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

Abstract

This invention provides a semiconductor photoresist composition that can provide patterns with improved sensitivity and LER characteristics and superior resolution, as well as a pattern formation method using the semiconductor photoresist composition. [Solution] The present invention relates to a semiconductor photoresist composition comprising an organometallic compound; a cyclic diketone compound; and a solvent, and a pattern formation method utilizing the same.

Description

[Technical Field]

[0001] This document 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. It has been demonstrated that EUV lithography can 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 polymeric photoresists limits resolution at small feature sizes, which has long been known in e-beam lithography. Chemically amplified (CA) photoresists are designed for high sensitivity, but their typical elemental makeup reduces the absorbance of the photoresist at a wavelength of 13.5 nm, which can make them more challenging under EUV exposure, at least in part, as a result of reduced sensitivity.

[0005] Also, CA photoresists can be plagued by roughness issues at small feature sizes, and experimentally it has been shown that line edge roughness (LER) increases due to a decrease in photospeed, which is partly due to the nature of the acid-catalyzed process. Due to the drawbacks and problems of CA photoresists, there is a need for new types of high-performance photoresists in the semiconductor industry.

[0006] To overcome the disadvantages of the chemically amplified organic photosensitive composition described above, inorganic photosensitive compositions have been studied. In the case of inorganic photosensitive compositions, they are mainly used for negative tone patterning that is resistant to removal by a developer composition through chemical modification by a non-chemically amplified mechanism. In the case of inorganic compositions, they contain inorganic elements with a high EUV absorption rate compared to hydrocarbons, and it is known that they can ensure sensitivity even with a non-chemically amplified mechanism, are less susceptible to the stochastic effect, and have less 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, 495, 298-300, 1986).

[0008] These materials are deep UV, X-ray, and electron beam sources and have been effective for patterning large features in bilayer configurations. More recently, cationic hafnium metal oxide sulfate (HfSOx) materials have shown impressive performance when used with a peroxo complexing agent 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 demonstrates the best performance of non-CA photoresists and has a light speed close to 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 they are composite mixtures. Thirdly, they must be developed with extremely high concentrations of TMAH (tetramethylammonium hydroxide) solution, such as 25 wt%. [Overview of the Initiative] [Problems that the invention aims to solve]

[0009] Recently, tin-containing molecules have been found to exhibit excellent absorption of extreme ultraviolet light, and active research is underway. In the case of organotin polymers, one such example, the alkyl ligand dissociates due to light absorption or the secondary electrons generated by it, and crosslinking occurs through oxo bonding with surrounding chains, enabling negative tone patterning that is not removed by organic developers. While such organotin polymers have shown a dramatic improvement in sensitivity while maintaining resolution and line edge roughness, further improvements to the aforementioned patterning properties are necessary for commercialization. [Means for solving the problem]

[0010] One embodiment provides a semiconductor photoresist composition that can provide patterns with improved sensitivity and LER characteristics and excellent resolution.

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

[0012] A semiconductor photoresist composition according to one embodiment comprises an organometallic compound, a cyclic diketone compound, and a solvent.

[0013] A pattern formation method according to another embodiment 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 using the photoresist pattern as an etching mask to etch the etching target film.

[0014] In one embodiment, a semiconductor photoresist composition can improve sensitivity and LER characteristics to provide a photoresist pattern with excellent resolution. [Brief explanation of the drawing]

[0015] [Figure 1]This is a cross-sectional view illustrating a pattern formation method using a semiconductor photoresist composition according to one embodiment. [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, descriptions of functions or configurations that have already been made public will be omitted.

[0017] To clearly explain this description, unnecessary explanatory parts have been omitted, and the same or similar reference numerals are used throughout the specification for identical or similar components. Furthermore, the dimensions and thicknesses of each component shown in the drawings are arbitrarily provided for explanatory purposes and are not necessarily limited to those shown in this description.

[0018] To clearly represent the various layers and regions in the drawings, the thicknesses were enlarged. Furthermore, for explanatory purposes, the thicknesses of some layers and regions were exaggerated in the drawings. When a layer, film, region, plate, or other part is described as being "on top of" or "on" another part, this includes not only cases where it is "directly on top" of the other part, but also cases where there are other parts in between.

