Composition for semiconductor photoresist and method for forming patterns using the same

Abstract

To provide a semiconductor photoresist composition which exhibits little change in a pattern line width corresponding to a nitrogen oxide concentration, few particle defects, and improved sensitivity, and a pattern forming method using the same.SOLUTION: The present invention relates to: a semiconductor photoresist composition which contains an Sn-containing organometallic compound, a compound containing at least two ketone groups, an aromatic ring compound substituted with at least one of OH, SH and NR13R14 (R13 and R14 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group), and a solvent; and a pattern forming method using the semiconductor photoresist composition.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This description relates to a semiconductor photoresist composition and a pattern formation method using the same. [Background technology]

[0002] EUV (extreme ultraviolet) lithography is attracting attention as one of the key technologies for manufacturing next-generation semiconductor devices. EUV lithography is a pattern formation technique that uses EUV light with a wavelength of 13.5 nm as the exposure light source. EUV lithography has been demonstrated to be able to form extremely fine patterns (for example, less than 20 nm) in the exposure process of semiconductor device manufacturing.

[0003] The realization of extreme ultraviolet (EUV) lithography requires the development of compatible photoresists that can achieve spatial resolutions of 16 nm or less. Currently, traditional chemically amplified (CA) photoresists are striving to meet the specifications for resolution, photospeed, feature roughness, and line edge roughness (LER) for next-generation devices.

[0004] The intrinsic image blur caused by acid-catalyzed reactions in these polymer-type photoresists limits resolution at small feature sizes, a phenomenon long known in electron beam lithography. Chemically amplified (CA) photoresists, while designed for high sensitivity, can be partially more challenging under EUV exposure because their typical elemental makeup reduces the photoresist's absorbance at a wavelength of 13.5 nm, resulting in reduced sensitivity.

[0005] CA photoresists can suffer from roughness issues at small feature sizes, and experiments have shown that line edge roughness (LER) increases as the photospeed decreases, partly due to the nature of the acid-catalyzed process. Due to the shortcomings and problems of CA photoresists, the semiconductor industry is seeking new types of high-performance photoresists.

[0006] To overcome the shortcomings of the chemically amplified organic photosensitive compositions described above, inorganic photosensitive compositions have been studied. Inorganic photosensitive compositions are mainly used for negative tone patterning, where chemical modification via a non-chemical amplification mechanism is required to prevent removal by developer compositions. Because inorganic compositions contain inorganic elements that have a higher EUV absorption rate compared to hydrocarbons, sensitivity can be ensured even with a non-chemical amplification mechanism, and they are not sensitive to the stochastic effect, resulting in less line edge roughness and fewer defects.

[0007] Inorganic photoresists based on tungsten and peroxopolyacids of tungsten mixed with niobium, titanium, and / or tantalum have been reported for use as radiation-sensitive materials for patterning (US5061599; H. Okamoto, T. Iwayanagi, K. Mochiji, H. Umezaki, T. Kudo, Applied Physics Letters, 49(5), 298-300, 1986).

[0008] These materials have been effective in patterning large features in bilayer configurations as deep UV, X-ray, and electron beam sources. More recently, impressive performance has been demonstrated when using cationic hafnium metal oxide sulfate (HfSOx) materials with peroxo complexing agents to image 15 nm half-pitch (HP) by projection EUV lithography (US2011-0045406; JKStowers, A. Telecky, M. Kocsis, BL Clark, DAKEszler, A. Grenville, CN Anderson, PPNaulleau, Proc. SPIE, 7969, 796915, 2011). This system exhibits the best performance of non-CA photoresists and has a light speed that approaches the requirements for a viable EUV photoresist. However, hafnium metal oxide sulfate materials containing peroxo-complexing agents have several practical drawbacks. Firstly, these materials are coated with a highly corrosive sulfuric acid / hydrogen peroxide mixture, resulting in poor shelf-life stability. Secondly, structural modifications to improve performance are not easy as a composite mixture. Thirdly, they must be developed with extremely high concentrations of TMAH (tetramethylammonium hydroxide) solution, such as 25 wt%.

[0009] In recent years, molecules containing tin have been found to exhibit excellent absorption of extreme ultraviolet light, and active research is being conducted on them. In the case of organotin polymers, one such example, alkyl ligands dissociate due to light absorption or the secondary electrons generated by it, and crosslinking via oxo bonds with surrounding chains enables negative tone patterning that is not removed by organic developers. Such organotin polymers have shown a dramatic improvement in sensitivity while maintaining resolution and line edge roughness, but further improvement of the aforementioned patterning properties is necessary for commercialization. [Overview of the project] [Problems that the invention aims to solve]

[0010] One example provides a semiconductor photoresist composition that exhibits improved sensitivity due to reduced pattern line width variation and particle defects in response to nitrogen oxide concentration.

[0011] Another embodiment provides a pattern formation method using the aforementioned semiconductor photoresist composition.

[0012] One example of a semiconductor photoresist composition includes: a Sn-containing organometallic compound; a compound containing at least two ketone groups; OH, SH, and NR 13 R 14 (R 13 and R 14 Each of these independently comprises a hydrogen atom, an aromatic ring compound substituted with at least one of a substituted or unsubstituted C1-C10 alkyl group or a C6-C20 aryl group, and a solvent.

[0013] Other examples of pattern formation methods include the steps of forming an etching target film on a substrate, applying the aforementioned semiconductor photoresist composition on the etching target film to form a photoresist film, patterning the photoresist film to form a photoresist pattern, and using the photoresist pattern as an etching mask to etch the etching target film.

