Adhesive composition for laser debonding and coating layer

Abstract

An adhesive composition for laser debonding according to exemplary embodiments comprises: a first polymer including a first repeating unit represented by a specific chemical formula and a second repeating unit including an acyl group; and a second polymer including a third repeating unit represented by a specific chemical formula and a fourth repeating unit including an acyl group. A coating layer for laser debonding according to exemplary embodiments comprises a polymer including a repeating unit having a specific chemical formula. Accordingly, chemical resistance and laser debonding efficiency can be improved.

Description

Adhesive composition and coating layer for laser debonding

[0001] The present invention relates to an adhesive composition and a coating layer for laser debonding. More specifically, the present invention relates to an adhesive composition and a coating layer for laser debonding comprising a polymer.

[0002]

[0003] The recent trend toward miniaturization of electronic devices has led to a demand for miniaturization of the components within them. For example, miniaturization can be achieved by increasing semiconductor integration and thinning wafers. However, due to physical limitations, semiconductor packaging is being introduced as a post-process.

[0004] Semiconductor packaging requires handling thin wafers, and cracks and breakage can occur during this process. Therefore, research is being conducted on methods for performing semiconductor packaging by temporarily attaching the wafer to a carrier wafer and then debonding it.

[0005] For example, debonding can be performed by forming microscopic holes in a carrier wafer and allowing a solvent to permeate the holes. However, the cost of using processed carrier wafers is high, and the large amount of solvent used can expose workers to hazardous environments.

[0006] Alternatively, debonding can be achieved by attaching the wafer to a carrier wafer using adhesive, then physically separating it using force or heat. However, the physical external force or heating process can damage the wafer, which can reduce semiconductor yield.

[0007] In this regard, Korean Patent Publication No. 10-2022-0159031 discloses a multi-layer debonding tape, and Korean Patent Publication No. 10-2019-0093162 discloses an adhesive composition comprising a mercapto compound and a polyurethane composite resin. However, a method for minimizing wafer damage remains needed.

[0008]

[0009] An object of the present invention is to provide an adhesive composition for laser debonding with improved chemical resistance and debonding efficiency.

[0010] An object of the present invention is to provide a coating layer for laser debonding with improved chemical resistance and debonding efficiency.

[0011] An object of the present invention is to provide a method for manufacturing a semiconductor package with improved chemical resistance and debonding efficiency.

[0012]

[0013] An adhesive composition for laser debonding according to embodiments of the present disclosure comprises a first polymer comprising a first repeating unit represented by Chemical Formula 1; and a second polymer comprising a second repeating unit comprising an acyl group; and a third repeating unit represented by Chemical Formula 6; and a fourth repeating unit comprising an acyl group.

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 6]

[0017]

[0018] In chemical formula 1, X1 is a direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R ais an alkyl group having 1 to 5 carbon atoms, which is substituted or unsubstituted with a hydrogen atom or a halogen atom, and R1 and R2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0019] In chemical formula 6, D is a divalent organic group having 6 to 30 carbon atoms.

[0020] According to exemplary embodiments, the second repeating unit may include a repeating unit represented by Chemical Formula 2 or Chemical Formula 3.

[0021] [Chemical Formula 2]

[0022]

[0023] [Chemical Formula 3]

[0024]

[0025] In chemical formula 2, X2 is a direct bond, O, S, NR b , N=N or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R b is an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a hydrogen atom or a halogen atom, and R3 and R4 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0026] In chemical formula 3, A is arylene having 6 to 10 carbon atoms or heteroarylene having 6 to 10 carbon atoms, and R3 and R4 are each the same as the definitions of R3 and R4 in chemical formula 2.

[0027] According to exemplary embodiments, the first polymer may further include a terminal portion comprising a carboxyl group, and is bonded to at least one of the first repeating unit and the second repeating unit.

[0028] According to exemplary embodiments, the terminal portion may be represented by Chemical Formula 4 or Chemical Formula 5.

[0029] [Chemical Formula 4]

[0030]

[0031] [Chemical Formula 5]

[0032]

[0033] In chemical formula 4, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R5 and R6 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom.

[0034] In chemical formula 5, R5 and R6 are each defined as R5 and R6 in chemical formula 4.

[0035] According to exemplary embodiments, the first repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 1-1 to 1-3.

[0036] [Chemical Formula 1-1]

[0037]

[0038] [Chemical Formula 1-2]

[0039]

[0040] [Chemical Formula 1-3]

[0041] .

[0042] According to exemplary embodiments, the second repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 2-1 to 2-3 and the compounds represented by the following chemical formulae 3-1 to 3-2.

[0043] [Chemical Formula 2-1]

[0044]

[0045] [Chemical Formula 2-2]

[0046]

[0047] [Chemical Formula 2-3]

[0048]

[0049] [Chemical Formula 3-1]

[0050]

[0051] [Chemical Formula 3-2]

[0052] .

[0053] According to exemplary embodiments, the terminal portion may be formed from one or more of the compounds represented by the following chemical formulae 4-1 to 4-6 and the compound represented by the following chemical formula 5-1.

[0054] [Chemical Formula 4-1]

[0055]

[0056] [Chemical Formula 4-2]

[0057]

[0058] [Chemical Formula 4-3]

[0059]

[0060] [Chemical Formula 4-4]

[0061]

[0062] [Chemical Formula 4-5]

[0063]

[0064] [Chemical Formula 4-6]

[0065]

[0066] [Chemical Formula 5-1]

[0067] .

[0068] According to exemplary embodiments, the fourth repeating unit may include a repeating unit represented by the following chemical formula 7.

[0069] [Chemical Formula 7]

[0070]

[0071] In chemical formula 7, E is a tetravalent organic group having 6 to 30 carbon atoms.

[0072] According to exemplary embodiments, the second polymer of the adhesive composition for laser debonding may further include a side group that is bonded to the fourth repeating unit and includes at least one of an ether group and an ester group.

[0073] According to exemplary embodiments, the branching moiety may be derived from one or more of a glycidyl ether compound and a glycidyl ester compound.

[0074] According to exemplary embodiments, the third repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 6-1 to 6-5.

[0075] [Chemical Formula 6-1]

[0076]

[0077] [Chemical Formula 6-2]

[0078]

[0079] [Chemical Formula 6-3]

[0080]

[0081] [Chemical Formula 6-4]

[0082]

[0083] [Chemical Formula 6-5]

[0084] .

[0085] According to exemplary embodiments, the fourth repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 7-1 to 7-5.

[0086] [Chemical Formula 7-1]

[0087]

[0088] [Chemical Formula 7-2]

[0089]

[0090] [Chemical Formula 7-3]

[0091]

[0092] [Chemical Formula 7-4]

[0093]

[0094] [Chemical Formula 7-5]

[0095] .

[0096] According to exemplary embodiments, the side branch portion is selected from the group consisting of glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, butyl glycidyl ether, t-butyl glycidyl ether, glycidyl lauryl ether, allyl glycidyl ether, glycidyl phenyl ether, benzyl glycidyl ether, glycidyl 2-methoxyphenyl ether, glycidyl methacrylate, glycidyl acrylate, glycidyl 4-t-butylbenzoate, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, diglycidyl 4-cyclohexene-1,2-dicarboxylate, diglycidyl 1,2-cyclohexanedicarboxylate, 2,2-bis(4-glycidyloxyphenyl)propane and It can be formed from one or more of 1,4-butanediol diglycidyl ethers.

[0097] According to exemplary embodiments, the weight ratio of the first polymer and the second polymer may be 1:9 to 9:1.

[0098] The coating layer for laser debonding according to embodiments of the present invention comprises a polymer including a fifth repeating unit represented by Chemical Formula 9 or Chemical Formula 10; and a sixth repeating unit represented by Chemical Formula 11.

[0099] [Chemical Formula 9]

[0100]

[0101] [Chemical Formula 10]

[0102]

[0103] [Chemical Formula 11]

[0104]

[0105] In chemical formula 9, X 10 Silver direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R a is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and X 20 Silver direct bond, O, S, NR b Or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R b is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R 10 , R 20 , R 30 and R 40 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0106] In chemical formula 10, C is arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and X 10, R 10 , R 20 , R 30 and R 40 Each of the above chemical formula 9 is X 10, R 10 , R 20 , R 30 and R 40 is identical to the definition of .

[0107] In chemical formula 11, D is a divalent organic group having 6 to 30 carbon atoms, E is a tetravalent organic group having 6 to 30 carbon atoms, and R 50is a substituent containing at least one of a hydroxyl group, an ether group, and an ester group.

