Organometallic compounds and photoresist composition comprising same

Abstract

The present invention relates to an organometallic compound into which two kinds of metals having excellent light absorption efficiency are introduced, a semiconductor photoresist composition for EUV having improved sensitivity to EUV and excellent etch resistance by comprising the compound, and a pattern forming method using same.

Description

Organometallic compound and photoresist composition containing the same

[0001] The present invention relates to an organometallic compound containing a metal or non-metal having excellent light absorption efficiency at the center, a composition for an EUV-sensitive photoresist containing the same, and a method for forming a pattern using the same.

[0002] Photoresist, a material whose chemical properties change upon exposure to light, is a key material used in the exposure process to form precise circuit patterns on semiconductor wafers. With the increasing integration of semiconductors, the implementation of ultra-fine patterns is becoming increasingly necessary. A representative photoresist, organic-based chemically amplified resist (CAR), has been used as a standard material up until the ArF generation.

[0003] However, with the introduction of EUV and process refinement, there are problems such as very poor photon absorption efficiency of carbon and oxygen, which are the main components of CAR, for photons in the EUV wavelength band, deterioration of uniformity and roughness characteristics due to acid diffusion, and pattern collapse during development due to low mechanical strength of organic-based photoresists. Therefore, due to the above problems, there is a need to develop a new inorganic photoresist that can satisfy the RLS (Resolution, LER / LWR, Sensitivity) characteristics by having high photon absorption for EUV wavelength band and excellent mechanical strength and etching resistance.

[0004] Recently, inorganic photoresists using a coating method based on liquid and gas phase chemical reactions have been recognized worldwide as the only alternative technology for forming ultra-fine patterns. However, the development of core technologies for related materials, processes, and equipment is insufficient.

[0005] Therefore, in order to secure technological competitiveness and take the lead in next-generation EUV patterning technology, the development of inorganic photoresist materials and processes must be carried out.

[0006] Accordingly, the present invention provides an organometallic compound capable of absorbing EUV photons and having excellent etching resistance, thereby serving as a photoresist suitable for forming ultra-fine patterns, and an EUV photoresist composition comprising the same.

[0007] In addition, the present invention provides a method for forming a pattern using the photoresist composition having excellent EUV photosensitivity and absorbance.

[0008] One embodiment of the invention provides an organometallic compound represented by the following chemical formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] A and B are each independently an element selected from groups 2 to 17, and A and B are different elements,

[0013] R1 and R2 are the same or different from each other, and each independently represents 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, and R1 and R2 do not form a ring with each other.

[0014] L1 and L3 are each independently a hydrolyzable ligand, L2 and L2' are each independently a direct bond, ether, -NR3-, alkylene or an element selected from groups 14 to 17,

[0015] R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,

[0016] x, y, n, and m are each independently integers from 1 to 10,

[0017] a, c, x1, b, a', c', and b1 are each independently integers from 0 to 5.

[0018] Another embodiment of the invention provides a photoresist composition comprising an organometallic compound represented by the above chemical formula 1; and a solvent.

[0019]

[0020] The organometallic compound according to the present invention can emit a large amount of secondary electrons through the excellent EUV absorption of two metal elements having excellent absorption efficiency by introducing the two metal elements. Therefore, when the compound of the above chemical formula 1 is used in a photoresist composition, a photoresist can be provided that absorbs EUV photons more easily than before and has excellent etching resistance. In addition, when a pattern is formed using a photoresist composition including the above organic compound, an ultrafine pattern can be formed that has excellent coating properties and improved mechanical strength, etching resistance, and resolution without pattern collapse.

[0021] Therefore, the above organometallic compound can contribute to the production of ultra-fine semiconductor devices using EUV while realizing inorganic photoresist materials and technologies with excellent EUV photosensitivity and etching resistance.

[0022]

[0023] The present invention is described in more detail below. Terms and words used in this specification and claims should not be construed as limited to their conventional or dictionary meanings. Rather, they should be interpreted with meanings and concepts consistent with the technical spirit of the present invention, based on the principle that the inventor can appropriately define the concepts of terms to best explain his or her invention.

[0024] Additionally, the meaning of "comprising" as used in the specification of the present invention specifies a specific characteristic, region, integer, step, operation, element and / or component, and does not exclude the presence or addition of other characteristics, regions, integers, steps, operations, elements and / or components.

[0025] In this specification, examples of substituents are described below, but are not limited thereto.

[0026] In this specification, the term "substitution" means that another atom or functional group is bonded in place of a hydrogen atom or a carbon atom in a compound, and the position of substitution is not limited as long as it is the position where the hydrogen atom or carbon atom is substituted, that is, a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0027] The term "substituted or unsubstituted" as used herein means a group that is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; amino group; carboxyl group; sulfonic acid group; sulfonamide group; phosphine oxide group; alkoxy group; alkylcarbonyl group; alkoxycarbonyl group; sulfonyloxy group; aryloxy group; alkylthioxy group; arylthioxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; aryl group; and heteroaryl group, or a group that is substituted or unsubstituted in which two or more of the above-mentioned substituents are connected. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0028] In this specification, examples of halogen include fluorine, chlorine, bromine or iodine.

[0029] In the present specification, the alkyl group may be linear, branched, cyclic, or a combination thereof, and the number of carbon atoms in the linear alkyl group is not particularly limited, but may be 1 to 20. In addition, the number of carbon atoms in the branched and cyclic alkyl groups is 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, cyclohexetylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples thereof include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl. The alkyl group may be substituted or unsubstituted, and examples of the substituent when substituted are as described above.

[0030] In this specification, an alkoxy group is a functional group in which the aforementioned alkyl group is bonded to one end of an ether group (-O-), and the description of the aforementioned alkyl group may be applied to these groups, except that they are functional groups bonded to an ether group (-O-). For example, the alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be 1 to 20 carbon atoms. Specifically, there are, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, cycloheptoxy, benzyloxy, p-methylbenzyloxy, etc. The alkoxy group may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0031] In the present specification, the amino group may be selected from the group consisting of -NH2, a monoalkylamino group, a dialkylamino group, an N-alkylarylamino group, a monoarylamino group, a diarylamino group, an N-arylheteroarylamino group, an N-alkylheteroarylamino group, a monoheteroarylamino group, and a diheteroarylamino group, and the number of carbon atoms is not particularly limited, but may be 1 to 30. Specific examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methyl-anthracenylamino, diphenylamino, ditolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, ditolylamino, N-phenyltolylamino, triphenylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc. The amino group may be substituted or unsubstituted, and when substituted, examples of the substituent are as described above.

