Semiconductor photoresist composition and method of forming pattern using the same

Abstract

A semiconductor photoresist composition and a method of forming or providing a pattern using the semiconductor photoresist composition are disclosed. A semiconductor photoresist composition may include a tin (Sn)-containing organometallic compound; at least one of sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements; and a solvent.

Description

[0001] Cross-citation of related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0065314, filed with the Korean Intellectual Property Office on May 20, 2024, the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] One or more embodiments of this disclosure relate to semiconductor photoresist compositions and methods of forming or providing patterns using said semiconductor photoresist compositions. Background Technology

[0004] Extreme ultraviolet (EUV) lithography has attracted attention as a technology for manufacturing next-generation semiconductor devices. EUV lithography is a patterning technique that uses EUV rays with a wavelength of 13.5 nanometers as the exposure source. According to EUV lithography, fine patterns (e.g., less than or equal to 20 nanometers) can be formed in the exposure process during the manufacturing of semiconductor devices (e.g., semiconductor chips).

[0005] Extreme ultraviolet (EUV) lithography is achieved by developing compatible photoresists that can be applied at a spatial resolution of 16 nanometers or less. Efforts have been made or are underway to meet the insufficient specifications of chemically amplified (CA) photoresists for next-generation devices, such as resolution, photosensitivity, and feature roughness (also known as line edge roughness or LER).

[0006] The inherent image blurring caused by acid-catalyzed reactions in photoresists of certain polymer types or varieties limits the resolution of small feature sizes, a situation that has always existed in electron beam lithography. Chemically amplified (CA) photoresists are designed for high sensitivity. However, their sensitivity may be reduced due to their elemental composition, which decreases light absorption at a wavelength of 13.5 nm, and CA photoresists may encounter more difficulties under EUV exposure.

[0007] The inherent image blurring caused by acid-catalyzed reactions in polymer-type or variety photoresists limits the resolution in small feature sizes present in electron beam lithography. Due to these defects and problems of chemically amplified photoresists, the semiconductor industry needs or demands a new type of high-performance photoresist.

[0008] To overcome the drawbacks of the aforementioned chemically amplified (CA) organic photosensitive compositions, inorganic photosensitive compositions have been investigated. Inorganic photosensitive compositions are primarily used for negative tone patterns that are resistant to removal of the developer composition due to chemical modification via non-chemical amplification mechanisms. Inorganic compositions comprise inorganic elements with higher EUV absorbance than hydrocarbons; therefore, they can ensure sensitivity via non-chemical amplification mechanisms and may be less sensitive to stochastic effects, thus potentially exhibiting low line edge roughness and a relatively small number of defects.

[0009] Tungsten-based peroxypolyacids mixed with tungsten, niobium, titanium and / or tantalum have been reported as radiation-sensitive materials for patterning.

[0010] These materials are effective for large-pitch patterning of dual-layer configurations under far-ultraviolet (deep ultraviolet), X-ray, and electron beam light sources. Improved performance was achieved when using cationic hafnium metal oxide sulfate (HfSOx) materials with a peroxide complexing agent to image 15 nm half-pitch (HP) via projection EUV exposure. The system exhibits high performance for non-chemically amplified photoresists and has a practical photosensitivity close to that required for EUV photoresists. However, hafnium metal oxide sulfate materials containing a peroxide complexing agent have some practical drawbacks. First, these materials are coated in a corrosive sulfuric acid / hydrogen peroxide mixture and have insufficient shelf-life stability. Second, modifying the material structure as a composite mixture to improve performance is challenging. Third, development should be carried out in a high-concentration 25 wt% tetramethylammonium hydroxide (TMAH) solution and / or similar solutions.

[0011] To address these issues, research has focused on developing tin (Sn)-containing molecules with excellent or adequate extreme ultraviolet (EUV) light absorption. For organotin polymers within tin-containing molecules, alkyl ligands dissociate via light absorption or the generation of secondary electrons. The dissociated alkyl ligands then crosslink with adjacent chains via oxo bonds, achieving negative patterning that is not removed by organic developers. While such organotin polymers exhibit improved sensitivity while maintaining the desired resolution and line edge roughness, further refinement of the patterning properties may be needed for commercial availability. Summary of the Invention

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

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

[0014] Other aspects of the embodiments will be set forth in the description which follows, and will be apparent in part from 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 may include a tin (Sn) organometallic compound; at least one selected from sulfonic acid compounds containing (or including) at least one halogen element (e.g., at least one halogen atom) and sulfonamide compounds containing (or including) at least one halogen element (e.g., at least one halogen atom); and a solvent.

[0016] A method of forming or providing a pattern according to one or more embodiments may include forming or providing an etch target layer on a substrate, coating a semiconductor photoresist composition on the etch target layer to form or provide a photoresist film, patterning the photoresist film to form or provide a photoresist pattern, and using the photoresist pattern as an etch mask to etch the etch target layer.

[0017] The semiconductor photoresist composition according to one or more embodiments can achieve excellent or appropriate sensitivity, excellent or appropriate LER and / or excellent or appropriate surface roughness characteristics. Attached Figure Description

[0018] The above and other aspects and features of certain embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:

[0019] Figures 1A-1E Each is a cross-sectional view illustrating a method of forming or providing a pattern using a semiconductor photoresist composition according to one or more embodiments.

[0020] Explanation of icon numbers

[0021] 100: Substrate;

[0022] 102: Film;

[0023] 104: Resist underlayer;

[0024] 106: Photoresist film;

[0025] 106a: Unexposed area;

[0026] 106b: Exposure area;

[0027] 108: Photoresist pattern;

[0028] 110: Patterned mask;

[0029] 112: Organic thin film pattern;

[0030] 114: Thin film pattern. Detailed Implementation

[0031] Hereinafter, one or more embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. In the following description of the present disclosure, functions or structures that would normally be understood by one of ordinary skill in the art may not be described in order to clarify the present disclosure.

[0032] To clearly illustrate the embodiments of this disclosure, certain descriptions and relationships may be omitted, and throughout this disclosure, substantially identical or similar configurations or arrangements of elements may be represented by the same reference numerals. Furthermore, since the dimensions and thicknesses of each configuration or arrangement shown in the drawings may be arbitrarily shown for better understanding and ease of description, the embodiments of this disclosure are not necessarily limited thereto.

[0033] In the accompanying drawings, the thickness of layers, films, panels, regions, and / or the like may be enlarged for clarity. The thickness of portions of layers or regions and / or the like may be exaggerated for clarity. It will be understood that if (e.g., when) an element, such as a layer, film, region, or substrate, is referred to as "on" another element, it may be directly on the other element or there may be intervening elements present. If (e.g., when) an element is referred to as "directly on" another element, there may be no intervening elements present.