[0108] According to exemplary embodiments, the coating layer for laser debonding may include a polymer further including a terminal portion represented by Chemical Formula 4, Chemical Formula 4a, Chemical Formula 5, or Chemical Formula 5a. Chemical Formula 4 or Chemical Formula 5 may be the same as described above. Chemical Formula 4a or Chemical Formula 5a may be as follows.

[0109] [Chemical Formula 4a]

[0110]

[0111] [Chemical Formula 5a]

[0112]

[0113] In chemical formula 4a, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R5 and R6 can each independently be a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom.

[0114] In chemical formula 5a, R5 and R6 may be the same as the above definitions.

[0115] According to exemplary embodiments, the coating layer for laser debonding may have a thickness of 0.2 μm to 2.0 μm.

[0116] According to exemplary embodiments, the coating layer for laser debonding may have a laser transmittance of 15% or less.

[0117] According to exemplary embodiments, the coating layer for laser debonding may have an adhesive strength of 12 mN or more.

[0118] According to exemplary embodiments, the coating layer for laser debonding can be decomposed by a laser having a pulse energy of 180 mJ or less.

[0119] According to a method for manufacturing a semiconductor package according to embodiments of the present invention, a mixture of an adhesive composition for laser debonding and a solvent according to the above-described embodiments is prepared. The mixture is coated on one surface of a substrate. The coated mixture is heated to form a coating layer for laser debonding. A wafer is attached on the coating layer for laser debonding. The wafer is processed. A laser is irradiated to the other surface of the substrate.

[0120] According to exemplary embodiments, the step of heating the coated mixture to form a coating layer for laser debonding may include a step of soft baking at 100°C to 150°C; and a step of post baking at 250°C to 350°C.

[0121] According to exemplary embodiments, in the step of irradiating the laser, a laser having a pulse energy of 180 mJ or less can be irradiated.

[0122]

[0123] According to exemplary embodiments, the adhesive composition and coating layer for laser debonding may include a polymer having a specific chemical formula. Accordingly, the adhesive composition can be decomposed under relatively mild conditions by a laser, thereby improving laser debonding efficiency. Furthermore, resistance to chemicals may be enhanced.

[0124] Furthermore, when the adhesive composition and coating layer for laser debonding are used in semiconductor packaging, physical action and / or high temperatures may not be required for wafer separation. Furthermore, the adhesive composition and coating layer's chemical resistance may be enhanced. Therefore, wafer damage can be suppressed, thereby improving yield in the semiconductor packaging process.

[0125]

[0126] FIG. 1 is a schematic diagram illustrating a part of a method for manufacturing a semiconductor package according to exemplary embodiments.

[0127] FIG. 2 is a schematic diagram illustrating a part of a method for manufacturing a semiconductor package according to exemplary embodiments.

[0128]

[0129] Exemplary embodiments of the present invention provide an adhesive composition for laser debonding (hereinafter, abbreviated as "adhesive composition") comprising a polymer having a specific chemical formula. Furthermore, the present invention provides a coating layer for laser debonding (hereinafter, abbreviated as "coating layer") comprising the polymer having the specific chemical formula. Furthermore, the present invention provides a method for manufacturing a semiconductor package using the adhesive composition for laser debonding.

[0130] Hereinafter, the present invention will be described in detail. However, this is merely exemplary and the present invention is not limited to the specific embodiments described as examples.

[0131] In the present specification, a "divalent organic group" may refer to an organic group capable of forming two bonds, including a straight-chain and / or branched-chain saturated hydrocarbon group, a straight-chain and / or branched-chain unsaturated hydrocarbon group, a straight-chain and / or aromatic group, etc. For example, a divalent organic group may refer to an alkylene group, an alkenylene group, a cycloalkylene group, an arylene group, an alkylarylene group, a heteroarylene group, an alkylheteroarylene group, etc. A "tetravalent organic group" may refer to an organic group capable of forming four bonds, including a straight-chain and / or branched-chain saturated hydrocarbon group, a straight-chain and / or branched-chain unsaturated hydrocarbon group, a straight-chain and / or aromatic group, etc.

[0132] In this specification, "alkyl group" may refer to a monovalent hydrocarbon group formed by removing one hydrogen atom of alkyl. For example, the alkyl group may include a methyl group, an ethyl group, a propyl group, a butyl group, etc. In addition, the alkyl group includes a hydrocarbon group in a straight or branched chain form. For example, the alkyl group may include an isopropyl group, a tert-butyl group, an iso-butyl group, etc.

[0133] As used herein, the term "alkenyl group" may refer to a monovalent unsaturated hydrocarbon group formed by removing one hydrogen atom from an alkenyl group. The alkenyl group may include a double bond, and the position of the double bond may not be limited. For example, the alkenyl group may include an ethene group, a propenyl group, a butenyl group, and the like.

[0134] In this specification, "alkylene group" may refer to a divalent hydrocarbon group formed by removing one more hydrogen atom from an alkyl group. For example, the alkylene group may include a methylene group, an ethylene group, a propylene group, a butylene group, and the like.

[0135] In this specification, “halogen atom” may represent F, Br, Cl, or I.

[0136] In this specification, "carbon number n" may represent an aliphatic ring or aromatic ring composed of carbon number n. For example, carbon number n represents the number of carbons, and may not include the number of heteroatoms. For example, the number of carbons contained in a substituent may not be included.

[0137] As used herein, "cycloalkylene" may refer to a simple or fused cyclic divalent hydrocarbon group formed by the removal of two hydrogen atoms from a cycloalkyl structure. For example, a cycloalkylene having 5 to 7 carbon atoms may include cyclopentylene, cyclohexylene, and the like.

[0138] As used herein, "cycloalkenylene" may refer to a simple or fused cyclic divalent hydrocarbon group formed by the removal of two hydrogen atoms from a cycloalkene structure. For example, a cycloalkenylene having 5 to 7 carbon atoms may include a structure formed by the removal of two hydrogen atoms from different carbons from cyclopentenylene, cyclohexenylene, or norbornene.

[0139] As used herein, "arylene" may refer to a functional group formed by the removal of two hydrogen atoms from an aromatic ring. For example, arylene may include phenylene and the like.

[0140] As used herein, "heteroarylene" may refer to a functional group formed by replacing one or more carbon atoms in an aromatic ring with a heteroatom (e.g., N, S, O) and removing two hydrogen atoms. For example, heteroarylene may include pyridylene and the like.

[0141] In this specification, "acyl group" means -C(=O)R x (R x It can represent a functional group represented by a hydrocarbon group or an aromatic functional group.

[0142] According to exemplary embodiments, the first polymer of the adhesive composition for laser debonding may include a first repeating unit represented by Chemical Formula 1.

[0143] [Chemical Formula 1]

[0144]

[0145] In chemical formula 1, X1 is a direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R a is an alkyl group having 1 to 5 carbon atoms, which is unsubstituted or substituted with a hydrogen atom or a halogen atom. R1 and R2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0146] According to exemplary embodiments, X1 can be a direct bond or an alkylene group having 1 to 10 carbon atoms which is unsubstituted or substituted with a halogen atom. In some embodiments, X1 can be a direct bond or an alkylene group having 1 to 10 carbon atoms which is unsubstituted or substituted with a fluorine atom. In some embodiments, X1 can be a direct bond, an alkylene group having 1 to 5 carbon atoms, or an alkylene group having 1 to 5 carbon atoms which is substituted with a fluorine atom. In some embodiments, X1 can be a direct bond, -C(CH3)2-, or -C(CF3)2-.

[0147] According to exemplary embodiments, R1 and R2 are bonded to an arylene group, and the bonding position may not be limited.

[0148] In some embodiments, R1 and R2 can each be hydrogen.

[0149] According to exemplary embodiments, the first repeating unit may be formed from a diamine-based compound containing a hydroxyl group. For example, the diamine-based compound may include compounds represented by the following chemical formulas. The following chemical formulas are provided for illustrative purposes only, and the diamine-based compound is not limited to the following compounds.

[0150] , , , , , ,

[0151] According to exemplary embodiments, the first repeating unit may be formed from one or more of the diamine compounds represented by the following chemical formulas.

[0152] , , and .

[0153] In chemical formula 1, the hydroxyl group (-OH) can be bonded to an arylene group, and the bonding position may not be limited.

[0154] According to exemplary embodiments, the hydroxyl group in Chemical Formula 1 may be bonded to the arylene group so as to be adjacent to the -NH- group bonded to the arylene group. For example, the -NH- and hydroxyl groups may be bonded at an ortho position to the arylene group. Accordingly, a ring may be formed through the reaction between the -NH- and hydroxyl groups during the curing process of the adhesive composition, and laser debonding efficiency may be improved.

[0155] According to exemplary embodiments, the first polymer included in the adhesive composition for laser debonding may include a second repeating unit comprising an acyl group.

