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 including the photosensitive resin layer, the photosensitive resin composition including a resin wherein the resin includes a polymer represented by Chemical Formula 1. (In Chemical Formula 1, each substituent is as defined in the description). [Chemical Formula 1]

Description

[0001] Cross-reference of related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0119483, filed with the Korean Intellectual Property Office on September 3, 2024, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] With the advent of the hyper-connected intelligent era, featuring artificial intelligence, big data, the Internet of Things, autonomous vehicles, and telemedicine, the development and popularization of smartphones and other electronic devices are accelerating.

[0005] Therefore, 5G communication technology, which can wirelessly transmit ultra-high-speed and large-capacity data, has become more important. In addition, the market size of communication component materials and component elements used in communication devices, including smartphones, is expected to grow exponentially from 2020 to 2026, reaching approximately US$2.3 billion (approximately 14,000 tons / year).

[0006] To minimize propagation loss, dielectric substrates used in 5G communication frequencies (Sub-6 and 28 GHz) require low permittivity (Dk) and low dielectric loss factor (Df), which may not be met by polyimide (PI), primarily used in traditional 4G LTE communications. Ming-Chi Kuo, an analyst at TF International Securities, predicted in 2018 that "modified polyimide (MPI) will replace liquid crystal polymer (LCP) as the mainstream antenna technology for new iPhone models in the second half of the year." This implies that since the manufacturing process for flexible cupper clad laminate (FCCL) is built on production lines using polyimide films (traditional processes), and module manufacturers prefer to perform traditional processes rather than converting devices to use LCP, he hoped that MPI (modified PI) could be rapidly developed and applied. Furthermore, this indicates that MPI, designed to compensate for the shortcomings of LCP, is already under development.

[0007] In other words, the demand for developing polyimide precursor resins with low dielectric constant (Dk) and low dielectric loss factor (Df) has been increasing rapidly recently. Summary of the Invention

[0008] Some embodiments provide a photosensitive resin composition including a resin having excellent reliability and a low dielectric loss factor (Df).

[0009] Some embodiments provide a photosensitive resin layer manufactured using the photosensitive resin composition.

[0010] Some embodiments provide a semiconductor device including the photosensitive resin layer.

[0011] Some embodiments provide a photosensitive resin composition including a resin, wherein the resin includes a polymer represented by Chemical Formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl,

[0016] L 1 is a single bond or a substituted or unsubstituted C1 to C20 alkylene,

[0017] L 2 is a divalent linking group derived from an anhydride,

[0018] L 3 is a divalent linking group including an ester bond (*-C(=O)O-* or *-OC(=O)-*), and

[0019] n is an integer of 1 to 50.

[0020] In Chemical Formula 1, L 2 may be represented by Chemical Formula 2-1 or Chemical Formula 2-2.

[0021] [Chemical Formula 2-1]

[0022]

[0023] [Chemical Formula 2-2]

[0024]

[0025] In Chemical Formula 2-1,

[0026] L 4 is a single bond, an ether linking group (*-O-*) or a substituted or unsubstituted C1 to C20 alkylene.

[0027] In Chemical Formula 1, L 3 may be a divalent linking group including two or more ester linking groups.

[0028] In Chemical Formula 1, L 3 may be represented by Chemical Formula 3.

[0029] [Chemical Formula 3]

[0030]

[0031] In Chemical Formula 3,

[0032] L 5 is an ether linking group (*-O-*) or a substituted or unsubstituted C1 to C20 alkylene, and L 6 is a substituted or unsubstituted C1 to C10 alkylene.

[0033] The polymer represented by Chemical Formula 1 can be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-4.

[0034] [Chemical Formula 1-1]

[0035]

[0036] [Chemical Formula 1-2]

[0037]

[0038] [Chemical Formula 1-3]

[0039]

[0040] [Chemical Formula 1-4]

[0041]

[0042] In Chemical Formula 1-1 to Chemical Formula 1-4,

[0043] L is a substituted or unsubstituted C1 to C10 alkylene, and

[0044] n is an integer of 1 to 50.

[0045] The resin can further include a polymer produced by a polymerization reaction of a diamine compound and a dianhydride compound, and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound can have a structure different from the polymer represented by Chemical Formula 1.

[0046] The diamine compound can be represented by Chemical Formula 4.

[0047] [Chemical Formula 4]

[0048]

[0049] In Chemical Formula 4,

[0050] L 7 is a single bond, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, *-NR 0 -*(R 0 is a substituted or unsubstituted C1 to C10 alkyl group) or a combination thereof.

[0051] The dianhydride compound can be represented by Chemical Formula 5.

[0052] [Chemical Formula 5]

[0053]

[0054] In Chemical Formula 5,

[0055] L 8 is a single bond, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, *-NR 0 -*

[0056] (R 0 is 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.

[0057] The polymer represented by Chemical Formula 1 and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound can be included in a weight ratio of 50:50 to 90:10.

[0058] The photosensitive resin composition can further include a photopolymerizable compound, a photopolymerization initiator, and a solvent.

[0059] The photosensitive resin composition can include, based on 100 parts by weight of the resin, 5 to 20 parts by weight of a photopolymerizable compound, 0.1 to 20 parts by weight of a photopolymerization initiator, and 100 to 500 parts by weight of a solvent.