[0032] In the present specification, the amide group may be a compound having a hydrogen atom, 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, bonded to the nitrogen of the amide group. Specifically, the amide group may be a compound having the following structural formula, but is not limited thereto.

[0033]

[0034] In the present specification, the ether group may be a direct bond, 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. In addition, when the ether group includes a divalent organic group, it may be a direct bond. The ether group may be a linear alkyl group having 1 to 20 or 1 to 10 carbon atoms, a branched alkyl group having 3 to 20 or 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 20 or 3 to 10 carbon atoms, an aryl group having 6 to 20 or 6 to 10 carbon atoms, or a combination thereof.

[0035] In the present specification, the ester group may have the oxygen of the ester group replaced by a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.

[0036]

[0037]

[0038] Hereinafter, an organometallic compound according to one embodiment of the invention, a photoresist composition containing the same, and a pattern forming method using the same will be described in detail.

[0039] According to one embodiment of the invention, an organometallic compound represented by the following chemical formula 1 is provided:

[0040] [Chemical Formula 1]

[0041]

[0042] In the above chemical formula 1,

[0043] A and B are each independently an element selected from groups 2 to 17, and A and B are different elements,

[0044] R1 and R2 are the same or different from each other, and each independently represents 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, and R1 and R2 do not form a ring with each other.

[0045] L1 and L3 are each independently a hydrolyzable ligand, L2 and L2' are each independently a direct bond, ether, -NR3-, alkylene or an element selected from groups 14 to 17,

[0046] R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,

[0047] x, y, n, and m are each independently integers from 1 to 10,

[0048] a, c, x1, b, a', c', and b1 are each independently integers from 0 to 5.

[0049] The present invention provides an organometallic compound of chemical formula 1 using a metal precursor with high light absorption efficiency, which can secure a novel material with improved sensitivity and excellent physical properties. In addition, the present invention aims to provide a composition for a semiconductor photoresist particularly suitable for EUV patterning technology, which comprises an organic compound having the above characteristics.

[0050] The organometallic compound according to the present invention can emit a large amount of secondary electrons through excellent EUV absorption of two specific metal elements with excellent light absorption efficiency by introducing the two metal elements. Therefore, when the compound of the above chemical formula 1 is used in a photoresist composition, a photoresist can be provided that absorbs EUV photons while simultaneously having excellent etching resistance.

[0051] Therefore, the above organometallic compound can contribute to the production of ultra-fine semiconductor devices using EUV while implementing inorganic photoresist materials and technology.

[0052] Furthermore, to secure an EUV resist with high throughput and reduced shot noise, a central metal with high absorbance is required within the resist thin film. In other words, the introduction of a central metal capable of emitting a large number of secondary electrons through EUV absorption is necessary.

[0053] In this regard, the present invention provides a property that allows for the function of a photoresist having excellent etching resistance while absorbing EUV photons by introducing two different metal elements with excellent absorption efficiency into the structure of chemical formula 1.

[0054] Specifically, compared to ArF light sources, EUV light sources, which have higher energy, have a smaller number of photons per unit area. Consequently, the probability of shot noise increases, leading to the problem of forming non-uniform circuits. Therefore, the present invention overcomes the problem by introducing two specific elements with high light efficiency into the central metal portion of an organometallic compound, thereby improving the photon absorption rate of the EUV and minimizing shot noise as much as possible, thereby forming a uniform circuit or pattern.

[0055] These above organometallic compounds may contain two different types of metals at the center.

[0056] In addition, when the organometallic compound of the present invention has a linear or more-or-less cyclic structure containing two types of metals at the center so as not to be too bulky, the performance of absorbing EUV photons is optimized, and at the same time, it can function as a photoresist with excellent etching resistance. In this case, the metals in the present invention mean all of post-transition metals, metalloids, and non-metals.

[0057] Therefore, according to one embodiment of the invention, the organometallic compound and the solvent can be used as a photoresist composition even without including a separate resin. That is, the organometallic compound of the above chemical formula 1 can be used as a photoresist precursor material and, when applied to a photoresist composition (PR), can exhibit superior differences in physical properties compared to existing organic PR.

[0058] In addition, the organometallic compound of the above chemical formula 1 containing two or more different metal elements is advantageous in controlling nanoparticles and maximizing the dissolution rate ratio of the exposed / unexposed area, thereby being usable as a precursor in the formation of photoresist patterns to which various light sources such as ArF, KrF, and EUV are applied. In particular, the organometallic compound of the above chemical formula 1 is suitable for EUV.

[0059] Accordingly, the present invention can provide a material and method for forming nanoparticles for applying a spin coating method and a vapor deposition method when applying a photoresist including the organic compound of the above chemical formula 1 to a substrate.

[0060] More specifically, A and B are different elements, and A and B may each independently be elements selected from groups 2 to 17 or groups 13 to 17. In addition, A and B may each independently be any one of elements selected from groups 13 to 17, and elements of periods 5 and 6.

[0061] In a preferred embodiment, A and B may each be independently selected from the group consisting of Sn, Sb, In, Te, and I. However, A and B do not contain the same elements.

[0062] In one embodiment, A is Zr, In, Sn, Sb, or Hf, and B is Sn, Sb, In, Te, or I, provided that A and B do not contain the same elements.

[0063] For example, the above A may be Sn, Sb or In.

[0064] Additionally, the above B may be Te or I.

[0065] At this time, the above A and B are elements with high absorption efficiency, and when included in the center of the organometallic compound, they can improve the electron and photon absorption of EUV, thereby emitting a large amount of secondary electrons through EUV absorption. In addition, according to one embodiment, in the present invention, when different A and B are included, rather than when only one type of metal element is mainly included, the B element with better absorption efficiency than A can be used together to facilitate EUV photon absorption. The above A and B may be selected from elements of the 5th and 6th periods, and among them, B may be an element with higher absorption efficiency than A.

