Organometallic compound and photoresist composition containing the same

Abstract

The present invention relates to an organic metal compound in which two metals having excellent light absorption efficiency are introduced, and an extreme ultraviolet (EUV) semiconductor resist composition having improved extreme ultraviolet (EUV) photosensitivity and excellent etching resistance by including the organic metal compound, and a pattern forming method using the same.

Description

Technical Field

[0001] The present invention relates to an organometallic compound comprising a metal or non-metal with excellent light absorption efficiency in its central portion, an extreme ultraviolet (EUV) photosensitive photoresist composition containing the same, and a patterning method using the composition. Background Technology

[0002] Photoresist is a material whose chemical properties change under light exposure, and it is a key material used in the exposure process of forming intricate circuit patterns on semiconductor wafers. With the increasing integration of semiconductors, there is a need to achieve ultra-fine patterns, and organic-based chemically amplified resist (CAR) has been used as a standard material until the ArF generation, as a representative photoresist.

[0003] However, with the introduction of EUV and the miniaturization of processes, the following problems exist: carbon and oxygen, the main components of CAR, have very poor absorption efficiency for EUV photons; acid diffusion leads to a decrease in uniformity and roughness characteristics; and the low mechanical strength of organic-based photoresists causes pattern collapse during development. Therefore, due to the above problems, it is necessary to develop a novel inorganic photoresist with high absorption of EUV photons, excellent mechanical strength and etch resistance, and the ability to meet RLS (resolution, LER / LWR, sensitivity) characteristics.

[0004] In recent years, inorganic photoresists using coating methods based on liquid-phase chemical reactions and gas-phase chemical reactions have been recognized worldwide as the only alternative technology for forming ultra-fine patterns, but the original technology development of related materials / processes / equipment is still incomplete.

[0005] Therefore, in order to ensure technological competitiveness and take a leading position in next-generation EUV patterning technology, it is necessary to develop inorganic photoresist materials and processes. Summary of the Invention

[0006] The problem the invention aims to solve Therefore, the present invention provides an organometallic compound and an EUV photoresist composition containing the organometallic compound, wherein the organometallic compound and the EUV photoresist composition containing the organometallic compound can absorb EUV photons and have excellent etch resistance, thereby playing the role of a photoresist suitable for forming ultra-fine patterns.

[0007] In addition, the present invention provides a patterning method using the photoresist composition with excellent EUV photosensitivity and light absorption.

[0008] means for solving problems A specific example of the present invention provides an organometallic compound represented by the following chemical formula 1: [Chemical Formula 1]

[0009] In the chemical formula 1, A and B are each independently selected from groups 2 to 17, and A and B are different elements. R1 and R2 may be the same or different, and each is independently a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, wherein R1 and R2 do not form a ring with each other. L1 and L3 are each independently hydrolyzable ligands, and L2 and L2' are each independently selected from directly bonded, ether-, -NR3-, alkylene, or elements from groups 14 to 17. R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms. x, y, n, and m are each an independent integer from 1 to 10. a, c, x1, b, a', c', and b1 are each an independent integer from 0 to 5.

[0010] Another specific embodiment of the present invention provides a photoresist composition comprising an organometallic compound represented by the chemical formula 1 and a solvent.

[0011] Invention Effects According to the organometallic compound of the present invention, two metallic elements with excellent light absorption efficiency are introduced. Utilizing the excellent EUV light absorption of these two metals, a large number of secondary electrons can be released. Therefore, when the compound of Formula 1 is used in a photoresist composition, a photoresist with excellent etch resistance and easier absorption of EUV photons compared to conventional methods can be provided. Furthermore, when patterning is performed using a photoresist composition containing the organic compound, ultrafine patterns with excellent coatability, mechanical strength, etch resistance, and improved resolution can be formed without pattern collapse.

[0012] Therefore, the organometallic compounds can realize inorganic photoresist materials and technologies with excellent EUV photosensitivity and etch resistance, while also facilitating the fabrication of ultra-fine semiconductor devices using EUV. Detailed Implementation

[0013] The invention will be described in more detail below. The terms or words used in this specification and claims should not be construed as limited to their conventional or dictionary meanings, but should be interpreted as conforming to the technical concept of the invention, provided that the inventors can appropriately define the terms and concepts to best describe the invention.

[0014] Furthermore, the term "comprising" as used in the specification of this invention indicates the presence of a certain characteristic, region, integer, step, action, element, and / or component, and does not exclude the presence of other characteristics, regions, integers, steps, actions, elements, and / or components.

[0015] Examples of substituents are described in this specification, but are not limited thereto.

[0016] In this specification, the term "substitution" means that another atom or functional group replaces a hydrogen atom or a carbon atom in a compound to form a bond. There are no restrictions on the position of substitution, as long as a hydrogen atom or a carbon atom is substituted (i.e., the position where a substituent can be substituted). When two or more are substituted, the two or more substituents can be the same or different.

[0017] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, hydroxyl, carbonyl, ester, imide, amide, amino, carboxyl, sulfonic acid, sulfonamide, phosphine oxide, alkoxy, alkyl carbonyl, alkoxy carbonyl, sulfonyloxy, aryloxy, alkyl sulfoxy, aryl sulfoxy, alkyl sulfoxide group, aryl sulfoxide group, silyl, boron, aryl, and heteroaryl, or substituted or unsubstituted by two or more of the exemplified substituents linked together. For example, "substituents linked by two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent linked by two phenyl groups.

[0018] Examples of halogens in this specification include fluorine, chlorine, bromine, or iodine.

[0019] In this specification, alkyl groups can be straight-chain, branched, cyclic, or a combination thereof. There is no particular limitation on the number of carbon atoms in the straight-chain alkyl group, but it can be from 1 to 20. In addition, the number of carbon atoms in the branched and cyclic alkyl groups is from 3 to 20. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto. The alkyl group may be substituted or unsubstituted; when substituted, examples of substituents are as described above.