[0156] According to exemplary embodiments, the second repeating unit may include two or more acyl groups. For example, the second repeating unit may be -C(=O)-R a -C(=O)- can be expressed as R a may contain a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

[0157] According to exemplary embodiments, the second repeating unit may include a repeating unit represented by Chemical Formula 2 or Chemical Formula 3. For example, the second repeating unit may be represented by Chemical Formula 2 or Chemical Formula 3.

[0158] [Chemical Formula 2]

[0159]

[0160] [Chemical Formula 3]

[0161]

[0162] In chemical formula 2, X2 is a direct bond, O, S, NR b , N=N or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R bis an alkyl group having 1 to 5 carbon atoms, which is unsubstituted or substituted with a hydrogen atom or a halogen atom. R3 and R4 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0163] In chemical formula 3, A is arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms. R3 and R4 may have the same definitions as R3 and R4 in chemical formula 2, respectively.

[0164] According to exemplary embodiments, X2 can be a direct bond, an alkylene group having 1 to 5 carbon atoms which is unsubstituted or substituted with O, S, N=N, or a halogen atom. In some embodiments, X2 can be a direct bond, O, N=N, or an alkylene group having 1 to 5 carbon atoms which is substituted with a halogen atom. In some embodiments, X2 can be a direct bond, O, or N=N.

[0165] According to exemplary embodiments, A may be an arylene having 6 carbon atoms or a heteroarylene having 6 carbon atoms. The heteroarylene having 6 carbon atoms may include N or S as a heteroatom. In some embodiments, A may be phenylene or pyridylene.

[0166] According to exemplary embodiments, R3 and R4 are bonded to arylene or heteroarylene, and the bonding position may not be limited. In some embodiments, R3 and R4 may each be hydrogen.

[0167] According to exemplary embodiments, the second repeating unit may be formed from a diacyl chloride compound.

[0168] For example, the diacyl chloride compounds include 4,4'-oxydibenzoyl chloride, terephthaloyl chloride, isophthaloyl chloride, 5-chlorobenzene-1,3-dicarbonyl chloride, 4,4'-biphenyl dicarbonyl chloride, diphnylmethane-4,4'dicarbonyl chloride, diphnylpropane-4,4'dicarbonyl chloride, azobenzene-4,4'-dicarbonyl dichloride, and pyridine-2,6-dicarbonyl. It may include pyridine-2,6-dicarbonyl dichloride, pyridine-2,5-dicarbonyl dichloride, benzophenone-4,4'-dicarbonyl dichloride, etc.

[0169] According to exemplary embodiments, the second repeating unit may be formed from one or more of the compounds represented by the following chemical formulas:

[0170] , , , , and .

[0171] In the first polymer according to exemplary embodiments, at least one of the first repeating unit and the second repeating unit may be bonded to a terminal portion including a carboxyl group.

[0172] For example, a polymerization reaction can occur when a precursor of a first repeating unit is combined with a precursor of a second repeating unit while being combined with the terminal portion, and thus an adhesive composition having a controlled molecular weight, etc. can be manufactured.

[0173] According to exemplary embodiments, the terminal portion is -C(=O)R x It may include an acyl group represented by R. x It may be an alkyl group having 1 to 10 carbon atoms substituted with a carboxyl group, an alkenyl group having 1 to 10 carbon atoms substituted with a carboxyl group, a cycloalkyl group having 5 to 10 carbon atoms substituted with a carboxyl group, a cycloalkenyl group having 5 to 10 carbon atoms substituted with a carboxyl group, an arylene group having 6 to 10 carbon atoms substituted with a carboxyl group, or a heteroarylene group having 6 to 10 carbon atoms substituted with a carboxyl group.

[0174] According to exemplary embodiments, the terminal portion may be represented by Chemical Formula 4 or Chemical Formula 5.

[0175] [Chemical Formula 4]

[0176]

[0177] [Chemical Formula 5]

[0178]

[0179] In chemical formula 4, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms. R5 and R6 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom.

[0180] In chemical formula 5, R5 and R6 may have the same definitions as R5 and R6 in chemical formula 4, respectively.

[0181] According to exemplary embodiments, B can be a cycloalkylene having 6 to 7 carbon atoms, a cycloalkenylene having 6 to 7 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 6 to 10 carbon atoms. In some embodiments, B can be a cycloalkylene having 6 to 7 carbon atoms, a cycloalkenylene having 6 to 7 carbon atoms, a phenylene, or a pyridylene.

[0182] According to exemplary embodiments, in chemical formula 4, R5 and R6 are each bonded to the above-described B, and the bonding position may not be limited.

[0183] According to exemplary embodiments, R5 and R6 can each independently be a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms. In some embodiments, one of R5 and R6 can be a hydrogen atom, and the other can be an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 1 to 5 carbon atoms. In one embodiment, R5 can be a hydrogen atom, and R6 can be a methyl group. In one embodiment, R5 can be a hydrogen atom, and R6 can be a propenyl group. In one embodiment, R5 and R6 can be a hydrogen atom.

[0184] According to exemplary embodiments, the terminal portion may be formed from a dicarboxylic anhydride compound.

[0185] The above dicarboxylic acid anhydride compounds include, for example, phthalic anhydride, maleic anhydride, succinic anhydride, glutamic anhydride, itaconic anhydride, cis-5-norbornene-endo-2,3-dicarboxylic anhydride, methyl-5-norbornene-2,3-dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, allyl succinic anhydride, It may include cis-1,2-cyclohexanedicarboxylic anhydride, 2,3-pyridinedicarboxylic anhydride, trimellitic anhydride, endo methylene tetrahydrophthalic anhydride, methylene citraconic anhydride, etc.

[0186] According to exemplary embodiments, the terminal portion may be formed from one or more of the compounds represented by the following chemical formulas:

[0187] , , , , , , and .

[0188] The number of repetitions of the first repeating unit and the second repeating unit can be adjusted to control the molecular weight of the first polymer.

[0189] According to exemplary embodiments, the weight average molecular weight of the first polymer may be from 5,000 to 50,000, from 6,000 to 35,000, from 7,000 to 30,000, or from 7,500 to 25,000.

[0190] A coating layer with a controlled thickness within the above range can be easily formed, and thus a coating layer with improved chemical resistance, transmittance, and other characteristics can be formed.

[0191] According to exemplary embodiments, the molar ratio of the second repeating unit to the first repeating unit may be 0.6 to 1.2, or 0.7 to 1.1.

[0192] According to exemplary embodiments, the molar ratio of the terminal portion to the first repeating unit may be 0.1 to 0.6, 0.2 to 0.5, or 0.3 to 0.4.

[0193] Within the above range, the laser debonding properties of the adhesive composition and the coating layer formed thereby can be implemented.

[0194] According to exemplary embodiments, the second polymer of the adhesive composition for laser debonding may include a third repeating unit represented by chemical formula 6.

[0195] [Chemical Formula 6]

[0196]

[0197] In chemical formula 6, D is a divalent organic group having 6 to 30 carbon atoms.

[0198] For example, the above-mentioned two-valent organic group may include a heteroatom. The heteroatom may be included in the main skeleton or a branch, and for example, the heteroatom may be included in the form of a trifluoromethyl group (-CF3), an ether group (-O-), a sulfonyl group (-SO2-), etc.

[0199] According to exemplary embodiments, D may be a divalent aliphatic organic group having 6 to 30 carbon atoms or a divalent aromatic organic group having 6 to 30 carbon atoms. For example, D may include alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, heteroalkynylene, cycloalkylene, cycloalkenylene, cycloalkynylene, heterocycloalkylene, heterocycloalkenylene, heterocycloalkynylene, arylene, heteroarylene, and the like having 6 to 30 carbon atoms.

[0200] In some embodiments, D may be a divalent aromatic organic group having 6 to 18 carbon atoms. In some embodiments, D may be a substituted or unsubstituted divalent aromatic organic group having 6 to 12 carbon atoms. For example, a structure may be included in which one of the terminal hydrogens in the aromatic ring is substituted with a halogen atom, an alkylene group having 1 to 10 carbon atoms that is substituted or unsubstituted with a halogen atom, or in which each of two or more aromatic rings has a terminal hydrogen removed and is connected to each other via O, S, SO2, CO, C(O)O, etc. When a part of the aromatic organic group is substituted, the carbon included in the substituent may not be included in the carbon number of the aromatic organic group.

[0201] In some embodiments, the third repeating unit may be represented by the following chemical formula 6a or chemical formula 6b.

[0202] [Chemical Formula 6a]

[0203]

[0204] [Chemical Formula 6b]

[0205]

[0206] In chemical formula 6a, Y1 is a direct bond, O, S, SO2, CO, C(O)O, an alkylene group having 1 to 10 carbon atoms which is unsubstituted or substituted with a halogen atom, and R7 and R8 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom.