[0066] More specifically, when A is Sn or In and B is Te or I, the absorption efficiency can be further improved.

[0067]

[0068] Meanwhile, in the case where x≥1 and x1≥1 in the above chemical formula 1, y≥1 may be satisfied. In this case, the chemical formula 1 may include a linear or cyclic structure having one or more rings. In addition, in the case of the above conditions, a tetravalent organic group structure may be included in which metal A is bonded to both sides of the central metal B, and ligands that are the same or different are bonded to the remaining bonding hands of the central metal B to which metal A is not bonded.

[0069] In addition, when x≥1 and x1≥1 in the above chemical formula 1, y≥2 may be present. Accordingly, the above chemical formula 1 may have a cyclic structure of one or more rings.

[0070] The ligand connecting the A and B metals at the center of the above organometallic compound can provide a better effect the weaker the bond with the metal element.

[0071] In the present invention, L1 and L3 may be hydrolyzable ligands, L2 and L2' may be linking groups between metals, and R1 and R2 may be photoactive substituents.

[0072] The above L1 and L3 can each independently be an amino group, an amide group, an ether group, an ester group, or a combination thereof.

[0073] The above L2 and L2' may each independently be a direct bond, ether, -NH-, an alkylene having 1 to 5 carbon atoms, or a divalent organic group including a group 16 element. Specifically, the above L2 and L2' may each independently be a direct bond or an ether. When L2 and L2' are each independently a direct bond or an ether, the stability may be better.

[0074] More specifically, if the above chemical formula 1 is a cyclic structure, L2 and L2' may be direct bonds. If the above chemical formula 1 is a linear structure, L2 may be an ether and L2' may be a direct bond.

[0075] In addition, R1 and R2 may each independently be a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms. Specifically, R1 and R2 may each independently be a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms. More specifically, when R1 and R2 are each independently tert-butyl, they may exhibit better effects by separating well from the central metal. In particular, the tert-butyl group may cause a β-Hydrogen Elimination reaction better than when it is not a tert-butyl group, thereby further improving EUV photosensitivity.

[0076] In one embodiment of the invention, the chemical formula 1 may satisfy the condition of the following mathematical formula 1.

[0077] [Mathematical Formula 1]

[0078] 0 ≤ (a+c) / (n+m) ≤ 2

[0079] In the above mathematical formula 1, a, c, n, and m are as defined in the above chemical formula 1.

[0080] In another embodiment of the invention, the chemical formula 1 may satisfy the condition of the following mathematical formula 1.

[0081] [Mathematical Formula 1]

[0082] 0.5 ≤(a+c) / (n+m) ≤ 2

[0083] In the above mathematical formula 1, a, c, n, and m are as defined in the above chemical formula 1.

[0084] In the above chemical formula 1, b=0, b1=0. At this time, 1≤y≤4, 1≤x≤4, 1≤x1≤4, and specifically, x≥1. x1≥1, 1≤y≤2, and more specifically, x=1. x1=1, y=2.

[0085] As the above chemical formula 1 satisfies the conditions of the above mathematical formula 1, when there are many L ligands, the solubility is excellent when preparing a PR solution, and since there are many R substituents, there are many sites that can undergo photoreaction, making it easy to evaluate.

[0086] In a preferred embodiment of the invention, the compound represented by the chemical formula 1 may be any one of the compounds represented by the following chemical formula 2, chemical formula 3 or chemical formula 4.

[0087] [Chemical Formula 2]

[0088]

[0089] [Chemical Formula 3]

[0090]

[0091] [Chemical Formula 4]

[0092]

[0093] (In the above chemical formulas 2 to 4,

[0094] A and B are each independently an element selected from groups 2-17, and A and B are different elements,

[0095] R1 and R2 are the same or different from each other, and each independently represents 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, and R1 and R2 do not form a ring.

[0096] L1 and L3 are each independently hydrolyzable ligands,

[0097] L2 is independently a direct bond, ether, -NR3-, or an element selected from groups 14 to 17,

[0098] R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,

[0099] n, m and b are each independently integers from 1 to 10,

[0100] a, c, a' and c' are each independently integers from 0 to 5.)

[0101] The compound represented by the above chemical formula 2 may be one selected from the group consisting of the following. The compound of the above chemical formula 2 may be an example of a cyclic structure, including a case where x≥1, x1≥1, y≥1, or y≥2 in the chemical formula 1 as described above.

[0102]

[0103]

[0104]

[0105] The compound represented by the above chemical formula 3 may be one selected from the group consisting of:

[0106]

[0107]

[0108]

[0109]

[0110] The compound represented by the above chemical formula 4 may be one selected from the group consisting of the following. The compound of the above chemical formula 4 may be an example of a tetravalent organic group structure, including the cases where x≥1, x1≥1 and y≥1 in the chemical formula 1 as described above, or the cases where 1≤y≤4, 1≤x≤4, 1≤x1≤4 when b=0, b1=0 in the above chemical formula 1.

[0111]

[0112]

[0113] Meanwhile, specific examples of methods for synthesizing the above organometallic compound are not particularly limited, but for example, it can be synthesized through a nucleophilic substitution reaction in an organic solvent using a compound containing two different types of metals.

[0114] All reactions can be carried out in an inert atmosphere of nitrogen or argon.

[0115] The above reaction time may vary depending on the reactivity or reaction concentration, but may generally be 3 hours or more and 72 hours or less, and the reaction temperature may be -78°C or more and 150°C or less.

[0116] After the reaction is completed, the solution is filtered under reduced pressure to remove salts, and the solvent of the obtained solution is completely removed, and the solution can be purified using a single or combination of purification methods selected from among distillation, sublimation, recrystallization, etc.

[0117] In addition, another embodiment of the invention according to the present specification may provide a photoresist composition comprising an organometallic compound and a solvent.

[0118] In the present invention, the photoresist composition may be a semiconductor photoresist composition for EUV.

