Photosensitive resin composition, photosensitive resin layer, and semiconductor device using same

Abstract

The present invention provides a photosensitive resin composition, a photosensitive resin layer manufactured using the same, and a semiconductor device comprising the same, the photosensitive resin composition comprising (A) at least one resin selected from the group consisting of polyimide precursors and polybenzoxazole precursors; (B) a photopolymerizable compound; (C) a photoinitiator represented by Chemical Formula 1; and (D) a solvent. (In Chemical Formula 1, each substituent is as defined in the specification. ) [Chemical Formula 1]

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0037080 filed on March 18, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a photosensitive resin composition, a photosensitive resin layer using the same, and a semiconductor device. Background Art

[0004] In order to protect semiconductor devices from external environmental influences such as moisture or mechanical shock, a method of sealing semiconductor devices with an epoxy resin composition is being commercially practiced. Semiconductor device sealing has traditionally been achieved by cutting (dicing) wafers to manufacture semiconductor chips and then encapsulating the semiconductor chip units. However, a process has recently been developed that first encapsulates the semiconductor chips in a wafer state or panel state that is larger than the semiconductor chip, and then cuts (dices) the package into semiconductor chips. In general, the former method is called chip scale packaging (CSP), and the latter process is called wafer level packaging (WLP) and panel level packaging (PLP).

[0005] Wafer-level packaging (WLP) has the advantages of a higher process yield (yield) than chip scale packaging (CSP) and a smaller semiconductor installation space due to its thin package thickness. However, wafer-level packaging (WLP) or panel-level packaging (PLP) has a larger film forming area than chip scale packaging (CSP) that seals a single chip, so there is a problem of significant warping due to the difference in thermal expansion coefficient between the chip or panel and the sealing material. Warping (if it ever occurs) may affect the yield and chip handling in subsequent processes. In addition, wafer-level packaging (WLP) or panel-level packaging (PLP) currently uses liquid epoxy resin or silicone resin as the main sealant, but since the resin after sealing also uses liquid single molecules, there is a problem of low inorganic filler content in the liquid composition and low reliability of the semiconductor package after sealing.

[0006] Therefore, there is a need to develop an insulating layer for a redistribution layer (RDL) that can achieve small warpage and have excellent reliability even when wafer-level packaging (WLP) or panel-level packaging (PLP) is applied.

[0007] To meet these requirements, photosensitive resin compositions are being developed for forming insulating layers for redistribution layers. Typically, photosensitive polyimide resin compositions that impart photosensitivity to the polyimide resin itself are primarily used. Photosensitive polyimide resin compositions can simplify the patterning process. However, existing photosensitive polyimide resin compositions for forming insulating layers (cured layers) for redistribution layers suffer from poor corrosion resistance and chemical resistance.

[0008] When the photosensitive resin composition is used for the passivation layer of the semiconductor circuit, polyimide (PI) or polybenzoxazole (PBO) resin is used as a key component to ensure elongation, which is important for reliability and film properties such as glass transition temperature (Tg). Therefore, the photosensitive resin composition comprising the above resin needs to be used with other photocrosslinkable monomers, photopolymerization initiators, etc. to ensure excellent passivation layer properties, but still needs to be free of residue to achieve excellent patterns, excellent sensitivity characteristics and storage stability of more than two weeks at room temperature. In addition, with the miniaturization and functionalization of electronic devices, resin films also need high resolution, thereby requiring a resin composition capable of forming various pattern shapes. In order to cope with high resolution, various schemes for the photopolymerization initiator included in the resin composition have also been proposed, in which a highly sensitive photoinitiator is used.

[0009] However, high-sensitivity photoinitiators, whose small addition differences can affect pattern shape, have the disadvantages of being difficult to control and having a narrow exposure margin. Furthermore, as the thickness of the resin film increases, there may be differences in the photocurability of the upper and lower portions of the film, where appropriate critical dimensions (CDs) can be formed, but the lower portion of the film is penetrated by the developer, leading to problems such as pattern lifting or reverse taper. Summary of the Invention

[0010] Some exemplary embodiments provide a photosensitive resin composition having excellent controllability, which can easily control pattern formation and can be achieved at high resolution by using a photoinitiator having a specific structure.

[0011] Some exemplary embodiments provide a photosensitive resin layer manufactured using the photosensitive resin composition.

[0012] Some example embodiments provide a semiconductor device including a photosensitive resin layer.

[0013] Some exemplary embodiments provide a photosensitive resin composition including (A) at least one resin selected from a polyimide precursor and a polybenzoxazole precursor; (B) a photopolymerizable compound; (C) a photoinitiator represented by Chemical Formula 1; and (D) a solvent.

[0014] [Chemical Formula 1]

[0015]

[0016] In Chemical Formula 1,

[0017] R 1 to R 3 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 aryl, provided that R 1 to R 3 Not all hydrogen atoms.

[0018] R 1 and R 3 Can be the same as each other.

[0019] R 1 and R 3 Each independently may be a substituted or unsubstituted C6 to C20 aryl group.

[0020] R 2 It may be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C3 to C20 cycloalkyl group.

[0021] Chemical Formula 1 may include at least one selected from the group consisting of compounds represented by Chemical Formula 1-1 to Chemical Formula 1-3.