[0014] One example of a semiconductor photoresist composition exhibits reduced pattern line width variation and particle defects in response to nitrogen oxide concentration, resulting in improved sensitivity and the realization of sharper patterns. [Brief explanation of the drawing]

[0015] [Figure 1] This is a cross-sectional view illustrating a pattern formation method using a semiconductor photoresist composition as an example. [Modes for carrying out the invention]

[0016] The embodiments of the present invention will be described in detail below with reference to the attached drawings. However, in order to clarify the gist of this description, explanations of already known functions or configurations will be omitted.

[0017] To ensure clarity in this description, irrelevant details have been omitted, and the same or similar urea components are given the same reference numerals throughout the specification. Furthermore, the dimensions and thicknesses of each component shown in the drawings are provided arbitrarily for illustrative purposes, and this description is not necessarily limited to those depicted.

[0018] In the drawings, the thickness is shown enlarged to clearly represent multiple layers and regions. Also, for ease of explanation, the thickness of some layers and regions is exaggerated in the drawings. When a layer, film, region, plate, or other part is "on top of" or "on" another part, this includes not only when it is "directly on top" of another part, but also when another part is in between.

[0019] From this description, "substituted" means that the hydrogen atom is replaced by deuterium, a halogen group, a hydroxyl group, a carboxyl group, a thiol group, a cyano group, a nitro group, -NRR' (where R and R' are independently hydrogen, a substituted or unsubstituted C1-C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3-C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6-C30 aromatic hydrocarbon group), -SiRR'R'' (where R, R', and R'' are independently This means that the hydrogen atom is substituted with hydrogen, a substituted or unsubstituted C1-C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3-C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6-C30 aromatic hydrocarbon group, a C1-C30 alkyl group, a C1-C10 haloalkyl group, a C1-C10 alkylsilyl group, a C3-C30 cycloalkyl group, a C6-C30 aryl group, a C1-C20 alkoxy group, a C1-C20 sulfide group, or a combination thereof. "Unsubstituted" means that the hydrogen atom is not substituted with another substituent and remains a hydrogen atom.

[0020] In this specification, "alkyl (alkyl) group" means a linear or branched aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a "saturated alkyl group" that does not have any double or triple bonds.

[0021] The alkyl group may be a C1-C8 alkyl group. For example, the alkyl group may be a C1-C7 alkyl group, a C1-C6 alkyl group, or a C1-C5 alkyl group. For example, the C1-C5 alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group or a 2,2-dimethylpropyl group.

[0022] In this document, unless otherwise defined, "cycloalkyl group" refers to a monovalent cyclic aliphatic saturated hydrocarbon group.

[0023] The cycloalkyl group may be a C3-C8 cycloalkyl group, for example, a C3-C7 cycloalkyl group, a C3-C6 cycloalkyl group, a C3-C5 cycloalkyl group, or a C3-C4 cycloalkyl group. For example, the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and is not limited to these.

[0024] In this specification, "aliphatic unsaturated organic group" means a hydrocarbon group in which the bonds between carbon atoms in the molecule are double bonds, triple bonds, or combinations thereof.

[0025] The aliphatic unsaturated organic group may be a C2-C8 aliphatic unsaturated organic group. For example, the aliphatic unsaturated organic group may be a C2-C7 aliphatic unsaturated organic group, a C2-C6 aliphatic unsaturated organic group, a C2-C5 aliphatic unsaturated organic group, or a C2-C4 aliphatic unsaturated organic group. For example, the C2-C4 aliphatic unsaturated organic group may be a vinyl group, an ethynyl group, an aryl group, a 1-propenyl group, a 1-methyl-1-propenyl group, a 2-propenyl group, a 2-methyl-2-propenyl group, a 1-propanyl group, a 1-methyl-1-propanyl group, a 2-propanyl group, a 2-methyl-2-propanyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group.

[0026] In this specification, "aryl group" means a substituent in which all elements of the cyclic substituent have p-orbitals and these p-orbitals form a conjugation, and includes monocyclic or fusion-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0027] As used herein, the term "heteroaryl group" means that within an aryl group, it contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups can be directly linked via a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings can be fused to each other. When the heteroaryl group is a fused ring, each ring can contain 1 to 3 of the heteroatoms.

[0028] As used herein, the term "alkenyl group" means, unless otherwise defined, a straight-chain or branched-chain aliphatic hydrocarbon group, an aliphatic unsaturated alkenyl group containing one or more double bonds.

[0029] As used herein, the term "alkynyl group" means, unless otherwise defined, a straight-chain or branched-chain aliphatic hydrocarbon group, an aliphatic unsaturated alkynyl group containing one or more triple bonds.

[0030] Hereinafter, a composition for a semiconductor photoresist according to an embodiment will be described.

[0031] A composition for a semiconductor photoresist according to an embodiment of the present invention can include a Sn-containing organometallic compound; a compound containing at least two ketone groups; an aromatic ring compound substituted with at least one of OH, SH, and NR 13 R 14 [[ID=2)), where R 13 and R 14 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl group or a C6-C20 aryl group), and a solvent.

[0032] In the composition for a semiconductor photoresist, the rate of line width change can be minimized by the action of the compound containing at least two ketone groups as a scavenger. Together with this, OH, SH, and NR 13 R14 (R 13 and R 14 Each of these compounds independently contains an aromatic ring compound substituted with at least one of the following: hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group. Solvent stabilization improves defect, sensitivity, and LER, resulting in superior resolution.

[0033] As an example, the aromatic ring compound and the compound containing at least two ketone groups are present in a weight ratio of 1:1 to 1:10.

[0034] As a specific example, the aromatic ring compound:the compound containing at least two ketone groups is included in a weight ratio of 1:1 to 1:10, 1:2 to 1:10, or 1:2 to 1:9.

