Photosensitive resin composition, photosensitive resin film, and semiconductor device

Abstract

To provide a photosensitive resin composition containing a resin that is excellent in reliability and has a low dielectric tangent (Df). 【Solution means】The photosensitive resin composition contains a resin, and the resin contains a polymer represented by the following Chemical Formula 1. [Chemical Formula 1] 【Chemical Formula 1】 JPEG2026047027000044.jpg34166 (In the above Chemical Formula 1, R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group, L 1 is a single bond or a substituted or unsubstituted C1-C20 alkylene group, L 2 is a divalent linking group derived from an acid anhydride, L 3 is a divalent linking group containing an ester linking group (*-C(=O)O-* or *-OC(=O)-*), and n is an integer of 1 to 50.)

Description

[Technical Field]

[0001] This disclosure relates to a photosensitive resin composition, a photosensitive resin film utilizing the same, and a semiconductor device. [Background technology]

[0002] As we enter an era of hyper-connected intelligence, encompassing artificial intelligence, big data, IoT, autonomous vehicles, and telemedicine, the development and widespread adoption of diverse electronic devices such as smartphones are accelerating.

[0003] As a result, the importance of 5G communication technology, which enables the wireless transmission of ultra-high-speed, large-capacity data, has become enormous. The market size for communication components, materials, and elements used in communication devices, including smartphones, is projected to expand explosively from 2020 to 2026, reaching approximately US$2.3 billion (14,000 tons / year).

[0004] For dielectric substrates used in 5G communication frequency bands (Sub-6 and 28GHz), the dielectric constant (Dk) and dielectric loss tangent (Df) must be as low as possible to minimize radio wave loss. Therefore, the use of polyimide (PI), which was mainly used in existing 4G LTE communications, is difficult.

[0005] In 2018, TF International analyst Ming-Chi Kuo stated that he expected "modified polyimide (MPI) to replace liquid crystal polymer (LCP) and become the main antenna technology for new iPhone® models in the second half of the year." This can be interpreted as meaning that the manufacturing process for flexible copper-clad laminates (FCCL) is structured using polyimide film (existing process), and module companies prefer to use the existing process rather than modifying their equipment for LCP-using processes, thus hoping that MPI will be developed and quickly applied. It also suggests that MPI, which complements the shortcomings of LCP, has already been developed.

[0006] That is, the need to develop polyimide precursor resins having a low dielectric constant (Dk) and a low dielectric tangent (Df) has recently been increasing rapidly.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] One object of one embodiment is to provide a photosensitive resin composition containing a resin having excellent reliability and a low dielectric tangent (Df).

[0009] Another object of another embodiment is to provide a photosensitive resin film manufactured using the photosensitive resin composition.

[0010] Another object of another embodiment is to provide a semiconductor device including the photosensitive resin film.

Means for Solving the Problems

[0011] One embodiment provides a photosensitive resin composition containing a resin, and the resin contains a polymer represented by the following Chemical Formula 1.

[0012] [Chemical Formula 1]

Chem.

[0013] In Chemical Formula 1 above, R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group, L 1is a single bond or a substituted or unsubstituted C1-C20 alkylene group, L 2 is a divalent linking group derived from an acid anhydride, L 3 is a divalent linking group containing an ester linking group (*-C(=O)O-* or *-OC(=O)-*), n is an integer from 1 to 50.

[0014] In Chemical Formula 1 above, L 2 may be represented by the following Chemical Formula 2-1 or Chemical Formula 2-2.

[0015] [Chemical Formula 2-1]

Chemical Structure

[0016] [Chemical Formula 2-2]

Chemical Structure

[0017] In the above Chemical Formula 2-1, L 4 is a single bond, an ether linking group (*-O-*) or a substituted or unsubstituted C1-C20 alkylene group.

[0018] In Chemical Formula 1 above, L 3 may be a divalent linking group containing two or more ester linking groups.

[0019] In Chemical Formula 1 above, L 3 may be represented by the following Chemical Formula 3.

[0020] [Chemical Formula 3]

Chemical Structure

[0021] In the above Chemical Formula 3, L 5This is an ether linking group (*-O-*) or a substituted or unsubstituted C1-C20 alkylene group. L 6 These are substituted or unsubstituted C1-C10 alkylene groups.

[0022] The polymer represented by the above chemical formula 1 may also be represented by any one of the following chemical formulas 1-1 to 1-4.

[0023] [Chemical formula 1-1] [ka]

[0024] [Chemical formula 1-2] [ka]

[0025] [Chemical formula 1-3] [ka]

[0026] [Chemical formula 1-4] [ka]

[0027] In the above chemical formulas 1-1 to 1-4, L is a substituted or unsubstituted C1-C10 alkylene group. n is an integer between 1 and 50.

[0028] The resin further comprises a polymer produced by a polymerization reaction between a diamine compound and a dianhydride compound, and the polymer produced by the polymerization reaction between the diamine compound and the dianhydride compound may have a different structure from the polymer represented by the above chemical formula 1.

[0029] The diamine compound may also be represented by the following chemical formula 4.

[0030] [Chemical formula 4] [ka]

[0031] In the above chemical formula 4, L 7 *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-NR 0 -*(R 0 This is a substituted or unsubstituted C1-C10 alkyl group, or a combination thereof.