[0207] In chemical formula 6b, R7 is defined as R7 in chemical formula 6a.

[0208] According to exemplary embodiments, R7 and R8 are bonded to an arylene group, and the bonding position may not be limited.

[0209] In some embodiments, R7 and R8 can each be a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, which is unsubstituted or substituted with a fluorine atom.

[0210] According to exemplary embodiments, the third repeating unit may be derived from a diamine compound. For example, the third repeating unit may be formed by reacting a diamine compound with a dianhydride compound, as described below.

[0211] For example, the diamine compound is 3,4-oxydianiline, 4,4-oxydianiline (ODA), 4,4-methylenedianiline, 1,3-bis(3-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, bis[4-(3-aminophenoxy)phenyl]-sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, 2,2-bis(trifluoromethyl)benzidine, 2,2-bis[4-(4-aminophenoxy)-phenyl]hexafluoropropane), 2,2-bis(trifluoromethyl)benzidine (TFMB), 3,3-sulfonyldianiline, 4,4-diaminodiphenylsulfone, 4,4-(1,3-phenylenedioxy)dianiline, 9,9-bis(4-amino-3-fluorophenyl)fluorine, 4-aminophenyl 4-aminobenzoate, It may include 4,4-diaminobenzanilide, 9,9-bis(4-aminophenyl)fluorine, etc. These may be used alone or in combination of two or more.

[0212] According to exemplary embodiments, the third repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 6-1 to 6-5.

[0213] [Chemical Formula 6-1]

[0214]

[0215] [Chemical Formula 6-2]

[0216]

[0217] [Chemical Formula 6-3]

[0218]

[0219] [Chemical Formula 6-4]

[0220]

[0221] [Chemical Formula 6-5]

[0222] .

[0223] According to exemplary embodiments, the second polymer of the adhesive composition for laser debonding may include a fourth repeating unit comprising an acyl group.

[0224] According to exemplary embodiments, the fourth repeating unit may comprise two or more acyl groups. In some embodiments, the fourth repeating unit may comprise a carboxyl group.

[0225] According to exemplary embodiments, the fourth repeating unit may include a divalent aliphatic organic group having 6 to 30 carbon atoms or a divalent aromatic organic group having 6 to 30 carbon atoms.

[0226] For example, the fourth repeating unit may include two or more acyl groups and two or more carboxyl groups bonded to a divalent aliphatic organic group having 6 to 30 carbon atoms. For example, the fourth repeating unit may include two or more acyl groups and two or more carboxyl groups bonded to a divalent aromatic organic group having 6 to 30 carbon atoms.

[0227] According to exemplary embodiments, the fourth repeating unit may include a repeating unit represented by chemical formula 7.

[0228] [Chemical Formula 7]

[0229]

[0230] In chemical formula 7, E is a tetravalent organic group having 6 to 30 carbon atoms.

[0231] According to exemplary embodiments, E may be a tetravalent aliphatic organic group having 6 to 30 carbon atoms or a tetravalent aromatic organic group having 6 to 30 carbon atoms.

[0232] According to exemplary embodiments, E may be a tetravalent aromatic organic group having 6 to 30 carbon atoms. In some embodiments, E may be a tetravalent aromatic organic group having 6 to 18 carbon atoms. For example, a structure may be included in which one of the terminal hydrogens in the aromatic ring is substituted with a halogen atom, an alkylene group having 1 to 10 carbon atoms that is substituted with a halogen atom or is unsubstituted, or in which each of two or more aromatic rings has a terminal hydrogen removed and is connected to each other via O, S, SO2, CO, C(O)O, etc. When a part of the aromatic organic group is substituted, the carbon included in the substituent may not be included in the carbon number of the aromatic organic group.

[0233] In some embodiments, the fourth repeating unit may be represented by the following chemical formula 7a or chemical formula 7b.

[0234] [Chemical Formula 7a]

[0235]

[0236] [Chemical Formula 7b]

[0237]

[0238] In chemical formula 7a, Y2 is a direct bond, O, S, SO2, CO, C(O)O, an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R9 and R 10 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom.

[0239] In chemical formula 7b, R9 is defined as R9 in chemical formula 7a.

[0240] According to exemplary embodiments, R9 and R 10 is bonded to an arylene group, and the bonding position may not be limited.

[0241] In some embodiments, R9 and R 10 Each can be a hydrogen atom.

[0242] According to exemplary embodiments, the fourth repeating unit may be derived from a dianhydride compound. For example, the fourth repeating unit may be formed by a reaction between a dianhydride compound and a diamine compound.

[0243] For example, the dianhydride compound is 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA), pyromellitic dianhydride (PMDA), 3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA), 2,3,3',4-biphenyltetracarboxylic dianhydride (a-BPDA), 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 6FDA), 4,4'-oxydiphthalic anhydride (4,4'-oxydiphthalic Anhydride, ODPA), 3,3',4,4'-diphenylsulfone-tetracarboxylic dianhydride (3,3',4,4'-diphenylsulfone-tetracarboxylic dianhydride (DSDA), 2,2-bis[4-(3,4-dicarboxyphenoxy) phenyl] propane dianhydride (BPADA), hydroquinone diphthalic anhydride (HQDA), 1,2,4,5-cyclohexane-tetracarboxylic dianhydride (CHDA), etc. These may be used alone or in combination of two or more.

[0244] According to exemplary embodiments, the fourth repeating unit may be formed from one or more of the compounds represented by the following chemical formulae 7-1 to 7-5.

[0245] [Chemical Formula 7-1]

[0246]

[0247] [Chemical Formula 7-2]

[0248]

[0249] [Chemical Formula 7-3]

[0250]

[0251] [Chemical Formula 7-4]

[0252]

[0253] [Chemical Formula 7-5]

[0254] .

[0255] According to exemplary embodiments, the second polymer of the adhesive composition for laser debonding may further include a branched moiety that is bonded to the fourth repeating unit and includes at least one of an ether group and an ester group. For example, the branched moiety may include at least one or two of an ether group (-O-) and an ester group (-C(O)O-).

[0256] For example, the branching moiety can be bonded to -COO-, in which a hydrogen atom is excluded from the -COOH of the fourth repeating unit. For example, the -COOH of the fourth repeating unit can react with a compound for forming the branching moiety, so that a hydrogen atom is excluded from the -COOH of the fourth repeating unit, and thus the branching moiety can be bonded to -COO-.

[0257] According to exemplary embodiments, the side branch portion may be represented by the following chemical formula 8.

[0258] [Chemical Formula 8]

[0259]

[0260] In chemical formula 8, Y 3a is an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a hydroxy group, and Y 3bis a direct bond, oxygen (-O-), carbonyl group (-CO-), or carboxyl group (-COO-), and Y 3c It may be an aryl group having 1 to 10 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms.

[0261] In some embodiments, Y 3b may be an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms.

[0262] According to exemplary embodiments, the branching moiety may be derived from one or more of a glycidyl ether compound and a glycidyl ester compound.

[0263] Depending on the type of the compound, the structure of the side branch may vary. For example, if the side branch is derived from a glycidyl ether compound, Y in Chemical Formula 8 3a may be a direct bond. For example, if the side branch is derived from a glycidyl ester compound, Y in Chemical Formula 8 3a may be a carbonyl group (-CO-).

[0264] According to exemplary embodiments, the side branch portion is selected from the group consisting of glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, butyl glycidyl ether, t-butyl glycidyl ether, glycidyl lauryl ether, allyl glycidyl ether, glycidyl phenyl ether, benzyl glycidyl ether, glycidyl 2-methoxyphenyl ether, glycidyl methacrylate, glycidyl acrylate, glycidyl 4-t-butylbenzoate, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, diglycidyl 4-cyclohexene-1,2-dicarboxylate, diglycidyl 1,2-cyclohexanedicarboxylate, 2,2-bis(4-glycidyloxyphenyl)propane and It can be formed from one or more of 1,4-butanediol diglycidyl ethers.

[0265] In some embodiments, the branching portion may be formed from a monoglycidyl ether compound, a glycidyl methacrylate compound, and a glycidyl acrylate compound.

[0266] In some embodiments, the branching moiety can be formed from one or more of glycidyl isopropyl ether, tert-butyl glycidyl ether, ethyl glycidyl ether, glycidyl methacrylate, and glycidyl acrylate.

[0267] In some embodiments, the side branch portion may remain even after the adhesive composition has been cured. Accordingly, laser debonding can be performed under relatively relaxed conditions.

[0268] The number of repetitions of the third repeating unit and the fourth repeating unit can be adjusted to control the molecular weight of the second polymer.

