KR20220025469A - Photosensitive resin composition, photosensitive resin layer and semiconductor device using the same - Google Patents

Abstract

Provided are a photosensitive resin composition, a photosensitive resin film manufactured by using the same, and a semiconductor device including the photosensitive resin film. The photosensitive resin composition includes: (A) a polyhydroxyamide-based resin including a structural unit represented by Chemical Formula 1; (B) a photopolymerizable compound; (C) a photopolymerization initiator; (D) an additive including a sulfide linking group or a disulfide linking group and including at least one carboxyl group at a terminal thereof; and (E) a solvent. (In Chemical Formula 1, each substituent is as defined in the present disclosure.) Accordingly, an insulating film for a semiconductor redistribution layer having excellent heat resistance and reliability is implemented.

Description

Photosensitive resin composition, photosensitive resin film and semiconductor device using the same

The present disclosure relates to a photosensitive resin composition, a photosensitive resin film using the same, and a semiconductor device.

A method of sealing a semiconductor element with an epoxy resin composition for the purpose of protecting the semiconductor element from an external environment such as moisture or mechanical shock has been commercially performed. Conventionally, semiconductor chips are manufactured by dicing a wafer during sealing of semiconductor devices, and then packaging is performed in units of semiconductor chips. Next, a process for dicing into a semiconductor chip was developed. 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).

Compared to the chip-scale packaging process, wafer-level packaging has advantages in that the process yield is high and the semiconductor mounting space can be reduced because the package thickness is thin. However, in the case of wafer-level packaging or panel-level packaging, since the film forming area is larger than that of chip-scale packaging that encapsulates individual chips, there is a problem in that warpage due to the difference in thermal expansion rate between the wafer or panel and the encapsulant occurs greatly. When warpage occurs, it affects the yield and wafer handling of subsequent processes. In addition, liquid type epoxy resin or silicone resin is mainly used as a sealing material for wafer level packaging or panel level packaging at present. There is a problem in that the reliability of the semiconductor package after sealing is weak.

Accordingly, there is a demand for the development of an insulating film for a redistribution layer (RDL) capable of reducing warpage and implementing excellent reliability even when wafer level packaging or panel level packaging is applied.

In order to meet the above demands, the development of a photosensitive resin composition capable of forming an insulating film for a redistribution layer is continued, and in general, a photosensitive polyimide resin composition in which photosensitivity is imparted to the polyimide resin itself has been mainly used. It is because the pattern formation process can be simplified by using the photosensitive polyimide resin composition. However, in the case of a conventional insulating film (cured film) for a redistribution layer manufactured using a photosensitive polyimide resin composition, there is a problem in that corrosion resistance and chemical resistance are lowered. In particular, the resin for an insulating film for a redistribution layer requires low temperature curing, Conventional photosensitive polyimide resin has a problem in that it cannot be cured at a low temperature and thus high heat resistance and high reliability cannot be achieved.

According to one embodiment, by using a polyhydroxyamide-based resin having a specific structure together with an 'additive including a sulfide linkage group or a disulfide linkage group and at least one carboxyl group at the terminal', the adhesive strength with copper in the redistribution layer is improved. It is to provide a photosensitive resin composition which can be usefully used as an interlayer insulating film between semiconductor rewiring by improving.

Another embodiment is to provide a photosensitive resin film prepared using the photosensitive resin composition.

Another embodiment is to provide a semiconductor device including the photosensitive resin film.

One embodiment is (A) a polyhydroxyamide-based resin including a structural unit represented by the following formula (1); (B) a photopolymerizable compound; (C) a photoinitiator; (D) an additive comprising a sulfide linkage or a disulfide linkage and at least one carboxyl group at the terminal; And (E) provides a photosensitive resin composition comprising a solvent.

[Formula 1]

In Formula 1,

X ¹ is a residue derived from an anhydride monomer,

Y ¹ is a residue derived from a diamine monomer,

R ¹ and R ² are each 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 hetero it is a ring

The additive may be represented by the following formula (2).

[Formula 2]

In Formula 2,

R ³ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group;

L ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,

L ² is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.

In Formula 2, L ² may be a C6 to C20 arylene group unsubstituted or substituted with a carboxyl group.

The additive represented by Formula 2 may be represented by any one of Formulas 2-1 to 2-6 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

The additive may be represented by the following formula (3).

[Formula 3]

In Formula 3,

L ³ to L ⁷ are each independently a single bond, a sulfide linking group, a disulfide linking group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a divalent thiophene linking group, wherein At least one of L ³ to L ⁷ is necessarily a sulfide linking group, a disulfide linking group, or a divalent thiophene linking group.

