Semiconductor photoresist composition and method of forming pattern using same

Abstract

A semiconductor photoresist composition and a method of forming a pattern using the same are provided. The semiconductor photoresist composition includes: an organometallic compound; a polymer including a first structural unit represented by Chemical Formula M-1 and a second structural unit represented by Chemical Formula 2 or Chemical Formula 3; and a solvent. The chemical formula M-1, the chemical formula 2 and the chemical formula 3 are described in the specification. The present application can realize a pattern having improved sensitivity and line edge roughness characteristics.

Description

[0001] Cross-reference of related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0156548, filed on November 6, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to a semiconductor photoresist composition and a method of forming patterns using the same. Background Technology

[0004] Extreme ultraviolet (EUV) lithography has attracted considerable attention as an essential technology for manufacturing next-generation semiconductor devices, such as semiconductor chips. EUV lithography is a patterning technique that uses EUV rays with a wavelength of 13.5 nanometers as the exposure source. It is known to form extremely fine patterns (e.g., less than or equal to 20 nanometers) during the exposure process for manufacturing semiconductor devices, such as semiconductor chips.

[0005] The realization of EUV lithography relies on the development of compatible photoresists capable of achieving spatial resolutions of 16 nanometers or less. Currently, efforts are underway to address shortcomings in specifications such as resolution, photospeed, and feature roughness (also known as line-edge roughness or LER) of chemically amplified (CA) photoresists used in next-generation devices.

[0006] The inherent image blurring caused by acid-catalyzed reactions in these polymer types of photoresists limits resolution at small feature sizes, a long-standing challenge in electron beam lithography. Chemically amplified (CA) photoresists are designed for high sensitivity, but their typical elemental composition reduces absorbance at 13.5 nm wavelength, thus decreasing sensitivity. Therefore, CA photoresists may face further challenges during EUV exposure.

[0007] Furthermore, CA photoresists can present difficulties at small feature sizes due to roughness issues. Experimentally, partly due to the nature of the acid catalyst process, the line edge roughness (LER) of CA photoresists increases as the photosensitivity decreases. Therefore, the semiconductor industry desires or needs novel high-performance photoresists to address these defects and problems inherent in CA photoresists.

[0008] To overcome the aforementioned drawbacks of chemically amplified (CA) organic photosensitive compositions, inorganic photosensitive compositions have been investigated. These inorganic compositions are primarily or mainly used for negative tone patterning and exhibit resistance to removal by developer compositions due to chemical modification via a non-chemical amplification mechanism. The inorganic compositions contain inorganic elements with higher EUV absorbance than hydrocarbons, thus ensuring sensitivity through a non-chemical amplification mechanism. Furthermore, these inorganic compositions are less sensitive to stochastic effects and are known to have low line edge roughness and fewer defects.

[0009] Inorganic photoresists based on tungsten peroxy polyacids mixed with tungsten, niobium, titanium and / or tantalum have been reported as radiation-sensitive materials for patterning.

[0010] These materials are effective for patterning large pitch bilayer configurations, similar to far ultraviolet (deep UV), X-ray, and electron beam sources. When the cationic metal oxide hafnium sulfate (HfSO₄) is used... x Improved performance was observed when the material, together with a peroxide complexing agent, was used for imaging 15 nm half-pitch (HP) chromatic atomization via projection EUV exposure. This system exhibited high performance comparable to non-CA photoresists and achieved practical photosensitivity close to that required for EUV photoresists. However, hafnium sulfate metal oxide materials with peroxide complexing agents have some practical drawbacks. First, these materials are coated with a mixture of corrosive sulfuric acid / hydrogen peroxide and exhibit insufficient stability over their shelf life. Second, as a composite mixture, modifying the structure to achieve performance improvements is challenging. Third, development must be carried out in a solution of tetramethylammonium hydroxide (TMAH) at extremely high concentrations (e.g., 25 wt% or higher).

[0011] To address these issues, research has focused on developing tin-containing molecules with excellent or suitable absorption for extreme ultraviolet light. For organotin polymers among these tin-containing molecules (e.g., tin-containing molecules), alkyl ligands are dissociated through light absorption or the resulting secondary electrons. The dissociated alkyl ligands then crosslink with adjacent chains via oxo bonds, enabling negative patterning that cannot be removed by organic developers. Although such organotin polymers exhibit significantly improved sensitivity while maintaining the desired resolution and line edge roughness (LER), further improvements to the patterning properties are needed or desired for commercial viability. Summary of the Invention

[0012] One or more aspects of embodiments of this disclosure relate to a semiconductor photoresist composition having enhanced (e.g., improved or suitable) sensitivity and line edge roughness (LER) characteristics.

[0013] One or more aspects of embodiments of this disclosure relate to a method of forming patterns using the semiconductor photoresist composition.

[0014] Additional aspects will be set forth in part in the following description, and will become apparent in part from reading the description, or may be learned by practicing the embodiments presented in this disclosure.

[0015] The semiconductor photoresist composition according to one or more embodiments comprises: an organometallic compound; a polymer including a first structural unit that may be represented by chemical formula M-1 and a second structural unit that may be represented by chemical formula 2 or chemical formula 3; and a solvent.

[0016] [Chemical Formula M-1]

[0017]

[0018] [Chemical Formula 2] [Chemical Formula 3]

[0019]

[0020] In chemical formulas M-1, 2, and 3

[0021] R 1 To R 3 Each can be independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group.

[0022] L 1 and L 2 Each can be a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a combination thereof.

[0023] X 1 It can be a single bond, -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O-, -C(=O)O-, -OC(=O), -OC(=O)O-, -NR a - (where R) a (which may be hydrogen, deuterium, or substituted or unsubstituted C1 to C10 alkyl groups), or combinations thereof.

[0024] X 2 It can be a single bond, -C(=O)-, or a substituted or unsubstituted C1 to C10 alkylene group.

[0025] X 3Can be a single key, -L 4 -O- (where L) 4 (or unsubstituted C1 to C10 alkylene groups), or substituted or unsubstituted C1 to C10 alkylene groups.

[0026] R 4 It may be hydrogen, fluorine, hydroxyl, substituted or unsubstituted C1 to C20 alkyl groups, or combinations thereof.

[0027] Selected from R 4 L 1 and L 2 At least one of them includes fluorine and hydroxyl,

[0028] R 5 It is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0029] R 6 To R 8 Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0030] m1 and m2 can each be an integer from 1 to 4 independently, and

[0031] This is the connection point.

[0032] According to one or more embodiments of the present disclosure, a method of forming a pattern includes: forming an etch target layer on a substrate; coating a semiconductor photoresist composition on the etch target layer to form a photoresist film; patterning the photoresist film to form a photoresist pattern; and using the photoresist pattern as an etch mask to etch the etch target layer.

[0033] Patterns formed using semiconductor photoresist compositions according to one or more embodiments can exhibit excellent or suitable sensitivity and line edge roughness (LER) characteristics. For example, the semiconductor photoresist compositions described herein overcome the limitations of chemically amplified (CA) photoresists by utilizing organometallic compounds that enhance EUV absorption and reduce line edge roughness. This composition, combined with the patterning method, provides a solution for achieving high-resolution and high-sensitivity patterning in semiconductor manufacturing. Attached Figure Description

[0034] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the disclosure. The above and other aspects, features, and advantages of certain embodiments of the present disclosure will become more apparent from the following description, taken in conjunction with the accompanying drawings, in which:

[0035] Figures 1A to 1E It is a cross-sectional view used to illustrate a method of forming a pattern using a semiconductor photoresist composition according to one or more embodiments of the present disclosure.