[0019] In 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 remains a hydrogen atom without being substituted by another substituent.

[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 contain 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 specified, "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, "aryl group" means a substituent in which all elements of the cyclic substituent have p-obitals, and these p-obitals form a conjugation, and includes monocyclic or fused polycyclic (i.e., rings sharing an adjacent pair of carbon atoms) functional groups.

[0025] In this specification, a "heteroaryl group" means an aryl group containing 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 by sigma bonds, or, if the heteroaryl group contains two or more rings, the two or more rings can be fused together. If the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0026] In this specification, unless otherwise defined, "alkenyl group" means a linear or branched aliphatic hydrocarbon group containing one or more double bonds, specifically an aliphatic unsaturated alkenyl group.

[0027] In this specification, unless otherwise defined, "alkynyl group" means a linear or branched aliphatic hydrocarbon group containing one or more triple bonds, specifically an aliphatic unsaturated alkynyl group.

[0028] A semiconductor photoresist composition according to one embodiment will be described below.

[0029] A semiconductor photoresist composition according to one embodiment of the present invention may contain an organometallic compound, a cyclic diketone compound, and a solvent.

[0030] The semiconductor photoresist composition according to the present invention is a composition comprising an organometallic compound, a cyclic diketone compound, and a solvent, wherein the inclusion of the cyclic diketone compound increases the sensitivity to extreme ultraviolet light and improves the pattern roughness of the pattern formed using it.

[0031] The aforementioned cyclic diketone compound is represented by the following chemical formula 1. [ka]

[0032] In the above chemical formula 1, Ring A is a substituted or unsubstituted C3-C20 non-aromatic carbon ring group.

[0033] In this specification, the C3-C20 non-aromatic carbocyclic group refers to a saturated or unsaturated cyclic group having 3 to 20 carbon atoms as ring-forming atoms. The C3-C20 non-aromatic carbocyclic group may be a monocyclic or polycyclic group.

[0034] As an example, the C3-C20 non-aromatic carbocyclic group may be a saturated cyclic group having 3 to 20 carbon atoms as ring-forming atoms, or an unsaturated cyclic group having 3 to 20 carbon atoms as ring-forming atoms and containing at least one unsaturated bond within the ring.

[0035] For example, the cyclic diketone compound may be substituted with one or more hydroxyl groups.

[0036] The aforementioned non-aromatic carbon ring group can be modified in various ways, such as being divalent, trivalent, or tetravalent, depending on the number of linked substituents.

[0037] The sensitivity is further improved if the ring contains at least one unsaturated bond or if one or more hydroxyl groups are substituted.

[0038] For example, ring A may be a substituted or unsubstituted cyclobutane group, a substituted or unsubstituted cyclopentane group, a substituted or unsubstituted cyclohexane group, a substituted or unsubstituted cycloheptane group, a substituted or unsubstituted cyclooctane group, a substituted or unsubstituted cyclobutene group, a substituted or unsubstituted cyclopentene group, a substituted or unsubstituted cyclohexene group, a substituted or unsubstituted cycloheptene group, a substituted or unsubstituted cyclooctene group, or a combination thereof.

[0039] In one specific example, the cyclic diketone compound is selected from the compounds listed in Group 1 below. [ka]

[0040] The cyclic diketone compound is included in an amount of 0.001 to 10% by weight relative to 100% by weight of the semiconductor photoresist composition.

[0041] For example, the cyclic diketone compound is included in an amount of 0.01 to 10% by weight, 0.02 to 10% by weight, 0.03 to 10% by weight, or 0.05 to 10% by weight per 100% by weight of the semiconductor photoresist composition.

[0042] The organometallic compound is included in an amount of 0.5% to 30% by weight relative to 100% by weight of the semiconductor photoresist composition.

[0043] A semiconductor photoresist composition according to one embodiment can improve the sensitivity of a photoresist by containing the cyclic diketone compound within the specified content range.

[0044] The organometallic compound may also be an organotin compound containing at least one of an organooxy group and an organocarbonyloxy group.

[0045] For example, the organometallic compound is represented by the following chemical formula 2.