When any one or more of L ³ to L ⁷ is a substituted or unsubstituted C1 to C20 alkylene group, it is a 'C1 to C20 alkylene group substituted with a C1 to C10 alkyl group', 'C1 to C20 alkylene group substituted with a carboxyl group ' or 'unsubstituted C1 to C20 alkylene group'.

The additive represented by Formula 3 may be represented by any one of Formulas 3-1 to 3-12 below.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

[Formula 3-9]

[Formula 3-10]

[Formula 3-11]

[Formula 3-12]

The additive may be included in an amount of 1 to 20 parts by weight based on 100 parts by weight of the polyhydroxyamide-based resin.

The anhydride monomer may be represented by the following Chemical Formula X-1.

[Formula X-1]

In the formula (X-1),

L ⁸ is a single bond, *-O-*, *-S-*, *-C(=O)-*, *-C(=O)O-*, -*NR ⁴ -*(R ⁴ is hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic linking group, or a combination thereof am.

The diamine monomer may be represented by Formula Y-1 or Formula Y-2 below.

[Formula Y-1]

[Formula Y-2]

In the formula Y-2,

R ⁵ and R ⁶ 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,

L ⁹ is *-O-* or *-S-*,

n1 and n2 are each independently an integer of 0 to 4.

In the photosensitive resin composition, based on 100 parts by weight of the polyhydroxyamide-based resin, the photopolymerizable compound is included in an amount of 1 to 10 parts by weight, the photopolymerization initiator is included in an amount of 1 to 10 parts by weight, and the additive is included in an amount of 1 part by weight to 20 parts by weight, and the solvent may be included in an amount of 100 parts by weight to 500 parts by weight.

The photosensitive resin composition may further include a diacid, an alkanolamine, a leveling agent, a silane coupling agent, a surfactant, an epoxy compound, a thermal latent acid generator, or a combination thereof.

The photosensitive resin composition may be a negative photosensitive resin composition.

Another embodiment provides a photosensitive resin film prepared by using the photosensitive resin composition.

Another embodiment provides a semiconductor device including the photosensitive resin film.

The specific details of other aspects of the invention are included in the detailed description below.

The photosensitive resin composition according to an embodiment includes a polyhydroxyamide-based resin having a specific structure, a metal layer (eg, copper layer and titanium layer), so that an insulating film for a semiconductor redistribution layer having excellent heat resistance and reliability can be realized.

1 is a schematic diagram of a die shear tester device for evaluating the adhesive force of a photosensitive resin composition.

Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

Unless otherwise specified herein, "alkyl group" means a C1 to C20 alkyl group, "alkenyl group" means a C2 to C20 alkenyl group, "cycloalkenyl group" means a C3 to C20 cycloalkenyl group, , "heterocycloalkenyl group" means a C3 to C20 heterocycloalkenyl group, "aryl group" means a C6 to C20 aryl group, "arylalkyl group" means a C7 to C20 arylalkyl group, "alkylene group" means a C1 to C20 alkylene group, "arylene group" means a C6 to C20 arylene group, "alkylarylene group" means a C7 to C20 alkylarylene group, and "heteroarylene group" means a C3 to C20 hetero It means an arylene group, and "alkoxyylene group" means a C1 to C20 alkoxyylene group.

Unless otherwise specified herein, "substitution" means a C1 to C20 alkyl group in which at least one hydrogen atom is substituted with a halogen atom such as a halogen atom (F, Cl, Br, I), a trifluoromethyl group, a hydroxy group, or a C1 to C20 alkoxy group group, nitro group, cyano group, amine group, imino group, azido group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, ether group, carboxyl group or a salt thereof; Sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C20 aryl group, C3 to C20 cycloalkyl group, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl group, C2 to C20 heterocycloalkyl group, C2 to C20 heterocycloalkenyl group, C2 to C20 heterocycloalkynyl group, C3 to C20 heteroaryl group, or a combination thereof means substituted with a substituent.

In addition, unless otherwise specified in the present specification, "hetero" means that at least one hetero atom among N, O, S and P is included in the formula.

In addition, unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible.

Unless otherwise defined herein, "combination" means mixing or copolymerization. Also, "copolymerization" means block copolymerization, alternating copolymerization or random copolymerization, and "copolymer" means block copolymer, alternating copolymer or random copolymer.

Unless otherwise specified herein, the unsaturated bond includes not only multiple bonds between carbon-carbon atoms, but also other molecules such as carbonyl bonds and azo bonds.

Unless otherwise defined in the chemical formulas in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded to the position.

Unless otherwise defined herein, "*" means a moiety connected to the same or different atoms or chemical formulas.

The photosensitive resin composition according to an embodiment includes (A) a polyhydroxyamide-based resin including a structural unit represented by the following Chemical Formula 1; (B) a photopolymerizable compound; (C) a photoinitiator; (D) an additive comprising a sulfide linkage or a disulfide linkage and at least one carboxyl group at the terminal; and (E) a solvent.