[0060] The photosensitive resin composition can further include an additive selected from a diacid, an alkanolamine, a leveling agent, a silane coupling agent, a surfactant, an epoxy compound, a thermal latent acid generator, a sensitizer, a radical scavenger, a binder, an organic acid, or a combination thereof.

[0061] The photosensitive resin composition may be a negative photosensitive resin composition.

[0062] The photosensitive resin composition can have a dielectric loss factor (Df) of 0.001 to 0.015 at a frequency of 10 GHz.

[0063] Some embodiments provide photosensitive resin layers manufactured using the photosensitive resin composition.

[0064] Some embodiments provide semiconductor devices including the photosensitive resin layer.

[0065] Other embodiments are included in the following detailed description.

[0066] According to some embodiments, the polymer with a specific structure contained in the resin of the photosensitive resin composition includes (meth)acrylate groups at both ends, which is beneficial for forming a negative pattern, and further includes ester linkage between the two ends, which can ensure low dielectric loss characteristics. Detailed Implementation

[0067] The embodiments will now be described in detail. However, these embodiments are exemplary and this disclosure is not limited thereto.

[0068] In this document, unless otherwise specifically defined, "alkyl" refers to C1 to C20 alkyl, "alkenyl" refers to C2 to C20 alkenyl, "cycloalkenyl" refers to C3 to C20 cycloalkenyl, "heterocyclic alkenyl" refers to C3 to C20 heterocyclic alkenyl, "aryl" refers to C6 to C20 aryl, "aranealkyl" refers to C7 to C20 aranealkyl, "alkylene" refers to C1 to C20 alkylene, "arylene" refers to C6 to C20 arylene, "alkylarylene" refers to C7 to C20 alkylarylene, "heteroarylene" refers to C3 to C20 heteroarylene, and "alkoxide" refers to C1 to C20 alkoxide.

[0069] In this document, unless otherwise specifically defined, "substituted" means that at least one hydrogen atom in a compound is selected from halogen atoms (F, Cl, Br, or I), C1 to C20 alkyl groups substituted with halogen atoms such as trifluoromethyl, hydroxy, C1 to C20 alkoxy, nitro, cyano, amino, imino group, azido group, amidino group, hydrazino group, hydrazono group, carbonyl, carbamyl group, thiol group, etc. Substituents of (meth)acrylate group, ester group, ether group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C20 aryl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl, C3 to C20 cycloalkynyl, C2 to C20 heterocyclic alkyl, C2 to C20 heterocyclic alkenyl, C2 to C20 heterocyclic alkynyl, C3 to C20 heteroaryl, (meth)acrylate group ((meth)acrylate group) or combinations thereof.

[0070] In this document, unless otherwise specifically defined, "heterogeneous" refers to at least one heteroatom in a chemical formula that includes N, O, S, and P.

[0071] In this document, unless otherwise specifically defined, "(meth)acrylate" refers to both "acrylate" and "methacrylate".

[0072] In this document, unless otherwise defined, the term "composite" refers to a mixture or copolymer. Furthermore, "copolymer" refers to block copolymerization, alternating copolymerization, or random copolymerization, and "polymer" refers to block copolymer, alternating copolymer, or random copolymer.

[0073] In this article, unless otherwise specifically defined, unsaturated bonds include not only multiple bonds between carbon atoms, but also those involving other molecules, such as carbonyl bonds and azo bonds.

[0074] In the chemical formulas of this specification, unless otherwise specifically defined, hydrogen bonds are shown at positions where no chemical bond is drawn.

[0075] In this document, unless otherwise defined, "*" refers to the connecting part between the same or different atoms or chemical formulas.

[0076] The photosensitive resin composition according to some embodiments includes a resin comprising a polymer represented by chemical formula 1.

[0077] [Chemical Formula 1]

[0078]

[0079] In chemical formula 1,

[0080] R 1 and R 2 Each is independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

[0081] L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group.

[0082] L 2 It is a divalent linker derived from acid anhydrides.

[0083] L 3 It is a divalent linker including ester bonds (*-C(=O)O-* or *-OC(=O)-*), and

[0084] n is an integer from 1 to 50.

[0085] In order to fix low dielectric constant (Dk) and low dielectric loss factor (Df), many attempts have been made to polymerize various types of polyimide precursor resins. It is known that the higher the fluorine atom content in the molecules that make up the resin and the lower the imide structure content, the easier it is to fix low dielectric constant (Dk) and low dielectric loss factor (Df).

[0086] However, with the advancement of semiconductor technology and the reduction in chip size, there is a need to replace traditional positive polyimide precursor resins with negative polyimide precursor resins, because the latter cannot be cured well at low temperatures and lacks patterning properties.

[0087] Therefore, the inventors have invented a structure for fixing the low dielectric constant (Dk) and low dielectric loss factor (Df) of a negative polyimide precursor resin (or negative resin), instead of a conventional positive polyimide precursor resin. Furthermore, it has been confirmed that the dielectric constant and dielectric loss factor of the negative polyimide precursor resin (or negative resin) can not only be maintained at low levels, for example, a dielectric loss factor (Df) of 0.001 to 0.015 at a frequency of 10 GHz, but also that reliability can be improved due to the ease of forming negative patterns, thus completing the present invention.