[0022] [Chemical Formula 1-1]

[0023]

[0024] [Chemical formula 1-2]

[0025]

[0026] [Chemical formula 1-3]

[0027]

[0028] The photoinitiator represented by Chemical Formula 1 may be included in an amount of about 1 part by weight to about 5 parts by weight based on 100 parts by weight of the photosensitive resin composition.

[0029] The photosensitive resin composition may further include a photosensitizer.

[0030] The content of the photosensitizer may be less than that of the photoinitiator represented by Chemical Formula 1.

[0031] The photosensitive resin composition further includes an antioxidant, and the content of the antioxidant may be less than that of the photosensitizer.

[0032] The photosensitive resin composition may include about 20 parts by weight to about 40 parts by weight of a resin, about 1 part by weight to about 10 parts by weight of a photopolymerizable compound, about 1 part by weight to about 5 parts by weight of a photoinitiator, and about 40 parts by weight to about 80 parts by weight of a solvent, based on 100 parts by weight of the photosensitive resin composition.

[0033] The photosensitive resin composition may further include additives such as diacid, alkanolamine, leveling agent, silane coupling agent, surfactant, epoxy compound, thermal latent acid generator, or a combination thereof.

[0034] The photosensitive resin composition may be a negative photosensitive resin composition.

[0035] Some exemplary embodiments provide a photosensitive resin layer manufactured using the photosensitive resin composition.

[0036] The photosensitive resin layer may be a semiconductor redistribution layer insulating layer.

[0037] Some example embodiments provide a semiconductor device including a photosensitive resin layer.

[0038] Other embodiments of the invention are included in the detailed description below.

[0039] The photosensitive resin composition according to some exemplary embodiments includes a photoinitiator having a specific structure, so that pattern formation can be easily controlled and a high-resolution pattern can be achieved. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Example 1.

[0041] Figure 2 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Example 2.

[0042] Figure 3 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Example 3.

[0043] Figure 4 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Example 4.

[0044] Figure 5 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Comparative Example 1.

[0045] Figure 6 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Comparative Example 2.

[0046] Figure 7 This is a focused ion beam (FIB) image of a cross section of a cured layer prepared by curing the photosensitive resin composition of Comparative Example 3. DETAILED DESCRIPTION

[0047] Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary and the present invention is not limited thereto, but is defined by the scope of the claims.

[0048] As used herein, when specific definitions are not otherwise provided, “alkyl” refers to a C1 to C20 alkyl group, “alkenyl” refers to a C2 to C20 alkenyl group, “cycloalkenyl” refers to a C3 to C20 cycloalkenyl group, “heterocycloalkenyl” refers to a C3 to C20 heterocycloalkenyl group, “aryl” refers to a C6 to C20 aryl group, “aralkyl” refers to a C7 to C20 aralkyl group, “alkylene” refers to a C6 to C20 alkylene group, “arylene” refers to a C6 to C20 arylene group, “alkylarylene” refers to a C7 to C20 alkylarylene group, “heteroarylene” refers to a C3 to C20 heteroarylene group, and “alkyleneoxy” refers to a C1 to C20 alkyleneoxy group.

[0049] As used herein, when no specific definition is provided otherwise, "substituted" means that at least one hydrogen of the compound is selected from a halogen atom (F, Cl, Br or I), a C1 to C20 alkyl group substituted by a halogen atom such as a trifluoromethyl group, a hydroxyl group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, group), a carbonyl group, a carbamyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C20 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, a C2 to C20 heterocycloalkynyl group, a C3 to C20 heteroaryl group, or a combination thereof.

[0050] As used herein, when no specific definition is otherwise provided, "hetero" refers to at least one heteroatom including N, O, S and P in a chemical formula.

[0051] As used herein, when no specific definition is otherwise provided, "(meth)acrylate" refers to both "acrylate" and "methacrylate".

[0052] As used herein, when no other definition is provided, the term "combination" refers to mixing or copolymerization. In addition, "copolymerization" refers to block copolymerization, alternating copolymerization or random copolymerization, and "copolymer" refers to block copolymer, alternating copolymer or random copolymer.

[0053] As used herein, when no specific definition is otherwise provided, an unsaturated bond includes not only multiple bonds between carbon atoms but also those containing other molecules, such as a carbonyl bond and an azo bond.

[0054] In the chemical formulae in this specification, unless specifically defined otherwise, hydrogen is bonded to positions where no chemical bond is drawn.

[0055] As used herein, when no definition is otherwise provided, "*" refers to a connecting moiety between the same or different atoms or chemical formulas.

[0056] The photosensitive resin composition according to some embodiments includes (A) at least one resin selected from a polyimide precursor and a polybenzoxazole precursor; (B) a photopolymerizable compound; (C) a photoinitiator represented by Chemical Formula 1; and (D) a solvent.

[0057] [Chemical Formula 1]

[0058]

[0059] In Chemical Formula 1,

[0060] R 1 to R 3 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 aryl, provided that R 1 to R 3 Not all hydrogen atoms.

[0061] Hereinafter, each component will be described in detail.

[0062] (A) Resin

[0063] The resin used in the photosensitive resin composition according to some exemplary embodiments may be a polyamic acid or polyamide ester-based resin, and the polyamic acid or polyamide ester-based resin may include a structural unit represented by Chemical Formula 2.

[0064] [Chemical Formula 2]

[0065]

[0066] In Chemical Formula 2,

[0067] X 1 is a moiety derived from a dianhydride monomer,

[0068] Y 1 is a moiety derived from a diamine monomer, and

[0069] R 4 and R 5 Each is independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclyl group.