[0119] As described above, in the present invention, by introducing two types of metal components capable of emitting a large amount of secondary electrons through EUV absorption into the center of an organometallic compound and also including them to have a linear or more-or-less ring-shaped structure, it is possible to absorb EUV photons and simultaneously act as a photoresist having excellent etching resistance.

[0120] Therefore, it can be used as a photoresist composition even if it includes the organometallic compound and solvent without including a separate resin.

[0121] Accordingly, the present invention provides a semiconductor photoresist composition that satisfies basic photoresist performance while exhibiting excellent EUV photosensitivity and improved etching resistance. Furthermore, when a pattern is formed using the photoresist composition including the organometallic compound, a component with high absorbance is included in the resist thin film, thereby providing an EUV resist with high throughput and reduced shot noise.

[0122] In the photoresist composition of the present invention, the content of the organometallic compound may be 1 wt% or more and 10 wt% or less based on the entire photoresist composition. If the content of the organometallic compound is less than 1 wt%, there is a problem of performance improvement due to the low metal content, and if the content exceeds 10 wt%, an unnecessary process such as an etching process must be added to remove the metal.

[0123] As the organic solvent used in the present invention, any organic solvent used in a conventional photoresist composition that can dissolve the organometallic compound and additive of the above chemical formula 1 can be used without limitation. For example, ketones such as cyclohexanone and methyl amyl ketone, alcohols such as 2-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol, ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, and diethyl 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 mono tert-butyl ether acetate, lactones such as γ-butyrolactone Solvents may be used singly or in combination of two or more, but are not limited thereto. Examples of the organic solvents are not particularly limited, but for example, any one of PGMEA (propylene glycol monomethyl ether acetate), PGME (propylene glycol monomethyl ether), EL (ethyl lactate), and CyH (cyclohexanone), or a mixture thereof, which have the best solubility in acid diffusion inhibitors, may be used.

[0124] The content of the organic solvent may be the remainder of the photoresist composition excluding the organometallic compound of chemical formula 1, based on 100 wt% of the total photoresist composition.

[0125] In addition, if necessary, the photoresist composition may further include one or more additives selected from the group consisting of a photoacid generator, a light absorber, a crosslinking agent, a surfactant, and a leveling agent. The additive may be included in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the entire photoresist composition.

[0126] The types of the above additives are not particularly limited, as well-known ingredients in this field can be used. For example, photoacid generators include onium salt-based acid generators such as sulfonium salts or iodonium salts, diazomethane-based acid generators, oxime-based acid generators, nitrobenzylsulfonate-based acid generators, iminosulfonate-based acid generators, and disulfone-based acid generators. These may be used alone or in combination of two or more.

[0127] Additionally, it may further include alkaline-soluble resins used in general photoresist compositions, as needed.

[0128]

[0129] In addition, another embodiment of the invention according to the present specification may provide a pattern forming method including the steps of: forming a photoresist film by coating the photoresist composition on a substrate; exposing the photoresist film with an EUV light source; and developing the exposed photoresist film to form a photoresist pattern.

[0130] The content regarding the above photoresist composition includes the content described above with respect to the other embodiments.

[0131] The above coating method may be a coating method using a wet and / or dry process. The wet coating method may be spin coating, and the dry coating method may use CVD, ALD deposition, etc., but is not limited thereto.

[0132] The above pattern forming method can apply a known technology, for example, applying using a spinner or the like, exposing with EUV high-energy rays having a wavelength of 300 nm or less using a predetermined photomask, and developing the exposed photoresist film with a normal developer (for example, an alkaline aqueous solution such as an aqueous solution of tetramethylammonium hydroxide containing 0.1 wt% or more and 10 wt% or less).

[0133] Specifically, the pattern forming method can form a pattern by going through the steps of applying the above-described photoresist composition onto a silicon wafer substrate, heating the applied substrate to form a resist thin film, exposing the resist thin film using a selected high-energy exposure source, desorbing an acid labile group in a polymer resin by an acid generated at an exposed portion, and developing the resist thin film, the solubility of which has been changed, with the developer.

[0134] Optionally, the photoresist composition can form a pattern with excellent performance even when a high-energy ray having a general wavelength of 300 nm or less is applied as an exposure light source in addition to the extreme ultraviolet (EUV) light. For example, the high-energy ray having a wavelength of 300 nm or less may be ultraviolet, ultraviolet, electron, X-ray, excimer laser, γ-ray, or synchrotron radiation.

[0135] In addition, for forming fine patterns of 70 nm or less, it is preferable to use an exposure device equipped with a source of high-energy short-wavelength rays such as an ArF excimer laser, a KrF excimer laser, or an EUV.

[0136] The above substrate can be a circular silicon wafer with a diameter of 8 or 12 inches, which can be used as a substrate for thin film deposition.

[0137] More specifically, the high-energy light source may be EUV with a wavelength of 13.5 nm, and may be selected from KrF with a wavelength of 248 nm, ArF with a wavelength of 193 nm, or electron beam (e-beam) as needed.

[0138] In addition, the above photoresist pattern can be formed into a thin film pattern by performing an etching process using a well-known method.

[0139] The photoresist pattern formed by the above method may have a line width of 5 to 100 nm and a line width roughness of 50 nm or less. In addition, the photoresist pattern may have a line width of 5 to 50 nm and a line width roughness of 10 nm or less.

[0140]

[0141] Hereinafter, examples are presented to aid understanding of the invention. However, the following examples are intended only to illustrate the invention and are not intended to limit the invention to these examples.

[0142]

[0143] Synthetic Examples 1 to 26: Preparation of a compound represented by Chemical Formula 1

[0144] <Synthesis Example 1> Synthesis of a compound represented by Chemical Formula 5

[0145] [Chemical Formula 5]

[0146]

[0147] A 500 ml round-bottomed flask was wrapped with aluminum foil to completely block out light, and 230.0 g (0.04 mol) of [(Dimethylamine)2-Sn-Te] was added. Then, 300 ml of anhydrous tetrahydrofuran was added and stirred for 1 hour. The temperature of the reactor was lowered to -20°C. t 10.5 g (0.09 mol) of BuMgCl (1.0 M in THF) was slowly added. After the addition was completed, the temperature was gradually increased and the mixture was stirred at room temperature for 8 hours to complete the reaction. After this, the resulting reaction solution was filtered under reduced pressure to remove salts, and the solvent in the resulting solution was completely removed to obtain the compound represented by the chemical formula 5 in a yield of 72%.