[0036] [Icon Symbol Explanation]

[0037] 100: Substrate / Semiconductor Substrate

[0038] 102: Film

[0039] 104: Resist underlayer

[0040] 106: Photoresist film

[0041] 106a: Unexposed area

[0042] 106b: Exposure Zone

[0043] 108: Photoresist pattern

[0044] 110: Patterned mask

[0045] 112: Organic membrane pattern

[0046] 114: Thin Film Pattern Detailed Implementation

[0047] This disclosure may be modified in many alternative forms, and therefore specific embodiments will be illustrated and described in more detail with reference to the accompanying drawings. However, it should be understood that this is not intended to limit this disclosure to the specific forms disclosed, but rather to cover all modifications, equivalents, and alternatives that fall within the spirit and scope of this disclosure.

[0048] In the following description, one or more embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. In order to keep the present disclosure brief, established functions or structures will not be repeated.

[0049] To clearly illustrate this disclosure, certain non-essential descriptions and relationships have not been provided, and throughout this disclosure, identical or similar configuration elements are indicated by the same reference numerals. Furthermore, since the size and thickness of each configuration shown in the drawings are illustrated for better understanding and ease of explanation, this disclosure is not necessarily limited thereto.

[0050] In the accompanying drawings, the thickness of layers, films, panels, regions, etc., is exaggerated for clarity. In the accompanying drawings, the thickness of a portion of a layer or region is exaggerated for ease of explanation. It will be understood that when an element (e.g., a layer, film, region, or substrate) is referred to as being "on" another element (e.g., when an element (e.g., a layer, film, region, or substrate) is referred to as being "on" another element), the element may be directly on the other element, or there may be intermediate elements present.

[0051] In this document, "substituted" refers to hydrogen atoms being replaced by: deuterium, halogen, hydroxyl, carboxyl, thiol, cyano, nitro, -NRR' (wherein R and R' can each be independently hydrogen, a substituted or unsubstituted C1 to C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group), -SiRR'R'' (wherein R, R', and R' Each of these groups can be hydrogen, a substituted or unsubstituted C1 to C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, C1 to C30 alkyl, C1 to C10 haloalkyl, C1 to C10 alkylsilyl, C3 to C30 cycloalkyl, C6 to C30 aryl, C1 to C20 alkoxy, C1 to C20 sulfide, or a combination thereof. "Unsubstituted" means that the hydrogen atom has not been replaced by another substituent and remains unchanged as a hydrogen atom.

[0052] Unless otherwise defined (e.g., when no other definition is provided), “alkyl” as used herein refers to a straight-chain or branched aliphatic hydrocarbon group. Alkyl groups may be “saturated alkyl groups” without any double or triple bonds.

[0053] The alkyl group can be C1 to C8 alkyl. For example, the alkyl group can be C1 to C7 alkyl, C1 to C6 alkyl, or C1 to C5 alkyl. For example, C1 to C5 alkyl can be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or 2,2-dimethylpropyl.

[0054] Unless otherwise defined (e.g., when no other definition is provided), “cycloalkyl” as used herein refers to a monovalent cyclic aliphatic hydrocarbon group.

[0055] The cycloalkyl group can be C3 to C8 cycloalkyl, such as C3 to C7 cycloalkyl, C3 to C6 cycloalkyl, C3 to C5 cycloalkyl, or C3 to C4 cycloalkyl. For example, the cycloalkyl group can be cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, but this disclosure is not limited thereto.

[0056] As used in this article, “aryl” refers to a substituent in which all atoms in the cyclic substituent have p orbitals and these p orbitals are conjugated, and may include monocyclic or fused-ring polycyclic functional groups (i.e., rings that share adjacent carbon atom pairs).

[0057] As used herein, "heteroaryl" can refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly linked by σ bonds, or if the heteroaryl group comprises two or more rings (e.g., when the heteroaryl group comprises two or more rings), the two or more rings may be fused. If the heteroaryl group is a fused ring (e.g., when the heteroaryl group is a fused ring), each ring may comprise one to three heteroatoms.

[0058] Unless otherwise defined, “alkenyl” as used herein refers to an aliphatic unsaturated alkenyl group comprising at least one double bond, which is a straight-chain or branched aliphatic hydrocarbon group.

[0059] Unless otherwise defined, “alkynyl” as used herein refers to an aliphatic unsaturated alkynyl group comprising at least one triple bond, which is a straight-chain or branched aliphatic hydrocarbon group.

[0060] In some embodiments, unless otherwise defined (e.g., when no other definition is provided), “hybrid” as used herein refers to 1 to 10 heteroatoms independently selected from N, O, S, and P.

[0061] Unless otherwise stated in this specification, the weight-average molecular weight was measured by dissolving the powder sample in tetrahydrofuran (THF) and then using an Agilent Technologies 1200 series gel permeation chromatography (GPC) column of LF-804 from Showa Denko Scientific Co., Ltd., and polystyrene from Showa Denko Scientific Co., Ltd. as the standard sample.

[0062] Unless otherwise defined (e.g., when no other definition is provided), the “…” described herein "" indicates the connection point of a structural unit or part of a compound.

[0063] Below, semiconductor photoresist compositions according to one or more embodiments are described.

[0064] The semiconductor photoresist composition according to one or more embodiments comprises: an organometallic compound; a polymer including a first structural unit represented by chemical formula M-1 and a second structural unit represented by chemical formula 2 or chemical formula 3; and a solvent.

[0065] [Chemical Formula M-1]

[0066]

[0067] [Chemical Formula 2] [Chemical Formula 3]

[0068]

[0069] In chemical formulas M-1, 2, and 3

[0070] R 1 To R 3 Each can be independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group.

[0071] L 1 and L 2 Each can be a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a combination thereof.

[0072] X 1 It can be a single bond, -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O-, -C(=O)O-, -OC(=O), -OC(=O)O-, -NR a - (where R) a (which may be hydrogen, deuterium, or substituted or unsubstituted C1 to C10 alkyl groups), or combinations thereof.

[0073] X 2 It can be a single bond, -C(=O)-, or a substituted or unsubstituted C1 to C10 alkylene group.

[0074] X 3 Can be a single key, -L 4 -O- (where L) 4 (or unsubstituted C1 to C10 alkylene groups), or substituted or unsubstituted C1 to C10 alkylene groups.

[0075] R 4 It may be hydrogen, fluorine, hydroxyl, substituted or unsubstituted C1 to C20 alkyl groups, or combinations thereof.

[0076] Selected from R 4 L 1 and L 2 At least one of them may include fluorine and hydroxyl,

[0077] R 5 It may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0078] R 6To R 8 Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0079] m1 and m2 can each be an integer from 1 to 4 independently, and

[0080] This is the connection point.

[0081] In chemical formulas 2 and 3, X 2 or X 3 A single key means that it is connected to X. 2 or X 3 The oxygen is directly attached to the terminal substituent (R). 5 Or R 7 ).

[0082] The first structural unit can exhibit excellent or suitable solubility in a solvent by including both fluorine and hydroxyl (e.g., including both fluorine and hydroxyl), thus enabling substantially uniform coating on the pattern, and the second structural unit can improve sensitivity by increasing extreme ultraviolet (EUV) absorption.

[0083] Therefore, patterns with improved sensitivity and line edge roughness (LER) characteristics can be achieved.

[0084] For example, the first structural unit can be represented by chemical formula 1.

[0085] [Chemical Formula 1]

[0086]

[0087] In chemical formula 1,

[0088] R 1 It can be hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group.

[0089] R c R d R e R f and R 4 Each of these can be independently hydrogen, fluorine, hydroxyl, substituted or unsubstituted C1 to C20 alkyl groups, or combinations thereof.

[0090] m3 and m4 can each be an integer from 1 to 10 independently.

[0091] X 1It can be a single bond, -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O-, -C(=O)O-, -OC(=O), -OC(=O)O-, -NR a - (where R) a It is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof, and

[0092] Selected from R c R d R e R f and R 4 At least one of them includes fluorine and hydroxyl.

[0093] In chemical formula 1, if m3 is 2 or greater than 2 (e.g., when m3 is 2 or greater than 2), each R c They may be the same as or different from each other.

[0094] In chemical formula 1, if m3 is 2 or greater than 2 (e.g., when m3 is 2 or greater than 2), each R d They may be the same as or different from each other.