[0070] For example, R 4 and R 5 Each may independently be a C1 to C20 alkyl group which may be substituted or unsubstituted by a (meth)acrylate group at the terminal, a C3 to C20 cycloalkyl group which may be substituted or unsubstituted by a (meth)acrylate group at the terminal, a C6 to C20 aryl group which may be substituted or unsubstituted by a (meth)acrylate group at the terminal, or a C2 to C20 heterocyclic group which may be substituted or unsubstituted by a (meth)acrylate group at the terminal.

[0071] The polyamic acid or polyamide ester resin including the structural unit represented by Chemical Formula 2 can be used together with the photoinitiator represented by Chemical Formula 1, so that the heat resistance stability of the photosensitive resin composition according to some exemplary embodiments can be very easily improved. In addition, by applying it to a negative composition, the developability can be easily greatly improved.

[0072] Generally, a photosensitive resin composition including a resin having a closed ring structure has a problem of rapid gelation under harsh conditions, but a photosensitive resin composition according to some exemplary embodiments, including a polyamic acid or polyamide ester resin including a structural unit represented by Chemical Formula 2 and a photoinitiator represented by Chemical Formula 1, can be very slowly gelated even under harsh conditions and has excellent heat resistance stability.

[0073] For example, the polyamic acid or polyamide ester-based resin including the structural unit represented by Chemical Formula 2 may be a polymer between a dianhydride monomer and a diamine monomer.

[0074] For example, the diamine monomer may be represented by Chemical Formula 2-2 or Chemical Formula 2-3.

[0075] [Chemical Formula 2-2]

[0076]

[0077] [Chemical formula 2-3]

[0078]

[0079] In Chemical Formula 2-2 and Chemical Formula 2-3,

[0080] R 6 and R 7 are each independently a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group, and

[0081] n1 and n2 are each independently an integer from 0 to 4.

[0082] For example, the dianhydride monomer may include a monomer represented by Chemical Formula 2-1, but is not necessarily limited thereto.

[0083] [Chemical Formula 2-1]

[0084]

[0085] In Chemical Formula 2-1,

[0086] L 2 is a single bond, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, *-NR0 -*(where R 0 is a substituted or unsubstituted C1 to C10 alkyl), a substituted or unsubstituted C1 to C20 alkylene, a substituted or unsubstituted C6 to C20 arylene, a substituted or unsubstituted C2 to C20 heterocyclic linking group, or a combination thereof.

[0087] For example, when L 2 When L is a substituted or unsubstituted C1 to C20 alkylene group, 2 The trifluoroalkyl group may be substituted or unsubstituted C1 to C20 alkylene group.

[0088] The weight average molecular weight (Mw) of the polyamic acid or polyamide ester resin can be about 3,000 g / mol to about 300,000 g / mol. If the weight average molecular weight of the polyamic acid or polyamide ester resin is within the above range, sufficient physical properties can be obtained, and the solubility in organic solvents is improved, making it easy to handle.

[0089] The resin may be included in an amount of about 20 to about 40 parts by weight, for example, about 25 to about 35 parts by weight, based on 100 parts by weight of the photosensitive resin composition.

[0090] The resin used in the photosensitive resin composition according to one or more embodiments may be a polybenzoxazole-based resin.

[0091] The polybenzoxazole-based resin may include a structural unit represented by Chemical Formula 41, and the polyimide precursor may include a structural unit represented by Chemical Formula 51.

[0092] [Chemical Formula 41]

[0093]

[0094] In Chemical Formula 41,

[0095] X 11 and X 21 are each independently a substituted or unsubstituted tetravalent C6 to C30 aromatic organic group,

[0096] Y 11 and Y 21 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic organic group, and

[0097] m1 is an integer from 2 to 1000, m2 is an integer from 0 to 500, and m1 / (m1+m2)>0.5.

[0098] [Chemical Formula 51]

[0099]

[0100] In Chemical Formula 51,

[0101] X 3 is a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted divalent C3 to C30 alicyclic organic group, and

[0102] Y 3 is a substituted or unsubstituted tetravalent C6 to C30 aromatic organic group, a substituted or unsubstituted tetravalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted tetravalent C3 to C30 alicyclic organic group.

[0103] In Chemical Formula 41, X 1 It may be an aromatic organic group, and may be a moiety derived from an aromatic diamine.

[0104] Examples of aromatic diamines may be selected from 3,3′-diamino-4,4′-dihydroxybiphenyl, 4,4′-diamino-3,3′-dihydroxybiphenyl, bis(3-amino-4-hydroxyphenyl)propane, bis(4-amino-3-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(4-amino-3-hydroxyphenyl)sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-amino-3-hydroxyphenyl)-1,1, 1,3,3,3-Hexafluoropropane, 2,2-bis(3-amino-4-hydroxy-5-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(3-amino-4-hydroxy-6-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(3-amino-4-hydroxy-2-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(4-amino-3-hydroxy-5-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(4-amino-3-hydroxy-6-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(4-amino-3-hydroxy -2-trifluoromethylphenyl)hexafluoropropane, 2,2-bis(3-amino-4-hydroxy-5-pentafluoroethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2-(3-amino-4-hydroxy-5-pentafluoroethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane, At least one of 2-(3-amino-6-trifluoromethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-5-trifluoromethylphenyl)-2-(3-hydroxy-4-amino-2-trifluoromethylphenyl)hexafluoropropane, 2-(3-amino-4-hydroxy-2-trifluoromethylphenyl)-2-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane and 2-(3-amino-4-hydroxy-6-trifluoromethylphenyl)-2-(3-hydroxy-4-amino-5-trifluoromethylphenyl)hexafluoropropane, but is not limited thereto.