[0148] 1 H-NMR (C6D6): δ 1.34 (s, 18H), δ 2.42 (s, 12H).

[0149]

[0150] <Synthesis Example 2> Synthesis of a compound represented by chemical formula 6

[0151] [Chemical Formula 6]

[0152]

[0153] In the above Synthesis Example 2, except that [(t-butoxide)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2, the compound represented by the chemical formula 6 was obtained in a yield of 69% by synthesizing in the same manner as in the above Synthesis Example 1.

[0154] 1 H-NMR (C6D6): δ 1.27 (t, 18H), δ 1.32 (s, 18H).

[0155]

[0156] <Synthesis Example 3> Synthesis of a compound represented by chemical formula 7

[0157] [Chemical Formula 7]

[0158]

[0159] In the above Synthesis Example 3, except that [(Propionate)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2, the compound represented by the chemical formula 7 was obtained in a yield of 75% by synthesizing in the same manner as in the above Synthesis Example 1.

[0160] 1 H-NMR (C6D6): δ 1.04 (t, 6H), δ 1.41 (s, 18H), δ 2.31 (q, 4H).

[0161]

[0162] <Synthesis Example 4> Synthesis of a compound represented by chemical formula 8

[0163] [Chemical Formula 8]

[0164]

[0165] Wrap a 250ml round flask with aluminum foil to completely block out light, ( t Bu)2Sn(Dimethylamine)Cl 10.0 g (0.03 mol) was added. After that, 100 ml of anhydrous tetrahydrofuran was added, the temperature of the reactor was lowered to -20°C, and 4.8 g (0.03 mol) of NaI was slowly added. After the addition was completed, the temperature was gradually increased and refluxed for 8 hours to complete the reaction. After that, the obtained reaction product solution was filtered under reduced pressure to remove salts, and the solvent of the obtained solution was completely removed to obtain the compound represented by the above chemical formula 8 in a yield of 68%.

[0166] 1 H-NMR (C6D6): δ 1.40 (s, 36H), δ 2.47 (s, 12H).

[0167]

[0168] <Synthesis Example 5> Synthesis of a compound represented by chemical formula 9

[0169] [Chemical Formula 9]

[0170]

[0171] In the above synthesis example 5, ( t Instead of Bu)2Sn(Dimethylamine)Cl ( t Except for using Bu)2Sn(t-botoxide)Cl, the compound represented by the chemical formula 9 was obtained in a yield of 75% by the same method as in Synthesis Example 4.

[0172] 1 H-NMR (C6D6): δ 1.24 (t, 18H), δ 1.31 (s, 36H).

[0173]

[0174] <Synthesis Example 6> Synthesis of a compound represented by chemical formula 10

[0175] [Chemical Formula 10]

[0176]

[0177] In the above synthesis example 6, ( t Instead of Bu)2Sn(Dimethylamine)Cl ( t Except for using Bu)2Sn(Propionate)Cl, the compound represented by the chemical formula 10 was obtained in a yield of 79% by the same method as in Synthesis Example 4.

[0178] 1 H-NMR (C6D6): δ 1.05 (t, 6H), δ 1.37 (s, 36H), δ 2.31 (q, 4H).

[0179]

[0180] <Synthesis Example 7> Synthesis of a compound represented by chemical formula 11

[0181] [Chemical Formula 11]

[0182]

[0183] In the above synthesis example 7, [(t-butoxide)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2. t A compound represented by the chemical formula 11 was obtained in a yield of 78% by the same method as in Synthesis Example 1, except that MeMgCl was used instead of BuMgCl.

[0184] 1 H-NMR (C6D6): δ 0.62 (s, 6H), δ 1.18 (s, 18H).

[0185]

[0186] <Synthesis Example 8> Synthesis of a compound represented by chemical formula 12

[0187] [Chemical Formula 12]

[0188]

[0189] In the above synthesis example 8, [(t-butoxide)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2. tA compound represented by the chemical formula 12 was obtained in a yield of 72% by the same method as in Synthesis Example 1, except that PhMgBr was used instead of BuMgCl.

[0190] 1 H-NMR (C6D6): δ 1.42 (s, 18H), δ 7.33 (m, 10H).

[0191]

[0192] <Synthesis Example 9> Synthesis of a compound represented by chemical formula 13

[0193] [Chemical Formula 13]

[0194]

[0195] In the above synthesis example 9, [(Propionate)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2. t A compound represented by the chemical formula 13 was obtained in a yield of 74% by the same method as in Synthesis Example 1, except that MeMgCl was used instead of BuMgCl.

[0196] 1 H-NMR (C6D6): δ 0.71 (s, 6H), δ 1.07 (t, 6H), δ 2.24 (q, 4H).

[0197]

[0198] <Synthesis Example 10> Synthesis of a compound represented by chemical formula 14

[0199] [Chemical Formula 14]

[0200]

[0201] In the above synthesis example 10, [(Propionate)2-Sn-Te]2 was used instead of [(Dimethylamine)2-Sn-Te]2. t A compound represented by the chemical formula 14 was obtained in a yield of 68% by the same method as in Synthesis Example 1, except that PhMgBr was used instead of BuMgCl.

[0202] 1 H-NMR (C6D6): δ 1.13 (t, 6H), δ 2.32 (q, 4H), δ 7.32 (m, 10H).

[0203]

[0204] <Synthesis Example 11> Synthesis of a compound represented by Chemical Formula 15

[0205] [Chemical Formula 15]

[0206]

[0207] In the above synthesis example 11, ( t Except for using (Me)2Sn(Propionate)Cl instead of (Bu)2Sn(Dimethylamine)Cl, the compound represented by the chemical formula 15 was obtained in a yield of 75% by the same method as in Synthesis Example 4.