[0269] According to exemplary embodiments, the weight average molecular weight of the second polymer may be from 1,000 to 12,000, from 3,000 to 11,000, from 4,000 to 10,000, from 5,000 to 9,000, or from 6,000 to 8,000.

[0270] In the above range, the chemical resistance of the adhesive composition can be improved.

[0271] According to exemplary embodiments, the molar ratio of the fourth repeating unit to the third repeating unit may be 0.5 to 3, 0.8 to 2, or 1 to 1.8.

[0272] According to exemplary embodiments, the molar ratio of the side branch portion to the third repeating unit may be 0.1 to 2, 0.3 to 1.5, or 0.5 to 1.

[0273] Sufficient curing of the adhesive composition is possible within the above range, so that adhesive properties can be implemented.

[0274] According to exemplary embodiments, by controlling the content ratio of the first polymer and the second polymer, an adhesive composition having improved adhesive properties, laser debonding efficiency, and chemical resistance can be formed.

[0275] According to exemplary embodiments, the weight ratio of the first polymer and the second polymer may be 1:9 to 9:1, 2:8 to 8:2, 2.5:7.5 to 7.5:2.5, 3:7 to 7:3, or 4:6 to 6:4. In this range, adhesive properties, laser debonding efficiency, and chemical resistance may be improved together.

[0276] The coating layer for laser debonding can be decomposed by a laser. For example, when a laser is irradiated onto the coating layer, absorption of laser energy may occur on the surface of the coating layer, thereby causing the coating layer to detach, allowing debonding to be performed with relatively weak force. Alternatively, chemical bond breaking may occur on the interior and surface of the coating layer due to laser energy, thereby causing the coating layer to detach, allowing debonding to be performed without applying physical force.

[0277] According to exemplary embodiments, the coating layer may include a polymer comprising a fifth repeating unit represented by Chemical Formula 9 or Chemical Formula 10.

[0278] [Chemical Formula 9]

[0279]

[0280] [Chemical Formula 10]

[0281]

[0282] In chemical formula 9, X 10 Silver direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R ais an alkyl group having 1 to 5 carbon atoms, which is unsubstituted or substituted with a hydrogen atom or a halogen atom. X 20 Silver direct bond, O, S, NR b Or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R b is an alkyl group having 1 to 5 carbon atoms, which is substituted or unsubstituted with a hydrogen atom or a halogen atom. R 10 , R 20 , R 30 and R 40 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.

[0283] In chemical formula 10, C is arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and X 10, R 10 , R 20 , R 30 and R 40 Each of them is R in chemical formula 9 10 , R 20 , R 30 , R 40 and X 10 of It can be identical to the definition.

[0284] For example, X 10 , R 10 and R 20 Each of the first repeating unit may be derived from X1, R1 and R2 of the chemical formula 1. For example, X 10 , R 10 and R 20 may be identical to X1, R1 and R2 of the chemical formula 1 of the first repeating unit, respectively.

[0285] For example, X 20 , R 30 and R 40 Each of the second repeating unit may be derived from X2, R3 and R4 of the chemical formula 2 or chemical formula 3. For example, X 20 , R 30 and R40 may be identical to X2, R3 and R4 of chemical formula 2 or chemical formula 3 of the second repeating unit, respectively. For example, C may be derived from A of chemical formula 3 of the second repeating unit. For example, C may be identical to A of chemical formula 3 of the second repeating unit.

[0286] The fifth repeating unit may include a ring structure formed by an intramolecular reaction of the -NH- of the first repeating unit and the -C(=O)- of the second repeating unit. For example, it may be bonded to an arylene group of the first repeating unit and form a heterocycle structure including N and O. For example, the ring structure may be formed by heating an adhesive composition including the first repeating unit and the second repeating unit.

[0287] As the above heterocycle structure is formed, laser debonding can be implemented under relatively mild conditions.

[0288] According to exemplary embodiments, the polymer included in the coating layer may include the terminal portion described above. For example, the coating layer may include the terminal portion represented by Chemical Formula 4 or Chemical Formula 5.

[0289] According to exemplary embodiments, the polymer included in the coating layer for laser debonding may include a portion of the first repeating unit or the second repeating unit described above.

[0290] In the polymer according to exemplary embodiments, a part of the first repeating unit and the terminal portion may be bonded. For example, if the first repeating unit is positioned adjacent to the terminal portion of the polymer and includes a part of the -NH- of the first repeating unit that has not undergone an intramolecular reaction with the -C(=O)- of the second repeating unit, the -NH- of the first repeating unit that has not undergone an intramolecular reaction may directly bond to the terminal portion. In this case, an imide bond may be formed through an intramolecular dehydration condensation reaction between a carboxyl group (-C(=O)-) included in the terminal portion directly bonded with the -NH- of the first repeating unit and the -NH- directly bonded to the terminal portion. In this case, the coating layer for laser debonding may include a polymer including a terminal portion represented by the following chemical formula 4a or the following chemical formula 5a.

[0291] [Chemical Formula 4a]

[0292]

[0293] [Chemical Formula 5a]

[0294]

[0295] In chemical formula 4a, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R5 and R6 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms which is unsubstituted or substituted with a halogen atom.

[0296] In chemical formula 5a, R5 and R6 may have the same definitions as R5 and R6 in chemical formula 4a, respectively.

[0297] By controlling the viscosity of the coating solution through the terminal portion included in the above polymer, an optimal coating layer thickness can be achieved.

[0298] In the polymer according to exemplary embodiments, a portion of the second repeating unit may be bonded to the terminal portion. For example, the -NH- of the first repeating unit and the -C(=O)- of the second repeating unit, which have not undergone an intramolecular reaction, may be directly bonded to the terminal portion. For example, the terminal portion may be bonded to an arylene group in the chemical formula 9 or to C in the chemical formula 10.

[0299] According to exemplary embodiments, the polymer included in the coating layer may include a sixth repeating unit represented by chemical formula 11.

[0300] [Chemical Formula 11]

[0301]

[0302] In chemical formula 11, D is a divalent aromatic organic group having 6 to 30 carbon atoms, E is a tetravalent aromatic organic group having 6 to 30 carbon atoms, and R 50 is a substituent containing at least one of a hydroxyl group, an ether group, and an ester group.

[0303] For example, D may be derived from chemical formula 6 of the third repeating unit. For example, D may be identical to D of chemical formula 6 of the third repeating unit.

[0304] For example, E may be derived from the fourth repeating unit. For example, E may be identical to E of Chemical Formula 7 of the fourth repeating unit.

[0305] For example, R 50 may contain hydroxyl groups.

[0306] For example, R 50 It may contain one or more of an ether group (-O-) and an ester group (-C(O)O-).

[0307] According to exemplary embodiments, the R 50 can be represented by the following chemical formula 8.

[0308] [Chemical Formula 8]

[0309]

[0310] In chemical formula 8, Y 3a is an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a hydroxy group, and Y 3b is a direct bond, oxygen (-O-), carbonyl group (-CO-), or carboxyl group (-COO-), and Y 3c It may be an aryl group having 1 to 10 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms.

[0311] In some embodiments, Y 3b may be an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms.

[0312] For example, the sixth repeating unit may include a ring structure formed by an intramolecular reaction of -NH- of the third repeating unit and -COOH of the fourth repeating unit. For example, -NH- of the third repeating unit may combine with -COOH of the adjacent fourth repeating unit to form a heterocycle structure including N and C=O. For example, the ring structure may be formed by heating an adhesive composition including a polymer including the third repeating unit and the fourth repeating unit. The chemical resistance of the adhesive composition may be enhanced by the ring structure.

[0313] In the polymer according to exemplary embodiments, the sixth repeating unit may include the branching moiety described above. For example, the sixth repeating unit may include a portion derived from the fourth repeating unit, and the branching moiety may be bonded to the fourth repeating unit. For example, the branching moiety may be bonded to -COO-, in which hydrogen is removed from -COOH of the portion derived from the fourth repeating unit. Since the branching moiety exists within the polymer included in the coating layer, the laser debonding efficiency may be further improved.

[0314] By controlling the properties of the above coating layer, the laser debonding efficiency can be improved.

[0315] According to exemplary embodiments, the thickness of the coating layer may be 0.2 μm to 2.0 μm.

[0316] In some embodiments, the thickness of the coating layer may be 0.3 μm to 1.7 μm, 0.35 μm to 1.6 μm, 0.4 μm to 1.5 μm, 0.45 μm to 1.4 μm, or 0.5 μm to 1.3 μm.

[0317] In the above range, sufficient adhesive strength can be provided, and decomposition of the polymer by chemicals can be suppressed, thereby improving chemical resistance.

[0318] According to exemplary embodiments, the laser transmittance of the coating layer may be 15% or less.