[0105] X 11 and X 21 Examples of may be the functional group represented by Chemical Formula 61 or Chemical Formula 71, but are not limited thereto.

[0106] [Chemical Formula 61]

[0107]

[0108] [Chemical Formula 71]

[0109]

[0110] In Chemical Formula 61 and Chemical Formula 71,

[0111] A 1 It is a single bond, O, CO, CR 47 R 48 , SO2 or S, where R 47 and R 48 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, specifically a C1 to C30 fluoroalkyl group,

[0112] R 50 to R 52 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 carboxyl group, a hydroxyl group or a thiol group, and,

[0113] n10 is an integer from 0 to 2, provided that n11 and n12 are each independently an integer from 0 to 3.

[0114] In Chemical Formula 41, Y 11 and Y 21 Each of Y and Y can be independently a divalent aromatic organic group, a divalent aliphatic organic group or a divalent alicyclic organic group, and can be part of a dicarboxylic acid or a dicarboxylic acid derivative. 11 and Y 21 Each independently may be a divalent aromatic organic group or a divalent alicyclic organic group.

[0115] Specific examples of the dicarboxylic acid derivative may include 4,4'-oxydibenzoylchloride, diphenyloxydicarbonyl dichloride, bis(phenylcarbonylchloride)sulfone, bis(phenylcarbonylchloride)ether, bis(phenylcarbonylchloride)phenone, phthaloyl dichloride, terephthaloyldichloride, isophthaloyl dichloride, dicarbonyldichloride, diphenyloxydicarboxylatedibenzotriazole, or a combination thereof, but are not limited thereto.

[0116] Y 11 and Y 21Examples of may be the functional groups represented by Chemical Formula 81 to Chemical Formula 100, but are not limited thereto.

[0117] [Chemical Formula 81]

[0118]

[0119] [Chemical Formula 91]

[0120]

[0121] [Chemical Formula 100]

[0122]

[0123] In Chemical Formulas 81 to 100,

[0124] R 53 to R 56 are each independently a substituted or unsubstituted C1 to C30 alkyl group,

[0125] n13 and n14 are each independently an integer from 0 to 4, n15 and n16 are each independently an integer from 0 to 3, and

[0126] A 2 For single bond, O, CR 47 R 48 , CO, CONH, S or SO2, where R 47 and R 48 Each is independently a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, specifically a C1 to C30 fluoroalkyl group.

[0127] In Chemical Formula 51, X 3 is a divalent aromatic organic group, a divalent aliphatic organic group or a divalent alicyclic organic group. 3 is a divalent aromatic organic group or a divalent alicyclic organic group.

[0128] Specifically, X 3 It may be a portion derived from an aromatic diamine, an alicyclic diamine, or a silicon diamine. Here, the aromatic diamine, the alicyclic diamine, and the silicon diamine may be used alone or in combination of one or more.

[0129] Examples of the aromatic diamine may include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfide, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis[4-(4-aminophenoxy)phenyl]sulfone, bis(3-aminophenoxyphenyl)sulfone, bis(4-aminophenoxy)biphenyl, bis[4-(4-aminophenoxy)phenyl]ether, 1,4-bis(4-aminophenoxy)benzene, compounds including those in which the aromatic ring is substituted by an alkyl group or a halogen group, or combinations thereof, but are not limited thereto.

[0130] Examples of the alicyclic diamine may be 1,2-cyclohexyldiamine, 1,3-cyclohexyldiamine, or a combination thereof, but are not limited thereto.

[0131] Examples of silicon diamines may be bis(4-aminophenyl)dimethylsilane, bis(4-aminophenyl)tetramethylsiloxane, bis(p-aminophenyl)tetramethyldisiloxane, bis(γ-aminopropyl)tetramethyldisiloxane, 1,4-bis(γ-aminopropyldimethylsilyl)benzene, bis(4-aminobutyl)tetramethyldisiloxane, bis(γ-aminopropyl)tetraphenyldisiloxane, 1,3-bis(aminopropyl)tetramethyldisiloxane, or a combination thereof, but are not limited thereto.

[0132] In Chemical Formula 51, Y 3 is a tetravalent aromatic organic group, a tetravalent aliphatic organic group or a tetravalent alicyclic organic group. 3 is a tetravalent aromatic organic group or a tetravalent alicyclic organic group.

[0133] Y 3 It may be a portion derived from an aromatic dianhydride or an alicyclic dianhydride. Here, the aromatic dianhydride and the alicyclic dianhydride may be used alone or in combination of one or more.

[0134] Examples of aromatic acid dianhydrides include benzophenone tetracarboxylic dianhydride, such as pyromellitic dianhydride; benzophenone-3,3',4,4'-tetracarboxylic dianhydride; oxydiphthalic dianhydride, such as 4,4'-oxydiphthalic dianhydride; biphthalic dianhydride, such as 3,3',4,4'-biphthalic dianhydride; (hexafluoroisopropyledene) diphthalic dianhydride, such as 4,4'-(hexafluoroisopropyledene) diphthalic dianhydride; and dianhydride); naphthalene-1,4,5,8-tetracarboxylic dianhydride; 3,4,9,10-perylenetetracarboxylic dianhydride, etc., but not limited thereto.