[0032] The dianhydride compound may also be represented by the following chemical formula 5.

[0033] [Chemical formula 5] [ka]

[0034] In the above chemical formula 5, L 8 These are single bonds, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, and *-NR 0 -*(R 0 These are substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C1-C20 alkylene groups, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C2-C20 heterocyclic linking groups, or combinations thereof.

[0035] The polymer represented by the above chemical formula 1, and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound may be included in a weight ratio of 50:50 to 90:10.

[0036] The photosensitive resin composition may further contain a photopolymerizable compound, a photopolymerization initiator, and a solvent.

[0037] The photosensitive resin composition may contain 5 to 20 parts by weight of the photopolymerizable compound, 0.1 to 20 parts by weight of the photopolymerization initiator, and 100 to 500 parts by weight of the solvent per 100 parts by weight of the resin.

[0038] The photosensitive resin composition may further contain additives such as diacides, alkanolamines, leveling agents, silane coupling agents, surfactants, epoxy compounds, thermal latent acid generators, sensitizers, radical scavengers, adhesives, organic acids, or combinations thereof.

[0039] The photosensitive resin composition may be a negative-type photosensitive resin composition.

[0040] The photosensitive resin composition can have a dielectric loss tangent (Df) of 0.001 to 0.015 at a frequency of 10 GHz.

[0041] Another embodiment provides a photosensitive resin film manufactured using a photosensitive resin composition.

[0042] Another embodiment provides a semiconductor device including a photosensitive resin film.

[0043] Other specific aspects of the present invention are included in the detailed description below. [Effects of the Invention]

[0044] In one embodiment, a polymer of a specific structure contained in the resin of a photosensitive resin composition contains (meth)acrylate groups at both ends, facilitating the formation of a negative pattern, and further includes an ester linking group between the two ends, enabling the securing of low dielectric loss tangent properties. [Modes for carrying out the invention]

[0045] Embodiments of the present invention will be described in detail below. However, these are presented as examples only and the present invention is not limited thereto, and the present invention is defined solely within the scope of the claims described below.

[0046] Unless otherwise specified herein, “alkyl group” means a C1-C20 alkyl group, “alkenyl group” means a C2-C20 alkenyl group, “cycloalkenyl group” means a C3-C20 cycloalkenyl group, “heterocycloalkenyl group” means a C3-C20 heterocycloalkenyl group, “aryl group” means a C6-C20 aryl group, “arylalkyl group” means a C7-C20 arylalkyl group, “alkylene group” means a C1-C20 alkylene group, “arylene group” means a C6-C20 arylene group, “alkylarylene group” means a C7-C20 alkylarylene group, “heteroarylene group” means a C3-C20 heteroarylene group, and “alkoxylene group” means a C1-C20 alkoxylene group.

[0047] Unless otherwise specified herein, “substitution” means a C1-C20 alkyl group, hydroxyl group, C1-C20 alkoxy group, nitro group, cyano group, amine group, imino group, azide group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamoyl group, thiol group, ester group, ether group, carboxyl group or its salts, sulfonic acid group or its salts, etc., in which at least one hydrogen atom is substituted with a halogen atom (F, Cl, Br, I), trifluoromethyl group or other halogen atom. This means that the molecule is substituted with substituents of acid or its salts, C1-C20 alkyl groups, C2-C20 alkenyl groups, C2-C20 alkynyl groups, C6-C20 aryl groups, C3-C20 cycloalkyl groups, C3-C20 cycloalkenyl groups, C3-C20 cycloalkynyl groups, C2-C20 heterocycloalkyl groups, C2-C20 heterocycloalkenyl groups, C2-C20 heterocycloalkynyl groups, C3-C20 heteroaryl groups, (meth)acrylate groups, or combinations thereof.

[0048] Furthermore, unless otherwise specified herein, "hetero" means that the chemical formula contains at least one heteroatom from at least one of N, O, S, and P.

[0049] Furthermore, unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible. Unless otherwise defined herein, “combination” means mixing or copolymerization. “Copolymerization” means block copolymerization, alternating copolymerization or random copolymerization, and “copolymer” means block copolymer, alternating copolymer or random copolymer.

[0050] Unless otherwise specified herein, unsaturated bonds include not only carbon-carbon multiple bonds but also other molecular bonds such as carbonyl bonds and azo bonds.

[0051] Unless otherwise defined in the chemical formulas herein, the absence of a chemical bond at a position where one should be depicted means that a hydrogen atom is bonded to that position.

[0052] Unless otherwise defined herein, "*" means a portion linked to the same or different atoms or chemical formulas.

[0053] A photosensitive resin composition according to one embodiment includes a resin comprising a polymer represented by the following chemical formula 1.

[0054] [Chemical formula 1] [ka]

[0055] In the above chemical formula 1, R 1 and R 2 Each of these is independently a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group. L 1 These are single-bonded, substituted, or unsubstituted C1-C20 alkylene groups. L 2 It is a divalent linking group derived from acid anhydrides, L 3This is a divalent linking group containing an ester linking group (*-C(=O)O-* or *-OC(=O)-*), n is an integer between 1 and 50.