Chemical formula

[0046] 0000242In the above chemical formula 2, R e , c , d , d , e is selected from 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, and a substituted or unsubstituted C7-C30 arylalkyl group. R 2 ~R 4 are each independently 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 C-2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C7-C30 arylalkyl group, alkoxy and aryloxy (-OR b , where R b 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), a carboxyl group (-O(CO)R c , R c 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), an alkylamide or dialkylamide (-NR d R e , where R d and R eEach 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 f (COR g ), here R f and R g 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) h C(NR i )R j Here, R h , R i and R j 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) k Here, R k (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(CO)R l , R l (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.) R2 ~R 4 At least one of them is an alkoxy and an aryloxy (-OR b Here, R b (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(CO)R c , R c (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 d R e Here, R d and R e Each 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 f (COR g ), here R f and R g 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 h , R i and R jEach 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) k Here, R k (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(CO)R l , R l (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).

[0047] The aforementioned R 2 ~R 4 At least one of them is an alkoxy and an aryloxy (-OR b Here, R b (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(CO)R c , R c (which may be 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.)

[0048] On the other hand, the compound represented by chemical formula 2 has -OR as a ligand. b Or -OC(=O)R c By including this, patterns formed using a semiconductor photoresist composition containing it can exhibit excellent limiting resolution.

[0049] Also, -OR b Or -OC(=O)R c The ligand can determine the solubility of the compound represented by chemical formula 2 in a solvent.

[0050] The aforementioned R 1 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 b 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 c 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.

[0051] The aforementioned R 1These 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, prophenyl 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 b 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, prophenyl group, butenyl group, ethynyl group, propynyl group, butynyl group, phenyl group, tolyl group, xylene group, benzyl group, or combinations thereof. R c 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, prophenyl group, butenyl group, ethynyl group, propynyl group, butynyl group, phenyl group, tolyl group, xylene group, benzyl group, or a combination thereof.

[0052] Furthermore, the organometallic compound is represented by the following chemical formula 3 or chemical formula 4. [ka] In the aforementioned chemical formula 3, R 5 This is a C1-C31 hydrocarbyl group, where 0 <z≦2であり、0<(z+x)≦4であり; [ka] In the aforementioned chemical formula 4, R 6These 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 m Or -OC(=O)R n And, The aforementioned R m 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 n 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 a, b, c, and d are each independent integers between 1 and 20.

[0053] 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-butyl acetate, propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate), ketones (e.g., methyl ethyl ketone, 2-heptanone), and mixtures thereof.

[0054] In addition to the organometallic compound, cyclic diketone compound, and solvent, the semiconductor resist composition according to one embodiment may further contain a resin.

[0055] The aforementioned resin may be a phenolic resin containing at least one of the aromatic molecules listed in Group 2 below.

[0056] [ka]

[0057] The resin may have a weight-average molecular weight of 500 to 20,000.

[0058] The resin is included in an amount of 0.1% to 50% by weight relative to the total content of the semiconductor photoresist composition.

[0059] When the resin is included within the aforementioned content range, it can have excellent etching resistance and heat resistance.

[0060] On the other hand, the semiconductor photoresist composition is preferably composed of the aforementioned organometallic compound, cyclic diketone compound, solvent, and resin.

[0061] The semiconductor photoresist composition according to the above-described embodiment may further contain additives. Examples of such additives include surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof.

[0062] The surfactant may be, but is not limited to, alkylbenzene sulfonates, alkylpyridinium salts, polyethylene glycol, quaternary ammonium salts, or combinations thereof.

[0063] 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-cyclohexane dicarboxylate, trimethylpropane triglycidyl ether, 1,3-bis(glycidoxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, or methoxymethylated thioelements.

[0064] Leveling agents are used to improve coating flatness during printing, and commercially available, known leveling agents can be used.

[0065] 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 sulfonium salts, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or a combination thereof.

[0066] The quencher may be diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or a combination thereof.

[0067] The amount of these additives used can be easily adjusted according to the desired physical properties, and they may even be omitted.

[0068] Furthermore, the semiconductor photoresist composition may be further enhanced with a silane coupling agent as an adhesion enhancer to improve adhesion to the substrate (for example, to improve the adhesion 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-acryloxpropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane; or carbon-carbon unsaturated bond-containing silane compounds such as trimethoxy[3-(phenylamino)propyl]silane.