[0135] Examples of the alicyclic acid dianhydride may include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-cyclohexane-1,2-dicarboxylic anhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-tetralin-1,2-dicarboxylic anhydride, and 1,2,3,4-cyclobutanetetracarboxylic dianhydride. anhydride), bicyclooctene-2,3,5,6-tetracarboxylic dianhydride, bicyclooctene-1,2,4,5-tetracarboxylic dianhydride, and the like, but are not limited thereto.

[0136] (B) Photopolymerizable compound

[0137] The photosensitive resin composition according to some exemplary embodiments may further include a photopolymerizable compound. The photopolymerizable compound may be a single compound or a mixture of two different compounds.

[0138] The photopolymerizable compound may be a compound including at least two functional groups represented by Chemical Formula 3.

[0139] [Chemical Formula 3]

[0140]

[0141] In Chemical Formula 3,

[0142] R 5 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and

[0143] L 3 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

[0144] For example, the compound containing at least two functional groups represented by Chemical Formula 3 may include 2 to 6 functional groups represented by Chemical Formula 3. In this case, sufficient polymerization occurs during exposure in a pattern forming process, thereby forming a pattern having excellent heat resistance, light resistance, and chemical resistance.

[0145] For example, the compound containing at least two functional groups represented by Chemical Formula 3 may be a compound represented by any one of Chemical Formulas 4 to 6, but is not necessarily limited thereto.

[0146] [Chemical Formula 4]

[0147]

[0148] [Chemical Formula 5]

[0149]

[0150] [Chemical Formula 6]

[0151]

[0152] In Chemical Formulas 4 to 6,

[0153] p, q, r, s and t are each independently an integer from 1 to 10.

[0154] When the photopolymerizable compound is a mixture of two different compounds, the other of the two compounds may be a monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0155] The monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one ethylenically unsaturated double bond may be, for example, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hex ...6-hexanedioldi(meth)acrylate), bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate A epoxy (meth) acrylate), ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolacepoxy (meth) acrylate, or a combination thereof.

[0156] Commercially available products of monofunctional or polyfunctional ester compounds of (meth)acrylic acid having at least one ethylenically unsaturated double bond are as follows. Examples of monofunctional esters of (meth)acrylic acid include Aronix M-101, M-111, M-114 (Toagosei Chemistry Industry Co., Ltd.); KAYARAD (Nippon Kayaku Co., Ltd.); (Osaka Organic Chemical Ind., Ltd.) etc. Examples of difunctional esters of (meth)acrylic acid may include Aronix (Togosei Chemical Industry Co., Ltd.), KAYARAD (Nippon Kayaku Co., Ltd.), V-335 (Osaka Organic Chemical Industry Co., Ltd.) etc. Examples of the trifunctional ester of (meth)acrylic acid may include Aronix (Togosei Chemical Industry Co., Ltd.), KAYARAD KAYARAD KAYARAD KAYARAD KAYARAD (Nippon Kayaku Co., Ltd.), (Osaka Yuki Kayaku Kogyo Co., Ltd.), etc. These may be used alone or in combination of two or more.

[0157] The photopolymerizable compound may be used after being treated with an acid anhydride to provide better developability.

[0158] The photopolymerizable compound may be included in an amount of about 5 parts by weight to about 20 parts by weight, for example, about 7 parts by weight to about 15 parts by weight, based on 100 parts by weight of the photosensitive resin composition. If the photopolymerizable compound is included within the above range, curing is sufficient, reliability is excellent, heat resistance, light resistance, and chemical resistance of the pattern are improved, and resolution and adhesion are also improved.

[0159] (C) Photoinitiator

[0160] The photosensitive resin composition according to some exemplary embodiments includes a photoinitiator represented by Chemical Formula 1.

[0161] For example, in Chemical Formula 1, R 1 and R 3 can be identical to each other. For example, R 1 and R 3 Each independently may be a substituted or unsubstituted C6 to C20 aryl group.

[0162] For example, R 2 It may be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C3 to C20 cycloalkyl group.

[0163] In Chemical Formula 1, when R1 to R 3 As above, pattern formation can be more easily controlled, and it is also advantageous in increasing the resolution of the pattern.

[0164] For example, the photoinitiator represented by Chemical Formula 1 may include at least one selected from the group consisting of compounds represented by Chemical Formula 1-1 to Chemical Formula 1-3, but is not necessarily limited thereto.

[0165] [Chemical Formula 1-1]

[0166]

[0167] [Chemical formula 1-2]

[0168]

[0169] [Chemical formula 1-3]

[0170]

[0171] For example, the photoinitiator represented by Chemical Formula 1 may be included in an amount of about 1 part by weight to about 5 parts by weight, for example, about 1 part by weight to about 3 parts by weight, based on 100 parts by weight of the photosensitive resin composition. If the photoinitiator represented by Chemical Formula 1 is included within the above range, photopolymerization occurs sufficiently, resulting in excellent sensitivity and improved transmittance.

[0172] Meanwhile, the photosensitive resin composition according to some exemplary embodiments may further include other types of photoinitiators in addition to the photoinitiator (oxime-based photoinitiator) represented by Chemical Formula 1. Other types of photoinitiators may include, for example, acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, and the like.

[0173] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropinophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.

