Semiconductor photoresist composition and method of forming pattern using the same

Abstract

A semiconductor photoresist composition includes an organometallic compound represented by Chemical Formula 1 and a solvent. A method of forming (or providing) a pattern using the semiconductor photoresist composition is provided. [Chemical Formula 1] (R1) n1-M-[(X)-R2] m1.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0102400 filed in the Korean Intellectual Property Office on August 4, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a semiconductor photoresist composition and a method of forming (or providing) a pattern using the semiconductor photoresist composition. Background Art

[0004] Extreme ultraviolet (EUV) lithography has been regarded as a technology (e.g., a key technology) for manufacturing next-generation semiconductor devices. EUV lithography is a pattern forming (or providing) technology using EUV rays having a wavelength of about 13.5 nanometers (nm) as an exposure source. By using EUV lithography, a very fine pattern (e.g., less than or equal to about 20 nm) can be formed in an exposure process during a manufacturing process of a semiconductor device.

[0005] Extreme ultraviolet (EUV) lithography is achieved through the development of compatible photoresists that can be performed with a spatial resolution of less than or equal to about 16 nm. Currently, efforts are being pursued to address the insufficient specifications of traditional chemically amplified (CA) photoresists for next generation devices, such as those related to resolution, photospeed, and / or feature roughness (or also known as line edge roughness or LER).

[0006] Intrinsic image blurring due to acid-catalyzed reactions in these polymer types or classes of photoresists can limit resolution of small feature sizes, as has long been known in electron beam (e-beam) lithography. Chemically amplified (CA) photoresists are designed to achieve relatively high sensitivity, but may have more difficulty with EUV exposure in part because their typical elemental makeup reduces the absorbance of the photoresist at a wavelength of about 13.5 nm and therefore reduces its sensitivity.

[0007] In addition, CA photoresists may have difficulty with small feature sizes due to roughness issues, and it has been demonstrated in experiments that the line edge roughness (LER) of CA photoresists increases as photospeed decreases, at least in part due to the nature (e.g., inherent characteristics) of the acid catalyst process. Therefore, due to these defects and problems of CA photoresists, a novel relatively high performance photoresist is desired or needed in the semiconductor industry.

[0008] In order to overcome the above-mentioned disadvantages of chemically amplified (CA) organic photosensitive compositions, an inorganic photosensitive composition has been developed. The inorganic photosensitive composition, which resists removal by a developer composition due to chemical modification by a non-chemical amplification mechanism, is mainly used for negative patterning. The inorganic composition contains an inorganic element having a higher EUV absorption rate than hydrocarbons, and thus can ensure appropriate sensitivity by a non-chemical amplification mechanism. In addition, the inorganic composition is less sensitive to stochastic effects, and thus can have relatively low line edge roughness and a small number of defects.

[0009] Inorganic photoresists based on peroxypolyacids of tungsten mixed with tungsten, niobium, titanium and / or tantalum have been reported as radiation-sensitive materials for patterning (see also US 5061599 as an example; and H. Okamoto, T. Iwayanagi, K. Mochiji, H. Umezaki, T. Kudo, Applied Physics Letters, 49(5), 298-300, 1986; the entire contents of each of the two examples are incorporated herein by reference).

[0010] These materials are used as effectively as extreme ultraviolet (deep UV), X-ray and electron beam sources for patterning large pitches of bilayer configurations. Recently, suitable performance has been obtained when cationic hafnium metal oxide sulfate (HfSOx) materials are used with peroxo complexing agents for imaging 15nm half-pitch (HP) by projection EUV exposure. (See also, for example, US2011-0045406; and JK Stowers, A. Telecky, M. Kocsis, BL Clark, DA Keszler, A. Grenville, CN Anderson, PP Naulleau, Proc. SPIE, 7969, 796915, 2011, the entire contents of each of the two examples are incorporated herein by reference). This system / process exhibits better performance as a non-CA photoresist and has a feasible photosensitivity approaching the requirements of EUV photoresists. However, hafnium metal oxide sulfate materials with peroxy complexing agents have some practical disadvantages. First, these materials are applied in the form of a corrosive sulfuric acid / hydrogen peroxide mixture and the shelf life stability may be insufficient. Second, as a composite mixture, it is not easy to structurally modify it to achieve improved performance. Third, development is (e.g., should be) carried out in a relatively high (e.g., very high) concentration of tetramethylammonium hydroxide (TMAH) solution and / or similar solutions of about 25% by weight. Summary of the invention

[0011] Aspects according to some embodiments relate to a semiconductor photoresist composition exhibiting excellent or suitable sensitivity and improved stability.

[0012] Aspects according to some embodiments relate to a method of forming (or providing) a pattern using the semiconductor photoresist composition.

[0013] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from reading the description, or may be learned by practice of the presented embodiments of the disclosure.

[0014] Recently, tin-containing molecules (e.g., materials) have been actively studied, which have excellent or suitable absorption of extreme ultraviolet rays. For organotin polymers, alkyl ligands are dissociated by light absorption or secondary electrons generated therefrom, and cross-linked with adjacent chains through oxygen bonds, thereby enabling negative patterning that can not be removed by organic developers. Such organotin polymers show greatly improved sensitivity and maintain suitable resolution and line edge roughness, but for commercial availability, additional improvements in patterning characteristics are required.