[0319] In some embodiments, the laser transmittance of the coating layer may be 14.8% or less, 14% or less, 12% or less, 10% or less, 8% or less, or 7% or less.

[0320] The lower limit of the transmittance of the above coating layer is not limited, but may be, for example, 0.001% or more, 0.005% or more, or 0.01% or more.

[0321] The above transmittance can be measured from a known transmittance measuring device and can represent, for example, the transmittance of a laser having a wavelength of 100 nm to 1,000 nm or 100 nm to 700 nm.

[0322] A coating layer having a transmittance within the above range can absorb most (e.g., 90% or more, or 95% or more) of the laser energy. Accordingly, external influences applied to the wafer during the semiconductor packaging process can be reduced.

[0323] According to exemplary embodiments, the adhesion of the coating layer may be 12 mN or more.

[0324] In some embodiments, the adhesive strength of the adhesive film may be 12.5 mN or more, 13 mN or more, 13.5 mN or more, or 14 mN or more.

[0325] In some embodiments, the adhesion of the coating layer may be 30 mN or less, 28 mN or less, 25 mN or less, or 22 mN or less.

[0326] For example, the adhesive strength of the coating layer may be 12 mN to 30 mN, 12.5 mN to 30 mN, 13 mN to 30 mN, 13.5 mN to 28 mN, 14 mN to 25 mN, or 14 mN to 22 mN.

[0327] The above adhesive strength can be measured by a known adhesive strength measuring device and can represent the adhesive strength between the coating layer and other substrates.

[0328] Temporary adhesion between the substrate and wafer can be achieved within the above range. For example, if the thickness is below the above range, the wafer adhesion may deteriorate rapidly, resulting in damage to the wafer. For example, if the thickness exceeds the above range, the debonding process may consume a lot of energy or the circuitry on the wafer may be damaged by the adhesive film.

[0329] According to exemplary embodiments, the coating layer can be decomposed by a laser having an energy per pulse of 180 mJ or less.

[0330] In some embodiments, the coating layer can be decomposed by a laser having an energy per pulse of 175 mJ or less, 172 mJ or less, or 170 mJ or less.

[0331] According to exemplary embodiments, the coating layer can be decomposed by a laser having an energy per pulse of at least 100 mJ, at least 110 mJ, or at least 120 mJ.

[0332] For example, the coating layer can be decomposed by a laser having an energy per pulse of 100 mJ to 180 mJ, 100 mJ to 175 mJ, 110 mJ to 175 mJ, 110 mJ to 172 mJ, or 120 mJ to 170 mJ.

[0333] Within the above range, the energy consumption required for debonding can be minimized. Furthermore, since debonding can be performed with relatively low energy, laser damage to the wafer can be suppressed.

[0334]

[0335] A semiconductor package can be manufactured using an adhesive composition and / or a coating layer containing the above-described polymer.

[0336] Hereinafter, the present invention will be described in detail with reference to the attached drawings. However, these are merely exemplary and the present invention is not limited to the specific embodiments described as examples.

[0337] FIGS. 1 and 2 are schematic diagrams illustrating a portion of a semiconductor package manufacturing method according to exemplary embodiments. For example, FIG. 1 may illustrate a step of attaching a wafer (250) onto a coating layer (100) formed on one surface of a substrate (200). For example, FIG. 2 may illustrate a step of irradiating a laser onto the other surface of the substrate (200).

[0338] Referring to FIG. 1, the above-described coating layer (100) may be formed on one surface of a substrate (200). A wafer (250) may be attached on one surface of the coating layer (100).

[0339] In a method for manufacturing a semiconductor package according to exemplary embodiments, a mixture of an adhesive composition and a solvent according to the above-described embodiments is prepared.

[0340] The solvent may include an organic solvent. For example, the organic solvent may be methyl ethyl ketone, methyl isoamyl ketone, 2-heptanone, ethylene glycol, ethylene glycol dimethyl ether, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, diethylene glycol dimethyl ether, propylene glycol, propylene glycol monoacetate, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), dipropylene glycol, dimethyl phthalate, dibenzyl terephthalate, dibenzyl isophthalate, 1,2-diphenoxyethane, 1,2-bis(4-methylphenoxy)ethane, 1,4-dioxane, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl methoxypropionate, ethyl ethoxypropionate, gamma-butyrolactone, Hexafluoroisopropyl alcohol, etc. may be included. These may be used alone or in combination of two or more.

[0341] The solvent may be included in an amount of 50 wt% to 95 wt% based on the total weight of the adhesive composition. Preferably, the solvent may be included in an amount of 70 wt% to 95 wt%. By including the solvent in the above range, the adhesive composition may have excellent coating properties, viscosity, etc.

[0342] According to exemplary embodiments, the type of the solvent can be adjusted in consideration of the viscosity of the mixture formed by dissolving the adhesive composition.

[0343] For example, the viscosity of the mixture may be from 20 cP to 200 cP, or from 40 cP to 180 cP. For example, when the solvent is gamma-butyrolactone, the viscosity of the mixture may be about 70 cP. For example, when the solvent is dimethylpropionamide, the viscosity of the mixture may be about 40 cP.

[0344] Within the above viscosity range, the thickness of the coating layer can be controlled through coating of the mixture described below.

[0345] According to exemplary embodiments, the adhesive composition may further comprise a surfactant.

[0346] For example, the surfactant may include polyoxyethylene alkyl ethers, polyoxyethylene alkyl ethers, polyethylene glycol diesters, sorbitan fatty esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene imines, and the like. Commercially available surfactants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products Co., Ltd.), MEGAFAC (manufactured by Dainippon Ink & Chemical Co., Ltd.), Flourad (manufactured by Sumitomo 3M Co., Ltd.), Asahi guard, Surflon (all manufactured by Asahi Glass Co., Ltd.), SOLSPERSE (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by EFKA Chemicals Co., Ltd.), or PB 821 (manufactured by Ajinomoto Co., Ltd.). These may be used alone or in combination of two or more.

[0347] In some embodiments, the content of the surfactant may be 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the polymer.

[0348] Within the above range, the applicability and coatability of the resin composition can be improved, and the thickness uniformity and film formation properties of the coating layer can be excellent.

[0349] According to exemplary embodiments, the mixture is coated on one surface of a substrate (200).

[0350] The substrate (200) serves as a carrier wafer and can support the wafer during the semiconductor packaging process, thereby preventing damage that may occur during processing. Furthermore, it can maintain the flatness of the wafer, thereby achieving uniform processability. For example, a silicon carrier wafer, a glass carrier wafer, or the like can be used as the substrate. However, the type, thickness, etc. of the wafer may not be limited.

[0351] The above coating method is not limited, and coating may be performed using, for example, spin coating, slot-die coating, dip coating, slit coating, etc. During coating, the thickness of the coating layer may be adjusted to fall within the above-described range.

[0352] According to exemplary embodiments, the coated mixture can be heated to form a coating layer (100) for laser debonding.

[0353] According to exemplary embodiments, the coated mixture may be soft baked. The solvent contained in the coated mixture may be removed through soft baking.

[0354] According to exemplary embodiments, the soft bake may be performed at a temperature range of 100°C to 150°C, 105°C to 135°C, or 110°C to 130°C.

[0355] According to exemplary embodiments, the soft bake may be performed for 10 seconds to 10 minutes, 30 seconds to 8 minutes, or 1 minute to 6 minutes.

[0356] Rapid soft baking is possible within the above temperature and time range, thereby improving the process efficiency of manufacturing semiconductor packages using a coating layer.

[0357] According to exemplary embodiments, the soft-baked mixture can be post-baked. Post-baking can fix the shape of the coating layer with improved adhesion.

[0358] According to exemplary embodiments, the post-bake may be performed at a temperature range of 250°C to 350°C, 260°C to 330°C, or 270°C to 320°C.

[0359] According to exemplary embodiments, the post-bake may be performed for 30 minutes to 5 hours, 40 minutes to 3 hours, or 50 minutes to 2 hours.

[0360] Within the above temperature and time ranges, a coating layer with enhanced laser energy absorption can be formed. Furthermore, the formation of the coating layer within a relatively short period of time can enhance process efficiency.

[0361] According to exemplary embodiments, a wafer (250) can be attached on the coating layer (100) for laser debonding.

[0362] Although not limited thereto, the wafer (250) may be in an unprocessed state or a processed state. For example, it may be a device wafer having circuits, bumps, etc. formed on the surface of the wafer (250). Any wafer used in the art may be used as the wafer (250) without limitation.

[0363] Attachment of the wafer (250) is not limited, but may be accomplished by physically contacting the wafer (250) with the coating layer (100). The wafer (250) may be fixed by the bonding force between the coating layer (100) and the wafer (250).