[Formula 1]

In Formula 1,

X ¹ is a residue derived from an anhydride monomer,

Y ¹ is a residue derived from a diamine monomer,

R ¹ and R ² are each 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 hetero it is a ring

For example, R ¹ and R ² may each independently be a C1 to C20 alkyl group in which a (meth)acrylate group is unsubstituted or substituted at the terminal.

Hereinafter, each component will be described in detail.

(A) polyhydroxyamide-based resin

The polyhydroxyamide-based resin used in the photosensitive resin composition according to an embodiment includes a structural unit represented by Formula 1 above.

The structural unit-containing polyhydroxyamide-based resin represented by Formula 1 can be used together with an additive to be described later, thereby very easily improving adhesion to a metal layer (especially a copper layer and a titanium layer), and in addition to this, a negative type resin It is also easy to greatly improve developability by being applied to the composition.

In general, alkali-soluble resins having a closed cyclic structure have a problem in that the film properties are slightly deteriorated during low-temperature curing. The photosensitive resin composition according to an embodiment is suitable for low-temperature curing and may provide an insulating film (cured film) having very excellent film properties.

For example, the structural unit-containing polyhydroxyamide-based resin represented by Formula 1 may be a polymer between an anhydride monomer and a diamine monomer.

For example, the diamine monomer may be represented by the following Chemical Formula Y-1 or the following Chemical Formula Y-2.

[Formula Y-1]

[Formula Y-2]

In the formula Y-2,

R ⁵ and R ⁶ 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,

L ⁹ is *-O-* or *-S-*,

n1 and n2 are each independently an integer of 0 to 4.

For example, the anhydride monomer may include a monomer represented by the following Chemical Formula X-1, but is not necessarily limited thereto.

[Formula X-1]

In the formula (X-1),

L ⁸ is a single bond, *-O-*, *-S-*, *-C(=O)-*, *-C(=O)O-*, -*NR ⁴ -*(R ⁴ is hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic linking group, or a combination thereof am.

For example, when L ⁸ is a substituted or unsubstituted C1 to C20 alkylene group, it may be a C1 to C20 alkylene group unsubstituted or substituted with a trifluoroalkyl group.

The weight average molecular weight (M _w ) of the polyhydroxyamide-based resin may be 3,000 g/mol to 300,000 g/mol. When the weight average molecular weight of the polyhydroxyamide-based resin is within the above range, sufficient physical properties can be obtained and handling is easy due to excellent solubility in organic solvents.

(B) photopolymerizable compound

The photopolymerizable compound in the photosensitive resin composition according to the exemplary embodiment may be a single compound or a mixture of two different compounds.

When the photopolymerizable compound is a mixture of two different types of compounds, any one of the two types of compounds may be a compound including at least two functional groups represented by Formula 4 below.

[Formula 4]

In Formula 4,

R ¹⁰⁰ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ¹⁰⁰ is a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

For example, the compound including at least two functional groups represented by Formula 4 may include 2 to 6 functional groups represented by Formula 4 above. In this case, sufficient polymerization occurs during exposure in the pattern forming process to form a pattern having excellent heat resistance, light resistance, and chemical resistance.

For example, the compound including at least two functional groups represented by Formula 4 may be a compound represented by Formula 5 or Formula 6 below.

[Formula 5]

[Formula 6]

In Formulas 5 and 6,

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

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

The monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one ethylenically unsaturated double bond is, 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-hexanediol di (meth) acrylate, bisphenol A Di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipenta Erythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, Bisphenol A epoxy (meth)acrylate , ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate, or a combination thereof.

Commercially available products of the monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one ethylenically unsaturated double bond are as follows. Examples of the monofunctional ester of (meth)acrylic acid include Aronix M-101 ^® , Aronix M-111 ^® , Aronix M-114 ^® by Toagosei Chemical Co., Ltd.; Nihon Kayaku Co., Ltd.'s KAYARAD TC-110S ^® , KAYARAD TC-120S ^® , etc.; Osaka Yuki Chemical Co., Ltd.'s V-158 ^® , V-2311 ^® , etc. are mentioned. Examples of the bifunctional ester of (meth)acrylic acid, Toago Sei Chemicals Co., Ltd. Aronix M-210 ^® , Aronix M-240 ^® , Aronix M-6200 ^® and the like; Nihon Kayaku Co., Ltd.'s KAYARAD HDDA ^® , KAYARAD HX-220 ^® , KAYARAD R-604 ^® , etc.; and V-260 ^® , V-312 ^® , V-335 HP ^® of Osaka Yuki Chemical High School Co., Ltd. and the like. Examples of the trifunctional ester of (meth)acrylic acid include Aronix M-309 ^® , Aronix M-400 ^® , Aronix M-405 ^® , Aronix M-450 ^® by Toago Sei Chemicals Co., Ltd. , Aronix M-7100 ^® , Aronix M-8030 ^® , Aronix M-8060 ^® etc.; Nihon Kayaku Co., Ltd.'s KAYARAD TMPTA ^® , KAYARAD DPCA-20 ^® , KAYARAD DPCA-30 ^® , KAYARAD DPCA-60 ^® , KAYARAD DPCA-120 ^® , etc.; V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® of Osaka Yukigayaku High School Co., Ltd. may be mentioned. These products may be used alone or in combination of two or more.