[0174] Examples of the benzophenone compound may include benzophenone, benzoylbenzoate, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

[0175] Examples of the thioxanthone compound may include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and the like.

[0176] Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.

[0177] Examples of the triazine compound may include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-phenyl-s-triazine, 2-(naphthol-1-yl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(naphthol-1-yl)-4,6-bis(trichloromethyl)-s-triazine. hyl)-s-triazine), 2-(4-methoxynaphthol1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc.

[0178] In addition to the above compounds, the photoinitiator may include carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, and fluorene-based compounds.

[0179] (D) Solvent

[0180] The solvent may be a material that is compatible but non-reactive with the resin, the photopolymerizable compound, and the photoinitiator.

[0181] Examples of the solvent may include alcohols such as methanol, ethanol, etc.; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, tetrahydrofuran, etc.; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, etc.; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, diethyl cellosolve acetate, etc.; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol diethyl ether, etc.; propylene glycol alkyl ether acetates such as propylene glycol alkyl ether acetates. glycolalkyletheracetate), such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons, such as toluene, xylene, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-pentyl ketone, 2-heptanone, etc.; saturated aliphatic monocarboxylic acid alkyl esters, such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactic acid esters such as methyl lactate, ethyl lactate, etc.; oxyacetic acid alkyl esters, such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, etc.; alkoxyacetic acid alkyl esters, such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, ethoxyethyl acetate, etc.; 3-oxypropionic acid alkyl esters, such as methyl 3-oxypropionate (3-oxymethylpropionate), ethyl 3-oxypropionate, etc.; 3-alkoxypropionic acid alkyl esters, such as Such as 3-methoxymethylpropionate, 3-methoxyethylpropionate, 3-ethoxyethylpropionate, 3-ethoxymethylpropionate, etc.; 2-oxypropionic acid alkyl esters, such as 2-oxypropionic acid methyl ester, 2-oxypropionic acid ethyl ester, 2-oxypropionic acid propyl ester, etc.; 2-alkoxypropionic acid alkyl esters, such as 2-methoxymethylpropionate, 2-methoxyethylpropionate, 2-ethoxyethylpropionate, 2-ethoxymethylpropionate, etc.; 2-oxy-2-methylpropionic acid esters, such as 2-oxy-2-methylmethylpropionic acid ester, 2-oxy-2-methylethylpropionic acid ester, etc., monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylalkylpropionic acid esters, such as 2-methoxy-2-methylmethylpropionic acid ester, 2-ethoxy-2-methylethylpropionic acid ester, etc.; esters, such as 2-hydroxyethylpropionic acid ester, 2-hydroxy-2-methylethylpropionic acid ester, hydroxyethyl acetate, 2-hydroxy-3-methylbutyric acid methyl ester, etc.; ketoesters, such as ethyl pyruvate (ethyl pyruvate) etc.In addition, high-boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, methyl 3-benzoate, ethylene carbonate, propylene carbonate, and phenyl acetate cellosolve can also be used.

[0182] The solvent may be present in an amount of about 40 to about 80 parts by weight based on 100 parts by weight of the photosensitive resin composition. If the solvent is included within this range, the photosensitive resin composition may have appropriate viscosity, thereby having excellent processability when manufacturing a photosensitive resin layer.

[0183] (E) Other additives

[0184] The photosensitive resin composition according to some exemplary embodiments may further include other additives.

[0185] The photosensitive resin composition may include a diacid (e.g., malonic acid), an alkanolamine (e.g., 3-amino-1,2-propylene glycol), a photosensitizer, an antioxidant, an adhesion (promoting) agent, a leveling agent, a silane coupling agent, a surfactant, an epoxy compound, a thermal latent acid generator, a development control agent, a curing agent, or a combination thereof, to prevent stains or spots during coating, provide leveling properties, or prevent residues from being generated due to non-development. The amount of these additives used can be easily adjusted according to the desired physical properties.

[0186] For example, if the photosensitive resin composition further includes a photosensitizer, the content of the photosensitizer may be less than the content of the photoinitiator represented by Chemical Formula 1. Furthermore, in addition to the photosensitizer, the photosensitive resin composition according to some example embodiments may further include an antioxidant, and in this case, the content of the antioxidant may be less than the content of the photosensitizer. Controlling the amounts of the photoinitiator, photosensitizer, and antioxidant represented by Chemical Formula 1 as described above may be more advantageous in terms of pattern formation and high resolution.

[0187] For example, the silane coupling agent may have a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, or an epoxy group to improve adhesion to the substrate, and may have a structure different from that of the silane compound.

[0188] Examples of the silane coupling agent may include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.

[0189] The silane coupling agent may be included in an amount of about 0.01 parts by weight to about 10 parts by weight based on 100 parts by weight of the photosensitive resin composition.

[0190] For example, a surfactant is added to prevent uneven film thickness or improve developability, and the surfactant may include a fluorine-based surfactant and / or a silicone-based surfactant.

[0191] Examples of fluorochemical surfactants include commercially available fluorochemical surfactants such as those from BM Chemical Company (BM Chemie Inc.) etc.; MEGAFACE F of Dainippon Ink Kagaku Kogyo Co., Ltd. MEGAFACE F MEGAFACE F MEGAFACE F MEGAFACE F etc.; FULORAD of Sumitomo 3M Co.,Ltd. FULORAD FULORAD FULORAD etc.; SURFLON from Asahi Glass Co., Ltd. SURFLON SURFLON SURFLON SURFLON etc.; Toray Silicone Co., Ltd. wait.