[0015] According to some embodiments, a semiconductor photoresist composition includes an organometallic compound represented by Chemical Formula 1 and a solvent.

[0016] [Chemical formula 1]

[0017] (R 1 ) n1 -M-[(X)-R 2 ] m1

[0018] In Chemical Formula 1,

[0019] M is a tetravalent metal, a pentavalent metal or a hexavalent metal,

[0020] R 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or L a -OR a (Among them, L a is a substituted or unsubstituted C1 to C20 alkylene group, and R a is a substituted or unsubstituted C1 to C20 alkyl group),

[0021] R 2 is tert-butyl, benzoyl, pivaloyl, acetyl, tert-butyldiphenylsilyl, tert-butyldimethylsilyl, allyl, tetrahydropyranyl, methoxymethyl, benzyl ether, tert-butyl ether, p-toluenesulfonyl, 2-phenylvinyl, benzyl, trifluoromethyl, benzyl ester, tert-butyl ester, 9-fluorenylmethyl or triphenylmethyl,

[0022] X is O-[L 1 -O] n2 (Where L 1is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, and n2 is an integer selected from 0 to 10), OC(O)-[L 2 -C(O)O] n3 (Where L 2 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, and n3 is an integer selected from 0 to 10), N(R 3 )-[L 3 -N(R 4 )] n4 (Among them, L 3 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 3 and R 4 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n4 is an integer selected from 0 to 10), N(R 5 )C(O)-[L 4 -N(R 6 )C(O)] n5 (Where L 4 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 5 and R 6 (R) are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n5 is an integer selected from 0 to 10), or N(R 7 )CN(R 8 )-[L 5 -N(R 9 )CN(R 10 )] n6 (Where L 5 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 7 to R 10may each independently be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n6 is an integer selected from 0 to 10),

[0023] n1 and m1 may each independently be an integer selected from 1 to 5, and

[0024] 4≤n1+m1≤6.

[0025] In some embodiments, M may be one selected from Sn, Sb, I, Te, In, Ag, Ni, Bi, and Po.

[0026] In some embodiments, M may be Sn.

[0027] In some embodiments, R 1 It may be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or L a -OR a (Where L a may be a substituted or unsubstituted C1 to C10 alkylene group, and R a may be a substituted or unsubstituted C1 to C10 alkyl group), and

[0028] X can be O, OC(O), N(R 3 )(where R 3 may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C6 to C20 aryl, or (for example, any suitable) combination thereof), N(R 5 )C(O)(where R 5 may be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof (e.g., any suitable combination), or N(R 7 )CN(R 8 )(where R 7 and R 8They may each independently be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or (for example, any suitable) combination thereof).

[0029] In some embodiments, R 1 The radicals may be methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valeryl, ethoxy, propoxy, or a combination thereof (e.g., any suitable one).

[0030] In some embodiments, R 3 to R 10 Each may independently be hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, or a combination thereof (e.g., any suitable combination).

[0031] In some embodiments, the organometallic compound may be one selected from the compounds listed in Group 1.

[0032] [Group 1]

[0033]

[0034]

[0035]

[0036] In some embodiments, the organometallic compound may be included in an amount of about 1 wt % to about 30 wt % based on 100 wt % of the semiconductor photoresist composition.

[0037] In some embodiments, the semiconductor photoresist composition may further include an additive selected from a surfactant, a cross-linking agent, a leveling agent, and (eg, any suitable) combination of the agents.

[0038] In some embodiments, a method for forming (or providing) a pattern includes: forming (or providing) an etching target layer on a substrate; coating the semiconductor photoresist composition on the etching target layer to form (or provide) a photoresist layer; patterning the photoresist layer to form (or provide) a photoresist pattern; and etching the etching target layer using the photoresist pattern as an etching mask.

[0039] In some embodiments, the photoresist pattern may be formed using light having a wavelength of about 5 nm to about 150 nm.

[0040] In some embodiments, the method of forming (or providing) a pattern may further include providing a resist bottom layer between the substrate and the photoresist layer.

[0041] In some embodiments, the photoresist pattern may have a width of about 5 nm to about 100 nm.

[0042] The semiconductor photoresist composition according to some embodiments may provide a photoresist pattern having improved storage stability, moisture stability, and sensitivity. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:

[0044] Figures 1 to 5 is a cross-sectional view for explaining a method of forming (or providing) a pattern using a semiconductor photoresist composition according to some embodiments.

[0045] [Explanation of Reference Numerals]

[0046] 100: Substrate

[0047] 102: Film

[0048] 104: Resist base

[0049] 106: Photoresist layer

[0050] 106a: Unexposed area

[0051] 106b: Exposure area

[0052] 108: Photoresist pattern

[0053] 110: Patterned mask

[0054] 112: Organic layer pattern

[0055] 114: Thin film pattern DETAILED DESCRIPTION

[0056] In the following, embodiments of the present disclosure are described in more detail with reference to the accompanying drawings. In the following description of the present disclosure, in order to clarify the present disclosure, functions or structures known in the relevant field will not be described in detail.

[0057] Throughout the present disclosure, the same or similar configuration elements are indicated by the same reference numerals. In addition, since the size and thickness of each configuration shown in the drawings are arbitrarily shown for better understanding and ease of description, the present disclosure is not necessarily limited thereto.