[0020] In this specification, an alkoxy group is a functional group attached to one end of an ether group (-O-) to which the aforementioned alkyl group is bonded. The foregoing description of alkyl groups may apply, except for functional groups bonded to an ether group (-O-). For example, the alkyl group may be linear, branched, or cyclic. There is no particular limitation on the number of carbon atoms in the alkoxy group, but the number of carbon atoms may be 1 to 20. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, cycloheptoxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto. The alkoxy group may be substituted or unsubstituted; when substituted, examples of substituents are as described above.

[0021] In this specification, amino groups can be selected from the group consisting of -NH2, monoalkylamino, dialkylamino, N-alkylarylamino, monoarylamino, diarylamino, N-arylheteroarylamino, N-alkylheteroarylamino, monoheteroarylamino, and diheteroarylamino. There is no particular limitation on the number of carbon atoms, but the number of carbon atoms can be from 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneylamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited to these. The amino group may be substituted or unsubstituted, and when substituted, examples of substituents are as described above.

[0022] In this specification, the amide group is a straight-chain alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, to which a hydrogen atom, is bonded. Specifically, the amide group can be a compound with the following structural formula, but is not limited thereto.

[0023]

[0024] In this specification, the ether group can be a directly bonded, straight-chain alkyl group with 1 to 30 carbon atoms, a branched alkyl group with 3 to 30 carbon atoms, a cyclic alkyl group with 3 to 30 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a combination thereof. Additionally, when the ether group is included as a divalent organic group, it can be directly bonded. The ether group can be a straight-chain alkyl group with 1 to 20 or 1 to 10 carbon atoms, a branched alkyl group with 3 to 20 or 3 to 10 carbon atoms, a cyclic alkyl group with 3 to 20 or 3 to 10 carbon atoms, an aryl group with 6 to 20 or 6 to 10 carbon atoms, or a combination thereof.

[0025] In this specification, for the ester group, the oxygen in the ester group may be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound with the following structural formula, but is not limited thereto.

[0026]

[0027] The following will describe in detail an organometallic compound, a photoresist composition containing the same, and a patterning method using the composition, according to a specific example of the present invention.

[0028] According to a specific example of the present invention, an organometallic compound represented by the following chemical formula 1 is provided: [Chemical Formula 1]

[0029] In the chemical formula 1, A and B are each independently selected from groups 2 to 17, and A and B are different elements. R1 and R2 may be the same or different, and each is independently a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, wherein R1 and R2 do not form a ring with each other. L1 and L3 are each independently hydrolyzable ligands, and L2 and L2' are each independently selected from directly bonded, ether-, -NR3-, alkylene, or elements from groups 14 to 17. R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms. x, y, n, and m are each an independent integer from 1 to 10. a, c, x1, b, a', c', and b1 are each an independent integer from 0 to 5.

[0030] This invention aims to provide an organometallic compound of Formula 1, which uses a metal precursor with high light absorption efficiency, thus ensuring improved sensitivity and excellent physical properties—a novel material. Furthermore, this invention aims to provide a semiconductor photoresist composition comprising an organic compound having the aforementioned properties, particularly suitable for EUV patterning technology.

[0031] According to the organometallic compound of the present invention, two specific metallic elements with excellent light absorption efficiency are introduced, thereby releasing a large number of secondary electrons through the excellent EUV light absorption of the two metals. Therefore, when the compound of Formula 1 is used in a photoresist composition, a photoresist that absorbs EUV photons while exhibiting excellent etch resistance can be provided.

[0032] Therefore, the organometallic compounds can realize inorganic photoresist materials and technologies, while also facilitating the fabrication of ultra-fine semiconductor devices using EUV.

[0033] Furthermore, to ensure high throughput and reduced shot noise in EUV photoresists, a central metal with high light absorption is required within the photoresist film. That is, a central metal capable of releasing a large number of secondary electrons through EUV light absorption needs to be introduced.

[0034] In this invention, two different metallic elements with excellent light absorption efficiency are introduced into the structure of Chemical Formula 1 to provide a photoresist that can absorb EUV photons while exhibiting excellent etch resistance.

[0035] Specifically, compared to ArF light sources, EUV light sources, which have high energy, produce fewer photons per unit area. This leads to an increased probability of shot noise, resulting in non-uniform circuits. Therefore, in this invention, by introducing two specific elements with high optical efficiency into the central metal portion of an organometallic compound, the EUV photon absorption rate is improved, thereby minimizing shot noise and overcoming the aforementioned problem, enabling the formation of uniform circuits or patterns.

[0036] Such organometallic compounds may contain two different types of metals at their center.

[0037] Furthermore, for the organometallic compounds of the present invention, having a linear or cyclic structure with one or more rings avoids the possibility of excessive bulkiness when the central portion contains two types of metals. This optimizes the absorption performance of EUV photons and allows the compounds to function as photoresists with excellent etch resistance. In this invention, the term "metals" refers to a combination of late-transition metals, quasi-metals, and non-metals.

[0038] Therefore, according to a specific embodiment of the present invention, when the organometallic compound and solvent are included, it can be used as a photoresist composition even without the inclusion of additional resin. That is, when the organometallic compound of chemical formula 1 is used as a photoresist precursor material in a photoresist composition (PR), it can exhibit excellent differences in physical properties compared to existing organic PRs.

[0039] Furthermore, organometallic compounds of Formula 1 containing two or more different metallic elements are advantageous for controlling nanoparticles, maximizing the dissolution rate of the exposed / non-exposed areas, and thus can be used as precursors when forming photoresist patterns using various light sources such as ArF, KrF, and EUV. In particular, organometallic compounds of Formula 1 are suitable for EUV applications.