[0088] The following is a detailed description of each component.

[0089] (A) Resin

[0090] To ensure the retention of critical reliability properties, such as elongation and glass transition temperature (Tg), key elements in photosensitive resin compositions used as protective films for semiconductor circuits are fixed, polyimide (PI) or polybenzoxazole (PBO) resins are employed. Photosensitive resin compositions incorporating these resins also include photocrosslinking monomers, photopolymerization initiators, etc., to fix excellent protective layer properties and require residue-free processing to achieve excellent patterning, excellent sensitivity characteristics, and storage stability at room temperature for two weeks or longer. Furthermore, when high frequencies must be used to improve the processing speed of electronic devices, materials with low dielectric constant (Dk) and dielectric loss factor (Df) are needed to prevent transmission speed loss.

[0091] According to some embodiments, the resin used in the photosensitive resin composition may be a negative resin, such as a polyimide precursor resin, i.e., a polyamic acid or polyamide ester resin, wherein the polyamic acid or polyamide ester resin may include, but is not limited to, a diamine compound and a polymer produced by the polymerization reaction of a dianhydride compound.

[0092] The negative resin comprises a polymer represented by chemical formula 1, which has been shown to reduce the dielectric constant (Dk) and dielectric loss factor (Df) of the negative photosensitive resin composition at high frequencies.

[0093] For example, in chemical formula 1, L 2 It can be represented by chemical formula 2-1 or chemical formula 2-2.

[0094] [Chemical Formula 2-1]

[0095]

[0096] [Chemical Formula 2-2]

[0097]

[0098] In chemical formula 2-1,

[0099] L 4 It is a single bond, an ether linkage (*-O-*), or a substituted or unsubstituted C1 to C20 alkylene group.

[0100] For example, in chemical formula 2-1, L 4 It can be a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0101] For example, in chemical formula 2-1, L 4 It can be a C1 to C20 alkylene group, either substituted with a halogen group or not substituted with a halogen group. For example, the halogen group can be a fluorine group.

[0102] For example, in chemical formula 1, L 3 It can be a divalent linker comprising two or more ester linkers. In this case, achieving low dielectric loss characteristics may be more advantageous compared to including a single ester linker.

[0103] For example, in the above chemical formula 1, L 3 It can be represented by chemical formula 3, but is not necessarily limited to this.

[0104] [Chemical Formula 3]

[0105]

[0106] In chemical formula 3,

[0107] L 5 It is an ether linkage (*-O-*) or a substituted or unsubstituted C1 to C20 alkylene group, and

[0108] L 6 It is a substituted or unsubstituted C1 to C10 alkylene group.

[0109] Even when a cured layer (insulating layer, resin layer) is manufactured using a negative photosensitive resin composition with a low dielectric loss factor, it may be difficult to apply it to semiconductor devices if its physical properties, such as adhesion to metal layers or reliability, such as heat resistance, are poor. However, the photosensitive resin composition according to one embodiment, because it includes a polymer having the structure represented by Formula 1 as an essential component, can still have a low dielectric loss factor and excellent reliability despite being a negative composition.

[0110] For example, a polymer represented by chemical formula 1 can be represented by any of chemical formulas 1-1 to 1-4, but is not necessarily limited to this.

[0111] [Chemical Formula 1-1]

[0112]

[0113] [Chemical Formula 1-2]

[0114]

[0115] [Chemical Formulas 1-3]

[0116]

[0117] [Chemical Formulas 1-4]

[0118]

[0119] In chemical formulas 1-1 to 1-4

[0120] L is a substituted or unsubstituted C1 to C10 alkylene group, and

[0121] n is an integer from 1 to 50.

[0122] Furthermore, the resin may include another polymer having a different structure than the polymer represented by Formula 1. In this case, the other polymer may be a polymer produced by the polymerization of a diamine compound and a dianhydride compound. In this scenario, elongation can be improved while maintaining low dielectric loss characteristics.

[0123] For example, polymers produced by the polymerization of diamine compounds and dianhydride compounds may include functional groups represented by chemical formula 6.

[0124] [Chemical Formula 6]

[0125]

[0126] In chemical formula 6,

[0127] R 9 It is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and

[0128] L 9 It is a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

[0129] For example, polymers represented by Formula 1 and polymers produced by the polymerization of diamine compounds and dianhydride compounds can be included in a weight ratio of 50:50 to 90:10. In this case, the increase in the dielectric loss factor of the photosensitive resin composition can be suppressed while maximizing the improvement of elongation.

[0130] For example, diamine compounds can be represented by chemical formula 4, but are not necessarily limited to this.

[0131] [Chemical Formula 4]

[0132]

[0133] In chemical formula 4,

[0134] L 7 For *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-NR 0 -*(R 0 It is a substituted or unsubstituted C1 to C10 alkyl group or a combination thereof.

[0135] For example, dianhydride compounds can be represented by chemical formula 5, but are not necessarily limited to this.

[0136] [Chemical Formula 5]

[0137]

[0138] In chemical formula 5,

[0139] L 8 It is a single bond, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, *-NR 0 -*

[0140] (R 0 It is 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 linker, or a combination thereof.