[0095] In chemical formula 1, if m4 is 2 or greater than 2 (e.g., when m4 is 2 or greater than 2), each R e They may be the same as or different from each other.

[0096] In chemical formula 1, if m4 is 2 or greater than 2 (e.g., when m4 is 2 or greater than 2), each R f They may be the same as or different from each other.

[0097] In chemical formula 1, it is selected from R c R d R e R f and R 4 The meaning of "at least one of" including fluorine and hydroxyl groups can include the following:

[0098] Selected from R c R d R e R f and R 4 At least one of them includes fluorine and hydroxyl (e.g., a fluorine atom and a hydroxyl group), or

[0099] Selected from R c R d R e R f and R 4 At least one of them includes a C1 to C10 alkyl group substituted with one or more fluorine groups, and a C1 to C10 alkyl group substituted with one or more hydroxyl groups, or

[0100] Selected from R c R d R e R f and R 4 At least one of them includes one or more hydroxyl groups and one or more fluorinated C1 to C10 alkyl groups, or

[0101] Selected from R c R d R e R f and R 4 At least one of them includes a C1 to C5 alkyl group substituted with one or more hydroxyl groups, and one or more C1 to C5 fluoroalkyl groups, or

[0102] Selected from R c R d R e R f and R 4 At least one of the groups is fluorine, and at least one of the other groups (i.e., the remaining groups) is hydroxyl, or

[0103] Selected from R c R d R e R f and R 4 At least one of the groups is fluorine, and at least one of the other groups is or includes a C1 to C10 alkyl group substituted with one or more hydroxyl groups, or

[0104] Selected from R c R d R e R f and R 4 At least one of the groups is a hydroxyl group, and at least one of the other groups is or includes a C1 to C10 alkyl group substituted with one or more fluorine groups, or

[0105] Selected from R c R d R e R f and R 4 At least one of the groups is a C1 to C20 alkyl group substituted with one or more fluorine groups, and at least one of the other groups is a C1 to C20 alkyl group substituted with one or more hydroxyl groups.

[0106] For example, R 1 It can be hydrogen or methyl.

[0107] X 1 Can be a single bond, -O- or -NR a - (where R)a (It is hydrogen, deuterium, or substituted or unsubstituted C1 to C10 alkyl groups).

[0108] R 4 It may be fluorine, hydroxyl, a C1 to C10 alkyl group substituted with at least one fluorine, or a C1 to C10 alkyl group substituted with at least one hydroxyl.

[0109] For example, in chemical formula 1, the ingredients selected from R e R f and R 4 At least one of them may include fluorine and hydroxyl (e.g., including fluorine atoms and hydroxyl groups).

[0110] For example, in chemical formula 1, the ingredients selected from R e and R f At least one of them may be fluorine or a C1 to C10 alkyl group substituted with at least one fluorine, and R 4 It may be a hydroxyl group or a C1 to C10 alkyl group substituted with at least one hydroxyl group.

[0111] For example, in chemical formula 1, the ingredients selected from R e and R f At least one of them may be a hydroxyl group or a C1 to C10 alkyl group substituted with at least one hydroxyl group, and R 4 It may be fluorine or a C1 to C10 alkyl group substituted with at least one fluorine.

[0112] For example, in chemical formula 1, R e It may be a hydroxyl group or a C1 to C10 alkyl group substituted with at least one hydroxyl group, R f It may be fluorine or a C1 to C10 alkyl group substituted with at least one fluorine, and R 4 It may be a hydroxyl group, fluorine, or a C1 to C10 alkyl group substituted with at least one of fluorine and hydroxyl groups.

[0113] For example, in chemical formula 1, the ingredients selected from R e and R f At least one of them may be fluorine or a C1 to C10 alkyl group substituted with at least one fluorine, R 4 It may be a hydroxyl group or a C1 to C5 alkyl group substituted with at least one of hydroxyl and C1 to C5 fluoroalkyl groups.

[0114] For example, the first structural unit may be selected from groups in group I.

[0115] [Group I]

[0116]

[0117] In group I,

[0118] R1 Each can be independently hydrogen or methyl, and This is the connection point.

[0119] In chemical formula 2, if m1 is 2 or greater than 2 (e.g., when m1 is 2 or greater than 2), each OX 2 -R 5 They may be the same as or different from each other.

[0120] In chemical formula 2, if 5-m1 is 2 or greater than 2 (e.g., when 5-m1 is 2 or greater than 2), each R 6 They may be the same as or different from each other.

[0121] For example, chemical formula 2 can be represented by chemical formula 2-1 or chemical formula 2-2.

[0122] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0123]

[0124] In chemical formulas 2-1 and 2-2,

[0125] R 2 R 5 R 6 and m1 are as defined in this paper, and

[0126] This is the connection point.

[0127] For example, chemical formula 2-1 can be represented by (for example, selected from) any of chemical formula 2-1-(i) to chemical formula 2-1-(iv).

[0128] [Chemical Formula 2-1-(i)] [Chemical Formula 2-1-(ii)]

[0129]

[0130] [Chemical Formula 2-1-(iii)] [Chemical Formula 2-1-(iv)]

[0131]

[0132] In chemical formulas 2-1-(i) to 2-1-(iv),

[0133] R 2 It can be hydrogen or methyl.

[0134] R 5 R 5a and R 5bEach of these can be independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof.

[0135] R 6a R 6b R 6c and R 6d Each of them may be hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0136] For example, chemical formula 2-2 can be represented by any of chemical formulas 2-2-(i) to 2-2-(iii).

[0137] [Chemical Formula 2-2-(i)] [Chemical Formula 2-2-(ii)] [Chemical Formula 2-2-(iii)]

[0138]

[0139] In chemical formulas 2-2-(i) to 2-2-(iii),

[0140] R 2 It can be hydrogen or methyl.

[0141] R 5 It may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and

[0142] R 6a R 6b R 6c and R 6d Each of them may be hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0143] In chemical formula 3, if m2 is 2 or greater than 2 (e.g., when m2 is 2 or greater than 2), each C(=O)-OX 3 -R 7 They may be the same as or different from each other.

[0144] In chemical formula 3, if 5-m2 is 2 or greater than 2 (e.g., when 5-m2 is 2 or greater than 2), each R 8 They may be the same as or different from each other.

[0145] For example, chemical formula 3 can be represented by chemical formula 3-1 or chemical formula 3-2.

[0146] [Chemical Formula 3-1] [Chemical Formula 3-2]

[0147]

[0148] In chemical formulas 3-1 and 3-2,

[0149] R 3 R 7 R 8 L 4 m2 is as defined in this paper.

[0150] R 17 and R 18 Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0151] m5 is an integer between 0 and 10, and

[0152] This is the connection point.

[0153] For example, chemical formula 3-1 can be represented by any of chemical formulas 3-1-(i) to 3-1-(iii).

[0154] [Chemical Formula 3-1-(i)] [Chemical Formula 3-1-(ii)] [Chemical Formula 3-1-(iii)]

[0155]

[0156] In chemical formulas 3-1-(i) to 3-1-(iii),

[0157] R 3 It can be hydrogen or methyl.

[0158] R 7 It may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0159] R 17 and R 18 Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0160] R8a R 8b R 8c and R 8d Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0161] m5 is an integer between 0 and 10, and

[0162] This is the connection point.

[0163] For example, chemical formula 3-2 can be represented by any of chemical formulas 3-2-(i) to 3-2-(iii).

[0164] [Chemical Formula 3-2-(i)] [Chemical Formula 3-2-(ii)] [Chemical Formula 3-2-(iii)]

[0165]

[0166] In chemical formulas 3-2-(i) to 3-2-(iii),

[0167] R 3 It can be hydrogen or methyl.

[0168] R 7 It may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0169] L 4 It can be a substituted or unsubstituted C1 to C10 alkylene group.

[0170] R 8a R 8b R 8c and R 8d Each of these can be independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and

[0171] This is the connection point.