[0035] The compound containing at least two ketone groups is represented by the following chemical formula 1 or chemical formula 2. [ka] [ka] In the aforementioned chemical formula 1 and chemical formula 2, R 1 ~R 6 Each of these is independently hydrogen, a halogen, 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. L 1 ~L 3 Each of these is independently a single bond, a carbonyl group, a substituted or unsubstituted C1-C20 alkylene group, or a combination thereof. n1 and n2 are each independently one of the integers between 0 and 2. n1 + n2 is greater than or equal to 1.

[0036] As an example, the aromatic ring compound is OH, SH, and NR 13 R 14 A phenyl group substituted with at least one of the following: OH, SH, and NR 13 R 14 A naphthyl group substituted with at least one of the following: OH, SH, and NR 13 R 14 An anthracenyl group substituted with at least one of the following: OH, SH, and NR 13 R 14 A phenanthrene group substituted with at least one of the following; or OH, SH, and NR 13 R 14 A triphenylene group substituted with at least one of the following: R 13 and R 14 Each of these may independently be hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

[0037] For example, the aromatic ring compound is OH, SH, and NR 13 R 14 (R 13 and R 14 Each of these may be independently substituted with at least two of the following: hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

[0038] In one embodiment, the aromatic ring compound may be substituted with at least two OH groups.

[0039] In another embodiment, the aromatic ring compound may be substituted with at least two SH groups.

[0040] In another embodiment, the aromatic ring compound comprises at least two NRs. 13 R 14 (R 13 and R 14Each of these may be independently substituted with hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

[0041] For example, the compound containing at least two ketone groups may be at least one selected from pentane-2,4-dione, 2,3-butanedione, 3-methyl-2,4-pentanedione, and 2,2,6,6-tetramethyl-3,5-heptanedione.

[0042] For example, the aromatic ring compound may be at least one selected from 1,4-hydroquinone, 1,2-benzenediol, 1,3-benzenediol, benzene-1,2-dithiol, 1,4-phenylenediamine, 4-aminobenzene-1-thiol, 3-aminobenzene-1-thiol, and 2-aminobenzene-1-thiol.

[0043] The compound containing at least two ketone groups and the aromatic ring compound may be present in an amount of 0.001 to 10% by weight relative to 100% by weight of the semiconductor photoresist composition.

[0044] For example, the compound containing at least two ketone groups and the aromatic ring compound may be present in amounts of 0.005 to 10% by weight, 0.01 to 10% by weight, or 0.1 to 5% by weight, based on 100% by weight of the semiconductor photoresist composition.

[0045] The aforementioned Sn-containing organometallic compound may be present in an amount of 0.5 to 30% by weight relative to 100% by weight of the semiconductor photoresist composition.

[0046] A semiconductor photoresist composition according to one embodiment contains the Sn-containing organometallic compound, the compound containing at least two ketone groups, and the aromatic ring compound within the specified content range, thereby improving the sensitivity and solubility of the photoresist and reducing the rate of linewidth change in response to atmospheric conditions.

[0047] A semiconductor photoresist composition according to one embodiment may contain the Sn-containing organometallic compound, the compound containing at least two ketone groups, and the aromatic ring compound in a weight ratio of 90:10 to 50:50. For example, a semiconductor photoresist composition may contain the Sn-containing organometallic compound, the compound containing at least two ketone groups, and the aromatic ring compound in a weight ratio of 90:10 to 60:40.

[0048] When the weight ratio of the Sn-containing organometallic compound, the compound containing at least two ketone groups, and the aromatic ring compound satisfies the aforementioned range, a semiconductor photoresist composition with excellent sensitivity can be provided. The Sn-containing organometallic compound may contain at least one of an organooxy group and an organocarbonyloxy group.

[0049] The aforementioned organometallic compound is represented by the following chemical formula 3. [ka] In the aforementioned chemical formula 3, R 7 These are selected from substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C7-C30 groups. R 8 ~R 10 These are, independently, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C7-C30 arylalkyl groups, alkoxy and aryloxy (-OR) groups. a , here, R a(which are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof), carboxyl groups (-O(C=O)R b , R b (which is 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), alkylamide or dialkylamide (-NR c R d , here, R c and R d Each of these is independently 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), amidato (-NR e (C=OR f ), here, R e and R f Each of these is independently 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), amidinato (-NR) g C(NR h )R i , here, R g , R h and R iEach of these is independently 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), alkylthio and arylthio (-SR) j , here, R j (which is 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) or a thiocarboxyl group (-S(C=O)R k , R k (These are hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof.) R 8 ~R 10 At least one of them is an alkoxy and an aryloxy (-OR a , here, R a (which are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof), carboxyl groups (-O(C=O)R b , R b (which is 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), alkylamide or dialkylamide (-NR c R d , here, R c and R dEach of these is independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, or an 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), amidato (-NR e (C=OR f ), here, R e and R f Each of these is independently 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), amidinato (-NR) g C(NR h )R i , here, R g , R h and R i Each of these is independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a combination thereof), alkylthio and arylthio (-SR) j , here, R j (which are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof) and thiocarboxyl groups (-S(C=O)R k , R k The group is selected from hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or a combination thereof.

[0050] Said R 8 ~R 10 At least one of them is alkoxy and aryloxy (-OR a , where R a is 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 a carboxyl group (-O(C=O)R b , R b is 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).

[0051] On the other hand, the compound represented by Chemical Formula 4 can exhibit excellent limit resolution in a pattern formed using a semiconductor photoresist composition containing it by including -OR a or -OC(=O)R b .

[0052] Also, the ligand of -OR a or -OC(=O)R b can determine the solubility of the compound represented by Chemical Formula 4 in a solvent.