[0141] For example, when L 8 When the value is *-C≡C-*, the heat resistance, adhesion, and reliability of the cured layer (insulating layer, resin film) can be further improved.

[0142] For example, dianhydride compounds can be, but are not necessarily limited to, pyromellitic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, etc.

[0143] The polymer represented by Formula 1 has a weight-average molecular weight (Mw) ranging from 3,000 g / mol to 300,000 g / mol. In this case, sufficient physical properties are obtained, and excellent solubility in organic solvents makes processing easy.

[0144] (B) Photopolymerizable compounds

[0145] 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.

[0146] Photopolymerizable compounds can be compounds containing at least two functional groups represented by chemical formula 6.

[0147] [Chemical Formula 6]

[0148]

[0149] In chemical formula 6,

[0150] R9 It is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and

[0151] L 9 It is a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

[0152] For example, a compound containing at least two functional groups represented by Formula 6 may include two to six functional groups represented by Formula 4. In this case, sufficient polymerization can be induced during exposure in the patterning process, thereby forming a pattern with excellent heat resistance, light resistance, and chemical resistance.

[0153] For example, a compound containing at least two functional groups represented by chemical formula 6 can be a compound represented by any one of chemical formulas 7 to 9, but is not limited to this.

[0154] [Chemical Formula 7]

[0155]

[0156] [Chemical Formula 8]

[0157]

[0158] [Chemical Formula 9]

[0159]

[0160] In chemical formulas 7 to 9

[0161] p, q, r, s, and t are each an independent integer from 1 to 10.

[0162] When the photopolymerizable compound is a mixture of two different compounds, the other of the two compounds can be a monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one olefinically unsaturated double bond.

[0163] Monofunctional or polyfunctional ester compounds of (meth)acrylic acid having at least one olefinically unsaturated double bond can 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-hexanediol di(meth)acrylate, etc.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 Aepoxy(meth)acrylate, ethylene glycol monomethyl ether(meth)acrylate, trimethylolpropanetri(meth)acrylate, tris(meth)acryloyloxyethylphosphate, phenolic epoxy(meth)acrylate, or combinations thereof.

[0164] Commercially available monofunctional or polyfunctional ester compounds of (meth)acrylic acid having at least one olefinically unsaturated double bond are as follows. Examples of monofunctional esters of (meth)acrylic acid include: (Toagosei Chemistry Industry Co., Ltd.) (Nippon Kayaku Co., Ltd.); (Osaka Organic Chemical Industry Co., Ltd.) etc. Examples of difunctional esters of (meth)acrylic acid may include Aronix. (Tosei Chemical Industry Co., Ltd.), KAYARAD (Nippon Kayaku Co., Ltd.), (Osaka Organic Chemical Industry Co., Ltd.), etc. Examples of trifunctional esters of (meth)acrylic acid may include Aronix. (Tosei Chemical Industry Co., Ltd.)

[0165] (Nippon Kayaku Co., Ltd.), (Osaka Yuki Kayaku Kogyo Co., Ltd., etc.) It can be used alone or in combination with two or more other products.

[0166] Photopolymerizable compounds can be used after treatment with acid anhydrides to provide better developability.

[0167] Based on 100 parts by weight of resin, the photopolymerizable compound may be included in an amount of 5 to 20 parts by weight, for example, 7 to 15 parts by weight. If the photopolymerizable compound is included within the above range, the curing is sufficient, the reliability is excellent, the heat resistance, light resistance and chemical resistance of the pattern are improved, and the resolution and adhesion are also improved.

[0168] (C) Photopolymerization initiator

[0169] According to some embodiments, the photosensitive resin composition may further include a photopolymerization initiator. The photopolymerization initiator may be an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, etc.

[0170] 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.

[0171] Examples of benzophenone compounds 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, etc.

[0172] Examples of thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, etc.

[0173] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, etc.

[0174] Examples of triazine compounds 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, and 2-(naphtho1-yl)-4,6-bis(trichloromethyl)-s-triazine. (hyl)-s-triazine, 2-(4-methoxynaphtho1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc.

[0175] Examples of oxime compounds may include O-acyloxime compounds, 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. Specific examples of O-acyl oxime compounds may include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-but-1-one, 1-(4-phenylthiophenyl)-but-1,2-dione-2-oxime-O-benzoate (1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate), and 1-(4-phenylthiophenyl)-oct-1,2-dione-2-oxime-O-benzoate (1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate). (nylsulfanylphenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butane-1-oneoxime-O-acetate.

[0176] In addition to the compounds mentioned above, photoinitiators may include carbazole compounds, diketone compounds, sulfonium borate-based compounds, diazo compounds, imidazole compounds, biimidazole-based compounds, and fluorene-based compounds.

[0177] Based on 100 parts by weight of resin, the photopolymerization initiator may be included in an amount of 0.1 to 20 parts by weight, for example, 1 to 10 parts by weight, for example, 1 to 7 parts by weight. When the photopolymerization initiator is included within the above range, the photopolymerization reaction occurs sufficiently, resulting in excellent sensitivity and improved light transmittance.

[0178] (D) Solvent

[0179] The solvent can be a material that is compatible with resins, photopolymerizable compounds, and photopolymerization initiators but does not react with them.