[0040] Therefore, the present invention can provide materials and methods for forming nanoparticles by spin coating and vapor deposition when a photoresist comprising an organic compound of the stated chemical formula 1 is coated onto a substrate.

[0041] More specifically, A and B are different elements, and each of A and B can independently be an element selected from groups 2 to 17 or 13 to 17. Alternatively, each of A and B can independently be any element selected from groups 13 to 17, choosing from elements in periods 5 and 6.

[0042] According to a preferred specific example, A and B can each be independently selected from the group consisting of Sn, Sb, In, Te, and I. However, A and B do not contain any common elements.

[0043] In a specific instance, A is Zr, In, Sn, Sb or Hf, and B is Sn, Sb, In, Te or I, but A and B do not contain the same element.

[0044] For example, A can be Sn, Sb, or In.

[0045] Additionally, B can be Te or I.

[0046] In this case, when A and B, as elements with high light absorption efficiency, are included in the central part of the organometallic compound, the electron and photon absorption of EUV is improved, thereby releasing a large number of secondary electrons through EUV light absorption. Furthermore, according to a specific example, in this invention, compared to primarily containing only one metal element, when different A and B are included, the use of element B, which has a higher light absorption efficiency than A, can promote EUV photon absorption. A and B can be selected from elements in periods 5 and 6, wherein B can be an element with a higher light absorption efficiency than A.

[0047] More specifically, when A is Sn or In and B is Te or I, the light absorption efficiency can be further improved.

[0048] On the other hand, when x≥1 or x1≥1 in the chemical formula 1, y≥1 can be used. In this case, the chemical formula 1 can contain a linear or cyclic structure with more than one ring. Furthermore, under these conditions, when metal A is bonded to both sides of the central metal B, the remaining bonds of the central metal B, which is not bonded to metal A, may contain tetravalent organic groups with the same or different ligands bonded to them.

[0049] Furthermore, in the chemical formula 1, when x≥1 or x1≥1, y≥2 can be used. Therefore, the chemical formula 1 can have a cyclic structure with more than one ring.

[0050] For ligands of metals A and B that connect to the center of the organometallic compound, the weaker the bond with the metal element, the better the effect.

[0051] In this invention, L1 and L3 are hydrolyzable ligands, L2 and L2' are metal-linking groups, and R1 and R2 can represent photoactive substituents.

[0052] The L1 and L3 can each be independently an amino group, an amide group, an ether group, an ester group, or a combination thereof.

[0053] The L2 and L2' can each independently be directly bonded, ether-, -NH-, alkylene groups having 1 to 5 carbon atoms, or divalent organic groups containing group 16 elements. Specifically, the L2 and L2' can each independently be directly bonded or ether-. When the L2 and L2' are each independently directly bonded or ether-, the stability is better.

[0054] More specifically, if the chemical formula 1 is a cyclic structure, then L2 and L2' can be directly bonded. If the chemical formula 1 is a linear structure, then L2 can be an ether group, and L2' can be directly bonded.

[0055] Furthermore, R1 and R2 can each independently be a linear alkyl group with 1 to 20 carbon atoms or a branched alkyl group with 3 to 10 carbon atoms. Specifically, R1 and R2 can each independently be a linear alkyl group with 1 to 10 carbon atoms or a branched alkyl group with 3 to 10 carbon atoms. More specifically, when R1 and R2 are each tert-butyl, they are easily separated from the central metal and can exhibit superior performance. In particular, for tert-butyl, the β-hydrogen elimination reaction is more likely to occur compared to non-tert-butyl, thus further improving EUV photosensitivity.

[0056] In a specific embodiment of the present invention, the chemical formula 1 can satisfy the conditions of the following mathematical formula 1.

[0057] [Mathematical Expression 1] 0≤(a+c) / (n+m)≤2 In the mathematical formula 1, a, c, n and m are as defined in the chemical formula 1.

[0058] In another specific embodiment of the present invention, the chemical formula 1 can satisfy the conditions of the following mathematical formula 1.

[0059] [Mathematical Expression 1] 0.5≤(a+c) / (n+m)≤2 In the mathematical formula 1, a, c, n and m are as defined in the chemical formula 1.

[0060] It can be that b=0 and b1=0 in the chemical formula 1. In this case, it can be 1≤y≤4, 1≤x≤4, 1≤x1≤4, specifically x≥1, x1≥1, 1≤y≤2, and more specifically x=1, x1=1, y=2.

[0061] Since the chemical formula 1 satisfies the conditions of the mathematical formula 1, if there are more L ligands, the solubility of PR solution is excellent when it is prepared, and there are also more R substituents, resulting in more sites for photoreaction, thus making it easy to evaluate.

[0062] In a preferred embodiment of the invention, the compound represented by chemical formula 1 may be any one of the compounds represented by chemical formula 2, chemical formula 3 or chemical formula 4.

[0063] [Chemical Formula 2]

[0064] [Chemical Formula 3]

[0065] [Chemical Formula 4]

[0066] In chemical formulas 2 to 4, A and B are each independently elements selected from groups 2-17, and A and B are different elements. R1 and R2 may be the same or different, and each is independently a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, wherein R1 and R2 do not form a ring with each other. L1 and L3 are each independently hydrolyzable ligands. L2 can be independently a directly bonded, ether group, -NR3-, or an element selected from groups 14 to 17. R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms. n, m, and b are each an independent integer from 1 to 10. a, c, a', and c' are each an independent integer from 0 to 5.

[0067] The compound represented by Chemical Formula 2 may be selected from the group consisting of the following. The compound of Chemical Formula 2 may be an example of a cyclic structure, as described above, including cases where x≥1, x1≥1, y≥1, or y≥2 in Chemical Formula 1.

[0068]

[0069]

[0070]

[0071] The compound represented by the chemical formula 3 may be selected from one of the following groups.