The photopolymerizable compound may be used after treatment with an acid anhydride in order to provide better developability.

The photopolymerizable compound may be included in an amount of 1 to 10 parts by weight, for example, 1 to 7 parts by weight based on 100 parts by weight of the polyhydroxyamide-based compound. When the photopolymerizable compound is contained within the above range, 　 hardening occurs sufficiently, and reliability is excellent, heat resistance, light resistance and chemical resistance of the pattern are excellent, and resolution and adhesion are also excellent.

(C) photoinitiator

The photosensitive resin composition according to an embodiment includes a photoinitiator. As the photopolymerization initiator, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxime-based compound may be used.

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholino propane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethyl amino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc. are mentioned.

Examples of the thioxanthone-based compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diiso A propyl thioxanthone etc. are mentioned.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'- Dimethoxystyryl)-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-styryl-s-triazine, 2-(naphtho1-yl)-4,6 -Bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloro and romethyl)-6-piperonyl-s-triazine and 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine.

Examples of the oxime-based compound include O-acyloxime-based compound, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxime) -1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one, etc. can be used Specific examples of the O-acyloxime compound include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane -1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2- Dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime -O-acetate　 etc. can be used.

As the photopolymerization initiator, a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a biimidazole-based compound, or a fluorene-based compound may be used in addition to the above compound.

The photopolymerization initiator may be included in an amount of 1 to 10 parts by weight, for example, 1 to 7 parts by weight based on 100 parts by weight of the polyhydroxyamide-based agent. When the photopolymerization initiator is included within the above range, photopolymerization occurs sufficiently, so that the sensitivity is excellent and the transmittance is improved.

(D) an additive comprising a sulfide linkage or a disulfide linkage, and at least one carboxyl group at the terminal

The photosensitive resin composition according to an embodiment includes an additive including the sulfide linking group or the disulfide linking group and at least one carboxyl group at the terminal thereof.

Since the additive includes a sulfide linkage group or a disulfide linkage group and includes at least one carboxyl group at the terminal, it can be used together with the above-described polyhydroxyamide-based resin to form a photosensitive resin composition advantageous for low-temperature curing. , the adhesion with the metal layer (especially the copper layer and the titanium layer) is greatly improved, so it is very suitable for use as an insulating film between semiconductor redistribution layers.

Specifically, due to the sulfide linking group or the disulfide linking group in the additive, adhesion to the metal layer and the titanium layer may be improved, and the carboxyl group may improve adhesion to the polyhydroxyamide-based resin, so in one embodiment The photosensitive resin composition according to the present invention is very advantageous to be used as an insulating film for a semiconductor redistribution layer.

For example, the additive may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[Formula 2]

In Formula 2,

R ³ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group;

L ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,

L ² is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.

[Formula 3]

In Formula 3,

L ³ to L ⁷ are each independently a single bond, a sulfide linking group, a disulfide linking group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a divalent thiophene linking group, wherein At least one of L ³ to L ⁷ is necessarily a sulfide linking group, a disulfide linking group, or a divalent thiophene linking group.

In general, the copper layer in the semiconductor redistribution layer includes a small amount of titanium in addition to copper, and all of the additives represented by Formula 2 or Formula 3 have a sulfide coupling group or a disulfide coupling group, which is advantageous in improving adhesion with the titanium, and the copper layer It can be easily predicted that the adhesive force with the material will be very good.

For example, in Formula 2, L ² may be a C6 to C20 arylene group unsubstituted or substituted with a carboxyl group.

For example, the additive represented by Formula 2 may be represented by any one of Formulas 2-1 to 2-6, but is not limited thereto.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

For example, in Formula 3, when at least one of L ³ to L ⁷ is a substituted or unsubstituted C1 to C20 alkylene group, it is a C1 to C20 alkylene group substituted with a C1 to C10 alkyl group, C1 to C20 substituted with a carboxyl group It may be a C20 alkylene group or an unsubstituted C1 to C20 alkylene group.