[0056] Many attempts have been made to polymerize various types of positive-type polyimide precursor resins in order to ensure low dielectric constant (Dk) and dielectric loss tangent (Df). However, it is now known that the lower the dielectric constant (Dk) and dielectric loss tangent (Df), the easier it is to ensure low dielectric constant (Dk) and dielectric loss tangent (Df) by increasing the content of fluoro atoms in the molecules constituting the resin and decreasing the content of imide structures.

[0057] However, as semiconductor technology advances and chip size decreases, the positive-type polyimide precursor resins currently in use do not cure well at low temperatures and have insufficient pattern-forming properties. Therefore, there is a demand to switch to negative-type polyimide precursor resins.

[0058] Therefore, the present inventors have invented a structure to ensure a low dielectric constant (Dk) and dielectric loss tangent (Df) for a negative-type polyimide precursor resin (or negative-type resin), unlike conventional positive-type polyimide precursor resins. Furthermore, they have confirmed that the dielectric constant and dielectric loss tangent of the negative-type polyimide precursor resin (or negative-type resin) can be kept low, for example, having a dielectric loss tangent (Df) of 0.001 to 0.015 at a frequency of 10 GHz, while simultaneously enabling easy negative pattern formation and improving reliability, thus completing the present invention.

[0059] The following provides a detailed explanation of each component.

[0060] (A) Resin Polyimide (PI) or polybenzoxazole (PBO) resins are used as core elements in photosensitive resin compositions utilized in semiconductor circuit protective films to ensure film properties such as elongation and glass transition temperature (Tg), which are crucial for reliability. These photosensitive resin compositions, when used with other photocrosslinkable monomers and photopolymerization initiators, ensure excellent protective film properties. However, achieving superior patterns requires no residue, excellent sensitivity, and storage stability of at least two weeks at room temperature. Furthermore, high frequencies are necessary to improve the processing speed of electronic devices, and materials with low dielectric constant (Dk) and dielectric loss tangent (Df) are required to prevent transmission speed loss.

[0061] The resin used in the photosensitive resin composition according to one embodiment may be a negative-type resin, for example, a polyimide precursor resin, i.e., a polyamic acid or polyamic ester resin, and the polyamic acid or polyamic ester resin may include, but is not limited to, polymers produced by the polymerization reaction of a diamine compound and a dianehydride compound.

[0062] The negative-type resin contains the polymer represented by the above chemical formula 1, and it was confirmed that this can lower the dielectric constant (Dk) and dielectric loss tangent (Df) of the negative-type photosensitive resin composition in the high-frequency range.

[0063] For example, in the above chemical formula 1, L 2 It may also be represented by the following chemical formula 2-1 or chemical formula 2-2.

[0064] [Chemical formula 2-1] [ka]

[0065] [Chemical formula 2-2] [ka]

[0066] In the above chemical formula 2-1, L 4 These are single bonds, ether linking groups (*-O-*), or substituted or unsubstituted C1-C20 alkylene groups.

[0067] For example, in the above chemical formula 2-1, L 4 This may be a single bond or a substituted or unsubstituted C1-C20 alkylene group.

[0068] For example, in the above chemical formula 2-1, L 4 This may be a C1-C20 alkylene group substituted or unsubstituted with a halogen group. For example, the halogen group may be a fluoro group.

[0069] For example, in the above chemical formula 1, L 3 This may be a divalent linking group containing two or more ester linking groups. In this case, achieving low dielectric loss tangent characteristics may be more advantageous compared to the case containing one ester linking group.

[0070] For example, in the above chemical formula 1, L 3 It may be represented by the following chemical formula 3, but is not necessarily limited to this.

[0071] [Chemical formula 3] [ka]

[0072] In the above chemical formula 3, L 5 This is an ether linking group (*-O-*) or a substituted or unsubstituted C1-C20 alkylene group. L 6 These are substituted or unsubstituted C1-C10 alkylene groups.

[0073] Even if a cured film (insulating film, resin film) is manufactured using a negative-type photosensitive resin composition with a low dielectric loss tangent, it may be difficult to apply to semiconductor devices if its physical properties, such as adhesion to metal layers and reliability like heat resistance, are poor. However, the photosensitive resin composition according to one embodiment contains a polymer having the structure represented by the above chemical formula 1 as an essential component, and therefore, despite being a negative-type composition, it can have a low dielectric loss tangent and excellent reliability.

[0074] For example, the polymer represented by chemical formula 1 above may be represented by any one of the following chemical formulas 1-1 to 1-4, but is not necessarily limited to these.

[0075] [Chemical formula 1-1] [ka]

[0076] [Chemical formula 1-2] [ka]

[0077] [Chemical formula 1-3] [ka]

[0078] [Chemical formula 1-4] [ka]

[0079] In the above chemical formulas 1-1 to 1-4, L is a substituted or unsubstituted C1-C10 alkylene group. n is an integer between 1 and 50.

[0080] On the other hand, the resin may further contain other polymers having a structure different from the polymer represented by the above chemical formula 1. In this case, the other polymer may be a polymer produced by a polymerization reaction between a diamine compound and a dianhydride compound. In this case, it is possible to improve the elongation while maintaining low dielectric loss tangent properties.

[0081] For example, polymers produced by the polymerization reaction of diamine compounds and dianhydride compounds may contain a functional group represented by the following chemical formula 6.