[0072]

[0073]

[0074]

[0075] The compound represented by Chemical Formula 4 may be selected from the group consisting of the following. The compound of Chemical Formula 4 may be an example of a tetravalent organic group structure, as described above, including the cases where x≥1, x1≥1 and y≥1 in Chemical Formula 1, or the cases where b=0, b1=0 in Chemical Formula 1 and 1≤y≤4, 1≤x≤4, 1≤x1≤4.

[0076]

[0077] On the other hand, specific examples of methods for synthesizing the organometallic compounds are not too limited. As an example, compounds containing two different metals can be synthesized in an organic solvent via nucleophilic substitution reactions, etc.

[0078] All reactions can be carried out under an inert atmosphere of nitrogen or argon.

[0079] The reaction time varies with reactivity or reaction concentration, but it is usually more than 3 hours and less than 72 hours, and the reaction temperature can be more than -78°C and less than 150°C.

[0080] After the reaction is complete, the solution is filtered under reduced pressure to remove the salt, and the solvent in the resulting solution is completely removed. Purification can be carried out by methods selected from distillation, sublimation, recrystallization, etc., alone or in combination.

[0081] In addition, another specific embodiment of the invention according to this specification can provide a photoresist composition comprising an organometallic compound and a solvent.

[0082] In this invention, the photoresist composition may be a semiconductor photoresist composition for EUV.

[0083] As described above, in this invention, two metal components that can release a large number of secondary electrons by absorbing EUV light are introduced into the center of the organometallic compound. Moreover, when these two metal components are included, the compound has a linear or cyclic structure with one or more rings, thereby enabling it to function as a photoresist with excellent etch resistance while absorbing EUV photons.

[0084] Therefore, when the organometallic compound and solvent are included, it can be used as a photoresist composition even without additional resin.

[0085] Therefore, the present invention provides a semiconductor photoresist composition that meets basic photoresist performance requirements and exhibits excellent EUV photosensitivity and improved etch resistance. Furthermore, when patterning is formed using the photoresist composition containing the aforementioned organometallic compound, the presence of highly absorbent components in the photoresist film provides a high throughput EUV photoresist with reduced shot noise.

[0086] In this type of photoresist composition of the present invention, the content of the organometallic compound may be more than 1% by weight and less than 10% by weight relative to the total amount of the photoresist composition. If the content of the organometallic compound is less than 1% by weight, the low metal content leads to problems in performance improvement, while if the content of the organometallic compound is greater than 10% by weight, unnecessary processes such as etching are required to remove the metal.

[0087] As the organic solvent used in this invention, organic solvents commonly used in photoresist compositions that can dissolve the organometallic compounds and additives of Formula 1 can be used without limitation. For example, two or more ketones such as cyclohexanone and methylpentyl ketone; alcohols such as 2-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol can be used alone or in combination; ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, and diethylene glycol dimethyl ether; esters such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, tert-butyl propionate, and propylene glycol monotert-butyl ether acetate; lactone solvents such as γ-butyrolactone, but not limited thereto. Examples of the organic solvents are not strictly limited, but as an example, any one or a mixture thereof, such as PGMEA (propylene glycol monomethyl ether acetate), PGME (propylene glycol monomethyl ether), EL (ethyl lactate), CyH (cyclohexanone), can be used, as they have the best solubility for acid diffusion inhibitors.

[0088] The content of the organic solvent relative to 100% by weight of the total amount of the photoresist composition can be the remaining content in the photoresist composition other than the organometallic compound of formula 1.

[0089] Additionally, as needed, the photoresist composition may also contain one or more additives selected from the group consisting of photoacid generators, light absorbers, crosslinking agents, surfactants, and leveling agents. The additives may be present in quantities of 0.1 to 10 parts by weight relative to 100 parts by weight of the total photoresist composition.

[0090] There are no particular restrictions on the types of additives mentioned, and ingredients known in the field can be used. For example, photoacid generators include onium salts such as sulfonium salts or iodine salts, diazomethanes, oximes, nitrobenzyl sulfonates, imino sulfonates, disulfone acid generators, etc., which can be used alone or in combination of two or more.

[0091] Additionally, depending on the requirements, it may also include alkali-soluble resins, etc., commonly used in photoresist compositions.

[0092] In addition, another specific embodiment of the present invention according to this specification can provide a pattern forming method, which includes: a step of coating the photoresist composition onto a substrate to form a photoresist film; a step of exposing the photoresist film with an EUV light source; and a step of developing the exposed photoresist film to form a photoresist pattern.

[0093] The content regarding the photoresist composition includes the above content regarding the other specific example.

[0094] The coating method can be a wet and / or dry coating process. The wet coating method can be spin coating, and the dry coating method can be CVD, ALD deposition, etc., but is not limited to these.

[0095] The pattern formation method can employ known techniques, such as coating with a spinner, exposing the photoresist film to EUV high-energy rays with a wavelength of less than 300 nm using a specified photomask, and then developing the exposed photoresist film with a conventional developer (e.g., an alkaline aqueous solution such as tetramethylammonium hydroxide aqueous solution of more than 0.1% by weight and less than 10% by weight).

[0096] Specifically, the pattern forming method can form a pattern through the following steps: coating the above-mentioned photoresist composition onto a silicon wafer substrate; heating the coated substrate to form a photoresist film; exposing the photoresist film using a selected high-energy exposure source; removing acid-unstable groups from the polymer resin by means of acid generated in the exposure section; and developing the photoresist film with altered solubility using the developing solution.

[0097] Optionally, for photoresist compositions, in addition to extreme ultraviolet (EUV) light, high-energy rays with wavelengths below 300 nm can also be used as exposure sources to form high-performance patterns. Examples of high-energy rays with wavelengths below 300 nm include ultraviolet light, far ultraviolet light, electron beams, X-rays, excimer lasers, gamma rays, or synchrotron radiation.