For example, the additive represented by Formula 3 may be represented by any one of Formulas 3-1 to 3-12, but is not limited thereto.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

[Formula 3-9]

[Formula 3-10]

[Formula 3-11]

[Formula 3-12]

The additive may be included in an amount of 1 to 20 parts by weight, for example, 5 to 15 parts by weight, based on 100 parts by weight of the polyhydroxyamide-based resin. When the additive is included in the above range, adhesion to the copper layer and the titanium layer and adhesion to the polyhydroxyamide-based resin may be simultaneously improved.

(E) solvent

As the solvent, materials having compatibility with the polyhydroxyamide-based resin, the photopolymerizable compound, the photopolymerization initiator, and the additive but not reacting may be used.

Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol dimethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; 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, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; alkoxy acetate alkyl esters such as methyl methoxy acetate, ethyl methoxy acetate, butyl methoxy acetate, methyl ethoxy acetate, and ethyl ethoxy acetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as 3-methoxymethylpropionate, 3-methoxyethylpropionate, 3-ethoxyethylpropionate, and 3-ethoxymethylpropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionic acid esters such as 2-oxy-2-methylpropionate and 2-oxy-2-methylpropionate ethyl, 2-methoxy-2-methylpropionate, 2-ethoxy-2- monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionate alkyls such as ethyl methylpropionate; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, and methyl 2-hydroxy-3-methylbutanoate; Ketonic acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, and 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, benzoic acid and high boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, 3-methylbenzoic acid, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

The solvent may be included in an amount of 100 parts by weight to 500 parts by weight based on 100 parts by weight of the polyhydroxyamide-based resin. When the solvent is included within the above range, since the photosensitive resin composition has an appropriate viscosity, processability is excellent in manufacturing the photosensitive resin film.

(F) other additives

The photosensitive resin composition according to an embodiment may further include other additives.

The photosensitive resin composition may contain diacids (eg, malonic acid, etc.), alkanolamines (eg, 3-amino-1,2- propanediol, etc.), 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. The amount of these additives used can be easily adjusted according to desired physical properties.

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, and an epoxy group in order to improve adhesion to the substrate.

Examples of the silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycy and doxypropyltrimethoxysilane and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and these may be used alone or in combination of two or more.

The silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane-based coupling agent is included within the above range, adhesion and storage properties may be excellent.

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

As the fluorine-based surfactant, BM-1000 ^® of BM Chemie, BM-1100 ^® , etc.; Mechapack F 142D ^® , Mechapack F 172 ^® , Mechapack F 173 ^® , Mechapack F 183 ^® , Mechapack F 554 ^® and the like of Dai Nippon Inki Chemical Co., Ltd.; Prorad FC-135 ^® , Prorad FC-170C ^® , Prorad FC-430 ^® , Prorad FC-431 ^® , etc. of Sumitomos Reem Co., Ltd.; Asahi Grass Co., Ltd.'s Saffron S-112 ^® , Saffron S-113 ^® , Saffron S-131 ^® , Saffron S-141 ^® , Saffron S-145 ^® , etc.; Toray Silicon Co., Ltd.'s SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® , SF-8428 ^® , etc. can be used.

The silicone-based surfactants include BYK-307, BYK-333, BYK-361N, BYK-051, BYK-052, BYK-053, BYK-067A, BYK-077, BYK-301, BYK-322, Those commercially available under the names BYK-325 and BYK-378 can be used.

The surfactant may be used in an amount of 0.001 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is secured, stains do not occur, and wettability to an ITO substrate or a glass substrate may be excellent.

In addition, the photosensitive resin composition may further include an epoxy compound as an additive to improve adhesion. As the epoxy compound, an epoxy novolac acrylic carboxylate resin, an ortho cresol novolak epoxy resin, a phenol novolac epoxy resin, a tetramethyl biphenyl epoxy resin, a bisphenol A epoxy resin, an alicyclic epoxy resin, or a combination thereof may be used. can

The epoxy compound may be used in an amount of 0.01 parts by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within the above range, it is possible to improve storage properties, adhesion and other properties.

In addition, the photosensitive resin composition may further include a thermal latent acid generator. Examples of the thermal latent acid generator 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, butanesulfonic acid and the like; Or a combination thereof may be mentioned, but is not limited thereto.

In addition, a certain amount of other additives such as antioxidants and stabilizers may be added to the photosensitive resin composition within a range that does not impair physical properties.

Another embodiment provides a photosensitive resin film prepared by exposing, developing, and curing the above-described photosensitive resin composition, for example, a semiconductor redistribution layer insulating film.

A method of manufacturing the photosensitive resin film (semiconductor redistribution layer insulating film) is as follows.