[0069] 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, photoresist processes using light with wavelengths of 5 nm to 100 nm, photoresist processes using light with wavelengths of 5 nm to 80 nm, photoresist processes using light with wavelengths of 5 nm to 80 nm, photoresist processes using light with wavelengths of 5 nm to 50 nm, 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 to form fine patterns with widths of 5 nm to 100 nm, 5 nm to 80 nm, 5 nm to 50 nm, 5 nm to 40 nm, 5 nm to 30 nm, and 5 nm to 20 nm. Therefore, by using a semiconductor photoresist composition according to one embodiment, extreme ultraviolet lithography using an EUV light source with a wavelength of approximately 13.5 nm can be realized.

[0070] On the other hand, according to another embodiment, a method for forming a pattern using the semiconductor photoresist composition described above can be provided. For example, the manufactured pattern may be a photoresist pattern.

[0071] A pattern formation method according to one embodiment 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.

[0072] The following describes a method for forming a pattern using the semiconductor photoresist composition described above, with reference to Figure 1. Figure 1 is a cross-sectional view illustrating a pattern formation method using the semiconductor photoresist composition according to the present invention.

[0073] Referring to Figure 1(a), first, the object to be etched is prepared. An example of the object to be etched is a thin film 102 formed on a semiconductor substrate 100. The following explanation will only describe the case where the object to be etched is a thin film 102. To remove contaminants and other materials remaining on the thin film 102, the surface of the thin film 102 is cleaned. The thin film 102 may be, for example, a silicon nitride film, a polysilicon film, or a silicon oxide film.

[0074] Next, a resist underlayer forming composition for forming a resist underlayer 104 is coated onto the surface of the cleaned thin film 102 using a spin coating method. However, this embodiment 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.

[0075] The above-mentioned resist underlayer coating process may be omitted, and the case where the resist underlayer is coated will be described below.

[0076] Subsequently, drying and baking processes are 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.

[0077] The resist underlayer 104 is formed between the substrate 100 and the photoresist film 106, and can prevent non-uniformity of the photoresist linewidth and interference with pattern formation when irradiation lines reflected from the interface or interlayer hard mask between the substrate 100 and the photoresist film 106 are scattered into unintended photoresist areas.

[0078] 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.

[0079] More specifically, the step of forming a pattern using a semiconductor photoresist composition may include the steps 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 drying the applied semiconductor photoresist composition to form a photoresist film 106.

[0080] Since the compositions for semiconductor photoresists have already been explained in detail, I will omit any redundant explanations.

[0081] Next, a first baking step is performed in which the substrate 100 on which the photoresist film 106 is formed is heated. The first baking step can be performed at a temperature of approximately 80°C to approximately 120°C.

[0082] Referring to Figure 1(c), the photoresist film 106 is selectively exposed using a patterned mask 110.

[0083] As an example, examples of light that can be used in the exposure process include not only light with wavelengths such as the activation irradiation diagram i-line (wavelength 365 nm), KrF excimer laser (wavelength 248 nm), and ArF excimer laser (wavelength 193 nm), but also light with high energy wavelengths such as EUV (Extreme Ultra Violet; wavelength 13.5 nm) and E-Beam (electron beam).

[0084] More specifically, the exposure light according to one embodiment may be 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 Ultra Violet; wavelength 13.5 nm) or E-Beam (electron beam).

[0085] The exposed region 106b of the photoresist film 106 forms a polymer through crosslinking reactions such as condensation between organometallic compounds, thereby acquiring different solubility from the unexposed region 106a of the photoresist film 106.

[0086] Next, a second baking process is performed on the substrate 100. The second baking process can be performed 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 less soluble in the developer.

[0087] 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.

[0088] As mentioned above, the developer used in the pattern-forming method according to one embodiment may be an organic solvent. Examples of organic solvents used in the pattern-forming 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 lactate, n-butyl acetate, and butyrolactone; aromatic compounds such as benzene, xylene, and toluene; or combinations thereof.

[0089] However, the photoresist pattern according to one embodiment is not necessarily limited to being formed as a negative tone image, but may 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.