[0058] In the accompanying drawings, the thickness of each layer, film, panel, region and / or the like may be exaggerated for clarity. In the accompanying drawings, the thickness of a portion of each layer or region and / or the like may be exaggerated for clarity. It should be understood that if an element (e.g., a layer, film, region, or substrate) is referred to as being "on" another element (e.g., when an element (e.g., a layer, film, region, or substrate) is referred to as being "on" another element), the element may be directly on the other element, or there may be intermediate elements.

[0059] As used herein, the term "substituted" refers to a hydrogen atom replaced by deuterium, halogen, hydroxyl, thiol, cyano, nitro, carbonyl, -NRR' (wherein R and R' can each independently be hydrogen, a substituted or unsubstituted C1 to C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group), -SiRR'R" (wherein R, R ' and R" may each independently be hydrogen, a substituted or unsubstituted C1 to C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group), a C1 to C30 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkylsilanyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a C1 to C20 thioether group, or (e.g., any suitable) combination thereof. The term "unsubstituted" means that a hydrogen atom is not replaced by another substituent and remains as a hydrogen atom.

[0060] If no definition is otherwise provided (eg, when no definition is otherwise provided), the term "alkyl" as used herein refers to a straight or branched aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" without any double or triple bonds.

[0061] The alkyl group may be a C1 to C10 alkyl group. For example, the alkyl group may be a C1 to C8 alkyl group, a C1 to C7 alkyl group, a C1 to C6 alkyl group, or a C1 to C5 alkyl group. For example, the C1 to C5 alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a 2,2-dimethylpropyl group.

[0062] Unless otherwise defined (eg, when not otherwise defined), the term "cycloalkyl" as used herein refers to a monovalent cyclic aliphatic hydrocarbon group.

[0063] The cycloalkyl group may be a C3 to C10 cycloalkyl group, such as a C3 to C8 cycloalkyl group, a C3 to C7 cycloalkyl group, or a C3 to C6 cycloalkyl group. For example, the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, but the present disclosure is not limited thereto.

[0064] The term "aryl" as used herein refers to a cyclic substituent in which all atoms in the cyclic substituent have p orbitals and the p orbitals are conjugated, and may include monocyclic or fused-ring polycyclic functional groups (ie, rings that share adjacent pairs of carbon atoms).

[0065] Unless otherwise defined, the term "alkenyl" as used herein refers to an aliphatic unsaturated alkenyl group which is a straight or branched aliphatic hydrocarbon group including at least one double bond.

[0066] Unless otherwise defined, the term "alkynyl" as used herein refers to an aliphatic unsaturated alkynyl group which is a straight or branched aliphatic hydrocarbon group including at least one triple bond.

[0067] In the chemical formulas set forth herein, t-Bu refers to tert-butyl.

[0068] Hereinafter, semiconductor photoresist compositions according to some embodiments are described.

[0069] The semiconductor photoresist composition according to some embodiments includes an organometallic compound represented by Chemical Formula 1 and a solvent.

[0070] [Chemical formula 1]

[0071] (R 1 ) n1 -M-[(X)-R 2 ] m1

[0072] In Chemical Formula 1,

[0073] M can be a tetravalent metal, a pentavalent metal or a hexavalent metal,

[0074] R 1It may be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or L a -OR a (Where L a may be a substituted or unsubstituted C1 to C20 alkylene group, and R a may be a substituted or unsubstituted C1 to C20 alkyl group),

[0075] R 2 It may be tert-butyl, benzoyl, pivaloyl, acetyl, tert-butyldiphenylsilyl, tert-butyldimethylsilyl, allyl, tetrahydropyranyl, methoxymethyl, benzyl ether, tert-butyl ether, p-toluenesulfonyl, 2-phenylvinyl, benzyl, trifluoromethyl, benzyl ester, tert-butyl ester, 9-fluorenylmethyl or triphenylmethyl,

[0076] X can be O-[L 1 -O] n2 (Where L 1 may be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, and n2 may be an integer selected from 0 to 10), OC(O)-[L 2 -C(O)O] n3 (Where L 2 may be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, and n3 may be an integer selected from 0 to 10), N(R 3 )-[L 3 -N(R 4 )] n4 (Where L 3 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 3 and R 4 may each independently be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n4 may be an integer selected from 0 to 10), N(R 5 )C(O)-[L 4 -N(R 6 )C(O)]n5 (Where L 4 may be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 5 and R 6 may each independently be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n5 may be an integer selected from 0 to 10), or N(R 7 )CN(R 8 )-[L 5 -N(R 9 )CN(R 10 )] n6 (Where L 5 may be a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or (for example, any suitable) combination thereof, R 7 to R 10 may each independently be hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or (e.g., any suitable) combination thereof, and n6 may be an integer selected from 0 to 10),

[0077] n1 and m1 can each independently be an integer from 1 to 5, and

[0078] 4≤n1+m1≤6.

[0079] According to the present disclosure, the organometallic compound has R 2 The invention has a bulky structure by substitution and thus may have excellent or appropriate storage stability and moisture resistance.

[0080] In addition, during the exposure, R 2 The deprotection of , and condensation with surrounding or adjacent organometallic compound molecules occurs through X to form (or provide) a cluster, thereby improving sensitivity and resolution.

[0081] In some embodiments, M may be one selected from Sn, Sb, I, Te, In, Ag, Ni, Bi, and Po.

[0082] In an embodiment, M may be Sn.