[0034] As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms unless the context clearly indicates otherwise. Furthermore, the use of "may" in describing embodiments of this disclosure means "one or more embodiments of this disclosure."

[0035] In the context of this disclosure, unless otherwise defined, the terms "use", "used" and "being used" may be considered synonymous with the terms "utilize", "utilized" and "being exploited", respectively.

[0036] As used herein, the term "about" or similar terms are used as approximations rather than terms of degree, intended to account for the inherent biases in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. "About" or "approximately" as used herein also includes the value and means within an acceptable range of deviation for a particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and errors associated with the measurement of the particular quantity (e.g., limitations of the measurement system). For example, "about" may refer to one or more standard deviations of the value, or within ±30%, 20%, 10%, or 5% of the value.

[0037] Any numerical range described herein is intended to include all subranges containing substantially the same numerical precision within the stated range. For example, the range "1.0 to 10.0" is intended to include all subranges between (and including) the minimum value of 1.0 and the maximum value of 10.0, 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 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly represent any subranges contained within the range expressly stated herein.

[0038] As used herein, "substituted" means that the hydrogen atom is replaced by deuterium, a halogen atom (F, Cl, Br, or I), a hydroxyl group, a thiol group, a cyano group, a nitro group, -NRR' (where 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), or -SiRR'R" (where R, R' and R" can each independently 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, a C1 to C30 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a C1 to C20 sulfide group, or a combination thereof. "Unsubstituted" means that the hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0039] As used herein, unless otherwise defined (e.g., when), "alkyl" refers to a straight-chain or branched aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl" that does not contain any double or triple bonds.

[0040] The alkyl group can be a C1 to C8 alkyl group. For example, the alkyl group can be a C1 to C7 alkyl group, a C1 to C6 alkyl group, or a C1 to C5 alkyl group. For example, the C1 to C5 alkyl group can be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or 2,2-dimethylpropyl.

[0041] As used herein, unless otherwise defined (e.g., when), "cycloalkyl" refers to a monovalent cyclic aliphatic hydrocarbon group.

[0042] The cycloalkyl group can be a C3 to C8 cycloalkyl group, for example, a C3 to C7 cycloalkyl group, or a C3 to C6 cycloalkyl group. For example, the cycloalkyl group can be cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, but the embodiments of this disclosure are not limited thereto.

[0043] As used herein, "aryl" refers to a cyclic substituent in which all atoms have p orbitals and these p orbitals are conjugated, and may include monocyclic, polycyclic, or fused ring (e.g., a ring sharing adjacent carbon atom pairs) functional groups.

[0044] As used herein, "heteroaryl" can refer to an aryl group containing at least one heteroatom selected from nitrogen (N), oxygen (O), sulfur (S), phosphorus (P), and silicon (Si). Two or more heteroaryl groups can be directly linked by σ bonds (e.g., monocovalent bonds), or if (e.g., when) the heteroaryl group contains two or more rings, the two or more rings can be fused. If (e.g., when) the heteroaryl group is a fused ring, each ring can contain one to three heteroatoms.

[0045] As used herein, unless otherwise defined, "alkenyl" refers to an unsaturated aliphatic alkenyl group containing at least one double bond as a straight-chain or branched aliphatic hydrocarbon group.

[0046] As used herein, unless otherwise defined, "alkynyl" means an unsaturated aliphatic alkynyl group containing at least one triple bond as a straight-chain or branched aliphatic hydrocarbon group.

[0047] The following describes a semiconductor photoresist composition according to one or more embodiments.

[0048] The semiconductor photoresist composition according to one or more embodiments may include a tin (Sn)-containing organometallic compound, at least one selected from a sulfonic acid compound containing one or more halogen elements (e.g., one or more halogen atoms) and a sulfonamide compound containing one or more halogen elements (e.g., one or more halogen atoms), and a solvent.

[0049] The semiconductor photoresist composition may contain halogen atom (F, Cl, Br or I) functional groups (e.g., one or more halogen atoms) in the sulfonic acid compound, thereby improving or enhancing sensitivity and / or line edge roughness (LER) to surface roughness characteristics and / or achieving or providing excellent or adequate resolution.

[0050] Sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements can be represented by chemical formula 1 or chemical formula 2.

[0051] Chemical Formula 1

[0052]

[0053] Chemical formula 2

[0054]

[0055] In chemical formula 1 and chemical formula 2,

[0056] R 1 and R 3 To R 6 Each of these can be independently hydrogen, a halogen atom (F, Cl, Br, or I), a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C2 to C10 alkenyl, a substituted or unsubstituted C2 to C10 alkynyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C3 to C20 cycloalkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocycloalkyl, a substituted or unsubstituted C2 to C30 heterocycloalkenyl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof.

[0057] R 3 To R 6 They can be independently connected or coupled (e.g., covalently connected or coupled) to form or provide substituted or unsubstituted C5 to C20 heterocyclic alkyl groups.

[0058] R 2 It can be hydroxyl, amino, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryloxy, substituted or unsubstituted C1 to C20 alkylamino, or substituted or unsubstituted C6 to C20 aromaticamino.

[0059] L 1 and L 2 Each of these can be independently a single bond (e.g., a monocovalent bond), a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 ynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0060] From R 1 R 2 and L 1At least one of the selected components may be a halogen atom (F, Cl, Br, or I); a C1 to C10 alkyl group substituted with one or more halogens (e.g., one or more halogen atoms); a C2 to C10 alkenyl group substituted with one or more halogens; a C2 to C10 alkynyl group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C2 to C30 heterocyclic alkyl group substituted with one or more halogens; a C2 to C30 heterocyclic alkenyl group substituted with one or more halogens; a C2 to C30 heteroaryl group substituted with one or more halogens; a C1 to C20 alkoxy group substituted with one or more halogens; or a C6 to C30 aryl group substituted with one or more halogens. Substituted C6 to C20 aryloxy groups; C1 to C20 alkylamino groups substituted with one or more halogens; C6 to C20 arylamino groups substituted with one or more halogens; C1 to C10 alkylene groups substituted with one or more halogens; C2 to C10 alkenyl groups substituted with one or more halogens; C2 to C10 ynynyl groups substituted with one or more halogens; C3 to C20 cycloalkylene groups substituted with one or more halogens; C3 to C20 cycloalkenylene groups substituted with one or more halogens; C6 to C30 arylene groups substituted with one or more halogens; C2 to C30 heterocyclic alkylene groups substituted with one or more halogens; C2 to C30 heterocyclic alkenylene groups substituted with one or more halogens; C2 to C30 heteroarylene groups substituted with one or more halogens, or combinations thereof.