[0090] As mentioned above, the photoresist pattern 108 formed by exposure with light such as i-line (wavelength 365nm), KrF excimer laser (wavelength 248nm), ArF excimer laser (wavelength 193nm), as well as high-energy light such as EUV (Extreme Ultra Violet; wavelength 13.5nm) and E-Beam (electron beam), can have a thickness width of 5nm to 100nm. For example, the photoresist pattern 108 can be formed with thickness widths 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.

[0091] 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.

[0092] 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 also have a width corresponding to the photoresist pattern 108.

[0093] 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 as a thin film pattern 114.

[0094] The thin film 102 can be etched, for example, by dry etching using an etching gas, and the etching gas can be, for example, CHF3, CF4, Cl2, BCl3, or a mixture thereof.

[0095] 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]

[0096] The present invention will be described in more detail below through the examples relating to the manufacture of the semiconductor photoresist composition described above. However, the technical features of the present invention are not limited by the following examples.

[0097] Synthesis of organometallic compounds Synthesis Example 1 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.

[0098] The unreacted propionic acid is removed under reduced pressure to obtain the compound represented by the following chemical formula 4. [ka]

[0099] Synthesis Example 2 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 ethaneol, and stir at room temperature for 1 hour. Once the reaction is complete, filter, concentrate, and vacuum dry to obtain the compound represented by the following chemical formula 5. [ka]

[0100] 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, 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 6. [ka]

[0101] (Manufacturing of semiconductor photoresist compositions) Examples 1-10, Comparative Examples 1 and 2 The organometallic compounds represented by chemical formulas 4 to 6 obtained in Synthesis Examples 1 to 3 are each dissolved in 3% Propylene glycol methyl ether acetate (PGMEA), and diketone compounds A1 to A7 are added and dissolved in the weight ratios listed in Table 1 below. The mixture is then filtered through a 0.1 μm PTFE (polytetrafluoroethylene) syringe filter to produce the semiconductor photoresist compositions according to Examples 1 to 10, Comparative Example 1, and Comparative Example 2.

[0102] [Table 1]

[0103] [ka]

[0104] [Chain-like diketone compounds] A7: Acetylacetone

[0105] Evaluation: Sensitivity and Line Edge Roughness (LER) 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 with HMDS at 1500 rpm for 30 seconds, baked at 110°C for 60 seconds (post-apply bake, PAB), and then left at room temperature (23±2°C) for 30 seconds.

[0106] Subsequently, a linear array of 50 circular pads with a diameter of 500 μm was projected onto a wafer coated with the photoresist composition using EUV light (Lawrence Berkeley National Laboratory Micro Exposure Tool, MET). The pad exposure time was adjusted to ensure that the increasing EUV dose was applied to each pad.

[0107] The resist and substrate were then exposed on a hot plate at 160°C for 120 seconds and then baked. The baked film was developed with PGMEA solvent to form a negative tone image. Finally, the process was completed by baking on a hot plate at 150°C for 2 minutes.

[0108] The resist linewidth in response to exposed dose (energy) changes was measured using a CD-SEM. The appropriate sensitivity to exposure was determined from the resist linewidth values ​​formed differently for each exposure dose, and the sensitivity and LER were evaluated according to the following criteria. The results are shown in Table 2.

[0109] [Sensitivity evaluation criteria] -A: 50mJ / cm 2 less than -B: 50mJ / cm 2 That's all. [LER Evaluation Criteria] -○: 2nm or less -△: More than 2nm and less than 5nm -×: More than 5nm

[0110] [Table 2]

[0111] The results in Table 2 confirm that the patterns formed using the semiconductor photoresist compositions of Examples 1 to 10 ensure superior sensitivity and / or LER characteristics compared to Comparative Examples 1 and 2.

[0112] Although specific embodiments of the present invention have been described and illustrated above, it is obvious to those with ordinary skill in the art that the present invention is not limited to the described embodiments and can be modified and transformed in various ways 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]

[0113] 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. Organometallic compounds; Cyclic diketone compounds; and A composition for semiconductor photoresists, comprising a solvent.

2. The cyclic diketone compound is represented by the following chemical formula 1, the semiconductor photoresist composition according to claim 1: 【Chemistry 1】 In the aforementioned chemical formula 1, Ring A is a substituted or unsubstituted C3-C20 non-aromatic carbon ring group.