[0083] In some embodiments, R1 It may be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or L a -OR a (where L a may be a substituted or unsubstituted C1 to C10 alkylene group, and R a may be a substituted or unsubstituted C1 to C10 alkyl group),

[0084] X can be O, OC(O), N(R 3 )(where R 3 may be hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, substituted or unsubstituted C6 to C20 aryl, or (for example, any suitable) combination thereof), N(R 5 )C(O)(where R 5 may be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof (e.g., any suitable combination), or N(R 7 )CN(R 8 )(where R 7 and R 8 They may each independently be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or (for example, any suitable) combination thereof).

[0085] In some embodiments, R 1 The radicals may be methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valeryl, ethoxy, propoxy, or a combination thereof (e.g., any suitable one).

[0086] In some embodiments, R 3 to R 10Each may independently be hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, or a combination thereof (e.g., any suitable combination).

[0087] The organometallic compound may be one selected from the compounds listed in Group 1.

[0088] [Group 1]

[0089]

[0090]

[0091] The organometallic compound moderately or strongly absorbs extreme ultraviolet light at about 13.5 nm and may have excellent or moderate sensitivity to relatively high energy light.

[0092] The organometallic compound may be included in an amount of about 1 wt % to about 30 wt %, such as about 1 wt % to about 25 wt %, about 1 wt % to about 20 wt %, about 1 wt % to about 15 wt %, about 1 wt % to about 10 wt %, or about 1 wt % to about 5 wt %, based on 100 wt % of the semiconductor photoresist composition, and the present disclosure is not limited thereto. If the content (e.g., amount) of the organometallic compound is within the above range (e.g., when the content (e.g., amount) of the organometallic compound is within the above range), the storage stability and etching resistance of the semiconductor photoresist composition are improved, and the resolution characteristics are improved.

[0093] Since the semiconductor photoresist composition according to some embodiments includes the above-mentioned organometallic compound, a semiconductor photoresist composition having excellent or appropriate sensitivity and stability may be provided.

[0094] The solvent of the semiconductor photoresist composition according to some embodiments may be an organic solvent, and may be, for example, an aromatic compound (e.g., xylene, toluene and / or similar compounds), an alcohol (e.g., 4-methyl-2-pentenol, 4-methyl-2-propanol, 1-butanol, methanol, isopropanol and / or 1-propanol), an ether (e.g., anisole and / or tetrahydrofuran), an ester (n-butyl acetate, propylene glycol monomethyl ether acetate, ethyl acetate and / or ethyl lactate), a ketone (e.g., methyl ethyl ketone and / or 2-heptanone), one or more thereof, or a (e.g., any suitable) mixture (e.g., combination), but the present disclosure is not limited thereto.

[0095] The semiconductor photoresist composition according to some embodiments may further include a resin in addition to the above-described organometallic compound and solvent.

[0096] The resin may be a phenolic resin comprising at least one aromatic moiety of Group 2.

[0097] [Group 2]

[0098]

[0099] The resin may have a weight average molecular weight of about 500 to about 20,000.

[0100] The resin may be included in an amount of about 0.1 wt % to about 50 wt % based on the total amount of the semiconductor photoresist composition.

[0101] If the resin is included in the above content (eg, amount) range (eg, when the resin is included in the above content (eg, amount) range), the semiconductor photoresist composition may have excellent or appropriate etching resistance and heat resistance.

[0102] The semiconductor photoresist composition according to some embodiments may include the aforementioned organometallic compound, solvent and resin (e.g., consisting of the aforementioned organometallic compound, solvent and resin). However, the semiconductor photoresist composition according to some embodiments may also include one or more additives as needed. Examples of additives may include (e.g., may be) surfactants, cross-linking agents, leveling agents, organic acids, quenchers or (e.g., any suitable) combinations thereof.

[0103] The surfactant may include, for example, alkylbenzene sulfonate, alkyl pyridinium salt, polyethylene glycol, quaternary ammonium salt, or (eg, any suitable) combination thereof, but the present disclosure is not limited thereto.

[0104] The crosslinking agent may include (for example, may be) a melamine-based crosslinking agent, a substituted urea-based crosslinking agent, an acrylic crosslinking agent, an epoxy resin-based crosslinking agent, and / or a polymer-based crosslinking agent, but the present disclosure is not limited thereto. In some embodiments, the crosslinking agent may have at least two substituents that form (or provide) crosslinking, such as the following compounds: methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, 4-hydroxybutyl acrylate, acrylic acid, polyurethane acrylate, acryl methacrylate, 1,4-butanediol diglycidyl ether, glycidol, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, trimethylpropane triglycidyl ether, 1,3-bis(glycidyloxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, and / or similar compounds.

[0105] The leveling agent may be used to improve coating flatness during printing, and may be a suitable leveling agent that is commercially available.

[0106] The organic acid may include p-toluenesulfonic acid, benzenesulfonic acid, p-dodecylbenzenesulfonic acid, 1,4-naphthalene disulfonic acid, methanesulfonic acid, fluorinated sulfonium salts, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or (eg, any suitable) combinations thereof, but the present disclosure is not limited thereto.

[0107] The quencher may include (eg, may be) diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or (eg, any suitable) combination thereof.

[0108] The amount of additives used in the photoresist composition can be controlled or selected depending on the desired or suitable properties.