[0364] According to exemplary embodiments, the wafer (250) may be processed. Processing may be performed as needed, and any processing method used in the art may be used without limitation.

[0365] Referring to Fig. 2, a laser can be irradiated to the other surface of the substrate (200). The coating layer can be debonded through laser irradiation.

[0366] The other side of the substrate (200) may represent a side on which the coating layer (100) and the wafer (250) are not formed. For example, the laser may be irradiated with the coating layer (100) and the wafer (250) facing downward through flipping.

[0367] Laser irradiation methods and devices may be used without restriction. However, the amount of laser energy irradiated may be controlled.

[0368] According to exemplary embodiments, a laser having a pulse energy of 180 mJ or less may be irradiated. For example, depending on the range described above, a laser having a pulse energy of 100 mJ to 180 mJ, 100 mJ to 175 mJ, 110 mJ to 175 mJ, 110 mJ to 172 mJ, or 120 mJ to 170 mJ may be irradiated.

[0369] Within the above range, the external influence applied to the wafer (250) can be reduced and energy consumption can be reduced.

[0370] Hereinafter, preferred embodiments are presented to help understand the present invention, but these embodiments are only illustrative of the present invention and do not limit the scope of the appended claims. It is obvious to those skilled in the art that various changes and modifications to the embodiments are possible within the scope and technical idea of ​​the present invention, and it is also natural that such changes and modifications fall within the scope of the appended claims.

[0371]

[0372] Example 1

[0373] (1) Preparation of adhesive composition for laser debonding

[0374] Preparation of the first polymer

[0375] A stirrer, temperature controller, and quantitative pump were connected to a four-neck round-bottom flask.

[0376] 2,2-bis(3-amino-4-hydroxyphenyl)propane (compound A-1) and 4,4'-biphenyl dicarbonyl chloride (compound B-1) were added to gamma-butyrolactone (GBL) at a molar ratio of 1:1, and trimethylamine was added. The mixture was reacted at 10°C for 6 hours with a solid content of 20 wt%.

[0377] After the reaction, phthalic anhydride (compound C-1) was added at 0.1 mol per 1 mol of 4,4'-biphenyl dicarbonyl chloride. Afterwards, the reaction was carried out by stirring at 50°C for 10 hours.

[0378] The product was added dropwise to water to precipitate, and the solvent was removed through a filter to obtain a wet cake. The wet cake was precipitated in water and stirred for 4 hours. The solvent was removed through a filter to obtain a wet cake. The above process was repeated 2-3 times to remove impurities, and the first polymer was obtained. (Weight average molecular weight: approximately 20,000)

[0379]

[0380] Manufacturing of a second polymer

[0381] In a four-necked round-bottomed flask, 4,4'-oxydianiline (compound A-4) and 4,4'-biphthalic anhydride (compound D-1) were added at a molar ratio of 1:1 using GBL as a solvent, and the mixture was reacted at 10°C for 24 hours with a solid content of 20 wt%. Thereafter, water was added at 0.1 mol per 1 mol of 4,4'-biphthalic anhydride, and the mixture was reacted at 50°C for 24 hours.

[0382] Afterwards, 0.1 mol of glycidyl isopropyl ether (compound E-1) was added to 1 mol of 4,4'-biphthalic anhydride and reacted at 50°C for 48 hours to produce a second polymer (weight average molecular weight of approximately 8,000).

[0383] Preparation of adhesive composition for laser debonding

[0384] An adhesive composition for laser debonding was prepared by mixing 4.5 wt% of the first polymer, 10.5 wt% of the second polymer, 1 ppm of the surfactant SH-8400 (Dow), and the remainder of gamma-butyrolactone.

[0385]

[0386] Examples 2 to 9

[0387] An adhesive composition for laser debonding was prepared in the same manner as in Example 1, except that the compounds used were changed according to Table 1 below. The molar ratio between the compounds was maintained in Examples 2 to 9.

[0388] Examples 10 to 13

[0389] An adhesive composition for laser debonding was prepared according to the same method as Example 1, except that the weight ratios of the first polymer and the second polymer were changed to 1:9, 5:5, 7:3, and 9:1, respectively.

[0390] Comparative Examples 1 to 6

[0391] An adhesive composition was prepared using the compounds shown in Table 1 below in the same manner as in Example 1, except that only the first polymer or only the second polymer was used. The molar ratio between the compounds was maintained in Comparative Examples 1 to 6.

[0392] Classification 1 Polymer Class 2 Polymer Compound A Compound B Compound C Compound A Compound D Compound E Example 1A-1B-1C-1A-4D-1E-1 Example 2A-2B-2C-2A-4D-1E-1 Example 3A-2B-3C-3A-4D-1E-1 Example 4A-1B-1C-1A-5D-2E-2 Example 5A-1B-1C-1A-6D-3E-3 Example 6A-1B-1C-1A-7D-1E-1 Example 7A-1B-1C-1A-8D-1E-1 Example 8A-1B-1C-1A-4D-4E-1 Example 9A-1B-1C-1A-4D-5E-1 Example 10A-1B-1C-1A-4D-1E-1Example 11A-1B-1C-1A-4D-1E-1Example 12A-1B-1C-1A-4D-1E-1Example 13A-1B-1C-1A-4D-1E-1Comparative Example 1A-1B-1C-1---Comparative Example 2A-2B-2C-2---Comparative Example 3A-3B-3C-3---Comparative Example 4---A-4D-1E-1Comparative Example 5---A-5D-2E-2Comparative Example 6---A-6D-3E-3

[0393] Each compound in Table 1 above is as follows.

[0394] Compound A

[0395] Compound A-1: ​​2,2-bis(3-amino-4-hydroxylphenyl)propane

[0396]

[0397] Compound A-2: 3,3′-dihydroxy-4,4′-diaminobiphenyl

[0398]

[0399] Compound A-3: 4,4'-(hexafluoroisopropylidene)bis(2-aminophenol)

[0400]

[0401] Compound A-4: 4,4'-oxydianiline

[0402]

[0403] Compound A-5: 4,4'-diaminodiphenylmethane

[0404]

[0405] Compound A-6: 2,2-bis(trifluoromethyl)benzidine

[0406]

[0407] Compound A-7: 1,4-phenylenediamine

[0408]

[0409] Compound A-8: 1,3-phenylenediamine

[0410]

[0411] Compound B

[0412] Compound B-1: 4,4'-biphenyl dicarbonyl chloride

[0413]

[0414] Compound B-2: terephthaloyl chloride

[0415]

[0416] Compound B-3: 4,4'-oxydibenzoyl chloride

[0417]

[0418] Compound C

[0419] Compound C-1: phthalic anhydride

[0420]

[0421] Compound C-2: cis-5-norbornene-endo-2,3-dicarboxylic anhydride

[0422]

[0423] Compound C-3: methyl-5-norbornene-2,3-dicarboxylic anhydride

[0424]

[0425]

[0426] Compound D

[0427] Compound D-1: 4,4'-biphthalic anhydride

[0428]

[0429] Compound D-2: 2,2-bis(3,4-anhydrodicarboxyphenyl) hexafluoropropane

[0430]

[0431] Compound D-3: 4,4'-oxydiphthalic anhydride

[0432]

[0433] Compound D-4: 3,3',4,4'-benzophenone tetracarboxylic dianhydride

[0434]

[0435] Compound D-5: Pyromellitic dianhydride

[0436]

[0437] Compound E

[0438] Compound E-1: glycidyl isopropyl ether

[0439]

[0440] Compound E-2: tert-butyl glycidyl ether

[0441]

[0442] Compound E-3: ethyl glycidyl ether

[0443]

[0444]

[0445] Experimental example

[0446] The adhesive composition for laser debonding according to the examples or the adhesive composition according to the comparative examples was coated on a substrate. Thereafter, the adhesive composition was soft baked at 120°C for 240 seconds and post-baked at 280°C for 1 hour to harden. (Thickness: approximately 0.6 μm)

[0447] (1) Adhesion measurement

[0448] The adhesion of the coating layer was measured under the following conditions using an adhesion measuring device (nano scratch).

[0449] - Scratch length: 2mm

[0450] - Scratch speed: 2mm / min

[0451] - Tip: 10 ㎛ radius Diamond

[0452] - Loading rate: 49 mN / min

[0453] - Load: 1~50 mN

[0454] (2) Transmittance measurement

[0455] The transmittance of the coating layer was measured by irradiating a laser onto the coating formed on the substrate using an ellipsometer.

[0456] (3) Laser debonding measurement

[0457] An excimer laser (XeCl excimer UV laser, wavelength 308 nm, 600 mJ@50 Hz) was used to irradiate the coating formed on the substrate. The minimum laser energy at which the coating layer was debonded was measured by outputting the 308 nm laser from 110 mJ to 250 mJ.