[0061] From R 3 To R 6 and L 2At least one of the selected components may be a halogen atom (F, Cl, Br, or I); a C1 to C10 alkyl group substituted with one or more halogens (e.g., one or more halogen atoms); a C2 to C10 alkenyl group substituted with one or more halogens; a C2 to C10 alkynyl group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C2 to C30 heterocyclic alkyl group substituted with one or more halogens; a C2 to C30 heterocyclic alkenyl group substituted with one or more halogens; or a C6 to C30 aryl group substituted with one or more halogens. Substituted C2 to C30 heteroaryl groups; C1 to C10 alkylene groups substituted with one or more halogens; C2 to C10 alkenyl groups substituted with one or more halogens; C2 to C10 ynylene groups substituted with one or more halogens; C3 to C20 cycloalkylene groups substituted with one or more halogens; C3 to C20 cycloalkenylene groups substituted with one or more halogens; C6 to C30 aryl groups substituted with one or more halogens; C2 to C30 heterocyclic alkylene groups substituted with one or more halogens; C2 to C30 heterocyclic alkenylene groups substituted with one or more halogens; C2 to C30 heteroarylene groups substituted with one or more halogens, or combinations thereof, and

[0062] n1 can be 0 or 1.

[0063] As examples, sulfonic acid compounds containing (or including) one or more halogen elements (e.g., one or more halogen atoms) and sulfonamide compounds containing (or including) one or more halogen elements (e.g., one or more halogen atoms) may be substituted with at least one of fluorine (F), bromine (Br) and / or chlorine (Cl).

[0064] For example, in chemical formula 1,

[0065] R 1 It may be hydrogen, fluorine, bromine, chlorine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0066] R 2 It can be hydroxyl, amino, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C20 aryloxy, substituted or unsubstituted C1 to C10 alkylamino, or substituted or unsubstituted C6 to C20 aromaticamino.

[0067] L 1It may be a single bond (e.g., a monocovalent bond), a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof, and

[0068] From R 1 R 2 and L 1 At least one of the selected components may be fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 arylene group substituted with one or more of fluorine, bromine, and chlorine; or a combination thereof.

[0069] For example, in chemical formula 2,

[0070] R 3 To R 6 Each of these can independently be hydrogen, a halogen atom (F, Cl, Br, or I), a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C2 to C10 alkenyl, a substituted or unsubstituted C2 to C10 alkynyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C3 to C20 cycloalkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic alkyl, a substituted or unsubstituted C2 to C30 heterocyclic alkenyl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof.

[0071] R 3 To R 6 They can be independently connected or coupled (e.g., covalently connected or coupled) to form or provide substituted or unsubstituted C5 to C20 heterocyclic alkyl groups.

[0072] L 2It may be a single bond (e.g., a monocovalent bond), a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 ynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkenylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and

[0073] From R 3 To R 6 and L 2 At least one of the selected components may be a halogen atom (F, Cl, Br, or I); a C1 to C10 alkyl group substituted with one or more halogens (e.g., one or more halogen atoms); a C2 to C10 alkenyl group substituted with one or more halogens; a C2 to C10 alkynyl group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C2 to C30 heterocyclic alkyl group substituted with one or more halogens; a C2 to C30 heterocyclic alkenyl group substituted with one or more halogens; or a C6 to C30 aryl group substituted with one or more halogens. Substituted C2 to C30 heteroaryl groups; C1 to C10 alkylene groups substituted with one or more halogens; C2 to C10 alkenyl groups substituted with one or more halogens; C2 to C10 alkyne groups substituted with one or more halogens; C3 to C20 cycloalkylene groups substituted with one or more halogens; C3 to C20 cycloalkenyl groups substituted with one or more halogens; C6 to C30 aryl groups substituted with one or more halogens; C2 to C30 heterocyclic alkylene groups substituted with one or more halogens; C2 to C30 heterocyclic alkenyl groups substituted with one or more halogens; C2 to C30 heteroaryl groups substituted with one or more halogens, or combinations thereof.

[0074] For example, in chemical formula 1,

[0075] From R 1 and L 1At least one of the selected components may be fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 arylene group substituted with one or more of fluorine, bromine, and chlorine; or a combination thereof.

[0076] For example, in chemical formula 2,

[0077] From R 3 and R 4 At least one of the selected components may be fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 arylene group substituted with one or more of fluorine, bromine, and chlorine; or a combination thereof.

[0078] For example, sulfonic acid compounds containing one or more halogen elements (e.g., one or more halogen atoms) and sulfonamide compounds containing one or more halogen elements (e.g., one or more halogen atoms) may be selected from the compounds listed in Group 1.

[0079] Group 1

[0080]

[0081] Based on 100 wt% of the semiconductor photoresist composition, the content of at least one selected from sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements may be from about 0.001 wt% to about 10 wt%.

[0082] For example, based on 100 wt% of a semiconductor photoresist composition, the content of at least one selected from sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements may be from about 0.01 wt% to about 10 wt%, from about 0.01 wt% to about 5 wt%, or from about 0.05 wt% to about 5 wt%.

[0083] Based on 100% by weight of the semiconductor photoresist composition, the content of the tin-containing organometallic compound may be from about 0.5 wt% to about 30 wt%.

[0084] The semiconductor photoresist composition according to one or more embodiments may include, within the above-mentioned content range, at least one selected from tin-containing organometallic compounds and sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements, thereby improving or enhancing the sensitivity of the photoresist.

[0085] The semiconductor photoresist composition according to one or more embodiments may include a tin-containing organometallic compound and at least one selected from sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements in a weight ratio of about 99:1 to about 80:20. For example, the semiconductor photoresist composition may include a tin-containing organometallic compound and at least one selected from sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements in a weight ratio of about 99:1 to about 85:15.

[0086] If (for example, when) the weight ratio of a tin-containing organometallic compound and at least one selected from a sulfonic acid compound containing one or more halogen elements and a sulfonamide compound containing one or more halogen elements satisfies the above range, a semiconductor photoresist composition with excellent or suitable sensitivity can be provided.

[0087] Tin-containing organometallic compounds may include organooxy groups and / or organocarbonyloxy groups.

[0088] Tin-containing organometallic compounds can be represented by chemical formula 3.

[0089] Chemical formula 3

[0090]

[0091] In chemical formula 3,

[0092] R 7 It 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, substituted or unsubstituted C7 to C30 aralkyl, and substituted or unsubstituted C1 to C20 alkoxy.