[0053] Said R 7 is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C3-C8 cycloalkyl group, a substituted or unsubstituted C2-C8 aliphatic unsaturated organic group containing one or more double bonds or triple bonds, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C4-C20 heteroaryl group, a carbonyl group, an ethoxy group, a propoxy group, or a combination thereof, R aThese are substituted or unsubstituted C1-C8 alkyl groups, substituted or unsubstituted C3-C8 cycloalkyl groups, substituted or unsubstituted C2-C8 alkenyl groups, substituted or unsubstituted C2-C8 alkynyl groups, substituted or unsubstituted C6-C20 aryl groups, or combinations thereof. R b This may be hydrogen, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C3-C8 cycloalkyl group, a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted C2-C8 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, or a combination thereof.

[0054] The aforementioned R 7 These are methyl group, ethyl group, propyl group, butyl group, isopropyl group, tert-butyl group, 2,2-dimethylpropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, ethenyl group, propenyl group, butenyl group, ethynyl group, propynyl group, butynyl group, phenyl group, tolyl group, xylene group, benzyl group, formyl group, acetyl group, propanoyl group, butanoyl group, pentanoyl group, ethoxy group, propoxy group, or combinations thereof. R a These are ethyl group, propyl group, butyl group, isopropyl group, tert-butyl group, 2,2-dimethylpropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, ethenyl group, propenyl group, butenyl group, ethynyl group, propynyl group, butynyl group, phenyl group, tolyl group, xylene group, benzyl group, or combinations thereof. R b This may be hydrogen, ethyl group, propyl group, butyl group, isopropyl group, tert-butyl group, 2,2-dimethylpropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, ethenyl group, propenyl group, butenyl group, ethynyl group, propynyl group, butynyl group, phenyl group, tolyl group, xylene group, benzyl group, or a combination thereof.

[0055] Furthermore, the Sn-containing organometallic compound is represented by the following chemical formula 4 or chemical formula 5. [ka] In the aforementioned chemical formula 4, R 11 This is the C1-C31 hydrocarbyl group, where 0 <z≦2であり、0<(z+x)≦4であり; [ka] In the aforementioned chemical formula 5, R 12 These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 aliphatic unsaturated organic groups containing one or more double or triple bonds, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C4-C30 heteroaryl groups, carbonyl groups, ethylene oxide groups, propylene oxide groups, or combinations thereof. X is sulfur (S), selenium (Se), or tellurium (Te). Y is -OR l Or -OC(=O)R m And, The aforementioned R l These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof. R m This includes hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof. The aforementioned a1, b1, c1, and d1 are each independent integers between 1 and 20.

[0056] The solvent contained in the semiconductor photoresist composition according to one embodiment may be an organic solvent and may include, but is not limited to, aromatic compounds (e.g., xylene, toluene), alcohols (e.g., 4-methyl-2-pentanol, 4-methyl-2-propanol, 1-butanol, methanol, isopropyl alcohol, 1-propanol), ethers (e.g., anisole, tetrahydrofuran), esters (n-butylacetic acid, propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactic acid), ketones (e.g., methyl ethyl ketone, 2-heptanone), and mixtures thereof.

[0057] One example of a semiconductor resist composition includes the Sn-containing organometallic compound, a compound containing at least two ketone groups, OH, SH, and NR 1 (R 1 In addition to hydrogen, an aromatic ring compound substituted with at least one of a substituted or unsubstituted C1-C10 alkyl group or C6-C20 aryl group, and a solvent, the mixture may further contain a resin.

[0058] The aforementioned resin may be a phenolic resin containing at least one of the aromatic moistures listed in Group 1 below. [ka] The resin may have a weight-average molecular weight of 500 to 20,000.

[0059] The resin may be present in an amount of 0.1% to 50% by weight relative to the total content of the semiconductor photoresist composition.

[0060] When the aforementioned resin is included within the aforementioned content range, it can have excellent etching resistance and heat resistance.

[0061] On the other hand, the semiconductor photoresist composition includes the aforementioned Sn-containing organometallic compound, a compound containing at least two ketone groups, OH, SH, and NR.1 (R 1 The preferred component consists of a hydrogen atom, an aromatic ring compound substituted with at least one of a substituted or unsubstituted C1-C10 alkyl group or a C6-C20 aryl group, a solvent, and a resin.

[0062] The semiconductor photoresist compositions described in the above-mentioned examples may further contain additives. Examples of such additives include surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof.

[0063] The surfactant may be, but is not limited to, alkylbenzene sulfonates, alkylpyridinium salts, polyethylene glycol, quaternary ammonium salts, or combinations thereof.

[0064] Examples of crosslinking agents include, but are not limited to, melamine-based crosslinking agents, substituted urea-based crosslinking agents, acrylic-based crosslinking agents, epoxy-based crosslinking agents, or polymer-based crosslinking agents. Examples of crosslinking agents having at least two crosslinking substituents include compounds such as methoxymethylated glycolyl, butoxymethylated glycolyl, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, 4-hydroxybutyl acrylate, acrylic acid, urethane acrylate, acrylic methacrylate, 1,4-butanediol diglycidyl ether, glycidol, diglycidyl 1,2-cyclohexaneticlevoxylate, trimethylpropane triglycidyl ether, 1,3-bis(glycidoxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, or methoxymethylated thiourea.

[0065] Leveling agents are used to improve coating flatness during printing, and commercially available, known leveling agents can be used.

[0066] The organic acid may be, but is not limited to, p-toluenesulfonic acid, benzenesulfonic acid, p-dodecylbenzenesulfonic acid, 1,4-naphthalenedisulfonic acid, methanesulfonic acid, fluorinated sulfonates, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or a combination thereof.