[0082] [Chemical formula 6] [ka] In the above chemical formula 6, R 9 is a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl group. L 9 These are single-bonded, substituted, or unsubstituted C1-C10 alkylene groups.

[0083] For example, the polymer represented by the above chemical formula 1, and the polymer produced by the polymerization reaction of the diamine compound and the dianhydride compound may be included in a weight ratio of 50:50 to 90:10. In this case, the increase in the dielectric loss tangent of the photosensitive resin composition can be suppressed while simultaneously achieving the greatest improvement in elongation.

[0084] For example, a diamine compound may be represented by the following chemical formula 4, but is not necessarily limited to this.

[0085] [Chemical formula 4] [ka]

[0086] In the above chemical formula 4, L 7 *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-NR 0 -*(R 0This is a substituted or unsubstituted C1-C10 alkyl group, or a combination thereof.

[0087] For example, a dianhydride compound may be represented by the following chemical formula 5, but is not necessarily limited to this.

[0088] [Chemical formula 5] [ka]

[0089] In the above chemical formula 5, L 8 These are single bonds, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, and *-NR 0 -*(R 0 These are substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C1-C20 alkylene groups, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C2-C20 heterocyclic linking groups, or combinations thereof.

[0090] For example, L 8 If *-C≡C-*, the heat resistance, adhesive strength, and reliability of the cured film (insulating film, resin film) can be further improved.

[0091] For example, the dianhydride compound may be pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, etc., but is not necessarily limited to these.

[0092] The weight-average molecular weight (M) of the polymer represented by the above chemical formula 1.w The concentration may be between 3,000 g / mol and 300,000 g / mol. In this case, sufficient physical properties are obtained, and it has excellent solubility in organic solvents, making it easy to handle.

[0093] (B) Photopolymerizable compound A photosensitive resin composition according to one embodiment may further contain a photopolymerizable compound. The photopolymerizable compound may be a single compound or a mixture of two different compounds.

[0094] The photopolymerizable compound may also be a compound containing at least two functional groups represented by the following chemical formula 6.

[0095] [Chemical formula 6] [ka] In the above chemical formula 6, R 9 is a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl group. L 9 These are single-bonded, substituted, or unsubstituted C1-C10 alkylene groups.

[0096] For example, a compound containing at least two functional groups represented by the above chemical formula 6 may contain two to six functional groups represented by the above chemical formula 4. In this case, sufficient polymerization can occur during exposure in the pattern formation process to form a pattern with excellent heat resistance, light resistance, and chemical resistance.

[0097] For example, a compound containing at least two functional groups represented by the above chemical formula 6 may be, but is not limited to, a compound represented by any one of the following chemical formulas 7 to 9.

[0098] [Chemical formula 7] [ka]

[0099] [Chemical formula 8] [ka]

[0100] [Chemical formula 9] [ka]

[0101] In the above chemical formulas 7 to 9, p, q, r, s, and t are each independent integers between 1 and 10.

[0102] If the photopolymerizable compound is a mixture of two different compounds, one of the two different compounds may be a monofunctional or polyfunctional ester compound of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0103] Monofunctional or polyfunctional ester compounds of (meth)acrylic acid having at least one ethylenically unsaturated double bond include, 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, penta It may be erythritol 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, ethylene glycol monomethyl ether(meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy(meth)acrylate, or a combination thereof.

[0104] Examples of commercially available monofunctional or polyfunctional ester compounds of (meth)acrylic acid having at least one ethylenically unsaturated double bond include the following: Examples of monofunctional esters of (meth)acrylic acid include Aronics® M-101, Aronics M-111, and Aronics M-114 from Toagosei Chemical Industry Co., Ltd., KAYARAD® TC-110S and KAYARAD TC-120S from Nippon Kayaku Co., Ltd., and V-158 and V-2311 from Osaka Organic Chemical Industry Co., Ltd. Examples of (meth)acrylic acid difunctional esters include Aronics M-210, Aronics M-240, and Aronics M-6200 (registered trademark) from Toagosei Chemical Industry Co., Ltd., KAYARAD HDDA, KAYARAD HX-220, and KAYARAD R-604 from Nippon Kayaku Co., Ltd., and V-260, V-312, and V-335HP from Osaka Organic Chemical Industry Co., Ltd. Examples of trifunctional esters of (meth)acrylic acid include Aronics M-309, Aronics M-400, Aronics M-405, Aronics M-450, Aronics M-7100, Aronics M-8030, and Aronics M-8060 from Toagosei Chemical Industry Co., Ltd., KAYARAD TMPTA, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, and KAYARAD DPCA-120 from Nippon Kayaku Co., Ltd., and V-295, V-300, V-360, V-GPT, V-3PA, and V-400 from Osaka Organic Chemical Industry Co., Ltd. Such products can be used individually or in combination of two or more.

[0105] Photopolymerizable compounds can also be treated with acid anhydrides before use to impart better developability.

[0106] The photopolymerizable compound may be included in an amount of 5 to 20 parts by weight, for example, 7 to 15 parts by weight, per 100 parts by weight of the resin. When the photopolymerizable compound is included within the above range, sufficient curing occurs, resulting in excellent reliability, excellent heat resistance, light resistance, and chemical resistance of the pattern, as well as excellent resolution and adhesion.