[0093] R 8 To R 10Each 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 C7 to C30 aralkyl, an alkoxy, or an aryloxy (-OR) group. b , where R b 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 a carboxyl group (-O(CO)R). c , where R c It can 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), alkylamide or dialkylamide (-NR) d R e , where R d and R e Each of these can be independently hydrogen, 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 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof), or an amide group (-NR). f (COR g ), where R f and R g 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), or an amidine (-NR) group. h C(NR i )R j , where R h 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), alkylthio or arylthio (-SR). k , where R kIt 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 a thiocarbonyl (-S(CO)R l , where R l It can 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

[0094] Selected from R 8 To R 10 At least one of them can be derived from alkoxy or aryloxy (-OR) b , where R b 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 a carboxyl group (-O(C=O)R). c , where R c It can 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), alkylamide or dialkylamide (-NR) d R e , where R d and R e Each of these can be independently hydrogen, 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 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof), or an amide group (-NR). f (C = OR g ), where R f and R g 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), or an amidine (-NR) group. h C(NR i )R j, where R h 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), alkylthio or arylthio (-SR). k , where R k 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) and a thiocarbonyl (-S(C=O)R l , where R l It can be selected from 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.

[0095] Selected from R 8 To R 10 At least one of them can be derived from alkoxy or aryloxy (-OR) b , where R b 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) and a carboxyl group (-O(C=O)R). c , where R c It can be selected from 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.

[0096] In one or more embodiments, the compound represented by Formula 3 may include -OR b and / or -OC(=O)R c As a ligand, the pattern formed or provided using a semiconductor photoresist composition containing the ligand can exhibit excellent or appropriate limiting resolution.

[0097] In one or more embodiments, -OR b and / or -OC(=O)Rc Ligands can determine (or can be used to regulate) the solubility of compounds represented by chemical formula 3 in solvents.

[0098] R 7 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 containing 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.

[0099] R b It can be a substituted or unsubstituted C1 to C8 alkyl, a substituted or unsubstituted C3 to C8 cycloalkyl, a substituted or unsubstituted C2 to C8 alkenyl, a substituted or unsubstituted C2 to C8 alkynyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and

[0100] R c It can 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.

[0101] R 7 It can be methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valerate, ethoxy, propoxy, or combinations thereof.

[0102] R b It can be ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylylyl, benzyl, or combinations thereof, and

[0103] R c It can be hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylylyl, benzyl, or a combination thereof.

[0104] In one or more embodiments, the tin-containing organometallic compound may be represented by chemical formula 4 or chemical formula 5.

[0105] Chemical Formula 4

[0106] R 11 z SnO (2-(z / 2)-(x / 2)) (OH) x

[0107] In Chemical Formula 4,

[0108] R 11 may be a C1 - C31 hydrocarbon group, 0 < z ≤ 2, and 0 < (z + x) ≤ 4;

[0109] Chemical Formula 5

[0110] R 12 n Sn m X l Y k

[0111] Wherein, in Chemical Formula 5,

[0112] R 12 may be a substituted or unsubstituted C1 - C20 alkyl group, a substituted or unsubstituted C3 - C20 cycloalkyl group, a substituted or unsubstituted C2 - C20 aliphatic unsaturated organic group containing one or more double bonds or triple bonds, a substituted or unsubstituted C6 - C30 aryl group, a substituted or unsubstituted C4 - C30 heteroaryl group, a carbonyl group, an epoxyethyl group, an epoxypropyl group, or a combination thereof,

[0113] X may be sulfur (S), selenium (Se), or tellurium (Te),

[0114] Y may be -OR m or -OC(=O)R n ,

[0115] Wherein R m may be a substituted or unsubstituted C1 - C20 alkyl group, a substituted or unsubstituted C3 - C20 cycloalkyl group, a substituted or unsubstituted C2 - C20 alkenyl group, a substituted or unsubstituted C2 - C20 alkynyl group, a substituted or unsubstituted C6 - C30 aryl group, or a combination thereof,

[0116] R n may be hydrogen, a substituted or unsubstituted C1 - C20 alkyl group, a substituted or unsubstituted C3 - C20 cycloalkyl group, a substituted or unsubstituted C2 - C20 alkenyl group, a substituted or unsubstituted C2 - C20 alkynyl group, a substituted or unsubstituted C6 - C30 aryl group, or a combination thereof, and

[0117] n, m, l, and k may each independently be an integer from 1 to 20.

[0118] The solvent in the semiconductor photoresist composition according to one or more embodiments may be an organic solvent, such as an aromatic compound (e.g., xylene, toluene and / or the like), an alcohol (e.g., 4-methyl-2-pentanol, 4-methyl-2-propanol, 1-butanol, methanol, isopropanol, 1-propanol and / or the like), an ether (e.g., anisole, tetrahydrofuran and / or the like), an ester (n-butyl acetate, propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate and / or the like), a ketone (e.g., methyl ethyl ketone, 2-heptanone and / or the like), or a mixture thereof, but the embodiments of this disclosure are not limited thereto.

[0119] In addition to the tin-containing organometallic compound, at least one sulfonic acid compound containing one or more halogens, and sulfonamide compounds containing one or more halogens, and the solvent, the semiconductor photoresist composition according to one or more embodiments may further include a resin.

[0120] The resin may be a phenolic resin comprising at least one aromatic moiety selected from Group 2.

[0121] Group 2

[0122]

[0123] The resin can have a weight-average molecular weight (M0.05) of about 500 g / mol to about 20,000 g / mol. w ).

[0124] Based on the total amount of the semiconductor photoresist composition (e.g., 100 wt% of the semiconductor photoresist composition), the content of the resin can be from about 0.1 wt% to about 50 wt%.

[0125] If (for example, when) resin is included in the above-described content range, patterns formed or provided using a semiconductor photoresist composition according to one or more embodiments may have excellent or suitable etch resistance and / or heat resistance.

[0126] In one or more embodiments, the semiconductor photoresist composition according to one or more embodiments may consist of (or may include) a tin-containing organometallic compound as described in one or more embodiments, at least one sulfonic acid compound containing one or more halogen elements and a sulfonamide compound containing one or more halogen elements, a solvent, and a resin.

[0127] In one or more embodiments, the semiconductor photoresist composition according to one or more embodiments may further include additives as needed or desired. Examples of additives may be surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof.

[0128] Surfactants may include, for example, alkylbenzene sulfonates, alkylpyridinium salts, polyethylene glycol, quaternary ammonium salts, or combinations thereof, but the embodiments disclosed herein are not limited thereto.