[0067] The quencher may be diphenyl(p-toluyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or a combination thereof.

[0068] The amount of these additives used can be easily adjusted according to the desired physical properties, and they may even be omitted.

[0069] Furthermore, the semiconductor photoresist composition may use a silane coupling agent as an additive to improve adhesion to the substrate (for example, to improve the adhesion strength of the semiconductor photoresist composition to the substrate). The silane coupling agent may be, but is not limited to, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris(β-methoxyethoxy)silane; or 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane; or carbon-carbon unsaturated bond-containing silane compounds such as trimethoxy[3-(phenylamino)propyl]silane.

[0070] The semiconductor photoresist composition may not exhibit pattern distortion even when forming patterns with a high aspect ratio. Therefore, it can be used in photoresist processes using light with wavelengths of 5 nm to 150 nm, such as photoresist processes using light with wavelengths of 5 nm to 100 nm, such as photoresist processes using light with wavelengths of 5 nm to 100 nm, such as photoresist processes using light with wavelengths of 5 nm to 80 nm, such as photoresist processes using light with wavelengths of 5 nm to 50 nm, such as photoresist processes using light with wavelengths of 5 nm to 30 nm, and photoresist processes using light with wavelengths of 5 nm to 20 nm, in order to form fine patterns with widths of 5 nm to 100 nm, such as fine patterns with widths of 5 nm to 80 nm, such as fine patterns with widths of 5 nm to 70 nm, such fine patterns with widths of 5 nm to 50 nm, such fine patterns with widths of 5 nm to 40 nm, such fine patterns with widths of 5 nm to 30 nm, and photoresist processes using light with wavelengths of 5 nm to 20 nm. Therefore, by using the semiconductor photoresist composition according to one embodiment, it is possible to realize extreme ultraviolet lithography using an EUV light source with a wavelength of approximately 13.5 nm.

[0071] On the other hand, according to another embodiment, a method for forming a pattern using the above-described semiconductor photoresist composition can be provided. For example, the manufactured pattern may be a photoresist pattern.

[0072] One example of a pattern formation method includes the steps of forming an etching target film on a substrate, applying the aforementioned semiconductor photoresist composition on the etching target film to form a photoresist film, patterning the photoresist film to form a photoresist pattern, and etching the etching target film using the photoresist pattern as an etching mask.

[0073] The method for forming a pattern using the semiconductor photoresist composition described above will be explained below with reference to Figure 1. Figure 1 is a cross-sectional view illustrating the pattern formation method using the semiconductor photoresist composition according to the present invention.

[0074] Referring to Figure 1(a), the system includes a priority etching target. An example of the etching target may be a thin film 102 formed on a semiconductor substrate 100. The following description will only cover the case where the etching target is a thin film 102. The surface of the thin film 102 is cleaned to remove any contaminants remaining on the thin film 102. The thin film 102 may be, for example, a silicon nitride film, a polysilicon film, or a silicon oxide film.

[0075] Next, a resist underlayer forming composition for forming a resist underlayer 104 on the surface of the cleaned thin film 102 is coated using a spin coating method. However, this example is not necessarily limited to this, and various known coating methods, such as spray coating, dip coating, knife-edge coating, and printing methods, such as inkjet printing and screen printing, can also be used.

[0076] The above-mentioned resist underlayer coating process can be omitted, and the following will describe the case where the resist underlayer is coated.

[0077] Subsequently, a drying and baking process is performed to form a resist underlayer film 104 on the thin film 102. The baking process is carried out at approximately 100 to 500°C, for example, at approximately 100°C to 300°C.

[0078] The resist underlayer 104 is formed between the substrate 100 and the photoresist film 106. This prevents the scattering of irradiation lines reflected from the interface between the substrate 100 and the photoresist film 106 or from the interlayer hard mask into unintended photoresist regions, thereby preventing non-uniformity of the photoresist linewidth and interference with pattern formation.

[0079] Referring to Figure 1(b), the above-mentioned semiconductor photoresist composition is coated onto the resist underlayer film 104 to form a photoresist film 106. The photoresist film 106 may also be formed by coating the above-mentioned semiconductor photoresist composition onto a thin film 102 formed on the substrate 100 and then curing it through a heat treatment process.

[0080] More specifically, the step of forming a pattern using a semiconductor photoresist composition may include a process of applying the above-described semiconductor photoresist composition onto a substrate 100 on which a thin film 102 is formed by spin coating, slit coating, inkjet printing, etc., and a process of drying the applied semiconductor photoresist composition to form a photoresist film 106.

[0081] Since the compositions for semiconductor photoresists have already been explained in detail, we will omit further explanation.

[0082] Next, a first baking process is performed to heat the substrate 100 on which the photoresist film 106 is formed. The first baking process can be carried out at a temperature of approximately 80°C to approximately 120°C.

[0083] Referring to Figure 1(c), the photoresist film 106 is selectively exposed using a patterned mask 110.

[0084] As an example, examples of light that can be used in the exposure process include not only short-wavelength light such as the activation irradiation wire i-line (wavelength 365 nm), KrF excimer laser (wavelength 248 nm), and ArF excimer laser (wavelength 193 nm), but also high-energy wavelength light such as EUV (Extreme ultraviolet; wavelength 13.5 nm) and E-Beam (electron beam).

[0085] More specifically, the exposure light in one embodiment may be short-wavelength light having a wavelength range of 5 nm to 150 nm, or it may be light having a high-energy wavelength such as EUV (Extreme ultraviolet; wavelength 13.5 nm) or E-Beam (electron beam).

[0086] In the photoresist film 106, the exposed region 106b forms a polymer through crosslinking reactions such as condensation between organometallic compounds, thereby acquiring a different solubility from the unexposed region 106a of the photoresist film 106.

