesive layer, any adhesive layer known in this field can be applied without any particular limitation.

[0107] One embodiment of the present invention provides a semiconductor package comprising the semiconductor adhesive film.

[0108] The semiconductor package according to one embodiment of the present invention can be excellent in quality. Specifically, the semiconductor adhesive film has excellent adhesive strength and can prevent cracks from occurring, so that the semiconductor package including the semiconductor adhesive film can be excellent in quality and reliability.

[0109] The semiconductor adhesive film can be used for bonding semiconductors, and the semiconductors can include circuit boards and semiconductor chips. The circuit boards can be a printed circuit board (PCB), a semiconductor package board, or a flexible semiconductor package (FPCB) board.

[0110] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples according to the present invention can be modified into various different forms, and the scope of the present invention is not to be construed as being limited to the examples described below. The examples in the present specification are provided to more completely explain the present invention to those having average knowledge in the art. EXAMPLES

[0111] The present invention will now be described in detail with reference to examples.

[0112] Manufacturing Example 1 A mixture was prepared by dissolving 150g of bisphenol A and 14g of formaldehyde in 750ml of 2-ethoxy ethanol in an oil bath. The mixture was heated to 100℃, and 1.5g of sulfuric acid was added dropwise to prepare a mixed solution. The mixed solution was then heated to 135℃ and reacted for 12 hours. After the reaction was completed, the water and solvent in the mixed solution were removed, and the remaining bisphenol A was removed by several washing operations to synthesize a bisphenol A novolak compound.

[0113] In order to cap the ends of the synthesized bisphenol A novolac compound with phenol, 2.8 g of formaldehyde and 57 g of phenol were added to 150 g of the synthesized bisphenol A novolac compound to prepare a mixture, and the mixture was put into 750 ml of 2-ethoxyethanol and dissolved in an oil bath to prepare a mixed solution. Then, the prepared mixed solution was heated to 100 ° C, 0.3 g of sulfuric acid was added dropwise and mixed, and then heated to 135 ° C and stirred for 12 hours. After the reaction was completed, the solvent contained in the mixed solution was removed and several washing operations were carried out. Finally, a bisphenol A novolac resin having phenol capped ends, including the following compound 1-A-1 and the following compound 2-A-1, was obtained. At this time, the obtained bisphenol A novolac resin mainly contains the following compound 2-A-1, and has a softening point of about 130 ° C.

[0114] [ka] [ka] In the compound 1-A-1, n was about 4 to 7, and in the compound 2-A-1, k was about 4 to 7.

[0115] Manufacturing Example 2 A bisphenol A novolak compound was synthesized in the same manner as in Preparation Example 1. Thereafter, a bisphenol A novolak resin having o-cresol capped ends, including the following compound 1-B-1 and the following compound 2-B-1, was obtained in the same manner as in Preparation Example 1, except that 69 g of o-cresol was added instead of phenol in Preparation Example 1. The obtained bisphenol A novolak resin mainly contained the following compound 2-B-1.

[0116] [ka] [ka] In the compound 1-B-1, n was about 4 to 7, and in the compound 2-B-1, k was about 4 to 7.

[0117] Examples and Comparative Examples (Production of Semiconductor Adhesive Composition and Semiconductor Adhesive Film)

[0118] Example 1 (1) Manufacturing of semiconductor bonding composition A thermosetting resin was prepared by mixing 72 g of liquid epoxy resin (RE-310S, Nippon Kayaku Co., Ltd., bisphenol A epoxy resin, epoxy equivalent 180 g / eq) and 10 g of solid epoxy resin (EOCN-104S, Nippon Kayaku Co., Ltd., epoxy equivalent 218 g / eq). In addition, acrylate resin KG-3015 (Mw: 900,000, glass transition temperature: 10°C, methyl ethyl ketone solution with 15% solid content) was prepared as a thermoplastic resin, bisphenol A novolac resin with phenol capped at the end produced in Production Example 1 was prepared as a curing agent, inorganic filler (YA050C, Admatechs, spherical silica, average particle size about 50 nm), imidazole curing catalyst (C11Z-CNZ, Curezol, SHIKOKU), and methyl ethyl ketone as a solvent were prepared.

[0119] Then, the prepared thermosetting resin, thermoplastic resin, curing agent, inorganic filler, curing catalyst, and solvent were mixed to obtain a semiconductor bonding composition (solid content 40% by weight). At this time, about 37 parts by weight of thermoplastic resin, about 68 parts by weight of curing agent, about 152 parts by weight of inorganic filler, and about 2.2 parts by weight of curing catalyst were mixed with respect to 100 parts by weight of thermosetting resin.

[0120] (2) Manufacturing of adhesive films for semiconductors The semiconductor adhesive composition was coated on a release-treated PET film to a thickness of about 80 μm using a doctor blade, and then dried at 110° C. for 5 minutes at a wind speed of 1000 rpm using a wrap oven, and then covered with a protective film to prepare a semiconductor adhesive film with a thickness of 20 μm.