[0192] The silicone surfactant can be a commercially available silicone surfactant, such as BYK-307, BYK-333, BYK-361N, BYK-051, BYK-052, BYK-053, BYK-067A, BYK-077, BYK-301, BYK-322, BYK-325, BYK-378, etc. from BYK Chem.

[0193] The surfactant may be used in an amount of about 0.001 parts by weight to about 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. If the surfactant is included within the above range, coating uniformity can be ensured without generating stains, and coating on an ITO substrate or a glass substrate, a Si wafer or a SiN wafer can be improved. x Wettability on wafer and Cu substrate.

[0194] In addition, the photosensitive resin composition further includes an epoxy compound to improve adhesion to the substrate, etc. Examples of the epoxy compound may include phenol novolac epoxy compounds, tetramethyl biphenyl epoxy compounds, bisphenol A epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

[0195] The epoxy compound may be used in an amount of about 0.01 parts by weight to about 5 parts by weight based on 100 parts by weight of the photosensitive resin composition.

[0196] In addition, the photosensitive resin composition may further include a thermal latent acid generator. Examples of the thermal latent acid generator may include arylsulfonic acids such as p-toluenesulfonic acid and benzenesulfonic acid; perfluoroalkylsulfonic acids such as trifluoromethanesulfonic acid and trifluorobutanesulfonic acid; alkylsulfonic acids such as methanesulfonic acid, ethanesulfonic acid, and butanesulfonic acid; or combinations thereof, but are not limited thereto.

[0197] Furthermore, the photosensitive resin composition may contain a predetermined amount of other additives such as a stabilizer, as long as the properties of the photosensitive resin composition are not deteriorated.

[0198] Some exemplary embodiments provide a photosensitive resin layer, such as a semiconductor redistribution layer insulating layer, manufactured by exposing, developing, and curing the aforementioned photosensitive resin composition.

[0199] The method for manufacturing the photosensitive resin layer (semiconductor redistribution layer insulating layer) is as follows.

[0200] (1) Coating and film formation

[0201] The photosensitive resin composition is coated on a glass substrate or ITO substrate, Si wafer or SiN substrate that has been pretreated by spin coating, slit coating, roller coating, screen printing, applicator method, etc. x The film is formed on a substrate such as a wafer or a Cu substrate to have a desired thickness and heated at about 70° C. to about 150° C. for about 1 minute to about 10 minutes to remove the solvent.

[0202] (2) Exposure

[0203] After placing a mask on the resulting photosensitive resin layer to form a desired pattern, the layer is exposed to actinic radiation of 200 to 500 nanometers. Light sources for exposure include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and argon lasers. In some cases, X-rays and electron beams may also be used.

[0204] The exposure dose varies depending on the type, mixing amount, and dry film thickness of each component of the composition, but is less than 500 mJ / cm when using a high-pressure mercury lamp. 2 (Based on 365 nm sensor).

[0205] (3) Development

[0206] In the development method, after the exposure step, an alkaline aqueous solution or an organic solvent is used as a developer to dissolve and remove unnecessary portions, leaving only the exposed portions to form a pattern.

[0207] (4) Post-processing

[0208] A post-heating process is used to obtain an image pattern developed in the above process that is excellent in heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength, and storage stability. For example, after development, the image pattern may be heated in an oven at 200°C to 400°C under a nitrogen atmosphere for at least one hour.

[0209] Some example embodiments provide a semiconductor device including a photosensitive resin layer (semiconductor redistribution layer insulating layer).

[0210] Hereinafter, preferred examples of the present invention will be described. However, the following examples are merely preferred examples of the present invention, and the present invention is not limited to the following examples.

[0211] (Example)

[0212] (Synthesis Example 1: Synthesis of Polyamide Ester (Polyimide Precursor) Resin)

[0213] 0.58 mol of the dianhydride monomer represented by Chemical Formula A and 1.22 mol of 2-hydroxyethylmethacrylate (HEMA) were added to 600 g of γ-butyrolactone (GBL) in a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen injection device, and a cooler. While stirring at room temperature, 1.16 mol of pyridine was added to obtain a reaction mixture. After reacting at room temperature for 16 hours and lowering the temperature to -10°C, a solution prepared by dissolving 250 g of GBL in 1.17 mol of dicyclohexylcarbodiimide (DCC) was added dropwise over 30 minutes. After stirring the mixture for another 5 minutes, a solution of 0.54 mol of the diamine monomer represented by Chemical Formula B and 300 g of GBL was added thereto for 40 minutes, followed by further stirring for 2 hours. After reacting at room temperature for 1 hour, 30 g of ethanol was added thereto, followed by stirring for 1 hour. Subsequently, GBL was added thereto until the reaction solution had a solid content of 18%, and then added to 3 liters of ethanol to obtain a precipitate. The polymer was filtered and dissolved in 1.5 liters of tetrahydrofuran (THF), and then added dropwise to 30 liters of water to produce a precipitate, which was vacuum-dried. The resulting product was dried under reduced pressure at 50°C for more than 24 hours to prepare a polyamide ester resin containing the structural unit represented by Chemical Formula 1-1.