(1) Application and coating film formation step

After applying the photosensitive resin composition to a desired thickness using a method such as a spin or slit coat method, a roll coat method, a screen printing method, and an applicator method on a substrate such as a glass substrate or an ITO substrate subjected to a predetermined pretreatment, 70 A coating film is formed by heating at ℃ to 150 ℃ for 1 minute to 10 minutes to remove the solvent.

(2) exposure step

After interposing a mask to form a pattern required for the obtained photosensitive resin film, actinic rays of 200 nm to 500 nm are irradiated. As a light source used for irradiation, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, an argon gas laser, etc. may be used, and in some cases, an X-ray, an electron beam, etc. may be used.

The exposure amount varies depending on the type of each component of the composition, the compounding amount and the dry film thickness, but when a high-pressure mercury lamp is used, it is 500 mJ/cm ² (by a 365 nm sensor) or less.

(3) development step

As a developing method, after the exposure step, an alkaline aqueous solution is used as a developer to dissolve and remove unnecessary portions, thereby leaving only the exposed portion to form a pattern.

(4) post-processing step

In the above process, there is a post-heating process for obtaining a pattern excellent in heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength and storage stability of the image pattern obtained by development in the above process. For example, after development, it may be heated in a convection oven at 250° C. for 1 hour.

Another embodiment provides a semiconductor device including the photosensitive resin film (semiconductor redistribution layer insulating film).

Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only preferred examples of the present invention, and the present invention is not limited by the following examples.

(Example)

(Synthesis of polyhydroxyamide-based resin)

In 600 g of γ-butyrolactone (GBL) while passing nitrogen through a four-neck flask equipped with a stirrer, temperature controller, nitrogen gas injection device and cooler, 0.58 mol of an anhydride monomer represented by the following formula A was added, and 2-hydride 1.22 mol of oxyethyl methacrylate (HEMA) was added, and 1.16 mol of pyridine was added while stirring at room temperature to obtain a reaction mixture. After the reaction at room temperature for 16 hours, the solution was cooled to -10°C and dissolved in 1.17 mol of dicyclohexylcarbodiimide (DCC) and 250 g of GBL was added dropwise over 30 minutes. After stirring for additional 5 minutes, a solution of 0.54 mol of the diamine monomer represented by Formula B and 300 g of GBL was added for 40 minutes, followed by stirring for an additional 2 hours. After reacting at room temperature for 1 hour, 30 g of ethanol is added and stirred for 1 hour. Then, GBL is added so that the solid content of the reaction solution becomes 18%, and then added to 3 liters of ethanol to obtain a precipitate. The polymer is separated by filtration, dissolved in 1.5 liters of tetrahydrofuran (THF), and added dropwise to 30 liters of water to form a precipitate, followed by filtration and vacuum drying. By drying under reduced pressure at 50° C. for 24 hours or more, a polyamideimide precursor resin including a structural unit represented by the following Chemical Formula 1-1 was prepared. At this time, the molecular weight of the resin is checked through a polystyrene calibration curve, and it is 20k.

[Formula A]

[Formula B]

[Formula 1-1]

(Preparation of photosensitive resin composition)

Example 1

200 g of GBL (Gamma butyrolactone) as a solvent and 50 g of DMSO (Dimethyl sulfoxide) were added to 100 g of the polyhydroxyamide-based resin prepared above, 2 g of a photopolymerizable monomer (DPHA, Nippon Kayaku), and a photo polymerization initiator (SPI-02) , Samyang) 2 g and 10 g of the additive represented by the following Chemical Formula 2-1 are added, and then 0.5 g of F-554 (DIC Corporation), a fluorine-based leveling agent, is added and stirred sufficiently. Then, it filtered with a 0.45 micrometer polypropylene resin filter, and obtained the negative photosensitive resin composition.

[Formula 2-1]

Example 2

Except for using the additive represented by the following formula 2-2 instead of the additive represented by the formula 2-1, the same procedure as in Example 1 was used.

[Formula 2-2]

Example 3

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 2-3 was used instead of the additive represented by the formula 2-1.

[Formula 2-3]

Example 4

Except for using the additive represented by the following formula 2-4 instead of the additive represented by the formula 2-1, it was the same as in Example 1.

[Formula 2-4]

Example 5

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 2-5 was used instead of the additive represented by the formula 2-1.

[Formula 2-5]

Example 6

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 2-6 was used instead of the additive represented by the formula 2-1.

[Formula 2-6]

Example 7

Except for using the additive represented by the following formula 3-1 instead of the additive represented by the formula 2-1, it was carried out in the same manner as in Example 1.

[Formula 3-1]

Example 8

Except for using the additive represented by the following formula 3-2 instead of the additive represented by the formula 2-1, it was carried out in the same manner as in Example 1.