[0180] Examples of solvents can include alcohols, such as methanol and ethanol; ethers, such as dichloroethyl ether, n-butyl ether, diisopentyl ether, methyl phenyl ether, tetrahydrofuran, etc.; ethylene glycol ethers, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, etc.; cellolsolve acetates, such as methyl cellolsolve acetate, ethyl cellolsolve acetate, diethyl cellolsolve acetate, etc.; carbitol, 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 (propylene... Glycol alkyl ether acetate, 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-pentanone, 2-heptanone, etc.; saturated aliphatic monocarboxylic acid alkyl esters, such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactate 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 3-oxymethylpropionate, ethyl 3-oxypropionate, etc.; 3-alkoxypropionic acid alkyl esters, for example... Examples of esters include 3-methoxymethylpropionate, 3-methoxyethylpropionate, 3-ethoxyethylpropionate, and 3-ethoxymethylpropionate; alkyl 2-oxypropionates, such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; alkyl 2-alkoxypropionates, such as 2-methoxymethylpropionate, 2-methoxyethylpropionate, 2-ethoxyethylpropionate, and 2-ethoxymethylpropionate; alkyl 2-oxy-2-methylpropionates, such as 2-oxy-2-methylmethylpropionate and 2-oxy-2-methylethylpropionate; monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylalkylpropionates, such as 2-methoxy-2-methylmethylpropionate and 2-ethoxy-2-methylethylpropionate; esters, such as 2-hydroxyethylpropionate, 2-hydroxy-2-methylethylpropionate, hydroxyethyl acetate, and methyl 2-hydroxy-3-methylbutyrate; and keto esters, such as ethyl pyruvate. (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, phenyl acetate, and other cell solvents can also be used.

[0181] Based on 100 parts by weight of resin, the solvent may be included in the range of 100 to 500 parts by weight. If the solvent is included in this range, the photosensitive resin composition has a suitable viscosity, thereby exhibiting excellent processability in the manufacture of the photosensitive resin layer.

[0182] (E) Other additives

[0183] According to some embodiments, the photosensitive resin composition may also include other additives.

[0184] Photosensitive resin compositions may include additives such as diacids (e.g., malonic acid, etc.), alkanolamines (e.g., 3-amino-1,2-propanediol, N-phenyldiethanolamine, etc.), leveling agents, silane coupling agents, surfactants, epoxy compounds, latent acid generators, developer control agents, curing agents, sensitizers, free radical scavengers, binders, organic acids, or combinations thereof, to prevent stains or spots during coating, provide leveling properties, or prevent residues due to undeveloped material. The amount of these additives used can be easily adjusted according to the desired physical properties.

[0185] For example, silane coupling agents can have reactive substituents such as vinyl, carboxyl, methacryloyloxy, isocyanate, or epoxy groups to improve adhesion to the substrate, and have a structure different from that of silane compounds.

[0186] Examples of silane coupling agents may include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. These can be used alone or in combination of two or more.

[0187] Based on 100 parts by weight of the photosensitive resin composition, the content of the silane coupling agent can be from 0.01 parts by weight to 10 parts by weight. If the silane coupling agent is included within the above range, adhesion, storage properties, etc., are improved.

[0188] For example, surfactants may be added to prevent uneven film thickness or improve developability. These surfactants may include fluorinated surfactants and / or silicone-based surfactants.

[0189] Examples of fluorinated surfactants include commercially available fluorinated surfactants, such as those from BM Chemicals Inc. etc.; Dainippon Ink Kagaku Kogyo Co., Ltd.

[0190] etc.; FULORAD of Sumitomo 3M Co.,Ltd.

[0191]

[0192] etc.; Asahi Glass Co., Ltd. etc.; Toray Silicone Co., Ltd. wait.

[0193] Silicone surfactants can be commercially available silicone surfactants, such as BYK Chem's BYK-307, BYK-333, BYK-361N, BYK-051, BYK-052, BYK-053, BYK-067A, BYK-077, BYK-301, BYK-322, BYK-325, and BYK-378.

[0194] Based on 100 parts by weight of the photosensitive resin composition, the surfactant can be used in an amount from 0.001 parts by weight to 5 parts by weight. If the surfactant is included within the above range, uniform coating can be ensured, stains will not occur, and coating performance on ITO or glass substrates, Si wafers, or SiN substrates can be improved. x Wetting properties on the wafer and Cu substrate.

[0195] Furthermore, the photosensitive resin composition further includes an epoxy compound to improve adhesion to the substrate, etc. Examples of epoxy compounds may include phenolic varnish epoxy compounds, tetramethylbiphenyl epoxy compounds, bisphenol A epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

[0196] Based on 100 parts by weight of the photosensitive resin composition, the epoxy compound can be used in an amount from 0.01 parts by weight to 5 parts by weight. When the epoxy compound is included in the above range, properties such as shelf life and adhesion can be improved.

[0197] In addition, the photosensitive resin composition may also include a latent acid generating agent. Examples of latent acid generating agents may include aryl sulfonic acids, such as p-toluenesulfonic acid and benzenesulfonic acid; perfluoroalkyl sulfonic acids, such as trifluoromethanesulfonic acid, trifluorobutyric acid, etc.; alkyl sulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, butyric acid, etc.; or combinations thereof, but not limited thereto.