[0121] Example 2 A semiconductor adhesive composition and a semiconductor adhesive film were prepared in the same manner as in Example 1, except that the bisphenol A novolak resin capped with cresol at its end prepared in Preparation Example 2 was used as the curing agent.

[0122] Example 3 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that no inorganic filler was used.

[0123] Example 4 A semiconductor adhesive composition and a semiconductor adhesive film were prepared in the same manner as in Example 1, except that a phenoxy resin (Kukdo Chemical, YP-50s) was used instead of the acrylate resin KG-3015 as the thermoplastic resin.

[0124] Example 5 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that the content of the curing agent was adjusted to about 5 parts by weight per 100 parts by weight of the thermosetting resin.

[0125] Example 6 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that the content of the curing agent was adjusted to about 190 parts by weight per 100 parts by weight of the thermosetting resin.

[0126] Comparative Example 1 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that a bisphenol A novolac type curing agent (KH-6021, DIC) was used as the curing agent.

[0127] Comparative Example 2 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that the content of the curing agent was adjusted to about 200 parts by weight per 100 parts by weight of the thermosetting resin.

[0128] Comparative Example 3 A semiconductor adhesive composition and a semiconductor adhesive film were produced in the same manner as in Example 1, except that the content of the curing agent was adjusted to about 3 parts by weight per 100 parts by weight of the thermosetting resin.

[0129] Test Example 1 (Crack Generation Evaluation) A wafer was prepared that included a bump chip (4.5 mm×4.5 mm) that is a semiconductor element in which lead-free solder is formed to a height of 3 μm on a copper filler having a height of 15 μm and a pitch of 50 μm.

[0130] An adhesive layer of the semiconductor adhesive film of Examples 1 to 6 and Comparative Examples 1 to 3 was placed on the bump surface of the wafer, and vacuum lamination was carried out at 60°C, followed by dicing to separate into individual chips.

[0131] The individual bump chips were bonded to a 6 mm x 8 mm substrate chip having connection pads with a pitch of 50 μm using a thermocompression bonder to manufacture a semiconductor device. At this time, the chips were temporarily bonded at 50 N for 1 second at a head temperature of 100°C, and the head temperature was instantly raised to 280°C to perform thermocompression bonding at 100 N for 5 seconds.

[0132] A temperature cycle test was carried out on the semiconductor device manufactured as described above. First, it was confirmed that no voids or cracks were generated during thermocompression bonding using an ultrasonic imaging device (Scanning Acoustic Tomography (SAT)). The low-temperature and high-temperature conditions were -55°C for 15 minutes and then 125°C for 15 minutes, which was repeated up to 2000 cycles.

[0133] After the temperature cycle test, the semiconductor devices were observed using a scanning acoustic tomography (SAT) and the cross sections of the samples where cracks or delamination were found were polished to confirm the cracks. Those with cracks or delamination were marked with an X, and those without cracks or delamination were marked with an O.

[0134] Test example 2 (reliability evaluation: thermal cycle evaluation) In the same manner as in Test Example 1, ten semiconductor devices each were manufactured to which the adhesive films for semiconductors of Examples 1 to 6 and Comparative Examples 1 to 3 were applied.

[0135] Thereafter, the conditions of the thermal cycle tester were set to -65°C to 150°C, and the 10 semiconductor devices were exposed to the lowest temperature of -65°C for 45 minutes, followed by the highest temperature of 150°C for 45 minutes, with one cycle repeated 500 times to evaluate the occurrence of peeling between the wafer and the semiconductor adhesive film. Specifically, after the completion of the 500 cycles, if no peeling occurred among all the 10 semiconductor devices using an ultrasonic imaging device (Scanning Acousitography (SAT)), it was evaluated as pass (O), and if peeling occurred among even one of the 10 semiconductor devices, it was evaluated as fail (X).

[0136] The measurement results of Test Example 1 and Test Example 2 are shown in Table 1 below.

[0137] [Table 1]

[0138] Referring to Table 1, it was confirmed that the semiconductor adhesive films of Examples 1 to 6 using the curing agent including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 according to one embodiment of the present invention have superior quality in crack evaluation and reliability evaluation compared to the semiconductor adhesive film of Comparative Example 1 using a bisphenol A novolac type curing agent as the curing agent.

[0139] On the other hand, in Comparative Example 2, in which the content of the curing agent was 200 parts by weight per 100 parts by weight of the thermosetting resin, and Comparative Example 3, in which the content of the curing agent was 3 parts by weight, it was confirmed that the crack evaluation and reliability evaluation had inferior quality.

[0140] That is, it is found that a semiconductor bonding composition containing a curing agent according to one embodiment of the present invention can realize a semiconductor bonding film having excellent crack resistance and reliability.