[0172] For example, R 5 and R 7 Each of them can be hydrogen, iodo group, hydroxyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, cyclopentyl group, cyclohexyl group, phenyl group, or a combination thereof.

[0173] For example, selected from R 6 At least one of them can be a halogen.

[0174] For example, selected from R 6a R 6b R 6c and R 6d At least one of them can be a halogen.

[0175] For example, selected from R 8 At least one of them can be a halogen.

[0176] For example, selected from R 8a R 8b R 8c and R 8d At least one of them can be a halogen.

[0177] For example, selected from R 6 At least one of them can be an iodine group.

[0178] For example, selected from R 6a R 6b R 6c and R 6d At least one of them can be an iodine group.

[0179] For example, selected from R 8 At least one of them can be an iodine group.

[0180] For example, selected from R 8a R 8b R 8c and R 8d At least one of them can be an iodine group.

[0181] The sensitivity can be further improved if the second structural unit includes an iodine group (e.g., when the second structural unit includes an iodine group).

[0182] For example, the second structural unit may be selected from groups in group II.

[0183] [Group II]

[0184]

[0185]

[0186] In group II,

[0187] R 2 and R 3 Each can be independently hydrogen or methyl, and This is the connection point.

[0188] For example, the polymer may be one of the compounds selected from Group 1 (e.g., any one of them).

[0189] [Group 1]

[0190]

[0191] (a:b=80:20) (a:b=80:20) (a:b=80:20) (a:b=80:20)

[0192] The polymer may include about 30 mol% to about 90 mol% of a first structural unit and about 10 mol% to about 70 mol% of a second structural unit.

[0193] For example, the polymer may include about 50 mol% to about 80 mol% of a first structural unit and about 20 mol% to about 50 mol% of a second structural unit.

[0194] The polymer may have a weight-average molecular weight (Mw) from about 1,000 g / mol to about 50,000 g / mol. For example, it may have a weight-average molecular weight from about 2,000 g / mol to about 30,000 g / mol, such as about 3,000 g / mol to about 20,000 g / mol, such as about 4,000 g / mol to about 10,000 g / mol, but this disclosure is not limited thereto.

[0195] The polymer may be included in an amount from about 0.1% to about 10% by weight of 100% by weight of the semiconductor photoresist composition.

[0196] Based on the total weight of 100% semiconductor photoresist composition, an organometallic compound may be included in an amount from about 0.5% to about 30% by weight.

[0197] The semiconductor photoresist composition according to one or more embodiments can enhance or improve the sensitivity of the photoresist by including organometallic compounds and polymers within the aforementioned amount range.

[0198] Organometallic compounds may be organotin compounds including at least one of organic oxygen and organic carbonyl oxygen.

[0199] Organometallic compounds can be represented by chemical formula 4.

[0200] [Chemical Formula 4]

[0201]

[0202] In chemical formula 4,

[0203] R 10It can be selected from substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C6 to C30 aralkyl.

[0204] R 11 To R 13 Each of these can be independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 aralkyl, an alkoxy, or an aryloxy-OR g (where R) g (Substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, or combinations thereof), carboxyl-OC(=O)R h (where R) h (which may be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or combinations thereof), -NR i R j (where R) i and R j Each of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -NR k (COR l (where R) k and R l Each of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -NR m C(NR n )R o (where R) m R n and R oEach of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -SR p (where R) p It can be a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), or -SC(=O)R q (where R) q (which may be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or combinations thereof).

[0205] R 11 To R 13 At least one of them may be selected from alkoxy and aryloxy-OR g (where R) g (Substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, or combinations thereof), carboxyl-OC(=O)R h (where R) h (which may be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or combinations thereof), -NR i R j (where R) i and R j Each of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -NR k (COR l (where R) k and R lEach of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -NR m C(NR n )R o (where R) m R n and R o Each of these can be independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), -SR p (where R) p It can be a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof), or -SC(=O)R q (where R) q It is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0206] R 11 To R 13 At least one of them may be selected from alkoxy or aryloxy-OR g (where R) g It can be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and a carboxyl group -OC(=O)R. h (where R) h It is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0207] In one or more embodiments, since the compound represented by chemical formula 4 includes -OR g or -OC(=O)R hAs ligands, patterns formed using semiconductor photoresist compositions containing the compounds can therefore exhibit excellent or suitable limiting resolution.

[0208] In one or more embodiments, ligand-OR g or -OC(=O)R h The solubility of the compound represented by chemical formula 4 in the solvent can be determined.

[0209] In one or more embodiments, R 10 It can be a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C2 to C8 aliphatic unsaturated organic group including one or more double or triple bonds, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C4 to C20 heteroaryl group, a carbonyl group, an ethoxy group, a propoxy group, or a combination thereof.

[0210] In one or more embodiments, R g It can be a substituted or unsubstituted C1 to C8 alkyl, a substituted or unsubstituted C3 to C8 cycloalkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0211] In one or more embodiments, R h It may be hydrogen, substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0212] In one or more embodiments, R 10 It may be methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valerate, ethoxy, propoxy, or combinations thereof.

[0213] In one or more embodiments, R g It may be ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, or combinations thereof, and

[0214] In one or more embodiments, R hIt may be hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, or combinations thereof.

[0215] In one or more embodiments, the organometallic compound may be represented by chemical formula 5 or chemical formula 6.

[0216] [Chemical Formula 5]

[0217] R 14 z SnO (2-(z / 2)-(x / 2)) (OH) x

[0218] In chemical formula 5,

[0219] R 14 It can be a C1 to C31 hydrocarbon group, 0 < z ≤ 2, and 0 < (z+x) ≤ 4;

[0220] [Chemical Formula 6]

[0221] R 15 a1 Sn b1 X c1 Y d1

[0222] In chemical formula 6,

[0223] R 15 It can be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 aliphatic unsaturated organic group including one or more double or triple bonds, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a carbonyl group, an ethylene oxide group, a propylene oxide group, or a combination thereof.

[0224] X can be sulfur (S), selenium (Se), or tellurium (Te).

[0225] Y can be -OR r or -OC(=O)R s ,

[0226] Where R rIt may be a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and

[0227] R s It may be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and

[0228] a1, b1, c1, and d1 can each be an integer in the range of 1 to 20.

[0229] The solvent contained in the semiconductor photoresist composition according to one or more embodiments may be an organic solvent, and may be, for example, an aromatic compound (e.g., xylene, toluene, etc.), an alcohol (e.g., 4-methyl-2-pentanol, 4-methyl-2-propanol, 1-butanol, methanol, isopropanol, 1-propanol), an ether (e.g., anisole, tetrahydrofuran), an ester (n-butyl acetate, propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate), a ketone (e.g., methyl ethyl ketone, 2-heptanone) or a mixture thereof, but this disclosure is not limited thereto.

[0230] In addition to the organometallic compound, (meth)acrylate polymer and solvent described above, the semiconductor photoresist composition according to one or more embodiments may also contain a resin.

[0231] The resin may be a phenolic resin comprising at least one aromatic portion of group 2.

[0232] [Group 2]

[0233]

[0234] The resin may have a weight-average molecular weight of about 500 to about 20,000.

[0235] The resin may be contained in an amount from about 0.1% to about 50% by weight, based on the total weight (e.g., amount) of 100% by weight of the semiconductor photoresist composition.

[0236] If the resin is contained in the above-mentioned amount range (for example, when the resin is contained in the above-mentioned amount range), it may have excellent or suitable etch resistance and heat resistance.

[0237] In one or more embodiments, the semiconductor photoresist composition may be composed of the above-described organometallic compounds, polymers, solvents, and resins.

[0238] The semiconductor photoresist composition according to the above embodiments may also include one or more additives as needed. Examples of additives may be surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof.

[0239] Surfactants may include, for example, alkylbenzene sulfonates, alkylpyridinium salts, polyethylene glycol, quaternary ammonium salts, or combinations thereof, but this disclosure is not limited thereto.