[0087] Next, a second baking process is performed on the substrate 100. The second baking process can be carried out at a temperature of approximately 90°C to approximately 200°C. By performing the second baking process, the exposed region 106b of the photoresist film 106 becomes difficult to dissolve in the developer.

[0088] Figure 1(d) shows a photoresist pattern 108 formed by dissolving and removing the photoresist film 106a corresponding to the unexposed region using a developer. Specifically, the photoresist pattern 108 corresponding to the negative tone image is completed by dissolving and then removing the photoresist film 106a corresponding to the unexposed region using an organic solvent such as 2-heptanone.

[0089] As mentioned above, the developing solution used in the pattern formation method described in one example can be an organic solvent.

[0090] Examples of organic solvents used in the pattern formation method according to one embodiment include ketones such as methyl ethyl ketone, acetone, cyclohexanone, and 2-heptanone; alcohols such as 4-methyl-2-propanol, 1-butanol, isopropanol, 1-propanol, and methanol; esters such as propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactic acid, n-butylacetic acid, and butyrolactone; aromatic compounds such as benzene, xylene, and toluene; or combinations thereof.

[0091] However, the photoresist pattern in one embodiment is not necessarily limited to being formed as a negative tone image; it can also be formed to have a positive tone image. In this case, examples of developers that can be used to form a positive tone image include quaternary ammonium hydroxide compositions such as tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, or combinations thereof.

[0092] As mentioned above, the photoresist pattern 108 formed by exposure with light having wavelengths such as i-line (wavelength 365nm), KrF excimer laser (wavelength 248nm), and ArF excimer laser (wavelength 193nm), as well as high-energy light such as EUV (Extreme ultraviolet; wavelength 13.5nm) and E-Beam (electron beam), can have a width of thickness from 5nm to 100nm. For example, the photoresist pattern 108 can be formed with a thickness of 5nm to 90nm, 5nm to 80nm, 5nm to 70nm, 5nm to 60nm, 5nm to 50nm, 5nm to 40nm, 5nm to 30nm, and 5nm to 20nm.

[0093] On the other hand, the photoresist pattern 108 can have a half-pitch of about 50 nm or less, for example, 40 nm or less, for example, 30 nm or less, for example, 20 nm or less, for example, 15 nm or less, and a pitch having a line width roughness of about 10 nm or less, about 5 nm or less, about 3 nm or less, or about 2 nm or less.

[0094] Next, the photoresist pattern 108 is used as an etching mask to etch the resist underlayer film 104. This etching process forms an organic film pattern 112. The formed organic film pattern 112 can have a width corresponding to the photoresist pattern 108.

[0095] Referring to Figure 1(e), the photoresist pattern 108 is applied as an etching mask to etch the exposed thin film 102. As a result, the thin film is formed with the thin film pattern 114.

[0096] The thin film 102 can be etched, for example, by dry etching using an etching gas. The etching gas can be, for example, CHF3, CF4, Cl2, BCl3, or a mixture thereof.

[0097] In the previously performed exposure process, the thin film pattern 114 formed using the photoresist pattern 108 formed by the exposure process using an EUV light source can have a width corresponding to the photoresist pattern 108. For example, it can have a width of 5 nm to 100 nm, similar to the photoresist pattern 108. For instance, the thin film pattern 114 formed by the exposure process using an EUV light source can have widths of 5 nm to 90 nm, 5 nm to 80 nm, 5 nm to 70 nm, 5 nm to 60 nm, 5 nm to 50 nm, 5 nm to 40 nm, 5 nm to 30 nm, and 5 nm to 20 nm, similar to the photoresist pattern 108, and more specifically, it can be formed with a width of 20 nm or less. [Examples]

[0098] The present invention will be described in more detail below through the examples of the manufacturing of the semiconductor photoresist composition described above. However, the technical features of the present invention are not limited by the following examples.

[0099] Synthesis of organometallic compounds Synthesis Example 1 Add 30 ml of anhydrous pentane to 10 g of t-AmylSnCl3, maintain the temperature at 0°C, then add 7.4 g of diethylamine and 6.1 g of ethanol, and stir at room temperature for 1 hour. Once the reaction is complete, filter, concentrate, and vacuum dry to obtain the compound shown in chemical formula 6 below. [ka]

[0100] Synthesis Example 2 Place 340.7g of t-butylSnPh and 300g of propionic acid in a 250ml two-necked round-bottom flask and heat under reflux for 24 hours.

[0101] The unreacted propionic acid is removed under reduced pressure to obtain the compound represented by the following chemical formula 7. [ka]

[0102] Synthesis Example 3 After dissolving 10 g of dibutyltin dichloride in 30 mL of ether, 70 mL of 1 M sodium hydroxide (NaOH) aqueous solution is added and the mixture is stirred for 1 hour. After stirring, the resulting solid is filtered and washed three times with 25 mL of deionized water, and then dried under reduced pressure at 100°C to obtain an organometallic compound with a weight-average molecular weight of 1,500 represented by the following chemical formula 8. [ka]

[0103] (Manufacturing of semiconductor photoresist compositions) Examples 1-10 and Comparative Examples 1-7 The organometallic compounds represented by chemical formulas 6 to 8 and the additives obtained in Synthesis Examples 1 to 3 are dissolved in Propylene glycol methyl ether acetate (PGMEA) at a concentration of 3 wt% in the weight ratios listed in Table 1 below, and filtered through a 0.1 μm PTFE (polytetrafluoroethylene) syringe filter to produce a semiconductor photoresist composition.