Claims

1. A curing agent comprising at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: 【Chemistry 1】 【Chemistry 2】 In the above Chemical Formula 1 and Chemical Formula 2, R １ , R ２ , R ３ and R ４ are each independently a monocyclic hydroxyphenyl group; n is an integer from 1 to 50, and k is an integer from 1 to 50.

2. The curing agent according to claim 1, which contains at least a compound represented by the following chemical formula 2-1: 【Chemistry 3】 In the above chemical formula: R ３ and R ４ are each independently a monocyclic hydroxyphenyl group; k is an integer from 1 to 50.

3. The monocyclic hydroxyphenyl group is Unsubstituted; or 3. The curing agent according to claim 1, which is a hydroxyphenyl group substituted with at least one of a linear or branched alkyl group having 1 to 10 carbon atoms and an alicyclic alkyl group having 4 to 10 carbon atoms.

4. The curing agent according to any one of claims 1 to 3, wherein the single ring hydroxyphenyl group has one of the following chemical structures: 【Chemistry 4】 In the above chemical structures, "*" denotes the point of attachment.

5. Thermosetting resin; Thermoplastic resins; and A composition for bonding a semiconductor, comprising: a compound represented by the following Chemical Formula 1; and a curing agent comprising at least one of a compound represented by the following Chemical Formula 2: 【Chemistry 5】 【Chemistry 6】 In the above Chemical Formula 1 and Chemical Formula 2, R １ , R ２ , R ３ and R ４ are each independently a monocyclic hydroxyphenyl group; n is an integer from 1 to 50, and k is an integer from 1 to 50.

6. The semiconductor bonding composition according to claim 5, wherein the curing agent contains at least a compound represented by the following chemical formula 2-1: 【Chemistry 7】 In the above chemical formula: R ３ and R ４ are each independently a monocyclic hydroxyphenyl group; k is an integer from 1 to 50.

7. The monocyclic hydroxyphenyl group is Unsubstituted; or 7. The semiconductor bonding composition according to claim 5, which is a hydroxyphenyl group substituted with at least one of a linear or branched alkyl group having 1 to 10 carbon atoms and an alicyclic alkyl group having 4 to 10 carbon atoms.

8. The semiconductor bonding composition according to any one of claims 5 to 7, wherein the monocyclic hydroxyphenyl group has any one of the following chemical structures: 【Chemistry 8】 In the above chemical structures, "*" denotes the point of attachment.

9. The semiconductor bonding composition according to claim 5 , wherein the content of the curing agent is 5 parts by weight or more and 195 parts by weight or less with respect to 100 parts by weight of the thermosetting resin.

10. The semiconductor bonding composition according to claim 5 , wherein the thermosetting resin includes at least one of a solid epoxy resin and a liquid epoxy resin.

11. The semiconductor bonding composition according to any one of claims 5 to 10, wherein the thermoplastic resin contains at least one of a polyimide resin, a polyetherimide resin, a polyesterimide resin, a polyamide resin, a polyethersulfone resin, a polyetherketone resin, a polyolefin resin, a polyvinyl chloride resin, a phenoxy resin, a butadiene rubber, a styrene-butadiene rubber, a modified butadiene rubber, a reactive butadiene acrylonitrile copolymer rubber, and a (meth)acrylate resin.

12. The semiconductor bonding composition according to claim 5 , wherein the content of the thermoplastic resin is 5 parts by weight or more and 350 parts by weight or less with respect to 100 parts by weight of the thermosetting resin.

13. The semiconductor bonding composition according to claim 5 , further comprising an inorganic filler and a curing catalyst.

14. The semiconductor bonding composition according to claim 13, wherein the inorganic filler comprises at least one of alumina, silica, barium sulfate, magnesium hydroxide, magnesium carbonate, magnesium silicate, magnesium oxide, calcium silicate, calcium carbonate, calcium oxide, aluminum hydroxide, aluminum nitride, and aluminum borate.

15. The semiconductor bonding composition according to claim 13 or 14, wherein the content of the inorganic filler is 5 parts by weight or more and 200 parts by weight or less with respect to 100 parts by weight of the thermosetting resin.

16. The semiconductor bonding composition according to any one of claims 13 to 15, wherein the curing catalyst includes at least one of a phosphorus-based compound, a boron-based compound, a phosphorus-boron-based compound, and an imidazole-based compound.

17. The semiconductor bonding composition according to claim 13 , wherein the content of the curing catalyst is 0.1 parts by weight or more and 20 parts by weight or less with respect to 100 parts by weight of the thermosetting resin.

18. A semiconductor adhesive film comprising a cured product of the semiconductor adhesive composition according to any one of claims 5 to 17.

19. A semiconductor package comprising the semiconductor adhesive film according to claim 18.

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