[0107] (C) Photopolymerization initiator A photosensitive resin composition according to one embodiment may further contain a photopolymerization initiator. The photopolymerization initiator can be an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, or an oxime compound, among others.

[0108] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-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.

[0109] Examples of benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylic benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0110] Examples of thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, and 2,4-diisopropylthioxanthone.

[0111] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0112] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl4,6-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, and 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine. Examples include 2-biphenyl4,6-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(trichloromethyl)-6-piperonyl-s-triazine, and 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine.

[0113] Examples of oxime compounds include O-acyl oxime compounds, 2-(O-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyl oxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropane-1-one. Specific examples of O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholine-4-ylphenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butan-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.

[0114] In addition to the compounds mentioned above, other photopolymerization initiators that can be used include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, non-imidazole compounds, or fluorene compounds.

[0115] 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, or for example, 1 to 7 parts by weight, per 100 parts by weight of resin. When the photopolymerization initiator is included within the above range, sufficient photopolymerization occurs, resulting in excellent sensitivity and improved transmittance.

[0116] (D) Solvent The solvent can be a substance that is compatible with but does not react with the resin, photopolymerizable monomer, and photopolymerization initiator.

[0117] Examples of solvents 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, methyl ethyl ketone, cyclohexanone, and 4-hydroxy-4-methyl Ketones such as 2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylate alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactate esters such as methyl lactate and ethyl lactate; alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate. Alkyl hydroxyacetates, alkyl 3-oxypropionates such as methyl 3-oxypropionate and ethyl 3-oxypropionate, alkyl 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate, alkyl 2-oxypropionates such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate, methyl 2-methoxypropionate,Alkyl 2-alkoxypropionate esters such as ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionate esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; monooxymonocarboxylate alkyl esters of alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyethyl acetate, and methyl 2-hydroxy-3-methylbutanoate. Examples include esters such as ethyl esters and ketonic acid esters such as ethyl pyruvate, as well as 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, 3-methylbenzoic acid, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

[0118] The solvent may be included in an amount of 100 to 500 parts by weight per 100 parts by weight of resin. When the solvent is within the above range, the photosensitive resin composition has an appropriate viscosity, resulting in excellent processability during the production of the photosensitive resin film.

[0119] (E) Other additives A photosensitive resin composition according to one embodiment may further contain other additives.

[0120] The photosensitive resin composition may contain additives such as diacides (e.g., malonic acid), alkanolamines (e.g., 3-amino-1,2-propanediol, N-phenyldiethanolamine), leveling agents, silane coupling agents, surfactants, epoxy compounds, thermal latent acid generators, developer modifiers, curing agents, sensitizers, radical scavengers, adhesives, organic acids, or combinations thereof, to prevent stains and spots during coating, improve leveling properties, or prevent the formation of residues due to undeveloped material. The amount of these additives used can be easily adjusted according to the desired physical properties.

[0121] For example, silane coupling agents may have reactive substituents such as vinyl groups, carboxyl groups, methacryloxy groups, isocyanate groups, or epoxy groups to improve adhesion to the substrate, and their structure differs from that of silane compounds.

[0122] Examples of silane coupling agents include trimethoxysilyl benzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatetopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, or β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, which can be used individually or in combination of two or more.

[0123] The silane coupling agent may be included in an amount of 0.01 to 10 parts by weight per 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included within the above range, the adhesion, storage properties, etc., are excellent.

[0124] For example, surfactants are added to prevent film thickness stains or to improve developability, and may include fluorinated surfactants and / or silicone-based surfactants.

[0125] As fluorine-based surfactants, those commercially available under names such as BM-1000 and BM-1100 from BM Chemie, Megafac® F142D, Megafac F172, Megafac F173, Megafac F183, and Megafac F554 from DIC Corporation, Florad FC-135, Florad FC-170C®, Florad FC-430, and Florad FC-431 from Sumitomo 3M Limited, Surflon® S-112, Surflon S-113, Surflon S-131, Surflon S-141, and Surflon S-145 from Asahi Glass Co., Ltd., and SH-28PA, SH-190, SH-193, SZ-6032, and SF-8428 from Toray Silicon Corporation can be used.

[0126] As for silicone-based surfactants, those commercially available from BYK Chem under names such as 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 can be used.

[0127] The surfactant can be used in an amount of 0.001 to 5 parts by weight per 100 parts by weight of the photosensitive resin composition. When the surfactant is within the above range, coating uniformity is ensured, stains do not occur, and excellent wetting properties are observed for ITO substrates or glass substrates, Si wafers, SiNx wafers, and Cu substrates.

[0128] Furthermore, the photosensitive resin composition may further contain epoxy compounds as additives to improve adhesion and other properties. Examples of epoxy compounds that can be used include epoxy novolac acrylic carboxylate resin, orthocresol novolac epoxy resin, phenol novolac epoxy resin, tetramethylbiphenyl epoxy resin, bisphenol A type epoxy resin, alicyclic epoxy resin, or combinations thereof.

[0129] The epoxy compound can be used in an amount of 0.01 to 5 parts by weight per 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within this range, the shelf life, adhesion, and other properties can be improved.