[0198] In addition, the photosensitive resin composition may further include organic acids, such as citric acid, to improve low dielectric loss characteristics.

[0199] In addition, the photosensitive resin composition may contain a predetermined amount of antioxidants, stabilizers, and other additives, provided that the properties of the photosensitive resin composition are not degraded.

[0200] Some embodiments provide a photosensitive resin layer manufactured by exposing, developing, and curing the aforementioned photosensitive resin composition.

[0201] The photosensitive resin layer can be, for example, a semiconductor redistribution layer insulating layer, but is not limited to this; any curing layer suitable for electronic devices can be used.

[0202] The method for manufacturing the photosensitive resin layer is as follows.

[0203] (1) Coating and film formation

[0204] A photosensitive resin composition is coated onto a pre-treated glass substrate, ITO substrate, Si wafer, SiNx wafer, Cu substrate, or other substrate using spin coating, slot coating, roller coating, screen-printing, or applicator methods to achieve a desired thickness. The coating is then heated at 70°C to 150°C for 1 to 10 minutes to remove the solvent, thereby forming a film.

[0205] (2) Exposure

[0206] After a mask is applied to the obtained photosensitive resin layer to form the desired pattern, it is exposed to photochemical rays of 200 to 500 nanometers. As the light source for irradiation, low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, argon lasers, etc., can be used, and in some cases, X-rays, electron beams, etc., can also be used.

[0207] The exposure dose varies depending on the type of components in the composition, the mixing amount, and the dry film thickness, but is less than 500 mJ / cm when using a high-pressure mercury lamp. 2 (Based on a 365-nanometer sensor).

[0208] (3) Development

[0209] In the development method, after the exposure step, an alkaline aqueous solution or organic solvent is used as a developer to dissolve and remove unwanted parts, leaving only the exposed parts to form a pattern.

[0210] (4) Post-processing

[0211] A post-heating process is employed to obtain patterns with excellent heat resistance, lightfastness, adhesion, crack resistance, chemical resistance, high strength, and storage stability in the image pattern developed in the above process. For example, after development, the pattern can be heated in an oven at 200°C to 400°C under a nitrogen atmosphere for more than 1 hour.

[0212] Some exemplary embodiments provide electronic devices including a photosensitive resin layer.

[0213] The electronic device may be, for example, a semiconductor device, but is not necessarily limited to this.

[0214] Hereinafter, preferred embodiments of the present invention will be described. However, the following embodiments are merely preferred embodiments of the present invention, and the present invention is not limited to the following embodiments.

[0215] (Example)

[0216] (Resin Synthesis)

[0217] Comparative Synthesis Example 1

[0218] 18.98 g (65 mmol) of 3,3,4,4-biphenyltetracarboxylic dianhydride (BPDA), 17.72 g (136 mmol) of 2-hydroxyethyl methacrylate (HEMA), and a catalytic amount of DBU (1,8-diazabicyclo[5.4.0]undeca-7-ene) were dissolved in N-methyl-2-pyrrolidone in an amount four times that of pyromellitic dianhydride, and then stirred at room temperature for 48 hours to obtain ester solution 1.

[0219] In addition, 46.35 g (149 mmol) of 4,4'-oxydiphthalic anhydride (ODPA), 42 g (323 mmol) of 2-hydroxyethyl methacrylate (HEMA), and a catalytic amount of DBU were dissolved in N-methyl-2-pyrrolidone in an amount four times that of 4,4'-oxydiphthalic anhydride (ODPA), and then stirred at room temperature for 48 hours to obtain ester solution 2. Ester solutions 1 and 2 were mixed, and while cooling the mixture in an ice bath, 2.2 equivalents of thionyl chloride based on the total amount of the BPDA-HEMA and ODPA-HEMA ester solutions were added dropwise, followed by stirring for 1 hour to prepare an acid chloride solution.

[0220] Subsequently, 100 mmol of 4,4'-oxydianiline (ODA) and pyridine in an amount twice the equivalent of thionyl chloride were dissolved in four times the amount of ODA in N-methyl-2-pyrrolidone to prepare a solution. This solution was added dropwise to an acidic chloride solution while being cooled in an ice bath. After the addition was complete, the reaction solution was added dropwise to distilled water to form a precipitate. The precipitate was separated by filtration, collected, washed twice with distilled water, and vacuum dried to obtain polyamic acid ester. The obtained polymer (polyamic acid ester) had a weight-average molecular weight of 25,000 g / mol.

[0221] Synthesis example 1

[0222] While purging with nitrogen, 0.58 mol of 4,4'-oxophthalic anhydride (ODPA) monomer was added to 600 g of γ-butyrolactone (GBL) in a four-necked flask equipped with a stirrer, temperature controller, nitrogen injection device, and condenser. Then, 1.22 mol of 2-hydroxyethyl methacrylate (HEMA) was added. While stirring the mixture at room temperature, 1.16 mol of pyridine was added to obtain a reaction mixture. The reaction mixture was reacted at room temperature for 16 hours and then cooled to -10°C. A solution prepared by dissolving 1.17 mol of dicyclohexylcarbodiimide (DCC) in 250 g of GBL was added dropwise over 30 minutes. After an additional 5 minutes of stirring, a solution of 0.54 mol of diamine monomer (represented by formula B) and 300 g of GBL was added over 40 minutes, followed by an additional 2 hours of stirring.