[0104] [Table 1]

[0105] A1:1,4-Hyroquinone A2:1,2-Benzenediol A3:1,3-Benzenediol A4:Benzene-1,2-dithiol A5: 1,4-Phenylenediamine B1: Pentane-2,4-dione B2:2,3-Butanedione C1:1,4-Benzoquinone D1: Acetic Acid D2: 1-butanol D3: 2-Methyl-2-butanol

[0106] Evaluation 1: Sensitivity evaluation The photoresist compositions according to the above examples and comparative examples were spin-coated onto a 200 mm circular silicon wafer whose surface was deposited on HMDS at 1500 rpm for 30 seconds at room temperature (23±2°C), and then baked at 110°C for 60 seconds (post-apply bake, PAB).

[0107] Subsequently, EUV light was projected onto the wafer coated with the photoresist composition. The pad exposure time was adjusted so that the increasing EUV dose was applied to each pad.

[0108] Subsequently, the resist and markings were exposed to a hot plate at 170°C for 60 seconds and then fired. The fired film was developed in a developer containing PGMEA solvent to form a negative tone image. Finally, the process was completed by firing on a hot plate at 200°C for 60 seconds.

[0109] The residual resist thickness of exposed pads was measured using a polarization measurement method (Ellipsometer). The remaining thickness was measured for each exposure level and graphed as a function of the exposure level. Sensitivity was measured, and the results are shown in Table 2. The measurement error was ±2 mJ.

[0110] Rating 2: Resolution (CD) Rating After the process was completed, the pattern wafer had line / space and CD patterns formed on it. It was then transferred to a CD-SEM (GC-9380, Hitachi) to measure the CD (Critical Dimension) size at the 14nm half-pitch of the mask pattern. The minimum value of the space CD between lines was measured, and the CD increase rate, calculated using Equation 1 below, is shown in Table 2. The measurement error is ±1.0nm.

[0111] <Expression 1> ΔCD: NO in the atmosphere x When CD- is at high concentration, NO in the atmosphere x When the concentration is low, CD(nitrogen oxides (NO) x (Concentration range: High concentration is defined as atmospheric nitrogen oxide concentration > 0.015 ppm, and low concentration is defined as atmospheric nitrogen oxide concentration ≤ 0.015 ppm.)

[0112] Evaluation 3: Particle defect evaluation Particle defects in patterned wafers after process completion were analyzed using an inspertor system (KLA AIT-FUSION). Contaminating particles and defects on the patterned wafers were observed, classified, and analyzed using a scanning electron microscope. Particle defect control was managed by particle count, with an ND (Non-detectable) level indicating no observed effective contaminating particles.

[0113] [Table 2]

[0114] The results in Table 2 confirm that the patterns formed using the semiconductor photoresist compositions of Examples 1 to 10 exhibit superior sensitivity and LER compared to Comparative Examples 1 to 7, as well as superior resolution characteristics due to the absence of CD increase.

[0115] Although specific embodiments of the present invention have been described and illustrated above, it is obvious to those ordinary skill in the art that the present invention is not limited to the described embodiments, and that various modifications and variations are possible without departing from the spirit and scope of the invention. Therefore, such modifications or variations should not be understood individually from the technical spirit or viewpoint of the present invention, and the modified embodiments should be considered to fall within the scope of the claims of the present invention. [Explanation of symbols]

[0116] 100...Substrate, 102...Thin film, 104...Resist underlayer film, 106...Photoresist film, 106a...Unexposed region, 106b...Exposed region, 108...Photoresist pattern, 112...Organic film pattern, 110...Patterned mask, 114...Thin film pattern.

Claims

1. A Sn-containing organometallic compound comprising at least one of an organic oxy group and an organic carbonyl oxy group; Compounds comprising at least two ketone groups, represented by the following chemical formula 1 or chemical formula 2; OH, SH, and NR １３ R １４ (R １３ and R １４ Each of these is an aromatic ring compound independently substituted with at least one of hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group; and A composition for semiconductor photoresists, comprising a solvent. 【Chemistry 1】 【Chemistry 2】 In the aforementioned chemical formula 1 and chemical formula 2, R1 to R6 are each independently hydrogen, halogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof. L1 to L3 are each independently a single bond, a carbonyl group, a substituted or unsubstituted C1-C20 alkylene group, or a combination thereof. n1 and n2 are each independently one of the integers between 0 and 2. n1 + n2 is greater than or equal to 1.

2. The semiconductor photoresist composition according to claim 1, wherein the aromatic ring compound: the compound containing at least two ketone groups is included in a weight ratio of 1:1 to 1:

10.

3. The aromatic ring compound is a phenyl group substituted with at least one of OH, SH, and NR １３ R １４ ; a naphthyl group substituted with at least one of OH, SH, and NR １３ R １４ ; an anthracenyl group substituted with at least one of OH, SH, and NR １３ R １４ ; a phenanthrenyl group substituted with at least one of OH, SH, and NR １３ R １４ ; or a triphenylene group substituted with at least one of OH, SH, and NR １３ R １４ and R １３ and R １４ The semiconductor photoresist composition according to claim 1, wherein each of them is independently hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

4. The aromatic ring compound is OH, SH, and NR １３ R １４ (R １３ and R １４ The semiconductor photoresist composition according to claim 1, wherein each of the groups is independently substituted with at least two of the following: hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

5. The semiconductor photoresist composition according to claim 4, wherein the aromatic ring compound is substituted with at least two OH groups.

6. The semiconductor photoresist composition according to claim 4, wherein the aromatic ring compound is substituted with at least two SHs.

7. The aromatic ring compound comprises at least two NR １３ R １４ (R １３ and R １４ The semiconductor photoresist composition according to claim 4, wherein each of the elements is independently substituted with hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group.