[0130] Furthermore, the photosensitive resin composition may further contain a thermal latent acid generator. Examples of thermal latent acid generators include, but are not limited to, aryl sulfonic acids such as p-toluenesulfonic acid and benzenesulfonic acid, perfluoroalkyl sulfonic acids such as trifluoromethanesulfonic acid and trifluorobutanesulfonic acid, alkyl sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, and butanesulfonic acid, or combinations thereof.

[0131] Furthermore, the photosensitive resin composition may further contain organic acids such as citric acid to improve its low dielectric loss tangent properties.

[0132] Furthermore, the photosensitive resin composition may also contain a certain amount of other additives, such as antioxidants and stabilizers, as long as they do not impair its physical properties.

[0133] Another embodiment provides a photosensitive resin film produced by exposing, developing, and curing the above-mentioned photosensitive resin composition.

[0134] The photosensitive resin film may be, for example, a semiconductor redistribution layer insulating film, but is not necessarily limited to this; any cured film applicable to electronic elements is acceptable.

[0135] The method for manufacturing a photosensitive resin film is as follows:

[0136] (1) Coating and film formation stage A photosensitive resin composition is applied to a substrate such as a glass substrate or ITO substrate, Si wafer, SiNx wafer, or Cu substrate that has undergone a predetermined pretreatment, to a desired thickness using methods such as spin or slit coating, roll coating, screen printing, or applicator coating. The coating is then formed by heating at 70°C to 150°C for 1 to 10 minutes to remove the solvent.

[0137] (2) Exposure step After a mask is placed over the resulting photosensitive resin film to form the necessary pattern, it is irradiated with active rays in the 200nm to 500nm range. Light sources that can be used for irradiation include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and argon gas lasers. In some cases, X-rays and electron beams can also be used.

[0138] The exposure dose varies depending on the type and amount of each component in the composition and the thickness of the dried film, but when using a high-pressure mercury lamp, it is 500 mJ / cm². 2 (Based on a 365nm sensor) The results are as follows:

[0139] (3) Development stage In the development method, following the exposure stage, an alkaline aqueous solution or organic solvent is used as a developer to dissolve and remove unnecessary parts, leaving only the exposed areas to form a pattern.

[0140] (4) Post-processing stage The image pattern obtained during the development stage is subject to a post-heating process to obtain a pattern with superior properties in terms of heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength, and storage stability. For example, after development, the image can be heated in an oven at 200°C to 400°C under a nitrogen atmosphere for more than one hour.

[0141] Another embodiment provides a semiconductor device including a photosensitive resin film.

[0142] The electronic element may be, for example, a semiconductor element, but is not necessarily limited to this.

[0143] Preferred embodiments of the present invention are described below. However, the following embodiments are merely preferred embodiments of the present invention, and the present invention is not limited to the following embodiments. [Examples]

[0144] <Synthesis of resins> (Comparative Synthesis Example 1) 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 four times the amount of pyromellitic dianhydride in N-methyl-2-pyrrolidone, and the mixture was stirred at room temperature for 48 hours to obtain ester solution 1.

[0145] Furthermore, 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 four times the amount of N-methyl-2-pyrrolidone as 4,4'-oxydiphthalic anhydride (ODPA), and the mixture was stirred at room temperature for 48 hours to obtain ester solution 2. After mixing ester solution 1 and ester solution 2, 2.2 equivalents of thionyl chloride were added dropwise to the total volume of the BPDA-HEMA ester solution and ODPA-HEMA ester solution while cooling in an ice bath, and the mixture was stirred for 1 hour to prepare an acid chloride solution.

[0146] A solution was prepared by dissolving 4,4'-oxydianiline (ODA) (100 mmol) and twice the equivalent amount of pyridine thionyl chloride in four times the amount of N-methyl-2-pyrrolidone compared to ODA. This solution was then added dropwise to the previously prepared acid chloride solution while cooling in an ice bath. After the addition was complete, the reaction mixture was added dropwise to distilled water, and the resulting precipitate was collected by filtration, washed twice with distilled water, and then vacuum-dried to obtain the polyamic acid ester. The weight-average molecular weight of the obtained polymer (polyamic acid ester) was 25,000 g / mol.

[0147] (Synthesis Example 1) In a four-necked flask equipped with a stirrer, temperature control device, nitrogen gas injection device, and condenser, 600 g of γ-butyrolactone (GBL) was mixed with 0.58 mol of 4,4'-oxydiphthalic anhydride (ODPA) monomer while passing nitrogen through, and 1.22 mol of 2-hydroxyethyl methacrylate (HEMA) was added. While stirring at room temperature, 1.16 mol of pyridine was added to obtain the reaction mixture. After reacting at room temperature for 16 hours, the mixture was cooled to -10°C and a solution of 1.17 mol of dicyclohexylcarbodiimide (DCC) dissolved in 250 g of GBL was added dropwise over 30 minutes. After stirring for an additional 5 minutes, a solution of 0.54 mol of diamine monomer represented by chemical formula B below and 300 g of GBL was added for 40 minutes and stirred for an additional 2 hours. After reacting at room temperature for 1 hour, 30 g of monomer represented by chemical formula C below was added and stirred for 1 hour.