[0129] The crosslinking agent can be, for example, a melamine crosslinking agent, a substituted urea crosslinking agent, an acrylic crosslinking agent, an epoxy crosslinking agent, and / or a polymer crosslinking agent, but the embodiments of this disclosure are not limited thereto. It can be a crosslinking agent having at least two substituents that form crosslinks, such as methoxymethylated glyoxal urea, butoxymethylated glyoxal urea, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, 4-hydroxybutyl acrylate, acrylic acid, urethane acrylate, methyl acrylate, 1,4-butanediol diglycidyl ether, glycidyl, 1,2-cyclohexanedicarboxylic acid diglycidyl ether, trimethylolpropane triglycidyl ether, 1,3-bis(glycidoxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, and / or the like.

[0130] Leveling agents can be used to improve or enhance the smoothness of coatings during the printing process, and can be commercially available or generally available.

[0131] Organic acids may include p-toluenesulfonic acid, benzenesulfonic acid, p-dodecylbenzenesulfonic acid, 1,4-naphthalenedisulfonic acid, methanesulfonic acid, sulfonium fluoride salts, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or combinations thereof, but the embodiments disclosed herein are not limited thereto.

[0132] The quencher can be diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or a combination thereof.

[0133] In one or more embodiments, the semiconductor photoresist composition may include an acidic compound different from at least one sulfonic acid compound selected from one or more halogen-containing compounds and sulfonamide compounds containing one or more halogen-containing elements. The miscible acidic compound may be an organic acid, phosphonic acid, and / or the like, for example, phosphonic acid.

[0134] The amount of additives used can be appropriately controlled or adjusted according to the desired performance.

[0135] In one or more embodiments, the semiconductor photoresist composition may further include a silane coupling agent as an adhesion enhancer to improve or enhance the tightness of contact with the substrate (e.g., to improve or enhance the adhesion of the semiconductor photoresist composition to the substrate). The silane coupling agent may be, for example, a silane compound containing carbon-carbon unsaturated bonds, such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri(β-methoxyethoxy)silane; and / or 3-methacryloyloxypropyltrimethoxysilane, 3-acryloyloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloyloxypropylmethyldimethoxysilane, 3-methacryloyloxypropylmethyldiethoxysilane; trimethoxy[3-(phenylamino)propyl]silane and / or the like, but the embodiments of this disclosure are not limited thereto.

[0136] Semiconductor photoresist compositions can form or provide patterns with high aspect ratios and without collapse. In one or more embodiments, to form or provide fine patterns with widths (e.g., linewidths) 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, the semiconductor photoresist composition can be used in photolithography processes using light in the 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. In one or more embodiments, the semiconductor photoresist composition according to one or more embodiments can be used to implement or provide extreme ultraviolet lithography using an EUV light source with a wavelength of about 13.5 nanometers.

[0137] According to one or more embodiments, a method is provided for forming or providing a pattern using a semiconductor photoresist composition as described in one or more embodiments. For example, the pattern produced may be a photoresist pattern.

[0138] A method of forming or providing a pattern according to one or more embodiments may include forming or providing an etch target layer on a substrate, coating a semiconductor photoresist composition on the etch target layer to form or provide a photoresist film, patterning the photoresist film to form or provide a photoresist pattern, and using the photoresist pattern as an etch mask to etch the etch target layer.

[0139] The following is for reference Figures 1A-1E Describes a method for forming or providing patterns using a semiconductor photoresist composition. Figures 1A-1E Each of these is a cross-sectional view illustrating a method of forming or providing a pattern using a semiconductor photoresist composition according to one or more embodiments.

[0140] Reference Figure 1A A target for etching (e.g., an etching target layer or an etching target layer) can be prepared. The target for etching can be a thin film 102 that can be formed or provided on the semiconductor substrate 100. Hereinafter, the target for etching can be defined as the thin film 102. The surface of the thin film 102 can be cleaned to remove impurities and / or similar substances remaining thereon. The thin film 102 can be, for example, a silicon nitride layer, a polysilicon layer, and / or a silicon oxide layer.

[0141] Subsequently, the resist underlay composition forming or providing the resist underlay 104 can be spin-coated onto the surface of the cleaned film 102. However, embodiments of this disclosure are not limited thereto, and one or more suitable coating methods may be used, such as spraying, dip coating, blade coating, printing methods such as inkjet printing and / or screen printing, and / or similar methods.

[0142] The coating process for the resist underlayer may not be provided; the following description includes the process for coating the resist underlayer.

[0143] The coated composition can then be dried and baked to form or provide a resist underlayer 104 on the film 102. Baking (e.g., heat treatment) can be performed at a temperature of about 100°C to about 500°C, for example, about 100°C to about 300°C.

[0144] A resist underlayer 104 may be formed or provided between the substrate 100 and the photoresist film 106, thereby preventing or reducing the non-uniformity (e.g., substantial non-uniformity) of the photoresist linewidth and patterning capability when light reflected from the interface or hard mask between the substrate 100 and the photoresist film 106 is scattered into unintended photoresist areas (e.g., when).

[0145] Reference Figure 1B A photoresist film 106 can be formed or provided by coating a semiconductor photoresist composition onto a resist substrate 104. The photoresist film 106 can be obtained or provided by coating a semiconductor photoresist composition according to one or more embodiments onto a thin film 102 formed or provided on a substrate 100, and then curing it by heat treatment.

[0146] For example, forming a pattern using a semiconductor photoresist composition may include coating a semiconductor resist composition on a substrate 100 having a thin film 102 by spin coating, slot coating, inkjet printing and / or similar methods, and then drying it to form or provide a photoresist film 106.

[0147] The semiconductor photoresist composition has already been described in detail and will not be repeated here.

[0148] Subsequently, the substrate 100 having the photoresist film 106 can undergo a first baking process (e.g., heat treatment). The first baking process can be performed at a temperature of about 80°C to about 120°C.

[0149] Reference Figure 1C A patterned mask 110 can be used to selectively expose the photoresist film 106.

[0150] For example, exposure can use light or beams with high-energy wavelengths (such as EUV (extreme ultraviolet; wavelength about 13.5 nm), electron beams (E-Beam) and / or similar light) and activating radiation with short wavelengths (such as i-line (wavelength about 365 nm), KrF excimer laser (wavelength about 248 nm), ArF excimer laser (wavelength about 193 nm) and / or similar light).