[0208] 1 H-NMR (C6D6): δ 0.61 (s, 12H), δ 1.04 (t, 6H), δ 2.38 (q, 4H).

[0209]

[0210] <Synthesis Example 12> Synthesis of a compound represented by chemical formula 16

[0211] [Chemical Formula 16]

[0212]

[0213] In the above synthesis example 12, ( t Except for using (Me)Sn(Propionate)2Cl instead of Bu)2Sn(Dimethylamine)Cl, the compound represented by the chemical formula 16 was obtained in a yield of 78% by the same method as in Synthesis Example 4.

[0214] 1 H-NMR (C6D6): δ 0.62 (s, 6H), δ 1.09 (t, 12H), δ 2.42 (q, 8H).

[0215]

[0216] <Synthesis Example 13> Synthesis of a compound represented by chemical formula 17

[0217] [Chemical Formula 17]

[0218]

[0219] In the above synthesis example 13, ( t Instead of Bu)2Sn(Dimethylamine)Cl ( t Except for using Bu)In(Dimethylamine)Cl, the compound represented by the chemical formula 17 was obtained in a yield of 71% by the same method as in Synthesis Example 4.

[0220] 1 H-NMR (C6D6): δ 1.22 (s, 18H), δ 2.47 (s, 12H).

[0221]

[0222] <Synthesis Example 14> Synthesis of a compound represented by chemical formula 18

[0223] [Chemical Formula 18]

[0224]

[0225] In the above synthesis example 14, ( t Instead of Bu)2Sn(Dimethylamine)Cl ( t Except for using Bu)In(t-butoxide)Cl, the compound represented by the chemical formula 18 was obtained in a yield of 78% by the same method as in Synthesis Example 4.

[0226] 1 H-NMR (C6D6): δ 1.32 (s, 18H), δ 1.49 (s, 18H).

[0227]

[0228] <Synthesis Example 15> Synthesis of a compound represented by chemical formula 19

[0229] [Chemical Formula 19]

[0230]

[0231] In the above synthesis example 15, ( t Instead of Bu)2Sn(Dimethylamine)Cl ( t Except for using Bu)In(Propionate)Cl, the compound represented by the chemical formula 19 was obtained in a yield of 73% by the same method as in Synthesis Example 4.

[0232] 1 H-NMR (C6D6): δ 1.05 (t, 6H), δ 1.41 (s, 18H), δ 2.27 (q, 4H).

[0233]

[0234] <Synthesis Example 16> Synthesis of a compound represented by chemical formula 20

[0235] [Chemical Formula 20]

[0236]

[0237] Wrap a 500ml round flask with aluminum foil to completely block out light. t 320.0 g (0.06 mol) of BuSn(Dimethylamine) was added. After that, 300 ml of anhydrous tetrahydrofuran was added and the temperature of the reactor was lowered to -20°C. t After adding 320.6 g (0.06 mol) of BuTe(Dimethylamine) and 1.2 g (0.06 mol) of H2O, the mixture was heated and stirred at room temperature for 18 hours. Afterwards, the resulting reaction solution was filtered under reduced pressure to remove salts, and the solvent in the resulting solution was completely removed to obtain a compound represented by the chemical formula 20 in a yield of 76%.

[0238] 1 H-NMR (C6D6): δ 1.28 (s, 9H), δ 1.33 (s, 9H), δ 2.43 (s, 12H), δ 2.52 (s, 12H).

[0239]

[0240] <Synthesis Example 17> Synthesis of a compound represented by chemical formula 21

[0241] [Chemical Formula 21]

[0242]

[0243] In the above synthesis example 17, t Instead of BuSn(Dimethylamine)3 t Using BuSn(t-butoxide)3, t Instead of BuTe(Dimethylamine)3 t Except for using BuTe(t-butoxide)3, the compound represented by the chemical formula 21 was obtained in a yield of 73% by the same method as in Synthesis Example 16.

[0244] 1 H-NMR (C6D6): δ 1.18 (s, 9H), δ 1.21 (s, 9H), δ 1.25 (s, 18H), δ 1.29 (s, 18H).

[0245]

[0246] <Synthesis Example 18> Synthesis of a compound represented by chemical formula 22

[0247] [Chemical Formula 22]

[0248]

[0249] In the above synthesis example 18, t Instead of BuSn(Dimethylamine)3 t Using BuSn(Propionate)3, t Instead of BuTe(Dimethylamine)3 t Except for using BuTe(Propionate)3, the compound represented by the chemical formula 22 was obtained in a yield of 63% by the same method as in Synthesis Example 16.

[0250] 1 H-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).

[0251]

[0252] <Synthesis Example 19> Synthesis of a compound represented by chemical formula 23

[0253] [Chemical Formula 23]

[0254]

[0255] In the above synthesis example 19, t Use MeSn(Dimethylamine)3 instead of BuSn(Dimethylamine)3, t Except that MeTe(Dimethylamine)3 was used instead of BuTe(Dimethylamine)3, the compound represented by the chemical formula 23 was obtained in a yield of 79% by the same method as in Synthesis Example 16.

[0256] 1 H-NMR (C6D6): δ 0.56 (s, 3H), δ 0.64 (s, 3H), δ 2.46 (s, 12H), δ2.52 (s, 12H).

[0257]

[0258] <Synthesis Example 20> Synthesis of a compound represented by chemical formula 24

[0259] [Chemical Formula 24]

[0260]

[0261] In the above synthesis example 20, t Use PhSn(Dimethylamine)3 instead of BuSn(Dimethylamine)3, t Except for using PhTe(Dimethylamine)3 instead of BuTe(Dimethylamine)3, the compound represented by the chemical formula 24 was obtained in a yield of 73% by the same method as in Synthesis Example 16.

[0262] 1 H-NMR (C6D6): δ 2.38 (s, 12H), δ2.54 (s, 12H), δ7.42 (m, 5H), δ7.58 (m, 5H).

[0263]

[0264] <Synthesis Example 21> Synthesis of a compound represented by chemical formula 25

[0265] [Chemical Formula 25]

[0266]

[0267] In the above Synthesis Example 21, except that H2S was used instead of H2O, the compound represented by the above Chemical Formula 25 was obtained in a yield of 69% by synthesizing in the same manner as in the above Synthesis Example 16.