[0109] In one or more embodiments, the semiconductor photoresist composition may further include a silane coupling agent as an adhesion enhancer to improve the close contact force with the substrate (e.g., to improve the adhesion of the semiconductor photoresist composition to the substrate). The silane coupling agent may be, for example: a silane compound including a carbon-carbon unsaturated bond, such as vinyl trimethoxysilane, vinyl triethoxysilane, vinyl trichlorosilane and / or vinyl tri(β-methoxyethoxy)silane; 3-methacryloxypropyl trimethoxysilane, 3-acryloxypropyl trimethoxysilane, p-phenylyl trimethoxysilane, 3-methacryloxypropyl methyl dimethoxysilane, 3-methacryloxypropyl methyl diethoxysilane; trimethoxy [3- (phenylamino) propyl] silane and / or similar silane compounds, but the present disclosure is not limited thereto.

[0110] The semiconductor photoresist composition can be formed into a pattern with a relatively high aspect ratio without collapse (e.g., without any collapsed portion). Therefore, in order to form (or provide) a fine pattern with a width of, for example, about 5nm to about 100nm, about 5nm to about 80nm, about 5nm to about 70nm, about 5nm to about 50nm, about 5nm to about 40nm, about 5nm to about 30nm, about 5nm to about 20nm, or about 5nm to about 10nm, the semiconductor photoresist composition can be used for a photoresist process using a wavelength of about 5nm to about 150nm, for example, about 5nm to about 100nm, about 5nm to about 80nm, about 5nm to about 50nm, about 5nm to about 30nm, or about 5nm to about 20nm. Therefore, the semiconductor photoresist composition according to some embodiments can be used to realize extreme ultraviolet lithography using an EUV light source with a wavelength of about 13.5nm.

[0111] According to some embodiments, a method for forming (or providing) a pattern using the semiconductor photoresist composition is provided. For example, the pattern produced may be a photoresist pattern.

[0112] According to some embodiments, the method of forming (or providing) a pattern includes: forming (or providing) an etching target layer on a substrate; coating the semiconductor photoresist composition on the etching target layer to form (or provide) a photoresist layer; patterning the photoresist layer to form (or provide) a photoresist pattern; and etching the etching target layer using the photoresist pattern as an etching mask.

[0113] In the following, reference is made to Figures 1 to 5 A method for forming (or providing) a pattern using the semiconductor photoresist composition is described. Figures 1 to 5 is a cross-sectional view for illustrating a method of forming (or providing) a pattern using a semiconductor photoresist composition according to some embodiments. Here, unless otherwise defined, steps, tasks, or actions listed in a particular order should not be interpreted as necessarily meaning that the invention or claims require the particular order. That is, the general rule is that unless the steps, tasks, or actions of a method (e.g., the method of the claims) actually state an order, these steps, tasks, or actions should not be interpreted as requiring an order.

[0114] Reference Figure 1 , an object to be etched is prepared. The object to be etched may be a thin film 102 formed on a semiconductor substrate 100. Hereinafter, the object to be etched is limited to the thin film 102. The entire surface of the thin film 102 is cleaned to remove impurities and / or the like remaining on the surface. The thin film 102 may be, for example, a silicon nitride layer, a polysilicon layer, or a silicon oxide layer.

[0115] Subsequently, a resist base layer composition for providing a resist base layer 104 is spin-coated on the surface of the cleaned thin film 102. However, the present disclosure is not limited thereto, and any suitable coating method may be used, such as spray coating, dip coating, blade coating, printing method (e.g., inkjet printing and screen printing), and / or the like.

[0116] In some embodiments, a coating process for providing a resist bottom layer may not be provided, and hereinafter, a process including a coating process for providing a resist bottom layer is described.

[0117] Then, the applied composition is dried and baked to form (or provide) a resist bottom layer 104 on the thin film 102. The baking may be performed at about 100°C to about 500°C, for example, about 100°C to about 300°C.

[0118] The resist bottom layer 104 is formed between the substrate 100 and the photoresist layer 106, and therefore, if radiation reflected from the interface between the substrate 100 and the photoresist layer 106 or the hard mask between the layers is scattered into an unintended photoresist area (for example, when the radiation is scattered into an unintended photoresist area), non-uniformity can be prevented or reduced and unintended pattern formation of the photoresist can be prevented or reduced.

[0119] Reference Figure 2 , a photoresist layer 106 is formed by coating a semiconductor photoresist composition on the resist base layer 104. The photoresist layer 106 is obtained by coating the above-mentioned semiconductor photoresist composition on the thin film 102 formed on the substrate 100 and then curing it by heat treatment.

[0120] In some embodiments, forming a pattern using a semiconductor photoresist composition may include coating the semiconductor photoresist composition on the substrate 100 having the thin film 102 thereon by spin coating, slit coating, inkjet printing and / or the like, and then drying it to form (or provide) a photoresist layer 106.

[0121] The semiconductor photoresist composition has been described in more detail and will not be described again herein.

[0122] Subsequently, a first baking process is performed on the substrate 100 having the photoresist layer 106. The first baking process may be performed at about 80°C to about 120°C.

[0123] Reference Figure 3 , the patterned mask 110 may be used to selectively expose the photoresist layer 106 .