[0223] (Chemical formula B)

[0224]

[0225] Subsequently, after reacting at room temperature for 1 hour, 30g of a monomer represented by chemical formula C was added, and then the mixture was stirred for 1 hour.

[0226] (Chemical formula C)

[0227]

[0228] Subsequently, GBL was added to the reaction solution to achieve a solids content of 18%, followed by the addition of 3 liters of ethanol to obtain a precipitate. The polymer was separated by filtration, dissolved in 1.5 liters of tetrahydrofuran (THF), and then added dropwise to 30 liters of water to form a precipitate. The precipitate was separated by filtration and dried under vacuum. The obtained precipitate was dried under reduced pressure at 50°C for 24 hours or longer to prepare the polymer represented by chemical formula 1-1 (weight average molecular weight: 22,000 g / mol) (L = unsubstituted ethylene).

[0229] [Chemical Formula 1-1]

[0230]

[0231] Synthesis example 2

[0232] The polymer represented by chemical formulas 1-2 (weight average molecular weight: 22,000 g / mol) (L = unsubstituted ethylene) was obtained in the same manner as in Synthesis Example 1, except that 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) was used instead of the 4,4'-oxophthalic anhydride (ODPA) monomer in Synthesis Example 1.

[0233] [Chemical Formula 1-2]

[0234]

[0235] Synthesis example 3

[0236] The polymer represented by chemical formulas 1-3 (weight average molecular weight: 22,000 g / mol) (L = unsubstituted ethylene) was obtained in the same manner as in Synthesis Example 1, except that 3,3,4,4-biphenyltetracarboxylic dianhydride (BPDA) was used instead of the 4,4'-oxophthalic anhydride (ODPA) monomer in Synthesis Example 1.

[0237] [Chemical Formulas 1-3]

[0238]

[0239] Synthesis example 4

[0240] The polymer represented by chemical formulas 1-4 (weight average molecular weight: 22,000 g / mol) (L = unsubstituted ethylene) was obtained in the same manner as in Synthesis Example 1, except that pyromellitic dianhydride was used instead of the 4,4'-oxophthalic anhydride (ODPA) monomer in Synthesis Example 1.

[0241] [Chemical Formulas 1-4]

[0242]

[0243] (Preparation of photosensitive resin composition)

[0244] Comparative Example 1

[0245] 33.28 g of the polymer from Comparative Synthesis Example 1 was mixed with 3.69 g of tetraethylene glycol dimethacrylate, followed by the addition of 1.66 g of photopolymerization initiator (PBG305, TRONLY), 3.32 g of sensitizer (N-phenyldiethanolamine), 0.55 g of free radical scavenger (CX-1790), 0.92 g of adhesion promoter A-187, 0.18 g of citric acid, 50.76 g of GBL, and 5.64 g of DMSO, and then stirred thoroughly. The mixture was subsequently filtered through a 0.45 μm polypropylene resin filter to obtain a negative photosensitive resin composition.

[0246] Example 1

[0247] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 16.64 g of the polymer of Comparative Synthesis Example 1 and 16.64 g of the polymer of Synthesis Example 1 (weight ratio of 50:50).

[0248] Example 2

[0249] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 3.328 g of the polymer of Comparative Example 1 and 29.952 g of the polymer of Comparative Example 1 (weight ratio of 10:90).

[0250] Example 3

[0251] The photosensitive resin composition was obtained in the same manner as in Comparative Example 1, except that the polymer of Synthetic Example 1 was used instead of the polymer of Comparative Synthetic Example 1.

[0252] Example 4

[0253] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 16.64 g of the polymer of Comparative Synthesis Example 1 and 16.64 g of the polymer of Synthesis Example 2 (weight ratio of 50:50).

[0254] Example 5

[0255] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 16.64 g of the polymer of Comparative Synthesis Example 1 and 16.64 g of the polymer of Synthesis Example 3 (weight ratio of 50:50).

[0256] Example 6

[0257] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 16.64 g of the polymer of Comparative Synthesis Example 1 and 16.64 g of the polymer of Synthesis Example 4 (weight ratio of 50:50).

[0258] Example 7

[0259] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that a mixture of 1.664 g of the polymer of Comparative Synthesis Example 1 and 31.616 g of the polymer of Synthesis Example 1 (weight ratio of 5:95) was used instead of 33.28 g of the polymer of Comparative Synthesis Example 1.

[0260] Example 8

[0261] The photosensitive resin composition was obtained in the same manner as Comparative Example 1, except that 33.28 g of the polymer of Comparative Example 1 was replaced with a mixture of 18.304 g of the polymer of Comparative Example 1 and 14.976 g of the polymer of Comparative Example 1 (weight ratio of 55:45).

[0262] (evaluate)

[0263] Each photosensitive resin composition was spin-coated onto an 8-inch silicon wafer and then pre-baked at 100°C for 4 minutes to obtain a 10.0 μm thick film. After cooling at room temperature for 60 seconds, the wafer was irradiated with light for 700 msec using an i-line stepper (NSR-2005i10C, Nikon Inc.) to induce photocuring in the photosensitive areas. The exposed substrate was developed twice at room temperature using a puddle method with 100% cyclopentanone solvent for 60 seconds each time, followed by washing with 100% PGMEA solvent for 60 seconds. Subsequently, the developed wafer was cured in a nitrogen atmosphere at 220°C for 2 hours to obtain the photosensitive resin layer (film).