[0098] In addition, in order to form fine patterns below 70 nm, it is preferable to use an exposure device with a short-wavelength high-energy X-ray source such as ArF excimer laser, KrF excimer laser or EUV.

[0099] For the substrate, a circular silicon wafer with a diameter of 8 inches or 12 inches can be used as the substrate for depositing thin films.

[0100] More specifically, the high-energy light source can be EUV with a wavelength of 13.5 nm, or KrF with a wavelength of 248 nm, ArF with a wavelength of 193 nm, or electron beams (e-beam) as needed.

[0101] In addition, the photoresist pattern can be formed by etching using known methods.

[0102] The photoresist pattern formed by the method can have a linewidth of 5 to 100 nm and a linewidth roughness of less than 50 nm. Alternatively, the photoresist pattern can have a linewidth of 5 to 50 nm and a linewidth roughness of less than 10 nm.

[0103] The following examples are provided to aid in understanding the present invention. However, the following examples are merely illustrative of the invention, and the invention is not limited to the following examples.

[0104] Synthetic Examples 1 to 26: Preparation of compounds represented by chemical formula 1 <Synthesis Example 1> Synthesis of the compound represented by chemical formula 5 [Chemical Formula 5]

[0105] After completely shielding a 500ml round-bottom flask with a side arm from light by wrapping it with aluminum foil, add 30.0g (0.04mol) of [(Dimethylamine)2-Sn-Te]2. Then, add 300ml of anhydrous tetrahydrofuran and stir for 1 hour. Lower the reactor temperature to -20°C and slowly add 10.5g (0.09mol) of […]. t BuMgCl (1.0 M in THF). After the addition was complete, the temperature was slowly increased, and the mixture was stirred at room temperature for 8 hours to stop the reaction. Then, the resulting reaction product solution was filtered under reduced pressure to remove the salt, and the solvent in the resulting solution was completely removed to give the compound represented by chemical formula 5, in a yield of 72%.

[0106] 1 H-NMR (C6D6): δ 1.34 (s, 18H), δ 2.42 (s, 12H).

[0107] <Synthesis Example 2> Synthesis of the compound represented by chemical formula 6 [Chemical Formula 6]

[0108] In Synthesis Example 2, except that [(tert-butoxy)2-Sn-Te]2 was used instead of [(dimethylamine)2-Sn-Te]2, the compound represented by Chemical Formula 6 was synthesized by the same method as in Synthesis Example 1, with a yield of 69%.

[0109] 1 H-NMR (C6D6): δ 1.27 (t, 18H), δ 1.32 (s, 18H).

[0110] <Synthesis Example 3> Synthesis of the compound represented by chemical formula 7 [Chemical Formula 7]

[0111] In Synthesis Example 3, except that [(Propionate)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2, the compound represented by Chemical Formula 7 was synthesized by the same method as in Synthesis Example 1, with a yield of 75%.

[0112] 1 H-NMR (C6D6): δ 1.04 (t, 6H), δ 1.41 (s, 18H), δ 2.31 (q, 4H).

[0113] <Synthesis Example 4> Synthesis of the compound represented by chemical formula 8 [Chemical Formula 8]

[0114] After completely shielding the light from light by wrapping a 250ml round-bottom flask with a side arm, add 10.0g (0.03mol) of ( t Bu)2Sn(dimethylamine)Cl(( t Bu)2Sn(Dimethylamine)Cl). Then, after adding 100 ml of anhydrous tetrahydrofuran, the reactor temperature was lowered to -20 °C, and 4.8 g (0.03 mol) of NaI was slowly added. After the addition was complete, the temperature was slowly increased, and the reaction was stopped after reflux for 8 hours. Then, the resulting reaction product solution was filtered under reduced pressure to remove the salt, and the solvent in the resulting solution was completely removed to give the compound represented by chemical formula 8, with a yield of 68%.

[0115] 1 H-NMR (C6D6): δ 1.40 (s, 36H), δ 2.47 (s, 12H).

[0116] <Synthesis Example 5> Synthesis of the compound represented by chemical formula 9 [Chemical Formula 9]

[0117] In the synthetic example 5, in addition to using ( t Bu)2Sn(tert-butoxy)Cl(( t Bu)2Sn(t-botoxide)Cl) replaces ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 9 was synthesized by the same method as in Synthesis Example 4, with a yield of 75%.

[0118] 1 H-NMR (C6D6): δ 1.24 (t, 18H), δ 1.31 (s, 36H).

[0119] <Synthesis Example 6> Synthesis of the compound represented by chemical formula 10 [Chemical Formula 10]

[0120] In the synthetic example 6, in addition to using ( t Bu)2Sn(propionate)Cl replaces ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 10 was synthesized by the same method as in Synthesis Example 4, with a yield of 79%.

[0121] 1 H-NMR (C6D6): δ 1.05 (t, 6H), δ 1.37 (s, 36H), δ 2.31 (q, 4H).

[0122] <Synthesis Example 7> Synthesis of the compound represented by chemical formula 11 [Chemical Formula 11]

[0123] In the synthetic example 7, [(tert-butoxy)2-Sn-Te]2 was used instead of [(dimethylamine)2-Sn-Te]2, and MeMgCl was used instead of... t Apart from BuMgCl, the compound represented by chemical formula 11 was synthesized by the same method as in Synthesis Example 1, with a yield of 78%.

[0124] 1 H-NMR (C6D6): δ 0.62 (s, 6H), δ 1.18 (s, 18H).

[0125] <Synthesis Example 8> Synthesis of the compound represented by chemical formula 12 [Chemical Formula 12]

[0126] In the synthetic example 8, except that [(tert-butoxy)2-Sn-Te]2 was used instead of [(dimethylamine)2-Sn-Te]2 and PhMgBr was used instead of t Apart from BuMgCl, the compound represented by chemical formula 12 was synthesized by the same method as in Synthesis Example 1, with a yield of 72%.