[0124] For example, exposure can use activating radiation using the following light: light with a relatively high energy wavelength, such as extreme ultraviolet (EUV; wavelength of about 13.5nm), electron beam (E-Beam), etc.; and light with a relatively short wavelength, such as i-line (wavelength of about 365nm), KrF excimer laser (wavelength of about 248nm), ArF excimer laser (wavelength of about 193nm), etc.

[0125] Light used for exposure according to some embodiments may have a relatively short wavelength (in the range of about 5 nm to about 150 nm) and a relatively high-energy wavelength, such as extreme ultraviolet light (EUV; wavelength of 13.5 nm), electron beam (E-Beam), etc.

[0126] By forming (or providing) a polymer through a cross-linking reaction (eg, condensation between organometallic compounds), the exposed region 106 b of the photoresist layer 106 has a different solubility from the unexposed region 106 a of the photoresist layer 106 .

[0127] Subsequently, a second baking process is performed on the substrate 100. The second baking process may be performed at a temperature of about 90° C. to about 200° C. Due to the second baking process, the exposed region 106 b of the photoresist layer 106 becomes insoluble (eg, not easily soluble) in a developer.

[0128] exist Figure 4 In the process, the unexposed area 106a of the photoresist layer is dissolved and removed by a developer to form (or provide) a photoresist pattern 108. For example, an organic solvent such as 2-heptanone and / or the like is used to dissolve and remove the unexposed area 106a of the photoresist layer to complete the photoresist pattern 108 corresponding to the negative image.

[0129] As described above, the developer used in the method for forming (or providing) a pattern according to some embodiments may be an organic solvent. The organic solvent used in the method for forming (or providing) a pattern according to some embodiments may be, for example, one or more of: ketones, such as methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, and / or similar ketones; alcohols, such as 4-methyl-2-propanol, 1-butanol, isopropanol, 1-propanol, methanol, and / or similar alcohols; esters, such as propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate, n-butyl acetate, butyrolactone, and / or similar esters; aromatic compounds, such as benzene, xylene, toluene, and / or similar aromatic compounds; and / or (e.g., any suitable) combinations thereof.

[0130] However, the photoresist pattern according to some embodiments is not necessarily limited to a negative image, but may also be formed to have a positive image. Herein, the developer used to form (or provide) a positive image may be a quaternary ammonium hydroxide composition, such as tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide and / or (e.g., any suitable) combination thereof.

[0131] As described above, exposure to light having relatively high energy, such as extreme ultraviolet (EUV; wavelength of 13.5 nm), electron beam (E-Beam), and light having relatively short wavelength, such as i-line (wavelength of about 365 nm), KrF excimer laser (wavelength of about 248 nm), ArF excimer laser (wavelength of about 193 nm), etc., can provide a photoresist pattern 108 having a width of about 5 nm to about 100 nm. For example, the photoresist pattern 108 may have a width of about 5 nm to about 90 nm, about 5 nm to about 80 nm, about 5 nm to about 70 nm, about 5 nm to about 60 nm, about 5 nm to about 50 nm, about 5 nm to about 40 nm, about 5 nm to about 30 nm, about 5 nm to about 20 nm, or about 5 nm to about 10 nm.

[0132] In addition, the photoresist pattern 108 may have a pitch with a half pitch less than or equal to about 50 nm, for example, less than or equal to about 40 nm, less than or equal to about 30 nm, less than or equal to about 20 nm, or less than or equal to about 10 nm, and the photoresist pattern 108 may have a line width roughness less than or equal to about 5 nm, less than or equal to about 3 nm, less than or equal to about 2 nm, or less than or equal to about 1 nm.

[0133] Subsequently, the resist bottom layer 104 is etched using the photoresist pattern 108 as an etching mask. Through this etching process, an organic layer pattern 112 is formed. The organic layer pattern 112 may also have a width corresponding to the width of the photoresist pattern 108.

[0134] Reference Figure 5 The exposed thin film 102 is etched by using the photoresist pattern 108 as an etching mask. Thus, the thin film is formed into a thin film pattern 114.

[0135] The etching of the film 102 may be, for example, dry etching using an etching gas, and the etching gas may be, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 or a mixed gas thereof.

[0136] In the exposure process, the thin film pattern 114 formed using the photoresist pattern 108 (which is formed by the exposure process performed using the EUV light source) may have a width corresponding to the width of the photoresist pattern 108. For example, the thin film pattern 114 may have a width of 5 nm to 100 nm, which is equal to or substantially equal to the width of the photoresist pattern 108. For example, the thin film pattern 114 formed using the photoresist pattern 108 (which is formed by the exposure process performed using the EUV light source) may have a width of about 5 nm to about 90 nm, about 5 nm to about 80 nm, about 5 nm to about 70 nm, about 5 nm to about 60 nm, about 5 nm to about 50 nm, about 5 nm to about 40 nm, about 5 nm to about 30 nm, or about 5 nm to about 20 nm, and in an embodiment may have a width less than or equal to about 20 nm, which is the same or substantially the same as the width of the photoresist pattern 108.

[0137] Hereinafter, the present disclosure will be described in more detail by way of an example of the preparation of the above semiconductor photoresist composition. However, the present disclosure is not technically limited by the following examples.

[0138] (Synthesis of Organometallic Compounds)

[0139] Synthesis example 1

[0140] 25 mL of propionic acid was slowly added dropwise to tert-butyltriphenyltin compound (10 g, 25.6 mmol) at room temperature, and then heated under reflux at 110° C. for 24 hours. Thereafter, the temperature was lowered to room temperature, and propionic acid was vacuum distilled to obtain a compound represented by Chemical Formula 2.