[0240] The crosslinking agent may be, for example, a melamine-based crosslinking agent, a substituted urea-based crosslinking agent, an acrylic crosslinking agent, an epoxy resin-based crosslinking agent, or a polymer crosslinking agent, but this disclosure is not limited thereto. The crosslinking agent may be, for example, a crosslinking agent having at least two crosslinking-forming substituents, such as methoxymethylated glycourea, butoxymethylated glycourea, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, 4-hydroxybutyl acrylate, acrylic acid, urethane acrylate, propylene methacrylate, 1,4-butanediol diglycidyl ether, glycidyl, 1,2-cyclohexanedicarboxylic acid diglycidyl ether, trimethylpropane triglycidyl ether, 1,3-bis(glycidoxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, etc.

[0241] Leveling agents can be used to improve the flatness of coatings during printing, and suitable leveling agents are available commercially.

[0242] Organic acids may include p-toluenesulfonic acid, benzenesulfonic acid, p-dodecylbenzenesulfonic acid, 1,4-naphthalenedisulfonic acid, methanesulfonic acid, fluorinated sulfonate, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or combinations thereof, but this disclosure is not limited thereto.

[0243] The quencher may be diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or a combination thereof.

[0244] The amount of each additive used can be controlled or selected according to the required or suitable properties.

[0245] In some embodiments, the semiconductor photoresist composition may further comprise a silane coupling agent as an adhesion enhancer to improve the tightness of contact with the substrate (e.g., to improve the adhesion of the semiconductor photoresist composition to the substrate). The silane coupling agent may be, for example, a silane compound comprising carbon-carbon unsaturated bonds, such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri(β-methoxyethoxy)silane; or 3-methacryloyloxypropyltrimethoxysilane, 3-acryloyloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloyloxypropylmethyldimethoxysilane, 3-methacryloyloxypropylmethyldiethoxysilane; trimethoxy[3-(phenylamino)propyl]silane, etc., but this disclosure is not limited thereto.

[0246] Semiconductor photoresist compositions can be formed into patterns with a high aspect ratio without collapse. Therefore, in order to form fine patterns with widths of, for example, about 5 nanometers to about 100 nanometers, about 5 nanometers to about 80 nanometers, about 5 nanometers to about 70 nanometers, about 5 nanometers to about 50 nanometers, about 5 nanometers to about 40 nanometers, about 5 nanometers to about 30 nanometers, or about 5 nanometers to about 20 nanometers. In one or more embodiments, the semiconductor photoresist composition can be used in photoresist processes using light in the wavelength range of about 5 nanometers to about 150 nanometers, for example, about 5 nanometers to about 100 nanometers, about 5 nanometers to about 80 nanometers, about 5 nanometers to about 50 nanometers, about 5 nanometers to about 30 nanometers, or about 5 nanometers to about 20 nanometers. Therefore, the semiconductor photoresist composition according to one or more embodiments can be used to achieve extreme ultraviolet lithography using an EUV light source with a wavelength of about 13.5 nanometers.

[0247] According to one or more embodiments, a method for forming a pattern using the above-described semiconductor photoresist composition is provided. For example, the pattern formed may be a photoresist pattern.

[0248] A method for forming a pattern according to one or more embodiments includes: forming an etch target layer (e.g., an etch object layer) on a substrate, coating a semiconductor photoresist composition on the etch target layer to form a photoresist film, patterning the photoresist film to form a photoresist pattern, and using the photoresist pattern as an etch mask to etch the etch target layer.

[0249] In the following text, by reference Figures 1A to 1E This describes a method for forming patterns using semiconductor photoresist compositions. Figures 1A to 1E It is a cross-sectional view used to illustrate or explain a method of forming a pattern using a semiconductor photoresist composition according to one or more embodiments.

[0250] Reference Figure 1AAn object for etching (e.g., an etching target layer or an etching object layer) is prepared. The object for etching may be a thin film 102 formed on the semiconductor substrate 100. In the following, the object for etching is limited to the thin film 102. The surface of the thin film 102 is washed to remove impurities and the like remaining thereon. The thin film 102 may be, for example, a silicon nitride layer, a polysilicon layer, or a silicon oxide layer.

[0251] Subsequently, the resist underlayer composition for forming the resist underlayer 104 is spin-coated onto the surface of the washed film 102. However, this disclosure is not limited thereto, and various known coating methods can be used, such as spraying, dip coating, blade coating, printing methods (e.g., inkjet printing and screen printing), etc.

[0252] In one or more embodiments, a coating process for the resist underlayer may not be required, while a coating process including the resist underlayer is described below.

[0253] The coated resist underlayer composition is then dried and baked to form a resist underlayer 104 on the film 102. Baking may be performed at about 100°C to about 500°C, for example, about 100°C to about 300°C.

[0254] The resist underlayer 104 is formed between the substrate 100 and the photoresist film 106, and thus can prevent or reduce non-uniformity in the patterning properties of the photoresist linewidth if rays reflected from the interface between the substrate 100 and the photoresist film 106 or from the hard mask between the layers are scattered into unintended photoresist areas (e.g., when rays reflected from the interface between the substrate 100 and the photoresist film 106 or from the hard mask between the layers are scattered into unintended photoresist areas).

[0255] Reference Figure 1B A photoresist film 106 is formed by coating a semiconductor photoresist composition onto a resist substrate 104. The photoresist film 106 is obtained by coating the aforementioned semiconductor photoresist composition onto a thin film 102 formed on a substrate 100 and then curing it by heat treatment.

[0256] For example, patterning using a semiconductor photoresist composition may include coating the semiconductor photoresist composition onto a substrate 100 having a thin film 102 by spin coating, slot coating, inkjet printing, etc., and then drying it to form a photoresist film 106.

[0257] The semiconductor photoresist composition has been described and illustrated in detail, and will not be repeated here.

[0258] Subsequently, the substrate 100 having the photoresist film 106 is subjected to a first baking process. The first baking process may be performed at approximately 80°C to approximately 120°C.

[0259] Reference Figure 1C The photoresist film 106 can be selectively exposed using a patterned mask 110.

[0260] For example, exposure can use activation radiation that utilizes the following types of light: high-energy wavelengths such as extreme ultraviolet (EUV; wavelength approximately 13.5 nm) and electron beam (E-Beam); and shorter wavelengths such as i-line (wavelength approximately 365 nm), KrF excimer laser (wavelength approximately 248 nm), and ArF excimer laser (wavelength approximately 193 nm).

[0261] For example, the light or exposure beam used for exposure according to one or more embodiments may be short-wavelength light having a wavelength in the range of about 5 nanometers to about 150 nanometers and / or a high-energy wavelength, such as extreme ultraviolet (EUV; wavelength of 13.5 nanometers), and / or may be an electron beam (E-Beam), etc.

[0262] A polymer is formed through cross-linking reactions, such as condensation, between organometallic compounds, thereby giving the exposed area 106b of the photoresist film 106 a different solubility than the unexposed area 106a of the photoresist film 106.

[0263] Subsequently, the substrate 100 is subjected to a second baking process. The second baking process can be performed at a temperature of about 90°C to about 200°C. Due to the second baking process, the exposure area 106b of the photoresist film 106 easily becomes insoluble relative to the developer.

[0264] exist Figure 1D In this process, a developer is used to dissolve and remove the unexposed areas 106a of the photoresist film to form a photoresist pattern 108. For example, an organic solvent such as 2-heptanone is used to dissolve and remove the unexposed areas 106a of the photoresist film to complete the photoresist pattern 108 corresponding to a negative image.

[0265] As described herein, the developer used in the pattern forming method according to one or more embodiments may be an organic solvent. The organic solvent used in the pattern forming method according to one or more embodiments may be, for example: ketones, such as methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, etc.; alcohols, such as 4-methyl-2-propanol, 1-butanol, isopropanol, 1-propanol, methanol, etc.; esters, such as propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate, n-butyl acetate, butyrolactone, etc.; aromatic compounds, such as benzene, xylene, toluene, etc.; or combinations thereof.