[0127] 1 H-NMR (C6D6): δ 1.42 (s, 18H), δ 7.33 (m, 10H).

[0128] <Synthesis Example 9> Synthesis of the compound represented by chemical formula 13 [Chemical Formula 13]

[0129] In the synthetic example 9, [(propionate)2-Sn-Te]2 was used instead of [(dimethylamine)2-Sn-Te]2, and MeMgCl was used instead of t Apart from BuMgCl, the compound represented by chemical formula 13 was synthesized by the same method as in Synthesis Example 1, with a yield of 74%.

[0130] 1 H-NMR (C6D6): δ 0.71 (s, 6H), δ 1.07 (t, 6H), δ 2.24 (q, 4H).

[0131] <Synthesis Example 10> Synthesis of the compound represented by chemical formula 14 [Chemical Formula 14]

[0132] In the synthetic example 10, except that [(propionate)2-Sn-Te]2 was used instead of [(dimethylamine)2-Sn-Te]2 and PhMgBr was used instead of t Apart from BuMgCl, the compound represented by chemical formula 14 was synthesized by the same method as in Synthesis Example 1, with a yield of 68%.

[0133] 1 H-NMR (C6D6): δ 1.13 (t, 6H), δ 2.32 (q, 4H), δ 7.32 (m, 10H). <Synthetic Example 11> Synthesis of the compound represented by chemical formula 15 [Chemical Formula 15]

[0134] In the synthetic example 11, except that (Me)₂Sn(propionate)Cl was used instead of ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 15 was synthesized by the same method as in Synthesis Example 4, with a yield of 75%.

[0135] 1 H-NMR (C6D6): δ 0.61 (s, 12H), δ 1.04 (t, 6H), δ 2.38 (q, 4H).

[0136] <Synthesis Example 12> Synthesis of the compound represented by chemical formula 16 [Chemical Formula 16]

[0137] In the synthetic example 12, (Me)Sn(propionate)₂Cl was used instead of ( t Apart from Bu)2Sn(Dimethylamine)Cl, the compound represented by chemical formula 16 was synthesized by the same method as in Synthesis Example 4, with a yield of 78%.

[0138] 1 H-NMR (C6D6): δ 0.62 (s, 6H), δ 1.09 (t, 12H), δ 2.42 (q, 8H). <Synthesis Example 13> Synthesis of the compound represented by chemical formula 17 [Chemical Formula 17]

[0139] In the synthetic example 13, in addition to using ( t Bu)In(dimethylamine)Cl replaces ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 17 was synthesized by the same method as in Synthesis Example 4, with a yield of 71%.

[0140] 1H-NMR (C6D6): δ 1.22 (s, 18H), δ 2.47 (s, 12H).

[0141] <Synthesis Example 14> Synthesis of the compound represented by chemical formula 18 [Chemical Formula 18]

[0142] In the synthetic example 14, in addition to using ( t Bu)In(tert-butoxy)Cl replaces ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 18 was synthesized by the same method as in Synthesis Example 4, with a yield of 78%.

[0143] 1 H-NMR (C6D6): δ 1.32 (s, 18H), δ 1.49 (s, 18H).

[0144] <Synthesis Example 15> Synthesis of the compound represented by chemical formula 19 [Chemical Formula 19]

[0145] In the synthetic example 15, in addition to using ( t Bu)In(propionate)Cl replaces ( t Apart from Bu)2Sn(dimethylamine)Cl, the compound represented by chemical formula 19 was synthesized by the same method as in Synthesis Example 4, with a yield of 73%.

[0146] 1 H-NMR (C6D6): δ 1.05 (t, 6H), δ 1.41 (s, 18H), δ 2.27 (q, 4H).

[0147] <Synthesis Example 16> Synthesis of the compound represented by chemical formula 20 [Chemical Formula 20]

[0148] Wrap a 500ml round-bottom flask with a side arm in aluminum foil to completely block out light, then add 20.0g (0.06mol) of [a specific ingredient / component]. t BuSn (dimethylamine) 3. Then, after adding 300 ml of anhydrous tetrahydrofuran, the reactor temperature was lowered to -20°C, and 20.6 g (0.06 mol) of [unspecified ingredient] was added. tBuTe (dimethylamine) 3, 1.2 g (0.06 mol) of H2O were added and the mixture was heated and stirred at room temperature for 18 hours. Then, the resulting reaction product solution was filtered under reduced pressure to remove the salt, and the solvent in the resulting solution was completely removed to give the compound represented by the chemical formula 20, in a yield of 76%.

[0149] 1 H-NMR (C6D6): δ 1.28 (s, 9H), δ 1.33 (s, 9H), δ 2.43 (s, 12H), δ2.52 (s, 12H).

[0150] <Synthesis Example 17> Synthesis of the compound represented by chemical formula 21 [Chemical Formula 21]

[0151] In the synthetic example 17, in addition to using t BuSn(t-butoxide)3 replaces t BuSn (Dimethylamine) 3. Use t BuTe(t-butoxide)3 replaces t Apart from BuTe(Dimethylamine)3, the compound represented by chemical formula 21 was synthesized by the same method as in Synthesis Example 16, with a yield of 73%.

[0152] 1 H-NMR (C6D6): δ 1.18 (s, 9H), δ 1.21 (s, 9H), δ 1.25 (s, 18H), δ1.29 (s, 18H).

[0153] <Synthesis Example 18> Synthesis of the compound represented by chemical formula 22 [Chemical Formula 22]

[0154] In the synthetic example 18, in addition to using t BuSn (propionate) 3 substitute t BuSn (dimethylamine) 3. Use t BuTe (propionate) 3 substitute t Apart from BuTe (dimethylamine) 3, the compound represented by chemical formula 22 was synthesized by the same method as in Synthesis Example 16, with a yield of 63%.