[0141] [Chemical formula 2]

[0142]

[0143] Synthesis example 2

[0144] An equal amount of mono-tert-butyl succinate was slowly dropped into the compound represented by Chemical Formula 2 obtained in Synthesis Example 1, and then stirred at room temperature for 24 hours, thereby obtaining a compound represented by Chemical Formula 3.

[0145] [Chemical formula 3]

[0146]

[0147] Synthesis example 3

[0148] The synthesis was performed in substantially the same manner as in Synthesis Example 2, except that mono-tert-butyl malonate was used instead of mono-tert-butyl succinate, thereby obtaining a compound represented by Chemical Formula 4.

[0149] [Chemical formula 4]

[0150]

[0151] Synthesis example 4

[0152] Synthesis was performed in substantially the same manner as in Synthesis Example 2, except that 3-((tert-butyldimethylsilyl)oxy)-propanol was used instead of mono-tert-butyl succinate, thereby obtaining a compound represented by Chemical Formula 5.

[0153] [Chemical formula 5]

[0154]

[0155] Synthesis example 5

[0156] The synthesis was performed in substantially the same manner as in Synthesis Example 2, except that an n-butyltriphenyltin compound was used instead of the tert-butyltriphenyltin compound, thereby obtaining a compound represented by Chemical Formula 6.

[0157] [Chemical formula 6]

[0158]

[0159] (Preparation of semiconductor photoresist composition)

[0160] Examples 1 to 3 and Comparative Examples 1 and 2

[0161] The compounds represented by Chemical Formula 2 to Chemical Formula 6 obtained in Synthesis Examples 1 to 5 were respectively dissolved in 3 wt % 4-methyl-2-pentanol and filtered through a 0.1 μm polytetrafluoroethylene (PTFE) syringe filter to prepare a photoresist composition.

[0162] A 4-inch diameter circular silicon wafer having a native oxide surface was used as a substrate for thin film deposition. Prior to depositing the resist film, the wafer was treated in a UV ozone cleaning system for 10 minutes, and then the resist composition was spin-coated on the wafer at 1500 rpm for 30 seconds and baked at 120° C. for 120 seconds to form (or provide) the resist film. Thereafter, the thickness of the resist film (after coating and baking) was measured using ellipsometry, wherein the thickness was 20 nm for each of Examples 1 to 3 and Comparative Examples 1 to 2.

[0163] Assessment 1: Sensitivity Assessment

[0164] The substrate deposited with the resist film was exposed to an electron beam with an accelerating voltage of 100 kV to form (or provide) nanowires with a half pitch of 40 nm. The irradiated substrate was exposed to 40 ° C for 30 seconds, then immersed in a petri dish containing 2-heptanone for 60 seconds, the substrate was taken out, the substrate was cleaned with the same solvent for about 10 seconds, and finally baked at 150 ° C. In order to confirm the pattern performance of the patterned substrate, the critical dimension (critical dimension, CD) size of the formed line was measured using a field emission scanning electron microscopy (FE-SEM) image. The sensitivity is expressed as follows:

[0165] ◎If 1000Uc / cm 2 The CD size is greater than or equal to 40nm under energy,

[0166] ○If 1000Uc / cm 2 The CD size is greater than or equal to 35nm at the energy, and

[0167] △If at 1000Uc / cm 2 The CD size is less than 35nm at the lowest energy.

[0168] Assessment 2: Assessment of moisture stability

[0169] In order to analyze the degree of change due to moisture, 10 wt % of the corresponding tin compound (organic metal compound) used in Examples 1 to 3 and Comparative Examples 1 to 2 was dissolved in a 1-methoxy-2-propyl acetate solvent containing 1 wt % of water. 119 Sn nuclear magnetic resonance (NMR) measurement The results were evaluated according to the following judgment criteria and are shown in Table 1.

[0170] ※Evaluation criteria

[0171] ◎: No change in NMR peak.

[0172] ○: Total score changes from 1% to 29%

[0173] △: Total integral value changes from 30% to 89%

[0174] X: The change in the total integral value is greater than or equal to 90%

[0175] Assessment 3: Assessment of storage stability

[0176] The storage stability of the organometallic compounds used in Examples 1 to 3 and Comparative Examples 1 and 2 was evaluated based on the following judgment criteria, and the results are shown in Table 1.

[0177] [Storage stability]

[0178] After the semiconductor photoresist compositions according to Examples 1 to 3 and Comparative Examples 1 and 2 were left at room temperature (20±5° C.) for a period of time, the degree of precipitation was visually observed and evaluated according to the storage standard.

[0179] ※Evaluation criteria

[0180] ◎: Can be stored for more than or equal to 4 months

[0181] ○: Can be stored for more than or equal to 3 months and less than 4 months

[0182] △: Can be stored for more than or equal to 1 month and less than 3 months

[0183] X: Can be stored for less than two weeks

[0184] (Table 1)

[0185] Organometallic compounds Storage stability Moisture stability Sensitivity Example 1 Chemical formula 3 ◎ ◎ ◎ Example 2 Chemical formula 4 ○ ○ ◎ Example 3 Chemical formula 5 ○ ◎ ○ Comparative Example 1 Chemical formula 2 △ △ △ Comparative Example 2 Chemical formula 6 △ X △

[0186] As can be seen from the results in Table 1, the semiconductor photoresist composition according to the example exhibits excellent or appropriate sensitivity and significantly improved storage stability compared to the composition according to the comparative example.