[0264] (1) Dielectric loss factor evaluation: The obtained film was pretreated by drying at 130℃ for 30 minutes and then aged in a constant temperature and humidity chamber at 23℃ and 50% relative humidity for 24 hours. The dielectric loss factor (Df) of the obtained film was then evaluated. Subsequently, the dielectric properties of the film were measured at a frequency of 10 GHz using an ENA manufactured by Keysight and a split post-dielectric resonator (SPDR) method. The results are shown in Table 1.

[0265] (2) Elongation evaluation: The cured film was immersed in 1% HF solution for 1 hour to prepare PID film samples. Each sample was cut into 1cm*10cm pieces, and the elongation was measured at room temperature (25℃) using a tensile tester (HZ-1003) manufactured by Shimazu Corp. The results are shown in Table 1.

[0266] (3) Reliability assessment: The cured film was subjected to 2000 thermal cycles (-55℃–125℃), which is a reliability condition. Subsequently, FE-SEM was used to check whether cracks appeared between the film and Cu. The results are shown in Table 1.

[0267] (Table 1)

[0268]

[0269] Referring to Table 1, the photosensitive resin compositions according to some embodiments exhibit low dielectric loss factors as well as excellent elongation and reliability.

[0270] While this disclosure has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather 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 exemplary and not as limiting the invention in any way.

Claims

1. A photosensitive resin composition, comprising a resin, wherein the resin comprises a polymer represented by Chemical Formula 1: [Chemical Formula 1] wherein in Chemical Formula 1, R 1 and R 2 each independently is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, L 1 is a single bond or substituted or unsubstituted C1to C20alkylene, L 2 for divalent linking groups derived from anhydrides, L 3 a divalent linking group comprising an ester bond, wherein the ester bond is *-C(=0)0-* or *-OC(=0)-*, and n is an integer of 1 to 50. 2.The photosensitive resin composition according to claim 1, wherein L 2 represented by Chemical Formula 2-1 or Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] wherein in Chemical Formula 2-1, L 4 is a single bond, an ether linkage, or a substituted or unsubstituted C1to C20alkylene.

3. The photosensitive resin composition according to claim 1, wherein L 3 is a divalent linking group comprising two or more ester linking groups.

4. The photosensitive resin composition according to claim 1, wherein L 3 is represented by Chemical Formula 3: [Chemical Formula 3] wherein in Chemical Formula 3, L 5 is an ether linker or a substituted or unsubstituted C1to C20alkylene, and L 6 is a substituted or unsubstituted C1to C10alkylene. 5.The photosensitive resin composition according to claim 1, wherein the polymer represented by Chemical Formula 1 is represented by any one of Chemical Formulae 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] wherein in Chemical Formulae 1-1 to 1-4, L is a substituted or unsubstituted C1 to C10 alkylene, and n is an integer of 1 to 50. 6.The photosensitive resin composition according to claim 1, wherein the resin further comprises a polymer produced by a polymerization reaction of a diamine compound and a dianhydride compound, and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound has a different structure from the polymer represented by Chemical Formula 1. 7.The photosensitive resin composition according to claim 6, wherein the diamine compound is represented by Chemical Formula 4: [Chemical Formula 4] wherein in Chemical Formula 4, L 7 is *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-NR 0 or combinations thereof, R 0 is a substituted or unsubstituted C1to C10alkyl. 8.The photosensitive resin composition according to claim 6, wherein the dianhydride compound is represented by Chemical Formula 5: [Chemical Formula 5] wherein in Chemical Formula 5, L 8 is a single bond, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, *-NR 0 -* substituted or unsubstituted C1to C20alkylene, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C20heterocyclic linker, or a combination thereof, R 0 is substituted or unsubstituted C1to C10alkyl. 9.The photosensitive resin composition according to claim 6, wherein the polymer represented by Chemical Formula 1 and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound are included in a weight ratio of 50:50 to 90:

10. 10.The photosensitive resin composition according to claim 6, wherein the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound comprises a functional group represented by Chemical Formula 6: [Chemical Formula 6] wherein in Chemical Formula 6, R 9 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group, and L 9 is a single bond or substituted or unsubstituted C1to C10alkylene. 11.The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition further comprises a photopolymerizable compound, a photopolymerization initiator, and a solvent. 12.The photosensitive resin composition according to claim 11, wherein the photosensitive resin composition comprises, based on 100 parts by weight of the resin, 5 to 20 parts by weight of the photopolymerizable compound, 0.1 to 20 parts by weight of the photopolymerization initiator, 100 to 500 parts by weight of the solvent. 13.The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition is a negative photosensitive resin composition. 14.The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition has a dielectric loss tangent of 0.001 to 0.015 at a frequency of 10 GHz. 15.A photosensitive resin layer manufactured using the photosensitive resin composition according to claim 1. 16.A semiconductor device comprising the photosensitive resin layer according to claim 15.

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