[0266] However, the photoresist pattern according to one or more embodiments is not limited to a negative image, but can be formed to have a positive image. Here, the developer used to form the positive image can be a quaternary ammonium hydroxide composition, such as tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, or any suitable combination thereof.

[0267] As described herein, exposure to high-energy light, such as extreme ultraviolet (EUV; wavelength 13.5 nm) and electron beams (E-Beam), and shorter wavelength light, such as i-lines (wavelength approximately 365 nm), KrF excimer lasers (wavelength approximately 248 nm), and ArF excimer lasers (wavelength approximately 193 nm), can provide a photoresist pattern 108 with a width of approximately 5 nm to approximately 100 nm. For example, the photoresist pattern 108 may have a width of approximately 5 nm to approximately 90 nm, approximately 5 nm to approximately 80 nm, approximately 5 nm to approximately 70 nm, approximately 5 nm to approximately 60 nm, approximately 5 nm to approximately 50 nm, approximately 5 nm to approximately 40 nm, approximately 5 nm to approximately 30 nm, or approximately 5 nm to approximately 20 nm.

[0268] In one or more embodiments, the photoresist pattern 108 may have a pitch (center-to-center distance between adjacent features in the pattern) of less than or equal to about 50 nanometers, for example less than or equal to about 40 nanometers, for example less than or equal to about 30 nanometers, for example less than or equal to about 20 nanometers, or for example less than or equal to about 15 nanometers, and a linewidth roughness of less than or equal to about 10 nanometers, less than or equal to about 5 nanometers, less than or equal to about 3 nanometers, or less than or equal to about 2 nanometers.

[0269] Subsequently, the photoresist pattern 108 is used as an etching mask to etch the resist substrate 104. Through this etching process, an organic film pattern 112 is formed. The organic film pattern 112 may also have a width corresponding to the width of the photoresist pattern 108.

[0270] Reference Figure 1E The exposed thin film 102 is etched by using a photoresist pattern 108 as an etching mask. Thus, the thin film is formed into a thin film pattern 114.

[0271] In the exposure process, the thin film pattern 114 formed using the photoresist pattern 108 can have a width corresponding to the width of the photoresist pattern 108, which is formed by an exposure process using an EUV light source. For example, the thin film pattern 114 can have a width (e.g., linewidth) from about 5 nanometers to about 100 nanometers, which is equal to the width of the photoresist pattern 108. For example, like the width of the photoresist pattern 108, the thin film pattern 114 formed using the photoresist pattern 108 can have a width (e.g., linewidth) from about 5 nanometers to about 90 nanometers, from about 5 nanometers to about 80 nanometers, from about 5 nanometers to about 70 nanometers, from about 5 nanometers to about 60 nanometers, from about 5 nanometers to about 50 nanometers, from about 5 nanometers to about 40 nanometers, from about 5 nanometers to about 30 nanometers, or from about 5 nanometers to about 20 nanometers, for example, having a width (e.g., linewidth) less than or equal to about 20 nanometers, which is formed by an exposure process using an EUV light source.

[0272] The present disclosure will be described in more detail below through examples of preparing the above-described semiconductor photoresist compositions. However, the present disclosure is not technically limited to the following examples.

[0273] Example

[0274] Synthesis of organometallic compounds

[0275] Synthesis example 1

[0276] 40.7 g of tert-butylSnPh3 and 300 g of propionic acid were added to a 250 mL double-necked round-bottom flask and heated under reflux for 24 hours.

[0277] Unreacted propionic acid was removed under reduced pressure, thus yielding the compound represented by chemical formula 7.

[0278] [Chemical Formula 7]

[0279]

[0280] Synthesis example 2

[0281] 30 mL of anhydrous pentane was added to 10 g of tert-amyl SnCl3, the temperature was maintained at 0 °C, and then 7.4 g of diethylamine and 6.1 g of ethanol were added, and the mixture was stirred at room temperature for 1 hour. When the reaction was complete, the product was filtered, concentrated, and vacuum dried to obtain the compound represented by chemical formula 8.

[0282] [Chemical Formula 8]

[0283]

[0284] Synthesis example 3

[0285] 10 g of dichlorodibutyltin was dissolved in 30 mL of ether, and 70 mL of 1 M sodium hydroxide (NaOH) aqueous solution was added. The mixture was then stirred for 1 hour. After stirring, the resulting solid was filtered, washed three times with 25 mL of deionized water, and dried under reduced pressure at 100 °C to obtain an organometallic compound represented by Formula 9 with a weight-average molecular weight of 1,500.

[0286] [Chemical Formula 9]

[0287]

[0288] Polymer Synthesis

[0289] Synthesis example 4

[0290] Under a nitrogen atmosphere, 17.85 g of the compound represented by Formula 1a (Camoptics Co., Ltd.), 3.72 g of the compound represented by Formula 1b (DIHS, AcellaChemBio Co., Ltd.), and 89.72 g of diisopentyl ether (DIAE) were added to a 250 mL double-necked round-bottom flask, and the mixture was then heated to an internal temperature of 115 °C. When the internal temperature reached 115 °C, 13.82 g of a 25 wt% V-601 / DIAE solution (3.45 g of V-601) was slowly added, and after 6 hours, the reaction solution was cooled to room temperature, and the reaction mixture was concentrated to a 50% solids content (e.g., amount). After adding 120 g of heptane to the concentrated solution, the resulting polymer was filtered. The filtered polymer was completely dissolved in 12 g of DIAE, and then 270 g of heptane was added to the solution. Precipitation was carried out using g of heptane (this process was repeated twice), and then the mixture was completely dried to finally obtain copolymer R1 (Mw=5,000).

[0291] [Chemical Formula 1a] [Chemical Formula 1b]

[0292]

[0293] [Copolymer R1]

[0294] Copolymer R1 (a:b=80:20)

[0295] Synthesis example 5

[0296] Except that 3.72 g of the compound represented by chemical formula 2b (DIHS, Essella Chemical Bio Ltd.) was used instead of the compound represented by chemical formula 1b in Synthesis Example 4, copolymer R2 (Mw=5,000) was obtained in substantially the same manner as in Synthesis Example 4.

[0297] [Chemical Formula 2b]

[0298]

[0299] [Copolymer R2]

[0300] Copolymer R2 (a:b=80:20)

[0301] Synthesis example 6

[0302] Except that 11.77 g of the compound represented by chemical formula 2a (HALOCARBONCorporation) was used instead of the compound represented by chemical formula 1a in Synthesis Example 4, copolymer R3 (Mw=5,000) was obtained in substantially the same manner as in Synthesis Example 4.

[0303] [Chemical Formula 2a]

[0304]

[0305] [Copolymer R3]

[0306] Copolymer R3 (a:b=80:20)

[0307] Synthesis Example 7

[0308] 17.85 g of the compound represented by Formula 1a (KEM Optical Co., Ltd.), 1.62 g of acetylated styrene (Songwon Industrial Co., Ltd.), and 81.33 g of diisopentyl ether (DIAE) were added to a 250 mL double-necked round-bottom flask under a nitrogen atmosphere and heated until the internal temperature reached 115°C. When the internal temperature reached 115°C, 13.82 g of a 25% by weight V-601 / DIAE solution (3.45 g of V-601) was slowly added, and after 6 hours, the reaction solution was cooled to room temperature, and the reaction mixture was concentrated to a 50% solids content (e.g., amount). After adding 120 g of heptane to the concentrated solution, the resulting polymer was filtered. The filtered polymer was completely dissolved in 12 g of DIAE, and then 270 g of heptane was added to precipitate the polymer (twice), and then completely dried to obtain the intermediate polymer. 10 g of the intermediate polymer was mixed with 20 g of acetone and 50 g of methanol and allowed to dissolve completely. Then, 40 g of 25% sodium methoxide was added to the mixture at room temperature, and the reaction was carried out at 25°C for 6 hours. The reaction was then neutralized in a 3% aqueous acetic acid solution for 30 minutes to complete the reaction. The solvent was then recovered under reduced pressure via vacuum and replaced with ethyl acetate to obtain a solution with a solids content of 20% (e.g., amount). 50 g of the solution was washed twice with 100 g of ultrapure water and then dried to obtain the final copolymer R4 (Mw = 5,000).