[0151] For example, the light or beam used for exposure according to one or more embodiments may have short wavelengths and high-energy wavelengths in the range of about 5 nanometers to about 150 nanometers, such as EUV (extreme ultraviolet; wavelength 13.5 nanometers), E-Beam (electron beam), and / or similar light.

[0152] The exposed region 106b of the photoresist film 106 can form a polymer by utilizing a cross-linking reaction (e.g., a condensation reaction between organometallic compounds), thereby having a different solubility than the unexposed region 106a of the photoresist film 106.

[0153] Subsequently, the substrate 100 may undergo a second baking process (e.g., heat treatment). The second baking process may be performed at a temperature of about 90°C to about 200°C. Due to the second baking process, the exposed area 106a of the photoresist film 106 may become easily insoluble in the developer.

[0154] exist Figure 1D In this process, light can be used to dissolve and remove the unexposed areas 106a of the photoresist film to form or provide a photoresist pattern 108. For example, the unexposed areas 106a of the photoresist film can be dissolved and removed using an organic solvent (such as 2-heptanone and / or similar substances) to complete the photoresist pattern 108 corresponding to a negative image.

[0155] According to one or more embodiments, the developing solution used in the method of forming or providing a pattern according to one or more embodiments may be an organic solvent. The organic solvent used in the method of forming or providing a pattern according to one or more embodiments may be, for example, ketones such as methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone and / or the like; alcohols such as 4-methyl-2-propanol, 1-butanol, isopropanol, 1-propanol, methanol and / or the like; esters such as propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate, n-butyl acetate, butyrolactone and / or the like; aromatic compounds such as benzene, xylene, toluene and / or the like, or combinations thereof.

[0156] However, the photoresist pattern according to one or more embodiments is not limited to a negative image, but can be formed or provided as a positive image. Here, the developer used to form or provide a positive image can be a quaternary ammonium hydroxide composition, such as tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, or a combination thereof.

[0157] According to one or more embodiments, exposure to light or beams of equal energy (such as extreme ultraviolet (EUV; wavelength of 13.5 nm), E-beams (electron beams), and / or similar light) and light of short wavelengths (such as i-lines (wavelength of approximately 365 nm), KrF excimer lasers (wavelength of approximately 248 nm), ArF excimer lasers (wavelength of approximately 193 nm), and / or similar light) 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 with a thickness 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.

[0158] In one or more embodiments, the photoresist pattern 108 may have a pitch of less than or equal to about 50 nanometers (e.g., 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 may have a linewidth roughness of less than or equal to about 10 nanometers, or 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.

[0159] Subsequently, the photoresist pattern 108 can be used as an etching mask to etch the resist substrate 104. Through this etching process, an organic thin film pattern 112 can be formed or provided. The organic thin film pattern 112 may also have a width (e.g., linewidth) corresponding to the photoresist pattern 108.

[0160] Reference Figure 1EBy using the photoresist pattern 108 as an etching mask, the exposed thin film 102 can be etched. As a result, the thin film can be formed or provided as a thin film pattern 114.

[0161] The etching of the thin film 102 can be, for example, dry etching using an etching gas, which can be, for example, CHF3, CF4, Cl2, BCl3 and mixtures thereof.

[0162] In the exposure process, the thin film pattern 114 formed or provided using the photoresist pattern 108 formed or provided by the exposure process performed using an EUV light source can have a width (e.g., linewidth) corresponding to the photoresist pattern 108. For example, the thin film pattern 114 can have a width (e.g., linewidth) of about 5 nanometers to about 100 nanometers, which may be equal to the width of the photoresist pattern 108. For example, the thin film pattern 114 formed or provided using the photoresist pattern 108 formed or provided by the exposure process performed using an EUV light source can have a width (e.g., linewidth) of about 5 nanometers to about 90 nanometers, about 5 nanometers to about 80 nanometers, about 5 nanometers to about 70 nanometers, about 5 nanometers to about 60 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, for example, a width (e.g., linewidth) less than or equal to about 20 nanometers, similar to or analogous to the width of the photoresist pattern 108.

[0163] The subject matter of this disclosure will now be described in more detail through examples of the preparation of semiconductor photoresist compositions described in one or more embodiments of this disclosure. However, the one or more embodiments of this disclosure are not technically limited to the examples described below.

[0164] Synthesis of organometallic compounds

[0165] Synthesis Example 1

[0166] Add 40.7 g of tert-butyltriphenyltin (t-butylSnPh3) and 300 g of propionic acid to a 250 mL double-necked round-bottom flask, and then heat under reflux for 24 hours.

[0167] By removing unreacted propionic acid under reduced pressure, the resulting compound represented by chemical formula 7 was obtained.

[0168] Chemical Formula 7

[0169]

[0170] Synthesis Example 2

[0171] 30 mL of anhydrous pentane was added to 10 g of tert-amyltin trichloride (t-AmylSnCl3), and the temperature was maintained at 0 °C. 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. After the reaction was complete, the product was filtered, concentrated, and dried under vacuum to obtain the compound represented by chemical formula 8.

[0172] Chemical Formula 8

[0173]

[0174] Synthesis Example 3

[0175] 10 g of dibutyltin dichloride was dissolved in 30 mL of diethyl 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 chemical formula 9, with a weight-average molecular weight (Mw) of 1,500 g / mol.

[0176] Chemical formula 9

[0177]

[0178] Preparation of semiconductor photoresist compositions

[0179] Examples 1 to 19 and Comparative Examples 1 to 6

[0180] The compounds represented by chemical formulas 7 to 9 obtained in Synthetic Examples 1 to 3, and at least one sulfonic acid compound containing one or more halogen elements and / or sulfonamide compound containing one or more halogen elements, as shown in Table 1, were dissolved at a concentration of 3% by weight in a mixed solution of propylene glycol monomethyl ether acetate (PGMEA) and propylene glycol methyl ether (PGME) (weight ratio 7:3), and filtered through a 0.1-micron polytetrafluoroethylene (PTFE) syringe filter to prepare a semiconductor photoresist composition.

[0181]

[0182] Table 1

[0183]

[0184] Evaluation 1: Sensitivity Evaluation

[0185] Each semiconductor photoresist composition according to the examples and comparative examples was spin-coated for 30 seconds at 1500 rpm on a 200 mm circular silicon wafer with hexamethyldisilazane (HMDS) deposited on its surface, and then baked at 90°C for 60 seconds. After coating, baking (post-coating baking, PAB) was performed, followed by placement at room temperature (23±2°C) for 30 seconds.

[0186] Next, extreme ultraviolet (EUV) light (Lawrence Berkeley National Laboratory Micro Exposure Tool, MET) was used to project a linear array of 50 circular pads, each 500 micrometers in diameter, onto a wafer coated with a photoresist composition. Here, the pad exposure time was adjusted to ensure that an increased dose of EUV light was applied to each pad.