[0458] (4) Measurement of chemical resistance

[0459] The change in thickness before and after the substrate on which the coating was formed was immersed in 5% potassium hydroxide (KOH) was measured using alpha-step.

[0460] The measurement results of the above experimental examples are shown in Table 2.

[0461] Adhesion (mN) Transmittance (%) Minimum Laser Energy (mJ) Chemical Resistance (%) Example 1 15.25.115099.96 Example 2 14.75.916099.77 Example 3 15.55.415099.94 Example 4 15.35.815099.73 Example 5 15.85.115099.98 Example 6 14.26.816099.54 Example 7 13.96.616099.48 Example 8 15.25.515099.69 Example 9 14.95.915099.62 Example 10 10.119.118099.41 Example 1115.94.115096.80Example 1216.12.714095.38Example 1317.50.813094.21Comparative Example 118.20.0213093.83Comparative Example 217.10.0714090.10Comparative Example 318.50.0513093.20Comparative Example 49.620.4180100.0Comparative Example 59.920.8180100.0Comparative Example 610.521180100.0

[0462] When the adhesive composition for laser debonding according to the examples was used, laser debonding was possible with low energy consumption, and chemical resistance, adhesion, and transmission properties were improved together. In Example 10, where the weight ratio of the first polymer to the second polymer was relatively low, the adhesion and transmission properties were relatively reduced, and the energy consumption was relatively increased.

[0463] When the adhesive compositions according to Comparative Examples 1 to 3 were used, chemical resistance was reduced. When the adhesive compositions according to Comparative Examples 4 to 6 were used, adhesive strength was reduced and energy consumption was increased.

Claims

1. A first polymer comprising a first repeating unit represented by Chemical Formula 1; and a second repeating unit comprising an acyl group; and An adhesive composition for laser debonding, comprising a second polymer comprising a third repeating unit represented by chemical formula 6; and a fourth repeating unit comprising an acyl group: [Chemical Formula 1] [Chemical Formula 6] (In chemical formula 1, X1 is a direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R a is a hydrogen atom, or an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R1 and R2 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms, In chemical formula 6, D is a divalent organic group having 6 to 30 carbon atoms.

2. An adhesive composition for laser debonding, wherein the second repeating unit in claim 1 comprises a repeating unit represented by chemical formula 2 or chemical formula 3: [Chemical Formula 2] [Chemical Formula 3] (In chemical formula 2, X2 is a direct bond, O, S, NR b , N=N or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R b is an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a hydrogen atom or a halogen atom, and R3 and R4 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms, In chemical formula 3, A is arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R3 and R4 are the same as defined above.

3. In claim 1, the first polymer further includes a terminal portion, An adhesive composition for laser debonding, wherein the terminal portion is bonded to at least one of the first repeating unit and the second repeating unit and includes a carboxyl group.

4. In claim 3, the terminal portion is an adhesive composition for laser debonding represented by chemical formula 4 or chemical formula 5: [Chemical Formula 4] [Chemical Formula 5] (In the chemical formula 4, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R5 and R6 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, In chemical formula 5, R5 and R6 are the same as defined above.

5. In claim 1, the first repeating unit is formed from at least one of the compounds represented by the following chemical formulas 1-1 to 1-3, an adhesive composition for laser debonding: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] .

6. In claim 1, the second repeating unit is formed from at least one of the compounds represented by the following chemical formulae 2-1 to 2-3 and the compounds represented by the following chemical formulae 3-1 to 3-2, an adhesive composition for laser debonding: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 3-1] [Chemical Formula 3-2] .

7. In claim 3, the terminal portion is formed from at least one of the compounds represented by the following chemical formulas 4-1 to 4-6 and the compound represented by the following chemical formula 5-1, an adhesive composition for laser debonding: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6] [Chemical Formula 5-1] .

8. In claim 1, the fourth repeating unit comprises a repeating unit represented by the following chemical formula 7, an adhesive composition for laser debonding: [Chemical Formula 7] (In chemical formula 7, E is a tetravalent organic group having 6 to 30 carbon atoms).

9. In claim 1, the second polymer further includes a side branch portion, An adhesive composition for laser debonding, wherein the side branch portion is bonded to the fourth repeating unit and includes at least one of an ether group and an ester group.

10. An adhesive composition for laser debonding, wherein the side branch portion is derived from at least one of a glycidyl ether compound and a glycidyl ester compound in claim 9.

11. In claim 1, the third repeating unit is formed from at least one of the compounds represented by the following chemical formulas 6-1 to 6-5, an adhesive composition for laser debonding: [Chemical Formula 6-1] [Chemical Formula 6-2] [Chemical Formula 6-3] [Chemical Formula 6-4] [Chemical Formula 6-5] .

12. In claim 1, the fourth repeating unit is formed from at least one of the compounds represented by the following chemical formulae 7-1 to 7-5, an adhesive composition for laser debonding: [Chemical Formula 7-1] [Chemical Formula 7-2] [Chemical Formula 7-3] [Chemical Formula 7-4] [Chemical Formula 7-5] .

13. In claim 9, the side branch portion is selected from the group consisting of glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, butyl glycidyl ether, t-butyl glycidyl ether, glycidyl lauryl ether, allyl glycidyl ether, glycidyl phenyl ether, benzyl glycidyl ether, glycidyl 2-methoxyphenyl ether, glycidyl methacrylate, glycidyl acrylate, glycidyl 4-t-butylbenzoate, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, diglycidyl 4-cyclohexene-1,2-dicarboxylate, diglycidyl 1,2-cyclohexanedicarboxylate, An adhesive composition for laser debonding, formed from at least one of 2,2-bis(4-glycidyloxyphenyl)propane and 1,4-butanediol diglycidyl ether.

14. An adhesive composition for laser debonding according to claim 1, wherein the weight ratio of the first polymer and the second polymer is 1:9 to 9:

1.

15. A coating layer for laser debonding, comprising a polymer comprising a fifth repeating unit represented by Chemical Formula 9 or Chemical Formula 10; and a sixth repeating unit represented by Chemical Formula 11: [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] (In chemical formula 9, X 10 Silver direct bond, O, S, NR a Or an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen atom, and R a is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and X 20 Silver direct bond, O, S, NR b Or an alkylene group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R b is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, and R 10 , R 20 , R 30 and R 40 are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms, In chemical formula 10, C is arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and X 10, R 10 , R 20 , R 30 and R 40 is the same as the above definition, In chemical formula 11, D is a divalent organic group having 6 to 30 carbon atoms, E is a tetravalent organic group having 6 to 30 carbon atoms, and R 50 is a substituent containing at least one of a hydroxyl group, an ether group, and an ester group.

16. A coating layer for laser debonding, comprising a polymer further comprising at least one selected from the group consisting of terminal portions represented by Chemical Formula 4, Chemical Formula 4a, Chemical Formula 5, and Chemical Formula 5a in claim 15: [Chemical Formula 4] [Chemical Formula 4a] [Chemical Formula 5] [Chemical Formula 5a] (In Chemical Formula 4 and Chemical Formula 4a, B is cycloalkylene having 5 to 7 carbon atoms, cycloalkenylene having 5 to 7 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 6 to 10 carbon atoms, and R5 and R6 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, or an alkenyl group having 1 to 5 carbon atoms substituted or unsubstituted with a halogen atom, In Chemical Formula 5 and Chemical Formula 5a, R5 and R6 are the same as defined above.

17. A coating layer for laser debonding having a thickness of 0.2 µm to 2.0 µm according to claim 15.

18. A coating layer for laser debonding, having a laser transmittance of 15% or less, according to claim 15.

19. A coating layer for laser debonding having an adhesive strength of 12 mN or more according to claim 15.

20. A coating layer for laser debonding, which is decomposed by a laser having a pulse energy of 180 mJ or less in claim 15.

21. A step of preparing a mixture of an adhesive composition for laser debonding and a solvent according to claim 1; A step of coating the mixture on one side of a substrate; A step of heating the coated mixture to form a coating layer for laser debonding; A step of attaching a wafer on the coating layer for laser debonding; a step of processing the wafer; and A method for manufacturing a semiconductor package, comprising a step of irradiating a laser onto the other surface of the substrate.

22. In claim 21, the step of heating the coated mixture to form a coating layer for laser debonding is as follows: A soft baking step at 100℃ to 150℃; and A method for manufacturing a semiconductor package, comprising a step of post-baking at 250°C to 350°C.

23. A method for manufacturing a semiconductor package according to claim 21, wherein the step of irradiating the laser irradiates the laser with an energy per pulse of 180 mJ or less.

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