[0309] [Copolymer R4]

[0310] Copolymer R4 (a:b=80:20)

[0311] Preparation of semiconductor photoresist compositions

[0312] Examples 1 to 10 and Comparative Example 1

[0313] The organometallic compounds represented by chemical formulas 7 to 9 according to Synthesis Examples 1 to 3, and polymers R1 to R4 according to Synthesis Examples 4 to 7, were dissolved in propylene glycol methyl ether acetate (PGMEA) at the weight ratios shown in Table 1, and then filtered through a 0.1-micron (μm) polytetrafluoroethylene (PTFE) syringe filter, thereby preparing each semiconductor photoresist composition according to Examples 1 to 10 and Comparative Example 1.

[0314] [Table 1]

[0315]

[0316] Evaluation: Sensitivity and Line Edge Roughness (LER) Assessment

[0317] Each of the photoresist compositions according to the examples and comparative examples was spin-coated at 1500 rpm onto a 200 mm circular silicon wafer for 30 seconds, the surface of which was deposited with hexamethyldisilazane (HMDS), and baked at 110 °C for 60 seconds. Post-application baking (PAB) was then performed, followed by placement at room temperature (23 ± 2 °C) for 30 seconds.

[0318] Then, a linear array of 50 circular pads with a diameter of 500 μm was projected onto a wafer coated with a photoresist composition using extreme ultraviolet (EUV) light (Lawrence Berkeley National Laboratory Micro Exposure Tool, MET). Here, the pad exposure time was adjusted to ensure that an increased dose of EUV light was applied to each pad.

[0319] Then, after exposure, the photoresist and substrate are baked on a hot plate at 160°C for 120 seconds. The baked film is then developed in PGMEA solvent to form a negative image. Finally, the obtained film is baked again on a hot plate at 150°C for 2 minutes to complete the process.

[0320] The residual photoresist thickness of the exposed pad was measured using an ellipsometry. The residual thickness was measured at each exposure dose and plotted as a function of exposure dose to measure sensitivity. After measuring the line edge roughness (LER) from field emission scanning electron microscopy (FE-SEM) images, the sensitivity and line edge roughness were evaluated according to the following criteria, and the results are shown in Table 2.

[0321] Sensitivity evaluation criteria

[0322] - A: Less than 50 millijoules / cm² (mJ / cm²) 2 )

[0323] - B: Greater than or equal to 50 mJ / cm 2

[0324] LER Evaluation Standards

[0325] -○: Less than or equal to 2 nanometers (nm)

[0326] -△: Greater than 2 nanometers and less than or equal to 5 nanometers

[0327] - X: Greater than 5 nanometers

[0328] [Table 2]

[0329]

[0330] According to the results in Table 2, compared with the comparative examples, the patterns formed using the semiconductor photoresist compositions according to the present disclosure exhibit enhanced (e.g., superior) sensitivity and LER characteristics.

[0331] The terms “and / or” and “or” as used herein can include any and all combinations of one or more of the items in the relevant list. The “ / ” used below may be interpreted as “and” or “or” as appropriate. In this disclosure, expressions such as “at least one of…”, “one of…”, and “selected from”, when placed before a list element, modify the entire list, not individual elements. For example, “at least one of a, b, or c”, “selected from at least one of a, b, and c”, “selected from at least one of a to c”, etc., can indicate that only a is included, only b is included, only c is included, including (e.g., both a and b are included), including (e.g., both a and c are included), including (e.g., both b and c are included), including all of a, b, and c, or variations thereof.

[0332] It will also be understood that the terms “comprise(s) / comprising,” “include(s) / including,” or “have / has / having,” when used in this disclosure, specify the presence of the stated feature, integer, step, operation, element, and / or component, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. Furthermore, the terms “comprise(s) / comprising,” “include(s) / including,” “have / has / having,” or other similar terms include or support the terms “composed of…” and “essentially composed of…,” which indicate the presence of the stated feature, integer, step, operation, element, and / or component, and the absence or essential absence of other features, integers, steps, operations, elements, components, and / or groups thereof.

[0333] Unless the context clearly indicates otherwise, the singular forms “a / an” and “the” as used herein are intended to include the plural forms as well. Furthermore, the use of “may” in describing embodiments of this disclosure refers to “one or more embodiments of this disclosure”.

[0334] In the context of this disclosure and unless otherwise defined, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0335] The term “about” or similar terms used herein are used as approximate terms rather than as terms of degree, and are intended to describe the inherent bias of a measured or calculated value that would be recognized by one of ordinary skill in the art. Taking into account the measurements discussed and the errors associated with the measurement of a particular quantity (i.e., limitations of the measurement system), “about” or “approximately” as used herein also includes stated values ​​and refers to values ​​within an acceptable range of deviation for a particular value as determined by one of ordinary skill in the art. For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0336] Any numerical range described herein is intended to include all subranges of the same numerical precision falling within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the minimum value 1.0 and the maximum value 10.0 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as (for example) 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit described herein is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly describe any subrange falling within the scope expressly described herein.

[0337] In view of the full contents of this disclosure, those skilled in the art will understand that each suitable feature of the various embodiments of this disclosure may be combined or integrated with each other in part or in whole, and may be technically interlocked and operated in a variety of suitable manners, and that each embodiment may be implemented independently of each other or in any suitable combination with each other unless otherwise stated or implied.

[0338] The pattern forming apparatus, semiconductor forming apparatus, and / or any other related apparatus or component according to embodiments of the invention set forth herein can be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, various components of the apparatus may be formed on an integrated circuit (IC) chip or on a discrete IC chip. Furthermore, various components of the apparatus may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. Additionally, various components of the apparatus may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components to perform the various functions set forth herein. The computer program instructions are stored in memory, which may be implemented in a computing device using standard memory devices (e.g., for example, random access memory (RAM)). The computer program instructions may also be stored in other non-transitory computer-readable media (e.g., for example, compact disc read-only memory (CD-ROM), flash memory drives, etc.). Furthermore, those skilled in the art will recognize that, without departing from the scope of this disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed across one or more other computing devices.

[0339] In the foregoing, certain embodiments have been described and illustrated. However, it will be apparent to those skilled in the art that this disclosure is not limited to the described embodiments and that modifications and variations can be made without departing from the spirit and scope of this disclosure. Therefore, the modified or varied embodiments may be understood without being separated from the technical concept and aspects of this disclosure, and the modified embodiments are within the scope of the claims of this disclosure and their equivalents.

Claims

1. A semiconductor photoresist composition comprising: Organometallic compounds; Polymers, including: First structural unit; as well as Second structural unit, The first structural unit is represented by the chemical formula M-1, and The second structural unit is represented by chemical formula 2 or chemical formula 3; as well as solvent, [Chemical Formula M-1] [Chemical Formula 2] [Chemical Formula 3] ， Among chemical formulas M-1, 2, and 3, R 1 To R 3 Each is independently hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group. L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a combination thereof. X 1 For single bonds, -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O)-, -C(=O)O-, -OC(=O), -OC(=O)O-, -NR a - or a combination thereof, R a It is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group. X 2 It is a single bond, -C(=O)-, or a substituted or unsubstituted C1 to C10 alkylene group. X 3 For single key, -L 4 -O-, or substituted or unsubstituted C1 to C10 alkylene groups, L 4 It is a substituted or unsubstituted C1 to C10 alkylene group. R 4 It is hydrogen, fluorine, hydroxyl, substituted or unsubstituted C1 to C20 alkyl, or a combination thereof. Selected from R 4 L 1 and L 2 At least one of them includes fluorine and hydroxyl, R 5 It is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. R 6 To R 8 Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. m1 and m2 are each independent integers from 1 to 4, and This is the connection point.