[Formula 3-2]

Example 9

Except for using the additive represented by the following formula 3-3 instead of the additive represented by the formula 2-1, the same procedure as in Example 1 was used.

[Formula 3-3]

Example 10

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 3-4 was used instead of the additive represented by the formula 2-1.

[Formula 3-4]

Example 11

The same procedure as in Example 1 was performed, except that an additive represented by the following Chemical Formula 3-5 was used instead of the additive represented by the Chemical Formula 2-1.

[Formula 3-5]

Example 12

Except for using the additive represented by the following formula 3-6 instead of the additive represented by the formula 2-1, it was the same as in Example 1.

[Formula 3-6]

Example 13

Except for using the additive represented by the following formula 3-7 instead of the additive represented by the formula 2-1, it was carried out in the same manner as in Example 1.

[Formula 3-7]

Example 14

Except for using the additive represented by the following formula 3-8 instead of the additive represented by the formula 2-1, the same procedure as in Example 1 was used.

[Formula 3-8]

Example 15

Except for using the additive represented by the following formula 3-9 instead of the additive represented by the formula 2-1, it was the same as in Example 1.

[Formula 3-9]

Example 16

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 3-10 was used instead of the additive represented by the formula 2-1.

[Formula 3-10]

Example 17

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 3-11 was used instead of the additive represented by the formula 2-1.

[Formula 3-11]

Example 18

The same procedure as in Example 1 was performed, except that an additive represented by the following formula 3-12 was used instead of the additive represented by the formula 2-1.

[Formula 3-12]

Comparative Example 1

The same procedure as in Example 1 was performed, except that the additive represented by Formula 2-1 was not used.

Comparative Example 2

Except for using KBM-573 (silane coupling agent) instead of the additive represented by Chemical Formula 2-1, the same procedure as in Example 1 was performed.

Comparative Example 3

It was the same as in Example 1, except that the additive represented by the following formula C-1 was used instead of the additive represented by the formula 2-1.

[Formula C-1]

Comparative Example 4

The same procedure as in Example 1 was performed, except that an additive represented by the following formula C-2 was used instead of the additive represented by the formula 2-1.

[Formula C-2]

Comparative Example 5

The same procedure as in Example 1 was performed, except that an additive represented by the following formula C-3 was used instead of the additive represented by the formula 2-1.

[Formula C-3]

Comparative Example 6

Except for using the additive represented by the following formula C-4 instead of the additive represented by the formula 2-1, the same procedure as in Example 1 was used.

[Formula C-4]

(Evaluation 1: Adhesion evaluation)

The photosensitive resin compositions according to Examples 1 to 18 and Comparative Examples 1 to 6 were coated on a Cu wafer to a thickness of 10 μm, respectively, and heated on a hot plate at 120° C. for 4 minutes to form a photosensitive resin film. The photosensitive resin film was cured under nitrogen conditions at 220° C. for 120 minutes.

Adhesion was measured with a die shear tester (DAGE series 4000PXY manufactured by DAGE) by EMC molding on the cured film, and the results are shown in Table 1 below.

Cu wafer die shear test(kgf) Example 1 32 Example 2 32 Example 3 29 Example 4 30 Example 5 31 Example 6 30 Example 7 33 Example 8 35 Example 9 34 Example 10 33 Example 11 35 Example 12 35 Example 13 34 Example 14 33 Example 15 35 Example 16 33 Example 17 33 Example 18 35 Comparative Example 1 13 Comparative Example 2 18 Comparative Example 3 20 Comparative Example 4 19 Comparative Example 5 18 Comparative Example 6 20

(Evaluation 2: Viscosity evaluation)

For the photosensitive resin compositions according to Examples 1 to 18 and Comparative Examples 1 to 6, 5 rpm before and after storage at 23° C. for 1 week (selecting an rpm at which a torque value becomes 50 to 100%) , Brookfield DV- at 25° C. The viscosity was evaluated using a II Pro viscometer and a CPE-52 spindle, and the results are shown in Table 2 below.

Viscosity (cP) before storage at 23°C for 1 week Viscosity (cP) after storage at 23°C for 1 week Example 1 1,010 1,010 Example 2 1006 1,007 Example 3 1,005 1,010 Example 4 1,005 1008 Example 5 1,010 1,015 Example 6 1,000 1,005 Example 7 1,000 1,000 Example 8 1,010 1,015 Example 9 1,014 1,015 Example 10 1,010 1,011 Example 11 1008 1,010 Example 12 1,005 1006 Example 13 1,010 1,010 Example 14 1,001 1,004 Example 15 1,005 1006 Example 16 1,000 1,005 Example 17 1,010 1,011 Example 18 1,010 1,012 Comparative Example 1 1008 1,220 Comparative Example 2 1,010 2,250 Comparative Example 3 1,010 2,350 Comparative Example 4 1,005 2,350 Comparative Example 5 1,005 2,250 Comparative Example 6 1,005 2,300

Through Table 1 and Table 2, it can be seen that the photosensitive resin composition according to an embodiment has very good adhesion to the copper layer. Furthermore, it can be seen that the photosensitive resin compositions according to Comparative Examples 3 to 6 have too high a viscosity to include a silane compound including a thiol group, and thus are not suitable for use as a composition for a semiconductor redistribution layer.