[0148] (Chemical formula B) [ka]

[0149] (Chemical formula C) [ka]

[0150] Next, GBL was added to the reaction solution to obtain a solid content of 18%, and the solution was added to 3 liters of ethanol to obtain a precipitate. The polymer was filtered and separated, dissolved in 1.5 liters of tetrahydrofuran (THF), and added dropwise to 30 liters of water to produce a precipitate, which was then filtered and vacuum-dried. By drying under reduced pressure at 50°C for more than 24 hours, the polymer represented by the following chemical formula 1-1 (where L is an unsubstituted ethylene group) (weight-average molecular weight: 22,000 g / mol) was produced.

[0151] [Chemical formula 1-1] [ka]

[0152] (Synthesis Example 2) In Synthesis Example 1, instead of the 4,4'-oxydiphthalic anhydride (ODPA) monomer, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) was used to obtain a polymer represented by the following chemical formulas 1-2 (where L is an unsubstituted ethylene group) (weight-average molecular weight: 22,000 g / mol).

[0153] [Chemical formula 1-2] [ka]

[0154] (Synthesis Example 3) In Synthesis Example 1, instead of the 4,4'-oxydiphthalic anhydride (ODPA) monomer, 3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA) was used to obtain a polymer represented by the following chemical formulas 1-3 (where L is an unsubstituted ethylene group) (weight-average molecular weight: 22,000 g / mol).

[0155] [Chemical formula 1-3] [ka]

[0156] (Synthesis Example 4) By substituting pyromellitic dianhydride for the 4,4'-oxydiphthalic anhydride (ODPA) monomer in Synthesis Example 1, a polymer represented by the following chemical formulas 1-4 (where L is an unsubstituted ethylene group) (weight-average molecular weight: 22,000 g / mol) was obtained.

[0157] [Chemical formula 1-4] [ka]

[0158] <Manufacturing of photosensitive resin composition> (Comparative Example 1) 33.28 g of the polymer produced in Comparative Synthesis Example 1 was mixed with 3.69 g of tetraethylene glycol dimethacrylate. To this mixture, 1.66 g of photopolymerization initiator (PBG305, TRONLY), 3.32 g of sensitizer (N-Phenyldiethanolamine), 0.55 g of radical scavenger (CX-1790), 0.92 g of adhesion enhancer (A-187), 0.18 g of citric acid, 50.76 g of GBL, and 5.64 g of DMSO were added and the mixture was thoroughly stirred. The mixture was then filtered through a 0.45 μm polypropylene resin filter to obtain a negative-type photosensitive resin composition.

[0159] (Example 1) The procedure was the same as in Comparative Example 1, except that a mixture of 16.64 g of the polymer produced in Comparative Synthesis Example 1 and 16.64 g of the polymer produced in Synthesis Example 1 (in a 50:50 weight ratio) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0160] (Example 2) The procedure was the same as in Comparative Example 1, except that a mixture of 3.328 g of the polymer produced in Comparative Synthesis Example 1 and 29.952 g of the polymer produced in Synthesis Example 1 (in a weight ratio of 10:90) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0161] (Example 3) The procedure was the same as in Comparative Example 1, except that the polymer produced in Synthesis Example 1 was used instead of the polymer produced in Comparative Synthesis Example 1.

[0162] (Example 4) The procedure was the same as in Comparative Example 1, except that a mixture of 16.64 g of the polymer produced in Comparative Synthesis Example 1 and 16.64 g of the polymer produced in Synthesis Example 2 (in a 50:50 weight ratio) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0163] (Example 5) The procedure was the same as in Comparative Example 1, except that a mixture of 16.64 g of the polymer produced in Comparative Synthesis Example 1 and 16.64 g of the polymer produced in Synthesis Example 3 (in a 50:50 weight ratio) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0164] (Example 6) The procedure was the same as in Comparative Example 1, except that a mixture of 16.64 g of the polymer produced in Comparative Synthesis Example 1 and 16.64 g of the polymer produced in Synthesis Example 4 (in a 50:50 weight ratio) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0165] (Example 7) The procedure was the same as in Comparative Example 1, except that a mixture of 1.664 g of the polymer produced in Comparative Synthesis Example 1 and 31.616 g of the polymer produced in Synthesis Example 1 (in a weight ratio of 5:95) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0166] (Example 8) The procedure was the same as in Comparative Example 1, except that a mixture of 18.304 g of the polymer produced in Comparative Synthesis Example 1 and 14.976 g of the polymer produced in Synthesis Example 1 (in a weight ratio of 55:45) was used instead of 33.28 g of the polymer produced in Comparative Synthesis Example 1.

[0167] <Rating> A photosensitive resin composition was spin-coated onto an 8-inch silicon wafer and pre-baked at approximately 100°C for 4 minutes to obtain a coating with a thickness of approximately 10.0 μm. After cooling at room temperature for 60 seconds, the wafer was irradiated with light for 700 msec using an i-line stepper (Nikon, NSR-2005i10C) to induce the photocuring reaction of the photosensitive portion. The exposed substrate was developed twice at room temperature with 100% cyclopentanone solvent using a paddle method for 60 seconds, and then washed with 100% PGMEA solvent for 60 seconds. The developed wafer was then cured in a 220°C oven under a nitrogen atmosphere for 2 hours to obtain a photosensitive resin film.