8. The semiconductor photoresist composition according to claim 1, wherein the compound comprising at least two ketone groups is at least one selected from pentane-2,4-dione, 2,3-butanedione, 3-methyl-2,4-pentanedione, and 2,2,6,6-tetramethyl-3,5-heptanedione.

9. The semiconductor photoresist composition according to claim 1, wherein the aromatic ring compound is at least one selected from 1,4-hydroquinone, 1,2-benzenediol, 1,3-benzenediol, benzene-1,2-dithiol, 1,4-phenylenediamine, 4-aminobenzene-1-thiol, 3-aminobenzene-1-thiol, and 2-aminobenzene-1-thiol.

10. The semiconductor photoresist composition according to claim 1, wherein the compound containing at least two ketone groups and the aromatic ring compound are present in an amount of 0.001 to 10% by weight based on 100% by weight of the semiconductor photoresist composition.

11. The semiconductor photoresist composition according to claim 1, wherein the Sn-containing organometallic compound is present in an amount of 0.5 to 30% by weight based on 100% by weight of the semiconductor photoresist composition.

12. The semiconductor photoresist composition according to claim 1, wherein the Sn-containing organometallic compound, the compound containing at least two ketone groups, and the aromatic ring compound are present in a weight ratio of 90:10 to 50:

50.

13. The semiconductor photoresist composition according to claim 1, further comprising additives such as a surfactant, a crosslinking agent, a leveling agent, an organic acid, an inhibitor (quencher), or a combination thereof.

14. The Sn-containing organometallic compound is represented by the following chemical formula 3, and is the semiconductor photoresist composition according to claim 1: 【Transformation 3】 In the aforementioned chemical formula 3, R ７ These are selected from substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C7-C30 arylalkyl groups. R ８ ~R １０ Each of these independently comprises 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, a substituted or unsubstituted C7-C30 arylalkyl group, an alkoxy, and an aryloxy (-OR ａ Here, R ａ (These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof), carboxyl groups (-O(C=O)R ｂ , R ｂ (-NR) ｃ R ｄ Here, R ｃ and R ｄ Each of these is independently 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), amidato (-NR ｅ (C = OR ｆ ), here, R ｅ and R ｆ Each of these is independently 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), amidinato (-NR ｇ C (NR ｈ ) R ｉ Here, R ｇ , R ｈ and R ｉ Each of these is independently 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), alkylthio and arylthio (-SR ｊ Here, R ｊ (which is 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) or a thiocarboxyl group (-S(C=O)R ｋ , R ｋ (These are hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof.) R ８ ~R １０ At least one of them is an alkoxy and an aryloxy (-OR ａ Here, R ａ (These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof), carboxyl groups (-O(C=O)R ｂ , R ｂ (-NR) ｃ R ｄ Here, R ｃ and R ｄ Each is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or an 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), amidato (-NR ｅ (C = OR ｆ ), here, R ｅ and R ｆ Each of these is independently 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), amidinato (-NR ｇ C (NR ｈ ) R ｉ Here, R ｇ , R ｈ and R ｉ Each of these is independently 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), alkylthio and arylthio (-SR ｊ Here, R ｊ (which are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof) and thiocarboxyl groups (-S(C=O)R ｋ , R ｋ (is selected from hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or a combination thereof.)

15. The aforementioned R ８ ~R １０ At least one of them is an alkoxy and an aryloxy (-OR ａ Here, R ａ (which are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof), and carboxyl groups (-O(C=O)R ｂ , R ｂ The semiconductor photoresist composition according to claim 14, wherein is selected from 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.

16. The aforementioned R ７ These are substituted or unsubstituted C1-C8 alkyl groups, substituted or unsubstituted C3-C8 cycloalkyl groups, substituted or unsubstituted C2-C8 aliphatic unsaturated organic groups containing one or more double or triple bonds, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C4-C20 heteroaryl groups, carbonyl groups, ethoxy groups, propoxy groups, or combinations thereof. R ａ These are substituted or unsubstituted C1-C8 alkyl groups, substituted or unsubstituted C3-C8 cycloalkyl groups, substituted or unsubstituted C2-C8 alkenyl groups, substituted or unsubstituted C2-C8 alkynyl groups, substituted or unsubstituted C6-C20 aryl groups, or combinations thereof. R ｂ The semiconductor photoresist composition according to claim 14, wherein is hydrogen, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C3-C8 cycloalkyl group, a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted C2-C8 alkynyl group, a substituted or unsubstituted C6-C20 aryl group, or a combination thereof.

17. The Sn-containing organometallic compound is represented by the following chemical formula 4 or chemical formula 5, the semiconductor photoresist composition according to claim 1: 【Chemistry 4】 In the aforementioned chemical formula 4, R １１ These are the C1-C31 hydrocarbyl group, where 0 < z ≤ 2 and 0 < (z + x) ≤ 4; 【Transformation 5】 In the aforementioned chemical formula 5, R １２ These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 aliphatic unsaturated organic groups containing one or more double or triple bonds, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C4-C30 heteroaryl groups, carbonyl groups, ethylene oxide groups, propylene oxide groups, or combinations thereof. X is sulfur (S), selenium (Se), or tellurium (Te), Y is -OR ｌ or -OC(=O)R ｍ And, The aforementioned R ｌ These are substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof. R ｍ These are hydrogen, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 aryl groups, or combinations thereof. a1, b1, c1, and d1 are each independent integers between 1 and 20.

18. Steps include forming an etching target film on a substrate; A step of forming a photoresist film by applying the semiconductor photoresist composition according to any one of claims 1 to 17 onto the film to be etched; Steps of patterning the photoresist film to form a photoresist pattern; and A pattern formation method comprising the step of etching a film to be etched using the aforementioned photoresist pattern as an etching mask.

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