[0187] Then, after exposure, the resist and substrate are baked on a hot plate at 160°C for 120 seconds. The baked film is then developed with propylene glycol monomethyl ether acetate (PGMEA) solvent to form or provide a negative image. Finally, the resulting film is baked again on a hot plate at 150°C for 2 minutes to complete the process.

[0188] The remaining resist thickness of the exposed pads was measured using an ellipsometry. For each exposure, the remaining thickness was measured and plotted as a function of the exposure amount. Dg (energy level at development completion) was measured for each type of resist. Sensitivity was evaluated according to the following criteria, and the results are shown in Table 2.

[0189] Sensitivity evaluation criteria

[0190] -A:Dg is less than 16 millijoules / cm² 2

[0191] -B:Dg is greater than or equal to 16 mJ / cm² 2

[0192] Evaluation 2: Evaluation of surface roughness

[0193] The surface of the films fabricated on circular silicon wafers using the above-described coating method according to the examples and comparative examples was confirmed by atomic force microscopy (AFM). The root-mean-squared roughness value (Rq) of 10 μm × 10 μm was calculated and evaluated according to the following criteria, and the results are shown in Table 2.

[0194] Surface roughness evaluation standard

[0195] -○: Less than or equal to 0.5 nanometers

[0196] -△: Greater than 0.5 nanometers and less than or equal to 0.7 nanometers

[0197] -X: greater than 0.7 nanometers

[0198] Table 2

[0199] Sensitivity Surface roughness Example 1 A ○ Example 2 A ○ Example 3 A ○ Example 4 A ○ Example 5 A ○ Example 6 A ○ Example 7 A △ Example 8 A △ Example 9 A ○ Example 10 A ○ Example 11 A ○ Example 12 A ○ Example 13 A ○ Example 14 A ○ Example 15 A ○ Example 16 A ○ Example 17 A ○ Example 18 A ○ Example 19 A ○ Comparative Example 1 B △ Comparative Example 2 B △ Comparative Example 3 B △ Comparative Example 4 B △ Comparative Example 5 B △ Comparative Example 6 B △

[0200] As can be seen from the results in Table 2, the patterns formed or provided using the semiconductor photoresist compositions of Examples 1 to 19 exhibit superior sensitivity and surface roughness characteristics compared to Comparative Examples 1 to 6.

[0201] Prior to this, certain embodiments of the present disclosure have been described and illustrated. However, it should be apparent to those skilled in the art that the present disclosure is not limited to the described embodiments, and appropriate modifications and transformations can be made without departing from the spirit and scope of the present disclosure. Therefore, such modified or transformed embodiments may not be understood separately from the technical ideas and aspects of one or more embodiments of the present disclosure, and the modified embodiments may be within the scope of the appended claims and their equivalents.

Claims

1. A semiconductor photoresist composition, comprising: Tin-containing organometallic compounds; It is selected from at least one of sulfonic acid compounds containing one or more halogen elements and sulfonamide compounds containing one or more halogen elements; as well as Solvent.

2. The semiconductor photoresist composition according to claim 1, wherein: The at least one of the sulfonic acid compounds containing one or more halogen elements and the sulfonamide compounds containing one or more halogen elements is represented by chemical formula 1 or chemical formula 2: Chemical Formula 1 Chemical formula 2 Among them, in chemical formula 1 and chemical formula 2, R 1 and R 3 To R 6 Each of the following is independently hydrogen, a halogen atom, a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C2 to C10 alkenyl, a substituted or unsubstituted C2 to C10 alkynyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C3 to C20 cycloalkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic alkyl, a substituted or unsubstituted C2 to C30 heterocyclic alkenyl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof. R 3 To R 6 They are independently interconnected to form substituted or unsubstituted C5 to C20 heterocyclic alkyl groups. R 2 It can be hydroxyl, amino, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryloxy, substituted or unsubstituted C1 to C20 alkylamino, or substituted or unsubstituted C6 to C20 aromaticamino. L 1 and L 2 Each of these can be independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 ynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkylene group, a substituted or unsubstituted C2 to C30 heterocyclic alkenyl group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof. Selected from R 1 R 2 and L 1 At least one of the following is a halogen atom; a C1 to C10 alkyl group substituted with one or more halogens; a C2 to C10 alkenyl group substituted with one or more halogens; a C2 to C10 alkynyl group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C2 to C30 heterocyclic alkyl group substituted with one or more halogens; a C2 to C30 heterocyclic alkenyl group substituted with one or more halogens; a C2 to C30 heteroaryl group substituted with one or more halogens; a C1 to C20 alkoxy group substituted with one or more halogens; a C6 to C20 aryloxy group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl ... One or more halogen-substituted C1 to C20 alkylamino groups; one or more halogen-substituted C6 to C20 arylamino groups; one or more halogen-substituted C1 to C10 alkylene groups; one or more halogen-substituted C2 to C10 alkenylene groups; one or more halogen-substituted C2 to C10 ynynylene groups; one or more halogen-substituted C3 to C20 cycloalkylene groups; one or more halogen-substituted C3 to C20 cycloalkenylene groups; one or more halogen-substituted C6 to C30 arylene groups; one or more halogen-substituted C2 to C30 heterocyclic alkylene groups; one or more halogen-substituted C2 to C30 heterocyclic alkenylene groups; one or more halogen-substituted C2 to C30 heteroarylene groups; or combinations thereof. Selected from R 3 To R 6 and L 2 At least one of the following is a halogen atom; a C1 to C10 alkyl group substituted with one or more halogens; a C2 to C10 alkenyl group substituted with one or more halogens; a C2 to C10 alkynyl group substituted with one or more halogens; a C3 to C20 cycloalkyl group substituted with one or more halogens; a C3 to C20 cycloalkenyl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C2 to C30 heterocyclic alkyl group substituted with one or more halogens; a C2 to C30 heterocyclic alkenyl group substituted with one or more halogens; a C2 to C30 heteroaryl group substituted with one or more halogens; a C6 to C30 aryl group substituted with one or more halogens; a C6 to C30 heterocyclic alkyl group substituted with one or more halogens; a C6 to C30 heteroaryl group substituted with one or more halogens; a C6 to C30 heteroaryl group substituted with one or more halogens; a C6 to C30 heterocyclic alkyl ... One or more halogen-substituted C1 to C10 alkylene groups; one or more halogen-substituted C2 to C10 alkenyl groups; one or more halogen-substituted C2 to C10 ynylene groups; one or more halogen-substituted C3 to C20 cycloalkylene groups; one or more halogen-substituted C3 to C20 cycloalkenyl groups; one or more halogen-substituted C6 to C30 arylene groups; one or more halogen-substituted C2 to C30 heterocyclic alkylene groups; one or more halogen-substituted C2 to C30 heterocyclic alkenyl groups; one or more halogen-substituted C2 to C30 heteroarylene groups, or combinations thereof, and n1 is either 0 or 1.