3. The semiconductor photoresist composition according to claim 2, wherein the C3-C20 non-aromatic carbon ring group is a saturated cyclic group having 3 to 20 carbon atoms as ring-forming atoms, or an unsaturated cyclic group having 3 to 20 carbon atoms as ring-forming atoms and containing at least one unsaturated bond within the ring.

4. The semiconductor photoresist composition according to claim 1, wherein the cyclic diketone compound is substituted with one or more hydroxyl groups.

5. The semiconductor photoresist composition according to claim 2, wherein ring A is a substituted or unsubstituted cyclobutane group, a substituted or unsubstituted cyclopentane group, a substituted or unsubstituted cyclohexane group, a substituted or unsubstituted cycloheptane group, a substituted or unsubstituted cyclooctane group, a substituted or unsubstituted cyclobutene group, a substituted or unsubstituted cyclopentene group, a substituted or unsubstituted cyclohexene group, a substituted or unsubstituted cycloheptene group, a substituted or unsubstituted cyclooctene group, or a combination thereof.

6. The cyclic diketone compound is one selected from the compounds listed in Group 1 below, according to claim 1, for the semiconductor photoresist composition: 【Chemistry 2】

7. The semiconductor photoresist composition according to claim 1, wherein the cyclic diketone compound is contained in an amount of 0.001 to 10% by weight based on 100% by weight of the semiconductor photoresist composition.

8. The semiconductor photoresist composition according to claim 1, wherein the organometallic compound is contained in an amount of 0.5% to 30% by weight based on 100% by weight of the semiconductor photoresist composition.

9. The semiconductor photoresist composition according to claim 1, further comprising an additive of a surfactant, a crosslinking agent, a leveling agent, an organic acid, an inhibitor (quencher), or a combination thereof.

10. The semiconductor photoresist composition according to claim 1, wherein the organometallic compound is an organotin compound containing at least one of an organic oxy group and an organic carbonyl oxy group.

11. The organometallic compound is represented by the following chemical formula 2, and is the semiconductor photoresist composition according to claim 1: 【Transformation 3】 In the aforementioned chemical formula 2, R １ 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 ２ ~R ４ are each independently 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, alkoxy and aryloxy (—OR ｂ , where R ｂ 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), a carboxyl group (—O(CO)R ｃ , R ｃ 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), an alkylamide or dialkylamide (—NR ｄ R ｅ , where R ｄ and R ｅ are each 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), an amidato (—NR ｆ (COR ｇ ), where R ｆ and R ｇ are each 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), an amidinato (—NR ｈ C (NR ｉ ) R ｊ Here, R ｈ , R ｉ and R ｊ 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 ｋ Here, R ｋ (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(CO)R ｌ , R ｌ (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 ２ ~R ４ At least one of them is an alkoxy and an aryloxy (-OR ｂ Here, R ｂ (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(CO)R ｃ , R ｃ (-NR) ｄ R ｅ Here, R ｄ and R ｅ 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 ｆ (COR ｇ ), here R ｆ and R ｇ 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 ｈ , R ｉ and R ｊ 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 ｋ Here, R ｋ (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(CO)R ｌ , R ｌ (The group 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.)

12. The aforementioned R ２ ~R ４ At least one of them is an alkoxy and an aryloxy (-OR ｂ Here, R ｂ (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(CO)R ｃ , R ｃ The semiconductor photoresist composition according to claim 11, 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.

13. The aforementioned R １ 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 ｂ 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 ｃ The semiconductor photoresist composition according to claim 12, 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.

14. The organometallic compound is represented by the following chemical formula 3 or chemical formula 4, and is part of the semiconductor photoresist composition according to claim 1: 【Chemistry 4】 In the aforementioned chemical formula 3, R ５ is a C1-C31 hydrocarbyl group, where 0 < z ≤ 2 and 0 < (z + x) ≤ 4; 【Transformation 5】 In the aforementioned chemical formula 4, R ６ 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 ｍ or -OC(=O)R ｎ And, The aforementioned R ｍ 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 ｎ 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. The values ​​a, b, c, and d are each independently integers between 1 and 20.

15. 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 14 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 the film to be etched using the aforementioned photoresist pattern as an etching mask.

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