[0268] 1 H-NMR (C6D6): δ 1.33 (s, 9H), δ 1.36 (s, 9H), δ 2.25 (s, 12H), δ 2.38 (s, 12H).

[0269]

[0270] <Synthesis Example 22> Synthesis of a compound represented by chemical formula 26

[0271] [Chemical Formula 26]

[0272]

[0273] In the above Synthesis Example 22, except that H2Se was used instead of H2O, the compound represented by the above Chemical Formula 26 was obtained in a yield of 71% by synthesizing in the same manner as in the above Synthesis Example 16.

[0274] 1 H-NMR (C6D6): δ 1.22 (s, 9H), δ 1.31 (s, 9H), δ 2.18 (s, 12H), δ 2.41 (s, 12H).

[0275]

[0276] <Synthesis Example 23> Synthesis of a compound represented by chemical formula 27

[0277] [Chemical Formula 27]

[0278]

[0279] In the above Synthesis Example 23, except that NH3 was used instead of H2O, the compound represented by the chemical formula 27 was obtained in a yield of 74% by synthesizing in the same manner as in the above Synthesis Example 16.

[0280] 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).

[0281]

[0282] <Synthesis Example 24> Synthesis of a compound represented by chemical formula 28

[0283] [Chemical Formula 28]

[0284]

[0285] In the above Synthesis Example 24, except that CH4 was used instead of H2O, the compound represented by the chemical formula 28 was obtained in a yield of 68% by synthesizing in the same manner as in the above Synthesis Example 16.

[0286] 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).

[0287]

[0288] <Synthesis Example 25> Synthesis of a compound represented by chemical formula 29

[0289] [Chemical Formula 29]

[0290]

[0291] A 500 ml round flask with a stem was wrapped with aluminum foil to completely block out light, and 220.0 g (0.05 mol) of [Sn-(Dimethylamine)2] was added. Then, 300 ml of anhydrous tetrahydrofuran was added and stirred for 1 hour. The temperature of the reactor was lowered to -20°C and [ tBu-Te]235.7 g (0.10 mol) was slowly added. After the addition was completed, the temperature was gradually increased and the reaction was completed by stirring at room temperature for 18 hours. After this, the resulting reaction product solution was filtered under reduced pressure to remove salts, and the solvent of the resulting solution was completely removed to obtain the compound represented by the chemical formula 29 in a yield of 69%.

[0292] 1 H-NMR (C6D6): δ 1.40 (s, 18H), δ 2.39 (s, 12H).

[0293]

[0294] <Synthesis Example 26> Synthesis of a compound represented by chemical formula 30

[0295] [Chemical Formula 30]

[0296]

[0297] A 500 ml round-bottomed flask was wrapped with aluminum foil to completely block out light, and 15.0 g (0.03 mol) of [Chemical Formula 29] was added. 300 ml of anhydrous tetrahydrofuran was then added and stirred. The temperature of the reactor was lowered to -20°C, and 3.9 g (0.05 mol) of propionic acid was slowly added. After the addition was complete, the temperature was gradually increased and the mixture was stirred at room temperature for 18 hours to complete the reaction. The resulting reaction product solution was filtered under reduced pressure to remove salts, and the solvent in the resulting solution was completely removed to obtain the compound represented by the chemical formula 30 in a yield of 83%.

[0298] 1 H-NMR (C6D6): δ 1.15 (t, 6H), δ 1.43 (s, 18H), δ 2.33 (q, 4H).

[0299]

[0300] <Examples 1 to 26>

[0301] Compounds represented by chemical formulas 5 to 30 synthesized in Synthetic Examples 1 to 26 were dissolved in PGMEA at a concentration of 2 wt%, mixed, and then filtered to prepare a composition for semiconductor photoresist. An 8-inch diameter circular silicon wafer having a native-oxide surface was used as a substrate for thin film deposition.

[0302] The semiconductor photoresist composition according to Examples 1 to 26 was spin-coated on the pretreated substrate at 1,500 rpm for 30 seconds, and baked on a hot plate at 180° C. for 120 seconds to form a thin film.

[0303]

[0304] <Comparative Examples 1 and 2>

[0305] A photoresist composition and a thin film pattern were formed in the same manner as in Example 1, except that the compounds of Comparative Compound 1 and Comparative Compound 2 in Table 1 below were used instead of the compound represented by Chemical Formula 5 as the organometallic compound.

[0306] Comparative compound 1 Comparative compound 2 Sn3(dmamp)4Se4 (dmamp is 1-dimethylamino-2-methyl-2-propanolate)

[0307] <Experimental Example> The exposure characteristics of the resist pattern were evaluated using the following method, and the results are shown in Table 2.

[0308]

[0309] (1) Coating property evaluation

[0310] The thickness of the thin film after coating and baking the compounds represented by chemical formulas 5 to 30 was measured using ellipsometry, and the measured thickness was approximately 10-50 nm.

[0311] Coating standard

[0312] The number of defects was measured using SP-5 equipment, and the coating evaluation criteria are as follows.

[0313] ○: Number of defects: 5 or less

[0314] X: Number of defects exceeds 5

[0315]

[0316] (2) Sensitivity

[0317] The thin films of Examples 1 to 26 and Comparative Examples 1 to 2, coated and baked with the compounds represented by the above chemical formulas 5 to 30 and Comparative Compounds 1 and 2, were exposed to EUV radiation. After exposure, they were baked at 170°C for 120 seconds (post-exposure bake, PEB). The baked thin films were immersed in a developer and washed to form negative tone images. The residual resist thickness was measured using an ellipsometer, and D was determined for each type of resist. g (Does to gel) is shown in Table 2 below. It can be confirmed that the pattern formed using the composition for semiconductor photoresist exhibits superior sensitivity compared to when only a single high-absorbing element was used (comparative example).