[0155] 1H-NMR (C6D6): δ 1.01 (t, 3H), δ 1.13 (t, 3H), δ 1.23 (s, 9H), δ 1.32(s, 9H), δ 2.27 (q, 2H), δ δ 2.32 (q, 2H).

[0156] <Synthesis Example 19> Synthesis of the compound represented by chemical formula 23 [Chemical Formula 23]

[0157] In the synthetic example 19, except that MeSn (dimethylamine)3 was used instead t BuSn (dimethylamine)3, use MeTe (dimethylamine)3 instead. t Apart from BuTe (dimethylamine) 3, the compound represented by chemical formula 23 was synthesized by the same method as in Synthesis Example 16, with a yield of 79%.

[0158] 1 H-NMR (C6D6): δ 0.56 (s, 3H), δ 0.64 (s, 3H), δ 2.46 (s, 12H), δ2.52 (s, 12H).

[0159] <Synthesis Example 20> Synthesis of the compound represented by chemical formula 24 [Chemical Formula 24]

[0160] In the synthetic example 20, PhSn(dimethylamine)3 was used instead of t BuSn (dimethylamine)3, replace with PhTe (dimethylamine)3 t Apart from BuTe (dimethylamine) 3, the compound represented by chemical formula 24 was synthesized by the same method as in Synthesis Example 16, with a yield of 73%.

[0161] 1 H-NMR (C6D6): δ 2.38 (s, 12H), δ2.54 (s, 12H), δ7.42 (m, 5H), δ7.58(m, 5H).

[0162] <Synthetic Example 21> Synthesis of the compound represented by chemical formula 25 [Chemical Formula 25]

[0163] In Synthesis Example 21, except that H2S was used instead of H2O, the compound represented by Chemical Formula 25 was synthesized by the same method as in Synthesis Example 16, with a yield of 69%.

[0164] 1 H-NMR (C6D6): δ 1.33 (s, 9H), δ 1.36 (s, 9H), δ 2.25 (s, 12H), δ2.38 (s, 12H). <Synthesis Example 22> Synthesis of the compound represented by chemical formula 26 [Chemical Formula 26]

[0165] In Synthesis Example 22, except that H2Se was used instead of H2O, the compound represented by Chemical Formula 26 was synthesized by the same method as in Synthesis Example 16, with a yield of 71%.

[0166] 1 H-NMR (C6D6): δ 1.22 (s, 9H), δ 1.31 (s, 9H), δ 2.18 (s, 12H), δ2.41 (s, 12H).

[0167] <Synthesis Example 23> Synthesis of the compound represented by chemical formula 27 [Chemical Formula 27]

[0168] In Synthesis Example 23, except that NH3 was used instead of H2O, the compound represented by Chemical Formula 27 was synthesized by the same method as in Synthesis Example 16, with a yield of 74%.

[0169] 1 H-NMR (C6D6): δ 1.27 (s, 9H), δ 1.34 (s, 9H), δ 2.13 (s, 1H), δ 2.21 (s, 12H), δ 2.28 (s, 12H). <Synthesis Example 24> Synthesis of the compound represented by chemical formula 28 [Chemical Formula 28]

[0170] In Synthesis Example 24, except that CH4 was used instead of H2O, the compound represented by Chemical Formula 28 was synthesized by the same method as in Synthesis Example 16, with a yield of 68%.

[0171] 1 H-NMR (C6D6): δ 1.24 (s, 9H), δ 1.31 (s, 9H), δ 1.44 (s, 2H), δ 2.31 (s, 12H), δ 2.34 (s, 12H).

[0172] <Synthesis Example 25> Synthesis of the compound represented by chemical formula 29 [Chemical Formula 29]

[0173] Wrap a 500ml round-bottom flask with a side arm in aluminum foil to completely block out light, then add 20.0g (0.05mol) of [Sn-(dimethylamine)₂]₂. Next, add 300ml of anhydrous tetrahydrofuran and stir for 1 hour. Lower the reactor temperature to -20°C and slowly add 35.7g (0.10mol) of [Sn-(dimethylamine)₂]. t Bu-Te]2. After the addition is complete, the temperature is slowly increased, and the reaction is stopped by stirring at room temperature for 18 hours. Then, the resulting reaction product solution is filtered under reduced pressure to remove the salt, and the solvent in the resulting solution is completely removed to obtain the compound represented by the chemical formula 29, with a yield of 69%.

[0174] 1 H-NMR (C6D6): δ 1.40 (s, 18H), δ 2.39 (s, 12H).

[0175] <Synthesis Example 26> Synthesis of the compound represented by chemical formula 30 [Chemical Formula 30]

[0176] A 500 ml round-bottom flask with a side arm was wrapped in aluminum foil to completely block light, and 15.0 g (0.03 mol) of [Chemical Formula 29] was added. Then, 300 ml of anhydrous tetrahydrofuran was added and stirred. The reactor temperature was lowered to -20 °C, and 3.9 g of propionic acid (0.05 mol) was slowly added. After the addition was complete, the temperature was slowly increased, and the reaction was stirred at room temperature for 18 hours to complete the reaction. The resulting reaction product solution was then filtered under reduced pressure to remove the salt, and the solvent was completely removed from the resulting solution to obtain the compound represented by Chemical Formula 30, in 83% yield.

[0177] 1 H-NMR (C6D6): δ 1.15 (t, 6H), δ 1.43 (s, 18H), δ 2.33 (q, 4H).

[0178] <Examples 1 to 26> The compounds represented by chemical formulas 5 to 30 synthesized in Examples 1 to 26 were dissolved in propylene glycol monomethyl ether ester (PGMEA) at a concentration of 2 wt%, mixed, and filtered to prepare a semiconductor photoresist composition. An 8-inch diameter circular silicon wafer with a native oxide surface was used as a substrate for thin film deposition.