The present invention is not limited to the above embodiments, but can be manufactured in various different forms, and those of ordinary skill in the art to which the present invention pertains can take other specific forms without changing the technical spirit or essential features of the present invention. It will be understood that it can be implemented as Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

Claims (16)

(A) a polyhydroxyamide-based resin comprising a structural unit represented by the following formula (1);
(B) a photopolymerizable compound;
(C) a photoinitiator;
(D) an additive comprising a sulfide linkage or a disulfide linkage and at least one carboxyl group at the terminal; and
(E) solvent
A photosensitive resin composition comprising:
[Formula 1]

In Formula 1,
X ¹ is a residue derived from an anhydride monomer,
Y ¹ is a residue derived from a diamine monomer,
R ¹ and R ² are each 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 hetero it is a ring
The method of claim 1,
The additive is a photosensitive resin composition represented by the following formula 2:
[Formula 2]

In Formula 2,
R ³ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group;
L ¹ is a single bond, a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
L ² is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group.
3. The method of claim 2,
The L ² is a C6 to C20 arylene group substituted or unsubstituted with a carboxyl group. The photosensitive resin composition.
3. The method of claim 2,
The additive represented by Formula 2 is a photosensitive resin composition represented by any one of Formulas 2-1 to 2-6.
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

According to claim 1,
The additive is a photosensitive resin composition represented by the following Chemical Formula 3:
[Formula 3]

In Formula 3,
L ³ to L ⁷ are each independently a single bond, a sulfide linking group, a disulfide linking group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a divalent thiophene linking group, wherein At least one of L ³ to L ⁷ is necessarily a sulfide linking group, a disulfide linking group, or a divalent thiophene linking group.
6. The method of claim 5,
The substituted or unsubstituted C1 to C20 alkylene group is a C1 to C20 alkylene group substituted with a C1 to C10 alkyl group, a C1 to C20 alkylene group substituted with a carboxyl group, or an unsubstituted C1 to C20 alkylene group The photosensitive resin composition.
6. The method of claim 5,
The additive represented by Formula 3 is a photosensitive resin composition represented by any one of Formulas 3-1 to 3-12.
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

[Formula 3-9]

[Formula 3-10]

[Formula 3-11]

[Formula 3-12]

According to claim 1,
The photosensitive resin composition comprising the additive in an amount of 1 to 20 parts by weight based on 100 parts by weight of the polyhydroxyamide-based resin.
According to claim 1,
The anhydride monomer is a photosensitive resin composition represented by the following formula (X-1):
[Formula X-1]

In the formula (X-1),
L ⁸ is a single bond, *-O-*, *-S-*, *-C(=O)-*, *-C(=O)O-*, -*NR ⁴ -*(R ⁴ is hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic linking group, or a combination thereof am.
According to claim 1,
The diamine monomer is a photosensitive resin composition represented by Formula Y-1 or Formula Y-2:
[Formula Y-1]

[Formula Y-2]

In the above formula Y-2,
R ⁵ and R ⁶ 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,
L ⁹ is *-O-* or *-S-*,
n1 and n2 are each independently an integer of 0 to 4.
The method of claim 1,
The photosensitive resin composition,
With respect to 100 parts by weight of the polyhydroxyamide-based resin
The photopolymerizable compound is included in an amount of 1 to 10 parts by weight,
The photopolymerization initiator is included in an amount of 1 to 10 parts by weight,
The additive is included in an amount of 1 to 20 parts by weight,
The solvent is included in 100 parts by weight to 500 parts by weight of the photosensitive resin composition.
According to claim 1,
The photosensitive resin composition further comprises a diacid, an alkanolamine, a leveling agent, a silane coupling agent, a surfactant, an epoxy compound, a thermal latent acid generator, or a combination thereof.
According to claim 1,
The photosensitive resin composition is a negative photosensitive resin composition.
A photosensitive resin film prepared by using the photosensitive resin composition of any one of claims 1 to 13.
15. The method of claim 14,
The photosensitive resin film is a semiconductor redistribution layer insulating film.
A semiconductor device comprising the photosensitive resin film of claim 14 .

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