[0168] (1) Evaluation of dielectric loss tangent: The dielectric loss tangent (Df) was determined by pre-treating the manufactured film by drying it at 130°C for 30 minutes, followed by aging it for 24 hours in a constant temperature and humidity chamber maintained at 23°C and 50% relative humidity. Subsequently, the dielectric properties were measured at a frequency of 10 GHz using the SPDR (Split Post Dielectric Resonator) measurement method with Keysight's ENA, and the results are shown in Table 1 below.

[0169] (2) Evaluation of elongation: After the cured film was precipitated in a 1% HF solution for 1 hour and the PID coating process was performed, the test specimens were cut into 1cm x 10cm pieces and the elongation at room temperature (25°C) was measured using a Shimadzu tensile tester (HZ-1003), and the results are shown in Table 1 below.

[0170] (3) Reliability evaluation: The cured film was subjected to a thermal cycle (-55°C to 125°C) under reliability conditions for 2000 cycles. After that, the presence or absence of crack formation between the film and Cu was checked using FE-SEM, and the results are shown in Table 1 below.

[0171] [Table 1]

[0172] Table 1 shows that the photosensitive resin composition according to one embodiment exhibits excellent elongation characteristics and reliability despite having a low dielectric loss tangent.

[0173] The present invention is not limited to the embodiments described above and can be manufactured in a variety of different forms. Those with ordinary skill in the art to which the invention pertains should understand that the invention can be implemented in other specific forms without altering the technical idea or essential features of the invention. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not limiting.

Claims

1. Contains resin, The aforementioned resin is a photosensitive resin composition comprising a polymer represented by the following chemical formula 1. [Chemical formula 1] 【Chemistry 1】 (In the above chemical formula 1, R １ and R ２ Each of these is independently a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group. L １ These are single-bonded, substituted, or unsubstituted C1-C20 alkylene groups, L ２ It is a divalent linking group derived from acid anhydrides, L ３ This is a divalent linking group containing an ester linking group (*-C(=O)O-* or *-OC(=O)-*), n is an integer between 1 and 50.

2. Said L ２ The photosensitive resin composition according to claim 1, which is represented by the following chemical formula 2-1 or chemical formula 2-2. [Chemical formula 2-1] 【Chemistry 2】 [Chemical formula 2-2] 【Transformation 3】 (In the above chemical formula 2-1, L ４ (This refers to a single bond, an ether linking group (*-O-*), or a substituted or unsubstituted C1-C20 alkylene group.)

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

4. The above-mentioned L ３ is the photosensitive resin composition according to claim 1, represented by the following chemical formula 3. [Chemical formula 3] 【Chemistry 4】 (In the above chemical formula 3, L ５ This is an ether linking group (*-O-*) or a substituted or unsubstituted C1-C20 alkylene group. L ６ (These are substituted or unsubstituted C1-C10 alkylene groups.)

5. The photosensitive resin composition according to claim 1, wherein the polymer represented by chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4. [Chemical formula 1-1] 【Transformation 5】 [Chemical formula 1-2] 【Transformation 6】 [Chemical formula 1-3] 【Transformation 7】 [Chemical formula 1-4] 【Transformation 8】 (In the above chemical formulas 1-1 to 1-4, L is a substituted or unsubstituted C1-C10 alkylene group. n is an integer between 1 and 50.

6. The resin further comprises a polymer produced by a polymerization reaction of a diamine compound and a dianhydride compound. The photosensitive resin composition according to claim 1, wherein 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 the following chemical formula 4. [Chemical formula 4] 【Chemistry 9】 (In the above chemical formula 4, L ７ *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-NR ０ - * (R ０ (These are substituted or unsubstituted C1-C10 alkyl groups) or combinations thereof.

8. The photosensitive resin composition according to claim 6, wherein the dianhydride compound is represented by the following chemical formula 5. [Chemical formula 5] 【Chemistry 10】 (In the above chemical formula 5, L ８ These are single bonds, *-O-*, *-S-*, *-C≡C-*, *-C(=O)-*, *-C(=O)O-*, and *-NR ０ - * (R ０ These are substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C1-C20 alkylene groups, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C2-C20 heterocyclic linking groups, or combinations thereof.

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 contained 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 contains a functional group represented by the following chemical formula 6. [Chemical formula 6] 【Chemistry 11】 (In the above chemical formula 6, R ９ is a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl group, L ９ (These are single-bonded, substituted, or unsubstituted C1-C10 alkylene groups.)

11. The photosensitive resin composition according to claim 1, further comprising a photopolymerizable compound, a photopolymerization initiator, and a solvent.

12. The aforementioned photosensitive resin composition is With respect to 100 parts by weight of the aforementioned resin The photopolymerizable compound is contained in an amount of 5 to 20 parts by weight, The photopolymerization initiator is contained in an amount of 0.1 to 20 parts by weight. The photosensitive resin composition according to claim 11, wherein the solvent is contained in an amount of 100 to 500 parts by weight.

13. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition is a negative-type photosensitive resin composition.

14. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition has a dielectric loss tangent (Df) of 0.001 to 0.015 at a frequency of 10 GHz.

15. A photosensitive resin film manufactured using the photosensitive resin composition described in any one of claims 1 to 14.

16. A semiconductor element comprising a photosensitive resin film as described in claim 15.

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