[0179] The semiconductor photoresist composition according to Examples 1 to 26 was spin-coated onto the pretreated substrate at a speed of 1500 rpm for 30 seconds, and then baked on a hot plate at 180°C for 120 seconds to form a thin film.

[0180] <Comparative Examples 1 to 2> Except for using the compounds of Comparative Compound 1 and Comparative Compound 2 in Table 1 below as organometallic compounds instead of the compound represented by Chemical Formula 5, the photoresist composition and thin film pattern were formed by the same method as in Example 1.

[0181] [Table 1]

[0182] <Experimental Example> The exposure characteristics of the photoresist pattern were evaluated using the following method, and the results are shown in Table 2.

[0183] (1) Evaluation of coating properties After coating and baking the compounds represented by chemical formulas 5 to 30, the thickness of the film was measured by ellipsometry, and the measured thickness was approximately 10-50 nm.

[0184] Coating Standards The number of defects was detected using the SP-5 equipment, and the coating evaluation criteria are as follows: ○: The number of defects is 5 or less. X: The number of defects exceeds 5 (2) Sensitivity Thin films of Examples 1 to 26 and Comparative Examples 1 to 2, prepared by coating and baking the compounds represented by chemical formulas 5 to 30 and comparative compounds 1 and 2, were exposed to EUV radiation. After exposure, a post-exposure bake (PEB) was performed at 170°C for 120 seconds. The baked films were then immersed in a developer and rinsed to form a negative tone image. The residual photoresist thickness was measured using an ellipsometer. gThe gel dosage (dosage) is shown in Table 2 below according to the type of photoresist. Compared with using only a single high-absorbency element (comparative example), the patterns formed using the semiconductor photoresist composition exhibit excellent sensitivity.

[0185] [Table 2]

[0186] As shown in Table 2 above, Examples 1 to 26 used organometallic compounds with chemical formulas 5 to 30 containing two different metals. Therefore, compared with Comparative Examples 1 and 2, which used only a single metal, their coating properties and sensitivity characteristics were superior. Furthermore, in the organometallic compounds with chemical formulas 5 to 30, the cyclic form contains more elements per molecule than the chain form, resulting in relatively better performance. In contrast, when only a single metal is contained, even if the compound structure contains two metals, Comparative Example 1, using Comparative Compound 1, showed good coating properties but poorer sensitivity than the Examples. Additionally, for Comparative Compound 2, during EUV evaluation, there was no alkyl chain capable of photoreaction, and the compound was unstable in air, making coating impossible and thus Comparative Example 2 could not complete the exposure evaluation.

Claims

1. An organometallic compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, A and B are each independently selected from groups 2 to 17, and A and B are different elements. R1 and R2 may be the same or different, and each is independently a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, wherein R1 and R2 do not form a ring with each other. L1 and L3 are each independently hydrolyzable ligands, and L2 and L2' are each independently directly bonded, etherified, secondary amine, alkylene, or elements selected from groups 14 to 17. x, y, n, and m are each independent integers from 1 to 10. a, c, x1, b, a', c', and b1 are each an independent integer from 0 to 5.

2. The organometallic compound according to claim 1, wherein, A and B are each independently selected from the group consisting of Sn, Sb, In, Te, or I.

3. The organometallic compound according to claim 1, wherein, A is Zr, In, Sn, Sb or Hf, and B is Sn, Sb, In, Te or I, but A and B do not contain the same element.

4. The organometallic compound according to claim 1, wherein, A is Sn, Sb, or In, and B is Te or I.

5. The organometallic compound according to claim 1, wherein, In the chemical formula 1, when x≥1 and x1≥1, y≥1.

6. The organometallic compound according to claim 1, wherein, In the chemical formula 1, when x≥1 and x1≥1, y≥2.

7. The organometallic compound according to claim 1, wherein, R1 and R2 are each independently a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms.

8. The organometallic compound according to claim 1, wherein, L1 and L3 are each independently one of amino, amide, ether, ester, or a combination thereof.

9. The organometallic compound according to claim 1, wherein, L2 and L2' are each independently direct-bonded or ether.

10. The organometallic compound according to claim 1, wherein, Chemical formula 1 satisfies the following conditions: [Mathematical Expression 1] 0≤(a+c) / (n+m)≤2 In the mathematical formula 1, a, c, n and m are as defined in the chemical formula 1.

11. The organometallic compound according to claim 1, wherein, In the chemical formula 1, b=0 and b1=0.

12. The organometallic compound according to claim 1, wherein, The compound represented by chemical formula 1 is any one of the compounds represented by chemical formula 2, chemical formula 3 or chemical formula 4: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the chemical formulas 2 to 4, A and B are each independently selected from groups 2-17, and A and B are different elements; R1 and R2 may be the same or different, and each independently is a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a cyclic alkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a combination thereof, wherein R1 and R2 do not form a ring with each other; L1 and L3 are each independently hydrolyzable ligands; L2 can be independently a directly bonded, ether group, -NR3-, or an element selected from groups 14 to 17; R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms; n, m, and b are each an independent integer from 1 to 10; a, c, a', and c' are each an independent integer from 0 to 5.

13. The organometallic compound according to claim 12, wherein, The compound represented by chemical formula 2 is selected from one of the following groups: 。 14. The organometallic compound according to claim 12, wherein, The compound represented by chemical formula 3 is selected from one of the following groups: 。 15. The organometallic compound according to claim 12, wherein, The compound represented by chemical formula 4 is selected from one of the following groups: 。 16. A photoresist composition, wherein, It comprises the organometallic compound and solvent as described in claim 1.

17. The photoresist composition according to claim 16, wherein, The content of the organometallic compound is more than 1% by weight and less than 10% by weight relative to the total amount of the photoresist composition.

18. The photoresist composition according to claim 16, wherein, The photoresist composition further comprises one or more additives selected from the group consisting of photoacid generators, light absorbers, crosslinking agents, surfactants, and leveling agents.

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