[0214] [Chemical Formula A]

[0215]

[0216] [Chemical Formula B]

[0217]

[0218] [Chemical Formula 1-1]

[0219]

[0220] (Preparation of Photosensitive Resin Composition)

[0221] The photosensitive resin compositions of Examples 1 to 6 and Comparative Examples 1 to 4 were prepared according to the compositions shown in Table 1. Specifically, after adding a solvent to the above-mentioned polyamide ester resin, a photopolymerizable monomer, a photoinitiator, and other additives were added, followed by thorough stirring. Subsequently, the mixture was filtered through a 0.45 μm polypropylene resin filter to obtain negative-type photosensitive resin compositions.

[0222] (Table 1)

[0223]

[0224] (A) Resin

[0225] Resin of Synthesis Example 1

[0226] (B) Photopolymerizable compound

[0227] Tetraethylene glycol dimethacrylate (manufacturer)

[0228] (C) Photoinitiator (C-1) NCI831

[0229] (C-2)PBG305

[0230] (C-3) SPI03 (Samyang) (C-4) Compound represented by Chemical Formula C

[0231] (C-5) Compound represented by Chemical Formula 1-1 (C-6) Compound represented by Chemical Formula 1-2 (C-7) Compound represented by Chemical Formula 1-3 [Chemical Formula 1-1]

[0232]

[0233] [Chemical formula 1-2]

[0234]

[0235] [Chemical formula 1-3]

[0236]

[0237] [Chemical Formula C]

[0238]

[0239] (D) Solvent (D-1) GBL

[0240] (D-2)DMSO

[0241] (E) Other additives

[0242] Photosensitizer: N-phenyldiethanolamine Antioxidant: CX-1790 Adhesion promoter: KBM-573 (evaluation)

[0243] The photosensitive resin compositions of Examples 1 to 6 and Comparative Examples 1 to 4 were spin-coated on an 8-inch silicon wafer, pre-baked at about 100°C for 4 minutes, and coated to a thickness of about 10.0 μm. Then, after cooling at room temperature for 60 seconds, light was irradiated for 700 msec using an i-line stepper (NSR-2005i10C, Nikon Inc.) to induce a photocuring reaction in the photosensitive portion. The exposed substrate was developed twice for 60 seconds in a puddle method using a 100% cyclopentanone solvent at room temperature, and then washed for 60 seconds using a 100% PGMEA solvent. Subsequently, 5 μm, 10 μm, and 20 μm patterns for evaluation were confirmed using a CD-SEM (Hitachi Ltd.). In addition, the taper angle was confirmed for the cross-section cut using the FIB, and the results are shown in Tables 2 and 3. Figures 1 to 7 . Visually inspect the FIB image of the cross section to determine whether it is good or poor.

[0244] (Table 2)

[0245]

[0246] According to Table 2, the photosensitive resin compositions according to Examples can easily form excellent patterns and achieve high resolution, making them suitable for use as compositions for semiconductor redistribution layers.

[0247] Although the present invention has been described in conjunction with what are presently considered to be practical example embodiments, it should be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. Therefore, the foregoing embodiments should be understood as illustrative, but not limiting of the present invention in any way.

Claims

1. A photosensitive resin composition comprising: (A) at least one resin selected from a polyimide precursor and a polybenzoxazole precursor; (B) a photopolymerizable compound; (C) a photoinitiator represented by Chemical Formula 1; and (D) Solvent: [Chemical Formula 1] Wherein in Chemical Formula 1, R 1 to R 3 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C20 aryl, provided that R 1 to R 3 Not all hydrogen atoms.

2. The photosensitive resin composition according to claim 1, wherein R 1 and R 3 The same as each other.

3. The photosensitive resin composition according to claim 1, wherein R 1 and R 3 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

4. The photosensitive resin composition according to claim 1, wherein R 2 is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C3 to C20 cycloalkyl group.

5. The photosensitive resin composition according to claim 1, wherein Chemical Formula 1 includes at least one compound selected from the group consisting of the compounds represented by Chemical Formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] 6. The photosensitive resin composition according to claim 1, wherein The photoinitiator represented by Chemical Formula 1 is included in an amount of about 1 part by weight to about 5 parts by weight based on 100 parts by weight of the photosensitive resin composition.

7. The photosensitive resin composition according to claim 1, wherein The photosensitive resin composition further includes a photosensitizer.

8. The photosensitive resin composition according to claim 7, wherein The content of the photosensitizer is less than that of the photoinitiator represented by Chemical Formula 1.

9. The photosensitive resin composition according to claim 8, wherein The photosensitive resin composition further includes an antioxidant, and the content of the antioxidant is less than that of the photosensitizer.

10. The photosensitive resin composition according to claim 1, wherein Based on 100 parts by weight of the photosensitive resin composition, the photosensitive resin composition includes: 20 to 40 parts by weight of the resin, 1 part by weight to 10 parts by weight of the photopolymerizable compound, 1 to 5 parts by weight of the photoinitiator, and 40 to 80 parts by weight of the solvent.

11. The photosensitive resin composition according to claim 1, wherein The photosensitive resin composition includes additives such as diacid, alkanolamine, leveling agent, silane coupling agent, surfactant, epoxy compound, thermal latent acid generator or a combination thereof.

12. The photosensitive resin composition according to claim 1, wherein The photosensitive resin composition is a negative photosensitive resin composition. 13 . A photosensitive resin layer produced using the photosensitive resin composition according to claim 1 .

14. The photosensitive resin layer according to claim 13, wherein The photosensitive resin layer is a semiconductor redistribution layer insulating layer. 15 . A semiconductor device comprising the photosensitive resin layer according to claim 13 .

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