[0187] The use of “may” when describing embodiments of the inventive concept means “one or more embodiments of the inventive concept”.

[0188] The terms "about" and similar terms used herein are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measured or calculated values ​​that one of ordinary skill in the art would recognize. "About" as used herein includes the stated value and means within an acceptable range of deviations of the particular value determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, ±5% of the stated value.

[0189] In addition, any numerical range described herein is intended to include all sub-ranges of the same numerical precision that fall within the range. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges between (and including) the minimum value 1.0 and the maximum value 10.0, i.e., having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as (for example) 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits that fall within it, and any minimum numerical limit described in this specification is intended to include all higher numerical limits that fall within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly state any sub-ranges that fall within the range explicitly stated herein.

[0190] While the disclosure has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the disclosure is not limited to the disclosed embodiments, but on the contrary, the disclosure is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims and their equivalents.

Claims

1. A semiconductor photoresist composition comprising: an organometallic compound represented by Chemical Formula 1; and Solvents, [Chemical formula 1] (R 1 ) n1 -M-[(X)-R 2 ] m1 in, In Chemical Formula 1, M is a tetravalent metal, a pentavalent metal or a hexavalent metal, R 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or L a -OR a , where L a is a substituted or unsubstituted C1 to C20 alkylene group, and R a is a substituted or unsubstituted C1 to C20 alkyl group, R 2 is tert-butyl, benzoyl, pivaloyl, acetyl, tert-butyldiphenylsilyl, tert-butyldimethylsilyl, allyl, tetrahydropyranyl, methoxymethyl, benzyl ether, tert-butyl ether, p-toluenesulfonyl, 2-phenylvinyl, benzyl, trifluoromethyl, benzyl ester, tert-butyl ester, 9-fluorenylmethyl or triphenylmethyl, X is O-[L 1 -O] n2 、O-C(O)-[L 2 -C(O)O] n3 、N(R 3 )-[L 3 -N(R 4 )] n4 、N(R 5 )C(O)-[L 4 -N(R 6 )C(O)] n5 or N(R 7 )C-N(R 8 )-[L 5 -N(R 9 )C-N(R 10 )] n6 , L 1 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, and n2 is an integer selected from 0 to 10, L 2 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, and n3 is an integer selected from 0 to 10, L 3 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, R 3 and R 4 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, or substituted or unsubstituted C6 to C30 aryl, and n4 is an integer selected from 0 to 10, L 4 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, R 5 and R 6 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, or substituted or unsubstituted C6 to C30 aryl, and n5 is an integer selected from 0 to 10, L 5 is a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C6 to C30 arylene group, R 7 to R 10 are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, or substituted or unsubstituted C6 to C30 aryl, and n6 is an integer selected from 0 to 10, n1 and m1 are each independently an integer selected from 1 to 5, and 4≤n1+m1≤6.

2. The semiconductor photoresist composition according to claim 1, wherein M is Sn, Sb, I, Te, In, Ag, Ni, Bi or Po.

3. The semiconductor photoresist composition according to claim 1, wherein M is Sn.

4. The semiconductor photoresist composition according to claim 1, wherein R 1 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or L a -OR a , where L a is a substituted or unsubstituted C1 to C10 alkylene group, and R a is a substituted or unsubstituted C1 to C10 alkyl group, and X is O, OC(O), N(R 3 )、N(R 5 )C(O) or N(R 7 )CN(R 8 ), R 3 is hydrogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C2 to C10 alkynyl, or substituted or unsubstituted C6 to C20 aryl, R 5 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, or a substituted or unsubstituted C6 to C20 aryl group, and R 7 and R 8 Each is independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, or a substituted or unsubstituted C6 to C20 aryl group.

5. The semiconductor photoresist composition according to claim 1, wherein R 1 is methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valeryl, ethoxy or propoxy.

6. The semiconductor photoresist composition according to claim 1, wherein R 3 to R 10 Each is independently hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl or benzyl.

7. The semiconductor photoresist composition according to claim 1, wherein the organometallic compound is one selected from the compounds listed in Group 1, [Group 1] 8. The semiconductor photoresist composition according to claim 1, wherein the amount of the organic metal compound is 1 wt% to 30 wt% based on 100 wt% of the semiconductor photoresist composition. 9 . The semiconductor photoresist composition according to claim 1 , further comprising a surfactant, a crosslinking agent, a leveling agent, an organic acid, a quencher or a combination thereof.

10. A method for forming a pattern, the method comprising: forming an etching target layer on a substrate; coating the semiconductor photoresist composition according to any one of claims 1 to 9 on the etching target layer to form a photoresist layer; patterning the photoresist layer to form a photoresist pattern; as well as The etching target layer is etched using the photoresist pattern as an etching mask. 11 . The method according to claim 10 , wherein the photoresist pattern is formed using light having a wavelength of 5 nm to 150 nm.

12. The method of claim 10, further comprising providing a resist bottom layer between the substrate and the photoresist layer. 13 . The method of claim 10 , wherein the photoresist pattern has a width of 5 nm to 100 nm.

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