3. The semiconductor photoresist composition according to claim 2, wherein: R 1 and R 3 To R 6 Each of the following is independently hydrogen, fluorine, bromine, chlorine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof. R 3 To R 6 They are independently interconnected to form substituted or unsubstituted C5 to C20 heterocyclic alkyl groups. R 2 It can be hydroxyl, amino, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C20 aryloxy, substituted or unsubstituted C1 to C10 alkylamino, or substituted or unsubstituted C6 to C20 aromaticamino. L 1 and L 2 Each of the following is independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof. Selected from R 1 R 2 and L 1 At least one of them is fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine, or a combination thereof, and Selected from R 3 To R 6 and L 2 At least one of them is fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 arylene group substituted with one or more of fluorine, bromine, and chlorine, or a combination thereof.

4. The semiconductor photoresist composition according to claim 1, wherein: Selected from R 1 and L 1 At least one of them is fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine, or a combination thereof, and Selected from R 3 and R 4 At least one of them is fluorine; bromine; chlorine; a C1 to C10 alkyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkenyl group substituted with one or more of fluorine, bromine, and chlorine; a C2 to C10 alkynyl group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C20 cycloalkyl group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 aryl group substituted with one or more of fluorine, bromine, and chlorine; a C1 to C10 alkylene group substituted with one or more of fluorine, bromine, and chlorine; a C3 to C10 cycloalkylene group substituted with one or more of fluorine, bromine, and chlorine; a C6 to C20 arylene group substituted with one or more of fluorine, bromine, and chlorine, or a combination thereof.

5. The semiconductor photoresist composition according to claim 1, wherein: The at least one selected from the sulfonic acid compounds containing one or more halogen elements and the sulfonamide compounds containing one or more halogen elements is one of the compounds listed in Group 1: Group 1 6. The semiconductor photoresist composition according to claim 1, wherein: Based on 100% by weight of the semiconductor photoresist composition, the content of at least one selected from the sulfonic acid compound containing one or more halogen elements and the sulfonamide compound containing one or more halogen elements is from 0.001% by weight to 10% by weight.

7. The semiconductor photoresist composition according to claim 1, wherein: Based on 100% by weight of the semiconductor photoresist composition, the content of at least one selected from the sulfonic acid compound containing one or more halogen elements and the sulfonamide compound containing one or more halogen elements is from 0.05% by weight to 5% by weight.

8. The semiconductor photoresist composition according to claim 1, wherein: Based on 100% by weight of the semiconductor photoresist composition, the content of the tin-containing organometallic compound is from 0.5% by weight to 30% by weight.

9. The semiconductor photoresist composition according to claim 1, wherein: The weight ratio of the tin-containing organometallic compound and at least one selected from the sulfonic acid compound containing one or more halogen elements and the sulfonamide compound containing one or more halogen elements is from 99:1 to 80:

20.

10. The semiconductor photoresist composition according to claim 1, wherein: The semiconductor photoresist composition further includes surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof as additives.

11. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound includes at least one selected from organooxy groups and organocarbonyloxy groups.

12. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound is represented by chemical formula 3: Chemical formula 3 In chemical formula 3, R 7 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, substituted or unsubstituted C7 to C30 aralkyl, and substituted or unsubstituted C1 to C20 alkoxy. R 8 To R 10 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 C7 to C30 aralkyl; or derived from -OR b The alkoxy or aryloxy group represents R. b 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; derived from -O(CO)R c The carboxyl group represents R. c 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; derived from -NR d R e The alkylamide group or dialkylamide group represents R. d and R e Each 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; and is composed of -NR f (COR g ) represents an amide group, where R f and R g Each 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; and is composed of -NR h C(NR i )R j The amidine group is represented by R. h R i and R j Each 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; derived from -SR k The alkylthio or arylthio group represents R. k 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 derived from -S(CO)R. l The thiocarbonyl group represents R. l 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 Selected from R 8 To R 10 At least one of them is by -OR b The alkoxy or aryloxy group represents R. b 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; derived from -O(C=O)R c The carboxyl group represents R. c 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; derived from -NR d R e The alkylamide group or dialkylamide group represents R. d and R e Each 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; and is composed of -NR f (C = OR g ) represents an amide group, where R f and R g Each 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; and is composed of -NR h C(NR i )R j The amidine group is represented by R. h R i and R j Each 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; derived from -SR k The alkylthio or arylthio group represents R. k It refers to 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, and is derived from -S(C=O)R. l The thiocarbonyl group represents R. l 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.

13. The semiconductor photoresist composition according to claim 12, wherein: Selected from R 8 To R 10 At least one of the options is OR b The alkoxy or aryloxy group represents R. b 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 derived from -O(C=O)R c The carboxyl group represents R. c 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.

14. The semiconductor photoresist composition according to claim 13, wherein: R 7 The substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C6 to C20 aralkyl, ethoxy, propoxy, or combinations thereof. R b It is a substituted or unsubstituted C1 to C8 alkyl, a substituted or unsubstituted C3 to C8 cycloalkyl, a substituted or unsubstituted C2 to C8 alkenyl, a substituted or unsubstituted C2 to C8 alkynyl, a substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and R c 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.

15. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound is represented by chemical formula 4 or chemical formula 5: Chemical Formula 4 R 11 z SnO (2-(z / 2)-(x / 2)) (OH) x In chemical formula 4, R 11 is a C1 to C31 hydrocarbon group, 0 < z ≤ 2, and 0 < (z + x) ≤ 4; Chemical formula 5 R 12 n Sn m X l Y k In chemical formula 5, R 12 The following are 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 containing 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 is sulfur, selenium, or tellurium, and Y is -OR m or -OC(=O)R n , Where R m 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. R n 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 n, m, l, and k are each an independent integer from 1 to 20.

16. A method for forming a pattern, comprising: An etching target layer is set on the substrate; The semiconductor photoresist composition as described in any one of claims 1 to 15 is coated on the etched target layer to form a photoresist film; The photoresist film is patterned to set a photoresist pattern; as well as The photoresist pattern is used as an etching mask to etch the target layer.

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