2. The semiconductor photoresist composition according to claim 1, wherein... The first structural unit is represented by chemical formula 1: [Chemical Formula 1] ,and In chemical formula 1, R 1 It is hydrogen, or a substituted or unsubstituted C1 to C10 alkyl group. R c R d R e R f and R 4 Each is independently hydrogen, fluorine, hydroxyl, substituted or unsubstituted C1 to C20 alkyl, or a combination thereof. m3 and m4 are each independent integers from 1 to 10. X 1 For single bonds, -O-, -S-, -S(=O)-, -S(=O)2-, -C(=O)-, -C(=O)O-, -OC(=O), -OC(=O)O-, -NR a - or a combination thereof, R a It is hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, and Selected from R c R d R e R f and R 4 At least one of them includes fluorine and hydroxyl.

3. The semiconductor photoresist composition according to claim 1, wherein... The first structural unit is selected from at least one of group I: [Group I] ,and In group I, R 1 Each is independently hydrogen or methyl, and This is the connection point.

4. The semiconductor photoresist composition according to claim 1, wherein... The second structural unit is represented by chemical formula 2-1 or chemical formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] ,and In chemical formulas 2-1 and 2-2, R 2 R 5 R 6 and m 1 As defined in chemical formula 2, and This is the connection point.

5. The semiconductor photoresist composition according to claim 4, wherein... The second structural unit is represented by any one of chemical formulas 2-1-(i) to 2-1-(iv): [Chemical Formula 2-1-(i)] [Chemical Formula 2-1-(ii)] [Chemical Formula 2-1-(iii)] [Chemical Formula 2-1-(iv)] ,and Among them, in chemical formulas 2-1-(i) to 2-1-(iv), R 2 It is hydrogen or methyl. R 5 R 5a and R 5b Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. R 6a R 6b R 6c and R 6d Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and This is the connection point.

6. The semiconductor photoresist composition according to claim 4, wherein... The second structural unit is represented by any one of chemical formulas 2-2-(i) to 2-2-(iii): [Chemical Formula 2-2-(i)] [Chemical Formula 2-2-(ii)] [Chemical Formula 2-2-(iii)] ,and Among them, in chemical formulas 2-2-(i) to 2-2-(iii), R 2 It is hydrogen or methyl. R 5 It is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. R 6a R 6b R 6c and R 6d Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and This is the connection point.

7. The semiconductor photoresist composition according to claim 1, wherein... The second structural unit is represented by chemical formula 3-1 or chemical formula 3-2: [Chemical Formula 3-1] [Chemical Formula 3-2] ,and In chemical formulas 3-1 and 3-2, R 3 R 8 R 7 L 4 And m2 as defined in chemical formula 3, R 17 and R 18 Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. m5 is an integer between 0 and 10, and This is the connection point.

8. The semiconductor photoresist composition according to claim 7, wherein... The second structural unit is represented by any one of chemical formulas 3-1-(i) to 3-1-(iii): [Chemical Formula 3-1-(i)] [Chemical Formula 3-1-(ii)] [Chemical formula 3-1-(iii)] ,and Among them, in chemical formulas 3-1-(i) to 3-1-(iii), R 3 It is hydrogen or methyl. R 7 It is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. R 17 and R 18 Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. R 8a R 8b R 8c and R 8d Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. m5 is an integer between 0 and 10, and This is the connection point.

9. The semiconductor photoresist composition according to claim 7, wherein... The second structural unit is represented by any one of chemical formulas 3-2-(i) to 3-2-(iii): [Chemical Formula 3-2-(i)] [Chemical Formula 3-2-(ii)] [Chemical formula 3-2-(iii)] ,and Among them, in chemical formulas 3-2-(i) to 3-2-(iii), R 3 It is hydrogen or methyl. R 7 It is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. L 4 It is a substituted or unsubstituted C1 to C10 alkylene group. R 8a R 8b R 8c and R 8d Each of the following is independently hydrogen, halogen, hydroxyl, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and This is the connection point.

10. The semiconductor photoresist composition according to claim 1, wherein... The second structural unit is at least one of the groups selected from group II: [Group II] ,and In group II, R 2 and R 3 Each is independently hydrogen or methyl, and This is the connection point.

11. The semiconductor photoresist composition according to claim 1, wherein... The polymer comprises 30 mol% to 90 mol% of the first structural unit and 10 mol% to 70 mol% of the second structural unit.

12. The semiconductor photoresist composition according to claim 1, wherein... The polymer has a weight-average molecular weight of 1,000 g / mol to 50,000 g / mol.

13. The semiconductor photoresist composition according to claim 1, wherein... The amount of the polymer is from 0.1% to 10% by weight, based on the total weight of 100% by weight of the semiconductor photoresist composition.

14. The semiconductor photoresist composition according to claim 1, wherein... The amount of the organometallic compound is from 0.5% to 30% by weight, based on the total weight of 100% by weight of the semiconductor photoresist composition.

15. The semiconductor photoresist composition according to claim 1, wherein... The organometallic compound includes at least one selected from organooxy groups and organocarbonyloxy groups.

16. The semiconductor photoresist composition according to claim 1, wherein... The organometallic compound is represented by chemical formula 4: [Chemical Formula 4] ,and In chemical formula 4, R 10 It is selected from substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C6 to C30 aralkyl. R 11 To R 13 Each of the following is independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 aralkyl, an alkoxy, or an aryloxy-OR g Carboxyl group -OC(=O)R h -NR i R j -NR k (COR l -NR m C(NR n )R o -SR p 、or -SC(=O)R q , Where R g It can be a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Where R h It is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Where R i and R j Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Where R k and R l Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Where R m R n and R o Each of the following is independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof. Where R p It can be a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, or Where R q It is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof. R 11 To R 13 At least one of them is selected from -OR g -OC(=O)R h -NR i R j -NR k (COR l -NR m C(NR n )R o -SR p 、or -SC(=O)R q .

17. The semiconductor photoresist composition according to claim 16, wherein... R 11 To R 13 At least one of them is selected from -OR g or -OC(=O)R h .

18. The semiconductor photoresist composition according to claim 17, wherein... R 10 The substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 aliphatic unsaturated organic groups including one or more double or triple bonds, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C4 to C20 heteroaryl, carbonyl, ethoxy, propoxy, or combinations thereof, R g It is a substituted or unsubstituted C1 to C8 alkyl, a substituted or unsubstituted C3 to C8 cycloalkyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and R h It is hydrogen, substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

19. The semiconductor photoresist composition according to claim 1, wherein... The organometallic compound is represented by chemical formula 5 or chemical formula 6: [Chemical Formula 5] R 14 z SnO (2-(z / 2)-(x / 2)) (OH) x , In chemical formula 5, R 14 It consists of C1 to C31 hydrocarbon groups. 0 < z ≤ 2, and 0 <(z+x)≤4; [Chemical Formula 6] R 15 a1 Sn b1 X c1 Y d1 , and In chemical formula 6, R 15 The substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C3 to C20 cycloalkyl groups, substituted or unsubstituted C2 to C20 aliphatic unsaturated organic groups including one or more double or triple bonds, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C4 to C30 heteroaryl groups, carbonyl groups, ethylene oxide groups, propylene oxide groups, or combinations thereof. X represents sulfur, selenium, or tellurium. Y is -OR r or -OC(=O)R s , Where R r It is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and R s It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and a1, b1, c1, and d1 are each an independent integer from 1 to 20.

20. A method for forming a pattern, comprising: Form the etch target layer on the substrate; A semiconductor photoresist composition as described in any one of claims 1 to 19 is coated on the etched target layer to form a photoresist film; The photoresist film is patterned to form a photoresist pattern; as well as The photoresist pattern is used as an etching mask to etch the target layer.

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