[0318]

[0319] Organometallic compound coating sensitivity (mJ / cm) 2) Example 1 Synthesis Example 1 [Chemical Formula 5] ○ 13.652 Synthesis Example 2 [Chemical Formula 6] ○ 13.413 Synthesis Example 3 [Chemical Formula 7] ○ 13.584 Synthesis Example 4 [Chemical Formula 8] ○ 13.105 Synthesis Example 5 [Chemical Formula 9] ○ 13.246 Synthesis Example 6 [Chemical Formula 10] ○ 13.227 Synthesis Example 7 [Chemical Formula 11] ○ 13.358 Synthesis Example 8 [Chemical Formula 12] ○ 13.379 Synthesis Example 9 [Chemical Formula 13] ○ 13.2610 Synthesis Example 10 [Chemical Formula 14] ○ 13.3311 Synthesis Example 11 [Chemical Formula 15] ○ 13.1112 Synthesis Example 12 [Chemical Formula 16] ○ 13.0813 Synthesis Example 13 [Chemical Formula 17] ○ 13.2314 Synthesis Example 14 [Chemical Formula 18] ○ 13.3215 Synthesis Example 15 [Chemical Formula 19] ○13.1816Synthesis Example 16 [Chemical Formula 20] ○14.1217Synthesis Example 17 [Chemical Formula 21] ○14.1618Synthesis Example 18 [Chemical Formula 22] ○14.0519Synthesis Example 19 [Chemical Formula 23] ○14.2320Synthesis Example 20 [Chemical Formula 24] ○14.3121Synthesis Example 21 [Chemical Formula 25] ○14.1322Synthesis Example 22 [Chemical Formula 26] ○14.1923Synthesis Example 23 [Chemical Formula 27] ○14.2024Synthesis Example 24 [Chemical Formula 28] ○14.1325Synthesis Example 25 [Chemical Formula 29] ○13.8926Synthesis Example 26 [Chemical Formula 30] ○13.72Comparative Example 1 [Comparative Compound 1] ○15.032 [Comparative Compound 2] XCannot be evaluated

[0320] As shown in Table 2 above, Examples 1 to 26, by using organometallic compounds of chemical formulas 5 to 30 having two different metals, exhibited superior coating properties and sensitivity characteristics compared to the comparative examples using comparative compounds 1 and 2 containing only a single metal. In addition, among the organometallic compounds of chemical formulas 5 to 30, the cyclic type may have a relatively better effect than the chain type due to the greater number of elements contained in one molecule. In contrast, even when only a single metal is contained, Comparative Example 1 using Comparative Compound 1 had poorer sensitivity than the examples even though it had good coating properties. In addition, Comparative Compound 2 did not have an alkyl chain that could photoreact during EUV evaluation and was unstable in the air, making coating impossible. As a result, exposure evaluation of Comparative Example 2 was impossible.

Claims

1. An organometallic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A and B are each independently an element selected from groups 2 to 17, and A and B are different elements, R 1 and R 2 are the same or different from each other, and each independently represents 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, and R 1 and R 2 They do not form rings with each other, L 1 and L 3 are independently hydrolyzable ligands, and L 2 , and L 2 ' are each independently a direct bond, ether, secondary amine, alkylene or an element selected from groups 14 to 17, x, y, n, and m are each independently integers from 1 to 10, a, c, x 1 , b, a', c' and b 1 are each independently an integer from 0 to 5.

2. In paragraph 1, The above A and B are each independently an organometallic compound selected from the group consisting of Sn, Sb, In, Te, or I.

3. In paragraph 1, An organometallic compound wherein A is Zr, In, Sn, Sb, or Hf, and B is Sn, Sb, In, Te, or I, provided that A and B do not contain the same elements.

4. In paragraph 1, An organometallic compound wherein A is Sn, Sb or In, and B is Te or I.

5. In paragraph 1, In the chemical formula 1 above, x≥1, x 1 Organometallic compounds where y≥1 if ≥1.

6. In paragraph 1, In the chemical formula 1 above, x≥1, x 1 Organometallic compounds where y≥2 if ≥1.

7. In paragraph 1, Above R 1 and R 2 An organometallic compound, wherein each independently represents a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 3 to 10 carbon atoms.

8. In paragraph 1, Above L 1 and L 3 An organometallic compound, each independently selected from the group consisting of an amino group, an amide group, an ether group, an ester group, or a combination thereof.

9. In paragraph 1, Above L 2 , and L 2 ' are organometallic compounds which are each independently direct bonds or ethers.

10. In paragraph 1, The above chemical formula 1 is an organometallic compound satisfying the following conditions: [Mathematical Formula 1] 0 ≤ (a+c) / (n+m) ≤ 2 In the above mathematical formula 1, a, c, n, and m are as defined in the above chemical formula 1.

11. In paragraph 1, In the chemical formula 1 above, b=0, b 1 =0 organometallic compound.

12. In paragraph 1, The compound represented by the above chemical formula 1 is an organometallic compound which is one of the compounds represented by the following chemical formula 2, chemical formula 3 or chemical formula 4: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, A and B are each independently an element selected from groups 2-17, and A and B are different elements, R 1 and R 2 are the same or different from each other, and each independently represents 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, and R 1 and R 2 They do not form rings, L 1 and L 3 are independently hydrolyzable ligands, L 2 are each independently a direct bond, ether, -NR 3 -, or an element selected from groups 14 to 17, R 3 is hydrogen or an alkyl group having 1 to 5 carbon atoms, n, m and b are each independently an integer from 1 to 10, a, c, a', and c' are each independently integers from 0 to 5.

13. In paragraph 12, The compound represented by the above chemical formula 2 is an organometallic compound, which is one selected from the group consisting of:

14. In paragraph 12, The compound represented by the above chemical formula 3 is an organometallic compound, which is one selected from the group consisting of:

15. In paragraph 12, The compound represented by the above chemical formula 4 is an organometallic compound, which is one selected from the group consisting of:

16. A photoresist composition comprising the organometallic compound of paragraph 1 and a solvent.

17. In paragraph 16, A photoresist composition comprising the organometallic compound in an amount of 1 wt% or more and 10 wt% or less relative to the entire photoresist composition.

18. In paragraph 16, A photoresist composition further comprising at least one additive selected from the group consisting of a photoacid generator, a light absorber, a crosslinking agent, a surfactant, and a leveling agent.

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